Patent Application
20250127056
This application claims priority under to and benefits of Korean Patent Application No. 10-2023-0093954 under 35 U.S.C. § 119, filed on Jul. 19, 2023, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to a light-emitting device including a heterocyclic compound, an electronic apparatus including the light-emitting device, and electronic equipment including the light-emitting device.
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 holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.
It is to be understood that this background of the technology section is, in part, intended to provide useful background for understanding the technology. However, this background of the technology section may also include ideas, concepts, or recognitions that were not part of what was known or appreciated by those skilled in the pertinent art prior to a corresponding effective filing date of the subject matter disclosed herein.
Embodiments include a light-emitting device including a heterocyclic compound, an electronic apparatus including the light-emitting device, and electronic equipment including the light-emitting device.
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 Formulae 1 to 4,
According to an embodiment, at least one of R4 groups in the number of a4, R5 groups in the number of a5, and R6 groups in the number of a6 may each independently be a group represented by Formula 4.
According to an embodiment, ring CY1 to ring CY3 and ring CY6 to ring CY8 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a pyridine group, a pyrimidine group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, a dinaphthothiophene group, a selenophene group, a benzoselenophene group, a dibenzoselenophene group, naphthoselenophene group, a benzonaphthoselenophene group, or a dinaphthoselenophene group.
According to an embodiment, ring CY4 and ring CY5 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, or a chrysene group.
According to an embodiment, R1 to R6 may each independently be a group represented by Formula 4, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2), or —N(Q1)(Q2).
According to an embodiment, at least one of R1 groups in the number of a1 and R2 groups in the number of a2 may each independently be a group represented by Formula 4.
According to an embodiment, the group represented by Formula 4 may be a group represented by one of Formulae 4-1 to 4-6, which are explained below.
According to an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 1-1, which is explained below.
According to an embodiment, the heterocyclic compound represented by Formula 2 may be a compound represented by Formula 2-1, which is explained below.
According to an embodiment, the heterocyclic compound represented by Formula 1 may be one of Compounds A1 to A80, which are explained below.
According to an embodiment, the heterocyclic compound represented by Formula 2 may be one of Compounds B1 to B20, which are explained below.
According to an embodiment, the emission layer may further include a sensitizer.
According to an embodiment, the host may further include a compound that is different from the heterocyclic compound represented by Formula 2.
According to an embodiment, the emission layer may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 490 nm.
According to an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
According to an embodiment, the light-emitting device may further include: a first capping layer outside the first electrode; or a second capping layer outside the second electrode.
According to embodiments, an electronic apparatus may include the light-emitting device.
According to an embodiment, the electronic apparatus may further include: a thin-film transistor electrically connected to the light-emitting device; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
According to embodiments, an electronic equipment may include the light-emitting device.
According to an embodiment, the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purpose of limitation, and the disclosure is not limited to the embodiments described above.
The above and other aspects and features of the disclosure will be more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:
The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like reference numbers and/or like reference characters refer to like elements throughout.
In the description, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.
In the description, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.
As used herein, the expressions used in the singular such as “a,” “an,” and “the,” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.
In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group consisting of” for the purpose of its meaning and interpretation. For example, “at least one of A, B, and C” may be understood to mean A only, B only, C only, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.
It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.
The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.
It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.
According to embodiments, a light-emitting device may include:
In Formula 1, Ar1 and Ar2 may each independently be a group represented by Formula 3.
In an embodiment, Ar1 and Ar2 may be identical to or different from each other.
In Formulae 1, 2, and 4, ring CY1 to ring CY3 and ring CY6 to ring CY8 may each independently be a C5-C60 carbocyclic group or a C2-C60 heterocyclic group.
In an embodiment, ring CY1 to ring CY3 and ring CY6 to ring CY8 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a pyridine group, a pyrimidine group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, a dinaphthothiophene group, a selenophene group, a benzoselenophene group, a dibenzoselenophene group, naphthoselenophene group, a benzonaphthoselenophene group, or a dinaphthoselenophene group.
In Formula 2, ring CY4 and ring CY5 may each independently be a C5-C60 carbocyclic group.
In an embodiment, ring CY4 and ring CY5 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, or a chrysene group. In an embodiment, ring CY4 and ring CY5 may each independently be a benzene group or a naphthalene group.
In Formulae 1, 2, and 4, a1 to a8 may each independently be an integer from 0 to 10.
In Formulae 1 and 2, R1 to R6 may each independently be a group represented by Formula 4, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl seleno group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group that is unsubstituted or substituted with at least one R10a, a C6-C60 heteroaryl seleno group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2).
In an embodiment, R1 to R6 may each independently be a group represented by Formula 4, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2), or —N(Q1)(Q2).
In an embodiment, at least one of R4 groups in the number of a4, R5 groups in the number of a5, and R6 groups in the number of a6 may each independently be a group represented by Formula 4.
In an embodiment, at least one of R1 groups in the number of a1 and R2 groups in the number of a2 may each independently be a group represented by Formula 4.
In Formulae 3 and 4, R7, R8, and R901 to R913 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group that is unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl seleno group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group that is unsubstituted or substituted with at least one R10a, a C6-C60 heteroaryl seleno group that is unsubstituted or substituted with at least one R10a, a non-aromatic condensed polycyclic group that is unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2).
In Formulae 1 to 4, two or more groups among R1 to R3, R6 to R8, and R901 to R913 may optionally be bonded together to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, R901 to R913 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a C1-C30 alkyl group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), or —Ge(Q1)(Q2)(Q3).
In an embodiment, at least one of R901 to R913 may be a tert-butyl group that is unsubstituted or substituted with at least one R10a.
In Formulae 1 to 4, R10a may be:
In an embodiment, the group represented by Formula 4 may be a group represented by one of Formulae 4-1 to 4-6:
In Formulae 4-1 to 4-6, X71 may be C(R71) or N, X72 may be C(R72) or N, X73 may be C(R73) or N, X74 may be C(R74) or N, X81 may be C(R81) or N, X82 may be C(R82) or N, X83 may be C(R83) or N, X84 may be C(R84) or N, X85 may be C(R85) or N, and X86 may be C(R86) or N.
In an embodiment, X71 may be C(R71), X72 may be C(R72), X73 may be C(R73), X74 may be C(R74), X81 may be C(R81), X82 may be C(R82), X83 may be C(R83), X84 may be C(R84), X85 may be C(R85), and X86 may be C(R86).
In Formulae 4-1 to 4-6, Y4 may be C(R87)(R88), N(R89), O, or S.
In Formulae 4-1 to 4-6, R71 to R74 may each independently be the same as described in connection with R7 in Formula 4, and R81 to R89 may each independently be the same as described in connection with R8 in Formula 4, and
In an embodiment, R87 and R88 may optionally be bonded together to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a. In an embodiment, R87 and R88 may optionally be bonded together to form a fluorene group that is unsubstituted or substituted with at least one R10a.
In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 1-1.
In Formula 1-1,
In an embodiment, the heterocyclic compound represented by Formula 2 may be a compound represented by Formula 2-1:
In Formula 2-1,
In an embodiment, the heterocyclic compound represented by Formula 1 may be one of Compounds A1 to A80:
In an embodiment, the heterocyclic compound represented by Formula 2 may be one of Compounds B1 to B20:
Because Ar1 and Ar2 may each independently be a group represented by Formula 3, the heterocyclic compound represented by Formula 1 significantly suppresses Dexter energy transfer efficiency and inhibits aggregation caused by intermolecular interactions, by physically increasing the intermolecular distance from other neighboring molecules. Therefore, the density of triplet excitons in the molecule may be reduced, and device lifespan may be improved when the heterocyclic compound represented by Formula 1 is employed in a light-emitting device. The luminescence efficiency of the device may be improved by suppressing generation of transition compounds such as excimers and/or exciplexes between molecules.
The heterocyclic compound represented by Formula 2 may improve the efficiency of a device because the heterocyclic compound represented by Formula 2 inhibits formation of excimers and/or exciplexes with neighboring common layer molecules due to a steric hindrance effect of a carbazole group. Because the introduction of a carbazole group leads to a small ΔEST, the reverse intersystem crossing (RISC) rate of triplet excitons is greatly improved, and thus, the lifespan of a host including the heterocyclic compound represented by Formula 2 may be improved. The heterocyclic compound represented by Formula 2 may have a deep highest occupied molecular orbital (HOMO) energy level by including a carbazole group.
In an embodiment wherein a light-emitting device in which the heterocyclic compound represented by Formula 1 is used as a dopant and the heterocyclic compound represented by Formula 2 is used as a host, the HOMO energy levels of the host and the dopant are well matched, thereby improving the efficiency and lifespan of a device, and an emission wavelength of the host and an absorption wavelength of the dopant are well matched, thereby greatly increasing the efficiency of Forster resonance energy transfer (FRET) and thus improving the efficiency of a device.
Therefore, when the heterocyclic compound represented by Formula 1 is used as a dopant and the heterocyclic compound represented by Formula 2 is used as a host, a light-emitting device may have low driving voltage, high efficiency, high color purity, and long lifespan.
In an embodiment, the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may each be a delayed fluorescence material.
In an embodiment, the emission layer in the light-emitting device may further include a sensitizer.
In an embodiment, the host of the light-emitting device may further include a compound that is different from the heterocyclic compound represented by Formula 2.
In an embodiment, the emission layer of the light-emitting device may emit blue light having a maximum emission wavelength in a range of about 400 nm to about 500 nm. For example, the emission layer of the light-emitting device may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 490 nm.
In an embodiment, the first electrode of the light-emitting device may be an anode, and the second electrode of the light-emitting device may be a cathode,
In an embodiment, the light-emitting device may further include: a first capping layer outside the first electrode; or a second capping layer outside the second electrode.
The term “interlayer” as used herein may refer to a single layer and/or all layers between the first electrode and the second electrode of the light-emitting device.
According to embodiments, an electronic apparatus may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. 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. A detailed description of the electronic apparatus is provided herein.
According to embodiments, an electronic equipment may include the light-emitting device.
In an embodiment, the electronic equipment may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
Hereinafter, a structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 are described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates the injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. 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 semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. In an embodiment, 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 the emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound such as a heterocyclic compound, an inorganic material such as quantum dots, 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 which may each be located between adjacent units among the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the at least one charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, or a structure including multiple layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
In an embodiment, the hole transport region may have a multilayer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in its respective stated order, but the structure of the hole transport region is not limited thereto.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In 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 as described herein.
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), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be 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 these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy of the p-dopant may be less than or equal to about −3.5 eV.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including an element EL1 and an element EL2, or any combination thereof.
Examples of a quinone derivative may include TCNQ and F4-TCNQ.
Examples of a cyano group-containing compound may include HAT-CN and a compound represented by Formula 221.
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Examples of a metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of a metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of a non-metal may include oxygen (O) and a halogen (for example, F, Cl, Br, I, etc.).
Examples of a compound including element EL1 and element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (for example, 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 (for example, WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and a rhenium oxide (for example, ReO3, etc.).
Examples of a metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.
Examples of an alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, Kl, RbI, and CsI.
Examples of an alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
Examples of a transition metal halide may include a titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), a vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), a molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), a manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (for example, TcF2, TcCl2, TcBr2, Tcl2, etc.), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (for example, CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of a post-transition metal halide may include a zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (for example, InI3, etc.), and a tin halide (for example, SnI2, etc.).
Examples of a lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
Examples of a metalloid halide may include an antimony halide (for example, SbCl5, etc.).
Examples of a metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
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 an embodiment, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials may be mixed with each other in a single layer, to emit white light.
The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
An amount of the dopant in the emission layer may be in a range of about 0.01 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.
The emission layer may further include, in addition to the heterocyclic compound, a host, a dopant, a sensitizer, a delayed fluorescence material, or any combination thereof. Each of the host, the dopant, the sensitizer, the delayed fluorescence material, or any combination thereof may include at least one deuterium.
In an embodiment, the emission layer may include a host, and the host may include a compound that is different from the heterocyclic compound represented by Formula 2. The host may include an electron-transporting compound, a hole-transporting compound, a bipolar compound, or any combination thereof. The host may not include a metal. The electron-transporting compound, the hole-transporting compound, and the bipolar compound may be different from each other.
In an embodiment, the emission layer may include a host, and the host may include an electron-transporting compound and a hole-transporting compound.
In an embodiment, the electron-transporting compound and the hole-transporting compound may form an exciplex.
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.
The host may further include a compound that is different from the heterocyclic compound represented by Formula 2.
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 together 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 (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In an embodiment, the host may include one of Compounds H1 to H124, 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 first host compound and a second host compound.
In an embodiment, the first host compound may be a hole-transporting host.
In an embodiment, the second host compound may be an electron-transporting host.
In the specification, a hole-transporting host may be a compound that includes a hole-transporting moiety.
In the specification, an electron-transporting host may be a compound that includes an electron-transporting moiety or a compound having bipolar properties.
In the specification, the terms “hole-transporting host” and “electron-transporting host” may each be understood according to a relative difference between hole mobility and electron mobility in the hole-transporting host and the electron-transporting host. For example, even when an electron-transporting host does not include an electron-transporting moiety, a bipolar compound exhibiting relatively higher electron mobility than the hole-transporting host may be also understood as an electron-transporting host.
In an embodiment, a hole-transporting host may be represented by one of Formulae 311-1 to 311-6, and an electron-transporting host may be represented by one of Formulae 312-1 to 312-4 and 313.
In Formulae 311-1 to 311-6, 312-1 to 312-4, 313, and 313A,
In an embodiment, the first host compound and the second host compound may form an exciplex.
In an embodiment, the emission layer may further include a phosphorescent dopant.
In an embodiment, the emission layer may further include a phosphorescent dopant, and the phosphorescent dopant may serve as a sensitizer.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
In an embodiment, the phosphorescent dopant may be an organometallic compound.
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 ring A401 among two or more of L401 may be optionally linked together via T402, which is a linking group, and two ring A402 may be optionally linked together 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 as defined herein.
In Formula 401, L402 may be an organic ligand. In an embodiment, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one of Compounds PD1 to PD41, or any combination thereof:
In an embodiment, the emission layer may further include a fluorescent dopant.
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
In Formula 501,
In an embodiment, in Formula 501, Ar501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed together.
In an embodiment, in Formula 501, xd4 may be 2.
In an embodiment, the fluorescent dopant may include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
In an embodiment, the emission layer may further include a delayed fluorescence material.
In the specification, a delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may serve as a host or as a dopant, depending on the types of other materials included in the emission layer.
In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be in a range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is satisfied within the range as described above, up-conversion from a triplet state to a singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be increased.
In an embodiment, the delayed fluorescence material may include: a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, or the like); or a material including a C8-C60 polycyclic group including at least two cyclic groups that are condensed with each other while sharing boron (B).
Examples of a delayed fluorescence material may include at least one of Compounds DF1 to DF9:
In an embodiment, 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 crystal.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material with an organic solvent and growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally serves as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a process which costs less, and may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
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, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
Examples of a Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, a Group III-V semiconductor compound may further include a Group II element. Examples of a Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, and InAlZnP.
Examples of a Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3 or InGaSe3; or any combination thereof.
Examples of a Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or any combination thereof.
Examples of a Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
Examples of a Group IV element or compound may include: a single element material, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
Each element included in a multi-element compound, such as a binary compound, a ternary compound, or a quaternary compound, may be present in a particle at a uniform concentration or at a non-uniform concentration.
In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. In an embodiment, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may serve as a protective layer that prevents chemical denaturation of the core to maintain semiconductor characteristics, and/or may serve as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be single layered or multilayered. An interface between the core and the shell may have a concentration gradient in which the concentration of a material that is present in the shell decreases toward the core.
Examples of a material forming the shell of the 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, or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; or any combination thereof.
Examples of a semiconductor compound may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group 1-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. In an embodiment, 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.
The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the quantum dot is within any of these ranges, color purity or color reproducibility may be increased. Light emitted through the quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
In an embodiment, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, or a cubic particle, or the quantum dot may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.
Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various wavelength bands may be obtained from the 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 dot may be selected to emit red light, green light, and/or blue light. The size of the quantum dot may be configured to emit white light by 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 the emission layer in its respective stated order, but the structure of the electron transport region is not limited thereto.
In an embodiment, the electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one rr electron-deficient nitrogen-containing C1-C60 cyclic 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 together 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 be 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 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 thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, an electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of an 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 an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion.
A ligand coordinated with a metal ion of an alkali metal complex or an alkaline earth-metal complex may each independently include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer including different materials, 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 (for example, 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, or K2O; an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), or BaxCa1-xO (wherein x is a real number satisfying 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, Scl3, Tbl3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of a lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include: an alkali metal ion, an alkaline earth metal ion, or a rare earth metal ion; and a ligand bonded to the metal ion (for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof).
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 (for example, a compound represented by Formula 601).
In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (for example, an alkali metal halide); or the electron injection layer may consist of an alkali metal-containing compound (for example, an alkali metal halide), and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a Kl: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 as 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. 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 semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multilayer structure.
The light-emitting device 10 may include a first capping layer outside the first electrode 110 and/or a second capping layer outside the second electrode 150. In an embodiment, 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 this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order.
Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first capping layer. Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and through the second capping layer.
The first capping layer and the second capping layer may each increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, such that the luminescence efficiency of the light-emitting device 10 may be increased.
The first capping layer and the second capping layer may each include a material having a refractive index greater than or equal to 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 each 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, β-NPB, or any combination thereof:
The heterocyclic compound represented by Formula 1 or the heterocyclic compound represented by Formula 2 may be included in various films. Therefore, embodiments provide a film which may include a heterocyclic compound represented by Formula 1 and/or a heterocyclic compound represented by Formula 2. The film may be, for example, an optical member (or a light control means) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, or the like), or a protective member (for example, an insulating layer, a dielectric layer, or the like).
The light-emitting device may be included in various electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and the like.
The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one traveling direction of light emitted from the light-emitting device. In an embodiment, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, a quantum dot as described herein.
The electronic apparatus may include a first substrate. The first substrate may include subpixels, the color filter may include color filter areas respectively corresponding to the subpixels, and the color conversion layer may include color conversion areas respectively corresponding to the subpixels.
A pixel-defining 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 from one another. In an embodiment, 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. In an embodiment, 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. The quantum dots may be 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 a 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 from one another. In an embodiment, 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, and the like.
The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer, and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and may simultaneously prevent ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
Various functional layers may be further included on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the 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 further include, in addition to the light-emitting device as described above, a biometric information collector. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (for example, fingertips, pupils, etc.).
The electronic apparatus may be applied to various displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
The electronic apparatus (e.g., 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 140 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 the light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a region of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed region 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 located on the capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or any combination thereof; or a combination of the inorganic film and the organic film.
The electronic apparatus of
The electronic equipment 1, which may be an apparatus that displays a moving image or a still image, may not only be a portable electronic equipment, such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile PC(UMPC), but may also be various products, such as a television, a laptop, a monitor, a billboard, or an Internet of things (IOT). The electronic equipment 1 may be any product as described above or a part thereof.
The electronic equipment 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type display, or a head mounted display (HMD), or a part of the wearable device. However, embodiments are not limited thereto.
For example, the electronic equipment 1 may be a dashboard of a vehicle, a center fascia of a vehicle, a center information display arranged on a dashboard of a vehicle, a room mirror display that replaces a side-view mirror of a vehicle, an entertainment display for a rear seat of a vehicle or arranged on the back of a front seat, a head up display (HUD) installed in the front of a vehicle or projected on a front window glass, or a computer generated hologram augmented reality head up display (CGH AR HUD).
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A display apparatus may implement an image through a two-dimensional array of pixels that are arranged in the display area DA.
The non-display area NDA may be an area that does not display an image, and may surround (e.g., 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 equipment 1, a length in an x-axis direction and a length in a y-axis direction may be different from each other. In an embodiment, as shown in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a selectable direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover 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 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-view mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on a side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. Multiple side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400 and the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in an x direction or a −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, an imaginary straight line L connecting the side window glasses 1100 may extend in the x direction or the −x direction. In an embodiment, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side-view mirror 1300 may provide a rear view of the vehicle 1000. The side-view mirror 1300 may be installed on the exterior of the body. In an embodiment, multiple side-view mirrors 1300 may be provided. One of the side-view mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the side-view mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of a steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, 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 may be disposed. The center fascia 1500 may be arranged on a side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. 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 apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In an embodiment, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display, an inorganic EL display, or a quantum dot display. Hereinafter, an organic light-emitting display apparatus including the light-emitting device according to an embodiment will be described as an example of the display apparatus 2. However, various types of display apparatuses as described herein 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 respective layers included in the hole transport region, the emission layer, and the respective layers included in the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as used herein may be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as used herein may be a cyclic group that has one to sixty carbon atoms and may further include, in addition to carbon atoms, 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, a C1-C60 heterocyclic group may have 3 to 61 ring-forming atoms.
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 three to sixty carbon atoms and may not include *—N═*′ as a ring-forming moiety. The term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein may be a heterocyclic group that has one to sixty carbon atoms and may include *—N═*′ as a ring-forming moiety.
In an embodiment,
a π electron-rich C3-C60 cyclic group may be a T1 group, a group in which two or more T1 groups are condensed with each other, a T3 group, a group in which two or more T3 groups are condensed with each other, or a group in which at least one T3 group and at least one T1 group are condensed with each other (for example, a C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, or the like), and
a π electron-deficient nitrogen-containing C1-C60 cyclic group may be a T4 group, a group in which two or more T4 groups are condensed with each other, a group in which at least one T4 group and at least one T1 group are condensed with each other, a group in which at least one T4 group and at least one T3 group are condensed with each other, or a group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and the like),
The terms “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, or “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.), according to the structure of a formula for which the corresponding term is used. In an embodiment, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by those 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-C1 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C1 cycloalkenylene group, a C1-C1 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 aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-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, and a butenyl group. The term “C2-C60 alkenylene group” as used herein may be a divalent group having a same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at a terminus of a C2-C60 alkyl group, and examples thereof may include an ethynyl group and a propynyl group. 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, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having three to ten 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, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkyl group.
The term “C1-C1 heterocycloalkyl group” as used herein may be a monovalent cyclic group that has one to ten carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein may be a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the cyclic structure thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein may be a divalent group having a same structure as the C3-C10 cycloalkenyl group.
The term “C1-C1 heterocycloalkenyl group” as used herein may be a monovalent cyclic group that has one to ten carbon atoms, further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom, and has at least one double bond in the cyclic structure thereof. Examples of a C1-C1 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein may be a divalent group having a same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system of six to sixty carbon atoms, and the term “C6-C60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system of six to sixty 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, and an ovalenyl group. 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 that has one to sixty carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom. The term “C1-C60 heteroarylene group” as used herein may be a divalent group having a heterocyclic aromatic system that has one to sixty carbon atoms and further includes, in addition to the carbon atoms, at least one heteroatom as a ring-forming atom. 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, and a naphthyridinyl group. 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 having two or more rings condensed with each other, only carbon atoms (for example, eight to sixty carbon atoms) as ring-forming atoms, and no aromaticity in its molecular structure when considered 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, and an indeno anthracenyl group. 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 that has two or more rings condensed with each other, further includes, in addition to carbon atoms (for example, one to sixty carbon atoms), at least one heteroatom as a ring-forming atom, and has no aromaticity in its molecular structure when considered as a whole. Examples of a monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as 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), and the term “C6-C60 arylthio group” as used herein may be a group represented by —S(A103) (wherein A103 may be a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein may be a group represented by -(A104)(A105) (wherein A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as used herein may be a group represented by -(A106)(A107) (wherein A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
In the specification, the group “R10a” may be:
In the specification, the groups 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 phenyl group, a biphenyl group, or any combination thereof.
The term “heteroatom” as used herein may be any atom other than a carbon atom or a hydrogen atom. Examples of a heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
In the specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “ter-Bu” or “But” each refer to a tert-butyl group, and “OMe” refers to a methoxy group.
The term “biphenyl group” as used herein may be a “phenyl group that is substituted with a phenyl group.” For example, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The “terphenyl group” as used herein may be a “phenyl group that is substituted with a biphenyl group”. For example, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group that is substituted with a C6-C60 aryl group.
In the specification, the terms “x-axis”, “y-axis”, and “z-axis” are not limited to three axes in an orthogonal coordinate system (e.g., 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.
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.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to the following Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
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, 13.5 mmol), 1-chloro-3-iodobenzene-2,4,5,6-d4 (6.6 g, 27 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A3-1 (white solid, 10 g, 77%).
ESI-LCMS: [M]+: C66H56D6Cl2N2. 958.4711.
Under an argon atmosphere, Intermediate Compound A3-1 (10 g, 10 mmol) was put into a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BBr3 (1.5 equiv.) was added thereto. The reaction solution was stirred 180° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A3-2 (yellow solid, 2.4 g, 24%).
ESI-LCMS: [M]+: C66H53D6BCl2N2. 966.4532
Under an argon atmosphere, Intermediate Compound A3-2 (2.4 g, 2.5 mmol), 9H-carbazole-1,2,4,5,6,7,8-d7 (0.9 g, 5 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A3 (yellow solid, 1.7 g, 72%).
ESI-LCMS: [M]+: C90H53D22BN4. 1244.7475
1H-NMR (CDCl3): d=7.43 (s, 4H), 7.22 (m, 12H), 7.09 (m, 8H), 6.88 (s, 2H), 1.32 (s, 18H), 1.12 (s, 9H)
Under an argon atmosphere, Intermediate Compound A3-2 (2.4 g, 2.5 mmol), 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (1.3 g, 5 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A9 (yellow solid, 2.6 g, 75%).
ESI-LCMS: [M]+: C102H53D30BN4. 1404.8661
1H-NMR (CDCl3): d=7.47 (s, 4H), 7.17 (m, 12H), 7.06 (m, 8H), 6.92 (s, 2H), 1.36 (s, 18H), 1.19 (s, 9H)
Under an argon atmosphere, N1,N3-bis(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)-5-(methyl-d3)benzene-1,3-diamine (10 g, 14.4 mmol), 1-chloro-3-iodobenzene (6.9 g, 28.8 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A22-1 (white solid, 9.7 g, 74%).
ESI-LCMS: [M]+: C63H53D3Cl2N2. 913.4130.
Under an argon atmosphere, Intermediate Compound A22-1 (9.7 g, 10 mmol) was put into a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BBr3 (1.5 equiv.) was added thereto. The reaction solution was stirred 180° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A22-2 (yellow solid, 2.44 g, 25%).
ESI-LCMS: [M]+: C63H50D3BCl2N2. 1183.8008
Under an argon atmosphere, Intermediate Compound A22-2 (2.4 g, 2.6 mmol), 9H-carbazole (0.87 g, 5.2 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A22 (yellow solid, 2.4 g, 77%).
ESI-LCMS: [M]+: C87H66D3BN4. 1183.5821
1H-NMR (CDCl3): d=8.88 (d, 2H), 8.55 (d, 4H), 7.94 (d, 4H), 7.77 (d, 4H), 7.56 (d, 4H), 7.41 (s, 4H), 7.35 (d, 2H), 7.24 (s, 2H), 7.20 (m, 12H), 7.12 (m, 8H), 6.91 (s, 2H), 1.36 (s, 18H).
Under an argon atmosphere, N3,N5-bis(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)-[1,1′-biphenyl]-2′,3′,4′,5′,6′-d5-3,5-diamine (10 g, 13.2 mmol), 1-chloro-3-iodobenzene (6.3 g, 26.4 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A28-1 (white solid, 10 g, 78%).
ESI-LCMS: [M]+: C68H53D5C12N2. 977.0043.
Under an argon atmosphere, Intermediate Compound A28-1 (10 g, 10 mmol) was put into a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BBr3 (1.5 equiv.) was added thereto. The reaction solution was stirred 180° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A28-2 (yellow solid, 3.9 g, 39%).
ESI-LCMS: [M]+: C68H50D5BCl2N2. 985.4137
Under an argon atmosphere, Intermediate Compound A28-2 (3.9 g, 3.9 mmol), 9H-carbazole (1.4 g, 7.8 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A28 (yellow solid, 3.4 g, 71%).
ESI-LCMS: [M]+: C92H66D5BN4. 1247.6017
1H-NMR (CDCl3): d=8.75 (d, 2H), 8.48 (d, 4H), 7.90 (d, 4H), 7.73 (d, 4H), 7.51 (d, 4H), 7.44 (s, 4H), 7.31 (d, 2H), 7.21 (s, 2H), 7.18 (m, 12H), 7.05 (m, 8H), 6.90 (s, 2H), 1.44 (s, 18H).
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), 1-chloro-3-iodobenzene (6.3 g, 26.4 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A74-1 (white solid, 8.6 g, 78%).
ESI-LCMS: [M]+: C60H56D3ClN2. 845.4546.
Under an argon atmosphere, Intermediate Compound A74-1 (8.6 g, 10 mmol), 4-iodo-1,1′-biphenyl-2,2′,3,3′,4′,5,5′,6,6′-d9 (2.9 g, 10 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A74-2 (white solid, 6.1 g, 61%).
ESI-LCMS: [M]+: C72H56D11ClN2. 1005.5247.
Under an argon atmosphere, Intermediate Compound A74-2 (6 g, 5.9 mmol) was put into a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BBr3 (1.5 equiv.) was added thereto. The reaction solution was stirred 180° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A74-3 (yellow solid, 1.4 g, 23%).
ESI-LCMS: [M]+: C72H53D11BClN2. 1013.5515
Under an argon atmosphere, Intermediate Compound A74-3 (1.4 g, 1.4 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.25 g, 1.4 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A74 (yellow solid, 1.2 g, 71%).
ESI-LCMS: [M]+: C84H53D19BN3. 1152.7071
1H-NMR (CDCl3): d=7.38 (s, 4H), 7.22 (m, 12H), 7.12 (m, 8H), 6.86 (s, 2H), 1.36 (s, 18H), 1.18 (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 9, 13.6 mmol), 1-chloro-3-iodobenzene (6.3 g, 26.4 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A75-1 (white solid, 8.6 g, 78%).
ESI-LCMS: [M]+: C60H56D3ClN2. 845.4546.
Under an argon atmosphere, Intermediate Compound A75-1 (8.6 g, 10 mmol), 3,5-di-tert-butyl-3′-iodo-1,1′-biphenyl (3.9 g, 10 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 put into 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, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A75-2 (white solid, 7.2 g, 61%).
ESI-LCMS: [M]+: C80H83ClN2. 1106.6002.
Under an argon atmosphere, Intermediate Compound A75-2 (7 g, 6.3 mmol) was put into a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BBr3 (1.5 equiv.) was added thereto. The reaction solution was stirred 180° C. for 12 hours. After cooling, triethylamine was added thereto to terminate the reaction, the solvent was removed therefrom under reduced pressure, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound A75-3 (yellow solid, 1.55 g, 22%).
ESI-LCMS: [M]+: C80H80BClN2. 1114.6161
Under an argon atmosphere, Intermediate Compound A75-3 (1.5 g, 1.3 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.23 g, 1.3 mmol), pd2dba3 (0.06 g, 0.12 mmol), tris-tert-butyl phosphine (0.06 mL, 0.24 mmol), and sodium tert-butoxide (0.5 g, 5.1 mmol) were put into a 1 L flask and dissolved in 100 mL of xylene, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound A75 (yellow solid, 1.3 g, 77%).
ESI-LCMS: [M]+: C92H80D8BN3. 1253.7637
1H-NMR (CDCl3): d=8.85 (d, 2H), 7.73 (s, 2H), 7.55 (s, 1H), 7.43 (s, 4H), 7.36 (d, 2H), 7.29 (s, 2H), 7.24 (m, 12H), 7.05 (m, 8H), 6.85 (s, 2H), 1.36 (s, 18H), 1.22 (s, 18H), 1.14 (s, 9H).
Under an argon atmosphere, 3,3′-((4,6-dibromo-1,3-phenylene)bis(oxy))bis(chlorobenzene) (10 g, 20 mmol), phenyl boronic acid (5.2 g, 40 mmol), pd(pph3)4 (2.3 g, 2 mmol), and potassium carbonate (8 g, 60 mmol were put into a 2 L flask and dissolved in 200 mL of toluene and 50 mL of H2O, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound B1-1 (white solid, 7.1 g, 74%).
ESI-LCMS: [M]+: C30H20Cl2O2. 482.0811.
Under an argon atmosphere, Intermediate Compound B1-1 (7 g, 14.5 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (5 g, 29 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.9 g, 60 mmol) were put into a 2 L flask and dissolved in 150 mL of xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound B1-2 (white solid, 9.2 g, 81%).
ESI-LCMS: [M]+: C54H20D16N2O2. 760.3338.
Under an argon atmosphere, Intermediate Compound B1-2 (9 g, 12 mmol) was put into a 1 L flask and dissolved in 200 mL of xylene, and cooled to 0° C. 1.0 M of sec-BuLi solution (1.5 equiv.) was slowly added dropwise thereto, and upon termination, the temperature was raised to 70° C., and stirring was performed for 3 hours. Cooling was performed again to −60° C., BBr3 (3 equiv.) was added thereto, the temperature was raised to room temperature, and stirring was performed for 2 hours. Cooling was performed again to 0° C., N,N-diisopropylethylamine was added thereto, and the temperature was raised to 130° C., and stirring was performed for 4 hours. After termination of the reaction, the filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound B1 (yellow solid, 1.9 g, 21%).
ESI-LCMS: [M]+: C54H17D16BN2O2. 768.3612
1H-NMR (CDCl3): d=8.55 (d, 2H), 7.93 (s, 1H), 7.55 (m, 10H), 7.41 (d, 2H), 7.11 (s, 2H).
Under an argon atmosphere, 4,4′-((4,6-dichloro-1,3-phenylene)bis(oxy))bis(bromobenzene) (10 g, 20 mmol), phenyl boronic acid (5.2 g, 40 mmol), pd(pph3)4 (2.3 g, 2 mmol), and potassium carbonate (8 g, 60 mmol) were put into a 2 L flask and dissolved in 200 mL of toluene and 50 mL of H2O, and the reaction solution was stirred at 100° C. for 12 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound B4-1 (white solid, 7.5 g, 78%).
ESI-LCMS: [M]+: C30H20Cl2O2. 482.1227.
Under an argon atmosphere, Intermediate Compound B4-1 (7.5 g, 15.5 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (5 g, 29 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.9 g, 60 mmol) were put into a 2 L flask and dissolved in 150 mL of xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound B4-2 (white solid, 9.7 g, 82%).
ESI-LCMS: [M]+: C54H20D16N2O2. 760.0828.
Under an argon atmosphere, Intermediate Compound B4-2 (9.7 g, 12.5 mmol) was put into a 1 L flask and dissolved in 200 mL of xylene, and cooled to 0° C. 1.0 M of sec-BuLi solution (1.5 equiv.) was slowly added dropwise thereto, and upon termination, the temperature was raised to 70° C., and stirring was performed for 3 hours. Cooling was performed again to −60° C., BBr3 (3 equiv.) was added thereto, the temperature was raised to room temperature, and stirring was performed for 2 hours. Cooling was performed again to 0° C., N,N-diisopropylethylamine was added thereto, and the temperature was raised to 130° C., and stirring was performed for 4 hours. After termination of the reaction, the filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound B4 (yellow solid, 2.4 g, 23%).
ESI-LCMS: [M]+: C54H17D16BN2O2. 768.1008
1H-NMR (CDCl3): d=8.72 (d, 2H), 7.75 (d, 4H), 7.67 (d, 2H), 7.55 (s, 1H), 7.49 (m, 4H), 7.36 (t, 2H).
Under an argon atmosphere, 3,3′-((4,6-dibromo-1,3-phenylene)bis(oxy))bis(chlorobenzene) (10 g, 20 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (14 g, 80 mmol), pd2dba3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.9 g, 60 mmol) were put into a 2 L flask and dissolved in 150 mL of xylene, and the reaction solution was stirred at 140° C. for 2 hours. After cooling, an extraction process was performed thereon by using water (300 mL) and ethylacetate (300 mL) to collect an organic layer, which was dried by using MgSO4 and filtered. The filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Intermediate Compound B11-1 (white solid, 14.6 g, 77%).
ESI-LCMS: [M]+: C66H10D32N4O2. 954.5343.
Under an argon atmosphere, Intermediate Compound B11-1 (14 g, 14.5 mmol) was put into a 1 L flask and dissolved in 200 mL of xylene, and cooled to 0° C. 1.0 M of sec-BuLi solution (1.5 equiv.) was slowly added dropwise thereto, and upon termination, the temperature was raised to 70° C., and stirring was performed for 3 hours. Cooling was performed again to −60° C., BBr3 (3 equiv.) was added thereto, the temperature was raised to room temperature, and stirring was performed for 2 hours. Cooling was performed again to 0° C., N,N-diisopropylethylamine was added thereto, and the temperature was raised to 130° C., and stirring was performed for 4 hours. After termination of the reaction, the filtrate was decompressed to remove the solvent therefrom, and a solid thus obtained was subjected to silica gel column chromatography using CH2Cl2 and hexane as developing solvents for purification and separation, so as to obtain Compound B111 (yellow solid, 3.5 g, 25%).
ESI-LCMS: [M]+: C66H7D32BN4O2. 962.5212
1H-NMR (CDCl3): d=8.62 (d, 2H), 7.69 (s, 1H), 7.57 (d, 2H), 7.12 (s, 2H).
A HOMO energy level (eV), S1 energy level (eV), T1 energy level (eV), a difference (eV) between the S1 energy level and the T1 energy level, maximum absorption wavelength (λAbs, nm), maximum emission wavelength (λemi/sol and λemi/film, nm), Stokes-shift, and full-width at quarter maximum (FWQM) of each of CD1 to CD4 and CH1 to CH5 as Compounds and Comparative Compounds were evaluated, and results thereof are shown in Table 1.
The HOMO energy level was measured using smart manager software of ZIVE LAB's SP2 electrochemical workstation equipment. λAbs was measured using Labsolutions UV-Vis software while SHIMADZU's UV-1800 UV/Visible Scanning Spectrophotometer equipment was equipped with a deuterium/tungsten-halogen light source and silicon photodiode. S1, T1, λemi, and FWQM were measured using FluorEssence software while HORIBA's fluoromax+ spectrometer equipment was equipped with a xenon light source and a monochromator. λemi/sol is expressed by measuring the maximum emission wavelength of a compound in a toluene solution, and λemi/film is expressed by measuring the maximum emission wavelength of a compound in a film. Stokes-shift shows a difference between the maximum wavelength when absorbing energy and the maximum wavelength when emitting energy.
As a first electrode, a glass substrate (a 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 first electrode to form a hole injection layer having a thickness of 300 Å, H-1-19 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 (Compound B1) and a dopant(Compound A3) were co-deposited on the electron blocking layer in a weight ratio of 98:2 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, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, A1 was deposited on the electron injection layer to form a second electrode having a thickness of 3,000 Å, and HT28 was deposited on the second electrode to form a capping layer having a thickness of 700 Å, thereby completing the manufacture of a light-emitting device. Compounds used to manufacture light-emitting devices are described below.
Light-emitting devices were manufactured in the same manner as in Example 1-1, except that in forming the emission layer, compounds shown in Table 2 were each used as the host and the dopant.
A light-emitting device was manufactured in the same manner as in Example 1-1, except that in forming the emission layer, a host (Compound B1), a sensitizer (PS-1), and a dopant (Compound A3) were co-deposited in a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å.
Light-emitting devices were manufactured in the same manner as in Example 2-1, except that compounds shown in Table 3 were each used as the host and the dopant in forming the emission layer.
A light-emitting device was manufactured in the same manner as in Example 1-1, except that in forming the emission layer, a mixed host including a mixture of a first host (Compound B1) and a second host (HT-1) in a weight ratio of 1:1, a sensitizer (PS-1), and a dopant (Compound A3) were co-deposited in a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å.
Light-emitting devices were manufactured in the same manner as in Example 3-1, except that in forming the emission layer, compounds shown in Table 4 were each used as the host or the dopant.
Tables 2 to 4 show evaluation results of the light-emitting devices for the Examples and the Comparative Examples. In the evaluation results of the characteristics of the light-emitting devices, driving voltage (V) at a current density of 1,000 cd/m2, quantum efficiency (Q.E., %), and emission colors were each measured using Keithley MU 236 and a luminance meter PR650, and the lifespan (T95) is a measure of the time taken when the luminance reaches 95% of the initial luminance. In Table 2, the relative lifespan was calculated based on Comparative Example 1-1. In Table 3, the relative lifespan was calculated based on Comparative Example 2-1. In Table 4, the relative lifespan was calculated based on Comparative Example 3-1. The results thereof are shown below.
Referring to Table 2, it was confirmed that the light-emitting devices of Examples 1-1 to 1-10 had excellent low driving voltage, luminescence efficiency, and lifespan characteristics compared to those of the light-emitting devices of Comparative Examples 1-1 to 1-13.
Referring to Table 3, it was confirmed that the light-emitting devices of Examples 2-1 to 2-10 had excellent low driving voltage, luminescence efficiency, and lifespan characteristics compared to those of the light-emitting devices of Comparative Examples 2-1 to 2-15.
Referring to Table 4, it was confirmed that the light-emitting devices of Examples 3-1 to 3-10 had excellent low driving voltage, luminescence efficiency, and lifespan characteristics compared to those of the light-emitting devices of Comparative Examples 3-1 to 3-16.
A light-emitting device including the heterocyclic compound may have low driving voltage, high efficiency, high color purity, and long lifespan. A high-quality electronic apparatus and a consumer product 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 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.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0093954 | Jul 2023 | KR | national |
