Patent Application
20230389412
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0067161, filed on May 31, 2022, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
The present disclosure herein relates to a light emitting device and a fused polycyclic compound for the light emitting device.
Recently, the development of an organic electroluminescence display apparatus as an image display apparatus is being actively conducted. Unlike liquid crystal display apparatuses and/or the like, the organic electroluminescence display apparatus is a so-called self-luminescent display apparatus in which holes and electrons injected from a first electrode and a second electrode recombine in an emission layer, and thus a luminescent material including an organic compound in the emission layer emits light to implement display (e.g., to display an image).
In the application of an organic electroluminescence device to a display apparatus, there is a demand for an organic electroluminescence device having a low driving voltage, a high luminous efficiency, and/or a long service life, and the development on materials, for an organic electroluminescence device, capable of stably attaining such characteristics is being continuously pursued.
In recent years, particularly in order to implement a highly efficient organic electroluminescence device, technologies pertaining to phosphorescence emission utilizing triplet state energy or delayed fluorescence utilizing triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons are being developed, and thermally activated delayed fluorescence (TADF) materials utilizing delayed fluorescence phenomenon are being developed.
Aspects according to embodiments of the present disclosure are directed toward a light emitting device in which luminous efficiency and a device service life are improved.
Aspects according to embodiments of the present disclosure are directed toward a fused polycyclic compound capable of improving luminous efficiency and a device service life of a light emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an embodiment of the present disclosure, a light emitting device includes a first electrode, a second electrode facing the first electrode, and an emission layer between the first electrode and the second electrode.
The emission layer includes a first compound represented by Formula 1:
In Formula 1,
In an embodiment, in Formula 1 and Formula 2, at least two from among R2, R5, R6, R9, R10, and Ra to Re may be substituents represented by Formula 3.
In an embodiment, the first compound represented by Formula 1 may be represented by any one from among Formula 1-1 to Formula 1-3:
In Formula 1-1 to Formula 1-3, R1-1 to R11-1 and Ra1 to Re1 may each independently be a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, at least two from among Ra1 to Re1 are substituents represented by Formula 3, and X1, X2 and R12 may be the same as defined in Formula 1.
In an embodiment, the first compound represented by Formula 1 may be represented by any one from among Formula 1-4 to Formula 1-6:
In Formula 1-4 to Formula 1-6, R1-2 to R11-2, Ra1 to Re1, and Ra2 to Re2 may each independently be a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, at least two from among Ra1 to Re1 and Ra2 to Re2 are substituents represented by Formula 3, and X1, X2 and R12 may be the same as defined in Formula 1.
In an embodiment, the first compound represented by Formula 1 may be represented by any one from among Formula 1-7 to Formula 1-9:
In Formula 1-7 to Formula 1-9, R1-3 to R11-3 may each independently be a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, Y1-1 to Y4-1 and Y1-2 to Y4-2 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, e to g may each independently be an integer of 0 to 5, h is an integer of 0 to 4, and X1, X2, R12 and a to d may each independently be the same as defined in Formula 1 and Formula 3.
In an embodiment, the first compound represented by Formula 1 may be represented by any one from among Formula 1-10 to Formula 1-12:
In an embodiment, the substituent represented by Formula 2 may be represented by Formula 2-1:
In Formula 2-1, Y11 to Y18 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, m1 to m3 and m5 to m7 may each independently be an integer of 0 to 5, m4 and m8 may each independently be an integer of 0 to 4, and L may be the same as defined in Formula 2.
In an embodiment, the substituent represented by Formula 3 may be represented by Formula 3-1:
In Formula 3-1, Y21 and Y22 may each independently be a hydrogen atom or a deuterium atom, p is an integer of 0 to 4, and q is an integer of 0 to 5.
In an embodiment, the emission layer may further include a second compound represented by Formula H-1:
In Formula H-1, L1 may be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, Ar1 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, R31 and R32 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and n31 and n32 may each independently be an integer of 0 to 4.
In an embodiment, the emission layer may further include a third compound represented by Formula H-2:
In Formula H-2, Z1 to Z3 may each independently be N or CR36, at least one from among Z1 to Z3 may be N, and R33 to R36 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring.
In an embodiment, the emission layer may further include a fourth compound represented by Formula D-1:
In Formula D-1, Q1 to Q4 may each independently be C or N, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, L11 to L1a may each independently be a direct linkage,
a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, b1 to b3 may each independently be 0 or 1, R41 to R46 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and d1 to d4 may each independently be an integer of 0 to 4.
In an embodiment of the present disclosure, a fused polycyclic compound may be represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated in and constitute a part of this specification. The drawings illustrate example embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. In the drawings:
The present disclosure may be modified in many alternate forms, and thus example embodiments will be shown in the drawings and described in more detail. It should be understood, however, that it is not intended to limit the present disclosure to the particular forms disclosed, but rather, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the present disclosure.
When explaining each of drawings, like reference numbers are used for referring to like elements. In the accompanying drawings, the dimensions of each structure may be exaggeratingly illustrated for clarity of the present disclosure. It will be understood that, although the terms “first,” “second,” etc., may be used herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only used to distinguish one element from another. For example, a first component could be termed a second component, and, similarly, a second component could be termed a first component, without departing from the scope of the present disclosure. The terms of a singular form may include plural forms unless the context clearly indicates otherwise.
In the present application, it will be understood that the terms “include,” “have” and/or the like specify the presence of features, numbers, steps, operations, components, parts, or combinations thereof disclosed in the specification, but do not exclude the possibility of presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.
In the present application, when a layer, a film, a region, or a plate is referred to as being “above” or “on an upper portion of” another layer, film, region, or plate, it can be not only “directly on” the other layer, film, region, or plate, but intervening layers, films, regions, or plates may also be present. On the contrary to this, when a layer, a film, a region, or a plate is referred to as being “below,” or “in a lower portion of” another layer, film, region, or plate, it can be not only directly under the other layer, film, region, or plate, but intervening layers, films, regions, or plates may also be present. In some embodiments, it will be understood that when a part is referred to as being “on” another part, it can be disposed above the other part, or disposed under the other part as well.
In the specification, the term “substituted or unsubstituted” may refer to an unsubstituted group or a group substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In addition, each of the example substituents may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.
In the specification, the phrase “bonded to an adjacent group to form a ring” may refer to that one group is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocycle includes an aliphatic heterocycle and an aromatic heterocycle. The hydrocarbon ring and the heterocycle may be monocyclic or polycyclic. In addition, the rings formed by adjacent groups being bonded to each other may be connected to another ring to form a spiro structure.
In the specification, the term “adjacent group” may refer to a substituent substituted for an atom which is directly linked to an atom substituted with a corresponding substituent, another substituent substituted for an atom which is substituted with a corresponding substituent, or a substituent sterically positioned at the nearest position to a corresponding substituent. For example, two methyl groups in 1,2-dimethylbenzene may be interpreted as “adjacent groups” to each other and two ethyl groups in 1,1-diethylcyclopentane may be interpreted as “adjacent groups” to each other. In addition, two methyl groups in 4,5-dimethylphenanthrene may be interpreted as “adjacent groups” to each other.
In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
In the specification, the alkyl group may be a linear, branched or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 1 to 10, or 1 to 6. Examples of the alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, an i-butyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an i-pentyl group, a neopentyl group, a t-pentyl group, a cyclopentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethylhexyl group, a 2-butylhexyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-t-butylcyclohexyl group, an n-heptyl group, a 1-methylheptyl group, a 2,2-dimethylheptyl group, a 2-ethylheptyl group, a 2-butylheptyl group, an n-octyl group, a t-octyl group, a 2-ethyloctyl group, a 2-butyloctyl group, a 2-hexyloctyl group, a 3,7-dimethyloctyl group, a cyclooctyl group, an n-nonyl group, an n-decyl group, an adamantyl group, a 2-ethyldecyl group, a 2-butyldecyl group, a 2-hexyldecyl group, a 2-octyldecyl group, an n-undecyl group, an n-dodecyl group, a 2-ethyldodecyl group, a 2-butyldodecyl group, a 2-hexyldocecyl group, a 2-octyldodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a 2-hexylhexadecyl group, a 2-octylhexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a 2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a 2-octyleicosyl group, an n-henicosyl group, an n-docosyl group, an n-tricosyl group, an n-tetracosyl group, an n-pentacosyl group, an n-hexacosyl group, an n-heptacosyl group, an n-octacosyl group, an n-nonacosyl group, an n-triacontyl group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, a cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to Examples of the cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-t-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, a 1-adamantyl group, a 2-adamantyl group, an isobornyl group, a bicycloheptyl group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, the alkenyl group refers to a hydrocarbon group including at least one carbon double bond in the middle or at the terminal of an alkyl group having 2 or more carbon atoms. The alkenyl group may be a linear chain or a branched chain. The number of carbon atoms in the alkenyl group is not specifically limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group include a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1,3-butadienyl aryl group, a styrenyl group, a styryl vinyl group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group may include a phenyl group, a naphthyl group, a fluorene group, an anthracene group, a phenanthrene group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quinquephenyl group, a sexiphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthene group, a chrysene group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows. However, the embodiment of the present disclosure is not limited thereto.
The heterocyclic group as used herein refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, or Se as a heteroatom. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.
In the specification, the heteroaryl group may include at least one of B, O, N, P, Si, or S as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group may include a thiophene group, a furan group, a pyrrole group, an imidazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroarylcarbazole group, an N-alkylcarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a thienothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilole group, a dibenzofuran group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, the above description of the aryl group may be applied to an arylene group except that the arylene group is a divalent group. The above description of the heteroaryl group may be applied to a heteroarylene group except that the heteroarylene group is a divalent group.
In the specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, the thio group may include an alkylthio group and an arylthio group. The thio group may refer to that a sulfur atom is bonded to the alkyl group or the aryl group as defined above. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a naphthylthio group, but the embodiment of the present disclosure is not limited thereto.
In the specification, an oxy group may refer to that an oxygen atom is bonded to the alkyl group or the aryl group as defined above. The oxy group may include an alkoxy group and an aryl oxy group. The alkoxy group may be a linear chain, a branched chain or a ring (e.g., cyclic) chain. The number of carbon atoms in the alkoxy group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. Examples of the oxy group may include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a benzyloxy group, etc., but the embodiment of the present disclosure is not limited thereto.
The boron group as used herein may refer to that a boron atom is bonded to the alkyl group or the aryl group as defined above. The boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group may include a dimethylboron group, a trimethylboron group, a t-butyldimethylboron group, a diphenylboron group, a phenylboron group, etc., but the embodiment of the present disclosure is not limited thereto.
In the specification, the number of carbon atoms in an amine group is not specifically limited, but may be 1 to 30. The amine group may include an alkyl amine group and an aryl amine group. Examples of the amine group may include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, a triphenylamine group, etc., but the embodiment of the present disclosure is not limited thereto. In the specification, a direct linkage may refer to a single bond.
In the specification,
and “-*” refer to a position to be connected.
Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.
The display apparatus DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light emitting devices ED-1, ED-2, and ED-3. The display apparatus DD may include a plurality of light emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflection of external light in the display panel DP. The optical layer PP may include, for example, a polarization layer or a color filter layer. In some embodiments, unlike the configuration illustrated in the drawing, the optical layer PP may not be provided in the display apparatus DD of an embodiment.
A base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member which provides a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment of the present disclosure is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the configuration illustrated, in an embodiment, the base substrate BL may not be provided.
The display apparatus DD according to an embodiment may further include a filling layer. The filling layer may be disposed between a display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic-based resin, a silicone-based resin, or an epoxy-based resin.
The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and the display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, the light emitting devices ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting devices ED-1, ED-2, and ED-3.
The base layer BS may be a member which provides a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.
Each of the light emitting devices ED-1, ED-2, and ED-3 may have a structure of any light emitting device ED of embodiments according to
The encapsulation layer TFE may cover the light emitting devices ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one layer or a plurality of layers. The encapsulation layer TFE includes at least one insulation layer. The encapsulation layer TFE according to an embodiment may include at least one inorganic film (hereinafter, an encapsulation-inorganic film). The encapsulation layer TFE according to an embodiment may also include at least one organic film (hereinafter, an encapsulation-organic film) and at least one encapsulation-inorganic film.
The encapsulation-inorganic film protects the display device layer DP-ED from moisture/oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign substances such as dust particles. The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, and/or the like, but the embodiment of the present disclosure is not particularly limited thereto. The encapsulation-organic film may include an acrylic-based compound, an epoxy-based compound, and/or the like. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiment of the present disclosure is not particularly limited thereto.
The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.
Referring to
Each of the light emitting regions PXA-R, PXA-G, and PXA-B may be a region divided by the pixel defining film PDL. The non-light emitting areas NPXA may be areas between the adjacent light emitting areas PXA-R, PXA-G, and PXA-B, which correspond to the pixel defining film PDL. In the specification, each of the light emitting regions PXA-R, PXA-G, and PXA-B may respectively correspond to a pixel. The pixel defining film PDL may divide the light emitting devices ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light emitting devices ED-1, ED-2, and ED-3 may be disposed in openings OH defined in the pixel defining film PDL and separated from each other.
The light emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the color of light generated from the light emitting devices ED-1, ED-2, and ED-3. In the display apparatus DD of an embodiment illustrated in
In the display apparatus DD according to an embodiment, the plurality of light emitting devices ED-1, ED-2 and ED-3 may be to emit light (e.g., light beams) having wavelengths different from each other. For example, in an embodiment, the display apparatus DD may include a first light emitting device ED-1 that emits red light, a second light emitting device ED-2 that emits green light, and a third light emitting device ED-3 that emits blue light. For example, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B of the display apparatus DD may correspond to the first light emitting device ED-1, the second light emitting device ED-2, and the third light emitting device ED-3, respectively.
However, the embodiment of the present disclosure is not limited thereto, and the first to third light emitting devices ED-1, ED-2, and ED-3 may be to emit light (e.g., light beams) in substantially the same wavelength range or at least one light emitting device may be to emit light (e.g., light beam) in a wavelength range different from the others. For example, the first to third light emitting devices ED-1, ED-2, and ED-3 may all emit blue light.
The light emitting regions PXA-R, PXA-G, and PXA-B in the display apparatus DD according to an embodiment may be arranged in a stripe form. Referring to
In some embodiments, an arrangement form of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to the configuration illustrated in
In some embodiments, the areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in an embodiment, the area of the green light emitting region PXA-G may be smaller than that of the blue light emitting region PXA-B, but the embodiment of the present disclosure is not limited thereto.
Hereinafter,
Compared with
The first electrode EL1 has conductivity (e.g., is a conductor). The first electrode EU may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment of the present disclosure is not limited thereto. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EU may include at least one selected from among Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, or an oxide thereof.
When the first electrode EL1 is the transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and/or indium tin zinc oxide (ITZO). When the first electrode EU is the transflective electrode or the reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca (a stacked structure of LiF and Ca), LiF/Al (a stacked structure of LiF and Al), Mo, Ti, W, a compound or mixture thereof (e.g., a mixture of Ag and Mg). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above-described materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but the embodiment of the present disclosure is not limited thereto. In addition, the embodiment of the present disclosure is not limited thereto, and the first electrode EL1 may include the above-described metal materials, combinations of at least two metal materials of the above-described metal materials, oxides of the above-described metal materials, and/or the like. The thickness of the first electrode EL1 may be from about 700 Å to about 10,000 Å. For example, the thickness of the first electrode EL1 may be from about 1,000 Å to about 3,000 Å.
The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer or an emission-auxiliary layer, or an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, from about 50 Å to about 15,000 Å.
The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.
For example, the hole transport region HTR may have a single layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single layer structure formed of a plurality of different materials, or a structure in which a hole injection layer HIL/hole transport layer HTL, a hole injection layer HIL/hole transport layer HTL/buffer layer, a hole injection layer HIL/buffer layer, a hole transport layer HTL/buffer layer, or a hole injection layer HIL/hole transport layer HTL/electron blocking layer EBL are stacked in the respective stated order from the first electrode EL1, but the embodiment of the present disclosure is not limited thereto.
The hole transport region HTR may be formed utilizing one or more suitable methods such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
The hole transport region HTR may include a compound represented by Formula H-20:
In Formula H-20 above, L1 and L2 may each independently be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. a and b may each independently be an integer of 0 to 10. In some embodiments, when a or b is an integer of 2 or greater, a plurality of L1's and L2's may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
In Formula H-20, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In some embodiments, in Formula H-20, Ar3 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
The compound represented by Formula H-20 above may be a monoamine compound (e.g., a compound including a single amine group). In some embodiments, the compound represented by Formula H-20 above may be a diamine compound in which at least one from among Ar1 to Ar3 includes the amine group as a substituent. In some embodiments, the compound represented by Formula H-20 above may be a carbazole-based compound including a substituted or unsubstituted carbazole group in at least one of Ar1 or Ar2, or a fluorene-based compound including a substituted or unsubstituted fluorene group in at least one of Ar1 or Ar2.
The compound represented by Formula H-20 may be represented by any one from among the compounds of Compound Group H. However, the compounds listed in Compound Group H are only examples, and the compounds represented by Formula H-20 are not limited to those represented by Compound Group H:
The hole transport region HTR may include a phthalocyanine compound such as copper phthalocyanine; N1,N1′-([1,1′-biphenyl]-4,4′-diyl)bis(N4-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine) (DNTPD), 4,4′,4″-[tris(3-methylphenyl)phenylamino] triphenylamine (m-MTDATA), 4,4′4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4′-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f: 2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HATCN), etc.
The hole transport region HTR may include a carbazole-based derivative such as N-phenyl carbazole and/or polyvinyl carbazole, a fluorene-based derivative, a triphenylamine-based derivative such as N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD) and/or 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl]benzenamine] (TAPC), 4,4′-bis[N,N-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.
In some embodiments, the hole transport region HTR may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9′-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazol-9-Abenzene (mDCP), etc.
The hole transport region HTR may include the above-described compounds of the hole transport region in at least one of a hole injection layer HIL, a hole transport layer HTL, or an electron blocking layer EBL.
The thickness of the hole transport region HTR may be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 5,000 Å. When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, a thickness of about 30 Å to about 1,000 Å. When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about 250 Å to about 1,000 Å. For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about 10 Å to about 1,000 Å. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL and the electron blocking layer EBL satisfy the above-described ranges, satisfactory hole transport properties may be achieved without a substantial increase in driving voltage.
The hole transport region HTR may further include a charge generating material to increase conductivity in addition to the above-described materials. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, or a cyano group-containing compound, but the embodiment of the present disclosure is not limited thereto. For example, the p-dopant may include a metal halide compound such as CuI and/or RbI, a quinone derivative such as tetracyanoquinodimethane (TCNQ) and/or 2,3,5,6-tetrafluoro-7,7′8,8-tetracyanoquinodimethane (F4-TCNQ), a metal oxide such as tungsten oxide and/or molybdenum oxide, a cyano group-containing compound such as dipyrazino[2,3-f: 2′,3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HATCN) and/or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cya nomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but the embodiment of the present disclosure is not limited thereto.
As described above, the hole transport region HTR may further include at least one of the buffer layer or the electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL. The buffer layer may compensate for a resonance distance according to the wavelength of light emitted from the emission layer EML and may thus increase light emission efficiency. A material that may be included in the hole transport region HTR may be utilized as a material to be included in the buffer layer. The electron blocking layer EBL is a layer that serves to prevent or reduce the electron injection from the electron transport region ETR to the hole transport region HTR.
The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have a thickness of, for example, about 100 Å to about 1,000 Å or about 100 Å to about 300 Å. The emission layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.
The emission layer EML in the light emitting device ED according to an embodiment may include a fused polycyclic compound of an embodiment. In an embodiment, the emission layer EML may include the fused polycyclic compound of an embodiment as a dopant. The fused polycyclic compound of an embodiment may be a dopant material of the emission layer EML.
The fused polycyclic compound of an embodiment may include a core structure in which a plurality of aromatic rings are fused via at least one boron atom and at least two heteroatoms. For example, the fused polycyclic compound of an embodiment may include a structure in which first to third aromatic rings are fused via one boron atom, a first heteroatom, and a second heteroatom. The first aromatic ring and the second aromatic ring may be symmetric with respect to the boron atom in the fused ring structure. In some embodiments, the first heteroatom and the second heteroatom may each independently be a nitrogen atom, an oxygen atom, or a sulfur atom.
The fused polycyclic compound of an embodiment may include a first substituent and a second substituent, each of which is a steric hindrance substituent bonded to the core structure as described above. Each of the first substituent and the second substituent includes a triphenyl silane moiety, and a phenyl group (e.g., a fourth phenyl group) substituted at the meta-position, with respect to the position at which a silicon atom is linked, may be included in one phenyl group from among the triphenyl silane moiety.
The first substituent and the second substituent may be linked to the first to third aromatic rings in the fused polycyclic compound of an embodiment. For example, the first substituent and the second substituent may be directly linked to any one from among the first to third aromatic rings. The first substituent may be directly linked to any one from among the first to third aromatic rings, and the second substituent may be directly linked to a ring, to which the first substituent is not linked, from among the first to third aromatic rings. In some embodiments, at least one of the first substituent or the second substituent may be linked to the first to third aromatic rings via a linker containing a benzene moiety. In some embodiments, the first substituent and the second substituent may be linked to the first to third aromatic rings via one linker (e.g., the same linker that contains the benzene moiety). In some embodiments, the first substituent and the second substituent may be linked to the first to third aromatic rings via different linkers, respectively. In some embodiments, the first substituent may be directly linked to the first to third aromatic rings, and the second substituent may be linked to the first to third aromatic rings via the linker. The fused polycyclic compound of an embodiment is represented by Formula 1:
In Formula 1, X1 and X2 are each independently NR12, O, or S. In some embodiments, X1 and X2 may be the same. For example, both (e.g., simultaneously) X1 and X2 may be NR12. In some embodiments, in Formula 1, X1 and X2 may correspond to the first heteroatom and the second heteroatom, respectively, as described above.
In Formula 1, R1 to R11 are each independently a substituent represented by Formula 2, a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R1 to R11 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted a naphthyl group, or a substituted or unsubstituted carbazole group.
In Formula 1, R12 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R12 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
In Formula 2, L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. For example, L may be a direct linkage or a substituted or unsubstituted phenyl group.
In Formula 1, Ra to Re are each independently a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ra to Re may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted a naphthyl group, or a substituted or unsubstituted carbazole group.
In Formula 2, “-*” refers to a position linked to the fused structure represented by Formula 1.
In some embodiments, the substituent represented by Formula 2 may correspond to the linker containing a benzene moiety as described above.
In Formula 3, Y1 to Y4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Y1 to Y4 may each independently be a hydrogen atom or a deuterium atom.
In Formula 3, a to c are each independently an integer of 0 to 5, and d is an integer of 0 to 4. When each of a to d is 0, the fused polycyclic compound of an embodiment may not be substituted with each of Y1 to Y4. The case where each of a to c is 5 and d is 4 and Y1's to Y4's each are hydrogen atoms may be the same as the case where each of a to d is 0. When each of a to d is an integer of 2 or more, a plurality of Y1's to Y4's may each be the same or at least one from among the plurality of Y1's to Y4's may be different from the others.
In Formula 1 and Formula 2, at least two from among R1 to R11 and Ra to Re are substituents represented by Formula 3. In the fused polycyclic compound of an embodiment, at least two from among R1 to R11 may be substituents represented by Formula 3. For example, at least two from among R2, R5, R6, R9, and R10 may be substituents represented by Formula 3. In some embodiments, in the fused polycyclic compound of an embodiment, one from among R1 to R11 may be a substituent represented by Formula 2, and at least two from among Ra to Re in the substituent represented by Formula 2 may be substituents represented by Formula 3. In some embodiments, two from among R1 to R11 may be substituents represented by Formula 2, one from among Ra to Re in one substituent of the two substituents represented by Formula 2 may be a substituent represented by Formula 3, and one from among Ra to R e in the remaining one substituent of the two substituents represented by Formula 2 may be a substituent represented by Formula 3.
In Formula 3, “-*” refers to a position linked to the fused structure represented by Formula 1 or the substituent represented by Formula 2. In an embodiment, when any one from among R1 to R11 is the substituent represented by Formula 3, in Formula 3, “-*” refers to a position linked to the fused structure represented by Formula 1. In an embodiment, when any one from among R1 to R11 is represented by Formula 2, and in the substituent represented by Formula 2, any one from among Ra to Re is the substituent represented by Formula 3, in Formula 3, “-*” refers to a position linked to the substituent represented by Formula 2.
In some embodiments, the substituent represented by Formula 3 may correspond to each of the first substituent and the second substituent as described above.
In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1 to Formula 1-6:
Each of Formula 1-1 to Formula 1-6 represents the case where at least one from among R1 to R11 in Formula 1 is specified as a structure represented by Formula 2. Formula 1-1 to Formula 1-6 represent the cases where at least one of R2, R5, R6, R9, or R10 is a substituent represented by Formula 2. Formula 1-1 to Formula 1-3 represent the cases where any one from among R2, R5, R6, R9 and R10 is a substituent represented by Formula 2, and Formula 1-4 to Formula 1-6 represent the cases where any two from among R2, R5, R6, R9 and R10 are substituents represented by Formula 2. For example, Formula 1-1 represents the case where R2 in Formula 1 is a substituent represented by Formula 2, Formula 1-2 represents the case where R10 in Formula 1 is a substituent represented by Formula 2, and Formula 1-3 represents the case where R9 in Formula 1 is a substituent represented by Formula 2. Formula 1-4 represents the case where R5 and R10 in Formula 1 are each substituent represented by Formula 2, Formula 1-5 represents the case where R2 and R10 in Formula 1 are each substituent represented by Formula 2, and Formula 1-6 represents the case where R2 and R9 in Formula 1 are each substituents represented by Formula 2.
In Formula 1-1 to Formula 1-6, R1-1 to R11-1, R1-2 to R11-2, Ra1 to Re1, and Ra2 to Re2 may each independently be a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R1-1 to R11-1, R1-2 to R11-2, Ra1 to Re1, and Ra2 to Re2 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted carbazole group.
In Formula 1-1 to Formula 1-3, at least two from among Ra1 to Re1 may be the substituents represented (each represented) by Formula 3. For example, Rb1 and Rd1 may be the substituents represented by Formula 3. In Formula 1-4 to Formula 1-6, at least two from among Ra1 to Re1 and Ra2 to Re2 may be the substituents represented by Formula 3. For example, Ra1 and Rc2 may be the substituents represented by Formula 3.
In some embodiments, Formula 1-1 to Formula 1-6 may correspond to the cases where the first substituent and the second substituent as described above are linked to the first to third aromatic rings via a linker containing a benzene moiety. Formula 1-1 to Formula 1-3 may correspond to the cases where the first substituent and the second substituent as described above are linked to the first to third aromatic rings via one linker (e.g., the same linker that contains the benzene moiety), and
Formula 1-4 to Formula 1-6 may correspond to the cases where the first substituent and the second substituent as described above are linked to the first to third aromatic rings via different linkers, respectively.
In Formula 1-1 to Formula 1-6, the same as described in Formula 1 above may be applied to X1, X2, and R12.
In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-7 to Formula 1-9:
Each of Formula 1-7 to Formula 1-9 represents the case where at least two from among R1 to R11 in Formula 1 are specified as a structure represented by a Formula 3. Formula 1-7 to Formula 1-9 represent the cases where the type or kind of substituent of R2, R5, R6, R9 or R10 in Formula 1 is represented by Formula 3. For example, Formula 1-7 represents the case where R2 and R9 in Formula 1 are each represented by Formula 3, Formula 1-8 represents the case where R5 and R10 in Formula 1 are each represented by Formula 3, and Formula 1-9 represents the case where R5 and R9 in Formula 1 are each represented by Formula 3.
In Formula 1-7 to Formula 1-9, R1-3 to R11-3 may each independently be a substituent represented by Formula 3, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R1-3 to R11-3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted a naphthyl group, or a substituted or unsubstituted carbazole group.
In Formula 1-7 to Formula 1-9, Y1-1 to Y4-1, and Y1-2 to Y4-2 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Y1-1 to Y4-1, and Y1-2 to Y4-2 may each independently be a hydrogen atom or a deuterium atom.
In Formula 1-7 to Formula 1-9, e tog may each independently be an integer of 0 to 5, and h is an integer of 0 to 4. When each of e to h is 0, the fused polycyclic compound of an embodiment may not be substituted with each of Y1-2 to Y4-2. The case where each of e to g is 5 and h is 4 and Y1-2 's to Y4-2 's each are hydrogen atoms may be the same as the case where each of e to h is 0. When each of e to h is an integer of 2 or more, a plurality of Y1-2 's to Y4-2 's may each be the same or at least one from among the plurality of Y1-2 's to Y4-2 's may be different from the others.
In some embodiments, Formula 1-7 to Formula 1-9 may correspond to the cases where the first substituent and the second substituent as described above are directly linked to the first to third aromatic rings. For example, Formula 1-7 to Formula 1-9 may correspond to the cases where the first substituent is directly linked to any one from among the first to third aromatic rings, and the second substituent is directly linked to a ring, to which the first substituent is not linked, from among the first to third aromatic rings.
In Formula 1-7 to Formula 1-9, the same as described in Formula 1 and Formula 3 above may be applied to X1, X2, R12, and a to d.
In an embodiment, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-10 to Formula 1-12:
Formula 1-10 to Formula 1-12 represent the cases where types (kinds) of X1 and X2 in Formula 1 are specified and R12 is a substituted or unsubstituted phenyl group. Formula 1-10 represents the case where both (e.g., simultaneously) X1 and X2 in Formula 1 are NR12, Formula 1-11 represents the case where in Formula 1, X1 is NR12 and X2 is S, and Formula 1-12 represents the case where in Formula 1, X1 is NR12 and X2 is O.
In Formula 1-10 to Formula 1-12, X11 to X14 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, X11 to X14 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
In Formula 1-10 to Formula 1-12, n1 to n4 may each independently be an integer of 0 to 5. When each of n1 to n4 is 0, the fused polycyclic compound of an embodiment may not be substituted with each of X11 to X14. The case where each of n1 to n4 is 5 and X11's to X14's each are hydrogen atoms may be the same as the case where each of n1 to n4 is 0. When each of n1 to n4 is an integer of 2 or more, a plurality of X11's to X14's may each be the same or at least one from among the plurality of X11's to X14's may be different from the others.
In Formula 1-10 to Formula 1-12, the same as described in Formula 1 may be applied to R1 to R11.
In an embodiment, the fused polycyclic compound represented by Formula 1 may include a substituent represented by Formula 2-1. In the fused polycyclic compound represented by Formula 1, at least one from among R1 to R11 as described above may be the substituent represented by Formula 2-1.
Formula 2-1 represents the case where the types (kinds) of substituents of Ra to Re are specified in Formula 2. Formula 2-1 represents the case where Ra, Rc, and Re are hydrogen atoms in Formula 2, and Rb and Rd are represented by Formula 3.
In Formula 2-1, Y11 to Y18 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, L11 to L18 may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted t-butyl group.
In Formula 2-1, m1 to m3 and m5 to m7 may each independently be an integer of 0 to 5, m4 and m8 may each independently be an integer of 0 to 4. When each of m1 to m8 is 0, the fused polycyclic compound of an embodiment may not be substituted with each of Y11 to Y18. The case where each of m1 to m3 and m5 to m7 is 5, and each of m4 and m8 is 4, and a plurality of Y11's to Y18's are each hydrogen atoms may be the same as the case where each of m1 to m8 is 0. When each of m1 to m8 is an integer of 2 or more, a plurality of Y11's to Y18's may each be the same or at least one from among the plurality of Y11's to Y18's may be different from the others.
In some embodiments, the compound including the substituent represented by Formula 2-1 may correspond to the case where the first substituent and the second substituent as described above are linked to the first to third aromatic rings via one linker (e.g., the same linker).
In Formula 2-1, the same as described in Formula 2 may be applied to L and “-*.”
In an embodiment, the fused polycyclic compound represented by Formula 1 may include a substituent represented by Formula 3-1. In the fused polycyclic compound represented by Formula 1, at least one from among R1 to R11 as described above may be the substituent represented by Formula 3-1. In some embodiments, in the fused polycyclic compound represented by Formula 1, at least one from among R1 to R11 as described above may be the substituent represented by Formula 2, and at least one from among Ra to Re in the substituent represented by Formula 2 may be the substituent represented by Formula 3-1.
Formula 3-1 represents the case where the types (kinds) of substituents of Y1 to Y4 are specified in Formula 3. Formula 3-1 represents the case where in Formula 3, Y1 and Y2 are hydrogen atoms, and Y3 and Y4 are represented by hydrogen or deuterium.
In Formula 3-1, Y21's and Y22's may each independently be a hydrogen atom or a deuterium atom.
In Formula 3-1, p is an integer of 0 to 4, and q is an integer of 0 to 5. When each of p and q is 0, the fused polycyclic compound of an embodiment may not be substituted with each of Y21 and Y22 (e.g., not substituted with a deuterium atom). The case where each of p is 4 and each of q is 5 and Y21's and Y22's each are hydrogen atoms may be the same as the case where each of p and q is 0. When each of p and q is an integer of 2 or more, a plurality of Y21's and Y22's may each be the same or at least one from among the plurality of Y21's and Y22's may be different from the others.
In Formula 3-1, the same as described in Formula 3 may be applied to “-*.”
The fused polycyclic compound of an embodiment may be any one from among the compounds represented by Compound Group 1. The light emitting device ED of an embodiment may include at least one fused polycyclic compound from among the compounds represented by Compound Group 1 in the emission layer EML.
In the example compounds presented in Compound Group 1, “D” refers to a deuterium atom and “Ph” refers to a phenyl group.
The fused polycyclic compound represented by Formula 1 according to an embodiment includes the first substituent and the second substituent, each of which is a steric hindrance substituent, and thus may achieve high luminous efficiency and long service life.
The fused polycyclic compound of an embodiment has a structure in which the first to third aromatic rings are fused by one boron atom, the first heteroatom, and the second heteroatom, and necessarily includes, as a substituent, the first substituent and the second substituent which are bonded to the first to third aromatic rings, or linked to the fused structure via a phenylene linker. The first substituent and the second substituent include a triphenyl silane moiety, and include a phenyl group (e.g., a fourth phenyl group) substituted at the meta-position of one of the three phenyl groups of the triphenyl silane moiety with respect to the silicon atom of the triphenyl silane moiety. The fused polycyclic compound of an embodiment having such a structure may effectively maintain a trigonal planar structure of the boron atom through the steric hindrance effect due to the first substituent and the second substituent. The boron atom may have electron deficiency characteristics by an empty p-orbital, thereby may form a bond with other nucleophiles, and thus be changed into a tetrahedral structure, which may cause deterioration of the device. According to the present disclosure, the fused polycyclic compound represented by Formula 1 includes the first substituent and the second substituent having the steric hindrance structure, thereby may effectively protect the empty p-orbital of the boron atom, and thus may prevent or reduce the deterioration phenomenon due to the structural change.
In some embodiments, the fused polycyclic compound of an embodiment may have an increase in the luminous efficiency because the intermolecular interaction may be suppressed or reduced by the introduction of the first substituent and the second substituent, thereby controlling the formation of excimer or exciplex. The fused polycyclic compound represented by Formula 1 of an embodiment includes the first and second substituents, and thus the dihedral angle between the plane containing the fused ring core structure having the boron atom at the center and the plane containing the first substituent and the second substituent may be increased. For example, a first dihedral angle between a first plane containing the first to third aromatic rings and a second plane containing the first substituent and the second substituent may be increased. Thus, the intermolecular distance increases so that there is an effect of reducing the Dexter energy transfer. The Dexter energy transfer is a phenomenon, in which a triplet exciton moves between molecules, and increases when the intermolecular distance is short (e.g., reduced), and may become a factor that increases a quenching phenomenon due to the increase of triplet concentration. According to the present disclosure, the fused polycyclic compound of an embodiment has an increase in the distance between adjacent molecules due to the large steric hindrance structure to thereby suppress or reduce the Dexter energy transfer, and thus may suppress or reduce the deterioration of service life due to the increase of triplet concentration. Therefore, when the fused polycyclic compound of an embodiment is applied to the emission layer EML of the light emitting device ED, the luminous efficiency may be increased and the device service life may also be improved. The fused polycyclic compound of an embodiment may have a decrease in the difference (ΔEst) between a lowest triplet exciton energy level (T1 level) and a lowest singlet exciton energy level (S1 level) by the structure above, and accordingly, when the fused polycyclic compound is utilized as a material for emitting delayed fluorescence, luminous efficiency of the light emitting device may be improved.
In some embodiments, the fused polycyclic compound of an embodiment may be included in the emission layer EML. The fused polycyclic compound of an embodiment may be included as a dopant material in the emission layer EML. The fused polycyclic compound of an embodiment may be a thermally activated delayed fluorescence material. The fused polycyclic compound of an embodiment may be utilized as a thermally activated delayed fluorescence dopant. For example, in the light emitting device ED of an embodiment, the emission layer EML may include, as a thermally activated delayed fluorescence dopant, at least one from among the fused polycyclic compounds represented by Compound Group 1 as described above. However, a usage of the fused polycyclic compound of an embodiment is not limited thereto.
In an embodiment, the emission layer EML may include a plurality of compounds. The emission layer EML of an embodiment may include the fused polycyclic compound represented by Formula 1, i.e., the first compound, and at least one of the second compound represented by Formula H-1, the third compound represented by Formula H-2, or the fourth compound represented by Formula D-1:
In an embodiment, the second compound may be utilized as a hole transporting host material of the emission layer EML.
In Formula H-1, L1 may be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. For example, L1 may be a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the embodiment of the present disclosure is not limited thereto.
In Formula H-1, Ar1 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ar1 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted biphenyl group, etc., but the embodiment of the present disclosure is not limited thereto.
In Formula H-1, R31 and R32 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In some embodiments, each of R31 and R32 may be bonded to an adjacent group to form a ring. For example, R31 and R32 may each independently be a hydrogen atom or a deuterium atom.
In Formula H-1, n31 and n32 may each independently be an integer of 0 to 4. When each of n31 and n32 is 0, the fused polycyclic compound of an embodiment may not be substituted with each of R31 and R32. The case where each of n31 and n32 is 4 and R31's and R32's are each hydrogen atoms may be the same as the case where each of n31 and n32 is 0. When each of n31 and n32 is an integer of 2 or more, a plurality of R31's and R32's may each be the same or at least one from among the plurality of R31's and R32's may be different from the others.
In an embodiment, the second compound represented by Formula 2 may be represented by any one from among the compounds represented by Compound Group 2. The emission layer EML may include at least one from among the compounds represented by Compound Group 2 as a hole transporting host material.
In example compounds presented in Compound Group 2, “D” may refer to a deuterium atom, and “Ph” may refer to a substituted or unsubstituted phenyl group. For example, in example compounds presented in Compound Group 2, “Ph” may refer to an unsubstituted phenyl group.
In an embodiment, the emission layer EML may include the third compound represented by Formula H-2. For example, the third compound may be utilized as an electron transport host material of the emission layer EML.
In Formula H-2, Z1 to Z3 may each independently be N or CR36, and at least one from among Z1 to Z3 may be N.
In Formula H-2, R33 to R36 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In some embodiments, each of R33 to R36 may be bonded to an adjacent group to form a ring. For example, R33 to R36 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, etc., but the embodiment of the present disclosure is not limited thereto.
In an embodiment, the third compound represented by Formula H-2 may be represented by any one from among the compounds represented by Compound Group 3. The emission layer EML may include at least one from among the compounds represented by Compound Group 3 as an electron transporting host material.
In example compounds presented in Compound Group 3, “D” may refer to a deuterium atom, and “Ph” may refer to an unsubstituted phenyl group.
The emission layer EML may include the second compound and the third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, an exciplex may be formed by the hole transport host and the electron transport host. In this case, a triplet energy of the exciplex formed by the hole transporting host and the electron transporting host may correspond to the difference between a lowest unoccupied molecular orbital (LUMO) energy level of the electron transporting host and a highest occupied molecular orbital (HOMO) energy level of the hole transporting host.
For example, the absolute value of the triplet energy (T1) of the exciplex formed by the hole transporting host and the electron transporting host may be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy of the exciplex may be a value smaller than an energy gap of each host material. The exciplex may have a triplet energy of about 3.0 eV or less that is an energy gap between the hole transporting host and the electron transporting host.
In an embodiment, the emission layer EML may include a fourth compound in addition to the first compound to the third compound as described above. The fourth compound may be utilized as a phosphorescent sensitizer of the emission layer EML. The energy may be transferred from the fourth compound to the first compound, thereby emitting light.
For example, the emission layer EML may include, as the fourth compound, an organometallic complex containing platinum (Pt) as a central metal atom and ligands linked to the central metal atom. The emission layer EML in the light emitting device ED of an embodiment may include, as the fourth compound, a compound represented by Formula D-1:
In Formula D-1, Q1 to Q4 may each independently be C or N.
In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms.
In Formula D-1, L11 to L13 may each independently be a direct linkage,
a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In L11 to L13, “-*” refers to a part linked to C1 to C4.
In Formula D-1, b1 to b3 may each independently be 0 or 1. When b1 is 0, C1 and C2 may not be linked to each other. When b2 is 0, C2 and C3 may not be linked to each other. When b3 is 0, C3 and C4 may not be linked to each other.
In Formula D-1, R41 to R46 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In some embodiments, each of R41 to R46 may be bonded to an adjacent group to form a ring. In some embodiments, R41 to R46 may each independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.
In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, when each of d1 to d4 is 0, the fused polycyclic compound of an embodiment may not be substituted with each of R41 to R44. The case where each of d1 to d4 is 4 and R41's to R44′ are each hydrogen atoms may be the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or more, a plurality of R41's to R44's may each be the same or at least one from among the plurality of R41's to R44's may be different from the others.
In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle represented by any one from among Formulae C-1 to C-4:
In Formulae C-1 to C-4, P1 may be
In some embodiments, in Formulae C-1 to C-4,
corresponds to a part linked to Pt that is a central metal atom, and “-*” corresponds to a part linked to a neighboring cyclic group (C1 to C4) or a linker (L11 to L14).
The emission layer EML of an embodiment may include the first compound, and at least one of the second to fourth compounds. For example, the emission layer EML may include the first compound, the second compound, and the third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and the energy may be transferred from the exciplex to the first compound, thereby emitting light.
In some embodiments, the emission layer EML may include the first compound, the second compound, the third compound, and the fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and the energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In an embodiment, the fourth compound may be a sensitizer. The fourth compound included in the emission layer EML in the light emitting device ED of an embodiment may serve as a sensitizer to deliver energy from the host to the first compound that is a light emitting dopant. For example, the fourth compound serving as an auxiliary dopant accelerates energy delivery to the first compound that is a light emitting dopant, thereby increasing the emission ratio (e.g., emission efficiency) of the first compound. Therefore, the emission layer EML of an embodiment may improve luminous efficiency. In some embodiments, when the energy delivery to the first compound is increased, an exciton formed in the emission layer EML is not accumulated inside the emission layer EML and light is emitted rapidly, and thus deterioration of the element may be reduced. Therefore, the service life of the light emitting device ED of an embodiment may increase.
The light emitting device ED of an embodiment may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include the combination of two host materials and two dopant materials. In the light emitting device ED of an embodiment, the emission layer EML may concurrently (e.g., simultaneously) include two different hosts, the first compound that emits a delayed fluorescence, and the fourth compound including an organometallic complex, thereby exhibiting excellent or suitable luminous efficiency characteristics.
In an embodiment, the fourth compound represented by Formula D-1 may represented at least one from among the compounds represented by Compound Group 4. The emission layer EML may include at least one from among the compounds represented by Compound Group 4 as a sensitizer material.
In some embodiments, the light emitting device ED of an embodiment may include a plurality of emission layers. The plurality of emission layers may be sequentially stacked and provided, and for example, the light emitting device ED including the plurality of emission layers may be to emit white light. The light emitting device including the plurality of emission layers may be a light emitting device having a tandem structure. When the light emitting device ED includes a plurality of emission layers, at least one emission layer EML may include the first compound represented by Formula 1 of an embodiment. In some embodiments, when the light emitting device ED includes the plurality of emission layers, at least one emission layer EML may include all of the first compound, the second compound, the third compound, and the fourth compound as described above.
When the emission layer EML in the light emitting device ED of an embodiment includes all of the first compound, the second compound, and the third compound, with respect to the total weight of the first compound, the second compound, and the third compound, the content (e.g., amount) of the first compound may be about 0.5 wt % to about 3 wt %. When the content (e.g., amount) of the first compound satisfy the above-described proportion, the energy transfer from the second compound and the third compound to the first compound may increase, and thus the luminous efficiency and device service life may increase. However, the embodiment of the present disclosure is not limited thereto.
The contents of the second compound and the third compound in the emission layer EML may be the rest (e.g., balance) excluding the weight of the first compound. For example, the contents of the second compound and the third compound in the emission layer EML may be about 20 wt % to about 90 wt % with respect to the total weight of the first compound, the second compound, and the third compound.
In the total weight of the second compound and the third compound, the weight ratio of the second compound and the third compound may be about 3:7 to about 7:3.
When the contents of the second compound and the third compound satisfy the above-described ratio, a charge balance characteristic in the emission layer EML are improved, and thus the luminous efficiency and device service life may increase. When the contents of the second compound and the third compound deviate from the above-described ratio range, a charge balance in the emission layer EML may be broken, and thus the luminous efficiency may be reduced and the device may be easily deteriorated.
When the first compound, the second compound, and the third compound included in the emission layer EML satisfies the above-described ratio ranges, excellent or suitable luminous efficiency and long service life may be achieved.
In the light emitting device ED of an embodiment, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dehydrobenzanthracene derivative, and/or a triphenylene derivative. For example, the emission layer EML may include the anthracene derivative and/or the pyrene derivative.
In each light emitting device ED of embodiments illustrated in
In Formula E-1, R31 to R40 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring. In some embodiments, R31 to R40 may be bonded to an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.
In Formula E-1, c and d may each independently be an integer of 0 to 5.
Formula E-1 may be represented by any one from among Compound E1 to Compound E19:
In an embodiment, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be utilized as a phosphorescent host material.
In Formula E-2a, a may be an integer of 0 to 10, and L a may be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In some embodiments, when a is an integer of 2 or more, a plurality of La's may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
In some embodiments, in Formula E-2a, A1 to A5 may each independently be N or CRi. Ra to Ri may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring. Ra to Ri may be bonded to an adjacent group to form a hydrocarbon ring or a heterocycle containing N, O, S, etc., as a ring-forming atom.
In some embodiments, in Formula E-2a, two or three (or at least two or three) selected from among A1 to A5 may be N, and the rest (e.g., any remainder thereof) may be CR.
In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group, or a carbazole group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. Lb may be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. b may be an integer of 0 to 10, and when b is an integer of 2 or more, a plurality of Lb's may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
The compound represented by Formula E-2a or Formula E-2b may be represented by any one from among the compounds of Compound Group E-2. However, the compounds listed in Compound Group E-2 are examples, and the compound represented by Formula E-2a or Formula E-2b is not limited to those represented in Compound Group E-2.
The emission layer EML may further include a general material suitable in the art as a host material. For example, the emission layer EML may include, as a host material, at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA), or 1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene (TPBi). However, the embodiment of the present disclosure is not limited thereto, for example, tris(8-hydroxyquinolino)aluminum (Alq3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), hexaphenyl cyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetra siloxane (DPSiO4), etc. may be utilized as a host material.
The emission layer EML may include the compound represented by Formula M-a. The compound represented by Formula M-a may be utilized as a phosphorescent dopant material.
In Formula M-a above, Y1 to Y4 and Z1 to Z4 may each independently be CR1 or N, and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring. In Formula M-a, m is 0 or 1, and n is 2 or 3. In Formula M-a, when m is 0, n is 3, and when m is 1, n is 2.
The compound represented by Formula M-a may be utilized as a phosphorescent dopant.
The compound represented by Formula M-a may be represented by any one from among Compound M-a1 to Compound M-a25. However, Compounds M-a1 to M-a25 are examples, and the compound represented by Formula M-a is not limited to those represented by Compounds M-a1 to M-a25.
The emission layer EML may include a compound represented by any one from among Formula F-a to Formula F-c. The compound represented by Formula F-a or Formula F-c may be utilized as a fluorescence dopant material.
In Formula F-a above, two groups selected from among Ra to R may each independently be substituted with *—NAr1Ar2. The others (e.g., any remainder thereof), which are not substituted with *—NAr1Ar2 from among Ra to R may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In *—NAr1Ar2, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 or Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.
In Formula F-b above, R a and Rb may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring.
In Formula F-b above, Ar1 to Ar4 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
In Formula F-b above, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms. At least one from among Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring-forming atom.
In Formula F-b, the number of rings represented by U and V may each independently be 0 or 1. For example, in Formula F-b, when the number of U or V is 1, one ring indicated by U or V forms a fused ring at the designated part (e.g., at the part indicated by U or V), and when the number of U or V is 0, a ring does not exist at the part designated by U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring having a fluorene core in Formula F-b may be a cyclic compound having four rings. In some embodiments, when each number of U and V is 0, the fused ring in Formula F-b may be a cyclic compound having three rings. In some embodiments, when each number of U and V is 1, the fused ring having a fluorene core in Formula F-b may be a cyclic compound having five rings.
In Formula F-c, A1 and A2 may each independently be O, S, Se, or NRm, and Rm may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R1 to R11 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring.
In Formula F-c, A1 and A2 may each independently be bonded to substituents of an adjacent ring to form a condensed ring. For example, when A1 and A2 may each independently be NRm, A1 may be bonded to R4 or R5 to form a ring. In some embodiments, A2 may be bonded to R7 or R8 to form a ring.
In an embodiment, the emission layer EML may further include, as a suitable dopant material, one or more styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenz enamine (N-BDAVBi), and/or 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl]vinylpiphenyl (DPAVBi)), perylene and the derivatives thereof (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and the derivatives thereof (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, and/or 1,4-bis(N,N-diphenylamino)pyrene), etc.
The emission layer EML may further include a suitable phosphorescence dopant material. For example, a metal complex containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and/or thulium (Tm) may be utilized as a phosphorescent dopant. For example, iridium(III) bis(4,6-difluorophenylpyridinato-N,C2′)picolinate (Flrpic), bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium (III) (Fir6), and/or platinum octaethyl porphyrin (PtOEP) may be utilized as a phosphorescent dopant. However, the embodiment of the present disclosure is not limited thereto.
The emission layer EML may include a quantum dot material. The core of the quantum dot may be selected from among a Group 11-VI compound, a Group III-VI compound, a Group I-III-VI compound, a Group III-V compound, a Group III-II-V compound, a Group IV-VI compound, a Group IV element, a Group IV compound, and a combination thereof.
The Group 11-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and a mixture thereof, a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and a mixture thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and a mixture thereof.
The Group III-VI compound may include a binary compound such as In2S3 or In2Se3, a ternary compound such as InGaS3 and/or InGaSe3, or any combination thereof.
The Group I-III-VI compound may be selected from a ternary compound selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2 CuGaO2, AgGaO2, AgAlO2, and a mixture thereof, and/or a quaternary compound such as AgInGaS2 and/or CuInGaS2.
The Group III-V compound may be selected from the group consisting of a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and a mixture thereof, a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and a mixture thereof, and a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and a mixture thereof. In some embodiments, the Group III-V compound may further include a Group II metal. For example, InZnP, etc., may be selected as a Group III-II-V compound.
The Group IV-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and a mixture thereof, a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and a mixture thereof, and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and a mixture thereof. The Group IV element may be selected from the group consisting of Si, Ge, and a mixture thereof. The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and a mixture thereof.
In this case, the binary compound, the ternary compound, and/or the quaternary compound may be present in a particle with a substantially uniform concentration distribution, or may be present in the same particle with a partially different concentration distribution. In some embodiments, the quantum dot may have a core/shell structure in which one quantum dot surrounds the other quantum dot. The core/shell structure may have a concentration gradient in which the concentration of elements present in the shell decreases toward the core.
In some embodiments, the quantum dot may have the above-described core/shell structure including a core containing nanocrystals and a shell around (e.g., surrounding) the core. The shell of the quantum dot may serve as a protection layer to prevent or reduce the chemical deformation of the core to maintain semiconductor properties, and/or a charging layer to impart electrophoresis properties to the quantum dot. The shell may be a single layer or a multilayer. An example of the shell of the quantum dot may include a metal or non-metal oxide, a semiconductor compound, or a combination thereof.
For example, the metal or non-metal oxide may be a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO, or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4, but the embodiment of the present disclosure is not limited thereto.
Also, examples of the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiment of the present disclosure is not limited thereto.
The quantum dot may have a full width of half maximum (FWHM) of a light emitting wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and color purity or color reproducibility may be improved in the above ranges. In some embodiments, light emitted through such a quantum dot is emitted in all directions, and thus a wide viewing angle may be improved.
In some embodiments, although the form of the quantum dot is not particularly limited as long as it is a form commonly utilized in the art, more specifically, the quantum dot in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate particles, etc., may be utilized.
A quantum dot may control the color of emitted light according to the particle size thereof and thus the quantum dot may have one or more suitable light emission colors such as green, red, etc.
In each light emitting device ED of embodiments illustrated in
The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.
For example, the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region ETR may have a single layer structure formed of a plurality of different materials, or may have a structure in which an electron transport layer ETL/electron injection layer EIL, a hole blocking layer HBL/electron transport layer ETL/electron injection layer EIL are stacked in the respective stated order from the emission layer EML, but the embodiment of the present disclosure is not limited thereto. The electron transport region ETR may have a thickness, for example, from about 1,000 Å to about 1,500 Å.
The electron transport region ETR may be formed by utilizing one or more suitable methods such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
The electron transport region ETR may include a compound represented by Formula ET-1:
In Formula ET-1, at least one from among X1 to X3 may be N, and the rest (e.g., any remainder thereof) may be CRa. Ra may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
In Formula ET-1, a to c may each independently be an integer of 0 to 10. In Formula ET-1, L1 to L3 may each independently be a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In some embodiments, when a to c are an integer of 2 or more, L1 to L3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
The electron transport region ETR may include an anthracene-based compound. However, the embodiment of the present disclosure is not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinolinato)aluminum (Alq3), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1-biphenyl-4-olato)aluminum (BAlq), berylliumbis(benzoquinolin-10-olate (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), or a mixture thereof.
The electron transport region ETR may include at least one from among Compound ET1 to Compound ET36:
In some embodiments, the electron transport regions ETR may include a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, and/or KI, a lanthanide metal such as Yb, or a co-deposited material of the metal halide and the lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc., as a co-deposited material. In some embodiments, the electron transport region ETR may be formed utilizing a metal oxide such as Li2O and/or BaO, and/or 8-hydroxyl-lithium quinolate (Liq), etc., but the embodiment of the present disclosure is not limited thereto. The electron transport region ETR may also be formed of a mixture material of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having an energy band gap of about 4 eV or more. For example, the organometallic salt may include, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, and/or a metal stearate.
The electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), or 4,7-diphenyl-1,10-phenanthroline (Bphen) in addition to the above-described materials, but the embodiment of the present disclosure is not limited thereto.
The electron transport region ETR may include the above-described compounds of the hole transport region in at least one of the electron injection layer EIL, the electron transport layer ETL, or the hole blocking layer HBL.
When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer ETL satisfies the aforementioned range, satisfactory electron transport characteristics may be obtained without a substantial increase in driving voltage.
When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer EIL satisfies the above-described range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment of the present disclosure is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.
The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is the transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.
When the second electrode EL2 is the transflective electrode or the reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, Yb, W, or a compound or mixture thereof (e.g., AgMg, AgYb, or MgAg). In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above-described materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include one or more of the above-described metal materials, combinations of at least two metal materials of the above-described metal materials, oxides of the above-described metal materials, and/or the like.
The second electrode EL2 may be connected with an auxiliary electrode. When the second electrode EL2 is connected with the auxiliary electrode, the resistance of the second electrode EL2 may be decreased.
In some embodiments, a capping layer CPL may further be disposed on the second electrode EL2 of the light emitting device ED of an embodiment. The capping layer CPL may include a multilayer or a single layer.
In an embodiment, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL contains an inorganic material, the inorganic material may include an alkaline metal compound (for example, LiF), an alkaline earth metal compound (for example, MgF2), SiON, SiNx, SiOy, etc. For example, when the capping layer CPL includes an organic material, the organic material may include a-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4′,N4′-tetra(biphenyl-4-yl)biphenyl-4,4′-diamine (TPD15), 4,4′,4″-tris(carbazol sol-9-yl)triphenylamine (TCTA), etc., an epoxy resin, and/or acrylate such as methacrylate. However, the embodiment of the present disclosure is not limited thereto, and the capping layer CPL may include at least one from among Compounds P1 to P5:
In some embodiments, the refractive index of the capping layer CPL may be about 1.6 or more. For example, the refractive index of the capping layer CPL may be 1.6 or more with respect to light in a wavelength range of about 550 nm to about 660 nm.
Each of
Referring to
In an embodiment illustrated in
The light emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In some embodiments, the structures of the light emitting devices of
The emission layer EML of the light emitting device ED included in the display apparatus DD-a according to an embodiment may include the above-described fused polycyclic compound of an embodiment.
Referring to
The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light conversion body. The light conversion body may be a quantum dot, a phosphor, and/or the like. The light conversion body may transform the wavelength of light provided and then emit (e.g., emit light of a different color). For example, the light control layer CCL may be a layer containing the quantum dot or a layer containing the phosphor.
The light control layer CCL may include a plurality of light control parts CCP1, CCP2 and CCP3. The light control parts CCP1, CCP2, and CCP3 may be spaced apart from each other.
Referring to
The light control layer CCL may include a first light control part CCP1 containing a first quantum dot QD1 which converts the first color light provided from the light emitting device ED into a second color light, a second light control part CCP2 containing a second quantum dot QD2 which converts the first color light into a third color light, and a third light control part CCP3 which transmits the first color light.
In an embodiment, the first light control part CCP1 may provide red light that is the second color light, and the second light control part CCP2 may provide green light that is the third color light. The third light control part CCP3 may provide blue light by transmitting the blue light that is the first color light provided from the light emitting device ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same as described above may be applied with respect to the quantum dots QD1 and QD2.
In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include the first quantum dot QD1 and the scatterer SP, the second light control part CCP2 may include the second quantum dot QD2 and the scatterer SP, and the third light control part CCP3 may not include (e.g., may exclude) any quantum dot but may include the scatterer SP.
The scatterer SP may be inorganic particles. For example, the scatterer SP may include at least one of TiO2, ZnO, Al2O3, SiO2, or hollow sphere silica. The scatterer SP may include any one from among TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica, or may be a mixture of at least two materials selected from among TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica.
The first light control part CCP1, the second light control part CCP2, and the third light control part CCP3 each may include base resins BR1, BR2, and BR3 in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed. In an embodiment, the first light control part CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in a first base resin BR1, the second light control part CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in a second base resin BR2, and the third light control part CCP3 may include the scatterer SP dispersed in a third base resin BR3. The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be formed of one or more suitable resin compositions, which may be generally referred to as a binder. For example, the base resins BR1, BR2, and BR3 may be one or more acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In an embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.
The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may serve to prevent or reduce the penetration of moisture and/or oxygen (hereinafter, referred to as ‘moisture/oxygen’). The barrier layer BFL1 may be disposed on the light control parts CCP1, CCP2, and CCP3 to block or reduce the light control parts CCP1, CCP2 and CCP3 from being exposed to moisture/oxygen. In some embodiments, the barrier layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. In some embodiments, a barrier layer BFL2 may be provided between the light control parts CCP1, CCP2, and CCP3 and filters CF1, CF2, and CF3.
The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers BFL1 and BFL2 may include a silicon nitride, an aluminum nitride, a zirconium nitride, a titanium nitride, a hafnium nitride, a tantalum nitride, a silicon oxide, an aluminum oxide, a titanium oxide, a tin oxide, a cerium oxide, a silicon oxynitride, a metal thin film which secures a transmittance, etc. In some embodiments, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.
In the display apparatus DD-a of an embodiment, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the light control layer CCL. In this case, the barrier layer BFL2 may not be provided.
The color filter layer CFL may include a light shielding part BM and color filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit the second color light, a second filter CF2 configured to transmit the third color light, and a third filter CF3 configured to transmit the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 each may include a polymeric photosensitive resin and a pigment and/or dye. The first filter CF1 may include a red pigment and/or dye, the second filter CF2 may include a green pigment and/or dye, and the third filter CF3 may include a blue pigment and/or dye. In some embodiments, the embodiment of the present disclosure is not limited thereto, and the third filter CF3 may not include (e.g., may exclude) a pigment or dye (e.g., may exclude any pigment or dye). The third filter CF3 may include a polymeric photosensitive resin and may not include (e.g., may exclude) a pigment or dye (e.g., may exclude any pigment or dye). The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
Furthermore, in an embodiment, the first filter CF1 and the second filter CF2 may be a yellow filter. The first filter CF1 and the second filter CF2 may not be separated but be provided as one filter.
The light shielding part BM may be a black matrix. The light shielding part BM may include an organic light shielding material and/or an inorganic light shielding material containing a black pigment and/or dye. The light shielding part BM may prevent or reduce light leakage, and may separate boundaries between the adjacent filters CF1, CF2, and CF3. In some embodiments, in an embodiment, the light shielding part BM may be formed of a blue filter.
The first to third filters CF1, CF2, and CF3 may be disposed corresponding to the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B, respectively.
A base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member which provides a base surface on which the color filter layer CFL, the light control layer CCL, and/or the like are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment of the present disclosure is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the configuration illustrated, in an embodiment, the base substrate BL may not be provided.
For example, the light emitting device ED-BT included in the display apparatus DD-TD of an embodiment may be a light emitting device having a tandem structure and including a plurality of emission layers.
In an embodiment illustrated in
Charge generation layers CGL1 and CGL2 may be respectively disposed between two of the neighboring light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include a p-type or kind charge generation layer and/or an n-type or kind charge generation layer.
At least one from among the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display apparatus DD-TD of an embodiment may contain the above-described fused polycyclic compound of an embodiment. For example, at least one from among the plurality of emission layers included in the light emitting device ED-BT may include the fused polycyclic compound of an embodiment.
Referring to
The first light emitting device ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light emitting device ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In some embodiments, the third light emitting device ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. An emission auxiliary part OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
The emission auxiliary part OG may include a single layer or a multilayer. The emission auxiliary part OG may include a charge generation layer. More specifically, the emission auxiliary part OG may include an electron transport region, a charge generation layer, and a hole transport region that are sequentially stacked. The emission auxiliary part OG may be provided as a common layer in the whole of the first to third light emitting devices ED-1, ED-2, and ED-3. However, the embodiment of the present disclosure is not limited thereto, and the emission auxiliary part OG may be patterned and provided within the openings OH defined in the pixel defining film PDL.
The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may be disposed between the electron transport region ETR and the emission auxiliary part OG. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may be disposed between the emission auxiliary part OG and the hole transport region HTR.
For example, the first light emitting device ED-1 may include the first electrode EL1, the hole transport region HTR, the second red emission layer EML-R2, the emission auxiliary part OG, the first red emission layer EML-R1, the electron transport region ETR, and the second electrode EL2 that are sequentially stacked. The second light emitting device ED-2 may include the first electrode EL1, the hole transport region HTR, the second green emission layer EML-G2, the emission auxiliary part OG, the first green emission layer EML-G1, the electron transport region ETR, and the second electrode EL2 that are sequentially stacked. The third light emitting device ED-3 may include the first electrode EL1, the hole transport region HTR, the second blue emission layer EML-B2, the emission auxiliary part OG, the first blue emission layer EML-B1, the electron transport region ETR, and the second electrode EL2 that are sequentially stacked.
In some embodiments, an optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and control reflected light in the display panel DP due to external light. Unlike the configuration illustrated, the optical auxiliary layer PL in the display apparatus according to an embodiment may not be provided.
At least one emission layer included in the display apparatus DD-b of an embodiment illustrated in
Unlike
The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type or kind charge generation layer and/or an n-type or kind charge generation layer.
At least one from among the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display apparatus DD-c of an embodiment may contain the above-described fused polycyclic compound of an embodiment. For example, in an embodiment, at least one from among the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may include the above described fused polycyclic compound of an embodiment.
Hereinafter, with reference to Examples and Comparative Examples, a condensed polycyclic according to an embodiment of the present disclosure and a luminescence device of an embodiment of the present disclosure will be described in more detail. In addition, Examples described below are only illustrations to assist the understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.
First, a synthetic method of a fused polycyclic compound according to the current embodiment will be described in more detail by illustrating synthetic methods of Compounds 12, 43, 64, 78, and 118. In addition, the synthetic methods of the fused polycyclic compounds as described below are only examples, and the synthetic method of the fused polycyclic compound according to an embodiment of the present disclosure is not limited to the following examples.
Fused Polycyclic Compound 12 according to an example may be synthesized by, for example, the reaction below:
1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-(3-bromophenyl)-[1,1′:3′,1″-terphenyl]-4′-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (1.5 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 80° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized by column chromatography (dichloromethane:n-hexane) to obtain Intermediate 12-1 (yield: 65%).
Intermediate 12-1 (1 eq), N-(3-chlorophenyl)-[1,1′:3′,1″-terphenyl]-5-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 90° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized by column chromatography (dichloromethane:n-hexane) to obtain Intermediate 11-2 (yield: 63%).
Intermediate 12-2 (1 eq) was dissolved in ortho dichlorobenezene, and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr3 (2.5 eq) dissolved in ortho dichlorobenezene was slowly injected thereto. After the injection was completed, the temperature was elevated to about 180° C., and the mixture was stirred for about 20 hours. After the mixture was cooled to about 0° C., triethylamine was slowly dropped to the flask until heating stopped to quench the reaction, and then hexane was added to the flask to extract the solids. The extracted solids were obtained by filtration. The obtained solids were purified with silica filtration, and then purified again through recrystallization in methylene chloride/hexane to obtain Intermediate 12-3. Thereafter, Compound 34 was finally purified by column chromatography (dichloromethane:n-hexane) (yield: 13%).
Intermediate 12-3 (1 eq), (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis([1,1′-biphenyl]-3-yldi phenylsilane) (1 eq), tetrakis(triphenylphosphine)-palladium(0) (0.05 eq), and potassium carbonate (3 eq) were dissolved in tetrahydrofuran:distilled water (3:1), and then the resultant mixture was stirred at about 80° C. for about 24 hours. After being cooled, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized by column chromatography (dichloromethane:n-hexane) to obtain Intermediate 12-4 (yield: 52%).
Intermediate 12-4 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.3 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Compound 12 (yield: 46%). Then, the resulting product was further purified by sublimation purification to obtain final purity.
Fused Polycyclic Compound 43 according to an example may be synthesized, for example, by the reaction below: Synthesis of Intermediate 43-1
3,5-dibromophenol (1 eq), 1-chloro-3-fluorobenzene (2 eq), and potassium phosphate tribasic (4 eq) were dissolved in N,N-dimethylformamide anhydrous, and then the resultant mixture was stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the N,N-dimethylformamide was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 43-1 (yield: 67%).
Intermediate 43-1 (1 eq), N-([1,1′-biphenyl]-4-yl)-5-(tert-butyl)-[1,1′-biphenyl]-2-amine (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 43-2 (yield: 64%).
Intermediate 43-2 (1 eq) was dissolved in ortho dichlorobenezene, and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr3 (2.5 eq) dissolved in ortho dichlorobenezene was slowly injected thereto. After the injection was completed, the temperature was elevated to about 180° C., and the mixture was stirred for about 20 hours. After cooling to about 0° C., triethylamine was slowly dropped to the flask until heating stopped to quench the reaction, and then hexane was added to the flask to extract the solids. The extracted solids were obtained by filtration. The obtained solids were purified with silica filtration, and then purified again through recrystallization in methylene chloride/hexane to obtain Intermediate 43-3.
Intermediate 43-3 (1 eq), (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis([1,1′-biphenyl]-3-yldi phenylsilane) (1.1 eq), tetrakis(triphenylphosphine) palladium(0) (0.05 eq), and potassium carbonate (3 eq) were dissolved in tetrahydrofuran/distilled water (3:1), and then the resultant mixture was stirred in a nitrogen atmosphere at about 80° C. for about 24 hours. After being cooled, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 43-4 (yield: 56%).
Intermediate 43-4 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (3 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized by column chromatography (dichloromethane:n-hexane) to obtain Compound 43 (yield: 61%). Then, the resulting product was further purified by sublimation purification to obtain final purity. The compound was identified through FAB/MS (MS[M+H]+=1284).
Fused Polycyclic Compound 64 according to an example may be synthesized by, for example, the reaction below:
1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-(4-bromophenyl)-[1,1′:3′,1″-terphenyl]-4′-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 100° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 64-1 (yield: 71%).
Intermediate 64-1 (1 eq), N-(3-chlorophenyl)[1,1′:3′,1″-terphenyl]-2,3,4,5,6-d5-5′-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 64-2 (yield: 43%).
Intermediate 64-2 (1 eq) was dissolved in ortho dichlorobenezene, and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr3 (2.5 eq) dissolved in ortho dichlorobenezene was slowly injected thereto. After the injection was completed, the temperature was elevated to about 180° C., and the mixture was stirred for about 20 hours. After the mixture was cooled to about 0° C., triethylamine was slowly dropped to the flask until heating stopped to quench the reaction, and then hexane was added to the flask to extract the solids. The extracted solids were obtained by filtration. The obtained solids were purified with silica filtration, and then purified again through recrystallization in methylene chloride/hexane to obtain Intermediate 64-3.
Intermediate 64-3 (1 eq), (5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis([1,1′-biphenyl]-3-yldi phenylsilane) (1.1 eq), tetrakis(triphenylphosphine) palladium(0) (0.05 eq), and potassium carbonate (3 eq) were dissolved in tetrahydrofuran/distilled water (3:1), and then the resultant mixture was stirred in a nitrogen atmosphere at about 80° C. for about 24 hours. After being cooled, the resulting product was washed three times with ethyl acetate and water, and then an organic layer was obtained. The obtained organic layer was dried with MgSO4, and then dried at reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 64-4 (yield: 58%).
Intermediate 64-4 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Compound 64 (yield: 66%). Then, the resulting product was further purified by sublimation purification to obtain final purity. The compound was identified through FAB/MS (MS[M+H]+=1704).
Fused Polycyclic Compound 78 according to an example may be synthesized, for example, by the reaction below:
1,3-dibromo-5-fluorobenzene (1 eq), 2,7-di-tert-butyl-9H-carbazole (2 eq), and potassium phosphate tribasic (3 eq) were dissolved in N,N-dimethylformamide anhydrous, and then the resultant mixture was stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the N,N-dimethylformamide was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 78-1 (yield: 72%).
Intermediate 78-1 (1 eq), N-(3-bromophenyl)-[1,1′-biphenyl]-2-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 78-2 (yield: 62%).
Intermediate 78-2 (1 eq), N-(4-bromophenyl)-[1,1′-biphenyl]-2-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 78-3 (yield: 57%).
Intermediate 78-3 (1 eq) was dissolved in ortho dichlorobenezene, and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr3 (2.5 eq) dissolved in ortho dichlorobenezene was slowly injected thereto. After the injection was completed, the temperature was elevated to about 180° C., and the mixture was stirred for about 20 hours. After the mixture was cooled to about 0° C., triethylamine was slowly dropped to the flask until heating stopped to quench the reaction, and then hexane was added to the flask to extract the solids. The extracted solids were obtained by filtration. The obtained solids were purified with silica filtration, and then purified again through recrystallization in methylene chloride/hexane to obtain Intermediate 78-4.
Intermediate 78-4 (1 eq) was dissolved in diethyl ether, and the flask was cooled to about −78° C. in a nitrogen atmosphere, and then N-butyllithium 2.5 M hexanes (1 eq) were slowly injected thereto. After the injection was completed, the mixture was stirred for about 2 hours, and [1,1′-biphenyl]-3-ylchlorodiphenylsilane dissolved in diethyl ether was slowly dropped and injected thereto. After the injection was completed, the mixture was stirred at room temperature for about 24 hours, extracted with methylene chloride, and purified by silica filtration. Again, the resulting product was finally purified (dichloromethane:n-hexane) by column chromatography (yield: 54%).
Intermediate 78-5 (1 eq) was dissolved in diethyl ether, and the flask was cooled to about −78° C. in a nitrogen atmosphere, and then N-butyllithium 2.5 M hexanes (1 eq) were slowly injected thereto. After the injection was completed, the mixture was stirred for about 2 hours, and ([1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)chlorodiphenylsilane dissolved in diethyl ether was slowly dropped and injected thereto. After the injection was completed, the mixture was stirred at room temperature for about 24 hours, extracted with methylene chloride, and purified by silica filtration. Again, the resulting product was finally purified (dichloromethane:n-hexane) by column chromatography (yield: 51%). Then, the resulting product was further purified by sublimation purification to obtain final purity. The compound was identified as Compound 78 through FAB/MS (MS[M+H]+=1524).
Fused Polycyclic Compound 118 according to an example may be synthesized, for example, by the reaction below:
1,3-dibromo-5-chlorobenzene (1 eq), N-(3-bromophenyl)-[1,1′-biphenyl]-2-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 118-1 (yield: 60%).
Intermediate 118-1 (1 eq), 3′-(tert-butyl)-[1,1′-biphenyl]-3-thiol (1 eq), Tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.10 eq), and sodium tert-butoxide (2 eq) were dissolved in o-xylene, and then the resultant mixture was stirred in a nitrogen atmosphere at about 95° C. for about 12 hours. After being cooled, the resultant mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with ethyl acetate and water to obtain the organic layers. The obtained organic layers were dried over MgSO4, and then dried under reduced pressure. The resulting product was purified and recrystallized (dichloromethane:n-hexane) by column chromatography to obtain Intermediate 118-2 (yield: 62%).
Intermediate 118-2 (1 eq) was dissolved in ortho dichlorobenezene, and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr3 (2.5 eq) dissolved in ortho dichlorobenezene was slowly injected thereto. After the injection was completed, the temperature was elevated to about 180° C., and the mixture was stirred for about 20 hours. After the mixture was cooled to about 0° C., triethylamine was slowly dropped to the flask until heating stopped to quench the reaction, and then hexane was added to the flask to extract the solids. The extracted solids were obtained by filtration. The obtained solids were purified with silica filtration, and then purified again through recrystallization in methylene chloride/hexane to obtain Intermediate 118-3.
Intermediate 118-3 (1 eq) was dissolved in diethyl ether, and the flask was cooled to about −78° C. in a nitrogen atmosphere, and then N-butyllithium 2.5 M hexanes (1 eq) were slowly injected thereto. After the injection was completed, the mixture was stirred for about 2 hours, and ([1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)chlorodiphenylsilane dissolved in diethyl ether was slowly dropped and injected thereto. After the injection was completed, the mixture was stirred at room temperature for about 24 hours, extracted with methylene chloride, and purified by silica filtration. Again, the resulting product was finally purified (dichloromethane:n-hexane) by column chromatography (yield: 68%).
Intermediate 118-4 (1 eq) was dissolved in diethyl ether, and the flask was cooled to about −78° C. in a nitrogen atmosphere, and then N-butyllithium 2.5 M hexanes (1 eq) were slowly injected thereto. After the injection was completed, the mixture was stirred for about 2 hours, and [1,1′-biphenyl]-3-ylchlorodiphenylsilane dissolved in diethyl ether was slowly dropped and injected thereto. After the injection was completed, the mixture was stirred at room temperature for about 24 hours, extracted with methylene chloride, and purified by silica filtration. Again, the resulting product was finally purified (dichloromethane:n-hexane) by column chromatography (yield: 45%). Then, the resulting product was further purified by sublimation purification to obtain final purity. The compound was identified as Compound 18 through FAB/MS (MS[M+H]+=1244).
The light emitting device of an example including the fused polycyclic compound of an example in an emission layer was manufactured as follows. Fused polycyclic compounds of Compounds 12, 43, 64, 78 and 118, which are Example Compounds as described above, were utilized as dopant materials for the emission layers to manufacture the light emitting devices of Examples 1 to 5, respectively. Comparative Examples 1 to 5 correspond to the light emitting devices manufactured by utilizing Comparative Example Compounds C1 to C5 as dopant materials for the emission layers, respectively.
With respect to the light emitting devices of Examples and Comparative Examples, an ITO glass substrate was cut to a size of about 50 mm×50 mm×0.7 mm, washed by ultrasonic waves utilizing isopropyl alcohol and distilled water for about minutes, respectively, and then irradiated with ultraviolet rays for about 30 minutes and cleansed by exposing to ozone, and then installed on a vacuum deposition apparatus. Then, NPD was utilized to form a 300 Å-thick hole injection layer HIL, H-1-2, H-1-3, H-1-4 or H-1-6 was utilized to form a 200 Å-thick hole transport layer HTL, and then CzSi was utilized to form a 100 Å-thick emission auxiliary layer. Then, a host compound in which the first host and the second host according to an embodiment were mixed in an amount of about 1:1, the second dopant, and Example Compound or Comparative Example Compound were co-deposited in a weight ratio of about 85:14:1 to form a 200 Å-thick emission layer EML, and TSPO1 was utilized to form a 200 Å-thick electron transport layer ETL. Next, TPBi, a buffer electron transporting compound, was utilized to form a 300 Å-thick buffer layer, and LiF was utilized to form a 10 Å-thick electron injection layer EIL. Al was then utilized to form a 3,000 Å-thick LiF/Al electrode as a second electrode EL2. Then, on the upper portion of the second electrode EL2, P4 was utilized to form a 700 Å-thick capping layer. Each layer was formed by a vacuum deposition method. HT1, HT2, or HT3 from among the compounds in Compound Group 2 as described above was utilized as the first host, ETH72, ETH85, or ETH86 from among the compounds in Compound Group 3 as described above was utilized as the second host, and AD-37 or AD-38 from among the compounds in Compound Group 4 as described above was utilized as the second dopant (sensitizer).
Compounds utilized for manufacturing the light emitting elements of Examples and Comparative Examples are disclosed below. The materials below were utilized to manufacture the elements by subjecting commercial products to sublimation purification.
Device efficiencies and device service lives of the light emitting devices manufactured with Experimental Example Compounds 12, 43, 64, 78, and 118 and Comparative Example Compounds C1 to C5 as described above were evaluated. Evaluation results of the light emitting devices of Examples 1 to 5 and Comparative Examples 1 to 5 are listed in Tables 1 and 2. Evaluation results of device efficiencies of the light emitting devices not including the fourth compound in the emission layer are listed in Table 2 in comparison with Table 1. In order to evaluate the characteristics of the light emitting devices according to each of Tables 1 and 2, each of driving voltages (V), luminous efficiencies (cd/A), and luminous colors was measured at a brightness of 1,000 cd/m2 by utilizing Keithley MU 236 and a luminance meter PR650, and the relative device service life was set as a numerical value in which the time it took for the brightness to deteriorate from an initial value to 95% brightness when the device was continuously operated at a brightness of 1,000 cd/m2 was compared to that of Comparative Example 1, and then the evaluation was carried out using the value for Comparative Example 1 as 100%.
Referring to the results of Tables 1 and 2, it may be confirmed that Examples of the light emitting devices in which the fused polycyclic compounds according to examples of the present disclosure are utilized as a luminescent material exhibit lower driving voltage, high luminous efficiency, and service life characteristics as compared with Comparative Examples. Example Compounds include at least two substituents, in which a phenyl group is bonded at the meta-position, in triphenyl silane, thereby may effectively maintain a trigonal planar structure of the boron atom through a steric hindrance effect by the substituents, and thus high efficiencies and long service lives of the light emitting devices including Example Compounds may be achieved. Example Compounds may have an increase in the luminous efficiency and may suppress or reduce the red shift of luminescence wavelength because the intermolecular interaction may be suppressed or reduced by the introduction of the substituents, thereby controlling the formation of excimer or exciplex. In addition, Example Compounds has an increase in the distance between adjacent molecules due to the large steric hindrance structure to thereby suppress or reduce the Dexter energy transfer, and thus may suppress or reduce the deterioration of service life due to the increase of triplet density.
The light emitting device of an embodiment may exhibit improved device characteristics with high efficiency and a long service life.
The fused polycyclic compound of an embodiment may be included in the emission layer of the light emitting device to contribute to high efficiency and a long service life of the light emitting device.
The use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression, such as “at least one of a, b or c”, “at least one selected from a, b, and c”, “at least one selected from the group consisting of a, b, and c”, “at least one from among a, b, and c”, etc., indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variation(s) thereof.
As used herein, the terms “substantially”, “about”, and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” or “approximately,” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value. Any numerical range recited herein is intended to include all sub-ranges of
the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The electronic apparatus, the display device, and/or any other relevant devices or components according to embodiments of the present invention described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
Although the present disclosure has been described with reference to a preferred embodiment of the present disclosure, it will be understood that the present disclosure should not be limited to these preferred embodiments but one or more suitable changes and modifications can be made by those skilled in the art without departing from the spirit and scope of the present disclosure.
Accordingly, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended claims, and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0067161 | May 2022 | KR | national |
