Patent Application
20230189642
The present application claims the benefit of Republic of Korea Patent Application No. 10-2021-0178383 filed in the Republic of Korea on Dec. 14, 2021, which is hereby incorporated by reference in their entirety.
The present disclosure relates to an emitting compound, and more specifically, to an emitting compound having low driving voltage, high emitting efficiency and lifespan and an organic light emitting device including the same.
As requests for a flat panel display device having a small occupied area have been increased, an organic light emitting display device including an organic light emitting diode (OLED) has been the subject of recent research and development.
The OLED emits light by injecting electrons from a cathode as an electron injection electrode and holes from an anode as a hole injection electrode into an emitting material layer (EML), combining the electrons with the holes, generating an exciton, and transforming the exciton from an excited state to a ground state. A flexible substrate, for example, a plastic substrate, can be used as a base substrate where elements are formed. In addition, the organic light emitting display device can be operated at a voltage (e.g., 10V or below) lower than a voltage required to operate other display devices. Moreover, the organic light emitting display device has advantages in the power consumption and the color sense.
For example, the organic light emitting display device may include a red pixel region, a green pixel region and a blue pixel region, and the OLED may be formed in each of the red, green and blue pixel regions.
However, the OLED in the blue pixel does not provide sufficient emitting efficiency and lifespan such that the organic light emitting display device has a limitation in the emitting efficiency and the lifespan.
The present disclosure is directed to an emitting compound and an organic light emitting device including the emitting compound that substantially obviate one or more of the problems associated with the limitations and disadvantages of the related conventional art.
Additional features and advantages of the present disclosure are set forth in the description which follows, and will be apparent from the description, or evident by practice of the present disclosure. The objectives and other advantages of the present disclosure are realized and attained by the features described herein as well as in the appended drawings.
To achieve these and other advantages in accordance with the purpose of the embodiments of the present disclosure, as described herein, an aspect of the present disclosure is an emitting compound represented by Formula 1:
wherein each of a A1 ring, a A2 ring and a A3 ring is independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C30 heteroaromatic ring, wherein X is one of B, P═O and P═S, and each of R1, R2 and R3 is independently selected from the group consisting of deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, wherein each of a1 and a2 is independently an integer of 0 to 4, and a3 is an integer of 0 to 2, wherein Y1 is one of N, CR4 or SiR4, and Y2 is one of NRs, C(R5)2, O, S, Se or Si(R5)2, and wherein each of R4 and R5 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 alicyclic group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group.
Another aspect of the present disclosure is an organic light emitting device comprising a substrate; and an organic light emitting diode positioned on the substrate and including a first electrode; a second electrode facing the first electrode; and a first emitting material layer including a first compound and positioned between the first and second electrodes, wherein the first compound is the above emitting compound.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to further explain the present disclosure as claimed.
The accompanying drawings, which are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure.
Reference will now be made in detail to some of the examples and preferred embodiments, which are illustrated in the accompanying drawings.
The present disclosure provides an OLED and an organic light emitting device. For example, the organic light emitting device may be an organic light emitting display device or an organic light emitting lighting device. The explanation below is focused on the organic light emitting display device including the OLED.
As illustrated in
The switching thin film transistor Ts is connected to the gate line GL and the data line DL, and the driving thin film transistor Td and the storage capacitor Cst are connected between the switching thin film transistor Ts and the power line PL. The OLED D is connected to the driving thin film transistor Td. When the switching thin film transistor Ts is turned on by the gate signal applied through the gate line GL, the data signal applied through the data line DL is applied a gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.
The driving thin film transistor Td is turned on by the data signal applied into the gate electrode so that a current proportional to the data signal is supplied from the power line PL to the OLED D through the driving thin film transistor Td. The OLED D emits light having a luminance proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal so that the voltage of the gate electrode in the driving thin film transistor Td is kept constant during one frame. Therefore, the organic light emitting display device can display a desired image.
As illustrated in
The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate or a polycarbonate (PC) substrate.
A buffer layer 120 is formed on the substrate, and the TFT Tr is formed on the buffer layer 120. The buffer layer 120 may be omitted.
A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polycrystalline silicon.
When the semiconductor layer 122 includes the oxide semiconductor material, a light-shielding pattern (not shown) may be formed under the semiconductor layer 122. The light to the semiconductor layer 122 is shielded or blocked by the light-shielding pattern such that thermal degradation of the semiconductor layer 122 can be prevented. On the other hand, when the semiconductor layer 122 includes polycrystalline silicon, impurities may be doped into both sides of the semiconductor layer 122.
A gate insulating layer 124 is formed on the semiconductor layer 122. The gate insulating layer 124 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.
A gate electrode 130, which is formed of a conductive material, e.g., metal, is formed on the gate insulating layer 124 to correspond to a center of the semiconductor layer 122.
In
An interlayer insulating layer 132, which is formed of an insulating material, is formed on the gate electrode 130. The interlayer insulating layer 132 may be formed of an inorganic insulating material, e.g., silicon oxide or silicon nitride, or an organic insulating material, e.g., benzocyclobutene or photo-acryl.
The interlayer insulating layer 132 includes first and second contact holes 134 and 136 exposing both sides of the semiconductor layer 122. The first and second contact holes 134 and 136 are positioned at both sides of the gate electrode 130 to be spaced apart from the gate electrode 130.
The first and second contact holes 134 and 136 are formed through the gate insulating layer 124. Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate electrode 130, the first and second contact holes 134 and 136 is formed only through the interlayer insulating layer 132.
A source electrode 140 and a drain electrode 142, which are formed of a conductive material, e.g., metal, are formed on the interlayer insulating layer 132.
The source electrode 140 and the drain electrode 142 are spaced apart from each other with respect to the gate electrode 130 and respectively contact both sides of the semiconductor layer 122 through the first and second contact holes 134 and 136.
The semiconductor layer 122, the gate electrode 130, the source electrode 140 and the drain electrode 142 constitute the TFT Tr. The TFT Tr serves as a driving element. Namely, the TFT Tr may correspond to the driving TFT Td (of
In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 are positioned over the semiconductor layer 122. Namely, the TFT Tr has a coplanar structure.
Alternatively, in the TFT Tr, the gate electrode may be positioned under the semiconductor layer, and the source and drain electrodes may be positioned over the semiconductor layer such that the TFT Tr may have an inverted staggered structure. In this instance, the semiconductor layer may include amorphous silicon.
Although not shown, the gate line and the data line cross each other to define the pixel, and the switching TFT is formed to be connected to the gate and data lines. The switching TFT is connected to the TFT Tr as the driving element.
In addition, the power line, which may be formed to be parallel to and spaced apart from one of the gate and data lines, and the storage capacitor for maintaining the voltage of the gate electrode of the TFT Tr in one frame may be further formed.
A passivation layer (or a planarization layer) 150, which includes a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr, is formed to cover the TFT Tr.
A first electrode 160, which is connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152, is separately formed in each pixel and on the passivation layer 150. The first electrode 160 may be an anode and may be formed of a conductive material, e.g., a transparent conductive oxide (TCO), having a relatively high work function. For example, the first electrode 160 may be formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO) or aluminum-zinc-oxide (A1:ZnO, AZO).
When the organic light emitting display device 100 is operated in a bottom-emission type, the first electrode 160 may have a single-layered structure of the transparent conductive material layer. When the organic light emitting display device 100 is operated in a top-emission type, the first electrode 160 may further include a reflection electrode or a reflection layer. For example, the reflection electrode or the reflection layer may be formed of silver (Ag) or aluminum-palladium-copper (APC) alloy. In the top-emission type organic light emitting display device 100, the first electrode 160 may have a triple-layered structure of ITO/Ag/ITO or ITO/APC/ITO.
A bank layer 166 is formed on the passivation layer 150 to cover an edge of the first electrode 160. Namely, the bank layer 166 is positioned at a boundary of the pixel and exposes a center of the first electrode 160 in the pixel.
An organic emitting layer 162 is formed on the first electrode 160. The organic emitting layer 162 may have a single-layered structure of an emitting material layer including an emitting material. To increase an emitting efficiency of the OLED D and/or the organic light emitting display device 100, the organic emitting layer 162 may have a multi-layered structure.
The organic emitting layer 162 is separated in each of the red, green and blue pixels. As illustrated below, the organic emitting layer 162 in the blue pixel includes an emitting compound of Formula 1 such that the emitting efficiency and the lifespan of the OLED D in the blue pixel are improved.
A second electrode 164 is formed over the substrate 110 where the organic emitting layer 162 is formed. The second electrode 164 covers an entire surface of the display area and may be formed of a conductive material having a relatively low work function to serve as a cathode. For example, the second electrode 164 may be formed of aluminum (A1), magnesium (Mg), calcium (Ca), silver (Ag) or their alloy or combination. In the top-emission type organic light emitting display device 100, the second electrode 164 may have a thin profile (small thickness) to provide a light transmittance property (or a semi-transmittance property).
The first electrode 160, the organic emitting layer 162 and the second electrode 164 constitute the OLED D.
An encapsulation film 170 is formed on the second electrode 164 to prevent penetration of moisture into the OLED D. The encapsulation film 170 includes a first inorganic insulating layer 172, an organic insulating layer 174 and a second inorganic insulating layer 176 sequentially stacked, but it is not limited thereto. The encapsulation film 170 may be omitted.
The organic light emitting display device 100 may further include a polarization plate (not shown) for reducing an ambient light reflection. For example, the polarization plate may be a circular polarization plate. In the bottom-emission type organic light emitting display device 100, the polarization plate may be disposed under the substrate 110. In the top-emission type organic light emitting display device 100, the polarization plate may be disposed on or over the encapsulation film 170.
In addition, in the top-emission type organic light emitting display device 100, a cover window (not shown) may be attached to the encapsulation film 170 or the polarization plate. In this instance, the substrate 110 and the cover window have a flexible property such that a flexible organic light emitting display device may be provided.
As illustrated in
One of the first and second electrodes 160 and 164 is an anode, and the other one of the first and second electrodes 160 and 164 is cathode. In addition, one of the first and second electrodes 160 and 164 may be a transparent (or a semi-transparent) electrode, and the other one of the first and second electrodes 160 and 164 may be a reflection electrode.
The organic emitting layer 162 may further include an electron blocking layer (EBL) 230 between the first electrode 160 and the EML 240 and a hole blocking layer (HBL) 250 between the EML 240 and the second electrode 164.
In addition, the organic emitting layer 162 may further include a hole transporting layer (HTL) 220 between the first electrode 160 and the EBL 230.
Moreover, the organic emitting layer 162 may further include a hole injection layer (HIL) 210 between the first electrode 160 and the HTL 220 and an electron injection layer (EIL) 260 between the second electrode 164 and the HBL 250.
The EML 240 includes an emitting compound 242 as a first compound. The emitting compound is a polycyclic aromatic compound and is represented by Formula 1.
In Formula 1, each of an A1 ring, a A2 ring and a A3 ring is independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aromatic ring (or aromatic fused-ring) and a substituted or unsubstituted C5 to C30 heteroaromatic ring (or heteroaromatic fused-ring).
X is one of B, P═O and P═S. Each of R1, R2 and R3 is independently selected from the group consisting of deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group. In addition, each of a1 and a2 is independently an integer of 0 to 4, and a3 is an integer of 0 to 2.
Y1 is one of N, CR4 and SiR4, and Y2 is one of NRs, C(R5)2, O, S, Se and Si(R5)2. each of R4 and R5 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 alicyclic group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group.
R4 may be connected to the A1 ring or the A3 ring to form an aromatic ring or a heteroaromatic ring, and R5 may be connected to the A2 ring or the A3 ring to form an aromatic ring or a heteroaromatic ring. In addition, in each of the A1 ring, the A2 ring, and the A3 ring, the substituents may be connected to each other to form an aromatic ring or a heteroaromatic ring.
In the present disclosure, without specific definition, a substituent of alkyl group, cycloalkyl group, aryl group, heteroaryl group, cycloalkyl ring, aromatic ring and heteroaromatic ring may be at least one of deuterium, tritium, a C1 to C10 alkyl group and a C6 to C30 aryl group.
In the present disclosure, without specific definition, the C6 to C30 aryl group (or C6 to C30 arylene group) may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentanenyl, indenyl, indenoindenyl, heptalenyl, biphenylenyl, indacenyl, phenanthrenyl, benzophenanthrenyl, dibenzophenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylenyl, chrysenyl, tetraphenyl, tetrasenyl, picenyl, pentaphenyl, pentacenyl, fluorenyl, indenofluorenyl and spiro-fluorenyl.
In the present disclosure, without specific definition, the C5 to C30 heteroaryl group may be selected from the group consisting of pyrrolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, quinozolinyl, quinolinyl, purinyl, phthalazinyl, quinoxalinyl, benzoquinolinyl, benzoisoquinolinyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenanthrolinyl, perimidinyl, phenanthridinyl, pteridinyl, cinnolinyl, naphtharidinyl, furanyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxynyl, benzofuranyl, dibenzofuranyl, thiopyranyl, xanthenyl, chromanyl, isochromanyl, thioazinyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, difuropyrazinyl, benzofurodibenzofuranyl, benzothienobenzothiophenyl, benzothienodibenzothiophenyl, benzothienobenzofuranyl, and benzothienodibenzofuranyl.
In the present disclosure, without specific definition, the C6 to C30 aromatic ring may be selected from the group consisting of benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, chrysene ring, pyrene ring, fluoranthene ring, fluorene ring and spirofluorene ring.
In the present disclosure, without specific definition, the C5 to C30 heteroaromatic ring may be selected from the group consisting of pyridine ring, pyrimidine ring, purine ring, furan ring, imidazole ring, thiophene ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring and triazine ring.
In the present disclosure, without specific definition, the C1 to C10 alkyl group may be selected from the group consisting of methyl, ethyl, isopropyl, sec-butyl, iso-butyl and tert-butyl.
In the present disclosure, without specific definition, the C3 to C10 cycloalkyl group may be selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and adamantyl.
In the present disclosure, without specific definition, the C6 to C30 arylamine group may be selected from the group consisting of phenylamine and diphenylamine.
For example, X may be B, and each of R1, R2 and R3 may be a C6 to C30 aryl group, e.g., phenyl. Y1 may be N, and Y2 may be one of NRs, C(R5)2, O, and Si(R5)2.
In Formula 1, a linking (connecting, combining or joining) position of an anthracene moiety may be specified. Namely, the first compound 242 may be represented by Formula 2-1 or Formula 2-2.
In Formula 2-1, the definitions of the A1 ring, the A2 ring, the A3 ring, X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1.
In Formula 2-2, the definitions of the A1 ring, the A2 ring, the A3 ring, X, R1, R2, R3, Y1, Y2, a1 and a2 are same as those in Formula 1.
In each of Formulas 1, 2-1 and 2-2, Y1 may be N, and Y2 may be NR5. For example, Formula 2-1 and Formula 2-2 may be represented by Formula 2-3 and Formula 2-4, respectively.
In Formula 2-3, the definitions of the A1 ring, the A2 ring, the A3 ring, X, R1, R2, R3, R5, a1, a2 and a3 are same as those in Formula 1.
In Formula 2-4, the definitions of the A1 ring, the A2 ring, the A3 ring, X, R1, R2, R3, R5, a1 and a2 are same as those in Formula 1.
In each of Formulas 1, 2-1, 2-2, 2-3 and 2-4, A1 may be a substituted or unsubstituted benzothiophene ring or a substituted or unsubstituted benzofuran ring. For example, Formula 1 may be represented by Formula 3-1.
In Formula 3-1, Y3 is O or S. Each of R11, R12, R13 and R14 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R11, R12, R13 and R14 are connected to each other to form an aromatic ring or a heteroaromatic ring. The definitions of the A2 ring, the A3 ring, X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1.
For example, Y3 may be S, one of R11, R12, R13 and R14 may be a C1 to C10 alkyl group, e.g., tert-butyl, and the rest of R1, R12, R13 and R14 may be hydrogen. In one embodiment of the present disclosure, R13 may be a C1 to C10 alkyl group, e.g., tert-butyl, and R11, R12 and R14 may be hydrogen.
In each of Formulas 1, 2-1, 2-2, 2-3, 2-4 and 3-1, the A3 ring may be a substituted or unsubstituted benzene ring. For example, Formula 3-1 may be represented by Formula 3-2.
In Formula 3-2, each of R31, R32 and R33 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R31, R32 and R33 are connected to each other to form an aromatic ring or a heteroaromatic ring.
In Formula 3-2, the definitions of the A2 ring, X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1, and the definitions of Y3, R31, R32 and R33 are same as those in Formula 3-1.
For example, one of R31, R32 and R33 may be a C1 to C10 alkyl group, e.g., methyl or tert-butyl, and the rest of R31, R32 and R33 may be hydrogen.
In each of Formulas 1, 2-1, 2-2, 2-3, 2-4 and 3-1, the A2 ring may be a substituted or unsubstituted benzene ring. For example, Formula 3-1 may be represented by Formula 3-3.
In Formula 3-3, each of R15, R16, R17 and R18 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R15, R16, R17 and R18 are connected to each other to form an aromatic ring or a heteroaromatic ring.
The definitions of the A3 ring, X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1, and the definitions of Y3, R11, R12, R13 and R14 are same as those in Formula 3-1.
For example, one of R15, R16, R17 and R18 may be a C1 to C10 alkyl group, e.g., tert-butyl, or a C6 to C30 arylamine group, e.g., diphenylamine, and the rest of R15, R16, R17 and R18 may be hydrogen. Alternatively, two of R15, R16, R17 and R18 may be connected to each other to form a hetero-fused ring, e.g., acridan, with the benzene ring.
In each of Formulas 1, 2-1, 2-2, 2-3, 2-4 and 3-3, the A3 ring may be a substituted or unsubstituted benzene ring. For example, Formula 3-3 may be represented by Formula 3-4.
In Formula 3-4, each of R31, R32 and R33 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R31, R32 and R33 are connected to each other to form an aromatic ring or a heteroaromatic ring.
In Formula 3-4, the definitions of X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1, the definitions of Y3, R11, R12, R13 and R14 are same as those in Formula 3-1, and the definitions of R15, R16, R17 and R18 are same as those in Formula 3-3.
For example, one of R31, R32 and R33 may be a C1 to C10 alkyl group, e.g., methyl or tert-butyl, and the rest of R31, R32 and R33 may be hydrogen.
In each of Formulas 1, 2-1, 2-2, 2-3 and 2-4, each of the A1 ring and the A2 ring may be a substituted or unsubstituted benzene ring. For example, Formula 1 may be represented by Formula 3-5.
In Formula 3-5, each of R21, R22, R23 and R24 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R21, R22, R23 and R24 are connected to each other to form an aromatic ring or a heteroaromatic ring.
Each of R25, R26, R27 and R28 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R25, R26, R27 and R28 are connected to each other to form an aromatic ring or a heteroaromatic ring.
The definitions of the A3 ring, X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1.
For example, one of R21, R22, R23 and R24 may be a C1 to C10 alkyl group, e.g., tert-butyl, or a C6 to C30 arylamine group, e.g., diphenylamine, and the rest of R21, R22, R23 and R24 may be hydrogen. One of R25, R26, R27 and R28 may be a C1 to C10 alkyl group, e.g., tert-butyl, or a C6 to C30 arylamine group, e.g., diphenylamine, and the rest of R25, R26, R27 and R28 may be hydrogen.
In each of Formulas 1, 2-1, 2-2, 2-3, 2-4 and 3-5, the A3 ring may be a substituted or unsubstituted benzene ring. For example, Formula 3-5 may be represented by Formula 3-6.
In Formula 3-6, each of R31, R32 and R33 is independently selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group, or adjacent two of R31, R32 and R33 are connected to each other to form an aromatic ring or a heteroaromatic ring.
In Formula 3-6, the definitions of X, R1, R2, R3, Y1, Y2, a1, a2 and a3 are same as those in Formula 1, the definitions of R21, R22, R23, R24, R25, R26, R27 and R28 are same as those in Formula 3-5.
For example, one of R31, R32 and R33 may be a C1 to C10 alkyl group, e.g., methyl or tert-butyl, and the rest of R31, R32 and R33 may be hydrogen.
For example, the first compound 242 represented by Formula 1 may be one of the compounds in Formula 4.
The emitting compound in Formula 1 provides blue emission and is used for the EML 240 in the OLED D. As a result, the OLED D and the organic light emitting display device 100 have advantages in at least one of the driving voltage, the emitting efficiency and the lifespan.
1. Synthesis of Compound 1-1
(1) Compound I1-1c
In the 500 mL reactor, the compound I1-1a 13.8 g (49 mmol), the compound I1-1b 29.6 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred/refluxed for 5 hours. After completion of the reaction, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 32.8 g of the compound I1-1c. (Yield 79%)
(2) Compound 1-1
In the 500 mL reactor, the compound I1-1c 106 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.8 g of the compound 1-1. (Yield 18%)
2. Synthesis of Compound 1-3
(1) compound I1-3c
In the 500 mL reactor, the compound I1-3a 19.7 g (49 mmol), the compound I1-3b 29.6 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred/refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 32.2 g of the compound I1-3c. (Yield 68%)
(2) Compound 1-3
In the 500 mL reactor, the compound I1-3c 12.1 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.5 g of the compound 1-3. (Yield 21%)
3. Synthesis of Compound 1-4
(1) Compound I1-4c
In the 500 mL reactor, the compound I1-4a 19.2 g (49 mmol), the compound I1-4b 29.6 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred/refluxed for 5 hours. After completion of the reaction, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 39.0 g of the compound I1-4c. (Yield 83%)
(2) Compound 1-4
In the 500 mL reactor, the compound I1-4c 12.0 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.8 g of the compound 1-4. (Yield 24%)
4. Synthesis of Compound 1-8
(1) Compound I1-8c
In the 500 mL reactor, the compound I1-8a 23.4 g (49 mmol), the compound I1-8b 33.3 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred/refluxed for 5 hours. After completion of the reaction, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 43.9 g of the compound I1-8c. (Yield 80%)
(2) Compound 1-8
In the 500 mL reactor, the compound I1-8c 14.0 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.6 g of the compound 1-8. (Yield 19%)
5. Synthesis of Compound 1-13
(1) Compound I1-13c
In the 500 mL reactor, the compound I1-13a 23.4 g (49 mmol), the compound I1-13b 28.2 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred/refluxed for 5 hours. After completion of the reaction, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 36.8 g of the compound I1-13c. (Yield 74%)
(2) Compound 1-13
In the 500 mL reactor, the compound I1-13c 12.7 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.2 g of the compound 1-13. (Yield 18%)
6. Synthesis of Compound 1-15
(1) Compound I1-15c
In the 500 mL reactor, the compound I1-15a 23.4 g (49 mmol), the compound I1-15b 33.9 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 41.7 g of the compound I1-15c. (Yield 75%)
(2) Compound 1-15
In the 500 mL reactor, the compound I1-15c 14.2 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.8 g of the compound 1-15. (Yield 20%)
7. Synthesis of Compound 1-24
(1) Compound I1-24c
In the 500 mL reactor, the compound I1-24a 21.2 g (49 mmol), the compound I1-24b 36.0 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred under reflux for 5 hours. After completion of the reaction, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 39.3 g of the compound I1-24c. (Yield 71%)
(2) Compound 1-24
In the 500 mL reactor, the compound I1-24c 14.1 g (12.5 mmol) and tert-butylbenzene 60 mL were added. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.1 g of the compound 1-24. (Yield 15%)
8. Synthesis of Compound 1-27
(1) Compound I1-27c
In the 500 mL reactor, the compound I1-27a 21.9 g (49 mmol), the compound I1-27b 36.0 g (49 mmol), palladium acetate 0.23 g (1 mmol), sodium tert-butoxide 9.5 g (98 mmol), tri-tert-butylphosphine 0.4 g (2 mmol) and 300 mL of toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 43.76 g of the compound I1-27c. (Yield 78%)
(2) Compound 1-27
In the 500 mL reactor, the compound I1-27c 14.3 g (12.5 mmol) and tert-butylbenzene 60 mL were added to. 45 mL (37.5 mmol) of n-butyllithium was dropwisely added at −78° C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. Then, nitrogen was blown at 60° C. to remove heptane. Boron tribromide 6.3 g (25 mmol) was dropwisely added at −78° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was dropwisely added at 0° C. After dropwise addition, the mixture was stirred at 120° C. for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 2.4 g of the compound 1-27. (Yield 17%)
In the EML 240, the first compound 242 acts as a dopant (emitter) to emit the blue light.
In addition, the EML 240 may further include a second compound 244 as a host. In this instance, in the EML 240, the first compound 242 may have a weight % of about 0.1 weight % to 30 weight %, preferably about 0.1 weight % to 10 weight %, and more preferably about 1 weight % to 5 weight %. The EML 240 may have a thickness of about 10 to 500 Å, preferably about 50 to 400 Å, and more preferably about 100 to 300 Å.
The second compound 244 as the host may be an anthracene derivative. For example, the second compound 244 may be represented by Formula 5.
In Formula 5, each of Ar1 and Ar2 is independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group. L is a single bond or a substituted or unsubstituted C6 to C30 arylene group. In this instance, hydrogens in the anthracene derivative are not deuterated or partially or wholly deuterated. Namely, none, a part or all of the hydrogens in the anthracene derivative is substituted by deuterium.
In Formula 5, each of Ar1 and Ar2 may be selected from the group consisting of phenyl, naphthyl, dibenzofuranyl and fused dibenzofuranyl, and L may be the single bond or phenylene.
For example, Ar1 may be selected from the group consisting of naphthyl, dibenzofuranyl, phenyl-dibenzofuranyl and fused dibenzofuranyl, and Ar2 may be selected from the group consisting of phenyl and naphthyl. In an embodiment, Ar1 and Ar2 may be naphthyl, and L may be the single bond or phenylene.
In Formula 5, the anthracene core may be partially or wholly deuterated, or each of Ar1, Ar2, L may be partially or wholly deuterated. Alternatively, each of the anthracene core, Ar1, Ar2, L may be partially or wholly deuterated.
The second compound 244 in Formula 5 may be one of compounds in Formula 6. In the compounds H5 to H8, “D” denotes deuterium atom, and “x” in “Dx” denotes a number of deuterium atoms.
The HIL 210 may include at least one compound selected from the group consisting of 4,4′,4″-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4′,4″-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4′,4″-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4′,4″-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine(CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N′-diphenyl-N,N′-bis(1-naphthyl)-1,1′-biphenyl-4,4″-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile(dipyrazino[2,3-f:2′ 3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiphene)polystyrene sulfonate (PEDOT/PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. Alternatively, the HIL 210 may include a compound in Formula 13 below as a host and a compound in Formula 14 below as a dopant.
The HTL 220 may include at least one compound selected from the group consisting of N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine (TPD), NPB (or NPD), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)-benzidine] (poly-TPD), (poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine. Alternatively, the HTL 220 may include a compound of Formula 13 below.
The EBL 230, which is disposed between the HTL 220 and the EML 240, is formed to prevent the electron toward the HTL 220. The EBL 230 includes the electron blocking material of the amine derivative. The electron blocking material is represented by Formula 7.
In Formula 7, L is a C6 to C30 arylene group, and a is 0 or 1. Each of R1 and R2 is independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C5 to C30 heteroaryl group.
For example, L may be phenylene, and each of R1 and R2 may be selected from the group consisting of biphenyl, dimethyl substituted fluorenyl, carbazolyl, phenylcarbazolyl, carbazolylphenyl, dibenzothiophenyl and dibenzofuranyl.
Namely, the electron blocking material may be an amine derivative substituted by spirofluorene (e.g., “spirofluorene-substituted amine derivative”).
The electron blocking material of Formula 7 may be one of the followings of Formula 8:
The HBL 250, which is disposed between the EML 240 and EIL 260, is formed to prevent the hole toward the EIL 260. The HBL 250 includes the hole blocking material of the azine derivative. The azine derivative as the hole blocking material is represented by Formula 9.
In Formula 9, each of Y1 to Y5 is independently CR1 or N, and one to three of Y1 to Y5 is N. R1 is independently C6-C30 aryl group. L is C6-C30 arylene group, and R2 is C6-C30 aryl group or C5-C30 heteroaryl group, wherein the C6-C30 aryl group is optionally substituted with another C6-C30 aryl group or C5-C30 hetero aryl group or forms a spiro structure with a C10-C30 fused aryl ring or a C10-C30 fused hetero aryl ring, wherein the another C6-C30 aryl is optionally further substituted with other C6-C30 or C5-C30 hetero aryl or forms a spiro structure with a C10-C30 fused aryl ring. R3 is hydrogen, or adjacent two of R3 form a fused ring. “a” is 0 or 1, “b” is 1 or 2, and “c” is an integer of 0 to 4.
The hole blocking material of Formula 9 may be one of the followings of Formula 10.
Alternatively, the HBL 250 may include the benzimidazole derivative as the hole blocking material. For example, the benzimidazole derivative as the hole blocking material is represented by Formula 11-1.
In Formula 11-1, Ar is a substituted or unsubstituted C10-C30 arylene group, and R1 is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C5-C30 heteroaryl group. Ar2 is represented by one of Formulas 11-2, 11-3 and 11-4.
In Formulas 11-2 to 11-4, each of R2 and R3 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group and a substituted or unsubstituted C6 to C30 aryl group.
For example, Ar may be naphthylene or anthracenylene, R1 may be a C1 to C20 alkyl group, e.g., methyl, and each of R2 and R3 may be methyl, ethyl or phenyl.
The hole blocking material of Formula 11-1 may be one of the followings of Formula 12.
The HBL 250 may include at least one of the hole blocking material in Formula 9 and the hole blocking material in Formula 11-1.
In this instance, a thickness of EML 240 may be greater than each of that of the EBL 230 and the HBL 250 and may be smaller than that of the HTL 220. For example, the EML 240 may have a thickness of about 150 to 250 Å, each of the EBL 230 and the HBL 250 may have a thickness of about 50 to 150 Å, and the HTL 220 may have a thickness of about 900 to 1100 Å. The EBL 230 and the HBL 250 may have the same thickness.
The HBL 250 may include the compound in Formula 9 and the compound in Formula 11-1. For example, in the HBL 250, the compound in Formula 9 and the compound in Formula 11-1 may have the same weight %.
The hole blocking material in Formula 9 and/or Formula 11-1 has excellent hole blocking property and excellent electron transporting property. Accordingly, an electron transporting layer may be presented, and the HBL 250 may directly contact the EIL 260 or the second electrode 164.
The EIL 260 may include at least one of an alkali metal, such as Li, an alkali halide compound, such as LiF, CsF, NaF, or BaF2, and an organo-metallic compound, such as Liq, lithium benzoate, or sodium stearate, but it is not limited thereto. Alternatively, the EIL 260 may include a compound of Formula 15 as a host and an alkali metal as a dopant.
In the OLED D, the EML 240 includes the emitting compound 242 in Formula 1 such that the lifespan of the OLED D and the organic light emitting display device 100 is significantly improved. [Organic light emitting diode]
The anode (ITO), the HIL (Formula 13 (97 wt %) and Formula 14 (3 wt %), 100 Å), the HTL (Formula 13, 1000 Å), the EBL (the compound EBL-11 in Formula 8, 100 Å), the EML (the compound H-1 in Formula 6 (host, 98 wt %) and dopant (2 wt %), 200 Å), the HBL (the compound E1 in Formula 10, 100 Å), the EIL (Formula 15 (98 wt %) and Li (2 wt %), 200 Å) and the cathode (A1, 500 Å) was sequentially deposited. An encapsulation film is formed by using an UV curable epoxy and a moisture getter to form the OLED.
(1) Comparative Examples 1 to 3 (Ref1 to Ref3)
The compound Dopant-1, the compound Dopant-2 and the compound Dopant-3 in Formula 16 are respectively used as the dopant to form the EML.
(2) Examples 1 to 8 (Ex1 to Ex8)
The compounds 1-1, 1-3, 1-4, 1-8, 1-13, 1-15, 1-24 and 1-27 in Formula 4 are respectively used as the dopant to form the EML.
The properties, i.e., the driving voltage (V), the external quantum efficiency (EQE), the color coordinate (CIE) and the lifespan (T95), of the OLEDs manufactured in Comparative Examples 1 to 3 and Examples 1 to 8 are measured and listed in Table 1. The properties of the OLED were measured at the room temperature using a current source (KEITHLEY) and a photometer (PR 650). The driving voltage, the external quantum efficiency, and the color coordinate were measured under the condition of a current density of 10 mA/cm2, and the lifespan T95 (the time to reach 95% of the lifespan) was measured at 40° C. under the 22.5 mA/cm2 condition.
As shown in Table 1, in comparison to the OLED of Ref1 to Ref3, the OLED in Ex1 to Ex8 using the emitting compound of the present disclosure as the dopant has advantages in at least one of the driving voltage, the emitting efficiency and the lifespan.
Namely, when the emitting compound of the present disclosure, in which an anthracene moiety is directly connected to Y1 constituting a polyaromatic ring structure, is included in the EML, the driving voltage of the OLED is decreased, and the emitting efficiency and the lifespan of the OLED are increased.
In addition, in the OLED of Ex4 to Ex8 including the emitting compound, e.g., the compound 1-8, the compound 1-13, the compound 1-15, the compound 1-24 or the compound 1-27, in which a linking position of the anthracene moiety is specified as Formula 2-1, the driving voltage of the OLED is further decreased, and the emitting efficiency and the lifespan of the OLED are further increased.
Moreover, in the OLED of Ex5 to Ex8 including the emitting compound, e.g., the compound 1-13, the compound 1-15, the compound 1-24 or the compound 1-27, which includes a benzothiophene ring as Formula 3-1, the driving voltage of the OLED is further decreased, and the emitting efficiency and the lifespan of the OLED are further increased.
As shown in
One of the first and second electrodes 160 and 164 is an anode, and the other one of the first and second electrodes 160 and 164 is cathode. In addition, one of the first and second electrodes 160 and 164 may be a transparent (or a semi-transparent) electrode, and the other one of the first and second electrodes 160 and 164 may be a reflection electrode.
The CGL 350 is positioned between the first and second emitting parts 310 and 330, and the first emitting part 310, the CGL 350 and the second emitting part 330 are sequentially stacked on the first electrode 160. Namely, the first emitting part 310 is positioned between the first electrode 160 and the CGL 350, and the second emitting part 330 is positioned between the second electrode 164 and the CGL 350.
The first emitting part 310 includes a first EML 320. In addition, the first emitting part 310 may further include a first EBL 316 between the first electrode 160 and the first EML 320 and a first HBL 318 between the first EML 320 and the CGL 350.
In addition, the first emitting part 310 may further include a first HTL 314 between the first electrode 160 and the first EBL 316 and an HIL 312 between the first electrode 160 and the first HTL 314.
The first EML 320 includes the emitting compound in Formula 1 as a first compound 322 and provides blue emission. For example, the first compound 322 in the first EML 320 may be one of the compounds in Formula 4.
The EML 320 may further include a second compound 324. For example, the second compound 324 may be represented by Formula 5 and may be one of the compounds in Formula 6.
In the first EML 320, the first compound 322 has a weight % being smaller than the second compound 324. The first compound 322 may act as a dopant (an emitter), and the second compound 324 may act as a host. For example, in the first EML 320, the first compound 322 may have a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency and lifespan, the weight % of the first compound 322 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The first EBL 316 may include the compound in Formula 7 as the electron blocking material. In addition, the first HBL 318 may include at least one of the compounds in Formula 9 and Formula 11-1 as the hole blocking material.
The second emitting part 330 includes the second EML 340. In addition, the second emitting part 330 may further include a second EBL 334 between the CGL 350 and the second EML 340 and a second HBL 336 between the second EML 340 and the second electrode 164.
In addition, the second emitting part 330 may further include a second HTL 332 between the CGL 350 and the second EBL 334 and an EIL 338 between the second HBL 336 and the second electrode 164.
The second EML 340 includes the emitting compound in Formula 1 as a third compound 342 and provides blue emission. For example, the third compound 342 in the second EML 340 may be one of the compounds in Formula 4.
The second EML 340 may further include a fourth compound 344. For example, the fourth compound 344 may be represented by Formula 5 and may be one of the compounds in Formula 6.
In the second EML 340, the third compound 342 may have a weight % being less than the fourth compound 344. In the second EML 340, the third compound 342 may act as a dopant (an emitter), and the fourth compound 344 may act as a host. For example, in the second EML 340, the third compound 342 has a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency and lifespan, the weight % of the third compound 342 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The third compound 342 in the second EML 340 and the first compound 322 in the first EML 320 may be same or different, and the fourth compound 344 in the second EML 340 and the second compound 324 in the first EML 320 may be same or different. In addition, the weight % of the first compound 322 in the first EML 320 and the weight % of the third compound 342 in the second EML 340 may be same or different.
The second EBL 334 may include the electron blocking material in Formula 7. In addition, the second HBL 336 may include at least one of the hole blocking material in Formula 9 and the hole blocking material in Formula 11-1.
The CGL 350 is positioned between the first and second emitting parts 310 and 330. Namely, the first and second emitting parts 310 and 330 are connected through the CGL 350. The CGL 350 may be a P-N junction CGL of an N-type CGL 352 and a P-type CGL 354.
The N-type CGL 352 is positioned between the first HBL 318 and the second HTL 332, and the P-type CGL 354 is positioned between the N-type CGL 352 and the second HTL 332.
In the OLED D, since each of the first and second EMLs 320 and 340 includes the emitting compound in Formula 1 as the first and third compounds 322 and 342, respectively, the emitting efficiency and the lifespan of the OLED D and the organic light emitting display device 100 are improved.
In addition, since the first and second emitting parts 310 and 330 for emitting blue light are stacked, the organic light emitting display device 100 provides an image having high color temperature.
As shown in
Each of the first and second substrates 410 and 470 may be a glass substrate or a flexible substrate. For example, each of the first and second substrates 410 and 470 may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate or a polycarbonate (PC) substrate.
A buffer layer 420 is formed on the substrate, and the TFT Tr corresponding to each of the red, green and blue pixels RP, GP and BP is formed on the buffer layer 420. The buffer layer 420 may be omitted.
A semiconductor layer 422 is formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polycrystalline silicon.
A gate insulating layer 424 is formed on the semiconductor layer 422. The gate insulating layer 424 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.
A gate electrode 430, which is formed of a conductive material, e.g., metal, is formed on the gate insulating layer 424 to correspond to a center of the semiconductor layer 422.
An interlayer insulating layer 432, which is formed of an insulating material, is formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material, e.g., silicon oxide or silicon nitride, or an organic insulating material, e.g., benzocyclobutene or photo-acryl.
The interlayer insulating layer 432 includes first and second contact holes 434 and 436 exposing both sides of the semiconductor layer 422. The first and second contact holes 434 and 436 are positioned at both sides of the gate electrode 430 to be spaced apart from the gate electrode 430.
A source electrode 440 and a drain electrode 442, which are formed of a conductive material, e.g., metal, are formed on the interlayer insulating layer 432.
The source electrode 440 and the drain electrode 442 are spaced apart from each other with respect to the gate electrode 430 and respectively contact both sides of the semiconductor layer 422 through the first and second contact holes 434 and 436.
The semiconductor layer 422, the gate electrode 430, the source electrode 440 and the drain electrode 442 constitute the TFT Tr. The TFT Tr serves as a driving element. Namely, the TFT Tr may correspond to the driving TFT Td (of
Although not shown, the gate line and the data line cross each other to define the pixel, and the switching TFT is formed to be connected to the gate and data lines. The switching TFT is connected to the TFT Tr as the driving element.
In addition, the power line, which may be formed to be parallel to and spaced apart from one of the gate and data lines, and the storage capacitor for maintaining the voltage of the gate electrode of the TFT Tr in one frame may be further formed.
A passivation layer 450, which includes a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr, is formed to cover the TFT Tr.
A first electrode 460, which is connected to the drain electrode 442 of the TFT Tr through the drain contact hole 452, is separately formed in each pixel and on the passivation layer 450. The first electrode 460 may be an anode and may be formed of a conductive material, e.g., a transparent conductive oxide (TCO), having a relatively high work function. For example, the first electrode 460 may be formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO) or aluminum-zinc-oxide (A1:ZnO, AZO).
When the organic light emitting display device 400 is operated in a bottom-emission type, the first electrode 460 may have a single-layered structure of the transparent conductive material layer. When the Organic light emitting display device 400 is operated in a top-emission type, the first electrode 460 may further include a reflection electrode or a reflection layer. For example, the reflection electrode or the reflection layer may be formed of silver (Ag) or aluminum-palladium-copper (APC) alloy. In this instance, the first electrode 460 may have a triple-layered structure of ITO/Ag/ITO or ITO/APC/ITO.
A bank layer 466 is formed on the passivation layer 450 to cover an edge of the first electrode 460. Namely, the bank layer 466 is positioned at a boundary of the pixel and exposes a center of the first electrode 460 in the pixel. Since the OLED D emits the white light in the red, green and blue pixels RP, GP and BP, the organic emitting layer 462 may be formed as a common layer in the red, green and blue pixels RP, GP and BP without separation. The bank layer 466 may be formed to prevent a current leakage at an edge of the first electrode 460 and may be omitted.
An organic emitting layer 462 is formed on the first electrode 460.
Referring to
The first electrode 460 may be formed of a conductive material having a relatively high work function to serve as an anode for injecting a hole into the organic emitting layer 462. The second electrode 464 may be formed of a conductive material having a relatively low work function to serve as a cathode for injecting an electron into the organic emitting layer 462.
The CGL 750 is positioned between the first and second emitting parts 710 and 730, and the first emitting part 710, the CGL 750 and the second emitting part 730 are sequentially stacked on the first electrode 460. Namely, the first emitting part 710 is positioned between the first electrode 460 and the CGL 750, and the second emitting part 730 is positioned between the second electrode 464 and the CGL 750.
The first emitting part 710 includes a first EML 720. In addition, the first emitting part 710 may further include a first EBL 716 between the first electrode 460 and the first EML 720 and a first HBL 718 between the first EML 720 and the CGL 750.
In addition, the first emitting part 710 may further include a first HTL 714 between the first electrode 460 and the first EBL 716 and an HIL 712 between the first electrode 460 and the first HTL 714.
The first EML 720 includes the emitting compound in Formula 1 as a first compound 722 and provides blue emission. For example, the first compound 722 in the first EML 720 may be one of the compounds in Formula 4.
The EML 720 may further include a second compound 724. For example, the second compound 724 may be represented by Formula 5 and may be one of the compounds in Formula 6.
In the first EML 720, the first compound 722 has a weight % being smaller than the second compound 724. The first compound 722 may act as a dopant (an emitter), and the second compound 724 may act as a host. For example, in the first EML 720, the first compound 722 may have a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency and lifespan, the weight % of the first compound 722 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The first EBL 716 may include the compound in Formula 7 as the electron blocking material. In addition, the first HBL 718 may include at least one of the compounds in Formula 9 and Formula 11-1 as the hole blocking material.
The second emitting part 730 includes the second EML 740. In addition, the second emitting part 730 may further include a second EBL 734 between the CGL 750 and the second EML 740 and a second HBL 736 between the second EML 740 and the second electrode 464.
In addition, the second emitting part 730 may further include a second HTL 732 between the CGL 750 and the second EBL 734 and an EIL 738 between the second HBL 736 and the second electrode 464.
The second EML 740 may be a yellow-green EML. For example, the second EML 740 may include a yellow-green dopant 743 and a host 745. The yellow-green dopant 743 may be one of a yellow-green fluorescent compound, a yellow-green phosphorescent compound and a yellow-green delayed fluorescent compound. Alternatively, the second EML 740 may have a double-layered structure including a red EML and a green EML. Namely, the second EML 740 may emit yellow-green light or red/green light.
In the second EML 740, the host 745 may have a weight % of about 70 weight % to 99.9 weight %, and the yellow-green dopant 743 may have a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency, the yellow-green dopant 743 may have a weight % of about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The second EBL 734 may include the compound in Formula 7 as the electron blocking material. In addition, the second HBL 736 may include at least one of the compounds in Formula 9 and Formula 11-1 as the hole blocking material.
The CGL 750 is positioned between the first and second emitting parts 710 and 730. Namely, the first and second emitting parts 710 and 730 are connected through the CGL 750. The CGL 750 may be a P-N junction CGL of an N-type CGL 752 and a P-type CGL 754.
The N-type CGL 752 is positioned between the first HBL 718 and the second HTL 732, and the P-type CGL 754 is positioned between the N-type CGL 752 and the second HTL 732.
In
In the OLED D, since the first EML 720 or the second EML 740 includes the emitting compound 722 of the present disclosure such that the emitting efficiency and the lifespan of the OLED D and the organic light emitting display device 400 are significantly improved.
The OLED D including the first emitting part 710 providing the blue emission and the second emitting part 730 providing the yellow-green emission or the red/green emission, emits a white light.
Referring to
The first CGL 580 is positioned between the first and second emitting parts 530 and 550, and the second CGL 590 is positioned between the second and third emitting parts 550 and 570. Namely, the first emitting part 530, the first CGL 580, the second emitting part 550, the second CGL 590 and the third emitting part 570 are sequentially stacked on the first electrode 460. In other words, the first emitting part 530 is positioned between the first electrode 460 and the first CGL 580, the second emitting part 550 is positioned between the first and second CGLs 580 and 590, and the third emitting part 570 is positioned between the second electrode 464 and the second CGL 590.
The first emitting part 530 may include an HIL 532, a first HTL 534, a first EBL 536, the first EML 520 and a first HBL 538 sequentially stacked on the first electrode 460. For example, the HIL 532, the first HTL 534 and the first EBL 536 are positioned between the first electrode 460 and the first EML 520, and the first HBL 538 is positioned between the first EML 520 and the first CGL 580.
The first EML 520 includes the emitting compound in Formula 1 as a first compound 522 and provides blue emission. For example, the first compound 522 in the first EML 520 may be one of the compounds in Formula 4.
The first EML 520 may further include a second compound 524. For example, the second compound 524 may be represented by Formula 5 and may be one of the compounds in Formula 6.
In the first EML 520, the first compound 522 has a weight % being smaller than the second compound 524. The first compound 522 may act as a dopant (an emitter), and the second compound 524 may act as a host. For example, in the first EML 520, the first compound 522 may have a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency and lifespan, the weight % of the first compound 522 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The first EBL 536 may include the compound in Formula 7 as the electron blocking material. In addition, the first HBL 538 may include at least one of the compounds in Formula 9 and Formula 11-1 as the hole blocking material.
The second emitting part 550 may include a second HTL 552, the second EML 540 and an electron transporting layer (ETL) 554. The second HTL 552 is positioned between the first CGL 580 and the second EML 540, and the ETL 554 is positioned between the second EML 540 and the second CGL 590.
The second EML 540 may provide red and green emission. For example, the second EML 540 may include a first layer being a red EML and a second layer being a green EML. The first layer may include a host and a red dopant, and the second layer may include a host and a green dopant. In addition, the second EML 540 may further include a third layer being a yellow-green EML. For example, the third layer may include a host and a yellow-green dopant. In this instance, the third layer may be positioned between the first and second layers. Namely, the second EML 540 may provide red, green and yellow-green emission.
The third emitting part 570 may include a third HTL 572, a second EBL 574, the third EML 560, a second HBL 576 and an EIL 578.
The third EML 560 includes the emitting compound in Formula 1 as a third compound 562 and provides blue emission. For example, the third compound 562 in the third EML 560 may be one of the compounds in Formula 4.
The third EML 560 may further include a fourth compound 564. For example, the fourth compound 564 may be represented by Formula 5 and may be one of the compounds in Formula 6.
In the third EML 560, the third compound 562 may have a weight % being less than the fourth compound 564. In the third EML 560, the third compound 562 may act as a dopant (an emitter), and the fourth compound 564 may act as a host. For example, in the third EML 560, the third compound 562 has a weight % of about 0.1 weight % to 30 weight %. To provide sufficient emitting efficiency and lifespan, the weight % of the third compound 562 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.
The third compound 562 in the third EML 560 and the first compound 522 in the first EML 520 may be same or different, and the fourth compound 564 in the third EML 560 and the second compound 524 in the first EML 520 may be same or different. In addition, the weight % of the first compound 522 in the first EML 520 and the weight % of the third compound 562 in the third EML 560 may be same or different.
The second EBL 574 may include the electron blocking material in Formula 7. In addition, the second HBL 576 may include at least one of the hole blocking material in Formula 9 and the hole blocking material in Formula 11-1.
The first CGL 580 is positioned between the first emitting part 530 and the second emitting part 550, and the second CGL 590 is positioned between the second emitting part 550 and the third emitting part 570. Namely, the first and second emitting parts 530 and 550 are connected through the first CGL 580, and the second and third emitting parts 550 and 570 are connected through the second CGL 590. The first CGL 580 may be a P-N junction CGL of a first N-type CGL 582 and a first P-type CGL 584, and the second CGL 590 may be a P-N junction CGL of a second N-type CGL 592 and a second P-type CGL 594.
In the first CGL 580, the first N-type CGL 582 is positioned between the first HBL 538 and the second HTL 552, and the first P-type CGL 584 is positioned between the first N-type CGL 582 and the second HTL 552.
In the second CGL 590, the second N-type CGL 592 is positioned between the ETL 554 and the third HTL 572, and the second P-type CGL 594 is positioned between the second N-type CGL 592 and the third HTL 572.
In the OLED D, since each of the first and third EMLs 520 and 560 includes the emitting compound in Formula 1 as the first and third compounds 522 and 562, respectively, the emitting efficiency and the lifespan of the OLED D and the organic light emitting display device 400 are improved.
In addition, the OLED D including the first and third emitting parts 530 and 570 with the second emitting part 550, which emits yellow-green light, red/green light or red/green/yellow-green light, can emit white light.
In
Referring to
In the organic light emitting display device 400, since the light emitted from the organic emitting layer 462 is incident to the color filter layer 480 through the second electrode 464, the second electrode 464 has a thin profile for transmitting the light.
The first electrode 460, the organic emitting layer 462 and the second electrode 464 constitute the OLED D.
The color filter layer 480 is positioned over the OLED D and includes a red color filter 482, a green color filter 484 and a blue color filter 486 respectively corresponding to the red, green and blue pixels RP, GP and BP. The red color filter 482 may include at least one of red dye and red pigment, the green color filter 484 may include at least one of green dye and green pigment, and the blue color filter 486 may include at least one of blue dye and blue pigment.
Although not shown, the color filter layer 480 may be attached to the OLED D by using an adhesive layer. Alternatively, the color filter layer 480 may be formed directly on the OLED D.
An encapsulation film (not shown) may be formed to prevent penetration of moisture into the OLED D. For example, the encapsulation film may include a first inorganic insulating layer, an organic insulating layer and a second inorganic insulating layer sequentially stacked, but it is not limited thereto. The encapsulation film may be omitted.
A polarization plate (not shown) for reducing an ambient light reflection may be disposed over the top-emission type OLED D. For example, the polarization plate may be a circular polarization plate.
In the OLED of
A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red color conversion layer, a green color conversion layer and a blue color conversion layer respectively corresponding to the red, green and blue pixels RP, GP and BP. The white light from the OLED D is converted into the red light, the green light and the blue light by the red, green and blue color conversion layer, respectively. For example, the color conversion layer may include a quantum dot. Accordingly, the color purity of the organic light emitting display device 400 may be further improved.
The color conversion layer may be included instead of the color filter layer 480.
As described above, in the organic light emitting display device 400, the OLED D in the red, green and blue pixels RP, GP and BP emits the white light, and the white light from the organic light emitting diode D passes through the red color filter 482, the green color filter 484 and the blue color filter 486. As a result, the red light, the green light and the blue light are provided from the red pixel RP, the green pixel GP and the blue pixel BP, respectively.
In
As shown in
Although not shown, a color filter may be formed between the second substrate 670 and each color conversion layer 680.
Each of the first and second substrates 610 and 670 may be a glass substrate or a flexible substrate. For example, each of the first and second substrates 610 and 670 may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate or a polycarbonate (PC) substrate.
A TFT Tr, which corresponding to each of the red, green and blue pixels RP, GP and BP, is formed on the first substrate 610, and a passivation layer 650, which has a drain contact hole 652 exposing an electrode, e.g., a drain electrode, of the TFT Tr is formed to cover the TFT Tr.
The OLED D including a first electrode 660, an organic emitting layer 662 and a second electrode 664 is formed on the passivation layer 650. In this instance, the first electrode 660 may be connected to the drain electrode of the TFT Tr through the drain contact hole 652.
A bank layer 666 is formed on the passivation layer 650 to cover an edge of the first electrode 660. Namely, the bank layer 666 is positioned at a boundary of the pixel and exposes a center of the first electrode 660 in the pixel. Since the OLED D emits the blue light in the red, green and blue pixels RP, GP and BP, the organic emitting layer 662 may be formed as a common layer in the red, green and blue pixels RP, GP and BP without separation. The bank layer 666 may be formed to prevent a current leakage at an edge of the first electrode 660 and may be omitted.
The OLED D emits a blue light and may have a structure shown in
The color conversion layer 680 includes a first color conversion layer 682 corresponding to the red pixel RP and a second color conversion layer 684 corresponding to the green pixel GP. For example, the color conversion layer 680 may include an inorganic color conversion material such as a quantum dot. The color conversion layer 680 is not presented in the blue pixel BP such that the OLED D in the blue pixel BP may directly face the second substrate 670.
The blue light from the OLED D is converted into the red light by the first color conversion layer 682 in the red pixel RP, and the blue light from the OLED D is converted into the green light by the second color conversion layer 684 in the green pixel GP.
Accordingly, the organic light emitting display device 600 can display a full-color image.
On the other hand, when the light from the OLED D passes through the first substrate 610, the color conversion layer 680 is disposed between the OLED D and the first substrate 610.
It will be apparent to those skilled in the art that various modifications and variations can be made in the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Thus, it is intended that the modifications and variations cover this disclosure provided they come within the scope of the appended claims and their equivalents.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2021-0178383 | Dec 2021 | KR | national |
