Patent Application
20240268224
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0004927, filed on Jan. 12, 2023, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
One or more aspects of embodiments of the present disclosure relate to a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.
Self-emissive devices (for example, organic light-emitting devices) are a class of light-emitting devices that 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.
In a light-emitting device, a first electrode is located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons may transition (i.e., relax) from an excited state to a ground state to thereby generate light.
Implementation of the light-emitting device in a display device requires (or there is a desire) that the light-emitting device (e.g., self-emissive device) possess reduced driving voltage, improved luminescence efficiency, and/or a long lifespan. Therefore, the need exists for development of a material for a light-emitting device which is capable of stably (or suitably) implementing these properties. For example, to implement a light-emitting device having high luminescence efficiency, materials for an emission layer having excellent or suitable energy levels are continuously being developed and/or desired.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, a light-emitting device includes:
In Formula 1,
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, electronic equipment includes the light-emitting device.
One or more embodiments of the present disclosure are directed toward an organometallic compound represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the above and other aspects, features, and advantages of certain embodiments of the present disclosure are incorporated in and constitute a part of this specification. The drawings illustrate example embodiments and, together with the following description taken in conjunction with the accompanying drawings, serve to make the principles of the present disclosure more apparent. In the drawings:
Reference will now be made in more detail to embodiments of the present disclosure, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and duplicative descriptions thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described, by referring to the drawings, to explain aspects of the present description.
As utilized herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “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, throughout the disclosure, the expression “at least one of a, b or c” indicates 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 terminology used herein is for the purpose of describing embodiments and is not intended to limit the embodiments described herein. Unless otherwise defined, all chemical names, technical and scientific terms, and terms defined in common dictionaries should be interpreted as having meanings consistent with the context of the related art, and should not be interpreted in an ideal or overly formal sense. It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element.
As used herein, singular forms such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “comprise,” “comprises,” “comprising,” “has,” “have,” “having,” “include,” “includes,” and/or “including,” when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
As used herein, the term “and/or” includes any, and all, combination(s) of one or more of the associated listed items.
The term “may” will be understood to refer to “one or more embodiments of the present disclosure,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments of the present disclosure,” each including a corresponding listed item.
It will be understood that when an element is referred to as being “on,” “connected to,” or “on” another element, it may be directly on, connected, or coupled to the other element or one or more intervening elements may also be present. When an element is referred to as being “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present.
Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper,” “bottom,” “top,” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the drawings. For example, if the device in the drawings is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” or “over” the other elements or features. Thus, the term “below” may encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure pertains. It is also to be understood that terms defined in commonly used dictionaries should be interpreted as having meanings consistent with meanings in the context of the related art, unless expressly defined herein, and should not be interpreted in an ideal or overly formal sense.
In this context, “consisting essentially of” means that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.
Further, in this specification, the phrase “on a plane,” or “plan view,” means viewing a target portion from the top, and the phrase “on a cross-section” means viewing a cross-section formed by vertically cutting a target portion from the side.
In one or more embodiments, a light-emitting device may include:
In one or more embodiments,
In one or more embodiments, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.
In one or more embodiments, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.
In one or more embodiments, the emission layer of the light-emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. For example, the organometallic compound may act as a dopant. For example, 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 nanometer (nm) to about 470 nm.
In one or more embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or a combination thereof. In one or more embodiments, the hole blocking layer may directly contact the emission layer.
In one or more embodiments, the light-emitting device may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a combination thereof, and
In Formula 3,
In one or more embodiments, the organometallic compound may include at least one deuterium.
In one or more embodiments, the second compound to the fourth compound may each include at least one deuterium.
In one or more embodiments, the second compound may include at least one silicon.
In one or more embodiments, the third compound may include at least one silicon.
In one or more embodiments, the light-emitting device may further include a second compound and a third compound in addition to the organometallic compound represented by Formula 1, and at least one of the second compound or the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, in addition to the organometallic compound. At least one of the organometallic compound or the second compound may include at least one deuterium. In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a third compound, a fourth compound, or a combination thereof, in addition to the organometallic compound and the second compound.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, in addition to the organometallic compound. At least one of the organometallic compound or the third compound may include at least one deuterium. In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, a fourth compound, or a combination thereof, in addition to the organometallic compound and the third compound.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include a fourth compound, in addition to the organometallic compound. At least one of the organometallic compound or the fourth compound may include at least one deuterium. The fourth compound may serve to improve color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device. In one or more embodiments, the composition and the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, a third compound, or a combination thereof, in addition to the organometallic compound and the fourth compound.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include a second compound and a third compound, in addition to the organometallic compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, or the third compound may include at least one deuterium.
In one or more embodiments, the emission layer of the light-emitting device may include: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound, or a combination thereof, and the emission layer may be to emit blue light.
In one or more embodiments, a maximum emission wavelength of the blue light may be in a range of about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
In one or more embodiments, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a combination thereof.
In one or more embodiments, the following compounds may be excluded from the third compound.
In one or more embodiments, a difference between a triplet energy level (electron volt (eV)) of the fourth compound and a singlet energy level (eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or, about 0 eV or higher and about 0.3 eV or lower).
In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including as ring-forming atoms, each of boron (B) and nitrogen (N)
In one or more embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share a boron atom (B).
In one or more embodiments, the fourth compound may include a condensed ring in which at least one third ring may be condensed with at least one fourth ring,
In one or more embodiments, the third compound may not include a (e.g., may exclude any) compound represented by Formula 3-1 described in the present specification.
In one or more embodiments, the second compound may include a compound represented by Formula 2:
In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or a combination thereof:
In one or more embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or a combination thereof:
In one or more embodiments, the light-emitting device may satisfy at least one of Conditions 1 to 4:
lowest unoccupied molecular orbital(LUMO)energy level(eV) of third compound>LUMO energy level(eV) of organometallic compound Condition 1
LUMO energy level(eV) of organometallic compound>LUMO energy level(eV) of second compound Condition 2
highest occupied molecular orbital(HOMO)energy level(eV) of organometallic compound>HOMO energy level(eV) of third compound Condition 3
HOMO energy level(eV) of the third compound>HOMO energy level(eV) of the second compound Condition 4
The HOMO energy levels and the lowest LUMO energy levels of the organometallic compound, the second compound, and the third compound may each be a negative value, and may be measured according to any suitable method in the art.
In one or more embodiments, an absolute value of a difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the second compound may be about 0.1 eV or higher and about 1.0 eV or lower. In one or more embodiments, an absolute value of a difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the third compound may be about 0.1 eV or higher and about 1.0 eV or lower. In one or more embodiments, an absolute value of a difference between a HOMO energy level of the organometallic compound and a HOMO energy level of the second compound may be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher). In one or more embodiments, and an absolute value of a difference between a HOMO energy level of the organometallic compound and a HOMO energy level of the third compound may be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described, the balance between holes and electrons injected into the emission layer can be made, e.g., the amount of holes and the amount of electrons injected into the emission layer may be optimized or suitable for the purposes described herein. The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to the first embodiment, the organometallic compound may be included in the emission layer of the interlayer in the light-emitting device, the emission layer may further include a host, the organometallic compound may be different from the host, and the emission layer may be to emit phosphorescence or fluorescence produced by the organometallic compound. For example, according to the first embodiment, the organometallic compound may be a dopant or an emitter. In one or more embodiments, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
In one or more embodiments, phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
The emission layer may further include an ancillary dopant. The ancillary dopant may serve to improve luminescence efficiency from the first compound by effectively transferring energy to the organometallic compound as a dopant or an emitter.
The ancillary dopant may be different from the organometallic compound and the host.
In one or more embodiments, the ancillary dopant may be a delayed fluorescence-emitting compound.
In one or more embodiments, the ancillary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to the second embodiment, the organometallic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host and a dopant, the organometallic compound, the host and the dopant may be different from one another, and the emission layer may be to emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
In one or more embodiments, the organometallic compound in the second embodiment may serve as an auxiliary dopant that transfers energy to a dopant (or an emitter), not as a dopant.
In one or more embodiments, the organometallic compound in the second embodiment may serve as an emitter and as an auxiliary dopant that transfers energy to a dopant (or an emitter).
For example, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or a combination thereof) or any fluorescent dopant material (e.g., the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or a combination thereof).
In the first embodiment and the second embodiment, the blue light may be blue light having a maximum emission wavelength in a range of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
The ancillary dopant in the first embodiment may include, e.g., the fourth compound represented by Formula 502 or Formula 503.
The host in the first embodiment and the second embodiment may be any host material (e.g., the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or a combination thereof).
In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or a combination thereof.
In one or more embodiments, the light-emitting device may further include a capping layer located outside the first electrode and/or outside the second electrode.
In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer or the second capping layer. More details for the first capping layer and/or second capping layer may each independently be the same as described in the present specification.
In one or more embodiments, the light-emitting device may further include:
The expression that an “(interlayer and/or a capping layer) includes at least one organometallic compound represented by Formula 1” as utilized herein may be construed as meaning that the “(interlayer and/or the capping layer) may include one organometallic compound of Formula 1 or two different organometallic compounds of Formula 1.”
For example, the interlayer and/or capping layer may include Compound BD01 as the organometallic compound. In this regard, Compound BD01 exist in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the organometallic compound, Compounds BD01 and BD02. In this regard, Compounds BD01 and BD02 may exist in an identical layer (for example, Compounds BD01 and BD02 may all exist in an emission layer) or in different layers (for example, Compound BD01 may exist in an emission layer and Compound BD02 may exist in an electron transport region).
The term “interlayer” as utilized herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.
Another aspect provides an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In 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 a combination thereof. For more details on the electronic apparatus, related descriptions provided herein may be referred to.
In one or more embodiments, electronic equipment may include the light-emitting device.
For example, the electronic equipment may be one selected from among 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/or a signboard.
One or more embodiments include an organometallic compound represented by Formula 1. The detailed description of Formula 1 is the same as described in the present specification.
Methods of synthesizing the organometallic compound may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
In one or more embodiments, M may be Pt or Pd.
In one or more embodiments, M may be Pt.
In Formula 1, X11 to X13, X21, and X22 may each independently be C or N.
In one or more embodiments, X11 and X12 may each be C, and X13 may be N.
In one or more embodiments, X21 and X22 may be linked to each other via a chemical bond. Here, the chemical bond may be a single bond or a double bond.
In one or more embodiments, X21 and X22 may each be C.
Ring CY1 to ring CY4 in Formula 1 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, rings CY1 to CY4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzoxacillin group, a dibenzothiacillin group, a dibenzodihydroazacillin group, a dibenzodihydrodicillin group, a dibenzodihydrosiline group, a dibenzodioxine group, a dibenzooxathiine group, a dibenzooxazine group, a dibenzopyran group, a dibenzodithiine group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group.
In one or more embodiments, ring CY1 may be a pyridine group, a pyrimidine 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 one or more embodiments, ring CY1 may be a carbazole group.
In one or more embodiments, CY2 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.
In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, a phenanthrene group, an indole group, a carbazole group, a benzofuran group, a benzothiophene group, a quinoline group, or an isoquinoline group.
In one or more embodiments, rings CY3 and CY4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, or a cyclopentadiene group.
In one or more embodiments, rings CY3 and CY4 may each independently be a benzene group.
In one or more embodiments, at least one of CY3 and CY4 may be substituted with at least one deuterium.
In one or more embodiments, at least one of CY3 and CY4 may be substituted with at least one deuterium, and the other may not be substituted with deuterium (e.g., excluding deuterium).
L1 and L2 in Formula 1 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)—*′, *—Al(R1a)—*, *—Si(R1a)(R1b)—*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, and * and *′ may each indicate a binding site to a neighboring atom,
In Formula 1, 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-C6 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C6 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In one or more embodiments, R10a and Q1 to Q3 may each be as described herein.
In one or more embodiments, R1a and R1b may each independently be:
In one or more embodiments, L1 and L2 may each be a single bond.
In one or more embodiments, n1 and n2 in Formula 1 may each independently be an integer from 1 to 5.
In Formula 1, R1 to R8 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In one or more embodiments, R10a and Q1 to Q3 may each be as described herein.
In one or more embodiments, R1 to R8 may each independently be:
In one or more embodiments, R1 to R8 may each independently be:
In one or more embodiments, R1 to R8 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, a sec-propyl group, or a tert-butyl group.
In Formula 1, a1 may be an integer from 1 to 4, a2 may be an integer from 1 to 3, a3 may be an integer from 1 to 6, a4 may be an integer from 1 to 4, a5 may be an integer from 1 to 8, a6 may be an integer from 1 to 3, and a7 and a8 may each independently be an integer from 1 to 5.
In one or more embodiments, ring CY2 in Formula 1 may be selected from groups represented by Formulae L1 to L10:
In one or more embodiments, a group in Formula 1 that is represented by the portion
may be a group represented by Formula 1-1:
Unless defined otherwise, for example, R10a in Formula 1 may be:
Unless defined otherwise, for example, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 in Formula 1 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; 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 a combination thereof.
In the organometallic compound represented by Formula 1, because ring CY2 links a benzene group and ring CY1 in Formula 1 (i.e., through X21 and X22, which are linked to each other via a chemical bond), the conjugation (e.g., an intermolecular conjugation), of the organometallic compound may be enhanced or strengthened, thereby lowering the HOMO energy level of the organometallic compound and improving molecular stability and color purity. Therefore, it is possible to enhance or increase emission efficiency (e.g., of the light-emitting device) by utilizing or applying the structural and energetic features described herein in (or to) the emission layer and to enhance or improve the device lifespan. Accordingly, by utilizing the organometallic compound of the present disclosure, an electronic device (for example, an organic light-emitting device) having high efficiency, high color purity, and long lifespan characteristics may be implemented.
The symbols b51 to b53 in Formula 2 indicate the numbers of L51 to L53, respectively, and may each be an integer from 1 to 5. When b51 is 2 or more, two or more of L51(s) may be identical to or different from each other, when b52 is 2 or more, two or more of L52(s) may be identical to or different from each other, and when b53 is 2 or more, two or more of L53(s) may be identical to or different from each other. In one or more embodiments, b51 to b53 may each independently be 1 or 2.
L51 to L53 in Formula 2 may each independently be:
In one or more embodiments, in Formula 2, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between two or more L51(s), a bond between two or more L52(s), a bond between two or more L53(s), a bond between L51 and carbon between X54 and X55 in Formula 2, a bond between L52 and carbon between X54 and X56 in Formula 2, and a bond between L53 and carbon between X55 and X56 in Formula 2 may each be a “carbon-carbon single bond.”
In Formula 2, X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one of X54 to X56 may be N. R54 to R56 may each independently be the same as described above. In one or more embodiments, two or three of X54 to X56 may be N.
R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in the present specification 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 independently be the same as described in the present specification.
For example, i) R1 to R8 in Formula 1, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and/or 503, and iii) R10a may each independently be:
In Formula 91,
For example, in Formula 91,
In one or more embodiments, i) R1 to R8 in Formula 1, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be,
In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 may respectively indicate the number of R71(s) to R74(s) and R501(s) to R504(s), and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 is 2 or greater, at least two R71(s) may be identical to or different from each other, when a72 is 2 or greater, at least two R72(s) may be identical to or different from each other, when a73 is 2 or greater, at least two R73(s) may be identical to or different from each other, when a74 is 2 or greater, may be identical to or different from each other R74(s) may be identical to or different from each other, when a501 is 2 or greater, at least two R501(s) may be identical to or different from each other, when a502 is 2 or greater, at least two R502(s) may be identical to or different from each other, when a503 is 2 or greater, at least two R503(s) may be identical to or different from each other, and when a504 is 2 or greater, at least two R504(s) may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
In Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may each not be a phenyl group.
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be identical to each other.
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be different from each other.
In one or more embodiments, b51 and b52 in Formula 2 may each be 1, 2, or 3, and L51 and L52 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R51 and R52 in Formula 2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3), and
In one or more embodiments,
For example,
In Formulae 3-1 to 3-5, L81 to L85 may each independently be:
In one or more embodiments, in Formulae 3-1 and 3-2, a group represented by
may be represented by one selected from among Formulae CY71-1(1) to CY71-1(8),
may be represented by one selected from among Formulae CY71-2(1) to CY71-2(8), and/or
may be represented by one selected from among Formulae CY71-3(1) to CY71-3(32),
may be represented by one selected from among Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 3-5, a group represented by
may be represented by one selected from among Formulae CY71-5(1) to CY71-5(8):
In one or more embodiments, for 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),
In one or more embodiments, the organometallic compound represented by Formula 1 may be one of Compounds BD01 to BD120:
In one or more embodiments, M in Compounds BD01 to BD120 may be defined as described herein.
In one or more embodiments, the second compound may be one of Compounds ETH1 to ETH100:
In one or more embodiments, the third compound may be one of Compounds HTH1 to HTH40:
In one or more embodiments, the fourth compound may be one of Compounds DFD1 to DFD29:
In the compounds described, Ph represents a phenyl group, D5 represents substitution with five deuterium, and D4 represents substitution with four deuterium. For example, a group represented by
may be substantially the same as, or identical to, a group represented by
Hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work-function material that facilitates injection of holes. The term “high work-function material” as utilized herein refers to a substance (e.g., a metal or metal alloy) that requires a relatively high amount of energy to emit electrons from its surface.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or a 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 a combination thereof.
The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer, and an electron transport region located between the emission layer and the second electrode 150.
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 quantum dots, and/or the like.
In one or more embodiments, the interlayer 130 may include i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between two neighboring emitting units. When the interlayer 130 includes emitting units and a 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-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.
For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure. In one or more embodiments, the layers of each structure being stacked sequentially from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, and/or a combination thereof:
For example, each of Formulae 201 and 202 may include at least one selected from among groups represented by Formulae CY201 to CY217:
In one or more embodiments, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one selected from among groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one of Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one of Formulae CY201 to CY203, and may include at least one selected from among 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) a group represented by one of Formulae CY201 to CY217.
In one or more embodiments, the hole transport region may include one selected from among Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and/or a combination thereof:
A thickness of the hole transport region may be in a range of about 50 angstrom (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 a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. In one or more embodiments, the electron blocking layer may block or reduce the leakage of electrons from an emission layer to a 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
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
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 a combination thereof.
Examples of the quinone derivative are TCNQ, F4-TCNQ, and/or the like.
Examples of the cyano group-containing compound are HAT-CN and a compound represented by Formula 221.
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
Examples of the metal are an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); 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.
Examples of the metalloid are silicon (Si), antimony (Sb), tellurium (Te) and/or the like.
Examples of the non-metal are oxygen (O), halogen (for example, F, Cl, Br, I, etc.), and/or the like.
Examples of the compound including element EL1 and element EL2 are metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, or metalloid iodide), metal telluride, or a combination thereof.
Examples of the metal oxide are tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (for example, ReO3, etc.), and/or the like.
Examples of the metal halide are alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Examples of the alkaline earth metal halide are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
Examples of the transition metal halide are titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide are zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (for example, InI3, etc.), and tin halide (for example, SnI2, etc.).
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and/or the like.
An example of the metalloid halide is antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride are alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal telluride (for example, ZnTe, etc.), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other to emit white light. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In one or more embodiments, the emission layer may further include an auxiliary dopant that promotes energy transfer to a dopant (or emitter), in addition to the host and the dopant (or emitter). When the emission layer includes the dopant (or emitter) and the auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
The organometallic compound represented by Formula 1 in the present specification may serve as the dopant (or emitter), or may serve as the auxiliary dopant.
An amount of the dopant (or emitter) in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
The emission layer may include the organometallic compound represented by Formula 1. The amount (weight) of the organometallic compound in the emission layer may be about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight based on 100 parts by weight of the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable light-emission characteristics may be obtained without a substantial increase in driving voltage.
The host in the emission layer may include the second compound or the third compound described in the present specification, or a combination thereof.
In one or more embodiments, the host may include a compound represented by Formula 301:
In Formula 301,
For example, 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 a combination thereof:
In Formulae 301-1 and 301-2,
In one or more embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.
In one or more embodiments, the host may include at least one of 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-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl) benzene (TCP), or a combination thereof:
In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or a combination thereof.
The host may have one or more suitable modifications. For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.
The emission layer may include, as a phosphorescent dopant, the organometallic compound represented by Formula 1 as described in the present specification.
In one or more embodiments, the emission layer may include an organometallic compound represented by Formula 1, and when the organometallic compound represented by Formula 1 functions as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
In one or more embodiments, 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 a combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
For example, 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 402 is 2 or more, two ring A401(s) in two or more of L401(s) may be optionally linked to each other via T402, which is a linking group, or two ring A402(s) may be optionally linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be the same as described herein with respect to T401.
L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or a combination thereof.
The phosphorescent dopant may include, for example, at least one of compounds PD1 to PD25, or a combination thereof:
In one or more embodiments, the emission layer may include an organometallic compound represented by Formula 1, and when the organometallic compound represented by Formula 1 functions as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In one or more embodiments, the emission layer may include an organometallic compound represented by Formula 1, and when the organometallic compound represented by Formula 1 functions 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 a combination thereof.
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
For example, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
In one or more embodiments, xd4 in Formula 501 may be 2.
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each include at least one of Compounds FD1 to FD36, DPVBi, DPAVBi, or a combination thereof:
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described in the present specification.
The electron transport region may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron-transporting region may include a buffer layer, a hole blocking layer, an electron control layer, an electron-transporting layer, an electron injection layer, or a combination thereof.
For example, 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, the constituting layers of each structure being sequentially stacked from an emission layer.
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 π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
For example, the electron transport region may include a compound represented by Formula 601:
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include at least one of Compounds ET1 to ET46, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or a combination thereof:
A thickness of the electron transport region may be from 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 a combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be from about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be from about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The metal ion of an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of an 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 a combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, alkaline earth metal, a rare earth metal, an alkali metal-containing compound, alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or a combination thereof.
The alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or RbI; or a 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 the condition of 0<x<1), BaxCa1-xO (wherein x is a real number satisfying the condition of 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 a combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and/or the like.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one selected from among metal ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or a combination thereof.
The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a 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, an alkali metal halide); or ii) a) an alkali metal-containing compound (for example, an alkali metal halide), and b) an alkali metal, an alkaline earth metal, a rare earth metal, or a combination thereof. For example, 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 a combination thereof may be 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.
Returning to
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In particular, 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.
Light generated in an 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. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be enhanced or improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at 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 each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or a combination thereof. Optionally, the carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or a combination thereof. In one or more embodiments, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.
For example, at least one of the first capping layer or the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof.
In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include at least one of Compounds HT28 to HT33, at least one of Compounds CP1 to CP6, β-NPB, or a combination thereof:
The light-emitting device may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, 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 located in at least one direction in which light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue light, green light, or white light. For details on the light-emitting device, related description provided above may be referred to. In one or more embodiments, the color conversion layer may include a quantum dot.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be located among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, 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, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In particular, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a (e.g., may exclude any) quantum dot. For details on the quantum dot, related descriptions provided herein may be referred to. The first area, the second area, and/or the third area may each include a scatterer.
For example, 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 particular, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and 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.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located 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.
One or more functional layers may be additionally located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilize of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, 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 located 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 located 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 located on the activation layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located 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 located 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 located in contact with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT may be electrically connected to a light-emitting device to drive the light-emitting device, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is 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 located on the passivation layer 280. The passivation layer 280 may be located to expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be located to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. In one or more embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be located in the form of a common layer.
The second electrode 150 may be located 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 located on the second capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide (ITO), indium zinc oxide (IZO), or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or a combination thereof; or a combination of the inorganic films and the organic films.
The light-emitting apparatus of
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A display device 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 and/or power to display devices located or arranged on the display area DA may be located or arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board may be electrically connected, may be located or 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
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and 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 vehicle body may include a front panel, a bonnet (i.e., hood), a roof panel, a rear panel, a trunk, a filler provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear 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 device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a filler arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be spaced apart from each other in the +x direction or the −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the +x direction or the −x direction. In other words, an imaginary straight line L connecting the side window glasses 1100 may extend in the +x direction or the −x direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the +x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one embodiment, a plurality of side mirrors 1300 may be provided. Any one selected from among the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, an hodometer, an automatic shift selector indicator lamp, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a heater of a seat are disposed. The center fascia 1500 may be arranged on one side of the cluster 1400.
A passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In one or more embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be disposed to correspond to a passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one selected from among the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to one or more embodiments of the disclosure, an organic light-emitting display device display including the light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described above may be utilized in embodiments of the disclosure.
Referring to
Referring to
Referring to
Layers included in the hole transport region, the emission layer, and layers included in the electron transport region may be formed in one or more suitable regions by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and/or laser-induced thermal imaging.
When layers constituting the hole transport region, an emission layer, and layers constituting 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 angstrom per second (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 consisting of carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group 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 “cyclic group” as utilized herein may include 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. 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 terms “the cyclic group, the C3-C60 carbocyclic group, the C1-C60 heterocyclic group, the π electron-rich C3-C60 cyclic group, or the π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein 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, 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.
Examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group are a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. Examples of the divalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group are a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and specific examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having 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 the C2-C60 alkyl group, and examples thereof are an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having 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 the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having 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 the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 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, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having 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 specific examples are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term C3-C10 cycloalkenyl group utilized herein refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and specific examples thereof are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having 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 carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C60 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having 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. Examples of the C6-C60 aryl group are a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. 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. Examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C6-C60 aryloxy group” as utilized herein indicates -OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein indicates -SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” utilized herein refers to -A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term C2-C60 heteroarylalkyl group” utilized herein refers to -A106A107 (where A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
The term “R10a” as utilized herein refers to:
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and a combinations thereof.
The term “third-row transition metal” utilized herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
“Ph” as utilized herein refers to a phenyl group, “Me” as utilized herein refers to a methyl group, “Et” as utilized herein refers to an ethyl group, “ter-Bu” or “But” as utilized herein refers to a tert-butyl group, and “OMe” as utilized herein refers to a methoxy group.
The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In 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 embodiments and light-emitting devices according to embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
The materials 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-1 (yield: 75%).
Intermediate Compound BD01-1 (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-2 (yield: 90%).
Intermediate Compound BD01-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]) (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through a Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-3 (yield: 78%).
Intermediate Compound BD01-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-4 (yield: 75%).
The materials (9-(pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 1-bromo-2-iodobenzene (1.2 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-5 (yield: 78%).
Intermediate Compound BD01-5 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-6 (yield: 62%).
Intermediate Compound BD01-6 (1.0 eq), Intermediate Compound BD01-4 (1.3 eq), Pd2(dba)3(0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-7 (yield: 87%).
Intermediate Compound BD01-7 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl(35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD01-8 (yield: 89%).
Intermediate Compound BD01-8 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (1,2-dichlorobenzene) (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD01 (yield 55%).
The materials 2,6-dibromoaniline (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-1 (yield: 94%).
Intermediate Compound BD07-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through a Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-2 (yield: 80%).
Intermediate Compound BD07-2 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-3 (yield: 75%).
The materials (9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 1-bromo-2-iodobenzene (1.2 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-4 (yield: 66%).
Intermediate Compound BD07-4 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-5 (yield: 81%).
Intermediate Compound BD07-5 (1.0 eq), Intermediate Compound BD07-3 (1.3 eq), Pd2(dba)3(0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-6 (yield: 76%).
Intermediate Compound BD07-6 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD07-7 (yield: 83%).
Intermediate Compound BD07-7 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD07 (yield 52%).
The materials 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-1 (yield: 75%).
Intermediate Compound BD17-1 (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-2 (yield: 90%).
Intermediate Compound BD17-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-3 (yield: 78%).
Intermediate Compound BD17-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-4 (yield: 75%).
The materials (9-(pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 1,2-dibromo-4,5-di-tert-butylbenzene (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-5 (yield: 15%).
Intermediate Compound BD17-5 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-6 (yield: 67%).
Intermediate Compound BD17-6 (1.0 eq), Intermediate Compound BD17-4 (1.3 eq), Pd2(dba)3(0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-7 (yield: 75%).
Intermediate Compound BD17-7 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD17-8 (yield: 81%).
Intermediate Compound BD17-8 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD17 (yield 53%).
The materials 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-1 (yield: 75%).
Intermediate Compound BD25-1 (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-2 (yield: 90%).
Intermediate Compound BD25-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through a Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-3 (yield: 78%).
Intermediate Compound BD25-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-4 (yield: 75%).
The materials (9-(pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 2-bromo-3-iodonaphthalene (1.2 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-5 (yield: 70%).
Intermediate Compound BD25-5 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-6 (yield: 69%).
Intermediate Compound BD25-6 (1.0 eq), Intermediate Compound BD25-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-7 (yield: 88%).
Intermediate Compound BD25-7 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD25-8 (yield: 80%).
Intermediate Compound BD25-8 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD25 (yield 55%).
The materials 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-1 (yield: 75%).
Intermediate Compound BD41-1 (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran-H2O=4.1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-2 (yield: 90%).
Intermediate Compound BD41-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through a Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-3 (yield: 78%).
Intermediate Compound BD41-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-4 (yield: 75%).
The materials (9-(pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 1-bromo-2-iodobenzene (1.2 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-5 (yield: 15%).
Intermediate Compound BD41-5 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-6 (yield: 61%).
Intermediate Compound BD41-6 (1.0 eq), Intermediate Compound BD41-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-7 (yield: 85%).
Intermediate Compound BD41-7 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD41-8 (yield: 72%).
Intermediate Compound BD41-8 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD41 (yield: 50%).
The materials 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1(0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-1 (yield: 75%).
Intermediate Compound BD49-1 (1.0 eq), phenyl boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-2 (yield: 90%).
Intermediate Compound BD49-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium t-butoxide (4.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then was filtered through a Celite filter by utilizing dichloromethane, and the filtrate was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-3 (yield: 78%).
Intermediate Compound BD49-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and stirred at 80° C. for 12 hours. The reaction mixture was neutralized with NaOH and subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-4 (yield: 77%).
The materials (9-(pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (1.0 eq), 2,3-dibromocarbazole (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-5 (yield: 12%).
Intermediate Compound BD49-5 (1.2 eq), (3-bromophenyl)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3 (2.0 eq) were dissolved in tetrahydrofuran:H2O=4:1 (0.1 M) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing ethyl acetate and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-6 (yield: 55%).
Intermediate Compound BD49-6 (1.0 eq), Intermediate Compound BD49-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium t-butoxide (2.0 eq), and Xphos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and stirred at 110° C. for 4 hours. The reaction mixture was cooled at room temperature, and then subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-7 (yield: 91%).
Intermediate Compound BD49-7 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and stirred at 80° C. for 12 hours. The reaction mixture was subjected to an extraction process utilizing dichloromethane and washed three times by water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate, concentrated, and then subjected to column chromatography, so as to synthesize Intermediate Compound BD49-8 (yield: 79%).
Intermediate Compound BD49-8 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and was filtered through a Si filter by utilizing dichloromethane and n-hexane to remove o-DCB therefrom and synthesize Compound BD49 (yield: 56%).
1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples 1-6 are shown in Table 1. Synthesis methods of other compounds in addition to the compound synthesized in Synthesis Example may be easily recognized by those skilled in the art by referring to the synthesis paths and source materials.
1H NMR (CDCl3, 400 MHz)
indicates data missing or illegible when filed
The HOMO energy level (eV), LUMO energy level (eV), simulation maximum emission wavelength (λmaxsim), actual maximum emission wavelength (λmaxexp), and ratio of presence of triplet metal-to-ligand charge transfer state (3MLCT) of each of Compounds BD01, BD17, BD25, BD41, BD49, and BD07 were evaluated utilizing the DFT method of the Gaussian program, which is structure-optimized or enhanced at the B3LYP/6-31 G(d,p) level, and results thereof are shown in Table 2.
3MLCT(%)
As an anode, a substrate with 15 ohms per square centimeter (Ω/cm2) (1,200 angstrom (Å)) ITO glass thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
A quantity of 2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and a quantity of NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Compound BD01, which was the dopant, and ETH2: HTH29, which were a mixed host at the weight ratio of 5:5, were co-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å, wherein the ratio of the dopant to the mixed host was 10%, and the emission layer was a blue fluorescent emission layer. Subsequently, ETH2 was vacuum-deposited thereon to form a hole-blocking layer having a thickness of 50 Å. Then, Alq3 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, and then, LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å and Al was vacuum-deposited thereon to form an Al electrode having a thickness of 3,000 Å (cathode) to form an LiF/AI electrode, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices of Examples 2 to 6 and Comparative Examples 1 and 2 (CE-1 and CE-2) were manufactured in substantially the same manner as in Example 1, except that in forming the respective emission layers, Compounds BD07, BD17, BD25, BD41, and BD49 (Examples 2 to 6) and Compounds CE1 and CE2 (Comparative Examples 1 and 2 (CE-1 and CE-2)), were utilized as a dopant instead of Compound BD01, as shown in Table 3.
A voltage was applied to the light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 and 2 (CE-1 and CE-2) to establish in the light-emitting devices a current density of 50 milliamp per square centimeter (mA/cm2). Then the driving voltage, CIE(y), color conversion luminescence efficiency (C.C.L.E.), maximum emission wavelength (λmaxexp), and device lifespan obtained at 1000 candela per square meter (cd/m2) were measured by utilizing Keithley SMU 236 and luminance meter PR650, and the results thereof are shown in Table 3.
From Table 3, the organic light-emitting devices of Examples 1 to 6 were found to have lower HOMO energy levels than those of Comparative Examples 1 and 2, thereby providing (having) excellent or suitable color purity, luminescence efficiency, and device lifespan.
According to the one or more embodiments, by utilizing the organometallic compound, a light-emitting device having a relatively low driving voltage and high efficiency and a relatively high-quality electronic apparatus including the light-emitting device may be manufactured.
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 |
|---|---|---|---|
| 10-2023-0004927 | Jan 2023 | KR | national |
