Patent Application
20250151608
This application claims priority to and benefits of Korean Patent Application No. 10-2023-0148439 under 35 U.S.C. § 119, filed on Oct. 31, 2023 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.
Light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed.
In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as the holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.
It is to be understood that this background of the technology section is, in part, intended to provide useful background for understanding the technology. However, this background of the technology section may also include ideas, concepts, or recognitions that were not part of what was known or appreciated by those skilled in the pertinent art prior to a corresponding effective filing date of the subject matter disclosed herein.
Embodiments provide 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.
Embodiments provide a light-emitting device which may include:
In Formula 1,
In Formula 1A,
In an embodiment, the emission layer may include a host and a dopant; and the dopant may include the organometallic compound.
In an embodiment, 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, which is explained herein, a fourth compound that may be a delayed fluorescence compound, or any combination thereof, wherein the organometallic compound, the second compound, the third compound, and the fourth compound may be different from each other.
In an embodiment, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof; and the fourth compound may include at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
In an embodiment, the emission layer may include: the organometallic compound; and the second compound, the third compound, the fourth compound, or any combination thereof; and the emission layer may emit blue light.
Embodiments provide an electronic apparatus which may include the light-emitting device.
In an embodiment, the electronic apparatus may further include a thin-film transistor, wherein the thin-film transistor may include a source electrode and a drain electrode, and the first electrode of the light-emitting device may electrically be connected to at least one of the source electrode and the drain electrode.
In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
Embodiments provide an electronic equipment which may include the light-emitting device.
In an embodiment, the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Embodiments provide an organometallic compound which may be represented by Formula 1, which is explained herein.
In an embodiment, in Formula 1, M may be platinum (Pt), palladium (Pd), or gold (Au).
In an embodiment, in Formula 1, X2 and X3 may each be C; X4 may be N; a bond between X4 and M may be a coordinate bond; and a bond between X2 and M and a bond between X3 and M may each be a covalent bond.
In an embodiment, in Formula 1, ring CY1, ring CY2, ring CY31, ring CY32, and ring 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 dibenzooxasiline group, a dibenzothiasiline group, a dibenzodihydroazasiline group, a dibenzodihydrodihydrodisiline group, a dibenzodihydrosiline group, a dibenzodioxine group, a dibenzooxathiane 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 an embodiment, in Formula 1, L1 and L3 may each be a single bond; L2 may be *—O—*′ or *—S—*′; and n2 may be 1.
In an embodiment, in Formula 1, R1, R11, R2, R31, R32, and R4 may each independently be:
In an embodiment, in Formula 1,
may be a moiety represented by one of Formulae CY1(1) to CY1(11), which are explained herein,
may be a moiety represented by one of Formulae CY2(1) to CY2(13), which are explained herein,
may be a moiety represented by one of Formulae CY31(1) to CY31(6), which are explained herein,
may be a moiety represented by one of Formulae CY32(1) to CY32(16), which are explained herein, and
may be a moiety represented by one of Formulae CY4(1) to CY4(29), which are explained herein.
In an embodiment, in Formula 1A, X51 may be C(R51), X52 may be C(R52), X53 may be C(R53), X54 may be C(R54), X55 may be C(R55), X56 may be C(R56), X57 may be C(R57), and X58 may be C(R58).
In an embodiment, the organometallic compound may be represented by Formula 1-1, which is explained herein.
In an embodiment, the organometallic compound satisfies at least one of Conditions 1 to 12, which are explained herein.
It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purposes of limitation, and the disclosure is not limited to the embodiments described above.
The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the disclosure and principles thereof. The above and other aspects and features of the disclosure will be more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:
The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like reference numbers and reference characters refer to like elements throughout.
In the specification, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.
In the specification, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.
As used herein, the expressions used in the singular such as “a,” “an,” and “the,” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.
In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group consisting of” for the purpose of its meaning and interpretation. For example, “at least one of A, B, and C” may be understood to mean A only, B only, C only, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.
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 disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.
The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component 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, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.
It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.
An embodiment provides a light-emitting device which may include:
In an embodiment,
In embodiments, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.
In embodiments, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.
In embodiments, the emission layer of the light-emitting device may include a dopant and a host, and the dopant may include the organometallic compound represented by Formula 1. For example, the organometallic compound may serve as a dopant. For example, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in a range of, for example, about 430 nm to about 480 nm.
In embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In an embodiment, the hole blocking layer may contact (e.g., directly contact) the emission layer.
In an embodiment, 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 (for example a delayed fluorescence compound), or any combination thereof, and
In Formula 3,
In an embodiment, the organometallic compound may include at least one deuterium.
In embodiments, the second compound to the fourth compound may each independently include at least one deuterium.
In embodiments, the second compound may include at least one silicon.
In embodiments, the third compound may include at least one silicon.
In 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 and the third compound may include at least one deuterium, at least one silicon, or a combination thereof.
In an embodiment, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, in addition to the organometallic compound. At least one of the organometallic compound and the second compound may include at least one deuterium. For example, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the second compound.
In embodiments, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a third compound, in addition to the organometallic compound. At least one of the organometallic compound and the third compound may include at least one deuterium. For example, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the third compound.
In embodiments, the light-emitting device (e.g., 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 and the fourth compound may include at least one deuterium. The fourth compound may serve to improve the color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device. For example, the light-emitting device (e.g., the emission layer in the light-emitting device) may further include a second compound, a third compound, or any combination thereof, in addition to the organometallic compound and the fourth compound.
In embodiments, the light-emitting device (e.g., 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, and the third compound may include at least one deuterium.
In embodiments, the emission layer of the light-emitting device may include: the organometallic compound; and the second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer may emit blue light.
In embodiments, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 450 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 470 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 470 nm. For example, the blue light may have a maximum emission wavelength in a range of about 450 nm to about 470 nm, about 430 nm to about 465 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 465 nm. For example, the blue light may have a maximum emission wavelength in a range of about 450 nm to about 465 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 460 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 460 nm. For example, the blue light may have a maximum emission wavelength in a range of about 450 nm to about 460 nm.
In an embodiment, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In embodiments, the third compound may not include CBP or mCBP:
In an embodiment, the fourth compound may be a compound in which a difference between a triplet energy level (eV) and a singlet energy level (eV) may be in a range of about 0 eV to about 0.5 eV (or in a range of about 0 eV to about 0.3 eV).
In embodiments, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
In embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound in which two or more cyclic groups are condensed while sharing boron (B).
In embodiments, the fourth compound may include a ring in which at least one third ring is condensed with at least one fourth ring,
In an embodiment, the third compound may not include a compound represented by Formula 3-1, which is described herein.
In an embodiment, the second compound may include a compound represented by Formula 2:
In Formula 2,
In embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
In Formulae 3-1 to 3-5, ring CY71 to ring CY74 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group,
In embodiments, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
In Formulae 502 and 503,
In an embodiment, the light-emitting device may satisfy at least one of Conditions A to D:
A HOMO energy level and a LUMO energy level of each of the organometallic compound, the second compound, and the third compound may each be a negative value, and may be measured according to a method of the related art.
In 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 in a range of about 0.1 eV to about 1.0 eV; or 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 in a range of about 0.1 eV to about 1.0 eV, or 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 equal to or less than about 1.25 eV (e.g., in a range of 0.2 eV to about 1.25 eV) or 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 equal to or less than about 1.25 eV (e.g., in a range of about 0.2 eV to about 1.25 eV).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, a balance between holes and electrons injected into the emission layer may be achieved.
The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to a first embodiment, the organometallic compound may be included in an emission layer in the interlayer of a light-emitting device, wherein the emission layer may further include a host, the organometallic compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the organometallic compound. For example, according to the first embodiment, the organometallic compound may be a dopant or an emitter. In an embodiment, the organometallic compound may be a phosphorescent dopant or a phosphorescence emitter.
The phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may improve the luminescence efficiency from the organometallic compound by effectively transferring to the organometallic compound, which may be a dopant or an emitter.
The auxiliary dopant may be different from the organometallic compound and the host.
In an embodiment, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to a second embodiment, the organometallic compound may be included in an emission layer in the interlayer of a 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 each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
In an embodiment, the organometallic compound in the second embodiment may serve not as a dopant, but may serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In embodiments, the organometallic compound in the second embodiment may serve as an emitter and may also serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In embodiments, the 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., an organometallic compound represented by Formula 1 as described herein, an organometallic compound represented by Formula 401 as described herein, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501 as described herein, a compound represented by Formula 502 as described herein, a compound represented by Formula 503 as described herein, or any combination thereof).
In the first embodiment and the second embodiment, the blue light may have a maximum emission wavelength in a range of about 390 nm to about 500 nm. For example, the blue light in the first embodiment and the second embodiment may be blue light having a maximum emission wavelength in a range of about 410 nm to about 490 nm. For example, the blue light in the first embodiment and the second embodiment may be blue light having a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the blue light in the first embodiment and the second embodiment may be blue light having a maximum emission wavelength in a range of about 440 nm to about 475 nm. For example, the blue light in the first embodiment and the second embodiment may be blue light having a maximum emission wavelength in a range of about 455 nm to about 470 nm.
The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503 as described herein.
The host in the first embodiment and in the second embodiment may be any host material (e.g., the compound represented by Formula 301 as described herein, the compound represented by 301-1 as described herein, the compound represented by Formula 301-2 as described herein, or any combination thereof).
In embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
In embodiments, the light-emitting device may further include a capping layer arranged outside the first electrode and/or outside the second electrode.
In embodiments, the light-emitting device may further include at least one of a first capping layer arranged outside the first electrode and a second capping layer arranged outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer. Further details on the first capping layer and/or the second capping layer are the same as described herein.
In an embodiment, the light-emitting device may include:
The expression “(interlayer and/or capping layer) includes the organometallic compound represented by Formula 1” as used herein may be understood as “(interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds, each represented by Formula 1.”
In an embodiment, the interlayer and/or the capping layer may include Compound 1 only as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In embodiments, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
The term “interlayer” as used herein refers to a single layer and/or all layers between the first electrode and the second electrode of the light-emitting device.
Another embodiment provides an electronic apparatus which may include 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. The electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. Further details on the electronic apparatus are the same as described herein.
Another embodiment provides an electronic equipment which may include the light-emitting device.
In an embodiment, the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Another embodiment provides the organometallic compound which may be represented by Formula 1. Details on Formula 1 are the same as described herein.
Synthesis methods of the organometallic compound may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided below.
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 an embodiment, M may be Pt, Pd, or Au.
In an embodiment, M may be Pt.
In Formula 1, X1 may be C, and a bond between X1 and M may be a coordinate bond.
In an embodiment, X1 may be C of a carbene moiety.
In Formula 1, X2 to X4 may each independently be C or N.
In an embodiment, X2 and X3 may each be C, and
X4 may be N.
In an embodiment, one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may each be a coordinate bond, and the other two bonds may each be a covalent bond.
In an embodiment, a bond between X4 and M may be a coordinate bond, and
In an embodiment, X2 and X3 may each be C, and X4 may be N,
In Formula 1, ring CY1, ring CY2, ring CY31, ring CY32, and ring CY4 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In an embodiment, ring CY1, ring CY2, ring CY31, ring CY32, and ring CY4 may each independently be:
In an embodiment, ring CY1 may be an imidazole group, a triazole group, a benzimidazole group, a naphthoimidazole group, or an imidazopyridine group.
In an embodiment, ring CY2 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, or an azadinaphthosilole group.
In an embodiment, ring CY2 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In an embodiment, ring CY31 and ring CY32 may each independently be:
In an embodiment, ring CY4 may be a nitrogen-containing C1-C60 heterocyclic group.
In an embodiment, ring CY4 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a benzopyrazole group, a benzimidazole group, or a benzothiazole group.
In Formula 1, L1 to L3 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)—*′, wherein * and *′ each indicate a binding site to a neighboring atom.
In Formula 1, n1 to n3 indicate the number of L1 to the number of L3, respectively, and n1 to n3 may each independently be an integer from 1 to 10. When n1 is 2 or more, two or more of L1 may be identical to or different from each other, when n2 is 2 or more, two or more of L2 may be identical to or different from each other, and when n3 is 2 or more, two or more of L3 may be identical to or different from each other.
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-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
R10a and Q1 to Q3 are each the same as described herein.
In an embodiment, L1 and L3 may each be a single bond.
In an embodiment, L2 may be *—O—*′ or *—S—*′, and n2 may be 1.
In an embodiment, L1 and L3 may each be a single bond, and
L2 may be *—O—*′ or *—S—*′, and n2 may be 1.
In an embodiment, R1a and R1b may each independently be:
In Formula 1, R1, R11, R2, R31, R32, and R4 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
R10a and Q1 to Q3 are each the same as described herein.
In Formula 1, a1, a2, a31, a32, and a4 indicate the number of R1, the number of R2, the number of R31, the number of R32, and the number of R4, respectively, and a1, a2, a31, a32, and a4 may each independently be an integer from 1 to 20. When a1 is 2 or more, two or more of R1 may be identical to or different from each other, when a2 is 2 or more, two or more of R2 may be identical to or different from each other, when a31 is 2 or more, two or more of R31 may be identical to or different from each other, when a32 is 2 or more, two or more of R32 may be identical to or different from each other, and when a4 is 2 or more, two or more of R4 may be identical to or different from each other.
In an embodiment, R1, R11, R2, R31, R32, and R4 may each independently be:
In an embodiment, R1, R11, R2, R31, R32, and R4 may each independently be:
In an embodiment, R1, R11, R2, R31, R32, and R4 may each independently be:
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY1(1) to CY1 (11):
In Formulae CY1(1) to CY1(11),
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY2(1) to CY2(13):
In Formulae CY2(1) to CY2(13),
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY31(1) to CY31-(6):
In Formulae CY31(1) to CY31(6),
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY32(1) to CY32(16):
In Formulae CY32(1) to CY32(16),
*2 indicates a binding site to N in Formula 1, and
*3 indicates a binding site to ring CY31 in Formula 1.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY4(1) to CY4(29):
In Formulae CY4(1) to CY4(29),
In Formula 1, two or more neighboring groups among R1 in the number of a1, R11, R2 in the number of a2, R31 in the number of a31, R32 in the number of a32, R4 in the number of a4, R1a, and R1b may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and
R10a may be the same as described herein.
In Formula 1, two neighboring groups of R1 in the number of a1; two neighboring groups of R2 in the number of a2; two neighboring groups of R31 in the number of a31; two neighboring groups of R32 in the number of a32; or two neighboring groups of R4 in the number of a4 may optionally be bonded to each other to form a group represented by Formula 1A.
In an embodiment, the organometallic compound represented by Formula 1 may include at least one group represented by Formula 1A:
In Formula 1A, X51 may be C(R51) or N, X52 may be C(R52) or N, X53 may be C(R53) or N, X54 may be C(R54) or N, X55 may be C(R55) or N, X56 may be C(R56) or N, X57 may be C(R57) or N, and X58 may be C(R58) or N.
In Formula 1A, R51 to R58 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), and
R10a and Q1 to Q3 are each the same as described herein.
In an embodiment, X51 may be C(R51), X52 may be C(R52), X53 may be C(R53), X54 may be C(R54), X55 may be C(R55), X56 may be C(R56), X57 may be C(R57), and X58 may be C(R58).
In an embodiment, R51 to R58 may each independently be:
In an embodiment, R51 to R58 may each independently be:
In an embodiment, R51 to R58 may each independently be:
In Formula 1A, * and *′ each indicate a binding site to a neighboring atom.
In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1:
In Formula 1-1,
In an embodiment, the organometallic compound represented by Formula 1-1 may satisfy at least one of Conditions 1 to 12:
Unless defined otherwise, in Formulae 1 and 1A, R10a may be:
Unless defined otherwise, in Formulae 1 and 1A, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
The organometallic compound represented by Formula 1 may include at least one group represented by Formula 1A, and the group represented by Formula 1A may cause a steric protection effect in the molecule. Accordingly, by using the organometallic compound represented by Formula 1, an electronic device (e.g., an organic light-emitting device) having reduced driving voltage, improved color purity and efficiency, and increased lifespan may be implemented.
In Formula 2, L51 to L53 may each independently be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In Formula 2, b51 to b53 indicate the number of L51 to the number of L53, respectively, and b51 to b53 may each independently be an integer from 1 to 5. When b51 is 2 or more, two or more of L51 may be identical to or different from each other, when b52 is 2 or more, two or more of L52 may be identical to or different from each other, and when b53 is 2 or more, two or more of L53 may be identical to or different from each other. In an embodiment, b51 to b53 may each independently be 1 or 2.
In an embodiment, in Formula 2, L51 to L53 may each independently be:
In an embodiment, 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 of L51, a bond between two or more of L52, a bond between two or more of L53, a bond between L51 and carbon between X54 and X55, a bond between L52 and carbon between X54 and X56, and a bond between L53 and carbon between X55 and X56 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 each be N. In Formula 2, R54 to R56 may each be the same as described herein. For example, two or three of X54 to X56 may each be N.
In Formula 2, R51 to R56 may each independently be hydrogen, deuterium, —F, —C1, —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 are each the same as described herein.
In an embodiment, in Formula 2, R51 to R56 may each independently be:
In Formula 91,
In an embodiment, in Formula 91,
In an embodiment, 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 an embodiment, in Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may be identical to each other.
In embodiments, in Formula 2, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may be different from each other.
In embodiments, in Formula 2, b51 and b52 may each independently 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 an embodiment, in Formula 2, R51 and R52 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
Q1 to Q3 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In an embodiment, in Formula 2,
In Formulae CY51-1 to CY51-26, CY52-1 to CY52-26, and CY53-1 to CY53-27,
In Formulae CY51-16 and CY51-17, Y63 may be O or S and Y64 may be Si(R64a)(R64b), or Yes may be Si(R63a)(R63b) and Y64 may be O or S, and
in Formulae CY52-16 and CY52-17, Y67 may be O or S and Yes may be Si(R63a)(R64b), or Y67 may be Si(R67a)(R67b) and Yes may be O or S.
In Formula 3, ring CY71 and ring CY72 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group.
In Formula 3, X71 may be: a single bond; or a linking group including O, S, N, B, C, Si, or any combination thereof.
In Formula 3, * indicates a binding site to any atom in a remaining portion of the third compound other than the group represented by Formula 3.
In Formulae 3-1 to 3-5, ring CY71 to ring CY74 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group.
In Formulae 3-1 to 3-5, X82 may be a single bond, O, S, N-[(L82)b82-R82], C(R82a)(R82b), or Si(R82a)(R82b).
In Formulae 3-1 to 3-5, X83 may be a single bond, O, S, N-[(L83)b83-R83], C(R83a)(R83b), or Si(R83a)(R83b).
In Formulae 3-1 to 3-5, X84 may be O, S, N-[(L84)b84-R84], C(R84a)(R84b), or Si(R84a)(R84b).
In Formulae 3-1 to 3-5, X85 may be C or Si.
In Formulae 3-1 to 3-5, L81 to L85 may each independently be a single bond, *—C(Q4)(Q5)-*′, *—Si(Q4)(Q5)-*′, a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R10a, or a pyridine group unsubstituted or substituted with at least one R10a, and
Q4 and Q5 may each independently be the same as described in connection with Q1.
In Formulae 3-1 to 3-5, b81 to b85 may each independently be an integer from 1 to 5.
In Formulae 3-1 to 3-5, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b may each be the same as described herein.
In Formulae 3-1 to 3-5, a71 to a74 indicate the number of R71 to the number of R74, respectively, and a71 to a74 may each independently be an integer from 0 to 20. When a71 is 2 or more, two or more of R71 may be identical to or different from each other, when a72 is 2 or more, two or more of R72 may be identical to or different from each other, when a73 is 2 or more, two or more of R73 may be identical to or different from each other, and when a74 is 2 or more, two or more of R74 may be identical to or different from each other. In an embodiment, a71 to a74 may each independently be an integer from 0 to 8.
In Formulae 3-1 to 3-5, R10a may be the same as described herein.
In an embodiment, in Formulae 3-1 to 3-5, L81 to L85 may each independently be:
*—C(Q4)(Q)-*′ or *—Si(Q4)(Q5)-*′; or
In embodiments, a moiety represented by
in Formulae 3-1 and 3-2 may be a moiety represented by one of Formulae CY71-1(1) to CY71-1(8), and/or
in Formulae 3-1 and 3-3 may be a moiety represented by one of Formulae CY71-2(1) to CY71-2(8), and/or
in Formulae 3-2 and 3-4 may be a moiety represented by one of Formulae CY71-3(1) to CY71-3(32), and/or
in Formulae 3-3 to 3-5 may be a moiety represented by one of Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 3-5 may be a moiety represented by one of Formulae CY71-5(1) to CY71-5(8):
In Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
In Formulae 502 and 503, ring A501 to ring A504 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
In Formulae 502 and 503, Y505 may be O, S, N(R505), B(R505), C(R505a)(R505b), or Si(R505a)(R505b).
In Formulae 502 and 503, Y506 may be O, S, N(R506), B(R506), C(R506a)(R506b), or Si(R506a)(R506b).
In Formulae 502 and 503, Y507 may be O, S, N(R507), B(R507), C(R507a)(R507b), or Si(R507a)(R507b).
In Formulae 502 and 503, Y508 may be O, S, N(R508), B(R508), C(R508a)(R508b), or Si(R508a)(R508b).
In Formulae 502 and 503, Y51 and Y52 may each independently be B, P(═O), or S(═O).
In Formulae 502 and 503, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b may each be the same as described herein.
In Formulae 502 and 503, a501 to a504 indicate the number of R501 to the number of R504, respectively, and a501 to a504 may each independently be an integer from 0 to 20. When a501 is 2 or more, two or more of R501 may be identical to or different from each other, when a502 is 2 or more, two or more of R502 may be identical to or different from each other, when a503 is 2 or more, two or more of R503 may be identical to or different from each other, and when a504 is 2 or more, two or more of R504 may be identical to or different from each other. In an embodiment, a501 to a504 may each independently be an integer from 0 to 8.
In the specification, in Formulae 2, 3-1 to 3-5, 502, and 503, 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 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 heteroaryl alkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1 to Q3 may each be the same as described herein.
In an embodiment, 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 R10a may each independently be:
In embodiments, R1, R11, R2, R31, R32, and R4 in Formula 1 and R51 to R58 in Formula 1A; 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 R10a may each independently be:
In Formulae 9-1 to 9-19 and 10-1 to 10-246, * indicates a binding site to a neighboring atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.
In an embodiment, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 52:
Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described 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 the injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In 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 (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer 130 is arranged on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, or the like.
In an embodiment, the interlayer 130 may include two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one a charge generation layer arranged between the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the at least one charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple 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 any combination thereof.
In an embodiment, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in its respective stated order, but the structure of the hole transport region is not limited thereto.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each independently be the same as described in connection with R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a.
In an embodiment, in Formulae CY201 to CY217, ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of groups represented by Formulae CY201 to CY203.
In embodiments, the compound represented by Formula 201 may include at least one of groups represented by Formulae CY201 to CY203 and at least one of groups represented by Formulae CY204 to CY217.
In 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 embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY203.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulae CY201 to CY203, and may each independently include at least one of the groups represented by Formulae CY204 to CY217.
In embodiments, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include a group represented by one of Formulae CY201 to CY217.
In an embodiment, the hole transport region may include: one of 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); or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the ranges described above, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer may block 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 the materials described above, 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 (e.g., in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be less than or equal to about −3.5 eV.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of a quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of a cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Examples of a metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., 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 (e.g., zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (e.g., 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 the like.
Examples of a metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Examples of a non-metal may include oxygen (O), a halogen (e.g., F, Cl, Br, I, etc.), and the like.
Examples of a compound including element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
Examples of a metal oxide may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (e.g., ReO3, etc.), and the like.
Examples of a metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and the like.
Examples of an alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
Examples of an alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and the like.
Examples of a transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (e.g., HfF4, HfC14, HfBr4, HfI4, etc.), a vanadium halide (e.g., VF3, VCl3, VBr3, VI3, etc.), a niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (e.g., CrF3, CrO3, CrBr3, CrI3, etc.), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), a manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and the like.
Examples of a post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, Zn12, etc.), an indium halide (e.g., InI3, etc.), a tin halide (e.g., SnI2, etc.), and the like.
Examples of a lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
Examples of a metalloid halide may include an antimony halide (e.g., SbCl5, etc.) and the like.
Examples of a metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (e.g., 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.), a post-transition metal telluride (e.g., ZnTe, etc.), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In an embodiment, 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 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 an embodiment, the emission layer may include a host and a dopant (or emitter). In an embodiment, 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 may be different from each other.
The organometallic compound represented by Formula 1 described herein may serve as the dopant (or emitter), or may serve as the auxiliary dopant.
An amount (weight) of the dopant (or emitter) in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
The emission layer may include the organometallic compound represented by Formula 1. An amount (weight) of the organometallic compound in the emission layer may be in a range of about 0.01 parts by weight to about 30 parts by weight, based on 100 parts by weight of the emission layer. For example, the amount (weight) of the organometallic compound in the emission layer may be in a range of about 0.1 parts by weight to about 20 parts by weight, based on 100 parts by weight of the emission layer. For example, the amount (weight) of the organometallic compound in the emission layer may be in a range of about 0.1 parts by weight to about 15 parts by weight, based on 100 parts by weight of the emission layer.
In embodiments, the emission layer may include a quantum dot.
In embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or as a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer is within the ranges described above, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host in the emission layer may include the second compound or the third compound described herein, or any combination thereof.
In an embodiment, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 [Formula 301]
In Formula 301,
In an embodiment, in Formula 301, when xb11 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.
In embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In Formulae 301-1 and 301-2,
In embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., Compound H55), a Mg complex, a Zn complex, or any combination thereof.
In embodiments, the host may include one of Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
In embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
The host may have various 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 described herein.
In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In Formulae 401 and 402,
In an embodiment, in Formula 402, X401 may be nitrogen and X402 may be carbon, or each of X401 and X402 may be nitrogen.
In embodiments, when xc1 in Formula 401 is 2 or more, two of ring A401 among two or more of L401 may optionally be linked to each other via T402, which is a linking group, and two of ring A402 among two or more of L401 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). For example, T402 and T403 may each independently be the same as described in connection with T401.
In Formula 401, L402 may be an organic ligand. In an embodiment, L402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:
When the emission layer includes the organometallic compound represented by Formula 1 described herein and the organometallic compound represented by Formula 1 serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 described herein and the organometallic compound represented by Formula 1 serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
In Formula 501,
In an embodiment, in Formula 501, Ar501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed with each other.
In embodiments, in Formula 501, xd4 in Formula 501 may be 2.
In an embodiment, the fluorescent dopant and the auxiliary dopant may each include one of Compounds FD1 to FD37, DPVBi, DPAVB, or any combination thereof:
The emission layer may include a delayed fluorescence material.
The delayed fluorescence material described herein may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material may include, for example, the fourth compound described herein.
The delayed fluorescence material included in the emission layer may serve as a host or as a dopant, depending on the types of other materials included in the emission layer.
In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be in a range of about 0 eV to about 0.5 eV. When a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material satisfies within the range described above, up-conversion from the triplet state to the singlet state of the delayed fluorescence material may effectively occur, and thus, the light-emitting device 10 may have improved luminescence efficiency.
In an embodiment, the delayed fluorescence material may include a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, etc.); or a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B); or the like.
Examples of a delayed fluorescence material may include at least one of Compounds DF1 to DF14:
The emission layer may include a quantum dot.
In the specification, a quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to a size of the crystal.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method that includes mixing a precursor material with an organic solvent and growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally serves as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a process which costs less, and may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.
Examples of a Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and the like; or any combination thereof.
Examples of a Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and the like; or any combination thereof. In an embodiment, the Group Ill-V semiconductor compound may further include a Group II element. Examples of a Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of a Group Ill-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and the like; a ternary compound, such as InGaS3, InGaSe3, and the like; or any combination thereof.
Examples of a Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, and the like; or any combination thereof.
Examples of a Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and the like; or any combination thereof.
Examples of a Group IV element or compound may include: a single element material, such as Si, Ge, and the like; a binary compound, such as SiC, SiGe, and the like; or any combination thereof.
Each element included in a multi-element compound, such as a binary compound, a ternary compound, or a quaternary compound, may be present in a particle at a uniform concentration or at a non-uniform concentration.
In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell dual structure. In an embodiment, in case that the quantum dot has a core-shell structure, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may serve as a protective layer that prevents chemical denaturation of the core to maintain semiconductor characteristics, and/or may serve as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be single-layered or multi-layered. An interface between the core and the shell may have a concentration gradient in which the concentration of a material that is present in the shell decreases toward the core.
Examples of a shell of the quantum dot may include a metal oxide, a metalloid oxide, or a non-metal oxide, a semiconductor compound, or any combination thereof.
Examples of a metal oxide, a metalloid oxide, or a non-metal oxide may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, and the like; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, and the like; or any combination thereof.
Examples of a semiconductor compound may include, as described herein, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. Examples of a semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 30 nm. When the FWHM of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. Light emitted through a quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
In embodiments, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, a nanoplate particle, or the like.
Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various wavelength bands may be obtained from a quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In detail, the size of the quantum dot may be selected to emit red light, green light, and/or blue light. In an embodiment, the size of the quantum dot may be configured to emit white light by a combination of light of various colors.
The electron transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple layers including different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the layers of each structure may be stacked from an emission layer in its respective stated order, but the structure of the electron transport region is not limited thereto.
The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
In an embodiment, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 [Formula 601]
In Formula 601,
In an embodiment, in Formula 601, when xe11 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.
In embodiments, in Formula 601, Ar601 may be a substituted or unsubstituted anthracene group.
In embodiments, the electron transport region may include a compound represented by Formula 601-1:
In Formula 601-1,
In an embodiment, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In embodiments, the electron transport region may include: one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å. For example, the thickness of the electron transport region may be in a range of about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within the ranges described above, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (e.g., an electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion.
A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or Compound 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 contact (e.g., directly contact) the second electrode 150.
The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials that are different from each other, or a structure including multiple layers including multiple materials including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
Examples of an alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
Examples of an alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
Examples of an alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, K2O, and the like; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI, and the like; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), and the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and the like.
Examples of an alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include one of metal ions of the alkali metal, the alkaline earth metal, and the rare earth metal, and as a ligand bonded to the metal ions, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In an embodiment, the electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (e.g., alkali metal halide), an alkali metal-containing compound (e.g., alkali metal halide); and an alkali metal, an alkaline earth metal, a rare earth metal, or any 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 the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be 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. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the interlayer 130 having a structure as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.
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 any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure.
A first capping layer may be arranged outside the first electrode 110, and/or a second capping layer may be arranged outside the second electrode 150. In detail, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in 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 may be sequentially stacked in the stated order.
Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first capping layer. Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and through the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In embodiments, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In embodiments, at least one of the first capping layer and the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
The organometallic compound represented by Formula 1 may be included in various films. Accordingly, another embodiment provides a film which may include the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control means) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflective layer, a light absorbing layer, etc.), a protective member (e.g., an insulating layer, a dielectric layer, etc.), or the like.
The light-emitting device may be included in various electronic apparatuses. In embodiments, an electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light-emitting device. In embodiments, the light emitted from the light-emitting device may be blue light, green light, or white light. The light-emitting device may be the same as described herein. In an embodiment, the color conversion layer may include a quantum dot.
The electronic apparatus may include a first substrate. The first substrate may include subpixels, the color filter may include color filter areas respectively corresponding to the subpixels, and the color conversion layer may include color conversion areas respectively corresponding to the subpixels.
A pixel defining layer may be arranged between the subpixels to define each subpixel.
The color filter may further include color filter areas and light-shielding patterns arranged between the color filter areas, and the color conversion layer may further include color conversion areas and light-shielding patterns arranged between the color conversion areas.
The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. 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 color filter areas (or the color conversion areas) may include quantum dots. For example, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. The quantum dot may be a quantum dot as described herein. The first area, the second area, and/or the third area may each further include a scatterer.
In an embodiment, the light-emitting device may emit first light, the first area may absorb the first light to emit a first-first color light, the second area may absorb the first light to emit a second-first color light, and the third area may absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from another. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The 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 the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion may allow light from the light-emitting device to be extracted to the outside, and may simultaneously prevent ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
Various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of functional layers may include a touch screen layer, a polarizing layer, and 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 using biometric information of a living body (e.g., 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 various displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, or the like.
The light-emitting device may be included in various electronic equipment.
In an embodiment, the electronic equipment including the light-emitting device may be one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a 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 display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
The light-emitting device may have excellent luminescence efficiency and long lifespan, and thus the electronic equipment including the light-emitting device may have characteristics such as high luminance, high resolution, and low power consumption.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be arranged on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be arranged 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 arranged on the activation layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate from one another.
The source electrode 260 and the drain electrode 270 may be arranged 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 respectively contact 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 may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel defining layer 290 may expose a selected 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-based organic film or a polyacrylic-based organic film. Although not shown in
The second electrode 150 may be arranged 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 arranged on the second capping layer 170. The encapsulation portion 300 may be arranged 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, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of the inorganic films and the organic films.
The light-emitting apparatus of
The electronic equipment 1, which may be an apparatus that displays a moving image or still image, may be not only a portable electronic equipment, such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation device, a ultra-mobile PC (UMPC), but may also be various products, such as a television, a laptop computer, a monitor, a billboard, or an Internet of things (IoT). The electronic equipment 1 may be such a product as described above or a part thereof.
In an embodiment, the electronic equipment 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type display, or a head mounted display (HMD), or a part of the wearable device. However, embodiments are not limited thereto.
For example, the electronic equipment 1 may be a dashboard of a vehicle, a center fascia of a vehicle, a center information display (CID) arranged on a dashboard of a vehicle, a room mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display arranged on the back of a front seat, a head up display (HUD) installed in the front of a vehicle or projected on a front window glass, or a computer-generated hologram augmented-reality head up display (CGH AR HUD). For convenience of explanation,
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 a two-dimensional array of pixels that are arranged in the display area DA.
The non-display area NDA is an area that does not display an image, and may surround the display area DA. A driver for providing electrical signals or power to display devices arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
In the electronic equipment 1, a length in an x-axis direction and a length in a y-axis direction may be different from each other. In an embodiment, as shown in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a given direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, 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 that is a portion excluding the body in which mechanical apparatuses necessary for driving are installed. The exterior of the vehicle body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and 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, rear, left, and right wheels, and the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed in a door of the vehicle 1000. Multiple side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in an x-direction or in a −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 in the −x-direction. An virtual straight line L connecting the side window glasses 1100 may extend in the x-direction or in the ※ direction. For example, the virtual 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 in the −x-direction.
The front window glass 1200 may be installed on 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 an embodiment, multiple side mirrors 1300 may be provided. Any one of side mirrors 1300 may be arranged outside the first side window glass 1110. Another one of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of a steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning lamp, an odometer, a driving record system, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center fascia 1500 may be arranged on a side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400, with the center fascia 1500 arranged between the passenger seat dashboard 1600 and the cluster 1400. In an embodiment, the cluster 1400 may be arranged to correspond to a driver seat (not shown), and the passenger seat dashboard 1600 may be arranged to correspond to a passenger seat (not shown). In an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In an embodiment, the display 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 an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged in at least one of 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 light-emitting display device, a quantum dot display device, or the like. Hereinafter, as the display device 2 according to an embodiment of the disclosure, an organic light-emitting display device including the light-emitting device according to the disclosure will be described as an example, but various types of display devices as described herein may be used as embodiments.
Referring to
Referring to
Referring to
The layers constituting a hole transport region, an emission layer, and the layers constituting an electron transport region may be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and the like.
When the layers constituting a hole transport region, the emission layer, and the layers constituting an electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10-3 torr, and at a deposition speed in a range of about 0.01 Å/see to about 100 Å/see, 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 used herein may be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having 3 to 60 carbon atoms, and the term “C1-C60 heterocyclic group” as used herein may be a cyclic group that has 1 to 60 carbon atoms and further has, in addition to a carbon atom, at least one 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 number of ring-forming atoms of a C1-C60 heterocyclic group may be from 3 to 61.
The term “cyclic group” as used herein may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used herein may be a cyclic group that has 3 to 60 carbon atoms and may not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as used herein may be to a heterocyclic group that has 1 to 60 carbon atoms and may include *—N═*′ as a ring-forming moiety.
The terms “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, or “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of a monovalent C3-C60 carbocyclic group or a 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 a divalent C3-C60 carbocyclic group or a divalent C1-C60 heterocyclic group are a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and the like. The term “C1-C60 alkylene group” as used herein may be a divalent group having a same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at a terminus of a C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, or the like. The term “C2-C60 alkenylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at a terminus of a C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and the like. The term “C2-C60 alkynylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein may be a monovalent group represented by —O(A101) (wherein A101 may be a C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
The term “C3-C10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, or the like. The term “C3-C10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkyl group.
The term “C1-C1 heterocycloalkyl group” as used herein may be 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 examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein may be 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-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkenylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of a C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the respective rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein may be 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 used herein may be 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 a C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, and the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the respective rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein may be a monovalent group (e.g., 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 a monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indeno anthracenyl group, and the like. The term “divalent non-aromatic condensed polycyclic group” as used herein may be to a divalent group having a same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group (e.g., 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 a monovalent non-aromatic condensed heteropolycyclic group may 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, a benzothienodibenzothiophenyl group, and the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein may be a group represented by to —O(A102) (wherein A102 may be a C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein may be a group represented by —S(A103) (wherein A103 may be a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein may be a group represented by -(A104)(A105) (wherein A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as used herein may be a group represented by -(A106)(A107) (wherein A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
In the specification, the group “R10a” may be:
In the specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 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; a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
The term “heteroatom” as used herein may be to any atom other than a carbon atom or a hydrogen atom. Examples of a heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), or the like.
In the specification, the term “Ph” refers to a phenyl group, the term “Me” refers to a methyl group, the term “Et” refers to an ethyl group, the terms “ter-Bu” or “But” each refer to a tert-butyl group, and the term “OMe” refers to a methoxy group.
The term “biphenyl group” as used herein may be a “phenyl group substituted with a phenyl group.” For example, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein may be a “phenyl group substituted with a biphenyl group.” For example, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
The symbols *, *′, *″, *′″, *2, and *3 as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
In the specification, the terms “x-axis”, “y-axis”, and “z-axis” are not limited to three axes in an orthogonal coordinate system (for example, a Cartesian coordinate system), and may be interpreted in a broader sense than the aforementioned three axes in an orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may be axes that are orthogonal to each other, or may be axes that are in different directions that are not orthogonal to each other.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
2-bromo-3-nitro-9,10-dihydro-9,10-[1,2]benzenoanthracene (2 eq), 2-methylpropan-2-amine (1 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos) (0.10 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.05 eq), and sodium tert-butoxide (NaOtBu) (3 eq) were dissolved in toluene, stirred at 110° C. for 24 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using methylene chloride (MC) and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 2-1 (yield: 77%).
Intermediate 2-1 (1 eq) and tin (5 eq) were dissolved in ethanol (EtOH), and stirred. After adding hydrogen chloride (12 M) thereto, the resultant reaction mixture was stirred at 80° C. for 6 hours, and cooled to room temperature. The reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 2-2 (yield: 80%).
Intermediate 2-2 (1 eq), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1 eq), Pd2(dba)3 (0.05 eq), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (0.10 eq), and NaOtBu (2 eq) were dissolved in toluene (0.1 M), stirred at 110° C. for 2 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 2-3 (yield: 75%).
Intermediate 2-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% deuterium chloride (DCI) (1.5 eq) was added thereto. The resultant reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove the triethyl orthoformate therefrom. The reaction mixture was subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:methanol) to thereby synthesize Intermediate 2-4 (yield: 84%).
Intermediate 2-4 (1 eq), potassium platinum(II) chloride (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120° C. for 18 hours in the nitrogen condition, and cooled to room temperature. The resultant reaction mixture was concentrated to remove the 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to an extraction process three times using dichloromethane and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Compound 2 (yield: 50%).
ESI-LCMS: [M]+: C52H43N4OPt, 934.3
1-bromo-2-nitrobenzene (2 eq), aniline (1 eq), Sphos (0.10 eq), Pd2(dba)3 (0.05 eq), and NaOtBu (3 eq) were dissolved in toluene, stirred at 110° C. for 24 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 16-1 (yield: 84%).
Intermediate 16-1 (1 eq) and tin (5 eq) were dissolved in EtOH, and stirred. After adding hydrogen chloride (12 M) thereto, the resultant reaction mixture was stirred at 80° C. for 6 hours, and cooled to room temperature. The reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 16-2 (yield: 82%).
Intermediate 16-2 (1 eq), (9s,10s)-12-(2-(3-bromophenoxy)-9H-carbazol-9-yl)-9,10-dihydro-9,10-[3,4]pyridinoanthracene (1 eq), Pd2(dba)3 (0.05 eq), Xphos (0.10 eq), and NaOtBu (2 eq) were dissolved in toluene (0.1 M), stirred at 110° C. for 2 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 16-3 (yield: 75%).
Intermediate 16-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCI (1.5 eq) was added thereto. The resultant reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove the triethyl orthoformate therefrom. The reaction mixture was subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:methanol) to thereby synthesize Intermediate 16-4 (yield: 81%).
Intermediate 16-4 (1 eq), potassium platinum(II) chloride (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120° C. for 18 hours in the nitrogen condition, and cooled to room temperature. The resultant reaction mixture was concentrated to remove the 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to an extraction process three times using dichloromethane and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Compound 16 (yield: 51%).
ESI-LCMS: [M]+: C50H31N4OPt, 898.2
1-bromo-2-nitrobenzene (2 eq), [1,1′:3′,1″-terphenyl]-2,2″,3,3″,4,4″,5,5″,6,6″-d10-2′-amine (1 eq), Sphos (0.10 eq), Pd2(dba)3 (0.05 eq), and NaOtBu (3 eq) were dissolved in toluene, stirred at 110° C. for 24 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 38-1 (yield: 82%).
Intermediate 38-1 (1 eq) and tin (5 eq) were dissolved in EtOH, and stirred. After adding hydrogen chloride (12 M) thereto, the resultant reaction mixture was stirred at 80° C. for 6 hours, and cooled to room temperature. The reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 38-2 (yield: 81%).
Intermediate 38-2 (1 eq), 7-(3-bromophenoxy)-5-(4-(tert-butyl)pyridin-2-yl)-8,13-dihydro-5H-8,13-[1,2]benzenonaphtho[2,3-c]carbazole-9,10,11,12,16,17,18,19-d8 (1 eq), Pd2(dba)3 (0.05 eq), Xphos (0.10 eq), and NaOtBu (2 eq) were dissolved in toluene (0.1 M), stirred at 110° C. for 2 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 38-3 (yield: 73%).
Intermediate 38-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCI (1.5 eq) was added thereto. The resultant reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove the triethyl orthoformate therefrom. The reaction mixture was subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:methanol) to thereby synthesize Intermediate 38-4 (yield: 77%).
Intermediate 38-4 (1 eq), potassium platinum(II) chloride (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120° C. for 18 hours in the nitrogen condition, and cooled to room temperature. The resultant reaction mixture was concentrated to remove the 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to an extraction process three times using dichloromethane and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Compound 38 (yield: 49%).
ESI-LCMS: [M]+: C66H29D18N4OPt, 1124.5
1-bromo-2-nitrobenzene (2 eq), methan-d3-amine (1 eq), Sphos (0.10 eq), Pd2(dba)3 (0.05 eq), and NaOtBu (3 eq) were dissolved in toluene, stirred at 110° C. for 24 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 47-1 (yield: 83%).
Intermediate 47-1 (1 eq) and tin (5 eq) were dissolved in EtOH, and stirred. After adding hydrogen chloride (12 M) thereto, the resultant reaction mixture was stirred at 80° C. for 6 hours, and cooled to room temperature. The reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 47-2 (yield: 82%).
Intermediate 47-2 (1 eq), 2-((4-bromo-9,10-dihydro-9,10-[1,2]benzenoanthracen-2-yl)oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1 eq), Pd2(dba)3 (0.05 eq), Xphos (0.10 eq), and NaOtBu (2 eq) were dissolved in toluene (0.1 M), stirred at 110° C. for 2 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 47-3 (yield: 74%).
Intermediate 47-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCI (1.5 eq) was added thereto. The resultant reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove the triethyl orthoformate therefrom. The reaction mixture was subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:methanol) to thereby synthesize Intermediate 47-4 (yield: 78%).
Intermediate 47-4 (1 eq), potassium platinum(II) chloride (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120° C. for 18 hours in the nitrogen condition, and cooled to room temperature. The resultant reaction mixture was concentrated to remove the 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to an extraction process three times using dichloromethane and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Compound 47(yield: 50%).
ESI-LCMS: [M]+: C49H34D3N4OPt, 895.3
1-bromo-2-nitrobenzene (2 eq), 9,10-dihydro-9,10-[1,2]benzenoanthracen-1-amine (1 eq), Sphos (0.10 eq), Pd2(dba)3 (0.05 eq), and NaOtBu (3 eq) were dissolved in toluene, stirred at 110° C. for 24 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 49-1 (yield: 79%).
Intermediate 49-1 (1 eq) and tin (5 eq) were dissolved in EtOH, and stirred. After adding hydrogen chloride (12 M) thereto, the resultant reaction mixture was stirred at 80° C. for 6 hours, and cooled to room temperature. The reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 49-2 (yield: 80%).
Intermediate 49-2 (1 eq), (7r,12r)-3-(3-bromophenoxy)-5-(4-(tert-butyl)pyridin-2-yl)-7,12-dihydro-5H-7,12-[1,2]benzenonaphtho[2,3-b]carbazole (1 eq), Pd2(dba)3 (0.05 eq), Xphos (0.10 eq), and NaOtBu (2 eq) were dissolved in toluene (0.1 M), stirred at 110° C. for 2 hours, and cooled to room temperature. The resultant reaction mixture was distilled under reduced pressure of 8 mbar to remove the solvent therefrom, and subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Intermediate 49-3 (yield: 72%).
Intermediate 49-3 (1 eq) was dissolved in triethyl orthoformate (30 eq), and 37% DCI (1.5 eq) was added thereto. The resultant reaction mixture was stirred at 80° C. for 24 hours, cooled to room temperature, and concentrated to remove the triethyl orthoformate therefrom. The reaction mixture was subjected to an extraction process three times using MC and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:methanol) to thereby synthesize Intermediate 49-4 (yield: 75%).
Intermediate 49-4 (1 eq), potassium platinum(II) chloride (1.1 eq), and 2,6-lutidine (4.0 eq) were dissolved in 1,2-dichlorobenzene (0.05 M), stirred at 120° C. for 18 hours in the nitrogen condition, and cooled to room temperature. The resultant reaction mixture was concentrated to remove the 1,2-dichlorobenzene therefrom. The reaction mixture was subjected to an extraction process three times using dichloromethane and water. The resultant organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography (MC:hexane) to thereby synthesize Compound 49 (yield: 50%).
ESI-LCMS: [M]+: C68H47N4OPt, 1130.4
MS/FAB of the compounds synthesized according to Synthesis Examples are shown in Table 1. Synthesis methods of compounds other than the compounds synthesized in Synthesis Examples may be readily recognized by those skilled in the art by referring to the synthesis paths and source materials.
The HOMO energy level (EHOMO), LUMO energy level (ELUMO), HOMO-LUMO band gap energy (Eg), T1 energy level (nm), and existence ratio (%) of a triplet metal-to-ligand charge transfer state (3MLCT) of each of Compounds 2, 16, 38, 47, and 49 and Compounds CE1 to CE5 were evaluated using the density functional theory (DFT) method of the Gaussian program, which was structure-optimized at the B3LYP/6-311 G(d,p) level, and results thereof are shown in Table 2.
3MLCT (%)
As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2 (1,200 Å) ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated by using isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and mounted on a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å. 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Compound 2, Compound DFD29, Compound HTH29, and Compound ETH2 were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 350 Å. In this regard, the amount of Compound 2 was 13 parts by weight based on 100 parts by weight of the emission layer, and the amount of Compound DFD29 was 0.4 parts by weight based on 100 parts by weight of the emission layer. The weight ratio of Compound HTH29 to Compound ETH2 was 6.5:3.5.
Compound HBL-1 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å.
CNNPTRZ and LiQ were vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 310 Å. In this regard, the weight ratio of CNNPTRZ to LiQ was 4:6.
Yb was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 15 Å.
Mg was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 800 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds used in forming an emission layer were changed as shown in Table 3.
The driving voltage (V) at 1,000 cd/m2, luminescence efficiency (cd/A), maximum emission wavelength (nm), and lifespan (T95) of each of the organic light-emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 5 were measured using Keithley MU 236 and luminance meter PR650, and results thereof are shown in Table 3. In this regard, the lifespan (T95) is a measure of the time (hr) taken until the luminance declines to 95% of the initial luminance, and the lifespan ratio represents the ratio (%) of the lifespan of each Example relative to the lifespan (T95) of Comparative Example 1 of 100.
From Table 3, it was confirmed that the organic light-emitting devices according to Examples 1 to 5 emitted blue light and had superior driving voltage, luminescence efficiency, and device lifespan compared to the organic light-emitting devices according to Comparative Examples 1 to 5.
According to the embodiments, by using an organometallic compound, a light-emitting device having reduced driving voltage, improved color purity and efficiency, and increased lifespan, and a high-quality electronic apparatus including the light-emitting device may be manufactured.
Embodiments have been disclosed herein, and although terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for the purposes of limitation. In some instances, as would be apparent by one of ordinary skill in the art, features, characteristics, and/or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made without departing from the spirit and scope of the disclosure as set forth in the claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0148439 | Oct 2023 | KR | national |
