Patent Application
20240155868
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0125778, filed on Sep. 30, 2022, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
One or more embodiments of the present disclosure relate to a condensed cyclic compound, a light-receiving device including the condensed cyclic compound, and an electronic apparatus and an electronic device that include the light-receiving device.
Organic light-receiving devices, which are devices including organic compounds capable of being excited by light, are widely utilized in digital cameras, broadcasting cameras, surveillance cameras, computer image cameras, camcorders, automotive sensors, household sensors, solar cells, and/or the like.
A light-receiving device may have a structure in which a first electrode is arranged on a substrate, and an interlayer and a second electrode are sequentially formed on the first electrode. The interlayer may include an electron-donating layer including an electron donor and an electron-accepting layer including an electron acceptor. A p-type or kind semiconductor material may be utilized as the electron donor, and an n-type or kind semiconductor material may be utilized as the electron acceptor.
When light is irradiated to the organic light-receiving device, electrons may be excited and holes may be generated due to absorption of the light, and the excited electrons and the newly generated holes may be paired to form excitons. The excitons move to an interface of the interlayer and are separated into electrons and holes again according to characteristics of the interface. The separated electrons and holes move to each corresponding electrode, thereby generating current.
One or more aspects of embodiments of the present disclosure are directed toward a condensed cyclic compound, a light-receiving device having characteristics of high sensitivity, high efficiency, and long lifespan by including the condensed cyclic compound, and an electronic apparatus and an electronic device including the light-receiving device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments of the present disclosure, a condensed cyclic compound may include at least one first repeating unit and at least one second repeating unit, wherein the first repeating unit may include at least one selected from a first-first moiety represented by Formula 1-1 and a first-second moiety represented by Formula 1-2, the second repeating unit may include at least one selected from a second-first moiety represented by Formula 2-1 and a second-second moiety represented by Formula 2-2, and at least one of the first repeating unit may further include at least one π electron-rich C1-C60 group.
In Formulae 1-1 and 1-2,
In Formulae 2-1 and 2-2,
According to one or more embodiments of the present disclosure, a light-receiving device may include the condensed cyclic compound of the present disclosure.
According to one or more embodiments of the present disclosure, an electronic apparatus includes the light-receiving device.
According to one or more embodiments of the present disclosure, an electronic device includes the light-receiving device.
The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the present disclosure, and duplicative descriptions thereof may not be provided for conciseness. In this regard, the embodiments of the present disclosure may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments of the present disclosure are merely described, by referring to the drawings, to explain aspects of the present disclosure. As utilized herein, the term “and/or” or “or” may include any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b, or c” indicates 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.
As the present disclosure allows for one or more suitable changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in more detail in the written description. Effects and features of the present disclosure, and methods of achieving the same will be clarified by referring to embodiments described in more detail with reference to the drawings. The present disclosure may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein.
Hereinafter, embodiments of the disclosure will be described in more detail with reference to the accompanying drawings. The same or corresponding components will be denoted by the same reference numerals, and thus redundant description thereof will not be provided for conciseness.
It will be understood that although the terms “first,” “second,” and/or the like may be utilized herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only utilized to distinguish one component from another.
An expression utilized in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.
It will be further understood that the terms “comprise(s)”, “include(s)”, “have/has”, and/or the like as utilized herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
Sizes of elements in the drawings may be exaggerated for convenience of explanation. In other words, because sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.
When a certain embodiment is implemented differently, a specific process order may be performed differently from the described order. For example, two processes described in succession may be performed substantially concurrently (e.g., simultaneously), or may be performed in an order opposite to the described order.
It will be understood that when a layer, region, or component is referred to as being “connected to” another layer, region, or component, the layer, region, or component may be directly connected to the another layer, region, or component, or indirectly connected to the another layer, region, or component as an intervening layer, region, or component may be present. For example, it will be understood that when a layer, region, or component is referred to as being “electrically connected to” another layer, region, or component, the layer, region, or component may be directly electrically connected to the another layer, region, or component, or indirectly electrically connected to the another layer, region, or component as an intervening layer, region, or component may be present.
A condensed cyclic compound according to one or more embodiments may include at least one first repeating unit and at least one second repeating unit, wherein the first repeating unit may include at least one selected from among a first-first moiety represented by Formula 1-1 and a first-second moiety represented by Formula 1-2, the second repeating unit may include at least one selected from among a second-first moiety represented by Formula 2-1 and a second-second moiety represented by Formula 2-2, and at least one of the first repeating unit may further include at least one π electron-rich C1-C60 group:
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may satisfy Condition 1A, and may be represented by Formula 1-A:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 1B, and may be represented by Formula 1-B:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 1C, and may be represented by Formula 1-C:
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may satisfy Condition 2A, and may be represented by Formula 2-A:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 2B, and may be represented by Formula 2-B:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 2C, and may be represented by Formula 2-C:
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may satisfy Condition 3A, and may be represented by Formula 3-A:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 3B, and may be represented by Formula 3-B:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 3C, and may be represented by Formula 3-C:
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may satisfy Condition 4A, and may be represented by Formula 4-A:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 4B, and may be represented by Formula 4-B:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 4C, and may be represented by Formula 4-C:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 4D, and may be represented by Formula 4-D:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 4E, and may be represented by Formula 4-E:
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may satisfy Condition 5A, and may be represented by Formula 5-A:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 5B, and may be represented by Formula 5-B:
The condensed cyclic compound according to an embodiment may satisfy Condition 5C, and may be represented by Formula 5-C:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 5D, and may be represented by Formula 5-D:
The condensed cyclic compound according to one or more embodiments may satisfy Condition 5E, and may be represented by Formula 5-E-1 or 5-E-2:
In the condensed cyclic compound according to one or more embodiments, X1 and X2 may each independently be S or Se.
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments, a moiety represented by
in Formula 2-1 or 2-2 may include a group represented by one selected from among Formulae 4-1-1 to 4-1-4:
In the condensed cyclic compound according to one or more embodiments,
in Formula 2-2 may include a group represented by one selected from among Formulae 4-2-1 to 4-2-4:
The condensed cyclic compound according to one or more embodiments may satisfy one selected from among Conditions i) to iv):
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments,
In the condensed cyclic compound according to one or more embodiments, the π electron-rich C1-C60 group may not be a halogen.
The condensed cyclic compound according to one or more embodiments may further include at least one linker moiety,
In the condensed cyclic compound according to one or more embodiments,
The condensed cyclic compound according to one or more embodiments may include
The electron-accepting moiety may include a 9-methylenefluorene moiety and at least one cyano group linked to the 9-methylenefluorene moiety,
A lowest unoccupied molecular orbital (LUMO) energy level of the condensed cyclic compound according to one or more embodiments may be less than −2.5 eV, and a highest occupied molecular orbital (HOMO) energy level thereof may be less than −4.5 eV.
The condensed cyclic compound according to one or more embodiments may be to absorb green light or red light.
The condensed cyclic compound according to one or more embodiments may be one selected from among Compounds 1 to 48 and R01 to R07:
In one or more embodiments, a light-receiving device may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including a light-receiving layer; and
In the light-receiving device according to one or more embodiments,
In the light-receiving device according to one or more embodiments, the light-receiving layer may include the condensed cyclic compound of the present disclosure.
In the light-receiving device according to one or more embodiments, the light-receiving layer may be to absorb green light or red light.
The light-receiving device according to one or more embodiments may include: a first capping layer arranged outside the first electrode and including the condensed cyclic compound according to one or more embodiments; a second capping layer arranged outside the second electrode and including the condensed cyclic compound according to one or more embodiments; or the first capping layer and the second capping layer.
In the light-receiving device according to one or more embodiments, the interlayer may further include a photoelectric conversion material.
In the light-receiving device according to one or more embodiments, the photoelectric conversion material may include a compound represented by Formula 2:
In the light-receiving device according to one or more embodiments, the photoelectric conversion material may include a compound represented by one of Formulae 2-1 to 2-6:
In the light-receiving device according to one or more embodiments, the photoelectric conversion material may be one selected from Compounds N1 to N43:
In the light-receiving device according to one or more embodiments,
In one or more embodiments, an electronic apparatus may include the light-receiving device according to one or more embodiments of the present disclosure.
The electronic apparatus according to one or more embodiments may further include a thin-film transistor,
The electronic apparatus according to one or more embodiments may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, a light-guiding layer, a light-blocking layer, or any combination thereof. The light-guiding layer and the light-blocking layer may be formed on an identical layer, and may form an arbitrary light-guiding pattern and/or an arbitrary light-blocking pattern.
In one or more embodiments, an electronic device may include the light-receiving device according to one or more embodiments, and the electronic device may be a display including the light-receiving device. For example, the electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, 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 microdisplay, a three-dimensional (3D) display, or a virtual reality or augmented reality display.
In some embodiments, the electronic device may be a product that may include a display, such as a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a biometric authentication device, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, or a signboard.
The condensed cyclic compound according to one or more embodiments may include at least one first repeating unit and at least one second repeating unit, and the first repeating unit may include at least one π electron-rich C1-C60 group. The second repeating unit may function as an electron-withdrawing group, and the π electron-rich C1-C60 group may function as an electron-donating group. In some embodiments, the first repeating unit may extend a conjugation system included in the second repeating unit and/or the π electron-rich C1-C60 group.
In some embodiments, due to the inclusion of the first repeating unit, direct bonding between the second repeating unit and the π electron-rich C1-C60 group may be limited, and thus, bonding of electrons and holes formed in the condensed cyclic compound may be delayed, and the condensed cyclic compound may provide improved stability.
In some embodiments, due to the inclusion of the first repeating unit between the second repeating unit and the π electron-rich C1-C60 group, the conjugation system included in the second repeating unit and/or the π electron-rich C1-C60 group may be extended. For example, as shown in Resonance structure 1, an unshared electron pair and/or a π electron pair of the π electron-rich C1-C60 group (indicated by EDG) may be delocalized in the second repeating unit, and the conjugation system formed in the second repeating unit may be extended by at least two allyl moieties. In Resonance Structure 1, EWG may correspond to R7 and R8 of Formulae 2-1 and 2-2.
In some embodiments, by changing aspects of linkage between the first repeating unit and the second repeating unit included in the condensed cyclic compound of the present disclosure, a linking site of the first repeating unit and/or a linking site of the second repeating unit, and the type or kind and a linking site of the π electron-rich C1-C60 group, physical properties, such as the light-absorption wavelength, of the condensed cyclic compound may be adjusted, and the thermal stability and deposition stability thereof may be improved.
In particular, an increase in the length of a conjugation system may lead to an increase in the HOMO energy level and a decrease in the LUMO energy level of the condensed cyclic compound, and may further cause an increase in the maximum light-absorption wavelength (Amax) thereof.
For example, as shown in Resonance Structure 2, when the shortest conjugation system connecting an electron-donating group included in the π electron-rich C1-C60 group to R7 of the second repeating unit includes 9 or more pairs of π electrons (including unshared electron pairs), the maximum light-absorption wavelength may be identified in the red wavelength region. It may be confirmed that the shortest conjugation system of the condensed cyclic compound shown in Resonance Structure 2 includes a total of 9 pairs of π electron pairs and unshared electron pairs.
In some embodiments, as shown in Resonance Structure 3, when the shortest conjugation system connecting the π electron-rich C1-C60 group to R7 of the second repeating unit includes less than 9 pairs of π electrons (including unshared electron pairs), the maximum light-absorption wavelength may be identified in the green wavelength region. It may be confirmed that the shortest conjugation system of the condensed cyclic compound shown in Resonance Structure 3 includes a total of 8 pairs of π electron pairs and unshared electron pairs.
In some embodiments, the electron-donating group included in the π electron-rich C1-C60 group may include a delocalizable σ electron pair, for example, a delocalizable π electron pair or a delocalizable unshared electron pair. When the σ electron pair is the only delocalizable electron pair of the electron-donating group, the conjugation system may be extended by hyperconjugation. When the electron-donating group includes a π electron pair or an unshared electron pair, extension of the conjugation system may be confirmed through the resonance structure as described above.
In determination of the shortest conjugation system, an unshared electron pair, a π electron pair, and a σ electron pair may have decreasing priority in the stated order as the starting point of the conjugation system. For example, when the electron-donating group includes both (e.g., simultaneously) an unshared electron pair and a π electron pair, the unshared electron pair becomes the starting point of the shortest conjugation system. Likewise, when the electron-donating group includes only a π electron pair and a σ electron pair, the π electron pair becomes the starting point of the conjugation system.
In some embodiments, when the electron-donating group includes two or more electron pairs of the same priority, the shortest conjugation system may be one in which the number of allyl moieties involved in resonance-induced delocalization is smaller.
As described above, the condensed cyclic compound of the present disclosure may further include the first repeating unit, thereby diversifying aspects of linkage between the second repeating unit and the π electron-rich C1-C60 group. As a result, the light-absorption wavelength of the condensed cyclic compound may be controlled or selected, and the thermal stability and deposition stability thereof may be improved.
In one or more embodiments, the light-receiving device of the present disclosure may include a first electrode (anode), a second electrode (cathode), and an interlayer between the first electrode and the second electrode and including a light-receiving layer. Furthermore, in some embodiments, the light-receiving device of the present disclosure may include: i) a hole transport region between the first electrode and the light-receiving layer and including a hole injection layer, a hole transport layer, an auxiliary layer, an electron-blocking layer, or any combination thereof; and ii) an electron transport region between the light-receiving layer and the second electrode and including a hole-blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
In some embodiments, because the light-receiving device of the present disclosure further includes the electron transport region and the hole transport region, electrons and holes formed in the light-receiving layer may be transferred more efficiently, and deterioration of the light-receiving layer due to absorption of light energy may be suppressed or reduced. As a result, the external quantum efficiency of the light-receiving device may be improved, and the lifespan of the light-receiving device may be improved.
In particular, the light-receiving device of the present disclosure may be to absorb green light and/or red light belonging to a relatively long wavelength range, and because light energy of green light and red light may be converted into electrical energy, side reactions and decomposition in the light-receiving layer due to absorption of high energy wavelengths may be suppressed or reduced. As a result, the lifespan of the light-receiving device may be further improved.
Synthesis methods of the condensed cyclic compound including the first repeating unit and the second repeating unit may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided herein.
At least one of the condensed cyclic compounds including the first repeating unit and the second repeating unit may be utilized in a light-receiving device (e.g., an organic light-receiving device). Accordingly, provided is a light-receiving device including: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including a light-receiving layer; and the condensed cyclic compound as described herein.
The expression “(interlayer and/or capping layer) includes a condensed cyclic compound” as utilized herein may be understood as “(interlayer and/or capping layer) may include one kind or type of condensed cyclic compound represented by Formula 1 or two different kinds or types of condensed cyclic compounds, each represented by Formula 1.”
For example, the interlayer and/or the capping layer may include Compound 1 only as the condensed cyclic compound. In this regard, Compound 1 may be present in the light-receiving layer of the light-receiving device. In one or more embodiments, the interlayer may include Compound 1 and Compound 2 as the condensed cyclic compound. In this regard, Compound 1 and Compound 2 may be present in an identical layer (e.g., Compound 1 and Compound 2 may both (e.g., simultaneously) be present in the light-receiving layer), or may be present in different layers (e.g., Compound 1 may be present in the light-receiving layer, and Compound 2 may be present in the electron transport region).
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 light-receiving device.
According to one or more aspects of embodiments of the present disclosure, provided is an electronic apparatus including the light-receiving device as described above. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-receiving device may be electrically connected to the source electrode or the drain electrode. The electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For more details on the electronic apparatus, related descriptions provided herein may be referred to.
Hereinafter, the structure of the light-receiving device 10 according to one or more embodiments and a method of manufacturing the light-receiving device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be on the first electrode 110. The interlayer 130 may include a light-receiving layer.
In one or more embodiments, the interlayer 130 may further include a hole transport region arranged between the first electrode 110 and the light-receiving layer and an electron transport region arranged between the light-receiving layer and the second electrode 150.
In one or more embodiments, the interlayer 130 may further include inorganic materials, such as quantum dots, in addition to one or more suitable organic materials.
In one or more embodiments, the interlayer 130 may include i) two or more light-receiving units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a transparent conductive layer arranged between the two or more light-receiving units. When the interlayer 130 includes the light-receiving units and the transparent conductive layer as described above, the light-receiving device 10 may be a tandem light-receiving device. For details on the transparent conductive layer, the description of the first electrode 110 may be referred to.
The hole transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an auxiliary layer, an electron-blocking layer, or any combination thereof.
For example, in some embodiments, 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/auxiliary layer structure, a hole injection layer/auxiliary layer structure, a hole transport layer/auxiliary layer structure, or a hole injection layer/hole transport layer/electron-blocking layer structure, the layers of each structure being stacked sequentially from the first electrode 110 in the stated order.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
For example, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY217:
In one or more embodiments, 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 one or more embodiments, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one selected from Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY203, and may include at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one selected from Formulae CY201 to CY217.
For example, in one or more embodiments, the hole transport region may include at least one selected from Compounds HT1 to HT46, 4,4′,4″-[tris(3-methylphenyl)phenylamino] triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), N,N′-di(1-naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB (NPD)), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (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), and/or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, 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 auxiliary layer may increase light-absorption efficiency by compensating for an optical resonance distance according to the wavelength of light absorbed by the light-receiving layer, and the electron-blocking layer may block or reduce the leakage of electrons from the light-receiving layer to the hole transport region. Materials that may be included in the hole transport region may be included in the auxiliary layer and the electron-blocking layer.
p-Dopant
In one or more embodiments, the hole transport region may further include, in addition to the materials as described above, a charge-generation material for improving conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer including (e.g., consisting of) a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the LUMO energy level of the p-dopant may be −3.5 eV or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/or the like.
Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f: 2′,3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), a compound represented by Formula 221, and/or the like:
In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Non-limiting examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and/or a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Non-limiting examples of the metalloid may include silicon (Si), antimony (Sb), and/or tellurium (Te).
Non-limiting examples of the non-metal may include oxygen (O) and/or halogen (e.g., F, Cl, Br, I, etc.).
Non-limiting examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, and/or any combination thereof.
Non-limiting examples of the metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and/or a rhenium oxide (e.g., ReO3, etc.).
Non-limiting examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and/or a lanthanide metal halide.
Non-limiting examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and/or CsI.
Non-limiting examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mgl2, Cal2, SrI2, and/or BaI2.
Non-limiting examples of the transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (e.g., ZrF4, ZrC14, ZrBr4, Zr14, etc.), a hafnium halide (e.g., HfF4, HfCl4, HfBr4, Hfl4, etc.), a vanadium halide (e.g., VF3, VCl3, VBr3, VI3, etc.), a niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, Ta13, etc.), a chromium halide (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, Mol3, etc.), a tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), a manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, Agl, etc.), and/or a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.).
Non-limiting examples of the post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (e.g., Ink3, etc.), and/or a tin halide (e.g., SnI2, etc.).
Non-limiting examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and/or SmI3.
Non-limiting examples of the metalloid halide may include an antimony halide (e.g., SbCl5, etc.).
Non-limiting examples of the metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), a post-transition metal telluride (e.g., ZnTe, etc.), and/or a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
When the light-receiving device 10 is a full-color light-receiving device, the light-receiving layer may be patterned into a red light-receiving layer, a green light-receiving layer, and/or a blue light-receiving layer, according to a sub-pixel. In one or more embodiments, the light-receiving layer may have a stacked structure of two or more layers selected from a red light-receiving layer, a green light-receiving layer, and a blue light-receiving layer, in which the two or more layers contact each other or are separated from each other to receive (e.g., absorb) white light. In one or more embodiments, the light-receiving layer may include two or more materials selected from a red light-receiving material, a green light-receiving material, and a blue light-receiving material, in which the two or more materials are mixed with each other in a single layer to receive white light.
The light-receiving layer may include a light-receiving compound. The light-receiving compound may include an organic compound, an inorganic compound, or an organic compound and an inorganic compound.
In some embodiments, the light-receiving compound included in the light-receiving layer may be the condensed cyclic compound including the first repeating unit and the second repeating unit.
An amount of the light-receiving compound in the light-receiving layer may be in a range of about 0.01 part by weight to about 15 parts by weight based on total 100 parts by weight of the light-receiving layer.
In one or more embodiments, the light-receiving layer may further include a quantum dot.
In one or more embodiments, the light-receiving layer may further include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the light-receiving layer.
A thickness of the light-receiving layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-receiving layer is within these ranges, excellent or suitable light-receiving characteristics may be obtained without substantial deterioration due to light absorption.
In one or more embodiments, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21, Formula 301
For example, in some embodiments, 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 one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, in some embodiments, the host may include a Be complex (e.g., Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include at least one selected from among Compounds H1 to H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and/or any combination thereof:
The electron transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron transport region may include a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
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, or a buffer layer/electron transport layer/electron injection layer structure, the layers of each structure being sequentially stacked from the light-receiving layer in the stated order.
In one or more embodiments, the electron transport region (e.g., 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 including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.
For example, in some embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21, Formula 601
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In one or more 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 one or more embodiments, the electron transport region may include at least one selected from among Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolinato)aluminium (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAIq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole-blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, 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. When the thicknesses of the buffer layer, the hole-blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron-transporting characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metal-containing material, in addition to the materials as described above.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
In one or more embodiments, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
The electron injection layer may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof.
The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include an alkali metal oxide, such as Li2O, Cs2O, or K2O, an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying the condition of 0<x<1), or BaxCa1-xO (wherein x is a real number satisfying the condition of 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and/or Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, and ii) a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in some embodiments, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be on the interlayer 130. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be utilized.
The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be arranged outside the first electrode 110, and/or a second capping layer may be arranged outside the second electrode 150. In some embodiments, the light-receiving device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in the light-receiving layer of the interlayer 130 of the light-receiving device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, or light generated in the light-receiving layer of the interlayer 130 of the light-receiving device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external light-receiving efficiency according to the principle of constructive interference.
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.
In some embodiments, the inorganic capping layer or the organic-inorganic composite capping layer may include the condensed cyclic compound including the first repeating unit and the second repeating unit.
At least one selected from among the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include an amine group-containing compound.
For example, in some embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one selected from among the first capping layer and the second capping layer may each independently include at least one selected from among Compounds HT28 to HT33, at least one selected from among Compounds CP1 to CP6, β-NPB, and/or any combination thereof:
The condensed cyclic compound of the present disclosure as described herein may be included in one or more suitable films. Accordingly, one or more aspects of embodiments of the present disclosure ae directed toward a film including the condensed cyclic compound. The film may be, for example, an optical member (or a light control means) (e.g., a color filter, a color conversion member, a capping layer, a light-extraction efficiency improvement layer, a selective light-absorbing layer, a polarizing layer, a quantum dot-containing layer, etc.), a light-blocking member (e.g., a light-reflecting layer, a light-absorbing layer, etc.), a protection member (e.g., an insulating layer, a dielectric material layer, etc.), and/or the like.
The light-receiving device may be included in one or more suitable electronic apparatuses. For example, in one or more embodiments, the electronic apparatus including the light-receiving device may be an electronic apparatus, an authentication apparatus, and/or the like.
In one or more embodiments, the electronic apparatus may further include, in addition to the light-receiving 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 arranged in at least one direction in which light received by the light-receiving device travels. For example, the light received by the light-receiving device may be blue light or white light. The light-receiving device may be the same as described above. In one or more 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, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be arranged 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 arranged among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.
The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum light-receiving wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the color filter areas (or the color conversion areas) may include quantum dots. In detail, 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. For details on the quantum dot, related descriptions provided herein may be referred to. The first area, the second area, and/or the third area may each further include a scatterer.
For example, the light-receiving device may be to receive first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be 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 light-receiving wavelengths. In detail, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-receiving device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode or the drain electrode may be electrically connected to the first electrode or the second electrode of the light-receiving device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The active 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 light-receiving device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-receiving device. The sealing portion may allow light for the light-receiving device to be absorbed from the outside, and may concurrently (e.g., simultaneously) prevent or reduce ambient air and moisture from penetrating into the light-receiving device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
Various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic apparatus. Non-limiting examples of 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 be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (e.g., fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-receiving device, a biometric information collector.
The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The electronic apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be arranged on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be arranged on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor, such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.
An interlayer insulating film 250 may be arranged on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be arranged on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be in contact with the exposed portions of the source region and the drain region of the active layer 220, respectively.
The TFT may be electrically connected to a light-receiving device to drive the light-receiving device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-receiving device may be provided on the passivation layer 280. The light-receiving device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.
A pixel-defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel-defining layer 290 may expose a portion of the first electrode 110, and the interlayer 130 may be formed in the exposed portion of the first electrode 110. The pixel-defining layer 290 may be a polyimide or polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining layer 290 to be arranged in the form of a common layer.
The second electrode 150 may be arranged on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be arranged on the capping layer 170. The encapsulation portion 300 may be arranged on a light-receiving device to protect the light-receiving device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film and the organic film.
The electronic apparatus of
The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. A display apparatus of the electronic device 1 may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA. The light-receiving device may be to absorb incident light through the display area DA, or may be to absorb incident light through the non-display area NDA.
The non-display area NDA may be an area in which an image is not displayed, and may entirely surround the display area DA. A driver for providing electrical signals or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.
In the electronic device 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. For example, as shown in
Respective layers included in the hole transport region, the light-receiving layer, and respective layers included in the electron transport region may be formed in a certain region by utilizing one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and/or laser-induced thermal imaging (LITI).
When layers constituting the hole transport region, the light-receiving layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group including (e.g., consisting of) carbon only as a ring-forming atom and having 3 to 60 carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has 1 to 60 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 including (e.g., 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 may have 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 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refers to a heterocyclic group that has 1 to 60 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 (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is utilized. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Non-limiting 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-C1 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. Non-limiting examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C1 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C1 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and non-limiting examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as 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 non-limiting examples thereof may include 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 non-limiting examples thereof may include an ethynyl group and a propynyl group. 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 non-limiting examples thereof may 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 non-limiting examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C1 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and non-limiting examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C1 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 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof may include 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 that further includes, in addition to carbon atoms, at least one heteroatom as a ring-forming atom and has at least one double bond in its ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as 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-C6a arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms, and the term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings condensed with each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings condensed with each other, at least one heteroatom other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as utilized herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as utilized herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as utilized herein refers to:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 as utilized herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group.
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “third-row transition metal” utilized herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
“Ph” as utilized herein refers to a phenyl group, “Me” as utilized herein refers to a methyl group, “Et” as utilized herein refers to an ethyl group, “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and “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.
* and *′ as utilized herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
The x-axis, y-axis, and z-axis as utilized herein 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.
Hereinafter, compounds according to embodiments and light-receiving devices according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
10 g (38.9 mmol) of 2-iodoselenophene and 7.8 g (32 mmol) of 1-bromo-9H-carbazole were dissolved in 40 mL of dioxane. 0.35 g (1.8 mmol) of copper (I) iodide, 0.70 g (6.09 mmol) of trans-1,2-cyclohexanediamine, and 12.9 g (61.0 mmol) of tripotassium phosphate were added thereto, and the resultant reaction solution was refluxed while heating for 30 hours. The resultant product was separated and purified by silica gel column chromatography (volume ratio of hexane:ethyl acetate as an eluent=5:1), and 8.4 g (yield: 70%) of Intermediate 1-A was obtained. The obtained compound was identified by MS/FAB.
C16H10BrNSe: calc. 375.14, found 375.18 .
8.4 g (22.0 mmol) of Intermediate 1-A was dissolved in 250 mL of dehydrated diethyl ether. 8 mL (32.0 mmol) of a hexane solution including 2.76 M n-butyl lithium (n-BuLi) was added dropwise thereto at −50° C., and the resultant reaction solution was stirred at room temperature for 1 hour. 1.3 g (25 mmol) of dehydrated acetone (or dimethyl ketone) (CH3COCH3) was added thereto at −50° C., and the resultant reaction solution was stirred at room temperature for 2 hours. An organic layer extracted therefrom utilizing dehydrated diethyl ether was washed with an aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The resultant product was separated and purified by silica gel column chromatography (performed while changing the volume ratio of solvent, hexane:dichloromethane as an eluent=100:0 to 50:50), and 5.1 g (yield: 66%) of Intermediate 1-B was obtained. The obtained compound was identified by MS/FAB.
C16H17NOSe: calc. 354.32, found 355.18 .
5.1 g (14.3 mmol) of Intermediate 1-B was dissolved in 180 mL of dichloromethane. 4.98 g (35.5 mmol) of a boron trifluoride-ethyl ether complex was added dropwise thereto at 0° C., and the resultant reaction solution was stirred for 2 hours. An organic layer extracted from dichloromethane was washed with an aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The resultant product was separated and purified by silica gel column chromatography (volume ratio of hexane:dichloromethane as an eluent=50:50), and 4.09 g (yield: 85%) of Intermediate 1-C was obtained. The obtained compound was identified by MS/FAB.
C19H15NSe: calc. 336.31, found 336.42 .
4.09 g (12.1 mmol) of Intermediate 1-C, 3.76 g (13.3 mmol) of 4-bromoiodobenzene, 1.16 g (1.00 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), and 2.48 g (17.92 mmol) of K2CO3 were dissolved in 120 mL of a mixed solution of THF/H2O (volume ratio of 2:1), and the resultant reaction solution was stirred at 70° C. for 5 hours. The reaction solution was cooled to room temperature, 40 mL of water was added to thereto, and an organic layer was extracted therefrom three times utilizing 50 mL of ethyl ether. The collected organic layer was dried with magnesium sulfate, the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel column chromatography, and 3.72 g (yield: 74%) of Intermediate 1-D was obtained. The obtained compound was identified by MS/FAB.
C19H14BrNSe: calc. 415.20, found 415.39 .
3.72 g (8.96 mmol) of Intermediate 1-D, 2.28 g (8.96 mmol) of bis(pinacolato)diboron, 0.36 g (0.5 mmol) of PdCl2(dppf)2, and 2.94 g (30.0 mmol) of KOAc were dissolved in 40 mL of DMSO, and the resultant reaction solution was stirred at 80° C. for 6 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times utilizing 50 mL of water and 50 mL of diethyl ether. The obtained organic layer was dried with magnesium sulfate, the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel column chromatography, and 3.3 g (yield: 80%) of Intermediate 1-E was obtained. The obtained compound was identified by MS/FAB.
C25H26BNO2Se: calc. 462.27, found 462.35 .
3.3 g (7.14 mmol) of Intermediate 1-E, 2.19 g (7.14 mmol) of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile, 116 g (1.00 mmol) of Pd(PPh3)4, and 2.48 g (17.92 mmol) of K2CO3 were dissolved in 120 mL of a mixed solution of THF/H2O (volume ratio of 2:1), and the resultant reaction solution was stirred at 70° C. for 5 hours. The reaction solution was cooled to room temperature, 60 mL of water was added to thereto, and an organic layer was extracted therefrom three times utilizing 80 mL of ethyl ether. The collected organic layer was dried with magnesium sulfate, the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel column chromatography, and 2.97 g (yield: 74%) of Compound 1 was obtained. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.57-8.55 (m, 1H), 8.29-8.11 (m, 3H), 7.71-7.67 (m, 2H), 7.53-7.41 (m, 4H), 7.36-7.08 (m, 4H), 6.86 (s, 1H), 1.46 (s, 6H)
C35H21N3Se: calc. 562.55, found 562.75 .
Compound 3 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 4-bromo-9H-acridine was utilized instead of 1-bromo-9H-carbazole during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.29-8.25 (m, 1H), 7.53-7.41 (m, 5H), 7.37-7.14 (m, 7H), 6.95-6.86 (m, 2H), 1.69 (s, 6H), 1.46 (s, 6H)
C38H27N3Se: calc. 604.63, found 604.75 .
Intermediate 5-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-A, except that 2-bromo-5-iodoselenophene and carbazole were utilized instead of 2-iodoselenophene and 1-bromo-9H-carbazole during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C16H10BrNSe: calc. 375.14, found 375.31 .
Intermediate 5-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that 2-(3-bromo-9H-fluoren-9-ylidene)propanedinitrile was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C22H19BN2O2: calc. 354.22, found 354.31 .
Compound 5 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 5-A and Intermediate 5-B were respectively utilized instead of 2.19 g (7.14 mmol) of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.56 (d, 1H), 8.29-8.11 (m, 3H), 7.90 (s, 1H), 7.53-7.36 (m, 8H), 7.20-7.10 (m, 4H)
C32H17N3Se: calc. 522.48, found 523.56 .
Intermediate 7-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-A, except that iodobenzene and 2-bromo-4H-thieno[3,2-b]indole were respectively utilized instead of 2-iodoselenophene and 1-bromo-9H-carbazole during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C16H10BrNS: calc. 328.23, found 328.41 .
Compound 7 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 7-A and Intermediate 5-B were respectively utilized instead of 2.19 g (7.14 mmol) of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.43-8.40 (m, 1H), 8.29-8.27 (m, 1H), 7.89-7.24 (m, 15H)
C32H17N3S: calc. 475.57, found 476.02 .
4.50 g (20.0 mmol) of N-phenyl-1-benzothiophen-3-amine, 5.78 g (20.0 mmol) of 3-bromo-2-iodothiophene, 0.37 g (0.4 mmol) of Pd2(dba)3, 0.08 g (0.4 mmol) of P(t-Bu)3, and 5.76 g (60.0 mmol) of t-BuOK were dissolved in 90 mL of toluene, and the resultant reaction solution was stirred at 120° C. for 24 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times utilizing 50 mL of water and 50 mL of diethyl ether. The collected organic layer was dried with magnesium sulfate, the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel column chromatography, and 13.36 g (yield: 55%) of Intermediate 8-A was obtained. The obtained compound was identified by MS/FAB.
C18H11NS2: calc. 305.41, found 305.62 .
Intermediate 8-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-D, except that Intermediate 8-A was utilized instead of Intermediate 1-C during the synthesis of Intermediate 1-D in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C18H10BrNS2: calc. 384.31, found 384.33 .
Compound 8 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 8-B and Intermediate 5-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.27-8.25 (m, 1H), 8.07-8.05 (m, 1H), 7.93-7.10 (m, 15H)
C34H17N3S2: calc. 531.65, found 531.73 .
Compound 10 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that, in Synthesis Example 1, 2-iodothiophene was utilized instead of 2-iodoselenophene during the synthesis of Intermediate 1-A, 9H-fluoren-9-one was utilized instead of acetone during the synthesis of Intermediate 1-B, and 2-(3-bromo-9H-fluoren-9-ylidene)propanedinitrile was utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile during the synthesis of Compound 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.29-8.25 (m, 1H), 7.90-7.82 (m, 5H), 7.72-7.70 (m, 1H), 7.53-6.95 (m, 18H)
C45H25N3S: calc. 522.48, found 523.56 .
Compound 13 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 2-iodothiophene and 2-bromo-N-phenylaniline were respectively utilized instead of 2-iodoselenophene and 1-bromo-9H-carbazole during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.29-8.25 (m, 2H), 7.89-7.72 (m, 3H), 7.53-7.37 (m, 3H), 7.24-6.95 (m, 9H), 1.72 (s, 6H)
C35H23N3S: calc. 517.65, found 518.72 .
Intermediate 16-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 8-A, except that 4,4′-dimethyldiphenylamine and 2-bromo-5-iodothiophene were respectively utilized instead of N-phenyl-1-benzothiophen-3-amine and 3-bromo-2-iodothiophene during the synthesis of Intermediate 8-A in Synthesis Example 5. The obtained compound was identified by MS/FAB.
C18H17NSe: calc. 326.31, found 326.43 .
Compound 16 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 16-A and Intermediate 16-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.29-8.27 (m, 1H), 7.67-7.65 (m, 1H), 7.53-7.37 (m, 7H), 7.15-7.12 (m, 6H), 6.86 (s, 1H), 6.59 (s, 1H), 2.32 (s, 6H)
C34H23N3Se: calc. 552.55, found 552.73 .
Intermediate 29-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-A, except that methyl 2-iodobenzoate and carbazole were respectively utilized instead of 2-iodoselenophene and 1-bromo-9H-carbazole during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C20H15NO2: calc. 301.35, found 301.45 .
2.15 g (7.14 mmol) of Intermediate 29-A was dissolved in 100 mL of ether and cooled to −78° C., methyllithium (1.6 M in ether, 78 mL, 124.4 mmol) was added thereto, and the resultant reaction solution was stirred for 1 hours. The reaction solution was slowly heated to room temperature and further stirred for 4 hours. When the reaction was completed, an organic layer was extracted therefrom utilizing 200 mL of water, and the organic layer was dried under reduced pressure. The resultant product was recrystallized utilizing ethanol/acetone (volume ratio of 1:1) to obtain 1.441 g (yield: 67%) of Intermediate 29-B. The obtained compound was identified by MS/FAB.
C21H19NO: calc. 301.39, found 301.62 .
Intermediate 29-C was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-C, except that Intermediate 29-B was utilized instead of Intermediate 1-B during the synthesis of Intermediate 1-C in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C21H17N: calc. 283.37, found 283.41 .
Intermediate 29-D was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-D, except that Intermediate 29-C was utilized instead of Intermediate 1-C during the synthesis of Intermediate 1-D in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C21H16BrN: calc. 362.27, found 362.34 .
Intermediate 29-E was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate 29-D was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C27H28BNO2: calc. 409.34, found 409.39.
Intermediate 29-F was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 2-bromo-5-iodothiophene and Intermediate 29-E were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C25H18BrNS: calc. 444.39, found 444.62 .
Compound 29 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 29-F and Intermediate 5-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.57-8.55 (m, 1H), 8.29-8.27 (m, 1H), 8.09-8.07 (m, 1H), 7.94-7.72 (m, 7H), 7.53-7.35 (m, 7H), 7.06-7.07 (m, 2H), 1.69 (s, 6H)
C41H25N3S: calc. 591.73, found 591.79 .
Intermediate 39-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 8-A, except that N-phenyldibenzo[b,d]furan-3-amine and 2-bromo-5-iodothiophene were respectively utilized instead of N-phenyl-1-benzothiophen-3-amine and 3-bromo-2-iodothiophene during the synthesis of Intermediate 8-A in Synthesis Example 5. The obtained compound was identified by MS/FAB.
C22H14NOSBr: calc. 420.34, found 420.43 .
Compound 39 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate 39-A and Intermediate 5-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.29-8.27 (m, 1H), 8.03-7.72 (m, 6H), 7.53-7.24 (m, 8H), 7.08-6.85 (m, 5H), 6.15-6.13 (m, 1H)
C38H21N3OS: calc. 567.67, found 567.41 .
Intermediate 47-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-D, except that 7H-benz[de]anthracene,7,7-dimethyl was utilized instead of Intermediate 1-C during the synthesis of Intermediate 1-D in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C19H15Br: calc. 323.23, found 323.44 .
Intermediate 47-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate 47-A was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C25H27BO2: calc 370.30, found 370.40.
Intermediate 47-C was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 2-bromo-5-iodothiophene and Intermediate 47-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C23H17BrS: calc. 405.35, found 405.62 .
Intermediate 47-D was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate 47-C was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C29H29BO2S: calc 452.42, found 452.65 .
Compound 47 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that (E)-N-(3-bromo-9H-fluoren-9-ylidene)cyanamide and Intermediate 47-D were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.87-8.85 (m, 1H), 8.32-8.30 (m, 1H), 8.18 (s, 1H), 8.11-8.00 (m, 3H), 7.85-7.60 (m, 6H), 7.44-7.37 (m, 3H), 7.30-7.28 (m, 2H), 6.91-6.89 (m, 1H), 1.82 (s, 6H)
C37H24N2S: calc. 528.67, found 528.81.
Compound 48 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 4-bromo-9,9-dimethyl-9H-acridine and (E)-N-(3-bromo-9H-fluoren-9-ylidene)cyanamide were respectively utilized instead of 1-bromo-9H-carbazole and 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.00-7.96 (m, 2H), 7.85-7.60 (m, 4H), 7.48-7.46 (m, 2H), 7.32-7.30 (m, 1H), 7.19-7.14 (m, 5H), 6.95-6.93 (m, 1H), 1.69 (s, 6H), 1.46 (s, 6H)
C36H27N3Se: calc. 580.60, found 580.75 .
In a nitrogen atmosphere, 0.65 g (0.71 mmol) of Pd2(dba)3 and 0.21 g (0.71 mmol) of a P(t-Bu)3HBF4 ligand were added to 90 mL of toluene. 2.05 g (21.3 mmol) of NaOtBu and 2.30 g (7.1 mmol) of 3,3′-dibromo-2,2′-bithiophene were successively added thereto. After 5 minutes, arylamine (9.94 mmol) was added thereto, and the resultant reaction solution was stirred at 125° C. for 6 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times utilizing 50 mL of water and 50 mL of diethyl ether. The collected organic layer was dried with magnesium sulfate, the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel column chromatography, and 1.0 g (yield: 55%) of Intermediate R05-A was obtained. The obtained compound was identified by MS/FAB.
C14H9NS2: calc. 255.35, found 255.41 .
Intermediate R05-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-D, except that Intermediate R05-A was utilized instead of Intermediate 1-C during the synthesis of Intermediate 1-D in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C14H8BrNS2: calc. 334.25, found 334.29 .
Intermediate R05-C was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate R05-B was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C20H20BNO2S2: calc 381.32, found 381.40.
Compound R05 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 2-(2,7-dibromo-9H-fluoren-9-ylidene)malonitrile and Intermediate R05-C were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.16-8.14 (m, 2H), 7.91-7.84 (m, 4H), 7.62-7.50 (m, 10H), 7.31-7.29 (m, 2H), 7.12-7.08 (m, 4H)
C44H22N4S4: calc. 734.93, found 734.96 .
Intermediate R06-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 8-A, except that 5,6-dihydro-5-phenylindolo[2,3-b]indole and iodobenzene were respectively utilized instead of N-phenyl-1-benzothiophen-3-amine and 3-bromo-2-iodothiophene during the synthesis of Intermediate 8-A in Synthesis Example 5. The obtained compound was identified by MS/FAB.
C26H18N2: calc. 358.44, found 358.47 .
Intermediate R06-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-D, except that Intermediate R06-A was utilized instead of Intermediate 1-C during the synthesis of Intermediate 1-D in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C26H17BrN2: calc. 437.34, found 437.35 .
Intermediate R06-C was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate R06-B was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C32H29BN2O2: calc 484.41, found 484.44 .
Intermediate R06-D was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that 2-bromo-5-iodoselenophene and Intermediate R06-C were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C30H19BrN2Se: calc. 566.37, found 566.39 .
Compound R06 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that Intermediate R06-D and Intermediate 5-B were respectively utilized instead of 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile and Intermediate 1-E during the synthesis of Compound 1 in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.55-8.53 (m, 1H), 8.47 (s, 1H), 8.29 (d, 1H), 7.94-7.89 (m, 3H), 7.62-7.37 (m, 18H), 7.18-7.16 (m, 1H), 6.96-6.94 (m, 1H)
C46H26N4Se: calc. 713.71 found 713.73 .
Intermediate R07-A was synthesized in substantially the same manner as utilized to synthesize Intermediate 8-A, except that N,N-diphenylamine and 5,5′-dibromo-2,2′-bithiophene were respectively utilized instead of N-phenyl-1-benzothiophen-3-amine and 3-bromo-2-iodothiophene during the synthesis of Intermediate 8-A in Synthesis Example 5. The obtained compound was identified by MS/FAB.
C20H14BrNS2: calc. 412.36, found 412.39 .
Intermediate R07-B was synthesized in substantially the same manner as utilized to synthesize Intermediate 1-E, except that Intermediate R07-A was utilized instead of Intermediate 1-D during the synthesis of Intermediate 1-E in Synthesis Example 1. The obtained compound was identified by MS/FAB.
C26H26BNO2S2: calc 459.43, found 459.46 .
Compound R07 was synthesized in substantially the same manner as utilized to synthesize Compound 1, except that (E)-N-(3-bromo-9H-fluoren-9-ylidene)cyanamide and Intermediate R07-B were respectively utilized instead of 1-bromo-9H-carbazole and 2-(2-bromo-9H-fluoren-9-ylidene)propanedinitrile during the synthesis of Intermediate 1-A in Synthesis Example 1. The obtained compound was identified by 1H NMR (CDCl3, 400 MHz) and MS/FAB.
1H NMR: δ=8.32-8.30 (m, 1H), 8.18 (s, 1H), 8.11 (d, 1H), 8.00-7.98 (m, 1H), 7.85-7.83 (m, 1H), 7.69-7.60 (m, 2H), 7.51-7.49 (m, 1H), 7.34-7.32 (m, 1H), 7.24-7.20 (m, 4H), 7.08-7.00 (m, 7H), 6.05-6.02 (m, 1H)
C34H21N3S2: calc. 535.68, found 535.75.
1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples are shown in Table 1.
1H NMR (CDCl3, 400 MHz)
The LUMO and HOMO values of the compounds of Synthesis Examples and Comparative Compounds were measured utilizing the method described in Table 2. The results are shown in Table 3.
The structures of Comparative Compounds 1 and 2 are as follows.
A substrate having an ITO anode deposited thereon was cut to a size of 50 mm×50 mm×0.7 mm. The substrate was ultrasonically cleaned in isopropyl alcohol and pure water each for 5 minutes. Then, ultraviolet rays were irradiated onto the substrate for 30 minutes, and the substrate was cleaned by exposure to ozone. The cleaned substrate was loaded onto a vacuum deposition apparatus.
Compound 2-TNATA was vacuum-deposited on the ITO substrate to form a hole injection layer having a thickness of 600 Å. Then, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å. An auxiliary layer having a thickness of 300 Å was formed on the hole transport layer.
Compound 1 and Compound N1, which is a photoelectric conversion material, were co-deposited at a weight ratio of 20:80 on the auxiliary layer to form a light-receiving layer having a thickness of 500 Å. Alq3 was deposited on the light-receiving layer to form an electron transport layer having a thickness of 300 Å. LiF, which is an alkali metal halide, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Then, Al was vacuum-deposited thereon to form a LiF/Al cathode having a thickness of 3,000 Å, thereby completing the manufacture of a light-receiving device.
Light-receiving devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 4 were each utilized instead of Compound 1 in forming the light-receiving layer.
The light-receiving devices manufactured according to Examples 1 to 15 and Comparative Examples 1 and 2 were irradiated with light, and the external quantum efficiency (EQE, %) according to wavelength was measured for each device. The external quantum efficiency refers to the ratio of electrical energy generated from light. The results are shown in Table 4.
According to Table 4, it is confirmed that the light-receiving devices of Examples 1 to 15 evenly had high sensitivity and high efficiency, compared to the light-receiving devices of Comparative Examples 1 and 2.
According to one or more embodiments, a light-receiving device including a condensed cyclic compound according to one or more embodiments of the present disclosure may have high sensitivity and efficiency, easy control of light-absorption wavelength, and long lifespan.
Throughout the present disclosure, when a component such as a layer, a film, a region, or a plate is mentioned to be placed “on” another component, it will be understood that it may be directly on another component or that another component may be interposed therebetween. In some embodiments, “directly on” may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, “directly on” may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.
As utilized herein, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
As utilized herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation 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. “About” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, 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. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant 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-receiving device, the display device, the electronic apparatus, the electronic device, or any 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 device 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.
It should be understood that embodiments described herein 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 |
|---|---|---|---|
| 10-2022-0125778 | Sep 2022 | KR | national |
