Patent Application
20240196731
This application claims priority to and benefits of Korean Patent Application No. 10-2022-0143946 under 35 U.S.C. § 119, filed on Nov. 1, 2022, 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.
Self-emissive devices among light-emitting devices 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 disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in such an emission layer region to produce excitons. These excitons transition from an excited state to a ground state to 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 include a light-emitting device including an organometallic compound, an electronic apparatus including the same, and an organometallic compound.
Additional aspects will be set forth in part in the description, which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to embodiments, an organometallic compound may be represented by Formula 1:
In an embodiment, M may be Pt or Pd.
In an embodiment, L41 and L42 may each independently be *—C(R5)(R6)—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, or *—C≡C—*.
In an embodiment, rings CY1 to CY4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by Formula CY1-1, which is explained below.
In an embodiment, in Formula 1, a moiety represented by may be a moiety represented by Formula CY2-1, which is explained below.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY3(1) to CY3(20), which are explained below.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY4(1) to CY4(3), which are explained below.
In an embodiment, the organometallic compound may be represented by one of Formulae 1-1 to 1-6, which are explained below.
In an embodiment, the organometallic compound may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 475 nm.
In an embodiment, the organometallic compound may be one of Compounds BD1 to BD120, which are explained below.
Embodiments provide a light-emitting device which may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode, the interlayer comprising an emission layer, and an organometallic compound represented by Formula 1, which is explained herein.
In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode; 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; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
In an embodiment, the emission layer may include the organometallic compound represented by Formula 1.
In an embodiment, the emission layer may include a host and a dopant; and the dopant may include the organometallic compound represented by Formula 1.
In an embodiment, the emission layer may emit blue light; and the blue light may have a maximum emission wavelength in a range of about 430 nm to about 475 nm.
In an embodiment, an electronic apparatus may include the light-emitting device.
In an embodiment, the electronic apparatus may include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
In an embodiment, an electronic device may include the light-emitting device.
In an embodiment the electronic apparatus 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 portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality 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.
It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purpose of limitation, and the disclosure is not limited to the embodiments described above.
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 numbers and characters refer to like elements throughout.
In the description, 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 description, 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.
When an embodiment is implemented in a different manner, a process order may be performed differently than what is described herein. For example, two processes described in succession may be performed substantially simultaneously, or they may be performed in an order opposite to the described order.
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.
According to an embodiment, an organometallic compound may be represented by Formula 1:
In an embodiment, M may be Pt or Pd.
In an embodiment, L41 and L42 may each independently be *—C(R5)(R6)—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, or *—C≡C—*′.
In an embodiment, L41 and L42 may each independently be *—C(R5)(R6)—*′, and n41 and n42 may each independently be an integer from 2 to 5.
In an embodiment, R5 and R6 may each independently be hydrogen, deuterium, or a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a.
In an embodiment, rings CY1 to CY4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, X1 may be N.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by Formula CY1-1:
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY1 (1) to CY1(15):
In Formulae CY1 (1) to CY1 (15),
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by Formula CY2-1:
In Formula CY2-1,
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY3(1) to CY3(20):
In Formulae CY3(1) to CY3(20),
In an embodiment, X41 and X43 to X45 may each be C.
In an embodiment, ring CY4 may be a benzene group.
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae CY4(1) to CY4(3):
In Formulae CY4(1) to CY4(3),
In an embodiment, the organometallic compound may be represented by one of Formulae 1-1 to 1-6:
In Formulae 1-1 and 1-6,
M, ring CY1 to CY4, X1 to X3, X41 to X45, L1 to L3, L41, L42, n1 to n3, n41, n42, R1 to R4, and a1 to a4 may be the same as described in Formula 1.
In an embodiment, L2 may be *—O—*′.
In an embodiment, the organometallic compound may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 475 nm.
In an embodiment, the organometallic compound may be one of Compounds BD1 to BD120:
The organometallic compound represented by Formula 1 includes nitrogen (N)-heterocyclic carbene (NHC) in the form of imidazole, to which pyridine or the like is bonded. Therefore, the inductive effect of a substituent may strengthen a C—Pt bond and induce shortening of a wavelength. A ring such as pyridine in the carbene is linked to the CY4 ring in Formula 1, in the form of a cyclophane. Therefore, exciplex formation is suppressed, which induces short-wavelength emission.
Therefore, an electronic apparatus (for example, an organic light-emitting device) emitting deep blue light (for example, blue light having a maximum emission wavelength in a range of about of 430 nm to about 475 nm) and having high durability during driving, excellent efficiency, and long lifespan may be implemented by using the organometallic compound.
Methods of synthesizing the organometallic compound represented by Formula 1 may be readily understood by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
In an embodiment,
In an embodiment, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.
In an embodiment, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.
In an embodiment, the emission layer may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 500 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 420 nm to about 490 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 475 nm.
In an embodiment, 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. In an embodiment, 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 or in a range of about 430 nm to about 475 nm.
In an embodiment, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may directly contact the emission layer.
In an embodiment, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the at least one of the first capping layer and the second capping layer may include the organometallic compound represented by Formula 1. The first capping layer and/or the second capping layer may each be the same as described in the specification.
In an embodiment, the light-emitting device may include:
The wording “(interlayer and/or capping layer) includes an organometallic compound” as used herein may be to mean that the (interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds, each represented by Formula 1.
For example, the interlayer and/or the capping layer may include, as the organometallic compound, Compound BD1 only. In this regard, Compound BD1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the organometallic compound, Compound BD1 and Compound BD2. In this regard, Compound BD1 and Compound BD2 may be present in the same layer (for example, both Compound BD1 and Compound BD2 may be present in an emission layer), or may be present in different layers (for example, Compound BD1 may be present in an emission layer, and Compound BD2 may be present in an 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.
In an embodiment,
In Formula 3,
In an embodiment, in the light-emitting device,
Description of Second Compound, Third Compound, and Fourth Compound
The second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
For example, the light-emitting device may further include at least one of the second compound and the third compound, in addition to the first compound.
As another example, the light-emitting device may further include, in addition to the first compound, the fourth compound.
As another example, the light-emitting device may include the first compound, the second compound, the third compound, and the fourth compound.
In an embodiment, the interlayer may include the second compound. The interlayer may further include the third compound, the fourth compound, or a combination thereof, in addition to the first compound and the second compound.
In an embodiment, a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound may be at least about 0 eV and not more than about 0.5 eV (or, at least about 0 eV and not more than about 0.3 eV).
For example, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
In an embodiment, the fourth compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share boron (B).
In an embodiment, the fourth compound may include a condensed ring in which at least one third ring is condensed with at least one fourth ring,
In an embodiment, the interlayer may include the fourth compound. The interlayer may further include the second compound, the third compound, or a combination thereof, in addition to the first compound and the fourth compound.
In an embodiment, the interlayer may include the third compound. For example, the third compound may not include CBP or mCBP as described in the specification.
The emission layer in the interlayer may include: the first compound; and the second compound, the third compound, the fourth compound, or any combination thereof.
The emission layer may emit phosphorescence or fluorescence emitted from the first compound. For example, the phosphorescence or the fluorescence emitted from the first compound may be blue light.
For example, the emission layer in the light-emitting device may include the second compound and the third compound, and the second compound and the third compound may form an exciplex.
As another example, the emission layer in the light-emitting device may include the first compound, the second compound, and the third compound, and the second compound and the third compound may form an exciplex.
As another example, the emission layer in the light-emitting device may include the first compound and the fourth compound, and the fourth compound may serve to improve color purity, emission efficiency, and lifespan characteristics of the light-emitting device.
In an embodiment, the second compound may include a compound represented by Formula 2:
In Formula 2,
In an embodiment, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
In Formulae 3-1 to 3-5,
In an embodiment, 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,
[Description of Formulae 2, 3, 3-1 to 3-5, 502, and 503]
In Formula 2, b61 to b63 may respectively indicate numbers of L61 to L63, and b61 to b63 may each independently be an integer from 1 to 5. When b61 is 2 or greater, two or more L61(s) may be identical to or different from each other, when b62 is 2 or greater, two or more L62(s) may be identical to or different from each other, and when b63 is 2 or greater, two or more L63(s) may be identical to or different from each other. For example, b61 to b63 may each independently be 1 or 2.
In embodiments, in Formula 2, L61 to L63 may each independently be:
In an embodiment, in Formula 2, a bond between L61 and R61, a bond between L62 and R62, a bond between L63 and R63, a bond between two or more L61(s), a bond between two or more L62(s), a bond between two or more L63(s), a bond between L61 and a carbon atom between X64 and X65, a bond between L62 and a carbon atom between X64 and X66, and a bond between L63 and a carbon atom between X65 and X66 may each be a carbon-carbon single bond.
In Formula 2, X64 may be N or C(R64), X65 may be N or C(R65), X66 may be N or C(R66), and at least one of X64 to X66 may each be N. R64 to R66 may each be the same as described in the specification. For example, two or three of X64 to X66 may each be N.
R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is 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 in the specification.
For example, in Formulae 2, 3-1 to 3-5, 502, and 503, R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b; and R10a may each independently be:
In Formula 91,
For example, in Formula 91,
In an embodiment, in Formulae 2, 3-1 to 3-5, 502, and 503, R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b; and R10a may each independently be:
hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-249, —C(Q1)(Q2)(Q3), —Si(a)(Q2)(Q3), —N(Q1)(Q2), or —P(═O)(Q1)(Q2) (Q1 to Q3 may each be the same as described in the specification).
In Formulae 9-1 to 9-19 and 10-1 to 10-249, * indicates a binding site to a neighboring atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.
In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 respectively indicate numbers of R71 to R74 and R501 to R504, and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 2 or more, two or more R71(s) may be identical to or different from each other, when a72 is 2 or more, two or more R72(s) may be identical to or different from each other, when a73 is 2 or more, two or more R73(s) may be identical to or different from each other, when a74 is 2 or more, two or more R74(s) may be identical to or different from each other, when a501 is 2 or more, two or more R501(s) may be identical to or different from each other, when a502 is 2 or more, two or more R502(s) may be identical to or different from each other, when a503 is 2 or more, two or more R503(s) may be identical to or different from each other, and when a504 is 2 or more, two or more R504(s) may be identical to or different from each other. In embodiments, a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
In an embodiment, in Formula 2, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may each not be a phenyl group.
In an embodiment, in Formula 2, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may be identical to each other.
In an embodiment, in Formula 2, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may be different from each other.
In an embodiment, in Formula 2, b61 and b62 may each independently be 1, 2, or 3, and L61 and L62 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, R61 and R62 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(a)(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 an embodiment, in Formulae CY51-1 to CY51-26 and Formula CY52-1 to 52-26,
In an embodiment, in Formulae 3-1 to 3-5, L81 to L85 may each independently be:
In an embodiment, a group represented by in Formulae 3-1 and 3-2 may be a group represented by one of Formulae CY71-1 (1) to CY71-1(8), and/or
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),
[Examples of Second Compound, Third Compound, and Fourth Compound]
In an embodiment, the second compound may include at least one of Compounds ETH1 to ETH84:
In an embodiment, the third compound may include at least one of Compounds HTH1 to HTH52:
In an embodiment, the fourth compound may include at least one of Compounds DFD1 to DFD12:
In Compounds ETH1 to ETH84, HTH1 to HTH52, and DFD1 to DFD12, Ph represents a phenyl group, D5 represents substitution with five deuterium atoms, and D4 represents substitution with four deuterium atoms. For example, a group represented by
may be identical to a group represented by
In an embodiment, the light-emitting device may satisfy at least one of Condition 1 to Condition 4:
LUMO energy level (eV) of third compound>LUMO energy level (eV) of first compound; [Condition 1]
LUMO energy level (eV) of first compound>LUMO energy level (eV) of second compound; [Condition 2]
HOMO energy level (eV) of first compound>HOMO energy level (eV) of third compound; and [Condition 3]
HOMO energy level (eV) of third compound>HOMO energy level (eV) of second compound. [Condition 4]
A HOMO energy level and a LUMO energy level of each of the first compound, the second compound, and the third compound may each be a negative value, and may each be measured according to a method of the related art.
In an embodiment, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be at least about 0.1 eV and not more than about 1.0 eV, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be at least about 0.1 eV and not more than about 1.0 eV, an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be not more than about 1.25 eV (for example, not more than about 1.25 eV and at least about 0.2 eV), and an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be not more than about 1.25 eV (for example, not more than about 1.25 eV and at least about 0.2 eV).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, 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 first compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. For example, the first compound may be a phosphorescent dopant or a phosphorescent emitter.
Phosphorescence or fluorescence emitted from the first compound may be blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may effectively transfer energy to the first compound, which may be a dopant or an emitter, so that the emission efficiency from the first compound may be improved.
The auxiliary dopant may be different from the first compound and the host.
For example, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In an embodiment, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to a second embodiment, the first compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from the host and the dopant, and the emission layer may emit phosphorescence or fluorescence (for example, delayed fluorescence) emitted from the dopant.
In an embodiment, the first compound of the second embodiment may serve as an auxiliary dopant that transfers energy to a dopant (or an emitter), and may not serve as a dopant.
As another example, the first compound of the second embodiment may serve as an emitter and as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In an embodiment, phosphorescence or fluorescence emitted from the dopant (or the emitter) of the second embodiment may be blue phosphorescence or blue fluorescence (for example, blue delayed fluorescence).
The dopant (or the emitter) of the second embodiment may be a phosphorescent dopant material (for example, the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (for example, the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).
The blue light of the first embodiment and the second embodiment may be blue light having a maximum emission wavelength of about 430 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
The auxiliary dopant of the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503.
The host of the first embodiment and the second embodiment may be any host material (for example, the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or any combination thereof).
In an embodiment, the host of the first embodiment and of the second embodiment may be the second compound, the third compound, or any combination thereof.
Embodiments provide 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, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic apparatus may be the same as described in the specification.
Embodiments provide an organometallic compound which may be represented by Formula 1. Formula 1 may be the same as described in the specification.
[Description of
Hereinafter, a structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described in connection with
[First Electrode 110]
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 to facilitate the injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the 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 an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a structure consisting of a single layer, or a structure including multiple layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
[Interlayer 130]
The interlayer 130 is disposed on the first electrode 110. The interlayer 130 includes an emission layer.
The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer and an electron transport region located between the emission layer and the second electrode 150.
The interlayer 130 may further include a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, or the like, in addition to various organic materials.
In an embodiment, the interlayer 130 may include multiple light-emitting units sequentially stacked between the first electrode 110 and the second electrode 150 and a charge generation layer located between the light-emitting units. When the interlayer 130 includes multiple light-emitting units and a charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[Hole Transport Region in Interlayer 130]
The hole transport region may have: a structure consisting of a single layer consisting of a single material; a structure consisting of a single layer consisting of 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 embodiments, a hole transport region may have a multilayer 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 a hole transport region is not limited thereto.
A hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
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 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 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 CY203.
In an embodiment, 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 an embodiment, xa1 in Formula 201 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 an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may not include groups represented by Formulae CY201 to CY203.
In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY203, and may each independently include at least one of groups represented by Formulae CY204 to CY217.
In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include groups represented by Formulae CY201 to CY217.
In an embodiment, a 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 a hole transport region may be about 50 Å to about 10,000 Å. For example, a thickness of a hole transport region may be in a range of about 100 Å to about 4,000 Å. When a hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of a hole injection layer may be about 100 Å to about 9,000 Å, and a thickness of a hole transport layer may be about 50 Å to about 2,000 Å. For example, a thickness of a hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, a thickness of a 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 these ranges, satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance of a wavelength of light emitted by an 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]
A hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, 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 an element EL1 and an 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.
In Formula 221,
In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a non-metal, a metalloid, or any combination thereof.
Examples of a metal may include an alkali metal (for example, lithium (L1), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of a metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of a non-metal may include oxygen (O) and a halogen (for example, F, Cl, Br, I, etc.).
For example, examples of a compound including the element EL1 and the element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, or a metal iodide), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or any combination thereof.
Examples of a metal oxide may include a tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and a rhenium oxide (for example, ReO3, etc.).
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, and a lanthanide metal halide.
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, and CsI.
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, Mgl2, CaI2, SrI2, and BaI2.
Examples of a transition metal halide may include a titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), a vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), a molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), a manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of a post-transition metal halide may include a zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (for example, 1n13, etc.), and a tin halide (for example, SnI2, etc.).
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 (for example, SbCl5, etc.).
Examples of aa metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[Emission Layer in Interlayer 130]
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 may be in contact with each other or may be separated from each other. In an embodiment, 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 may be mixed with each other in a single layer to emit white light.
An emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
An amount of the dopant in the emission layer may be in a range of about 0.01 wt % to about 15 wt % based on 100 wt % of the host.
In an embodiment, the emission layer may include a quantum dot.
In an embodiment, an 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 an emission layer may be about 100 Å to about 1,000 Å For example, a thickness of an emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of an emission layer is within the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
[Host]
The emission layer may include the second compound or the third compound described in the specification, or any combination thereof.
In an embodiment, the host may include a compound represented by Formula 301 below:
[Ar301]xb11-[(L301)xb1-R301]xb21 [Formula 301]
For example, when xb11 in Formula 301 is 2 or more, two or more Ar301(s) may be linked to each other via a single bond.
As another example, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
As another example, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
As another example, 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 an embodiment, 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.
[Phosphorescent Dopant]
The emission layer may include the first compound as described in the specification, as a phosphorescent dopant.
In an embodiment, when the emission layer includes the first compound as described in the specification and the first compound serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may 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 an embodiment, in Formula 402, X401 may be nitrogen and X402 may be carbon, or X401 and X402 may each be nitrogen.
In an embodiment, in Formula 401, when xc1 is 2 or more, two ring A401(s) among two or more L401(s) may optionally be linked to each other via T402, which is a linking group, and two ring A402(s) among two or more L401(S) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as described in connection with T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:
[Fluorescent Dopant]
When the emission layer includes the first compound as described in the specification and the first compound serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In an embodiment, when the emission layer includes the first compound as described in the specification and the first compound serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
The fluorescent dopant and the auxiliary dopant may each independently include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
For example, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501 below:
In an embodiment, in Formula 501, Ar501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
In an embodiment, in Formula 501, xd4 may be 2.
In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include one of the following Compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described in the specification.
[Delayed Fluorescence Material]
An emission layer may include the fourth compound as described in the specification, as a delayed fluorescence material.
In an embodiment, the emission layer may include the fourth compound, and may further include a delayed fluorescence material.
In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in an 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 greater than or equal to about 0 eV and less than or equal to about 0.5 eV. When the difference between a triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence material may effectively occur, and thus, the emission efficiency of the light-emitting device 10 may be improved.
In embodiments, the delayed fluorescence material may include: a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, and a π electron-deficient nitrogen-containing C1-C60 cyclic group), a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other while sharing boron (B), and the like.
Examples of a delayed fluorescence material may include at least one of Compounds DF1 to DF14:
[Quantum Dot]
An 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, 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.
According to the wet chemical process, a precursor material is mixed with an organic solvent to grow a quantum dot particle crystal. As the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled through a process which may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), and which has a lower cost.
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, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; 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, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, a Group III-V semiconductor compound may further include Group II elements. Examples of a Group III-V semiconductor compound further including Group II elements may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of a Group III-VI semiconductor compound may include: a binary compound, such GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3, or InGaSe3; 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, or AgAlO2; 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, or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, or the like; or any combination thereof.
Examples of a Group IV element or compound may include: a single element material, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
Each element included in a multi-element compound such as a binary compound, a ternary compound and a quaternary compound may exist in a particle with a uniform concentration or at a non-uniform concentration.
In an embodiment, the quantum dot may have a single structure or a core-shell structure. In an embodiment, in the case that the quantum dot has a single structure, the concentration of each element included in the corresponding quantum dot may be uniform, a material contained in the core and the material contained in the shell may be different from each other.
The shell of the quantum dot may serve as a protective layer to prevent chemical degeneration of the core to maintain semiconductor characteristics and/or may serve as a charging layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. An interface between the core and the shell of the quantum dot may have a concentration gradient that decreases toward the core.
Examples of a shell of the quantum dot may include a metal oxide, a metalloid, or a non-metal, a semiconductor compound, or any combination thereof. Examples of the metal oxide, a metalloid, or a non-metal may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; 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. 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.
A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be equal to or less than about 45 nm. For example, a FWHM of an emission wavelength spectrum of a quantum dot may be equal to or less than about 40 nm. For example, a FWHM of an emission wavelength spectrum of a quantum dot may be equal to or less than about 30 nm or less. Within these ranges, color purity or color reproducibility may be increased. 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 a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
Because the energy band gap 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. Therefore, by utilizing quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In an embodiment, 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 combining light of various colors.
[Electron Transport Region in Interlayer 130]
An 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.
An 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 embodiments, an 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 an electron transport region is not limited thereto.
In an embodiment, an electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, an electron transport region may include a compound represented by Formula 601.
[Ar601]xe11-[(L601)xe1-R601]xe21 [Formula 601]
In Formula 601,
For example, when xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked to each other via a single bond.
In an embodiment, in Formula 601, Ar601 may be an anthracene group that is unsubstituted or substituted with at least one R10a.
In an embodiment, an electron transport region may include a compound represented by Formula 601-1:
In embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In embodiments, an 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, 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile (CNNPTRZ), or any combination thereof:
A thickness of an electron transport region may be about 100 Å to about 5,000 Å. For example, a thickness of an electron transport region may be in a range of about 160 Å to about 4,000 Å. When an 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 a buffer layer, a hole blocking layer, or an electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and a thickness of an electron transport layer may be about 100 Å to about 1,000 Å. For example, a thickness of a buffer layer, a hole blocking layer, or an electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, a thickness of an electron transport layer may be in a range of about 150 Å to about 500 Å. When a thickness of the buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and/or an electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
An electron transport region (for example, 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 an alkali metal complex or the alkaline earth-metal complex may each independently include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a L1 complex. The L1 complex may include, for example. Compound ET-D1 (LiQ) or Compound ET-D2:
An 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 be in direct contact with 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, or a structure including a multiple layers 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.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, an alkaline earth metal-containing compound, and a rare earth metal-containing compound may include oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include alkali metal oxides, such as Li2O, Cs2O, or K2O, alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (x is a real number satisfying the condition of 0<x<1), or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of a 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, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion and, as a ligand bonded to the metal ion (for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof).
In an embodiment, an 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 an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In an embodiment, an electron injection layer may consist of an alkali metal-containing compound (for example, an alkali metal halide); or an electron injection layer may consist of an alkali metal-containing compound (for example, an 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, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, or the like.
When an electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth-metal complex, rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of an electron injection layer may be about 1 Å to about 100 Å. For example, a thickness of an electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of an electron injection layer is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[Second Electrode 150]
The second electrode 150 may be located on the interlayer 130 having such a structure. The second electrode 150 may be a cathode, which is an electron injection electrode. A material for forming the second electrode 150 may be a material having a low-work function, such as a metal, an alloy, an electrically conductive compound, or any combination thereof.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), aluminum-magnesium (Al—Mg), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multilayer structure.
[Capping Layer]
The light-emitting device 10 may include a first capping layer outside the first electrode 110, and/or a second capping layer outside the second electrode 150. For example, 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 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 stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order.
Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first capping layer. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which 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 each increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the emission efficiency of the light-emitting device 10 may be improved.
The first capping layer and second capping layer may each include a material having a refractive index greater than or equal to about 1.6 or more (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 porphyrin 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 be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In an embodiment, 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 an embodiment, 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:
[Film]
The organometallic compound represented by Formula 1 may be included in various films. In embodiments, a film may include the organometallic compound represented by Formula 1. The film may include an optical member (or a light control member) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, or the like), or a protective member (for example, an insulating layer, a dielectric layer, or the like).
[Electronic Apparatus]
The light-emitting device may be included in various electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
The electronic apparatus (for example, 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 located in at least one traveling direction of light emitted from the light-emitting device. In an embodiment, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be a light-emitting device as described herein. In an embodiment, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
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 located between the subpixels to define each subpixel.
The color filter may further include color filter areas and light-shielding patterns located between the color filter areas, and the color conversion layer may include color conversion areas and light-shielding patterns located 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, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. In embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, 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 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 a 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 each have different maximum emission wavelengths from one 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 active 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, etc.
The active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color-conversion layer and the light-emitting device. The sealing portion 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 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 further included on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the intended use of the electronic apparatus. A functional layer 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 utilizing biometric information of a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device, a biometric information collector.
The electronic apparatus may be applied to various displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic diaries, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
[Electronic Device]
The light-emitting device may be included in various electronic devices.
For example, an electronic device 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 or 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 portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality 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 emission efficiency and long lifespan, the electronic device including the light-emitting device may have high luminance, high resolution, and low power consumption.
[Description of
The electronic apparatus (for example, a 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 formed 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 located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active 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 active layer 220 from the gate electrode 240 may be located on the active layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
An interlayer insulating film 250 is located on the gate electrode 240. The interlayer insulating film 250 may be placed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose a source region and a drain region of the active 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 active layer 220.
The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
A pixel-defining layer 290 containing an insulating material may be located on the first electrode 110. The pixel-defining layer 290 may expose a region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel-defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in
The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or a combination thereof; or a combination of the inorganic film and the organic film.
The electronic apparatus (for example a light-emitting apparatus) of
[Description of
The electronic device 1 may be an apparatus that displays a moving image or a still image, and may be not only a portable electronic device, such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic diary, an electronic book, a portable multimedia player (PMP), a navigation system, or an ultra-mobile PC (UMPC), but also may be various products, such as a television (TV), a laptop computer, a monitor, a billboard, or Internet of things (IOT), or a part thereof.
The electronic device 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 part thereof. However, the disclosure is not limited thereto.
In an embodiment, the electronic device 1 may be a dashboard of a vehicle, a center information display (CID) arranged on a center fascia or dashboard of a vehicle, a room mirror display instead of a side-view mirror of a vehicle, an entertainment for the back seat of a vehicle, or a display arranged on the back of the front seat of a vehicle, a head up display (HUD) installed on 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 device 1 may include a display area DA and a non-display area NDA located outside the display area DA. A display apparatus 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 an electrical signal or electric power to display devices arranged in the display area DA and the like may be arranged in the non-display area NDA. A pad, which is an area to which an electronic device or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
The electronic device 1 may have different lengths in an X-axis direction and a y-axis direction. For example, as shown in
[Description of
Referring to
In an embodiment, a vehicle 1000 may travel on a road or track. The vehicle 1000 may move in a certain direction according to rotation of at least one wheel. In an embodiment, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction vehicle, a two-wheeled vehicle, a prime mover apparatus, a bicycle, and a train traveling on a track.
The vehicle 1000 may include a body having an interior trim and an exterior trim, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts, except for the body. The exterior trim of the body may include a pillar provided at a boundary between a front panel, a roof, a roof panel, a rear panel, a trunk, and a door. A chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, and front, rear, left and right wheels.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side-view mirror 1300, a cluster 1400, a center fascia 1500, a front passenger seat dashboard 1600, and a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on 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. The second side window glass 1120 may be arranged adjacent to the front passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be 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 apart from each other in the x direction or in the −x direction. For example, a virtual straight line L connecting the side window glasses 1100 to each other may extend in the x direction or in the −x direction. For example, the virtual straight line L connecting the first side window glass 1110 to the second side window glass 1120 may extend in the x direction or in the −x direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side-view mirror 1300 may provide a rear view of the vehicle 1000. The side-view mirror 1300 may be installed on the exterior trim of the body. In an embodiment, multiple side-view mirrors 1300 may be provided. One of the side-view mirrors 1300 may be arranged outside the first side window glass 1110. Another of the side-view mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be located 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 light, a high beam indicator light, a warning light, a seat belt warning light, an odometer, an odometer, an automatic gear selector lever 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 apparatus, an air conditioning apparatus, and a heater of a seat are arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.
The front passenger seat dashboard 1600 may be apart from the cluster 1400 with the center fascia 1500 therebetween. In an embodiment, the cluster 1400 may be arranged to correspond to a driver's seat (not shown), and the front passenger seat dashboard 1600 may be arranged to correspond to a front passenger seat (not shown). In an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the front passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In an embodiment, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In an embodiment, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the front passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display, an inorganic electroluminescent (EL) light-emitting display (inorganic light-emitting display), and a quantum dot display. Hereinafter, an organic light-emitting display including a light-emitting device according to an embodiment is described as an example of the display apparatus 2 according to an embodiment, but in embodiments of the disclosure, various types of display apparatuses as described above may be used.
Referring to
Referring to
Referring to
Respective layers included in a hole transport region, an emission layer, and respective layers included in an electron transport region may be formed in a selected region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
When layers constituting a hole transport region, an emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as used herein may be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as used herein may be a cyclic group that has one to sixty 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. In an embodiment, a C1-C20 heterocyclic group may have 3 to 61 ring-forming atoms.
The term “cyclic group” as utilized 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 does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein may be a heterocyclic group that has 1 to 60 carbon atoms and may include *—N═*′ as a ring-forming moiety.
In embodiments,
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 cyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, and the like) according to the structure of a formula for which the corresponding term is used. For example, “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 and a monovalent C1-C60 heterocyclic group may include 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 and a divalent C1-C60 heterocyclic group may include 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-C20 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C20 alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty 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, and a tert-decyl group. The term “C1-C20 alkylene group” as used herein may be a divalent group having a same structure as the C1-C20 alkyl group.
The term “C2-C60 alkenyl group” as used herein refers to 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 include an ethenyl group, a propenyl group, and a butenyl group. 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 the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the 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, and an isopropyloxy group.
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 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 a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein may be a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. 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” used herein may be a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having a same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein may be a monovalent cyclic group that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and 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, and a 2,3-dihydrothiophenyl group. 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 having six to sixty carbon atoms, and the term “C6-C60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system having six to sixty carbon atoms. Examples of the 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, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “C1-C20 heteroaryl group” as used herein may be a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group 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, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein may be a monovalent group having two or more rings condensed to each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having a same structure as a monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group having two or more rings condensed to each other, at least one heteroatom other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and non-aromaticity in its molecular structure when considered as a whole. 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, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein indicates —O(A102) (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein indicates —S(A103) (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 aryl alkyl group” used herein may be a group represented by -(A104)(A105) (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroaryl alkyl group” used herein may be a group represented by -(A106)(A107) (where 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; or a C1-C20 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C20 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-C20 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 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 “the 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” as used herein may be a phenyl group, the term “Me” refers to a methyl group, the term “Et” refers to an ethyl group, the terms “tert-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 that is 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 that is 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 that is substituted with a C6-C60 aryl group.
The symbols * and *′ 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 on orthogonal coordinates (for example a Cartesian coordinate system), and may be construed in a broader sense than the aforementioned three axes. For example, the x-axis, the y-axis, and the z-axis may be axes that are orthogonal to each other, but may refer to different directions that are not orthogonal to each other.
Hereinafter, a compound and light-emitting device according to embodiments will be described in more detail with reference to the following Synthesis Examples. The wording “B was used instead of A” used in describing Synthesis Examples refers to an identical molar equivalent of B used in place of A.
(Experiment Information)
Trimethyl phosphite (TCI), N,N-dimethylcarbamoyl chloride (TCI), trimethylsilyl cyanide (TCI), 1,2-dichloroethane (TCI), (3-bromophenyl)(2,4,6-trimethylphenyl)iodonium triflate (BLD Pharm.), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (FNG Research), 9-(5-(4-(tert-butyl)phenyl)-4-methylpyridin-2-yl)-9H-carbazol-2-ol (Daejung Chemicals & Metals Co., Ltd.), 9-(4-(tert-butyl)pyridin-2-yl)-6-phenyl-9H-carbazol-2-ol (FNG Research).
2,5-di(bromo-methyl)pyridine (1 eq) was dissolved in a solvent of toluene:ethanol (7:1) and stirred, and a methanol solution in which 1,4-benzenedimethanethiol (1 eq) and potassium tert-butoxide (1 eq) were dissolved was slowly added dropwise thereto. After stirring at 80° C. for 24 hours and cooling to room temperature, a precipitate was filtered, and the filtrate was subjected to column chromatography (MC:acetone=10:1) to obtain BD1-b at a yield of 70%.
Trimethyl phosphite (0.1M) was added into Intermediate BD1-a, followed by stirring at room temperature for 12 hours under UV light. After trimethyl phosphite was removed under reduced pressure, column chromatography (MC:acetone=10:1) was used to obtain BD-c at a yield of 30%.
After Intermediate BD1-b (1 eq) was dissolved in methylene chloride (0.1M), mCPBA (3.5 eq) was added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, a solvent was removed therefrom under reduced pressure, and extracted with methylene chloride and distilled water. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using magnesium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain a target compound at a yield of 80%.
After Intermediate BD1-c (1 eq) was dissolved in methylene chloride (0.1M), a solution (0.5M) obtained by dissolving N,N-dimethylcarbamoyl chloride in methylene chloride was slowly added dropwise thereto and stirred for 30 minutes. A solution (0.5M) obtained by dissolving trimethylsilyl cyanide in methylene chloride was added dropwise thereto, followed by stirring for 24 hours. After completion of the reaction, a solvent was removed therefrom under reduced pressure, and extracted with methylene chloride and distilled water. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using magnesium sulfate. A residue obtained by removing the solvent therefrom was separated using column chromatography to obtain a target compound at a yield of 50%.
Intermediate BD1-d (1 eq) was dissolved in 1,2-dichloroethane (0.1M), followed by stirring at 80° C. for 5 hours. After completion of the reaction, a solvent was removed therefrom under reduced pressure, and extracted with methylene chloride (MC) and distilled water. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using magnesium sulfate. A residue obtained by removing the solvent therefrom was separated using column chromatography to obtain a target compound at a yield of 30%.
After Intermediate BD1-e (1 eq) was dissolved in acetic acid (0.1M), Pd/C (10% w/w) was added thereto, followed by stirring for 3 hours under a hydrogen stream. After completion of the reaction, the reaction mixture was filtered using Celite, and a solvent was removed therefrom under reduced pressure. After triethylamine (2 eq) was added and the mixture was stirred at 80° C. for 2 hours, the reaction was terminated. An organic layer was extracted from the resulting mixture by using methylene chloride and distilled water, and the extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. A residue obtained by removing the solvent therefrom was separated using column chromatography to obtain a target compound at a yield of 57%.
After Intermediate BD1-f (1 eq) was dissolved in toluene (0.1M), POCl3 (3 eq) was added thereto, followed by stirring at 80° C. for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and a solvent was removed therefrom under reduced pressure, dissolved in chloroform, washed with aqueous NaOH solution, and dried over magnesium sulfate. A residue obtained by removing the solvent therefrom was separated using column chromatography to obtain a target compound at a yield of 51%.
Intermediate BD1-g (1 eq), cuprous chloride (0.1 eq), and (3-bromophenyl)(2,4,6-trimethylphenyl)iodonium triflate (1.5 eq) were dissolved in MC (0.1M), followed by stirring at 50° C. for 12 hours. After completion of the reaction, a solvent was removed therefrom under reduced pressure, and extracted with methylene chloride and distilled water. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using magnesium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain a target compound at a yield of 70%.
Intermediate BD1-h (1 eq), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (1.1 eq), CuI (0.01 eq), K2CO3 (2.0 eq), and L-Proline (0.02 eq) were dissolved in DMSO (0.1M), followed by stirring at 130° C. for 24 hours. The reaction mixture was cooled to room temperature, and an extraction process was performed thereon three times by using dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated, and column chromatography was used to obtain a target compound at a yield of 68%.
Intermediate BD1-i (1.0 eq), dichloro(1,2-dicyclooctadiene)platinum (Pt(COD)Cl2) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in 1,4-dioxane (0.1 M), followed by stirring at 120° C. for 72 hours. The reaction mixture was cooled to room temperature, and an extraction process was performed thereon three times by using dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated, and column chromatography was used to synthesize Compound BD1 (yield: 23%).
Intermediate BD1-h (1 eq), 9-(5-(4-(tert-butyl)phenyl)-4-methylpyridin-2-yl)-9H-carbazol-2-ol (1.1 eq), CulI (0.01 eq), K2CO3 (2.0 eq), and L-Proline (0.02 eq) were dissolved in DMSO (0.1M), followed by stirring at 130° C. for 24 hours. The reaction mixture was cooled to room temperature, and an extraction process was performed thereon three times by using dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated, and column chromatography was used to obtain a target compound at a yield of 58%.
Intermediate BD13-i (1.0 eq), dichloro(1,2-dicyclooctadiene)platinum (Pt(COD)Cl2) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in 1,4-dioxane (0.1 M), followed by stirring at 120° C. for 72 hours. The reaction mixture was cooled to room temperature, and an extraction process was performed thereon three times by using dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated, and column chromatography was used to synthesize Compound BD13 (yield: 21%).
A target compound was obtained in the same manner as used to obtain Intermediate BD1-a of Synthesis Example 1, except that 2,3-dimethyl-1,4-benzenedimethanethiol was used instead of 1,4-benzenedimethanethiol.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-b of Synthesis Example 1, except that BD31-a was used instead of Intermediate BD1-a.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-c of Synthesis Example 1, except that BD31-b was used instead of Intermediate BD1-b.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-d of Synthesis Example 1, except that BD31-c was used instead of Intermediate BD1-c.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-e of Synthesis Example 1, except that BD31-d was used instead of Intermediate BD1-d.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-f of Synthesis Example 1, except that BD31-e was used instead of Intermediate BD1-e.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-g of Synthesis Example 1, except that BD31-f was used instead of Intermediate BD1-f.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-h of Synthesis Example 1, except that BD31-g was used instead of Intermediate BD1-g.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-i of Synthesis Example 1, except that BD31-h was used instead of Intermediate BD1-h.
A target compound was obtained in the same manner as used to obtain Compound BD1 of Synthesis Example 1, except that BD31-i was used instead of Intermediate BD1-i.
After Compound BD1 (1 eq) was dissolved in DMSO-d6 (0.2M), potassium tert-butoxide (0.05 eq) was added thereto, followed by stirring at 40° C. for 12 hours. The reaction mixture was cooled to room temperature, and an extraction process was performed thereon three times by using ethyl acetate and water, to thereby obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated, and column chromatography was used to obtain a target compound at a yield of 54%.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-a of Synthesis Example 1, except that (2,3-bis(methyl-d3)-1,4-phenylene)dimethanethiol was used instead of 1,4-benzenedimethanethiol.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-b of Synthesis Example 1, except that BD91-a was used instead of Intermediate BD1-a.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-c of Synthesis Example 1, except that BD91-b was used instead of Intermediate BD1-b.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-d of Synthesis Example 1, except that BD91-c was used instead of Intermediate BD1-c.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-e of Synthesis Example 1, except that BD91-d was used instead of Intermediate BD1-d.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-f of Synthesis Example 1, except that BD91-e was used instead of Intermediate BD1-e.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-g of Synthesis Example 1, except that BD91-f was used instead of Intermediate BD1-f.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-h of Synthesis Example 1, except that BD91-g was used instead of Intermediate BD1-g.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-i of Synthesis Example 1, except that BD91-h was used instead of Intermediate BD1-h.
A target compound was obtained in the same manner as used to obtain Compound BD1 of Synthesis Example 1, except that BD91-i was used instead of Intermediate BD1-i.
A target compound was obtained in the same manner as used to obtain Intermediate BD31-h of Synthesis Example 3, except that (5-bromopyridin-3-yl)(mesityl)iodonium trifluoromethanesulfonate was used instead of (3-bromophenyl)(2,4,6-trimethylphenyl)iodonium triflate.
A target compound was obtained in the same manner as used to obtain Intermediate BD1-i of Synthesis Example 1, except that Intermediate BD106-h was used instead of Intermediate BD1-h, and 9-(4-(tert-butyl)pyridin-2-yl)-6-phenyl-9H-carbazol-2-ol was used instead of 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol.
A target compound was obtained in the same manner as used to obtain Compound BD1 of Synthesis Example 1, except that BD106-i was used instead of Intermediate BD1-i.
1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples 1 to 6 are shown in Table 1. Synthesis methods of other compounds in addition to the compounds shown in Table 1 may be readily recognized by those skilled in the art by referring to the synthesis paths and source materials.
1H NMR (CDCl3, 400 MHz)
As an anode, a glass substrate with 15 Ω/cm2 1,200 Å ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Compound BD1, used as a dopant, and ETH2:HTH2, used as a mixed host in a weight ratio of 5:5, were co-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å, wherein a ratio of the dopant to the mixed host was 10%, thereby forming a blue (fluorescent) emission layer. ETH2 was vacuum-deposited thereon to form a hole blocking layer having a thickness of 50 Å. Alq3 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, and LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al was vacuum-deposited thereon to form an Al electrode (cathode) having a thickness of 3000 Å to form an LiF/AI electrode, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices according to Examples 2 to 6 and Comparative Examples 1 to 4 were manufactured in the same manner as in Example 1, except that, corresponding dopants as described in Table 2 were used instead of Compound BD1 in forming the blue emission layer.
As shown in Table 2, it was found that the organic light-emitting devices of Examples 1 to 6 had lower driving voltage, higher emission efficiency, and better lifespan characteristics than the organic light-emitting devices of Comparative Examples 1 to 4.
According to embodiments, a light-emitting device having high efficiency and a long lifespan, and a high-quality electronic apparatus including the light-emitting device may be manufactured by using the organometallic compound.
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 |
|---|---|---|---|
| 10-2022-0143946 | Nov 2022 | KR | national |
