Patent Application
20250234778
This application claims priority to and benefits of Korean Patent Application No. 10-2024-0005475 under 35 U.S.C. § 119, filed on Jan. 12, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to a light-emitting device that includes a heterocyclic compound, an electronic apparatus that includes the light-emitting device, an electronic device that includes the light-emitting device, and the heterocyclic compound.
Light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed.
In a light-emitting device, a first electrode may be arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode may be sequentially arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as the holes and electrons, recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thereby generating 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 that includes a heterocyclic compound, an electronic apparatus that includes the light-emitting device, an electronic device that includes the light-emitting device, and the heterocyclic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the embodiments of the disclosure.
According to embodiments, a light-emitting device may include
In Formula 1,
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, a buffer 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, or any combination thereof.
In an embodiment, the light-emitting device may further include:
In an embodiment, the third compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
According to embodiments, an electronic apparatus may include the light-emitting device.
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.
In an embodiment, the electronic apparatus may further include a thin-film transistor, wherein
According to embodiments, an electronic device may include the light-emitting device.
In an embodiment, the electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet 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.
According to embodiments, a heterocyclic compound may be represented by Formula 1, which is explained herein.
In an embodiment, at least one of X2 and Y1 may each independently be O, S, or Se.
In an embodiment:
In an embodiment, ring CY11 to ring CY13, ring CY21 to ring CY23, and ring CYs may each independently be a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, or an isoquinoline group.
In an embodiment, R11 to R13, R21 to R23, R31 to R39, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, and E42 may each independently be:
In an embodiment, R11 to R13, R21 to R23, R31 to R39, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, and E42 may each independently be:
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae LP1 to LP4, which are explained below; and a moiety represented by
may be a moiety represented by one of Formulae RP1 to RP4, which are explained below.
In an embodiment, the heterocyclic compound may be represented by Formula 1-1, which is explained below.
In an embodiment, the heterocyclic compound may include: at least one deuterium; or at least one tert-butyl group; or at least one deuterium and at least one tert-butyl group.
In an embodiment, the heterocyclic compound may have a Stokes-shift equal to or less than about 20 nm.
In an embodiment, the heterocyclic compound may be one of Compounds 1 to 104, which are explained below.
It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purposes of limitation, and the disclosure is not limited to the embodiments described above.
The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated in and constitute a part of this specification.
The drawings illustrate embodiments of the disclosure and principles thereof. The above and other aspects and features of the disclosure will become more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:
The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like reference numbers and reference characters refer to like elements throughout.
In the specification, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.
In the specification, when an element is “directly on”, “directly connected to”, or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.
In the specification, 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.
In the specification, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B”. The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.
In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group consisting of” for the purpose of its meaning and interpretation. For example, “at least one of A, B, and C” may be understood to mean A only, B only, C only, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When preceding a list of elements, the term, “at least one of”, modifies the entire list of elements and does not modify the individual elements of the list.
It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element.
Thus, a first element could be termed a second element without departing from the teachings of the disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.
The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, 10%, or ±5% of the stated value.
It should be understood that the terms “comprises”, “comprising”, “includes”, “including”, “have”, “having”, “contains”, “containing”, and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
The term “interlayer” as used herein may refer to a single layer and/or all layers between a first electrode and a second electrode of a light-emitting device.
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, a light-emitting device may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and
The details on Formula 1 are the same as described herein.
In an embodiment,
In an embodiment, the heterocyclic compound may be included between the first electrode and the second electrode of the light-emitting device. For example, the interlayer may include the heterocyclic compound represented by Formula 1. For example, the emission layer may include the heterocyclic compound represented by Formula 1.
In an embodiment, the heterocyclic compound included in the emission layer may be a thermally activated delayed fluorescence (TADF) emitter, and the emission layer may emit delayed fluorescence. The emission layer may emit red light, green light, blue light, and/or white light. In an embodiment, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in a range of, for example, about 400 nm to about 490 nm. For example, the blue light may have a maximum emission wavelength in a range of about 420 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to 480 nm. In an embodiment, the emission layer may emit green light or red light. The green light may have a maximum emission wavelength in a range of, for example, about 490 nm to about 560 nm. The red light may have a maximum emission wavelength in a range of, for example, about 600 nm to about 700 nm. In an embodiment, the emission layer may further include a host, and an amount of the host may be greater than an amount of the heterocyclic compound represented by Formula 1.
In an embodiment, the light-emitting device may include a capping layer outside the first electrode or outside the second electrode.
In an embodiment, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one of the first capping layer and the second capping layer may include the heterocyclic compound represented by Formula 1. Further details on the first capping layer and/or the second capping layer are the same as described herein.
The expression “(an interlayer and/or a capping layer) includes at least one heterocyclic compound” as used herein may include a case in which “(an interlayer and/or a capping layer) each includes a same heterocyclic compound represented by Formula 1” and a case in which “(an interlayer and/or a capping layer) includes two or more different heterocyclic compounds each independently represented by Formula 1.”
In an embodiment, the interlayer and/or the capping layer may include, as the heterocyclic compound, only Compound 1. In this regard, Compound 1 may be present in an emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the heterocyclic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in a same layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
In an embodiment,
In Formula 20,
In an embodiment, the emission layer may include the first compound and at least one of the second compound and the third compound.
In an embodiment, the emission layer may include the first compound and the fourth compound.
In an embodiment, the emission layer may include the first compound, the second compound, the third compound, and the fourth compound.
In an embodiment, when the emission layer includes the first compound, the second compound, the third compound, and the fourth compound, based on 100% (wt %) of a total amount of the first compound, the second compound, the third compound, and the fourth compound,
In an embodiment, the second compound may include a compound represented by Formula 20-1, a compound represented by Formula 20-2, a compound represented by Formula 20-3, a compound represented by Formula 20-4, a compound represented by Formula 20-5, or any combination thereof:
In Formulae 20-1 to 20-5,
In an embodiment, the third compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In an embodiment, the third compound may include a compound represented by Formula 30:
In Formula 30,
In an embodiment, the fourth compound may include a compound represented by Formula 401:
M(L401)xc1(L402)xc2 [Formula 401]
In Formulae 401 and 402,
In an embodiment, a group represented by
in Formulae 20-1 and 20-2 may be a group represented by one of Formulae CY71-1(1) to CY71-1(8), and/or
in Formulae 20-1 and 20-3 may be a group represented by one of Formulae CY71-2(1) to CY71-2(8), and/or
in Formulae 20-2 and 20-4 may be a group represented by one of Formulae CY71-3(1) to CY71-3(32), and/or
in Formulae 20-3 to 20-5 may be a group represented by one of Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 20-5 may be a group represented by one of Formulae CY71-5(1) to CY71-5(8):
In Formulae CY71-1 (1) to CY71-1 (8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
In Formula 30, b51 to b53 respectively indicate the number of L51 to the number of L53, and b51 to b53 may each independently be an integer from 1 to 5. When b51 is 2 or more, two or more of L51 may be identical to or different from each other, when b52 is 2 or more, two or more of L52 may be identical to or different from each other, and when b53 is 2 or more, two or more of L53 may be identical to or different from each other. For example, b51 to b53 may each independently be 1 or 2.
In embodiments, in Formula 30, L51 to L53 may each independently be:
In an embodiment, in Formula 30, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between two or more of L51, a bond between two or more of L52, a bond between two or more of L53, a bond between L51 and carbon between X54 and X55 in Formula 30, a bond between L52 and carbon between X54 and X56 in Formula 30, and a bond between L53 and carbon between X55 and X56 in Formula 30 may each be a carbon-carbon single bond.
In Formula 30, X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one of X54 to X56 may each be N. R54 to R56 are each the same as described herein. For example, two or three of X54 to X56 may each be N.
In the specification, R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2), wherein Q1 to Q3 are each the same as described herein.
In an embodiment, R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b in Formulae 20-1 to 20-5 and 30; and R10a may each independently be:
In Formula 91,
In an embodiment, in Formula 91,
In an embodiment, R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b in Formulae 20-1 to 20-5, and 30; and R10a may each independently be:
In Formulae 9-1 to 9-39, 9-44 to 9-67, 10-1 to 10-154, and 10-201 to 10-368, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, and “TMG” represents a trimethylgermyl group.
In Formulae 20-1 to 20-5, a71 to a74 respectively indicate the number of R71 to the number of R74, and a71 to a74 may each independently be an integer from 0 to 20.
When a71 is 2 or more, two or more of R71 may be identical to or different from each other, when a72 is 2 or more, two or more of R72 may be identical to or different from each other, when a73 is 2 or more, two or more of R73 may be identical to or different from each other, and when a74 is 2 or more, two or more of R74 may be identical to or different from each other. In an embodiment, a71 to a74 may each independently be an integer from 0 to 8.
In an embodiment, in Formula 30, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may not each be a phenyl group.
In an embodiment, in Formula 30, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may be identical to each other.
In an embodiment, in Formula 30, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 may be different from each other.
In an embodiment, in Formula 30, b51 and b52 may each independently be 1, 2, or 3, and L51 and L52 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.
In an embodiment, in Formula 30, R51 and R52 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3); and
In an embodiment, in Formula 30,
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 CY52-1 to 52-26, R51a to R51e and R52a to R52e may each independently be:
In an embodiment, in Formulae 20-1 to 20-5, L81 to L85 may each independently be:
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 of ring A401 in two or more of L401 may be optionally linked to each other via T402, which is a linking group, or two of ring A402 in two or more of L401 may be optionally linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each 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 (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
In an embodiment, the second compound may include at least one of Compounds HTH1 to HTH56:
In an embodiment, the third compound may include at least one of Compounds ETH1 to ETH86:
In an embodiment, the fourth compound may include at least one of Compounds PD1 to PD41:
In Compounds HTH1 to HTH56 and ETH1 to ETH86, “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 Conditions 1 to 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 be measured according to a method of the related art.
In an embodiment, an absolute value of a difference between a LUMO energy level of the fourth compound and a LUMO energy level of the third compound may be in a range of about 0.1 eV to about 1.0 eV, an absolute value of a difference between a LUMO energy level of the fourth compound and a LUMO energy level of the second compound may be in a range of about 0.1 eV to about 1.0 eV, an absolute value of a difference between a HOMO energy level of the fourth compound and a HOMO energy level of the third compound may be equal to or less than about 1.25 eV (e.g., in a range of about 0.2 eV to about 1.25 eV), and an absolute value of a difference between a HOMO energy level of the fourth compound and a HOMO energy level of the second compound may be equal to or less than about 1.25 eV (e.g., in a range of about 0.2 eV to about 1.25 eV).
When the relationships between LUMO energy levels and HOMO energy levels satisfy the conditions as described above, a balance between holes and electrons injected into the emission layer may be achieved.
The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to a first embodiment, the 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 and the host may be different from each other, 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 phosphorescence emitter.
Phosphorescence or fluorescence emitted from the first compound may be green light or blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may serve as a sensitizer that effectively transfers energy to the first compound, which serves as a dopant or an emitter, thereby improving the luminescence efficiency of the first compound.
The auxiliary dopant may be different from each of the first compound and the host.
In an embodiment, the auxiliary dopant may be a phosphorescent dopant.
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, the host, and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
In an embodiment, the first compound in the second embodiment may not serve as a dopant, but may serve as an auxiliary dopant that transfers energy to a dopant (or to an emitter).
In an embodiment, the first compound in the second embodiment may serve as an emitter and may also serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In an embodiment, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be green or blue phosphorescence, or green or blue fluorescence (e.g., green or blue delayed fluorescence).
The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., an organometallic compound represented by Formula 401) or any fluorescent dopant material (e.g., the heterocyclic compound represented by Formula 1, a compound represented by Formula 501, or any combination thereof).
In the first embodiment and the second embodiment, the blue light may have a maximum emission wavelength in a range of about 390 nm to about 500 nm. For example, the blue light may have a maximum emission wavelength in a range of about 410 nm to about 490 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 455 nm to about 470 nm. In the first embodiment and the second embodiment, the green light may have a maximum emission wavelength in a range of about 490 nm to about 560 nm.
The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 401.
The host in the first embodiment and in the second embodiment may be any host material (e.g., a compound represented by Formula 301, a compound represented by 301-1, a compound represented by Formula 301-2, or any combination thereof).
In an embodiment, the host in the first embodiment and in the second embodiment may be the second compound, the third compound, or any combination thereof.
Embodiments also provide an electronic apparatus which may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, in an embodiment, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In 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. Further details on the electronic apparatus may be the same as described herein.
According to an embodiment, a heterocyclic compound may be represented by Formula 1:
In Formula 1, X1 may be O, S, Se, N(E11), C(═O), C(E11)(E12), or Si(E11)(E12).
In an embodiment, X1 may be O, S, Se, or N(E11). In an embodiment, X1 may be N(E11).
In Formula 1, X2 may be O, S, Se, N(E21), C(═O), C(E21)(E22), or Si(E21)(E22).
In an embodiment, X2 may be O, S, Se, or N(E21). In an embodiment, X2 may be O, S, or Se.
In Formula 1, Y1 may be O, S, Se, N(E31), C(═O), C(E31)(E32), or Si(E31)(E32).
In an embodiment, Y1 may be O, S, Se, or N(E31). In an embodiment, Y1 may be O, S, or Se.
In Formula 1, Y2 may be O, S, Se, N(E41), C(═O), C(E41)(E42), or Si(E41)(E42).
In an embodiment, Y2 may be O, S, Se, or N(E41). In an embodiment, Y2 may be N(E41).
In an embodiment, at least one of X2 and Y1 may each independently be O, S, or Se. In an embodiment, X2 may be O, S, or Se; Y1 may be O, S, or Se; or X2 may be O, S, or Se, and Y1 may be O, S, or Se.
In an embodiment, X1 may be O, S, Se, or N(E11), and E11 may be optionally linked to ring CY11 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T11)(T12)-*′, *—N(T11)-*′, *—Si(T11)(T12)-*′, or *—Ge(T11)(T12)-*′; or
Y2 may be O, S, Se, or N(E41), and E41 may be optionally linked to ring CY22 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T41)(T42)-*′, *—N(T41)-*′, *—Si(T41)(T42)-*′, or *—Ge(T41)(T42)-*′; or
X1 may be O, S, Se, or N(E11), Y2 may be O, S, Se, or N(E41), E11 may be optionally linked to ring CY11 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T11)(T12)-*′, *—N(T11)-*′, *—Si(T11)(T12)-*′, or *—Ge(T11)(T12)-*′, and E41 may be optionally linked to ring CY22 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T41)(T42)-*′, *—N(T41)-*′, *—Si(T41)(T42)-*′, or *—Ge(T41)(T42)-*′.
In Formula 1, X31 may be C(R31) or N, X32 may be C(R32) or N, X33 may be C(R33) or N, X34 may be C(R34) or N, X35 may be C(R35) or N, X36 may be C(R36) or N, X37 may be C(R37) or N, X38 may be C(R38) or N, and X39 may be C(R39) or N.
In Formula 1, X41 may be C(R41) or N, X42 may be C(R42) or N, X43 may be C(R43) or N, X44 may be C(R44) or N, X45 may be C(R45) or N, X46 may be C(R46) or N, X47 may be C(R47) or N, X48 may be C(R48) or N, and X49 may be C(R49) or N.
In Formula 1, Z1 and Z2 may each independently be N or P. In an embodiment, Z1 and Z2 may each be N.
In Formula 1, ring CY11 to ring CY13, ring CY21 to ring CY23, and ring CY3 may each independently be a C5-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, ring CY11 to ring CY13, ring CY21 to ring CY23, and ring CY3 may each independently be a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, or an isoquinoline group.
In an embodiment, ring CY11 to ring CY13, ring CY21 to ring CY23, and ring CY3 may each independently be a 6-membered ring.
In Formula 1, R11 to R13, R21 to R23, R31 to R39, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, and E42 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C6-C60 arylseleno group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In an embodiment, E11 and E41 may each independently be a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group unsubstituted or substituted with at least one R10a, a C6-C60 aryl group unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R10a, or a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, R11 to R13, R21 to R23, R31 to R3e, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, and E42 may each independently be:
In an embodiment, R11 to R13, R21 to R23, R31 to R39, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, and E42 may each independently be:
In Formulae 2-1 to 2-25,
In Formula 1,
Examples of a case in which, in Formula 1, X1 is N(E11), and E11 is linked to ring CY11 via a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(T11)(T12)-*′, *—N(T11)-*′, *—Si(T11)(T12)-* or *—Ge(T11)(T12)-*′ may include Compounds 9, 21, 22, or the like:
In Formula 1, T11, T12, T21, T22, T31, T32, T41, and T42 may each independently be hydrogen, deuterium, —F, a cyano group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C6-C60 aryl group unsubstituted or substituted with at least one R10a, or a C1-C60 heteroaryl group unsubstituted or substituted with at least one R10a.
In Formula 1, two or more neighboring groups among R11 to R13, R21 to R23, R31 to R39, R41 to R49, R5, E11, E12, E21, E22, E31, E32, E41, E42, T11, T12, T21, T22, T31, T32, T41, and T42 may be optionally linked to each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In Formula 1, a11 to a13 may each be an integer from 0 to 30.
In Formula 1, a21 to a23 may each be an integer from 0 to 30.
In Formula 1, a5 may be an integer from 0 to 30.
In Formula 1, R10a may be:
In an embodiment, in Formula 1, a moiety represented by
may be a moiety represented by one of Formulae LP1 to LP4, and
may be a moiety represented by one of Formulae RP1 to RP4:
In Formulae LP1 to LP4 and RP1 to RP4,
In an embodiment, the heterocyclic compound may be represented by Formula 1-1:
In Formula 1-1,
In an embodiment, the heterocyclic compound may be represented by one of Formulae 1-1(1) to 1-1(8):
In Formulae 1-1(1) to 1-1(8),
In an embodiment, the heterocyclic compound may be represented by one of Formulae 1-1(a) to 1-1(j):
In Formulae 1-1(a) to 1-1(j),
In an embodiment, the heterocyclic compound may include:
In an embodiment, the heterocyclic compound may have a Stokes-shift equal to or less than about 20 nm.
A Stokes-shift may be a difference between a maximum emission peak wavelength and an absorption peak wavelength. The Stokes-shift may be expressed as a λemi-λabs value. In an embodiment, the Stokes-shift of the heterocyclic compound may be 20 nm or less, 19 nm or less, 18 nm or less, 17 nm or less, 16 nm or less, 15 nm or less, 14 nm or less, 13 nm or less, 12 nm or less, 11 nm or less, 10 nm or less, 9 nm or less, at least 1 nm but not more than 20 nm, at least 2 nm but not more than 20 nm, at least 3 nm but not more than 20 nm, at least 4 nm but not more than 20 nm, at least 5 nm but not more than 20 nm, at least 6 nm but not more than 20 nm, at least 7 nm but not more than 20 nm, at least 8 nm but not more than 20 nm, at least 9 nm but not more than 20 nm, at least 10 nm but not more than 20 nm, at least 11 nm but not more than 20 nm, at least 12 nm but not more than 20 nm, at least 13 nm but not more than 20 nm, at least 14 nm but not more than 20 nm, at least 15 nm but not more than 20 nm, at least 16 nm but not more than 20 nm, at least 17 nm but not more than 20 nm, at least 18 nm but not more than 20 nm, at least 19 nm but not more than 20 nm, at least 1 nm but not more than 18 nm, at least 2 nm but not more than 18 nm, at least 3 nm but not more than 18 nm, at least 4 nm but not more than 18 nm, at least 5 nm but not more than 18 nm, at least 6 nm but not more than 18 nm, at least 7 nm but not more than 18 nm, at least 8 nm but not more than 18 nm, at least 9 nm but not more than 18 nm, at least 10 nm but not more than 18 nm, at least 11 nm but not more than 18 nm, at least 12 nm but not more than 18 nm, at least 13 nm but not more than 18 nm, at least 14 nm but not more than 18 nm, at least 15 nm but not more than 18 nm, at least 16 nm but not more than 18 nm, at least 17 nm but not more than 18 nm, at least 1 nm but not more than 16 nm, at least 2 nm but not more than 16 nm, at least 3 nm but not more than 16 nm, at least 4 nm but not more than 16 nm, at least 5 nm but not more than 16 nm, at least 6 nm but not more than 16 nm, at least 7 nm but not more than 16 nm, at least 8 nm but not more than 16 nm, at least 9 nm but not more than 16 nm, at least 10 nm but not more than 16 nm, at least 11 nm but not more than 16 nm, at least 12 nm but not more than 16 nm, at least 13 nm but not more than 16 nm, at least 14 nm but not more than 16 nm, at least 15 nm but not more than 16 nm, at least 1 nm but not more than 14 nm, at least 2 nm but not more than 14 nm, at least 3 nm but not more than 14 nm, at least 4 nm but not more than 14 nm, at least 5 nm but not more than 14 nm, at least 6 nm but not more than 14 nm, at least 7 nm but not more than 14 nm, at least 8 nm but not more than 14 nm, at least 9 nm but not more than 14 nm, at least 10 nm but not more than 14 nm, at least 11 nm but not more than 14 nm, at least 12 nm but not more than 14 nm, at least 13 nm but not more than 14 nm, at least 1 nm but not more than 12 nm, at least 2 nm but not more than 12 nm, at least 3 nm but not more than 12 nm, at least 4 nm but not more than 12 nm, at least 5 nm but not more than 12 nm, at least 6 nm but not more than 12 nm, at least 7 nm but not more than 12 nm, at least 8 nm but not more than 12 nm, at least 9 nm but not more than 12 nm, at least 10 nm but not more than 12 nm, at least 11 nm but not more than 12 nm, or more than 11 nm but not more than 12 nm.
The heterocyclic compound represented by Formula 1 may include three B atoms and two substituents, which are each introduced at an ortho position of a B atom.
As a result, in the heterocyclic compound, a multiple-resonance (MR) effect and structural rigidity may be strengthened, thereby inducing a distortion effect. Thus, a local excited (LE) state and a charge transfer (CT) state may be mixed, so that an orbital distribution between a lowest excited singlet (S1) state and a lowest excited triplet (T1) state may be changed.
For example, spin-orbital coupling may be strengthened, thereby canceling out an inhibition effect caused by the EI-Sayed rule, and reverse intersystem crossing (RISC) may be induced.
Accordingly, the heterocyclic compound may simultaneously have a deep HOMO energy level, a narrow Stokes-shift, and a short delayed fluorescence lifespan, and a light-emitting device including the heterocyclic compound may have improved luminescence efficiency and lifespan.
Since the heterocyclic compound represented by Formula 1 includes at least one deuterium or at least one tert-butyl group, the heterocyclic compound may have improved structural stability. Thus, when the heterocyclic compound is included in a light-emitting device, the light-emitting device may simultaneously have improved characteristics in terms of driving voltage, luminescence efficiency, and lifespan.
In an embodiment, the heterocyclic compound represented by Formula 1 may be one of Compounds 1 to 104. In an embodiment, in the light-emitting device, the first compound may include at least one of Compounds 1 to 104:
Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a transflective electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer 130 may be arranged on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound, an inorganic material such as a quantum dot, or the like.
In an embodiment, the interlayer 130 may include two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between adjacent units among the two or more emitting units. When the interlayer 130 includes the two or more light-emitting units and the at least one charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
In an embodiment, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in its respective stated order, but the structure of the hole transport region is not limited thereto.
In embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In Formulae 201 and 202,
In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each independently be the same as described in connection with R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a.
In an embodiment, in Formulae CY201 to CY217, ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In 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, in Formula 201, xa1 may be 1, R201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In 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.
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, the hole transport region may include: one of Compounds HT1 to HT46; m-MTDATA; TDATA; 2-TNATA; NPB (NPD); p-NPB; TPD; spiro-TPD; spiro-NPB; methylated NPB; TAPC; HMTPD; 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA); polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA); poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS); polyaniline/camphor sulfonic acid (PANI/CSA); polyaniline/poly(4-styrenesulfonate) (PANI/PSS); or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the ranges described above, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer may block the leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
[p-Dopant]
The hole transport region may further include, in addition to the materials described above, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be equal to or less than about −3.5 eV.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of a quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of a cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a non-metal, a metalloid, or a combination thereof.
Examples of a metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); and the like.
Examples of a metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Examples of a non-metal may include oxygen (O), a halogen (e.g., F, Cl, Br, I, etc.), and the like.
Examples of a compound including element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
Examples of a metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), a rhenium oxide (e.g., ReO3, etc.), and the like.
Examples of a metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and the like.
Examples of an alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
Examples of an alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and the like.
Examples of a transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), a vanadium halide (e.g., VF3, VCl3, VBrs, VI3, etc.), a niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (e.g., CrF3, CrO3, CrBr3, CrI3, etc.), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), a manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and the like.
Examples of a post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (e.g., InI3, etc.), a tin halide (e.g., SnI2, etc.), and the like.
Examples of a lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
Examples of a metalloid halide may include an antimony halide (e.g., SbCl5, etc.) and the like.
Examples of a metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (e.g., ZnTe, etc.), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other, to emit white light. In embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials may be mixed with each other in a single layer, to emit white light.
In an embodiment, the emission layer may include a host and a dopant (or an emitter). In an embodiment, the emission layer may further include an auxiliary dopant that promotes energy transfer to a dopant (or an emitter), in addition to the host and the dopant (or an emitter). When the emission layer includes the dopant (or emitter) and the auxiliary dopant, the dopant (or emitter) and the auxiliary dopant may be different from each other.
An amount (by weight) of the dopant (or emitter) in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
In an embodiment, the emission layer may include a quantum dot.
In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or as a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer is within any of the ranges described above, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
In an embodiment, the host may include a compound represented by Formula 301:
[Ar301]xb11—[(L301)xb1-R301]xb21 [Formula 301]
In Formula 301,
In an embodiment, in Formula 301, when xb11 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.
In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In Formulae 301-1 and 301-2,
In an embodiment, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (e.g., Compound H55), a Mg complex, a Zn complex, or any combination thereof.
In an embodiment, 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.
The emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal. Accordingly, the phosphorescent dopant may correspond to the fourth compound.
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:
M(L401)xc1(L402)xc2 [Formula 401]
In Formulae 401 and 402,
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 of ring A401 among two or more of L401 may be optionally linked to each other via T402, which is a linking group, and two of ring A402 among two or more of L401 may be optionally linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each 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 (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
In an embodiment, the phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:
The emission layer may include a fluorescent dopant and/or an auxiliary dopant.
In an embodiment, the fluorescent dopant and/or the auxiliary dopant may each independently include a compound represented by Formula 501:
In Formula 501,
In an embodiment, in Formula 501, Ar501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed with each other.
In 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 Compounds FD1 to FD37; DPVBi; DPAVB; or any combination thereof:
The emission layer may include a delayed fluorescence material.
In the specification, a delayed fluorescence material may be any compound that is capable of emitting delayed fluorescence, based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may serve as a host or as a dopant, depending on the types of other materials included in the emission layer.
In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be at least 0 eV but not more than 0.5 eV. When a difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is within the range described above, up-conversion from a triplet state to a singlet state of the delayed fluorescence material may effectively occur, and thus, the light-emitting device 10 may have improved luminescence efficiency.
In an embodiment, the delayed fluorescence material may include: a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, etc.); a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B); or the like.
In an embodiment, the delayed fluorescence material may include, for example, at least one of Compounds DF1 to DF14:
The emission layer may include quantum dots.
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 crystals, or according to a ratio of elements in a quantum dot compound.
A diameter of a quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
Quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method that includes mixing a precursor material with an organic solvent and growing quantum dot particle crystals. When the crystals grow, the organic solvent naturally serves as a dispersant coordinated on the surface of the quantum dot crystals and controls the growth of the crystals, so that the growth of quantum dot particles may be controlled through a process which costs less and may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
A quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Examples of a Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, or the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or the like; or any combination thereof.
Examples of a Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, GaAlNP, or the like; a quaternary compound, such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GalnNSb, GaInPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or the like; or any combination thereof. In an embodiment, a Group III-V semiconductor compound may further include a Group II element.
Examples of a Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of a Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, or the like; a ternary compound, such as InGaS3, InGaSe3, or the like; or any combination thereof.
Examples of a Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, AgInSe2, AgGaS, AgGaS2, AgGaSe2, CuInS, CuInS2, CuInSe2, CuGaS2, CuGaSe2, CuGaO2, AgGaO2, AgAlO2, or the like; a quaternary compound, such as AgInGaS2, AgInGaSe2, or the like; or any combination thereof.
Examples of a Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, 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, Ge, and the like; a binary compound, such as SiC, SiGe, and the like; or any combination thereof.
Each element included in a compound, such as a binary compound, a ternary compound, or a quaternary compound, may be present in a particle at a uniform concentration or at a non-uniform concentration. The formulae above refer to the elements included in the compound, wherein a ratio of elements in the compound may vary. For example, AgInGaS2 may represent AgInxGa1-xS2 (where x is a real number between 0 and 1).
In an embodiment, a quantum dot may have a single structure in which the concentration of each element in the quantum dots is uniform, or a quantum dot may have a core-shell structure. For example, a material included in the core and a material included in the shell may be different from each other.
The shell of a quantum dot may serve as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or may serve as a charging layer that imparts electrophoretic characteristics to a quantum dot. The shell may be a single layer or multilayered. An interface between the core and the shell may have a concentration gradient in which the concentration of an element that is present in the shell decreases toward the core.
A shell of a quantum dot may include a metal oxide, a metalloid oxide, a non-metal oxide, a semiconductor compound, or any combination thereof. Examples of a metal oxide, a metalloid oxide, or a non-metal oxide may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, or the like; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, or the like; or any combination thereof.
Examples of a semiconductor compound may include, as described herein: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. For example, the 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 spectrum of a quantum dot may be equal to or less than about 45 nm. For example, a FWHM of an emission spectrum of a quantum dot may be equal to or less than about 40 nm. For example, a FWHM of an emission spectrum of a quantum dot may be equal to or less than about 30 nm. When the FWHM of a quantum dot is within any of these ranges, color purity or color reproducibility of the quantum dot may be improved. Light emitted through a quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
In embodiments, a quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, a nanoplate particle, or the like.
Since an energy band gap may be adjusted by controlling the size of the quantum dots, light having various wavelength bands may be obtained from a quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In an embodiment, the size of the quantum dots or the ratio of elements in a quantum dot compound may be adjusted to emit red light, green light, and/or blue light. In an embodiment, the size of the quantum dots may be configured to emit white light by a combination of light of various colors.
The electron transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple layers including different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the layers of each structure may be stacked from an emission layer in its respective stated order, but the structure of the electron transport region is not limited thereto.
The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
In an embodiment, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11—[(L601)xe1-R601]xe21 [Formula 601]
In Formula 601,
In an embodiment, in Formula 601, when xe11 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.
In an embodiment, in Formula 601, Ar601 may be a substituted or unsubstituted anthracene group.
In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
In Formula 601-1,
In an embodiment, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In an embodiment, the electron transport region may include: one of Compounds ET1 to ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); Alq3; BAlq; TAZ; NTAZ; or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å. For example, the thickness of the electron transport region may be in a range of about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within the ranges described above, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (e.g., an electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion.
A ligand coordinated with a metal ion of an alkali metal complex or with a metal ion of an alkaline earth-metal complex may each independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including 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, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include: an alkali metal oxide, such as Li2O, Cs2O, K2O, or the like; an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI, or the like; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal oxide, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), 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, Lu2Te3, and the like.
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, or a rare earth metal ion; and a ligand bonded to the metal ion (for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof).
In an embodiment, the electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (e.g., an alkali metal halide); or the electron injection layer may consist of an alkali metal-containing compound (e.g., 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, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, or the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the interlayer 130 having a structure as described above. The second electrode 150 may be a cathode, which is an electron injection electrode. When the second electrode 150 is a cathode, a material for forming the second electrode 150 may include 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), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multilayered structure.
The light-emitting device 10 may include a first capping layer arranged outside the first electrode 110, and/or a second capping layer arranged outside the second electrode 150. In embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are 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 the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the stated order.
Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted through the first electrode 110, which may be a transflective electrode or a transmissive electrode, and through the first capping layer to the outside. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted through the second electrode 150, which may be a transflective electrode or a transmissive electrode, and through the second capping layer to the outside.
The first capping layer and the second capping layer may each increase external emission efficiency according to the principle of constructive interference. Accordingly, light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
The first capping layer and the second capping layer may each include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In 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; p-NPB; or any combination thereof:
The heterocyclic compound represented by Formula 1 may be included in various films. Accordingly, another embodiment provides a film including a heterocyclic compound represented by Formula 1. The film may be, for example, an optical member (or a light control means) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflective layer, a light absorbing layer, etc.), a protective member (e.g., an insulating layer, a dielectric layer, etc.), or the like.
The light-emitting device may be included in various electronic apparatuses. For example, an electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one direction in which light emitted from the light-emitting device travels. For example, light emitted from the light-emitting device may be blue light, green light, or white light. Further details on the light-emitting device are the same as described herein. In an embodiment, the color conversion layer may include quantum dots.
The electronic apparatus may include a substrate. The 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 film may be arranged between the subpixels to define each subpixel.
The color filter may further include color filter areas and light-shielding patterns arranged between the color filter areas, and the color conversion layer may further include color conversion areas and light-shielding patterns arranged between the color conversion areas.
The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter areas (or the color conversion areas) may include quantum dots. For example, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include quantum dots. Further details on the quantum dots are the same as described herein. The first area, the second area, and/or the third area may each further include a scatterer.
In an embodiment, the light-emitting device may emit first light, the first area may absorb the first light to emit first-first color light, the second area may absorb the first light to emit second-first color light, and the third area may absorb the first light to emit third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. 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, or the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an 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 arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and simultaneously prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate that includes a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer that includes at least one of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
Various functional layers may be further included on the sealing portion, in addition to the color filter and/or the color conversion layer, according to a use of the electronic apparatus. Examples of 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 using biometric information of a living body (e.g., fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
The electronic apparatus may be applied to various displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
The light-emitting device may be included in various electronic devices.
In an embodiment, an electronic device including the light-emitting device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet 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 luminescence efficiency and long lifespan, and thus, the electronic device including the light-emitting device may have characteristics such as high luminance, high resolution, and low power consumption.
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 arranged on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be arranged on the buffer layer 210. The TFT may include an 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 arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240.
The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 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 arranged 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 may be electrically connected to a light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280.
The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device may be provided on the passivation layer 280. The light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270. The first electrode 110 may be connected (for example, electrically connected) to the exposed portion of the drain electrode 270.
A pixel-defining film 290 including an insulating material may be arranged on the first electrode 110. The pixel-defining film 290 may expose a region of the first electrode 110, and the interlayer 130 may be formed on the exposed region of the first electrode 110. The pixel-defining film 290 may be a polyimide-based organic film or a polyacrylic organic film. Although not shown in
The second electrode 150 may be arranged 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 arranged on the capping layer 170. The encapsulation portion 300 may be arranged 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 (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of the inorganic film and the organic film.
The electronic apparatus (for example, a light-emitting apparatus) of
The functional region 400 may be a color filter area, a color conversion area, or a combination of the color filter area and the color conversion area. In an embodiment, the light-emitting device included in the electronic apparatus of
The electronic device 1, which may be an apparatus that displays a moving image or a still image, 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 notebook, an electronic book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile PC (UMPC), but may also be various products, such as a television, a laptop computer, a monitor, a billboard, or an Internet of things (IOT). The electronic device 1 may be any product as described above or a part thereof.
In an embodiment, 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 a part of the wearable device. However, embodiments are not limited thereto.
Examples of the electronic device 1 may include a dashboard of a vehicle, a center information display (CID) arranged on a center fascia or on a dashboard of a vehicle, a room mirror display that replaces a side mirror of a vehicle, an entertainment display arranged on a rear seat of a vehicle or arranged on the back of a front seat, a head-up display (HUD) installed at 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).
The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. A display device may implement an image through a two-dimensional array of pixels that are arranged in the display area DA.
The non-display area NDA is an area that does not display an image, and may surround (for example, entirely surround) the display area DA. A driver for providing electrical signals or power to display devices arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
In the electronic device 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. In an embodiment, as shown in
In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be greater than the length in the y-axis direction.
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a selected or given direction according to the rotation of at least one wheel. Examples of a vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.
The vehicle 1000 may include a vehicle body having an interior and an exterior, and a chassis that is a portion excluding the vehicle body in which mechanical apparatuses necessary for driving are installed. The exterior of the vehicle body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheels, left and right wheels, and the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on a 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, and the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in the x direction or the −x direction. In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the −x direction. For example, a virtual straight line L connecting the side window glasses 1100 may extend in the x direction or the −x direction. In an embodiment, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In an embodiment, multiple side mirrors 1300 may be provided. For example, one of the side mirrors 1300 may be arranged outside the first side window glass 1110, and another of the side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a tachograph, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center fascia 1500 may be arranged on a side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400, and the center fascia 1500 may be arranged between the cluster 1400 and the passenger seat dashboard 1600. In an embodiment, the cluster 1400 may be arranged to correspond to a driver seat (not shown), and the passenger seat dashboard 1600 may be arranged to correspond to a passenger seat (not shown). In an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, a quantum dot display device, or the like.
Hereinafter, an organic light-emitting display device including the light-emitting device according to an embodiment will be described as an example of the display device 2.
However, various types of display devices as described above may be used in embodiments.
Referring to
Referring to
Referring to
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and the like.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition speed in a range of about 0.01 Å/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 3 to 60 carbon atoms. The term “C1-C60 heterocyclic group” as used herein may be a cyclic group that has 1 to 60 carbon atoms and further has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms in a C1-C60 heterocyclic group may be from 3 to 61.
The term “cyclic group” as used herein may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used herein may be a cyclic group that has 3 to 60 carbon atoms and may not include *—N═*′ as a ring-forming moiety. The term “π electron-deficient nitrogen-containing C1-C60 heterocyclic 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 an embodiment,
The terms “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, and “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of a monovalent C3-C60 carbocyclic group or a monovalent C1-C60 heterocyclic group 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 or 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-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as used herein may be a linear or branched monovalent aliphatic hydrocarbon group that has 1 to 60 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, and the like. The term “C1-C60 alkylene group” as used herein may be a divalent group having a same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at a terminus of a C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and the like. The term “C2-C60 alkenylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at a terminus of a C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and the like. The term “C2-C60 alkynylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein may be a monovalent group represented by —O(A101) (wherein A101 may be a C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
The term “C3-C10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and the like. The term “C3-C10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein may be a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the cyclic structure thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C3-C10 cycloalkenylene group” as used herein may be 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 having 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms, and having at least one carbon-carbon double bond in the cyclic structure thereof. Examples of a C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkyl group.
The term “C6-C60 aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of a C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the respective two or more rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as used herein may be a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms. The term “C1-C60 heteroarylene group” as used herein may be a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms. Examples of a C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, and the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the respective 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 (e.g., having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its molecular structure as a whole. Examples of a monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, and the like. The term “divalent non-aromatic condensed polycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom as ring-forming atoms, and having no aromaticity in its molecular structure 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, a benzothienodibenzothiophenyl group, and the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein may be a group represented by —O(A102) (wherein A102 may be a C6-C60 aryl group), the term “C6-C60 arylthio group” as used herein may be a group represented by —S(A103) (wherein A103 may be a C6-C60 aryl group), and the term “C6-C60 arylseleno group” as used herein may be a group represented by —Se(A108) (wherein A108 may be a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein may be a group represented by -(A104)(A105) (wherein A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as used herein may be a group represented by -(A106)(A107) (wherein A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
In the specification, the group “R10a” may be:
In the specification, Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic 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, and any combination thereof.
In the specification, examples of a “third-row transition metal” may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
In the specification, the term “Ph” refers to a phenyl group, the term “Me” refers to a methyl group, the term “Et” refers to an ethyl group, the terms “ter-Bu” and “But” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
The term “biphenyl group” as used herein may be a “phenyl group substituted with a phenyl group.” For example, a “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein may be a “phenyl group substituted with a biphenyl group.” For example, a “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
In the specification, 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 in an orthogonal coordinate system (for example, a Cartesian coordinate system), and may be interpreted in a broader sense than the aforementioned three axes in an orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may describe axes that are orthogonal to each other, or may describe axes that are in different directions that are not orthogonal to each other.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to the Synthesis Examples and the Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
Under an argon atmosphere, N1,N3-di([1,1′-biphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 21 mmol), N-([1,1′-biphenyl]-3-yl)-N-(3-([1,1′-biphenyl]-3-yloxy)-5-bromophenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (30.7 g, 42 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene. The reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 8-a (white solid, 19 g, 52%).
ESI-LCMS: [M]+: C130H98N402. 1746.7716.
Under an argon atmosphere, Intermediate 8-a (10 g, 5.7 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 8 (yellow solid, 1.2 g, 12%).
ESI-LCMS: [M]+: C130H89B3N4O2. 1770.7371
1H-NMR (CDCl3): δ=8.78 (d, 4H), 8.20 (d, 4H), 8.10 (3, 2H), 7.75 (d, 8H), 7.48 (m, 30H), 7.41 (m, 8H), 7.33 (m, 4H), 7.25 (s, 2H), 7.15 (t, 2H), 7.08 (m, 12H), 6.88 (s, 2H), 6.55 (s, 2H), 1.32 (s, 9H).
Under an argon atmosphere, 5-(tert-butyl)-N1,N3-bis(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (10 g, 13.6 mmol), 9-(3-bromo-5-(phenoxy-2,3,4,5-d4)phenyl)-9H-carbazole-1,2,3,4,5,6,7-d7 (11.6 g, 27.2 mmol), pd2dba3 (0.6 g, 0.7 mmol), tris-tert-butyl phosphine (0.6 mL, 1.4 mmol), and sodium tert-butoxide (4.4 g, 45 mmol) were placed in a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 140° C. for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 17-a (white solid, 10.3 g, 54%).
ESI-LCMS: [M]+: C102H64D22N402. 1420.8114
Under an argon atmosphere, Intermediate 17-a (10 g, 7 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 17 (yellow solid, 1.32 g, 13%).
ESI-LCMS: [M]+: C102H55D22B3N402. 1444.7786
1H-NMR (CDCl3): δ=7.41 (s, 4H), 7.24 (m, 12H), 7.05 (m, 8H), 6.88 (s, 2H), 1.38 (s, 27H).
Under an argon atmosphere, 5-(tert-butyl)-N1,N3-bis(5′-(tert-butyl)-[1,1′: 3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (10 g, 13.6 mmol), 10-(3-bromo-5-(phenylthio)phenyl)-10H-phenothiazine (12.6 g, 27.2 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 24-a (white solid, 11.2 g, 55%).
ESI-LCMS: [M]+: C102H86N4S4. 1494.5744.
Under an argon atmosphere, Intermediate 24-a (10 g, 6.7 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 24 (yellow solid, 1.11 g, 13%).
ESI-LCMS: [M]+: C102H77B3N4S4. 1518.5334
1H-NMR (CDCl3): δ=8.82 (d, 4H), 7.77 (m, 4H), 7.62 (m, 4H), 7.53 (m, 4H), 7.43 (s, 4H), 7.28 (m, 12H), 7.21 (m, 8H), 7.12 (m, 8H), 6.94 (s, 2H), 1.42 (s, 27H).
Under an argon atmosphere, 5-(tert-butyl)-N1,N3-bis(5′-(tert-butyl)-[1,1′: 3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (10 g, 13.6 mmol), 5-([1,1′: 3′,1″-terphenyl]-2′-yl)-10-(3-bromo-5-(phenylthio)phenyl)-5,10-dihydrophenazine (18.4 g, 27.2 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 40-a (white solid, 13 g, 50%).
ESI-LCMS: [M]+: C138H112N6S2. 1916.8114.
Under an argon atmosphere, Intermediate 40-a (10 g, 5.2 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 40 (yellow solid, 1.11 g, 13%).
ESI-LCMS: [M]+: C138H103B3N6S2. 1940.8040
1H-NMR (CDCl3): δ=8.67 (d, 4H), 8.20 (d, 4H), 7.47 (m, 12H), 7.41 (t, 2H), 7.35 (d, 2H), 7.28 (m, 12H), 7.23 (m, 2H), 7.12 (m, 8H), 7.05 (m, 8H), 6.99 (s, 2H), 6.88 (m, 16H), 1.42 (s, 18H), 1.23 (s, 9H)
Under an argon atmosphere, 5-(tert-butyl)-N1,N3-bis(5′-(tert-butyl)-[1,1′: 3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (10 g, 13.6 mmol), 9-(3-bromo-5-(phenoxy-2,3,4,5-d4)phenyl)-9H-4,9′-bicarbazole-2,3,5,6,7,8-d6 (16 g, 27.2 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 67-a (white solid, 11 g, 49%).
ESI-LCMS: [M]+: C118H64D20N602. 1636.1312.
Under an argon atmosphere, Intermediate 67-a (10 g, 6.1 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 67 (yellow solid, 1.2 g, 12%).
ESI-LCMS: [M]+: C118H55D20B3N602. 1660.7574
1H-NMR (CDCl3): δ=8.55 (d, 4H), 8.20 (d, 4H), 7.55 (m, 4H), 7.44 (s, 2H), 7.37 (m, 4H), 7.21 (m, 2H), 7.15 (m, 12H), 7.01 (m, 8H), 6.88 (s, 2H), 1.26 (s, 9H)
Under argon atmosphere, N1,N3-bis(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)-5-(dibenzo[b,d]furan-4-yl)benzene-1,3-diamine (10 g, 11.8 mmol), 3,3″-((5-iodo-1,3-phenylene)bis(oxy))di-1,1′-biphenyl (13 g, 23.7 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 87-a (white solid, 10.3 g, 52%).
ESI-LCMS: [M]+: C122H94N205. 1666.7213.
Under an argon atmosphere, Intermediate 87-a (10 g, 6 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 87 (yellow solid, 1.7 g, 20%).
ESI-LCMS: [M]+: C122H85B3N205. 1690.6727
1H-NMR (CDCl3): δ=8.08 (m, 3H), 7.91 (s, 4H), 7.88 (s, 4H), 7.80 (m, 8H), 7.63 (m, 12H), 7.55 (m, 8H), 7.43 (m, 12H), 7.13 (m, 8H), 6.93 (s, 2H), 6.55 (s, 2H), 1.43 (s, 18H), 1.32 (s, 9H)
Under an argon atmosphere, N1,N3-di([1,1′:3′,1″-terphenyl]-2′-yl)-5-(tert-butyl)benzene-1,3-diamine (10 g, 16 mmol), 9-(3-(([1,1′-biphenyl]-4-yl-2,3,5,6-d4)oxy)-5-iodophenyl)-3,6-diphenyl-9H-carbazole-1,2,4,5,7,8-d6 (22.5 g, 32.2 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 89-a (white solid, 13.8 g, 49%).
ESI-LCMS: [M]+: C130H74D20N402. 1762.8661.
Under an argon atmosphere, Intermediate 89-a (13 g, 7.4 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 89 (yellow solid, 2.37 g, 17%).
ESI-LCMS: [M]+: C130H69D16B3N402. 1782.8011
1H-NMR (CDCl3): δ=7.51 (m, 4H), 7.43 (m, 12H), 7.40 (m, 2H), 7.22 (m, 20H), 7.08 (m, 8H), 6.88 (s, 2H), 6.52 (s, 2H), 1.29 (s, 9H)
Under an argon atmosphere, 5-(tert-butyl)-N1,N3-bis(5′-(tert-butyl)-[1,1′: 3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (10 g, 13.6 mmol), 3,3″-((5-iodo-1,3-phenylene)bis(oxy))di-1,1′-biphenyl (14.7 g, 27.2 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (11.5 g, 120 mmol) were placed in a 2 L flask and dissolved in 300 mL of o-xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added thereto for extraction, and an organic layer was collected therefrom, dried using MgSO4, and filtered. The filtered solution was subjected to reduced pressure to remove the solvent therefrom, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Intermediate 101-a (white solid, 11 g, 52%).
ESI-LCMS: [M]+: C114H96N204. 1556.7440.
Under an argon atmosphere, Intermediate 101-a (11 g, 7 mmol) was placed in a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BBr3 (3 equiv.) was added thereto. The reaction solution was stirred at 140° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel using CH2Cl2 and hexane as developing solvents to obtain Compound 101 (yellow solid, 2.23 g, 20%).
=ESI-LCMS: [M]+: C114H87B3N2O4. 1580.6974
1H-NMR (CDCl3): δ=7.99 (s, 4H), 7.89 (d, 4H), 7.75 (d, 4H), 7.62 (i, 16H), 7.43 (i, 12H), 7.08 (s, 8H), 7.00 (s, 2H), 6.58 (m, 2H), 1.37 (s, 18H), 1.29 (s, 9H)
1H-NMR (CDCl3)
For compounds of Examples 1 to 8 and Comparative Examples 1 to 4, the HOMO energy level, absorption wavelength (AAbs) in a solution phase, emission wavelength (λemi) in a solution phase, difference between the maximum wavelength when absorbing energy and the maximum wavelength when emitting energy (Stokes-shift), luminescence efficiency (photoluminescence quantum yield, PLQY), and delayed fluorescence rate (delayed fluorescence lifespan, TD) were measured, and the results are shown in Table 2.
The ΔAbs was measured using the LabSolutions UV-Vis software on the UV-1800 UV/visible scanning spectrophotometer equipment available from Shimadzu Ltd., on which a deuterium/tungsten-halogen light source and a silicon photodiode were mounted. The λemi was measured using the FluorEssence software on the FluoroMax+spectrometer equipment available from Horiba Ltd., on which a xenon light source and a monochromator were mounted. The HOMO energy level was measured using the Smart Manager software on the SP2 electrochemical workstation equipment available from Zive Lab Ltd. The PLQY was measured using the PLQY measurement software on the Quantaurus-QY Absolute PL quantum yield spectrometer equipment available from Hamamatsu Ltd., on which a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere were mounted. The TD was measured at 300 K using the fluorescence lifespan measurement device C11367-01 available from Hamamatsu Ltd.
TD
Referring to Table 2, it was confirmed that the dopant compounds of Examples 1 to 8 had a deep HOMO energy level and a narrow Stokes-shift value and exhibited fast delayed fluorescence equal to or less than 20 μs, thereby having high TADF properties.
As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2 (1,200 Å) ITO electrode formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated by using isopropyl alcohol and pure water each for 5 minutes, cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and mounted on a vacuum deposition apparatus.
NPD was deposited on the anode to form a hole injection layer having a thickness of 300 Å, Compound HT6 was deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å, and CzSi was deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å.
A host mixture, in which Compound HTH53 and Compound ETH66, each according to an embodiment, were mixed at a weight ratio of 1:1, Compound PD33, and an Example compound or a Comparative Example compound were co-deposited thereon at a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å. TSPO1 was deposited on the emission layer to form a hole blocking layer having a thickness of 200 Å. TPBi was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, and LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al was deposited thereon to form a second electrode having a thickness of 3,000 Å, thereby forming a LiF/Al electrode. Compound HT28 was deposited on the second electrode to form a capping layer having a thickness of 700 Å. Each layer was formed by vacuum deposition.
Light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, for use as a host, a sensitizer, and a dopant, the corresponding compounds shown in Table 3 were used.
For the light-emitting devices of Examples 1 to 8 and Comparative Examples 1 to 4, the device efficiency and device lifespan were evaluated, and the results are shown in Table 3. The driving voltage and current density were measured using the V7000 OLED IVL test system (PolarOnix Inc.). To evaluate the characteristics of the manufactured light-emitting devices, the driving voltage and efficiency (cd/A/y) at a current density of 10 mA/cm2 were measured. The driving voltage (V), luminous efficacy (Cd/A), and emission wavelength at a luminance of 1000 cd/m2 were measured using Keithley MU 236 and a luminance meter PR650, respectively. In evaluating the relative device lifespan, the time taken for the luminance to deteriorate to 95% of the initial value when each light-emitting device was continuously driven at the current density of 10 mA/cm2 was measured and compared with the time measured in Comparative Example 1.
Referring to Table 3, it was confirmed that the light-emitting devices according to Examples 1 to 8 had low driving voltage, high top-emission efficiency, long lifespan, and high color purity characteristics, as compared with the light-emitting devices according to Comparative Examples 1 to 4.
According to the embodiments, a light-emitting device may include a heterocyclic compound represented by Formula 1, thereby having excellent characteristics such as low driving voltage, high top-emission efficiency, long lifespan, and high color purity, and a high-quality electronic apparatus and electronic device may be manufactured by using the light-emitting device.
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 |
|---|---|---|---|
| 10-2024-0005475 | Jan 2024 | KR | national |
