Patent Application
20240247006
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0189638, filed on Dec. 29, 2022, in the Korean Intellectual Property Office, the entire content of which is incorporated by reference herein.
One or more aspects of embodiments of the present disclosure relate to a heterocyclic compound, and an organic light-emitting device and an electronic apparatus including the heterocyclic compound.
Organic light-emitting devices are self-emission devices that, as compared with devices of the related art, have wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and response speed, and produce full-color images.
Organic light-emitting devices may include a first electrode located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked 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. The excitons may transition (relax) from an excited state to a ground state, thus generating light.
One or more aspects of embodiments of the present disclosure are directed toward a novel heterocyclic compound, and an organic light-emitting device and an electronic apparatus including the novel heterocyclic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
One or more embodiments of the present disclosure relate to a heterocyclic compound represented by Formula 1:
One or more embodiments of the present disclosure relate to an organic light-emitting device including a first electrode, a second electrode, an interlayer including an emission layer between the first electrode and the second electrode, and at least one heterocyclic compound.
One or more embodiments of the present disclosure relate to an electronic apparatus including the organic light-emitting device.
According to one or more embodiments, a consumer product includes the organic light-emitting device.
The above and other aspects will be more apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments of the present disclosure, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and duplicative descriptions thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described, by referring to the drawings, to explain aspects of the present disclosure.
As utilized herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, the expressions “at least one of a to c,” “at least one of a, b or c,” and “at least one of a, b and/or c” may indicate only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.
The terminology used herein is for the purpose of describing embodiments and is not intended to limit the embodiments described herein. Unless otherwise defined, all chemical names, technical and scientific terms, and terms defined in common dictionaries should be interpreted as having meanings consistent with the context of the related art, and should not be interpreted in an ideal or overly formal sense. It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element.
As used herein, singular forms such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “includes,” “including,” “comprises,” and/or “comprising,” when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
As used herein, the term “and/or” includes any, and all, combination(s) of one or more of the associated listed items.
The term “may” will be understood to refer to “one or more embodiments of the present disclosure,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments of the present disclosure,” each including a corresponding listed item.
It will be understood that when an element is referred to as being “on,” “connected to,” or “on” another element, it may be directly on, connected, or coupled to the other element or one or more intervening elements may also be present. When an element is referred to as being “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present.
Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper,” “bottom,” “top,” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the drawings. For example, if the device in the drawings is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” or “over” the other elements or features. Thus, the term “below” may encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure pertains. It is also to be understood that terms defined in commonly used dictionaries should be interpreted as having meanings consistent with meanings in the context of the related art, unless expressly defined herein, and should not be interpreted in an ideal or overly formal sense.
In this context, “consisting essentially of” means that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.
Further, in this specification, the phrase “on a plane,” or “plan view,” means viewing a target portion from the top, and the phrase “on a cross-section” means viewing a cross-section formed by vertically cutting a target portion from the side.
A heterocyclic compound according to an embodiment of the present disclosure may be represented by Formula 1:
In an embodiment, R2 in Formula 1 may be a group represented by Formula 1A, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In Formula 1 and 1A, A1 to A5 may each independently be a C5-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, A1 to A5 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, or a dinaphthothiophene group.
In an embodiment, A1 to A5 may each independently be a benzene group or a naphthalene group.
X1 in Formula 1A may be O, S, N(R3), C(R3)(R4), Si(R3)(R4), Ge(R3)(R4), B(R3), P(R4), C(═O), or C(═S).
In an embodiment, X1 may be O, S, N(R3), C(R3)(R4), or Si(R3)(R4).
In an embodiment, X1 may be O, S, or N(R3).
In an embodiment, a group represented by Formula 1A may be a group represented by one of Formulae 1-1 to 1-3.
In Formulae 1-1 to 1-3, X1 and Ar1 are each as described herein, R41 to R43 may each independently be as described for R40, R51 to R54 may each independently be as described for R50, and * indicates a binding site to a neighboring atom.
Ar1 in Formula 1A may be a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, Ar1 may be:
In an embodiment, Ar1 may be selected from a group represented by one of Formulae 5-1 to 5-26 and/or 6-1 to 6-55.
In Formulae 5-1 to 5-26 and 6-1 to 6-55,
In an embodiment, R2 may be the group represented by Formula 1A.
In an embodiment, R2 may be:
In an embodiment, R2 may be selected from the group represented by one of Formulae 5-1 to 5-26 and/or 6-1 to 6-55. In an embodiment, Y31, Y32, Z31 to Z34, and e2 to e9 are defined as in relation to Ar1 as described elsewhere herein.
In an embodiment, R3, R4, R10, R20, R30, R40, and R50 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 unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group unsubstituted or substituted with at least one R10a, a C6-C60 aryl group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryl group unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R10a, —Si(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, at least two of R3, R4, R10, R20, R30, R40, and R50 may optionally be linked together to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, R3, R4, R10, R20, R30, R40, and R50 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, R3, R4, R10, R20, R30, R40, and R50 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, two or more of R3, R4, R10, R20, R30, R40, and R50 may be linked to each other to form a cyclopentane group, a cyclohexane group, a cycloheptane group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with at least one R10a. In an embodiment, two or more of adjacent R3, R4, R10, R20, R30, R40, and R50 may be linked to each other to form a cyclopentane group, a cyclohexane group, a cycloheptane group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with at least one R10a.
In an embodiment, R3, R4, R10, R20, R30, R40, and R50 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, at least one of R3, R4, R10, R20, R30, R40, and R50 may be deuterium, a C1-C20 alkyl group, or a C1-C20 alkyl group substituted with deuterium.
In Formula 1A, b10, b20, b30, b40, and b50 in Formulae 1 and 1A may each independently be 0, 1, 2, 3, 4, 5, 6, 7, or 8.
In an embodiment, b10, b20, b30, b40, and b50 may each independently be 0, 1, 2, 3, or 4.
In Formula 1A, * indicates a binding site to a neighboring atom.
In the specification, R10a may be:
In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 11 or 12:
In an embodiment, the heterocyclic compound represented by Formula 1 may be a compound represented by Formula 21 or 22:
In an embodiment, the heterocyclic compound may include at least one deuterium or a C1-C20 alkyl group.
In an embodiment, the heterocyclic compound may have a symmetric structure.
In an embodiment, the heterocyclic compound may have an asymmetric structure.
In an embodiment, the heterocyclic compound represented by Formula 1 may be selected from Compounds 1 to 432, but embodiments are not limited thereto:
The heterocyclic compound represented by Formula 1 may satisfy a structure in which the group represented by Formula 1A is substituted into a heteroring (i.e., heterocycle), including a boron atom, and, through such a structure, the heterocylic compound may have a narrow full width at half maximum (FWHM), high color purity, and high luminescence efficiency.
Although not limited by theory, the electron-withdrawing characteristics of the heteroring (i.e., heterocycle), of Formula 1 to which a site (-*) of the group represented by Formula 1A is linked, may configure a heterocyclic compound of the present disclosure with multiple resonance effects that may be strengthened by a sequential separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).
In some embodiments, although not limited to theory, the group represented by Formula 1A may include a structure in which Ar1 is substituted into a ring into which the site (-*) to which the heteroring (i.e., heterocycle), of Formula 1 is linked is substituted. Such a structure, may include one or more steric effects that may decrease intermolecular interactions such that the stability of the heterocyclic compound may be enhanced or improved, and the dexter energy transfer may be suppressed or reduced, thereby showing high efficiency characteristics when utilized in to a device (e.g., light-emitting device). The term “dexter energy transfer” as utilized herein refers to an exchange of electrons between two molecules (intermolecular) or between two parts of a molecule (intramolecular).
In some embodiments, accordingly, when the heterocyclic compound represented by Formula 1 is utilized in an organic light-emitting device, the driving voltage is decreased or lowered, and the color purity, luminescence efficiency, and lifespan characteristics may be enhanced or improved. For example, by utilizing the heterocyclic compound represented by Formula 1 in the emission layer, a deep blue organic light-emitting device having low driving voltage, high color purity, high luminescence efficiency, and a long lifespan may be implemented.
In some embodiments, the heterocyclic compound may be configured to emit blue light. For example, the heterocyclic compound may be configured to emit blue light having a maximum emission wavelength of greater than or equal to 400 nanometer (nm) and less than 500 nm, for example, greater than or equal to 410 nm and less than or equal to 490 nm (lower emission CIEx,y color coordinates of 0.15, 0.05 to 0.15), but embodiments are not limited thereto. Thus, the heterocyclic compound represented by Formula 1 may be useful in manufacturing an organic light-emitting device emitting blue light.
In an embodiment, the heterocyclic compound may be configured to emit deep blue light having a maximum emission wavelength of greater than or equal to 410 nm and less than or equal to 465 nm.
Methods of synthesizing the heterocyclic compound represented by Formula 1 may be recognizable by those of ordinary skill in the art by referring to Examples, as described elsewhere herein.
A organic light-emitting device according to an embodiment of the present disclosure may include a first electrode, a second electrode facing the first electrode, and an interlayer. In some embodiments, the interlayer may be located between the first electrode and the second electrode. In some embodiments, the interlayer includes an emission layer. In some embodiments, the organic light-emitting device includes one or more heterocyclic compound according to an embodiment of the present disclosure.
In some embodiments, the first electrode of the organic light-emitting device may be an anode.
In some embodiments, the second electrode of the organic light-emitting device may be a cathode.
In some embodiments, the interlayer may include a hole transport region. In some embodiments, the hole transport region may be located between the first electrode and the emission layer.
In some embodiments, the interlayer may include an electron transport region. In some embodiments, the electron transport region may be located between the emission layer and the second electrode.
In some embodiments, the hole transport region may include one or more of a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.
In some embodiments, the electron transport region may include one or more of a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
In an embodiment, the electron transport region may include a hole blocking layer.
In an embodiment, the hole blocking layer may be in direct contact with the emission layer.
In an embodiment, the hole blocking layer may include a phosphine oxide-containing compound, a silyl-containing compound, or a combination thereof.
In some embodiments, the emission layer may include the heterocyclic compound represented by Formula 1.
In some embodiments, the emission layer of the organic light-emitting device may include a dopant and a host. In some embodiments, the dopant may include the heterocyclic compound represented by Formula 1. In some embodiments, the heterocyclic compound may be configured to be a dopant.
In an embodiment, the emission layer may be configured to emit, for example, blue light. The blue light may have, for example, a maximum emission wavelength in a range of about 400 nm to about 500 nm. In an embodiment, the emission layer may be configured to emit blue light having a maximum emission wavelength of about 390 nm to about 500 nm, about 410 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
In an embodiment, the emission layer may be configured to emit deep blue light. In an embodiment, the emission layer may be configured to emit deep blue light having a maximum emission wavelength of greater than or equal to 410 nm and less than or equal to 465 nm.
In an embodiment, in the emission layer, the amount of the host may be greater than the amount of the dopant based on the weights of the host and the dopant.
In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or a combination thereof. The host is further described elsewhere herein.
In an embodiment, the a light-emitting device (e.g., an organic light-emitting device) that utilizes the heterocyclic compound represented by Formula 1 may have high color purity, high luminescence efficiency, low driving voltage, and long lifespan characteristics.
In an embodiment, the heterocyclic compound represented by Formula 1 may be configured to emit blue light. For example, the heterocyclic compound represented by Formula 1 may be configured to emit blue light having a maximum emission wavelength in a range of about 390 nm to about 500 nm, about 410 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
In some embodiments, the heterocyclic compound represented by Formula 1 may have a color purity for which a CIEx coordinate is about 0.12 to about 0.15 or about 0.13 to about 0.14, and a CIEy coordinate is about 0.06 to about 0.25, about 0.10 to about 0.20, or about 0.13 to about 0.20.
The term “interlayer” as utilized herein refers to a single layer and/or all of a plurality of layers between the first electrode and the second electrode of the organic light-emitting device.
An electronic apparatus according to an embodiment of the present disclosure may include the organic light-emitting device, as disclosed elsewhere herein. The electronic apparatus may further include a thin-film transistor. In some embodiments, the thin-film transistor may include a source electrode and a drain electrode. In some embodiments, the first electrode of the organic 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 a combination thereof. The electronic apparatus is described in more detail elsewhere herein.
A consumer product (an electronic equipment) according to an embodiment of the present disclosure may include the organic light-emitting device.
In some embodiments, the consumer product may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertisement board, an indoor or outdoor lighting and/or signaling light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, a signboard, and/or a sign.
Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in connection with
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work-function material that facilitates injection of holes. The term “high work-function material” as utilized herein refers to a substance (e.g., a metal or metal alloy) that requires a relatively high amount of energy to emit electrons from its surface.
The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or a combination thereof. In some embodiments, when the first electrode 110 is a transflective electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or a combination thereof.
The first electrode 110 may have a single-layered structure including a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be located at (e.g., on or above), the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer, and an electron transport region located between the emission layer and the second electrode 150.
In an embodiment, the interlayer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound such as a heterocyclic compound, an inorganic material such as a quantum dot, and/or the like.
In some embodiments, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between the two or more emitting units. In some embodiments, the organic light-emitting device 10 that has the interlayer 130 including the two or more emitting units and the charge generation layer may be referred to as a tandem organic light-emitting device.
In some embodiments, the hole transport region may include: i) a single-layered structure that includes (e.g., consists of) a single layer including (e.g., consisting of) a single type or kind of material, ii) a single-layered structure that includes (e.g., consists of) a single layer that includes more than one type or kind of materials, or iii) a multi-layered structure including multiple layers that include more than one type or kind of materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.
For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, and/or a hole injection layer/hole transport layer/electron blocking layer structure. In some embodiments, the layers of each structure may be stacked sequentially from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, and/or a combination thereof:
For example, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each be as described for 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 replaced with R10a as described above.
In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In some embodiments, each of Formulae 201 and 202 may include at least one of the groups represented by Formulae CY201 to CY203.
In some embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
In some embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In some embodiments, each of Formulae 201 and 202 may not include(e.g., may exclude) a group represented by one of Formulae CY201 to CY203.
In some embodiments, each of Formulae 201 and 202 may not include(e.g., may exclude) a group represented by one of Formulae CY201 to CY203, and may include at least one of the groups represented by Formulae CY204 to CY217.
In some embodiments, each of Formulae 201 and 202 may not include(e.g., may exclude) a group represented by one of Formulae CY201 to CY217.
In an embodiment, the hole transport region may include at least one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), α-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 a combination thereof:
A thickness of the hole transport region may be in a range of about 50 angstrom (Å) to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. In an embodiment, the electron blocking layer may block or reduce the leakage of electrons from an emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
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 that includes a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
In some embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or a combination thereof.
Non-limiting examples of the quinone derivative are TCNQ, F4-TCNQ, etc.
Non-limiting examples of the cyano group-containing compound are HAT-CN and a compound represented by Formula 221.
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
Non-limiting examples of the metal are 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.); 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.).
Non-limiting examples of the metalloid are silicon (Si), antimony (Sb), and tellurium (Te).
Non-limiting examples of the non-metal are oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
Non-limiting examples of the compound including element EL1 and element EL2 are metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, or metalloid iodide), metal telluride, or a combination thereof.
Non-limiting examples of the metal oxide are tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (for example, MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and rhenium oxide (for example, ReO3, etc.).
Non-limiting examples of the metal halide are alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
Non-limiting examples of the alkali metal halogen may include LiF, NaF, KF, RbF, CsF, LiCI, NaCl, KCl, RbCI, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Non-limiting examples of the alkaline earth metal halide are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
Non-limiting examples of the transition metal halide are titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Non-limiting examples of the post-transition metal halide are zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (for example, Inks, etc.), and tin halide (for example, SnI2, etc.).
Non-limiting examples of the lanthanide metal halide are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
A non-limiting example of the metalloid halide is antimony halide (for example, SbCl5, etc.).
Non-limiting examples of the metal telluride are alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal telluride (for example, ZnTe, etc.), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In some embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer. In some embodiments, the two or more layers contact each other and are configured to emit white light. In some embodiments, the two or more layers are separate from each other and are configured to emit white light. In some embodiments, the emission layer may include two or more materials selected from among a red light-emitting material, a green light-emitting material, and a blue light-emitting material. In some embodiments, the two or more materials are mixed with each other in a single layer to emit white light.
The emission layer may include a host and/or a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or a combination thereof.
The amount of the dopant in the emission layer may be from about 0.01 part by weight to about 15 parts by weight, based on 100 parts by weight of the host.
In some embodiments, the emission layer may include a quantum dot.
In some embodiments, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emission layer. In some embodiments, the host includes the delayed fluorescence material. In some embodiments, the dopant includes the delayed fluorescence material.
The emission layer may further include, in addition to the heterocyclic compound, a host, an auxiliary dopant, a sensitizer, a delayed fluorescent material, or a combination thereof. For example, the emission layer may include the heterocyclic compound, a host, an auxiliary dopant, a sensitizer, a delayed fluorescent material, and/or a combination thereof. Each of the host, the auxiliary dopant, the sensitizer, and/or the delayed fluorescent material may include at least one deuterium.
In some embodiments, the emission layer may include a sensitizer.
In some embodiments, the emission layer may include the heterocyclic compound and the host. The host may be different from the heterocyclic compound, and the host may include an electron transport compound, a hole transport compound, a bipolar compound, and/or a combination thereof. In some embodiments, the host may not include (e.g., may exclude any) metal. In some embodiments, the electron transport compound, the hole transport compound, and the bipolar compound are different from each other.
In an embodiment, the emission layer may include the heterocyclic compound and a host, and the host may include an electron transport compound and a hole transport compound.
In an embodiment, the electron transport compound and the hole transport 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, about 200 Å to about 600 Å. In an embodiment, the emission layer having a thickness within these ranges may be associated with excellent or suitable luminescence characteristics without, or in the absence of, a substantial increase in driving voltage.
In an embodiment, the host may include a compound represented by Formula 301:
In Formula 301,
For example, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In some embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or a combination thereof:
In Formulae 301-1 and 301-2,
In some embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.
In an embodiment, the host may include one or more 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 a 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 transport host.
In an embodiment, the second host compound may be an electron transport host.
In an embodiment, the term “hole transport host” as utilized herein refers to a compound including a hole transport moiety.
In an embodiment, the term “electron transport host” as utilized herein refers to not only a compound including an electron transport moiety, but also a compound having bipolar properties.
The terms “hole transport host” and “electron transport host” may be understood according to the relative difference in hole mobility and electron mobility between the hole transport host and the electron transport host. For example, even when the electron transport host does not include an electron transport moiety, a bipolar compound exhibiting relatively higher electron mobility than the hole transport host may be understood as an electron transport host.
In an embodiment, the hole transport host may be represented by one of Formulae 311-1 to 311-6, and the electron transport host may be represented by one of Formulae 312-1 to 312-4 and 313:
In an embodiment, the first host compound and the second host compound may form an exciplex.
In an embodiment, the first host compound may include one or more of Compounds HTH1 to HTH56 or a combination thereof:
In an embodiment, the second host compound may include one or more of Compounds ETH1 to ETH86 or a combination thereof:
In an embodiment, the emission layer may further include a phosphorescent dopant.
For example, the emission layer may further include a phosphorescent dopant, and the phosphorescent dopant may act as a sensitizer.
In some embodiments, the phosphorescent dopant may include a central metal that includes at least one transition metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a combination thereof.
The phosphorescent dopant may be electrically neutral.
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:
For example, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In an embodiment, when xc1 in Formula 401 is 2 or more, two ring A401(s) among two or more of L401 may optionally be bonded to each other via T402, which is a linking group, and two ring A402(s) among two or more of L401 may optionally be bonded to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be as described for T401.
L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN, a phosphorus-containing group (for example, a phosphine group, a phosphite group, etc.), or a combination thereof.
The phosphorescent dopant may be, for example, one or more of Compounds PD1 to PD41 or a 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 a combination thereof.
For example, the fluorescent dopant may include a compound represented by Formula 501:
For example, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
In some embodiments, xd4 in Formula 501 may be 2.
For example, the fluorescent dopant may include: one or more of Compounds FD1 to FD36; DPVBi; DPAVBi; or a combination thereof:
In an embodiment, the emission layer may further include a delayed fluorescent material.
In the present specification, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.
The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the type or kind of other materials included in the emission layer.
In some embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescent materials may effectively or suitably occur, and thus, the luminescence efficiency of the organic light-emitting device 10 may be enhanced or improved.
For example, the delayed fluorescent material may include i) 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, or a π electron-deficient nitrogen-containing C1-C60 cyclic group), and ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed and simultaneously include boron (B).
Examples of the delayed fluorescent material may include at least one of the following compounds DF1 to DF9:
The emission layer may include a quantum dot.
The term “quantum dot” as utilized herein refers to one or more crystal(s) of a semiconductor compound. In an embodiment, the quantum dot may include any material configured to or capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal(s).
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 then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected. In an embodiment, the wet chemical process may be less expensive and/or is easier to perform compared to vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, a Group IV element, a Group IV compound, or a combination thereof.
Non-limiting examples of the Group II-VI semiconductor compound are 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; and a combination thereof.
Non-limiting examples of the 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; and a combination thereof. In some embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element are InZnP, InGaZnP, InAlZnP, etc.
Non-limiting examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3, or InGaSe3; and a combination thereof.
Non-limiting examples of the Group I-III-VI semiconductor compound are: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or a combination thereof.
Non-limiting examples of the Group IV-VI semiconductor compound are: 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; and a combination thereof.
The 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 a combination thereof.
Each element included in a multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present at a substantially uniform concentration or -substantially non-uniform concentration in a particle.
In some embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform. In some embodiments, the quantum dot may have a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
Non-limiting examples of the shell of the quantum dot may be an oxide of metal, metalloid, or non-metal, a semiconductor compound, and a combination thereof. Non-limiting examples of the oxide of metal, metalloid, or non-metal are 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; and a combination thereof. Non-limiting examples of the semiconductor compound are, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; and a combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or a combination thereof.
A full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45 nanometer (nm) or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be enhanced or improved.
In some embodiments, the quantum dot may be in the form of a spherical nanoparticle, a pyramidal nanoparticle, a multi-arm nanoparticle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from the emission layer that includes the quantum dot. Accordingly, by utilizing quantum dots of different sizes, an organic light-emitting device that emits light of one or more suitable wavelengths may be implemented. In some embodiments, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by a combination of light of one or more suitable colors.
In some embodiments, the electron transport region may include: i) a single-layered structure that includes (e.g., consists of) a single layer including (e.g., consisting of) a single type or kind of material, ii) a single-layered structure that includes (e.g., consists of) a single layer that includes more than one type or kind of materials, or iii) a multi-layered structure including multiple layers that include more than one type or kind of materials.
In some embodiments, 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, and/or a combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, and/or a buffer layer/electron transport layer/electron injection layer structure. In some embodiments, the layers of each structure may be sequentially stacked starting from the emission layer.
In an embodiment, the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound. In some embodiments, the metal-free compound includes at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
For example, the electron transport region may include a compound represented by Formula 601:
For example, when xe11 in Formula 601 is 2 or 3, two or more of Ar601(s) may be linked to each other via a single bond.
In other embodiments, Ar601 in Formula 601 may be an anthracene group unsubstituted or substituted with at least one R10a.
In other embodiments, the electron transport region may include a compound represented by Formula 601-1:
For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In some embodiments, the electron transport region may include one or more 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 a 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, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or a combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region within these ranges may be associated with an organic light-emitting device that has suitable or satisfactory electron transport characteristics without, or in the absence of, a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The metal ion of an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion. The metal ion of an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or a combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region may include an electron injection layer. In an embodiment, the electron injection layer facilitates the injection of electrons from the second electrode 150. In an embodiment, the electron injection layer may directly contact the second electrode 150. In an embodiment, the electron injection layer may directly contact the second electrode 150.
In some embodiments, the electron injection layer may include: i) a single-layered structure that includes (e.g., consists of) a single layer including (e.g., consisting of) a single type or kind of material, ii) a single-layered structure that includes (e.g., consists of) a single layer that includes more than one type or kind of materials, or iii) a multi-layered structure including multiple layers that include more than one type or kind of materials.
In some embodiments, 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 a combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or a combination thereof.
The alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or a combination thereof. The alkaline earth metal oxide-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (wherein x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or a combination thereof. In some embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and/or the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and/or the rare earth metal and ii), a ligand bonded to the metal ion. For example, the ligand may be a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or a combination thereof.
In some embodiments, the electron injection layer may include (e.g., consist of): i) an alkali metal-containing compound (for example, an alkali metal halide); or ii) a) an alkali metal-containing compound (for example, an alkali metal halide), and b) an alkali metal, an alkaline earth metal, a rare earth metal, or a combination thereof. For example, the electron injection layer may include (e.g., be) a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
In some embodiments, the electron injection layer may include an organic material (for example, a compound represented by Formula 601), in addition to an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof, as described herein. In some embodiments, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or a combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. In an embodiment, the thickness of the electron injection layer within the ranges described may be associated with an organic light-emitting device that has suitable or satisfactory electron injection characteristics without, or in the absence of, a substantial increase in driving voltage.
Returning to
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 a combination thereof. The second electrode 150 may be a transmissive electrode, a transflective electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be external to, or located outside (e.g., on) the first electrode 110, and/or a second capping layer may be external to, or located outside the second electrode 150. In more detail, the organic light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order. In an embodiment, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order. In an embodiment, the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.
Light generated in the emission layer of the interlayer 130 may be directed away from the light-emitting device 10 through the first electrode 110, (which is a transflective electrode or a transmissive electrode), and the first capping layer. Light generated in the emission layer of the interlayer 130 may be directed away from the organic light-emitting device 10 through the second electrode 150, (which is a transflective electrode or a transmissive electrode), and the second capping layer.
The first capping layer and the second capping layer may be configured to enhance or increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the organic light-emitting device 10 is enhanced or increased, so that the luminescence efficiency of the organic light-emitting device 10 may be enhanced or improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer or the second capping layer may (e.g., each of the first cappling layer and the second capping layer may each) independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or a combination thereof. In an embodiment, the carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be substituted with O, N, S, Se, Si, F, Cl, Br, I, or a combination thereof. In some embodiments, at least one of the first capping layer or the second capping layer may (e.g., each of the first cappling layer and the second capping layer may each) independently include an amine group-containing compound.
For example, at least one of the first capping layer or the second capping layer may independently include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof.
In some embodiments, at least one of the first capping layer or the second capping layer may (e.g., each of the first cappling layer and the second capping layer may each) independently include one or more of Compounds HT28 to HT33, one or more of Compounds CP1 to CP6, β-NPB, or a combination thereof:
The organic light-emitting device disclosed herein may be utilized at a driving voltage of about 4.5 V to about 4.7 V; or about 4.2 V to about 4.4 V.
The organic light-emitting device disclosed herein may be characterized by a luminescence efficiency of about 20 to about 140; or about 22 to about 130; or about 24 to about 28, where luminescence efficiency is reported as candela per ampere (cd/A).
The organic light-emitting device disclosed herein may be characterized by a lifespan (T95) of about 300 hours (h) to about 500 h; or about 330 h to about 480 h; or about 330 h to about 420 h.
The heterocyclic compound represented by Formula 1 may be included in one or more suitable films. Accordingly, according to some embodiments, a film including the heterocyclic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or a light control component) (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, and/or like). In an embodiment, the film may be a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like). In an embodiment, the film may be a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
Some embodiments of the present disclosure relate to one or more electronic apparatus that includes the organic light-emitting device as disclosed herein. In an embodiment, the electronic apparatus including the organic light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the organic light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located along or arranged in at least one traveling direction of light emitted from the organic light-emitting device. For example, the light emitted from the organic light-emitting device may be blue light or white light. The organic light-emitting device may be the same as described above. In some embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas. In an embodiment, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas. In an embodiment, the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel defining layer may be located among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas. In an embodiment, the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light. In an embodiment, the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In an embodiment, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include(e.g., may exclude) a quantum dot. More details on the quantum dot are disclosed elsewhere herein. In an embodiment, the first area, the second area, and/or the third area may each include a scatterer.
For example, the organic light-emitting device may be configured to emit a first light, the first area may be configured to absorb the first light and to emit a first-first color light, the second area may be configured to absorb the first light and to a emit second-first color light, and the third area may be configured to absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In 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 organic light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
The electronic apparatus may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the organic light-emitting device. The sealing portion allows light to be directed away from the organic light-emitting device, while concurrently (e.g., simultaneously) preventing or reducing ambient air and moisture from penetrating into the organic light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
One or more suitable functional layer(s) may be located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the required and/or desired function of the electronic apparatus. The functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
The authentication apparatus may further include, in addition to the organic light-emitting device, a biometric information collector. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.).
The electronic apparatus may be utilized with or applied to one or more suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The organic light-emitting apparatus 20 includes a substrate 100, a thin-film transistor (TFT), an organic light-emitting device, and an encapsulation portion 300 that seals the organic light-emitting device.
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located at (e.g., on) the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
The TFT may be located at (e.g., on) the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor. The activation layer 220 may include a source region, a drain region, and a channel region.
A gate insulating film 230 may be located at (e.g., on) the activation layer 220. The gate insulating film 230 may be configured to insulate the activation layer 220 from the gate electrode 240. The gate electrode 240 may be located at (e.g., on) the gate insulating film 230.
An interlayer insulating film 250 may be located at (e.g., on) the gate electrode 240. The interlayer insulating film 250 may be configured to insulate components of the light-emitting apparatus 20 from one another. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 and/or between the gate electrode 240 and the drain electrode 270, e.g., to insulate them from one another.
The source electrode 260 and the drain electrode 270 may be located at (e.g., on) the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and/or the drain region of the activation layer 220. The source electrode 260 and/or the drain electrode 270 may be located at (e.g., in contact with) the exposed portions of the source region and/or the drain region of the activation layer 220.
The TFT may be electrically connected to the organic light-emitting device to to provide electrical power to, or drive, the organic 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 a combination thereof. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The organic light-emitting device may include the first electrode 110, the interlayer 130, and the second electrode 150.
The first electrode 110 may be located at (e.g., on) the passivation layer 280. The passivation layer 280 may be configured or located to expose a portion of the drain electrode 270. In an embodiment, the passivation layer 280 may cover a portion, (i.e., not the entire structure), of the drain electrode 270. The first electrode 110 may be configured or located to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be located at (e.g., on) the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and an interlayer 130 may be formed in an exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. In an embodiment, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be configured or located as (or in the form of) a common layer.
The second electrode 150 may be located at (e.g., on) the interlayer 130, and a capping layer 170 may be located at (e.g., on) the second electrode 150. The capping layer 170 may be configured, or formed, to cover the second electrode 150.
The encapsulation portion 300 may be located at (e.g., on) the capping layer 170. The encapsulation portion 300 may be located or arranged at (e.g., on) the organic light-emitting device to protect the organic 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 (ITO), indium zinc oxide (IZO), or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or a combination thereof; or a combination of the inorganic films and the organic films.
The light-emitting apparatus 30 include all components as described for the light-emitting apparatus 20 of
The electronic equipment 1 may include a display area DA and a non-display area NDA that is external to, or outside of, the display area DA. A display device may implement an image through an array of a plurality of pixels that are two-dimensionally located or arranged at (e.g., on or in) the display area DA.
The non-display area NDA does not display an image, and may entirely surround the display area DA. On the non-display area NDA, a driver for providing electrical signals and/or power to display devices located or arranged at (e.g, on) the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board may be electrically connected, may be located or arranged.
In the electronic equipment 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. For example, as shown in
Referring to
The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts except for the body. The exterior of the vehicle body may include a front panel, a bonnet or hood, a roof panel, a rear panel, a trunk, a filler provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheels, left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a filler arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in the +x direction or the −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the +x direction or the −x direction. In other words, an imaginary straight line L connecting the side window glasses 1100 may extend in the +x direction or the −x direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the +x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one embodiment, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, a hodometer, an automatic shift selector indicator lamp, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a heater of a seat are disposed. The center fascia 1500 may be arranged on one side of the cluster 1400.
A passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In an embodiment, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be disposed to correspond to a passenger seat. In 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 vehicle 1000 may include the display device 2 that may include a display panel 3 configured to display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be located or arranged at (e.g, on) at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic EL display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to an embodiment of the disclosure, an organic light-emitting display device including the organic light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described above may be utilized in embodiments of the disclosure.
Referring to
Referring to
Referring to
The respective layers included in the hole transport region, the emission layer, and/or the electron transport region may be formed by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and/or laser-induced thermal imaging.
The respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed by vacuum deposition. In an embodiment, 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 utilized herein refers to a cyclic group consisting of carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The term “cyclic group” as utilized herein may include the C3-C60 carbocyclic group, and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as utilized herein refers to a cyclic group that has three to sixty carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N═*′ as a ring-forming moiety.
For example,
The terms “the cyclic group, the C3-C60 carbocyclic group, the C1-C60 heterocyclic group, the π electron-rich C3-C60 cyclic group, or the π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is utilized. In an embodiment, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understand by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Depending on context, a divalent group may refer or be a polyvalent group (e.g., trivalent, tetravalent, etc., and not just divalent) per, e.g., the structure of a formula in connection with which of the terms are utilized.
In some embodiments, examples of the monovalent C3-C60 carbocyclic group and the 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, and examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and specific examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a see-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a see-pentyl group, a 3-pentyl group, a see-isopentyl group, an n-hexyl group, an isohexyl group, a see-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a see-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a see-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a see-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a see-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, a propynyl group, and/or the like. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as utilized herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and specific examples are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term C3-C10 cycloalkenyl group utilized herein refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and specific examples thereof are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as utilized herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C6-C60 aryl group are a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C6-C60 aryloxy group” as utilized herein indicates —OA102 (wherein A102 is a C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein indicates —SA103 (wherein A103 is a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” utilized herein refers to —A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term C2-C60 heteroarylalkyl group” utilized herein refers to —A106A107 (where A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
The term “R10a” as utilized herein refers to:
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and a combinations thereof.
The term “Ph” as utilized herein refers to a phenyl group, the term “Me” as utilized herein refers to a methyl group, the term “Et” as utilized herein refers to an ethyl group, the term “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and the term “OMe” as utilized herein refers to a methoxy group.
The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group.” In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
The term “substituted” as utilized herein, refers to that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 fluoroalkyl group, a cyano group, or a combination thereof.
In one example of the present disclosure, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a halogen, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C10 fluoroalkyl group, or a cyano group. In some embodiments, in specific examples of the present disclosure, “substituted” refers to replacement of at least on hydrogen of a substituent or a compound by deuterium, a halogen, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C1 to C10 fluoroalkyl group, or a cyano group. In some embodiments, in specific examples of the present disclosure, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a halogen, a C1 to C5 alkyl group, a C6 to C18 aryl group, a C1 to C5 fluoroalkyl group, or a cyano group. In some embodiments, in specific examples of the present disclosure, “substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a cyano group, a halogen, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, a trifluoromethyl group, or a naphthyl group.
In the present specification, the x-axis, y-axis, and z-axis are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.
In the present disclosure, when particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “diameter” indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
Terms such as “substantially,” “about,” and “approximately” are used as relative terms and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. They may be inclusive of the stated value and an acceptable range of deviation as determined by one of ordinary skill in the art, considering the limitations and error associated with measurement of that quantity. For example, “about” may refer to one or more standard deviations, or ±30%, 20%, 10%, 5% of the stated value.
Numerical ranges disclosed herein include and are intended to disclose all subsumed sub-ranges of the same numerical precision. For example, a range of “1.0 to 10.0” includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicant therefore reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The light emitting device, electronic apparatus, electronic equipment and other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the light emitting device, electronic apparatus, and electronic equipment may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
Hereinafter, compounds according to embodiments and an organic light-emitting device according to embodiments will be described in more detail with reference to the following Synthesis Examples and Examples. The wording “B was utilized instead of A” as appears when describing Synthesis Examples indicates that an identical molar equivalent of B was utilized in place of A.
1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-([1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)-[1,1′:3,1″-terphenyl]-2′-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 62-1. (yield: 52%)
Intermediate 62-1 (1 eq), 3-(4-(tert-butyl)phenyl)-N-(3-chlorophenyl)-9-phenyl-9H-carbazol-4-amine (1.2 eq), 1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-([1 ,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)-[1 , 1:3,1″-terphenyl]-2′-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was filtered by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 62-2. (yield: 61%)
After Intermediate 62-2 (1 eq) was dissolved in a flask containing ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr3 (5 eq) dissolved in ortho-dichlorobenzene was slowly injected thereto. After completion of adding dropwise, the temperature was raised to 190° C., followed by stirring for 24 hours. After cooling at 0° C., triethylamine was added to terminate the reaction, dropwise to the flask, until the exotherm stopped, and then, n-hexane and methanol were added thereto to cause precipitation and a solid was obtained therefrom by filtration. The solid thus obtained was purified by silica filtration, and then purified again by recrystallization utilizing dichloromethane (MC)/hexane to obtain Intermediate 62-3. Afterwards, final purification was performed thereon by utilizing column chromatography (dichloromethane: n-hexane). (yield: 90%)
Intermediate 62-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (PtBu3, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 24 hours 1 at 150° C. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain Compound 62 (yield: 57%). Then, the final purity was subjected to a final purification through sublimation and purification, and the obtained compound was identified as Compound 62 by ESI-LCMS.
ESI-LCMS: [M]+: C94H78N4, 1285.0
3,5-dibromo-3′,5′-di-tert-butyl-1 ,1′-biphenyl (1 eq), N-(3′,5′-di-tert-butyl-[1 ,1′-biphenyl]-3-yl)-3-phenyldibenzo[b,d]furan-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 95-1. (yield: 61%)
Intermediate 95-1 (1 eq), 5′-(tert-butyl)-N-(3-chlorophenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 95-2. (yield: 60%).
After Intermediate 95-2 (1 eq) was dissolved in a flask containing ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr3 (5 eq) dissolved in ortho-dichlorobenzene was slowly injected thereto. After completion of adding dropwise, the temperature was raised to 190° C., followed by stirring for 24 hours. After cooling at 0° C., triethylamine was added to terminate the reaction, dropwise to the flask, until the exotherm stopped, and then, n-hexane and methanol were added thereto to cause precipitation and a solid was obtained therefrom by filtration. The solid thus obtained was purified by silica filtration, and then purified again by recrystallization utilizing MC/hexane to obtain Intermediate 95-3. Afterwards, final purification was performed thereon by utilizing column chromatography (dichloromethane: n-hexane). (yield: 8%)
Intermediate 95-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (PtBu3,0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 24 hours at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain Compound 95 (yield: 57%). Then, a final purification was proceeded through sublimation and purification, and the obtained compound was identified as Compound 95 by ESI-LCMS.
ESI-LCMS: [M]+: C98H82N3, 1345.1
1,3-dibromo-5-chlorobenzene (1 eq), N-(3′-(tert-butyl)-[1,1′-biphenyl]-3-yl)-2-(4-(tert-butyl) phenyl)dibenzo[b,d]furan-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 244-1. (yield: 63%)
Intermediate 244-1 (1 eq), N-(3-chlorophenyl)-3-phenyldibenzo[b,d]furan-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 244-2. (yield: 66%)
After Intermediate 244-2 (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr3 (5 eq) dissolved in ortho-dichlorobenzene was slowly injected thereto. After completion of adding dropwise, the temperature was raised to 190° C., followed by stirring for 24 hours. After cooling at 0° C., triethylamine was added to terminate the reaction, dropwise to the flask, until the exotherm stopped, and then, n-hexane and methanol were added thereto to cause precipitation and a solid was obtained therefrom by filtration. The solid thus obtained was purified by silica filtration, and then purified again by recrystallization utilizing MC/hexane to obtain Intermediate 244-3. Afterwards, final purification was performed thereon by utilizing column chromatography (dichloromethane: n-hexane). (yield: 7%)
Intermediate 244-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (PtBu3, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 24 hours at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain Compound 244 (yield: 59%). Then, a final purification was proceeded through sublimation and purification, and the obtained compound was identified as Compound 244 by ESI-LCMS.
ESI-LCMS: [M]+: C92H51N4, 1287.9
1,3-dibromo-5-chlorobenzene (1 eq), N-(3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-yl)-3-phenyldibenzo[b,d]thiophen-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The resulting product was purified by column chromatography (dichloromethane: n-hexane), and then recrystallized to obtain Intermediate 310-1. (yield: 54%)
Intermediate 310-1 (1 eq), 2-(3-(tert-butyl)phenyl)-N-(3′,5′-di-tert-butyl-[1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The resulting product was purified by column chromatography (dichloromethane: n-hexane), and then recrystallized to obtain Intermediate 310-2. (yield: 61%)
After Intermediate 310-2 (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr3 (5 eq) dissolved in ortho-dichlorobenzene was slowly injected thereto. After completion of adding dropwise, the temperature was raised to 190° C., followed by stirring for 24 hours. After cooling at 0° C., triethylamine was added to terminate the reaction, dropwise to the flask, until the exotherm stopped, and then, n-hexane and methanol were added thereto to cause precipitation and a solid was obtained therefrom by filtration. The solid thus obtained was purified by silica filtration, and then purified again by recrystallization utilizing MC/hexane to obtain Intermediate 310-3. Afterwards, final purification was performed thereon by utilizing column chromatography (dichloromethane: n-hexane). (yield: 8%)
Intermediate 310-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (PtBu3, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 24 hours at 150° C. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain Compound 310 (yield: 56%). Then, a final purification was proceeded through sublimation and purification, and the obtained compound was identified as Compound 310 by ESI-LCMS.
ESI-LCMS: [M]+: C106H104N3, 1479.3
1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-([1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)-3-(2-(tert-butyl)phenyl)dibenzo[b,d]furan-1-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 422-1. (yield: 57%)
Intermediate 422-1 (1 eq), N-(3-chlorophenyl)-3,9-diphenyl-9H-carbazol-4-amine (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 20 hours in a high pressure reactor at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was filtered by column chromatography and recrystalized (dichloromethane: n-hexane) to obtain Intermediate 422-2. (yield: 64%)
After Intermediate 422-2 (1 eq) was dissolved in ortho-dichlorobenzene, the flak was cooled to 0° C. in a nitrogen atmosphere, and then BBr3 (5 eq) dissolved in ortho-dichlorobenzene was slowly injected thereto. After completion of adding dropwise, the temperature was raised to 190° C., followed by stirring for 24 hours. After cooling at 0° C., triethylamine was added to terminate the reaction, dropwise to the flask, until the exotherm stopped, and then, n-hexane and methanol were added thereto to cause precipitation and a solid was obtained therefrom by filtration. The solid thus obtained was purified by silica filtration, and then purified again by recrystallization utilizing methylene chloride (MC)/hexane to obtain Intermediate 422-3. Afterwards, final purification was performed thereon by utilizing column chromatography (dichloromethane: n-hexane). (yield: 7%)
Intermediate 422-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (PtBu3, 0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred for 24 hours at 150° C. in a nitrogen atmosphere. The mixture was cooled and then dried under reduced pressure to remove o-xylene. Afterwards, a washing process was performed thereon three times by using utilizing ethyl acetate and water, (e.g., the residue was dissolved in ethyl acetate and washed with water three times) and an organic layer thus obtained was dried by utilizing MgSO4 under reduced pressure. The reaction product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain Compound 422 (yield: 52%). Then, a final purification was proceeded through sublimation and purification, and the obtained compound was identified as Compound 422 by ESI-LCMS.
ESI-LCMS: [M]+: C86H52N4, 1194.8
To prepare the organic light-emitting device of Example 1 (IE-1), a glass substrate (available from Corning Co., Ltd), on which an ITO anode (15 Ohms per square centimeter (Q/cm2)) having a thickness of 1,200 angstrom (A) was formed, was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, cleaned with ultraviolet rays for 30 minutes and then cleaned with ozone, and was mounted on a vacuum deposition apparatus.
NPD was deposited on the anode to form a hole injection layer having a thickness of 300 Å, HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å, and then, CzSi was deposited on the hole transport layer to form an emission auxiliary layer having a thickness of 100 Å.
A mixed host of Compounds HTH54 and ETH66 (weight ratio 5:5), Compound PD40 (phosphorescent sensitizer), and Compound 62 (dopant) were co-deposited on the emission auxiliary layer at a weight ratio of 85:14:1 to form an emission layer having a thickness of 200 Å.
Subsequently, 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, and then, Al was deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices of Examples 2 to 10 (IE-2 to IE-10) and Comparative Examples 1 to 6 (CE-1 to CE-6) were manufactured in substantially the same manner as in Example 1, except that compounds shown in Tables 1 and 2 were each utilized as the host, the sensitizer, and the dopant in forming the emission layer. Compounds A, B and C were included as a dopant in the dopant for Comparative Examples 1 to 6 (CE-1 to CE-6).
Each of the driving voltage at 1,000 (cd/m2), luminescence efficiency in candela per ampere (cd/A), emission color, and lifespan (T95) of the organic light-emitting devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 6 were measured utilizing Keithley MU 236 and luminance meter PR650, and results thereof are shown in Tables 1 and 2. In Tables 1 and 2, the lifespan (T95) indicates a time (hr) for the luminance to reach 95% of its initial luminance.
For Examples 1 to S (IE-1 to IE-5) and Comparative Examples 1 to 3 (CE-1 to CE-3), the dopants utilized in the host were HTH54 and ETH66 and the dopant utilized in the sensitizer was PD 40.
For Examples 6 to 10 (IE-6 to IE-10) and Comparative Examples 4 to 6 (CE-4 to CE-6), the dopants utilized in the host were HTH55 and ETH85 and the dopant utilized in the sensitizer was PD 41.
For Examples 1 to 10 (IE-1 to IE-10) and Comparative Examples 1 to 6 (CE-1 to CE-6) the emission color was blue.
Referring to Tables 1 and 2, it was confirmed that, compared to the organic light-emitting devices of Comparative Examples 1 to 6, the organic light-emitting devices of Examples 1 to 10 (each) had low driving voltage, high luminescence efficiency, and significantly excellent or suitable lifespan.
According to the one or more embodiments, an organic light-emitting device including the heterocyclic compound may have low driving voltage, high efficiency, high color purity, and long lifespan. In some embodiments, a high-quality electronic apparatus and a consumer product may be manufactured by utilizing the organic light-emitting device.
It should be understood that the practical example embodiments of the present disclosure should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0189638 | Dec 2022 | KR | national |
