Patent Application
20240287112
This application claims the benefit of and the priority to Korean Patent Application No. 10-2023-0012118 filed on Jan. 30, 2023 in the Korean Intellectual Property Office, the disclosure of which is hereby incorporated by reference in its entirety.
The present disclosure relates to an organometallic compound, and more particularly, to an organometallic compound having phosphorescent properties and an organic light-emitting diode including the same.
As a display device is applied to various fields, interest with the display device is increasing. One of the display devices is an organic light-emitting display device including an organic light-emitting diode (OLED) which is rapidly developing.
In the organic light-emitting diode, when electric charges are injected into a light-emitting layer formed between a positive electrode and a negative electrode, an electron and a hole are recombined with each other in the light-emitting layer to form an exciton and thus energy of the exciton is converted to light. Thus, the organic light-emitting diode emits the light. Compared to conventional display devices, the organic light-emitting diode may operate at a low voltage, consume relatively little power, render excellent colors, and may be used in a variety of ways because a flexible substrate may be applied thereto. Further, a size of the organic light-emitting diode may be freely adjustable.
The organic light-emitting diode (OLED) has superior viewing angle and contrast ratio compared to a liquid crystal display (LCD), and is lightweight and is ultra-thin because the OLED does not require a backlight. The organic light-emitting diode includes a plurality of organic layers between a negative electrode (electron injection electrode; cathode) and a positive electrode (hole injection electrode; anode). The plurality of organic layers may include a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, and a light-emitting layer, an electron transport layer, etc.
In this organic light-emitting diode structure, when a voltage is applied across the two electrodes, electrons and holes are injected from the negative and positive electrodes, respectively, into the light-emitting layer and thus excitons are generated in the light-emitting layer and then fall to a ground state to emit light.
Organic materials used in the organic light-emitting diode may be largely classified into light-emitting materials and charge-transporting materials. The light-emitting material is an important factor determining luminous efficiency of the organic light-emitting diode. The luminescent material must have high quantum efficiency, excellent electron and hole mobility, and must exist uniformly and stably in the light-emitting layer. The light-emitting materials may be classified into light-emitting materials emitting light of blue, red, and green colors based on colors of the light. A color-generating material may include a host and dopants to increase the color purity and luminous efficiency through energy transfer.
When the fluorescent material is used, singlets as about 25% of excitons generated in the light-emitting layer are used to emit light, while most of triplets as 75% of the excitons generated in the light-emitting layer are dissipated as heat. However, when the phosphorescent material is used, singlets and triplets are used to emit light.
Conventionally, an organometallic compound is used as the phosphorescent material used in the organic light-emitting diode. There is still a technical need to improve performance of an organic light-emitting diode by deriving a high-efficiency phosphorescent dopant material and applying a host material of optimal photophysical properties to improve diode efficiency and lifetime, compared to a conventional organic light-emitting diode.
Accordingly, an object of the present disclosure is to provide an organometallic compound capable of lowering operation voltage of an organic light-emitting diode, and improving efficiency and lifespan thereof, and an organic light-emitting diode including an organic light-emitting layer containing the same.
Objects of the present disclosure are not limited to the above-mentioned object. Other objects and advantages of the present disclosure that are not mentioned may be understood based on following descriptions, and may be more clearly understood based on aspects of the present disclosure. Further, it may be easily understood that the objects and advantages of the present disclosure may be realized using means shown in the claims and combinations thereof.
To achieve these and other advantages and in accordance with objects of the disclosure, as embodied and broadly described herein, an organometallic compound has a novel structure represented by a following Chemical Formula 1:
Ir(LA)n(LB)3-n [Chemical Formula 1]
A second aspect of the present disclosure provides an organic light-emitting diode including a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, wherein the light-emitting layer contains the organometallic compound according to the first aspect of the present disclosure.
A third aspect of the present disclosure provides an organic light-emitting display device including a substrate; a driving element located on the substrate; and an organic light-emitting diode disposed on the substrate and connected to the driving element, wherein the organic light-emitting diode includes the organic light-emitting diode according to the second aspect of the present disclosure.
The organometallic compound according to the present disclosure may be used as the dopant of the light-emitting layer of the organic light-emitting diode, such that the operation voltage of the organic light-emitting diode may be lowered, and the efficiency and lifespan characteristics of the organic light-emitting diode may be improved. Thus, a low power display device may be realized.
Effects of the present disclosure are not limited to the above-mentioned effects, and other effects not mentioned may be clearly understood by those skilled in the art from following descriptions.
It is to be understood that both the foregoing general description and the following detailed description of the present disclosure are merely by way of example and are intended to provide further explanation of the inventive concepts as claimed.
The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this application, illustrate embodiments of the disclosure and together with the description serve to explain principles of the disclosure.
Reference will now be made in detail to some of the examples and embodiments of the disclosure illustrated in the accompanying drawings. Wherever possible, the same reference numbers will be used throughout the drawings to refer to the same or like parts.
Advantages and features of the present disclosure, and a method of achieving the advantages and features will become apparent with reference to embodiments described later in detail together with the accompanying drawings. However, the present disclosure is not limited to the embodiments as disclosed below, but may be implemented in various different forms. Thus, these embodiments are set forth only to make the present disclosure complete, and to completely inform the scope of the present disclosure to those of ordinary skill in the technical field to which the present disclosure belongs, and the present disclosure is only defined by the scope of the claims. The same reference numbers in different drawings represent the same or similar elements.
Further, descriptions and details of well-known steps and elements are omitted for simplicity of the description. Furthermore, in the following detailed description of the present disclosure, numerous specific details are set forth in order to provide a thorough understanding of the present disclosure.
As used herein, the singular constitutes “a” and “an” are intended to include the plural constitutes as well, unless the context clearly indicates otherwise. It will be further understood that the terms “have”, “having”, “comprise”, “comprising”, “include”, and “including” when used herein, specify the presence of the stated features, integers, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, operations, elements, components, and/or portions thereof.
In interpreting a numerical value, the value is interpreted as including an error range unless there is no separate explicit description thereof.
In addition, it will also be understood that when a first element or layer is referred to as being present “on top of (or under)” a second element or layer, the first element may be disposed directly on top of (or under) the second element or may be disposed indirectly on top of (or under) the second element with a third element or layer being disposed between the first and second elements or layers.
As used herein, the term “halo” or “halogen” includes fluorine, chlorine, bromine and iodine.
As used herein, the term “alkyl group” refers to both linear alkyl radicals and branched alkyl radicals. Unless otherwise specified, the alkyl group contains 1 to 20 carbon atoms, and includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, etc. Further, the alkyl group may be optionally substituted.
As used herein, the term “cycloalkyl group” refers to a cyclic alkyl radical. Unless otherwise specified, the cycloalkyl group contains 3 to 20 carbon atoms, and includes cyclopropyl, cyclopentyl, cyclohexyl, and the like. Further, the cycloalkyl group may be optionally substituted.
As used herein, the term “alkenyl group” refers to both linear alkene radicals and branched alkene radicals. Unless otherwise specified, the alkenyl group contains 2 to 20 carbon atoms. Additionally, the alkenyl group may be optionally substituted.
As used herein, the term “alkynyl group” refers to both linear alkyne radicals and branched alkyne radicals. Unless otherwise specified, the alkynyl group contains 2 to 20 carbon atoms. Additionally, the alkynyl group may be optionally substituted.
The terms “aralkyl group” and “arylalkyl group” as used herein are used interchangeably with each other and refer to an alkyl group having an aromatic group as a substituent. Further, the arylalkyl group may be optionally substituted.
The terms “aryl group” and “aromatic group” as used herein are used in the same meaning. The aryl group includes both a monocyclic group and a polycyclic group. The polycyclic group may include a “fused ring” in which two or more rings are fused with each other such that two carbons are common to two adjacent rings. Unless otherwise specified, the aryl group contains 6 to 60 carbon atoms. Further, the aryl group may be optionally substituted.
The term “heterocyclic group” as used herein means that at least one of carbon atoms constituting an aryl group, a cycloalkyl group, or an aralkyl group (arylalkyl group) is substituted with a heteroatom such as oxygen (O), nitrogen (N), sulfur (S), etc. Further, the heterocyclic group may be optionally substituted.
The term “carbon ring” as used herein may be used as a term including both “cycloalkyl group” as an alicyclic group and “aryl group” an aromatic group unless otherwise specified.
The terms “heteroalkyl group” and “heteroalkenyl group” as used herein mean that at least one of carbon atoms constituting the group is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S). In addition, the heteroalkyl group and the heteroalkenyl group may be optionally substituted.
As used herein, the term “substituted” means that a substituent other than hydrogen (H) binds to corresponding carbon.
As used herein, a substituent may be interpreted as containing 1 to 30 carbon atoms unless there is a particular limitation on the number of carbon atoms, and the minimum number of carbon atoms that may be included in each substituent may be determined by what is known.
Unless specifically limited herein, the substituent may be deuterium, halogen, an alkyl group, a heteroalkyl group, an alkoxy group, an aryloxy group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carbonyl group, a carboxylic acid group, a nitrile group, a cyano group, an amino group, an alkylsilyl group, an arylsilyl group, a sulfonyl group, a phosphino group, and combinations thereof.
Subjects and substituents as defined in the present disclosure may be the same as or different from each other unless otherwise specified.
As used herein, ‘n substitution (n≥1)’ refers to the number of substituent sites when there are a plurality of substituent sites at which substituents instead of hydrogen basically binding to carbon may bind to carbon in a specific compound or a portion of the compound. Even when “unsubstituted” is not specified herein, this may be interpreted as presence of hydrogen basically binding to carbon unless a substituent binds thereto.
Hereinafter, a structure of an organometallic compound according to the present disclosure and an organic light-emitting diode including the same will be described in detail.
An organometallic compound represented by a following Chemical Formula 1 of the present disclosure is structurally characterized in that a fused polycyclic structure containing a boron (B) element is introduced thereto, compared to a conventional phenyl-pyridine metal complex. Thus, findings have been experimentally identified that when the organometallic compound represented by the Chemical Formula 1 is used as a dopant material of a phosphorescent light-emitting layer of the organic light-emitting diode, the light-emitting efficiency and lifetime of the organic light-emitting diode are improved, and an operation voltage thereof is lowered. In this way, the present disclosure has been completed.
Ir(LA)n(LB)3-n [Chemical Formula 1]
In the Chemical Formulas 1-1 to 1-3, each of R1, and R2 means a substituent that may bind to a moiety. As used herein, the definitions of R1, and R2 are applied to a case where R1, and R2 are present. When R1, and R2 are not present, the moiety is unsubstituted with the substituent, and hydrogen basically binds thereto.
Each of X1, X2 and X3 may independently represent N or CR3, and each of X4, X5, X6 and X7 may independently represent N or CR4,
When two or more R1s are present, two adjacent R1s may bind to each other to form cycloalkyl, cycloalkenyl, aryl or arylalkyl.
When two or more R2s are present, two adjacent R2s may bind to each other to form cycloalkyl, cycloalkenyl, aryl or arylalkyl.
When two or more R3s are present, two adjacent R3s may bind to each other to form cycloalkyl, cycloalkenyl, aryl or arylalkyl.
The LB may be a bidentate ligand represented by
According to one implementation of the present disclosure, the (X—Y) may have a structure represented by one of following Chemical Formula 2 or Chemical Formula 3:
In the Chemical Formula 2, each of R5-1, R5-2, R5-3, R5-4, R6-1, R6-2, R6-3 and R6-4 may independently represent one selected from a group consisting of hydrogen, deuterium, a C1 to C5 linear alkyl group, a C1 to C5 branched alkyl group, a C6 to C20 aryl group, and a C7 to C30 arylalkyl group.
Optionally, at least one hydrogen of the C1 to C5 linear alkyl group, the C1 to C5 branched alkyl group, the C6 to C20 aryl group, or the C7 to C30 arylalkyl group selected as R5-1, R5-2, R5-3, R5-4, R6-1, R6-2, R6-3 or R64 may be substituted with deuterium or a halogen element.
Optionally, two groups adjacent to each other among R5-1, R5-2, R5-3 and R5-4 may bind to each other to form a ring structure. Two groups adjacent to each other among R6-1, R6-2, R6-3 and R64 may bind to each other to form a ring structure.
In the Chemical Formula 3, each of R7, R8 and R9 may independently represent one selected from a group consisting of hydrogen, deuterium, a C1 to C5 linear alkyl group and a C1 to C5 branched alkyl group. Optionally, at least one hydrogen of the C1 to C5 linear alkyl group or the C1 to C5 branched alkyl group selected as R7, R8 or R9 may be substituted with deuterium or a halogen element.
Optionally, two groups adjacent to each other among R7, R8 and R9 may bind to each other to form a ring structure.
According to one implementation of the present disclosure, n may be 1, n may be 2, or n may be 3. Preferably, for example, the compound represented by the above Chemical Formula 1 may have a heteroleptic structure where n in the Chemical Formula 1 is 1. For example, the compound represented by the above Chemical Formula 1 may have a heteroleptic structure where n in the Chemical Formula 1 is 2.
According to one implementation of the present disclosure, all of Zs may be O (oxygen).
According to one implementation of the present disclosure, all of Zs may be S (sulfur).
According to one implementation of the present disclosure, all of Zs may be Se (selenium).
According to one implementation of the present disclosure, all of Zs may be NRA, and in this case, each of RAS may independently represent a C1 to C3 alkyl group.
According to one implementation of the present disclosure, R1 may not be present or, when being present, R1 may represent mono-substitution or di-substitution.
According to one implementation of the present disclosure, when R1 is present, each R1 may independently represent one of a C1 to C10 linear alkyl group, a C1 to C10 branched alkyl group, a C6 to C20 aryl group and a C7 to C30 arylalkyl group. In this regard, optionally, at least one hydrogen of the C1 to C10 linear alkyl group, the C1 to C10 branched alkyl group, the C6 to C20 aryl group or the C7 to C30 arylalkyl group selected as R1 may be substituted with deuterium.
According to one implementation of the present disclosure, when R1 represents di-substitution, and two R1s are adjacent to each other, the two R1s may bind to each other to form a ring structure, preferably, a 5-membered or 6-membered cycloalkyl group or aryl group. Optionally, at least one hydrogen of the cycloalkyl group or aryl group may be substituted with deuterium.
According to one implementation of the present disclosure, R2 may be absent.
According to one implementation of the present disclosure, each of X1, X2, and X3 may be CR3. In this case, all of R3s may be hydrogen.
According to one implementation of the present disclosure, each of X4, X5, X6 and X7 may be CR4. In this case, all of R4s may be hydrogen.
According to one implementation of the present disclosure, the compound represented by the Chemical Formula 1 may be used as a green phosphorescent material. However, the present disclosure is not necessarily limited thereto.
A specific example of the compound represented by the Chemical Formula 1 of the present disclosure may be one selected from a group consisting of following Compounds 1 to 828. However, the specific example of the compound represented by the Chemical Formula 1 of the present disclosure is not limited thereto as long as it meets the above definition of the Chemical Formula 1:
Referring to
The first electrode 110 may act as a positive electrode, and may be made of ITO, IZO, tin-oxide, or zinc-oxide as a conductive material having a relatively large work function value. However, the present disclosure is not limited thereto.
The second electrode 120 may act as a negative electrode, and may include Al, Mg, Ca, or Ag as a conductive material having a relatively small work function value, or an alloy or combination thereof. However, the present disclosure is not limited thereto.
The hole injection layer 140 may be positioned between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 may include a compound selected from a group consisting of MTDATA, CuPc, TCTA, NPB(NPD), HATCN, TDAPB, PEDOT/PSS, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, NPNPB (N,N′-diphenyl-N,N′-di[4-(N,N-diphenyl-amino)phenyl]benzidine), etc. Preferably, the hole injection layer 140 may include NPNPB. However, the present disclosure is not limited thereto.
The hole transport layer 150 may be positioned adjacent to the light-emitting layer and between the first electrode 110 and the light-emitting layer 160. A material of the hole transport layer 150 may include a compound selected from a group consisting of TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine, etc. However, the present disclosure is not limited thereto.
According to the present disclosure, the light-emitting layer 160 may be formed by doping the host material 160″ with the organometallic compound represented by the Chemical Formula 1 as the dopant 160′ in order to improve luminous efficiency of the diode 100. The organometallic compound represented by the Chemical Formula 1 may be used as a green or red light-emitting material, and preferably as a green phosphorescent material.
In one implementation of the present disclosure, a doping concentration of the dopant 160′ according to the present disclosure may be adjusted to be within a range of 1 to 30% by weight based on a total weight of the host material 160″. However, the disclosure is not limited thereto. For example, the doping concentration may be in a range of 2 to 20 wt %, for example, 3 to 15 wt %, for example, 5 to 10 wt %, for example, 3 to 8 wt %, for example, 2 to 7 wt %, for example, 5 to 7 wt %, or for example, 5 to 6 wt %.
The light-emitting layer 160 according to the present disclosure contains the host material 160′ which is known in the art and may achieve an effect of the present disclosure while the layer 160 contains the organometallic compound represented by the Chemical Formula 1 as the dopant 160″. For example, in accordance with the present disclosure, the host material 160′ may include ne host material selected from a group consisting of CBP (carbazole biphenyl), mCP (1,3-bis(carbazol-9-yl), and the like. However, the disclosure is not limited thereto.
Further, the electron transport layer 170 and the electron injection layer 180 may be sequentially stacked between the light-emitting layer 160 and the second electrode 120. A material of the electron transport layer 170 requires high electron mobility such that electrons may be stably supplied to the light-emitting layer under smooth electron transport.
For example, the material of the electron transport layer 170 may include a compound selected from a group consisting of Alq3 (tris(8-hydroxyquinolino)aluminum), Liq (8-hydroxyquinolinolatolithium), PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium), SAlq, TPBi (2,2′,2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, and ZADN (2-[4-(9,10-Di-2-naphthalen2-yl-2-anthracen-2-yl)phenyl]-1-phenyl-1H-benzoimidazole). Preferably, the material of the electron transport layer 170 may include ZADN. However, the present disclosure is not limited thereto.
The electron injection layer 180 serves to facilitate electron injection. A material of the electron injection layer may include a compound selected from a group consisting of Alq3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. However, the present disclosure is not limited thereto. Alternatively, the electron injection layer 180 may be made of a metal compound. The metal compound may include, for example, one or more selected from a group consisting of Liq, LiF, NaF, KF, RbF, CsF, FrF, BcF2, MgF2, CaF2, SrF2, BaF2 and RaF2. However, the present disclosure is not limited thereto.
The organic light-emitting diode according to the present disclosure may be embodied as a white light-emitting diode having a tandem structure. The tandem organic light-emitting diode according to an illustrative embodiment of the present disclosure may be formed in a structure in which adjacent ones of two or more light-emitting stacks are connected to each other via a charge generation layer (CGL). The organic light-emitting diode may include at least two light-emitting stacks disposed on a substrate, wherein each of the at least two light-emitting stacks includes first and second electrodes facing each other, and the light-emitting layer disposed between the first and second electrodes to emit light in a specific wavelength band. The plurality of light-emitting stacks may emit light of the same color or different colors. In addition, one or more light-emitting layers may be included in one light-emitting stack, and the plurality of light-emitting layers may emit light of the same color or different colors.
In this case, the light-emitting layer included in at least one of the plurality of light-emitting stacks may contain the organometallic compound represented by the Chemical Formula 1 according to the present disclosure as the dopants. Adjacent ones of the plurality of light-emitting stacks in the tandem structure may be connected to each other via the charge generation layer CGL including an N-type charge generation layer and a P-type charge generation layer.
As shown in
As shown in
Furthermore, an organic light-emitting diode according to an embodiment of the present disclosure may include a tandem structure in which four or more light-emitting stacks and three or more charge generating layers are disposed between the first electrode and the second electrode.
The organic light-emitting diode according to the present disclosure may be used as a light-emitting element of each of an organic light-emitting display device and a lighting device. In one implementation,
As shown in
Although not shown explicitly in
The driving thin-film transistor Td is connected to the switching thin film transistor, and includes a semiconductor layer 3100, a gate electrode 3300, a source electrode 3520, and a drain electrode 3540.
The semiconductor layer 3100 may be formed on the substrate 3010 and may be made of an oxide semiconductor material or polycrystalline silicon. When the semiconductor layer 3100 is made of an oxide semiconductor material, a light-shielding pattern (not shown) may be formed under the semiconductor layer 3100. The light-shielding pattern prevents light from being incident into the semiconductor layer 3100 to prevent the semiconductor layer 3100 from being deteriorated due to the light. Alternatively, the semiconductor layer 3100 may be made of polycrystalline silicon. In this case, both edges of the semiconductor layer 3100 may be doped with impurities.
The gate insulating layer 3200 made of an insulating material is formed over an entirety of a surface of the substrate 3010 and on the semiconductor layer 3100. The gate insulating layer 3200 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.
The gate electrode 3300 made of a conductive material such as a metal is formed on the gate insulating layer 3200 and corresponds to a center of the semiconductor layer 3100. The gate electrode 3300 is connected to the switching thin film transistor.
The interlayer insulating layer 3400 made of an insulating material is formed over the entirety of the surface of the substrate 3010 and on the gate electrode 3300. The interlayer insulating layer 3400 may be made of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acryl.
The interlayer insulating layer 3400 has first and second semiconductor layer contact holes 3420 and 3440 defined therein respectively exposing both opposing sides of the semiconductor layer 3100. The first and second semiconductor layer contact holes 3420 and 3440 are respectively positioned on both opposing sides of the gate electrode 3300 and are spaced apart from the gate electrode 3300.
The source electrode 3520 and the drain electrode 3540 made of a conductive material such as metal are formed on the interlayer insulating layer 3400. The source electrode 3520 and the drain electrode 3540 are positioned around the gate electrode 3300, and are spaced apart from each other, and respectively contact both opposing sides of the semiconductor layer 3100 via the first and second semiconductor layer contact holes 3420 and 3440, respectively. The source electrode 3520 is connected to a power line (not shown).
The semiconductor layer 3100, the gate electrode 3300, the source electrode 3520, and the drain electrode 3540 constitute the driving thin-film transistor Td. The driving thin-film transistor Td has a coplanar structure in which the gate electrode 3300, the source electrode 3520, and the drain electrode 3540 are positioned on top of the semiconductor layer 3100.
Alternatively, the driving thin-film transistor Td may have an inverted staggered structure in which the gate electrode is disposed under the semiconductor layer while the source electrode and the drain electrode are disposed above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. In one example, the switching thin-film transistor (not shown) may have substantially the same structure as that of the driving thin-film transistor (Td).
In one example, the organic light-emitting display device 3000 may include a color filter 3600 absorbing the light generated from the electroluminescent element (light-emitting diode) 4000. For example, the color filter 3600 may absorb red (R), green (G), blue (B), and white (W) light. In this case, red, green, and blue color filter patterns that absorb light may be formed separately in different pixel areas. Each of these color filter patterns may be disposed to overlap each organic layer 4300 of the organic light-emitting diode 4000 to emit light of a wavelength band corresponding to each color filter. Adopting the color filter 3600 may allow the organic light-emitting display device 3000 to realize full-color.
For example, when the organic light-emitting display device 3000 is of a bottom emission type, the color filter 3600 absorbing light may be positioned on a portion of the interlayer insulating layer 3400 corresponding to the organic light-emitting diode 4000. In an optional embodiment, when the organic light-emitting display device 3000 is of a top emission type, the color filter may be positioned on top of the organic light-emitting diode 4000, that is, on top of a second electrode 4200. For example, the color filter 3600 may be formed to have a thickness of 2 to 5 μm.
In one example, a planarization layer 3700 having a drain contact hole 3720 defined therein exposing the drain electrode 3540 of the driving thin-film transistor Td is formed to cover the driving thin-film transistor Td.
On the planarization layer 3700, each first electrode 4100 connected to the drain electrode 3540 of the driving thin-film transistor Td via the drain contact hole 3720 is formed individually in each pixel area.
The first electrode 4100 may act as a positive electrode (anode), and may be made of a conductive material having a relatively large work function value. For example, the first electrode 4100 may be made of a transparent conductive material such as ITO, IZO or ZnO.
In one example, when the organic light-emitting display device 3000 is of a top-emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 4100. For example, the reflective electrode or the reflective layer may be made of one of aluminum (Al), silver (Ag), nickel (Ni), and an aluminum-palladium-copper (APC) alloy.
A bank layer 3800 covering an edge of the first electrode 4100 is formed on the planarization layer 3700. The bank layer 3800 exposes a center of the first electrode 4100 corresponding to the pixel area.
An organic layer 4300 is formed on the first electrode 4100. If necessary, the organic light-emitting diode 4000 may have a tandem structure. Regarding the tandem structure, reference may be made to
The second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 has been formed. The second electrode 4200 is disposed over the entirety of the surface of the display area and is made of a conductive material having a relatively small work function value and may be used as a negative electrode (a cathode). For example, the second electrode 4200 may be made of one of aluminum (Al), magnesium (Mg), and an aluminum-magnesium alloy (Al—Mg).
The first electrode 4100, the organic layer 4300, and the second electrode 4200 constitute the organic light-emitting diode 4000.
An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating into the organic light-emitting diode 4000. Although not shown explicitly in
Hereinafter, Synthesis Example and Present Example of the present disclosure will be described. However, following Examples are only examples of the present disclosure. The present disclosure is not limited thereto.
SM_A (8.10 g, 30 mmol) was dissolved in tetrahydrofuran (200 ml), and then N-bromosuccinimide (5.34 g, 30 mmol) was slowly added thereto in a dropwise manner, followed by stirring thereof for 5 hours in a nitrogen environment. The solution was subjected to evaporation, and then, a residue was divided into a portion dissolved in dichloromethane and a portion dissolved in water. An organic phase was isolated therefrom, and was dried on sodium sulfate such that the solvent was evaporated therefrom. After the evaporation of the solvent, a residue was washed with ethanol to obtain 7.43 g (71%) of a target compound A-2.
A-2 (6.98 g, 20 mmol), 3-neopentyl-2-(tributylstannyl)pyridine (14.67 g, 40 mmol) and Pd(PPh3)4 (0.46 g, 0.4 mmol) were dissolved in xylene (180 ml) to produce a mixed solution which in turn was stirred under reflux in a nitrogen environment for 24 hours. A resulting crude mixture was filtered through celite and silica gel to obtain a solid which in turn was subjected to extraction using dichloromethane and water to obtain an organic layer. Then, the organic layer was subjected to evaporation. A resulting residue was purified by means of silica gel-based column chromatography using 30% dichloromethane in hexane to obtain 7.09 g (85%) of a target compound A-1.
A mixed solution in which A-1 (6.26 g, 15 mmol) and sodium ethoxide (4.07 g, 60 mmol) were dissolved in DMSO-d6 (150 ml) was refluxed for 30 hours. The solution was subjected to evaporation. A residue was divided into a portion dissolved in dichloromethane and a portion dissolved in water. An organic phase was isolated therefrom, and was dried on sodium sulfate such that the solvent was evaporated therefrom. After the evaporation of the solvent, a residue was purified by means of silica gel-based column chromatography using 50% hexane in dichloromethane to obtain 5.16 g (82%) of a target compound A.
A mixed solution in which SM_B (28.96 g, 120 mmol), methyltrioctylammonium chloride (4.85 g, 12 mmol) and K2CO3 (33.17 g, 240 mmol) were dissolved in N-methyl pyrrolidone (480 ml) was stirred at 180° C. overnight. The solution was subjected to evaporation. A residue was divided into a portion dissolved in dichloromethane and a portion dissolved in water. An organic phase was isolated therefrom, and was dried on sodium sulfate such that the solvent was evaporated therefrom. Thereafter, a crude mixture was dissolved in dichloromethane, and methanol and ultrapure water were added thereto to precipitate a solid to obtain 20.88 g (42%) of a target compound B-4.
A mixed solution in which B-4 (20.72 g, 50 mmol), phenol (5.65 g, 60 mmol) and K2CO3 (13.82 g, 100 mmol) were dissolved in N-methyl pyrrolidone (250 ml) was stirred at 150° C. overnight. The solution was subjected to evaporation. A residue was divided into a portion dissolved in dichloromethane and a portion dissolved in water. An organic phase was isolated therefrom, and was dried on sodium sulfate such that the solvent was evaporated therefrom. Thereafter, a crude mixture was dissolved in dichloromethane, and methanol and ultrapure water were added thereto to precipitate a solid to obtain 19.78 g (81%) of a target compound B-3.
100 ml tetrahydrofuran was added to a mixed solution in which B-3 (19.54 g, 40 mmol), and 1.5 M isopropyl MgCl LiCl were dissolved in tetrahydrofuran (200 ml). The solution was stirred for 1 hour in a nitrogen environment. 2-isoporpoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.28 g, 45 mmol) was added thereto, and then, the solution was further stirred for 3 hours. A crude mixture was divided into a portion dissolved in 5% aqueous HCl and a portion dissolved in toluene. An organic phase was isolated therefrom, and the solvent was evaporated therefrom. A residue was purified by means of silica gel-based column chromatography using toluene to obtain 14.99 g (70%) of a target compound B-2.
B-2 (13.39 g, 25 mmol), diisopropyl ethyl amine (3.87 g, 30 mmol) and aluminum trichloride (4.00 g, 30 mmol) were dissolved in toluene (180 ml), followed by stirring thereof under a nitrogen environment and at 80 degrees Celsius for 2 hours. A reaction product was cooled down to room temperature, and then, a temperature was lowered to 0 degrees Celsius. A residue was divided into a portion dissolved in toluene and a portion dissolved in water. An organic phase was isolated therefrom, and then was washed with aqueous sodium bicarbonate and brine and was dried on sodium sulfate such that the solvent was evaporated therefrom. A residue was purified by means of silica gel-based column chromatography using toluene to obtain 5.01 g (48%) of a target compound B-1.
A mixed solution in which B-1 (4.17 g, 10 mmol) and sodium ethoxide (2.71 g, 40 mmol) were dissolved in DMSO-d6 (120 ml) was refluxed for 30 hours. The solution was subjected to evaporation. A residue was divided into a portion dissolved in dichloromethane and a portion dissolved in water. An organic phase was isolated therefrom, and was dried on sodium sulfate such that the solvent was evaporated therefrom. After the evaporation of the solvent, a residue was purified by means of silica gel-based column chromatography using 50% hexane in dichloromethane to obtain 3.77 g (90%) of a target compound B.
A solution in which C (6.77 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 8.39 g (93%) of a target compound CC.
A solution in which D (7.89 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 8.93 g (90%) of a target compound DD.
A solution in which E (10.94 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 10.26 g (83%) of a target compound EE.
A solution in which F (6.89 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 8.48 g (93%) of a target compound FF.
A solution in which G (8.25 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 9.29 g (91%) of a target compound GG.
A solution in which H (11.30 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 10.75 g (85%) of a target compound HH.
A solution in which B-1 (16.69 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 27.14 g (80%) of a target compound II.
A solution in which B (16.77 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 25.20 g (74%) of a target compound JJ.
A solution in which A-1 (16.69 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 28.50 g (84%) of a target compound KK.
A solution in which A (16.77 g, 40 mmol) and IrCl3 (4.78 g, 16 mmol) were dissolved in ethoxyethanol (100 ml), and distilled water (30 ml) was stirred under reflux for 24 hours. Thereafter, a temperature was lowered to room temperature, and a resulting solid was separated via filtration under reduced pressure. The solid filtered through a filter was sufficiently washed with water and cold methanol and then filtered under reduced pressure. This process was repeated several times to obtain 27.58 g (81%) of a target compound LL.
A solution in which CC (6.77 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 8.46 g (95%) of a target compound CCC.
A solution in which DD (7.44 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 8.81 g (92%) of a target compound DDD.
A solution in which EE (9.27 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 10.15 g (89%) of a target compound EEE.
A solution in which FF (6.84 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 8.53 g (95%) of a target compound FFF.
A solution in which GG (7.66 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 9.20 g (94%) of a target compound GGG.
A solution in which HH (9.49 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 10.11 g (87%) of a target compound HHH.
A solution in which II (12.72 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 11.74 g (79%) of a target compound III.
A solution in which JJ (12.77 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 11.92 g (80%) of a target compound JJJ.
A solution in which KK (12.72 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 11.42 g (72%) of a target compound KKK.
A solution in which LL (12.77 g, 6 mmol) and silver trifluoromethanesulfonate (4.54 g, 18 mmol) were dissolved in dichloromethane (100 ml), and methanol (100 ml) was stirred overnight at room temperature. After completion of a reaction, a reaction solution was filtered with Celite to remove solid precipitates therefrom. A filtrate obtained through the filter was filtered under reduced pressure. This process was repeated several times to obtain 11.18 g (75%) of a target compound LLL.
A solution in which A-1 (2.09 g, 5 mmol) and CCC (4.45 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.59 g (76%) of a target iridium compound 273.
A solution in which A (2.10 g, 5 mmol) and FFF (4.49 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.76 g (79%) of a target iridium compound 393.
A solution in which A-1 (2.09 g, 5 mmol) and DDD (4.79 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.25 g (85%) of a target iridium compound 297.
A solution in which A (2.10 g, 5 mmol) and GGG (4.90 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.08 g (80%) of a target iridium compound 417.
A solution in which A-1 (2.09 g, 5 mmol) and EEE (5.70 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.61 g (80%) of a target iridium compound 321.
A solution in which A (2.10 g, 5 mmol) and HHH (5.81 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.81 g (82%) of a target iridium compound 441.
A solution in which B-1 (2.09 g, 5 mmol) and CCC (4.45 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.78 g (80%) of a target iridium compound 033.
A solution in which B (2.10 g, 5 mmol) and FFF (4.49 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.86 g (81%) of a target iridium compound 153.
A solution in which B-1 (2.09 g, 5 mmol) and DDD (4.79 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.00 g (80%) of a target iridium compound 057.
A solution in which B (2.10 g, 5 mmol) and GGG (4.90 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.44 g (87%) of a target iridium compound 177.
A solution in which B-1 (2.10 g, 5 mmol) and EEE (5.70 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.84 g (84%) of a target iridium compound 081.
A solution in which B (2.10 g, 5 mmol) and HHH (5.81 g, 6 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 5.04 g (86%) of a target iridium compound 201.
A solution in which C (1.02 g, 6 mmol) and III (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.70 g (62%) of a target iridium compound 632.
A solution in which F (1.03 g, 6 mmol) and JJJ (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.96 g (66%) of a target iridium compound 740.
A solution in which D (1.18 g, 6 mmol) and III (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.15 g (68%) of a target iridium compound 668.
A solution in which G (1.24 g, 6 mmol) and JJJ (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.89 g (63%) of a target iridium compound 776.
A solution in which E (1.64 g, 6 mmol) and III (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.89 g (60%) of a target iridium compound 704.
A solution in which H (1.69 g, 6 mmol) and JJJ (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.06 g (62%) of a target iridium compound 812.
A solution in which C (1.02 g, 6 mmol) and KKK (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.00 g (67%) of a target iridium compound 631.
A solution in which F (1.03 g, 6 mmol) and LLL (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.96 g (69%) of a target iridium compound 739.
A solution in which D (1.18 g, 6 mmol) and KKK (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.33 g (71%) of a target iridium compound 667.
A solution in which G (1.24 g, 6 mmol) and LLL (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.32 g (70%) of a target iridium compound 775.
A solution in which E (1.64 g, 6 mmol) and KKK (6.19 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 4.15 g (64%) of a target iridium compound 703.
A solution in which H (1.69 g, 6 mmol) and LLL (6.21 g, 5 mmol) were dissolved in 2-ethoxyethanol (100 ml) and DMF (100 ml) was stirred at 135° C. for 24 hours. After completion of a reaction, a temperature was lowered to room temperature, and an organic phase was isolated therefrom using dichloromethane and distilled water, and anhydrous magnesium sulfate was added thereto to remove water therefrom. A solution was obtained through filtration thereof, and was depressurized to obtain a residue. The residue was purified by means of silica gel-based column chromatography using 25% ethyl acetate in hexane to obtain 3.93 g (60%) of a target iridium compound 811.
A glass substrate having a thin film of ITO (indium tin oxide) having a thickness of 1,000 Å coated thereon was washed, followed by ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, or methanol. Then, the glass substrate was dried. Thus, an ITO transparent electrode was formed. HI-1 as a hole injection material was deposited on the ITO transparent electrode in a thermal vacuum deposition manner. Thus, a hole injection layer having a thickness of 60 nm was formed. Then, NPB as a hole transport material was deposited on the hole injection layer in a thermal vacuum deposition manner. Thus, a hole transport layer having a thickness of 80 nm was formed. Then, CBP as a host material of a light-emitting layer was deposited on the hole transport layer in a thermal vacuum deposition manner. The compound 273 as a dopant was doped into the host material at a doping concentration of 5%. Thus, the light-emitting layer of a thickness of 30 nm was formed. ET-1:Liq (1:1) (30 nm) as materials for an electron transport layer and an electron injection layer, respectively, were deposited on the light-emitting layer. Then, 100 nm thick aluminum was deposited thereon to form a negative electrode. In this way, an organic light-emitting diode was manufactured. The materials used in Present Example 1 are as follows.
HI-1 is NPNPB, and ET-1 is ZADN.
An organic light-emitting diode of each of Present Examples 2 to 24 was manufactured in the same manner as in Present Example 1, except that each of compounds as indicated in following Tables 1 and 2 was used instead of the compound 273 in Present Example 1.
An organic light-emitting diode of each of Comparative Examples 1 to 6 was manufactured in the same manner as in Present Example 1, except that each of following compounds Ref-1 to Ref-6 as compounds as indicated in the following Tables 1 and 2 was used instead of the compound 273 in Present Example 1:
The organic light-emitting diode as manufactured in each of Present Examples 1 to 24 and Comparative Examples 1 to 6 was connected to an external power source, and characteristics of the organic light-emitting diode were evaluated at room temperature using a current source and a photometer.
Specifically, operation voltage (V), maximum light-emission quantum efficiency (%), external quantum efficiency (EQE;%, relative value), and lifetime characteristics (LT95;%, relative value) were measured at a current density of 10 mA/cm2, and were calculated as relative values to those of Comparative Example 1 or 4, and the results are shown in following Tables 1 and 2.
LT95 lifetime refers to a time it takes for the display element to lose 5% of its initial brightness. LT95 is the customer specification to most difficult to meet. Whether or not image burn-in occurs on the display may be determined based on the LT95.
Each of the compounds of Present Examples of the present disclosure is different from each of Ref-1 to Ref-6 as the dopant compound of the light-emitting layer of each of Comparative Examples 1 to 6 of the present disclosure in that each of Ref-1 to Ref-6 has a structure in which a fused polycyclic structure containing a boron (B) element is not introduced thereto.
As may be identified from the results of Tables 1 and 2, the organic light-emitting diode of each of Present Examples 1 to 24 of the present disclosure in which the organometallic compound of the structure in which a fused polycyclic structure containing a boron (B) element is introduced thereto is used as a dopant in the light-emitting layer has lowered operation voltage, and improved maximum light-emission quantum efficiency, external quantum efficiency (EQE) and lifetime (LT95) compared to those in the organic light-emitting diode of each of Comparative Examples 1 to 6.
Although the embodiments of the present disclosure have been described in more detail with reference to the accompanying drawings, the present disclosure is not necessarily limited to these embodiments, and may be modified in a various manner within the scope of the technical spirit of the present disclosure. Accordingly, the embodiments as disclosed in the present disclosure are intended to describe rather than limit the technical idea of the present disclosure, and the scope of the technical idea of the present disclosure is not limited by these embodiments. Therefore, it should be understood that the embodiments described above are not restrictive but illustrative in all respects.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0012118 | Jan 2023 | KR | national |
