Patent Application
20240334829
The present application claims priority to and the benefit of Korean Patent Application No. 10-2023-0029486, filed on Mar. 6, 2023, in the Korean Intellectual Property Office, the content of which in its entirety is herein incorporated by reference.
One or more embodiments of the present disclosure relate to a light emitting element and a fused polycyclic compound utilized in the light emitting element.
Recently, the development of an organic electroluminescence display device as an image display device is being actively conducted. Unlike liquid crystal display devices and/or the like, the organic electroluminescence display device is a self-luminescent display device in which holes and electrons respectively injected from a first electrode and a second electrode recombine in an emission layer of the organic electroluminescence display device, and thus a luminescent material including an organic compound in the emission layer emits light to implement display (e.g., of an image).
In the application of an organic electroluminescence device to a display, reducing the driving voltage and increasing the emission efficiency and the life (e.g., lifespan) of the organic electroluminescence device are desired and/or required; thus, development on materials for an organic electroluminescence device stably attaining the desires and/or requirements is being continuously conducted and/or pursued.
In recent years, in order to implement a highly efficient organic electroluminescence device, technologies pertaining to phosphorescence emission utilizing triplet state energy or fluorescence utilizing triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons are being particularly developed, and thus thermally activated delayed fluorescence (TADF) materials utilizing delayed fluorescence phenomenon are being developed.
One or more aspects of embodiments of the present disclosure are directed toward a light emitting element in which an element service life (e.g., lifespan) is improved.
One or more aspects of embodiments of the present disclosure are directed toward a fused polycyclic compound capable of improving an element service life of a light emitting element.
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.
According to one or more embodiments of the present disclosure, a light emitting element includes a first electrode, a second electrode on the first electrode, and at least one functional layer which is between the first electrode and the second electrode and includes a fused polycyclic compound represented by Formula 1:
In Formula 1, X may be O, S, or NRX2, Y is a direct linkage, when X is O or S, m may be 0 or 1 and when X is NRX2, m is 1, RX1 may be a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or represented by Formula 1-1, RX2 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, R1 to R5 may each independently be hydrogen, deuterium, a halogen, 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, Ry may be hydrogen, deuterium, 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, n1 may be an integer of 0 to 3, n2, n4, and n5 may each independently be an integer of 0 to 4, and n3 may be an integer of 0 to 2.
In Formula 1-1, RZ1 and RZ2 may each independently be hydrogen, deuterium, a halogen, 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, a may be an integer of 0 to 5, b may be an integer of 0 to 3, ring A to ring F may each independently be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring, at least one selected from among ring A to ring F is present and the rest are absent, and is a position linked to Formula 1.
In one or more embodiments, the at least one functional layer may include an emission layer, a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode, and the emission layer may include the fused polycyclic compound.
In one or more embodiments, the emission layer may be to emit delayed fluorescence.
In one or more embodiments, the emission layer may be to emit light having a luminescence center wavelength of about 430 nm to about 490 nm.
In one or more embodiments, ring A to ring F may each independently be a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted benzene ring.
In one or more embodiments, the substituent represented by RX1 may be represented by any one selected from among Formula 1-1a to Formula 1-1m:
In Formula 1-1a to Formula 1-1m, R11 to R33 may each independently be hydrogen, deuterium, a halogen, 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, m1 may be an integer of 0 to 15, m2 and m3 may each independently be an integer of 0 to 7, m4, m6, m8, m10, m13, m15, and m17 may each independently be an integer of 0 to 6, m5, m7, m9, m11, m14, m16, m18, m20, m22, and m23 may each independently be an integer of 0 to 5, m12 may be an integer of 0 to 9, m19 may be an integer of 0 to 8, m21 may be an integer of 0 to 3, and is a position linked to Formula 1.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 2-1 to Formula 2-3:
In Formula 2-1 to Formula 2-3, Xa may be O or S.
In Formula 2-1 to Formula 2-3, the same as defined in Formula 1 may be applied to RX1, RX2, R1 to R5, Ry, and n1 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 3-1 to Formula 3-3:
In Formula 3-1 to Formula 3-3, Xa may be O or S, A1 may be hydrogen or deuterium, R41 to R43 may each independently be hydrogen, deuterium, a halogen, 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, n41 may be an integer of 0 to 5, and n42 and n43 may each independently be an integer of 0 to 4.
In Formula 3-1 to Formula 3-3, the same as defined in Formula 1 may be applied to X, Y, RX1, R1 to R5, m, and n1 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 4:
In Formula 4, RX2′ may be represented by Formula 1-2:
In Formula 1-2, RZ3 and RZ4 may each independently be hydrogen, deuterium, a halogen, 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, c may be an integer of 0 to 5, d may be an integer of 0 to 3, ring G to ring L may each independently be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring, at least one selected from among ring G to ring L is present and the rest are absent, and is a position linked to Formula 4.
In Formula 4, the same as defined in Formula 1 may be applied to RX1, R1 to R5, Ry, and n1 to n5.
In one or more embodiments, the substituent represented by Ry may be hydrogen or represented by Formula A-1 or Formula A-2:
In Formula A-1 and Formula A-2, Ra1 to Ra3 may each independently be hydrogen, deuterium, a halogen, 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, b1 may be an integer of 0 to 5, b2 and b3 may each independently be an integer of 0 to 4, and is a position linked to Formula 1.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 5-1 to Formula 5-3:
In Formula 5-1 to Formula 5-3, R2′ and R2″ may each independently be hydrogen, deuterium, a halogen, 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, n2′ may be an integer of 0 to 3, n2″ may be an integer of 0 to 2, and R2a and R2b may each independently be represented by Formula B-1 or Formula B-2:
In Formula B-1 and Formula B-2, Rb1 to Rb3 may each independently be hydrogen, deuterium, a halogen, 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, c1 may be an integer of 0 to 5, and c2 and c3 may each independently be an integer of 0 to 4.
In Formula 5-1 to Formula 5-3, the same as defined in Formula 1 above may be applied to X, Y, RX1, R1, R3 to R5, Ry, m, n1, and n3 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 6-1 to Formula 6-3:
In Formula 6-1 to Formula 6-3, Ry′ may be represented by Formula A-1 or Formula A-2, RX2″ may be represented by any one selected from among Formula 1-2a to Formula 1-2m:
In Formula A-1 and Formula A-2, Ra1 to Ra3 may each independently be hydrogen, deuterium, a halogen, 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, b1 may be an integer of 0 to 5, b2 and b3 may each independently be an integer of 0 to 4, and is a position linked to Formula 6-1, Formula 6-2, or Formula 6-3.
In Formula 1-2a to Formula 1-2m, R51 to R73 may each independently be hydrogen, deuterium, a halogen, 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, d1 may be an integer of 0 to 15, d2 and d3 may each independently be an integer of 0 to 7, d4, d6, d8, d10, d13, d15, and d17 may each independently be an integer of 0 to 6, d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 may each independently be an integer of 0 to 5, d12 may be an integer of 0 to 9, d19 may be an integer of 0 to 8, d21 may be an integer of 0 to 3, and is a position linked to Formula 6-3.
In Formula 6-1 to Formula 6-3, the same as defined in Formula 1 above may be applied to Y, RX1, R1 to R5, Ry, m, and n1 to n5.
In one or more embodiments of the present disclosure, a fused polycyclic compound is 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. Above and/or other aspects of the present disclosure should become apparent and appreciated from the following description of embodiments taken in conjunction with the accompanying drawings. In the drawings:
The present disclosure may be modified in one or more suitable manners and have many forms, and thus specific embodiments will be exemplified in the drawings and described in more detail in the detailed description of the present disclosure. 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 utilized 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 utilized herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only utilized to distinguish one component from another. 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 example embodiments of the present disclosure. As utilized herein, the singular forms, “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the utilization of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
In the present disclosure, it will be understood that the terms “comprise(s),” “include(s),” “have/has” and/or the like specify the presence of features, numbers, steps, operations, component, 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, component, parts, or combinations thereof. As utilized herein, the terms “and,” “or,” and “and/or” may include any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, “at least one of a, b, or c”, “at least one selected from a, b, and c”, “at least one selected from among a to c”, etc., may indicate only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof. The “/” utilized herein may be interpreted as “and” or as “or” depending on the situation.
In the present disclosure, when a layer, a film, a region, or a plate is referred to as being “on” or “in an upper portion of” another layer, film, region, or plate, it may be not only “directly on” the layer, film, region, or plate, but intervening layers, films, regions, or plates may also be present. Opposite this, when a layer, a film, a region, or a plate is referred to as being “below”, “in a lower portion of” another layer, film, region, or plate, it can be not only directly under the 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 some embodiments, “directly on” may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, “directly on” may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.
In the present disclosure, the term “substituted or unsubstituted” may refer to substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, a halogen, 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, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In some embodiments, each of the substituents exemplified above 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 present disclosure, the phrase “bonded to an adjacent group to form a ring” may refer to that a group is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. The hydrocarbon ring may include an aliphatic hydrocarbon ring and/or an aromatic hydrocarbon ring. The heterocycle may include an aliphatic heterocycle and/or an aromatic heterocycle. The hydrocarbon ring and the heterocycle may each be monocyclic or polycyclic. In some embodiments, the rings formed by two adjacent groups being bonded to each other may be connected to another ring to form a spiro structure.
In the present disclosure, 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 some embodiments, two methyl groups in 4,5-dimethylphenanthrene may be interpreted as “adjacent groups” to each other.
In the present disclosure, examples of the halogen may include fluorine, chlorine, bromine, or iodine.
In the present disclosure, an alkyl group may be linear or branched. The number of carbons in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 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 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, 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, 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, a cycloalkyl group may refer to a cyclic alkyl group. The number of carbons in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, an alkenyl group may refer to a hydrocarbon group including at least one carbon-carbon double bond in the middle or terminal of an alkyl group having 2 or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not specifically limited, for example, may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group may 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, an alkynyl group may refer to a hydrocarbon group including at least one carbon-carbon triple bond in the middle or terminal of an alkyl group having 2 or more carbon atoms. The alkynyl group may be linear or branched. Although the number of carbon atoms is not specifically limited, it may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include an ethynyl group, a propynyl group, etc., but embodiments of the present disclosure are not limited thereto.
In the present disclosure, a hydrocarbon ring group may refer to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.
In the present disclosure, an aryl group may refer 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 fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quinquephenyl group, a sexiphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group, a chrysenyl group, etc., but embodiments of the present disclosure are not limited thereto.
In the present disclosure, a 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, embodiments of the present disclosure are not limited thereto.
A heterocyclic group herein may refer 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 may include an aliphatic heterocyclic group and/or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may each be monocyclic or polycyclic.
In the present disclosure, the heterocyclic group may contain at least one of B, O, N, P, Si or S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.
In the present disclosure, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, or S as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiane group, a tetrahydropyran group, a 1,4-dioxane group, etc., but embodiments of the present disclosure are not limited thereto.
In the present disclosure, the heteroaryl group may contain 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, 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 present disclosure, a silyl group may include an alkylsilyl group and/or 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, the number of ring-forming carbon atoms in a carbonyl group is not specifically limited, for example, may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structures, but embodiments of the present disclosure are not limited thereto.
In the present disclosure, the number of carbon atoms in a sulfinyl group or a sulfonyl group is not particularly limited, for example, may be 1 to 30. The sulfinyl group may include an alkyl sulfinyl group and/or an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and/or an aryl sulfonyl group.
In the present disclosure, a thio group may include an alkylthio group and/or 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, 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/or an aryl oxy group. The alkoxy group may be a linear chain, a branched chain, or a ring. 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 methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but embodiments of the present disclosure are not limited thereto.
A boron group 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/or 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 embodiments of the present disclosure are not limited thereto.
In the present disclosure, the number of carbon atoms in an amine group is not specifically limited, for example, may be 1 to 30. The amine group may include an alkyl amine group and/or 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, etc., but embodiments of the present disclosure are not limited thereto.
In the present disclosure, the alkyl group among an alkoxy group, an alkylthio group, an alkylsulfoxy group, an alkylaryl group, an alkylamino group, an alkyl boron group, an alkyl silyl group, and an alkyl amine group may be the same as the examples of the alkyl group described above.
In the present disclosure, the aryl group among an aryloxy group, an arylthio group, an arylsulfoxy group, an arylamino group, an arylboron group, an arylsilyl group, and an arylamine group may be the same as the examples of the aryl group described above.
In the present disclosure, a direct linkage may refer to a single bond.
In the present disclosure,
and “” may refer to a position to be connected.
Hereinafter, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. In the present disclosure, term “light emitting device” may be utilized interchangeably with the term “light emitting element.”
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 may include 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 reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarization layer and/or a color filter layer. In some embodiments, the optical layer PP may not be provided in the display apparatus DD.
A base substrate BL may be provided and 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 disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, the base substrate BL may not be provided.
The display apparatus DD according to one or more embodiments 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 a 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 respective 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, embodiments of the present disclosure are not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
In one or more embodiments, the circuit layer DP-CL may be 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, in some embodiments, the circuit layer DP-CL may include switching transistor(s) and driving transistor(s) 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 independently have a structure of one of light emitting devices 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 may include at least one insulation layer. In some embodiments, the encapsulation layer TFE may include at least one inorganic film (hereinafter, an encapsulation-inorganic film). In some embodiments, the encapsulation layer TFE may 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 embodiments of the present disclosure are not particularly limited thereto. The encapsulation-organic film may include an acrylic-based compound, an epoxy-based compound, and/or the like. In some embodiments, the encapsulation-organic film may include a photopolymerizable organic material, but embodiments of the present disclosure are not particularly limited thereto.
The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed filling 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 adjacent light emitting areas PXA-R, PXA-G, and PXA-B, which correspond to the pixel defining film PDL. In some embodiments, the light emitting regions PXA-R, PXA-G, and PXA-B may respectively correspond to pixels. The pixel defining film PDL may divide the light emitting devices ED-1, ED-2, and ED-3. The respective 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 one or more embodiments illustrated in
In the display apparatus DD according to one or more embodiments, the plurality of light emitting devices ED-1, ED-2, and ED-3 may be to emit light beams having wavelengths different from each other. For example, in one or more embodiments, 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, in some embodiments, 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, embodiments of the present disclosure are not limited thereto, and the first to third light emitting devices ED-1, ED-2, and ED-3 may be to emit light beams in substantially the same wavelength range, or at least one light emitting device may be to emit a light beam in a wavelength range different from the others. For example, in some embodiments, 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 one or more embodiments 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 some embodiments, the area of the green light emitting region PXA-G may be smaller than that of the blue light emitting region PXA-B, but embodiments of the present disclosure are not limited thereto.
Hereinafter,
The light emitting element ED may include a hole transport region HTR, an emission layer EML, an electron transport region ETR, and/or the like, stacked in order (e.g., in the stated order), as the at least one functional layer. Referring to
Compared with
The first electrode EL1 has conductivity (e.g., is a conductor). The first electrode EL1 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, embodiments of the present disclosure are 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 EL1 may include at least one selected from among silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), and zinc (Zn), one or more compounds each being of two or more selected therefrom, one or more mixtures each being of two or more selected therefrom, and/or one or more oxides 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 EL1 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 thereof, or a 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, in some embodiments, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but embodiments of the present disclosure are not limited thereto. The first electrode EL1 may include one 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. A thickness of the first electrode EL1 may be from about 700 Å to about 10,000 Å. For example, in one or more embodiments, the thickness of the first electrode EL1 may be from about 1,000 Å to about 3,000 Å.
The hole transport region HTR may be 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. A 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, in one or more embodiments, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a 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 order (e.g., in the stated order) from the first electrode EL1, but embodiments of the present disclosure are 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 casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
In one or more embodiments, the hole transport region HTR may include a compound represented by Formula H-1:
In Formula H-1, 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-1, 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-1, 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-1 may be a monoamine compound. In some embodiments, the compound represented by Formula H-1 may be a diamine compound in which at least one selected from among Ar1 to Ar3 may include an amine group as a substituent. In some embodiments, the compound represented by Formula H-1 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-1 may be represented by any one selected from among compounds in Compound Group H. However, the compounds listed in Compound Group H are mere examples, and the compounds represented by Formula H-1 are not limited to those represented in Compound Group H:
In one or more embodiments, the hole transport region HTR may include at least one selected from a phthalocyanine compound such as copper phthalocyanine, N1,N1′-([1,1′-biphenyl]-4,4′-diyl)bis(N1-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(naphthalen-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.
In one or more embodiments, the hole transport region HTR may include at least one selected from a carbazole-based derivative such as N-phenyl carbazole 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) or 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), N,N′-di(naphthalen-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 at least one selected from 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-yl)benzene (mDCP), etc.
The hole transport region HTR may include at least one of 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.
A 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 a 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 a 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 an 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.
In one or more embodiments, 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 substantially 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 embodiments of the present disclosure are not limited thereto. For example, in some embodiments, 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]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but embodiments of the present disclosure are 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 may be 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 multiple different materials, or a multi-layered structure having a plurality of layers formed of multiple different materials.
The light emitting element ED of one or more embodiments may include a fused polycyclic compound represented by Formula 1 in the at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The emission layer EML in the light emitting element ED according to one or more embodiments may include a fused polycyclic compound of one or more embodiments. In one or more embodiments, the emission layer EML may include the fused polycyclic compound of one or more embodiments as a dopant. The fused polycyclic compound of one or more embodiments may be a dopant material of the emission layer EML. In the present disclosure, the fused polycyclic compound of one or more embodiments, which will be described later, may be referred to as a first compound.
The fused polycyclic compound of one or more embodiments may include a structure in which a plurality of aromatic rings are fused via a boron atom, a first nitrogen atom, and a first heteroatom. For example, the fused polycyclic compound of one or more embodiments may include a structure in which first to third aromatic rings are fused via one boron atom, the first nitrogen atom, and the first heteroatom. The first to third aromatic rings each may be linked to the boron atom, the first aromatic ring and the second aromatic ring may be linked to each other via the first nitrogen atom, and the first aromatic ring and the third aromatic ring may be linked to each other via the first heteroatom. In one or more embodiments, the first to third aromatic rings may be 6-membered aromatic hydrocarbon rings. For example, in one or more embodiments, the first to third aromatic rings may be benzene rings. In one or more embodiments, the first heteroatom may be an oxygen atom (O), a sulfur atom (S), or a nitrogen atom (N). In the present disclosure, the boron atom, the first nitrogen atom, and the first heteroatom, and the first to third aromatic rings which are fused via the boron atom, the first nitrogen atom, and the first heteroatom may be referred to as “fused ring core.”
The fused polycyclic compound of one or more embodiments may include a first substituent linked to the fused ring core. The first substituent may be linked to the first nitrogen atom. The first substituent may include a first benzene ring, and include a structure in which a second benzene ring is linked to carbon at a specific position of the first benzene ring. For example, in some embodiments, the first substituent may include a structure in which the first benzene ring linked to the first nitrogen atom is linked to the second benzene ring which is linked to the ortho-position carbon with respect to the carbon atom linked to the first nitrogen atom among carbon atoms constituting the first benzene ring. In the present disclosure, the first benzene ring and second benzene ring linked to each other may be referred to as a “first biphenyl ring.” The first biphenyl ring may be represented by Formula R1. In one or more embodiments, the first substituent may include a first ring which is fused with or linked to the first biphenyl ring. The first ring may be fused so as to share at least two carbon atoms among the carbon atoms constituting the first biphenyl ring or covalently linked to one carbon atom constituting the first biphenyl ring. For example, referring to Formula R1, the first ring may be fused so as to share at least two carbons selected from among a1 carbon, a2 carbon, and b1 carbon to b5 carbon, or may be covalently linked to any one selected from among a2 carbon, and b2 carbon to b5 carbon. In one or more embodiments, the first ring may be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring. For example, in one or more embodiments, the first ring may be a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted benzene ring. In one or more embodiments, the first substituent may include at least one first ring. For example, in one or more embodiments, the first ring may be provided alone or in plurality. When the first rings are provided in plurality, the plurality of first rings may be provided so as to share at least two carbon atoms while being fused to each other, but embodiments of the present disclosure are not limited thereto. In the present disclosure, the first substituent may refer to a substituent represented by Formula 1-1 which will be described later.
In Formula R1, is a position linked to the first nitrogen atom of the fused ring core.
The fused polycyclic compound of one or more embodiments may include a second substituent linked to the fused ring core. The second substituent may be linked to the third aromatic ring. The second substituent may contain a second nitrogen atom, and a fourth aromatic ring and a fifth aromatic ring linked to the second nitrogen atom. The fourth aromatic ring and the fifth aromatic ring may be linked to each other to form a fused ring, or the fourth aromatic ring and the fifth aromatic ring may not be linked to each other but may be present to be separated. The fourth aromatic ring and the fifth aromatic ring may each independently be a six-membered aromatic hydrocarbon ring. For example, the fourth aromatic ring and the fifth aromatic ring may each independently be benzene rings. In one or more embodiments, the second substituent may contain a carbazole moiety or a diphenylamine moiety. The second substituent may be linked at the para-position with respect to the first heteroatom of the fused ring core. The second nitrogen atom of the second substituent may be linked to the third aromatic ring at the para-position with respect to the first heteroatom. For example, the second substituent may be linked to the third aromatic ring at the para-position carbon with respect to the carbon atom, linked to the first heteroatom, among carbon atoms constituting the third aromatic ring. The second substituent may be directly bonded to the third aromatic ring.
The fused polycyclic compound of one or more embodiments may be represented by Formula 1:
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may include a structure in which three aromatic rings are fused via one boron atom, a first nitrogen atom, and a first heteroatom. In the present disclosure, the benzene ring, which is substituted with the substituent represented by R1 in Formula 1, may correspond to the aforementioned first aromatic ring, the benzene ring, which is substituted with the substituent represented by R2, may correspond to the aforementioned second aromatic ring, and the benzene ring, which is substituted with the substituent represented by R3, may correspond to the aforementioned third aromatic ring. In addition, the benzene ring, which is substituted with the substituent represented by R4 in Formula 1, may correspond to the aforementioned fourth aromatic ring, and the benzene ring, which is substituted with the substituent represented by R5, may correspond to the aforementioned fifth aromatic ring. The substituent represented by RX1 in Formula 1 may correspond to the aforementioned first substituent. The substituent moiety including the benzene ring substituted with the substituent represented by R4 and the benzene ring substituted with the substituent represented by R5 may correspond to the aforementioned second substituent.
In Formula 1, X may be O, S, or NRX2.
In Formula 1, Y may be a direct linkage.
In Formula 1, m may be 0 or 1.
In Formula 1, when m is 0, the second substituent may have structure S1. For example, in Formula 1, when m is 0, the second substituent may include a diphenylamine moiety. In structure S1, is a position linked to the fused ring core in Formula 1:
In Formula 1, when m is 1, the second substituent may have structure S2. For example, in Formula 1, when m is 1, the second substituent may include a carbazole moiety. In structure S2, is a position linked to the fused ring core in Formula 1 above:
In Formula 1, when X is O or S, m may be 0 or 1. In one or more embodiments, in Formula 1, when X is NRX2, m is 1. For example, in one or more embodiments, in Formula 1, when x is O or S, the second substituent may include a carbazole moiety or a diphenylamine moiety. In one or more embodiments, in Formula 1, when X is NRX2, the second substituent may include a carbazole moiety.
In Formula 1, RX1 is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or represented by Formula 1-1. For example, in some embodiments, RX1 may be a substituted or unsubstituted adamantyl group or represented by Formula 1-1.
In Formula 1, RX2 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, in some embodiments, RX2 may be a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted a naphthyl group, or a substituted or unsubstituted phenanthrene group.
In Formula 1, R1 to R5 may each independently be hydrogen, deuterium, a halogen, 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. For example, in some embodiments, R1 to R5 may each independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.
In Formula 1, Ry may be hydrogen, deuterium, 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. For example, in one or more embodiments, Ry may be hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.
In Formula 1, n1 may be an integer of 0 to 3. In Formula 1, when n1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R1. In Formula 1, the case (e.g., embodiments) where n1 is 3 and R1's are all hydrogens may be the same as the case (e.g., embodiments) where n1 is 0 in Formula 1. When n1 is an integer of 2 or greater, a plurality of R1's may all be the same, or at least one among (e.g., selected from among) the plurality of R1's may be different from the others.
In Formula 1, n2, n4, and n5 may each independently be an integer of 0 to 4. In Formula 1, when each of n2, n4, and n5 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R2, R4, and R5. In Formula 1, the case (e.g., embodiments) where each of n2, n4, and n5 is 4 and R2's, R4's, and R5's are each hydrogen may be the same as the case (e.g., embodiments) where each of n2, n4, and n5 is 0 in Formula 1. When each of n2, n4, and n5 is an integer of 2 or greater, a plurality of R2's, a plurality of R4's, and a plurality of R5's each may be the same, or at least one selected from among the plurality of R2's, the plurality of R4's, and the plurality of R5's may be different from the others.
In Formula 1, n3 is an integer of 0 to 2. In Formula 1, when n3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R3. In Formula 1, the case (e.g., embodiments) where n3 is 2 and R3's are all hydrogens may be the same as the case (e.g., embodiments) where n3 is 0 in Formula 1. When n3 is 2, a plurality of R3's are all the same, or at least one among the plurality of R3's may be different from the others.
In Formula 1-1, ring A to ring F may each independently be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring. In one or more embodiments, ring A to ring F may each independently be a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted benzene ring.
In Formula 1-1, at least one selected from among ring A to ring F is present, and the rest are absent. For example, in one or more embodiments, the first substituent represented by Formula 1-1 may include at least one selected from among ring A to ring F. For example, in some embodiments, in Formula 1-1, ring A may be present, and the remaining ring B to ring F may be absent. In some embodiments, in Formula 1-1, ring B may be present, and the remaining ring A and ring C to ring F may be absent. In some embodiments, in Formula 1-1, ring C may be present, and the remaining ring A, ring B, and ring D to ring F may be absent. In some embodiments, in Formula 1-1, ring D may be present, and the remaining ring A to ring C, ring E, and ring F may be absent. In some embodiments, in Formula 1-1, ring E may be present, and the remaining ring A to ring D and ring F may be absent. In some embodiments, in Formula 1-1, ring D and ring F may be present, and the remaining ring A to ring C and ring E may be absent.
In Formula 1-1, RZ1 and RZ2 may each independently be hydrogen, deuterium, a halogen, 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. For example, in some embodiments, RZ1 and RZ2 may each independently be hydrogen, deuterium, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In Formula 1-1, a may be an integer of 0 to 5. In Formula 1-1, when a is 0, the fused polycyclic compound of one or more embodiments may not be substituted with RZ1. In Formula 1-1, the case (e.g., embodiments) where a is 5 and RZ1's are all hydrogens may be the same as the case (e.g., embodiments) where a is 0 in Formula 1-1. When a is an integer of 2 or greater, a plurality of RZ1's may be all the same, or at least one among the plurality of RZ1's may be different from the others.
In Formula 1-1, b may be an integer of 0 to 3. In Formula 1-1, when b is 0, the fused polycyclic compound of one or more embodiments may not be substituted with RZ2. In Formula 1-1, the case (e.g., embodiments) where b is 3 and RZ2's are all hydrogens may be the same as the case (e.g., embodiments) where b is 0 in Formula 1-1. When b is an integer of 2 or greater, a plurality of RZ2's may be all the same, or at least one among the plurality of RZ2's may be different from the others.
In Formula 1-1, is a position linked to Formula 1.
In one or more embodiments, the substituent represented by Formula 1-1 may be represented by any one selected from among Formula 1-1-1 to Formula 1-1-7:
Formula 1-1-1 to Formula 1-1-7 represent the cases (e.g., embodiments) where it is specified whether each of ring A to ring F is included in Formula 1-1. Formula 1-1-1 represents the case (e.g., embodiments) where in Formula 1-1, ring A is present, and the remaining ring B to ring F are absent. Formula 1-1-2 represents the case (e.g., embodiments) where in Formula 1-1, ring B is present, and the remaining ring A and ring C to ring F are absent. Formula 1-1-3 represents the case (e.g., embodiments) where in Formula 1-1, ring C is present, and the remaining ring A, ring B, and ring D to ring F are absent. Formula 1-1-4 represents the case (e.g., embodiments) where in Formula 1-1, ring D is present, and the remaining ring A to ring C, ring E, and ring F are absent. Formula 1-1-5 represents the case (e.g., embodiments) where in Formula 1-1, ring D and ring F are present, and the remaining ring A to ring C and ring E are absent. Formula 1-1-6 represents the case (e.g., embodiments) where in Formula 1-1, ring B and ring D are present, and the remaining ring A, ring C, ring E, and ring F are absent. Formula 1-1-7 represents the case (e.g., embodiments) where in Formula 1-1, ring E is present, and the remaining ring A to ring D, and ring F are absent.
In one or more embodiments, Formula 1-1 may be any one selected from Substituent Group S: In the Substituent Group, the same as described in Formula 1-1 above may be applied to ring A to ring F.
In one or more embodiments, the substituent represented by RX1 may be represented by any one selected from among Formula 1-1a to Formula 1-1m:
In Formula 1-1a to Formula 1-1m, R11 to R33 may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, R11 to R33 may each independently be hydrogen, deuterium, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In Formula 1-1a, m1 may be an integer of 0 to 15. In Formula 1-1a, when m1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R11. In Formula 1-1a, the case (e.g., embodiments) where m1 is 15 and R11's are all hydrogens may be the same as the case (e.g., embodiments) where m1 is 0 in Formula 1-1a. When m1 is an integer of 2 or greater, a plurality of R11's may all be the same, or at least one among the plurality of R11's may be different from the others.
In Formula 1-1b and Formula 1-1c, m2 and m3 may each independently be an integer of 0 to 7. In Formula 1-1b and Formula 1-1c, when each of m2 and m3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R12 and R13. In Formula 1-1b and Formula 1-1c, the case (e.g., embodiments) where each of m2 and m3 is 7 and R12's and R13's are each hydrogen may be the same as the case (embodiments) where each of m2 and m3 is 0 in Formula 1-1b and Formula 1-1c. When each of m2 and m3 is an integer of 2 or greater, a plurality of R12's and R13's may each be the same, or at least one among the plurality of R12's and R13's may be different from the others.
In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1k, m4, m6, m8, m10, m13, m15, and m17 may each independently be an integer of 0 to 6. In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1k, when each of m4, m6, m8, m10, m13, m15, and m17 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R14, R16, R18, R20, R23, R25, and R27. In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1k, the case (e.g., embodiments) where each of m4, m6, m8, m10, m13, m15, and m17 is 6, and R14's, R16's, R18's, R20's, R23's, R25's, and R27's are each hydrogen may be the same as the case (e.g., embodiments) where each of m4, m6, m8, m10, m13, m15, and m17 is 0 in Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1k. When each of m4, m6, m8, m10, m13, m15, and m17 is an integer of 2 or greater, a plurality of R14's, R16's, R18's, R20's, R23's, R25's, and R27's each may be the same, or at least one among the plurality of R14's, R16's, R18's, R20's, R23's, R25's, and R27's may be different from the others.
In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1m, m5, m7, m9, m11, m14, m16, m18, m20, m22, and m23 may each independently be an integer of 0 to 5. In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1m, when each of m5, m7, m9, m11, m14, m16, m18, m20, m22, and m23 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R15, R17, R19, R21, R24, R26, R28, R30, R32, and R33. In Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1m, the case (e.g., embodiments) where each of m5, m7, m9, m1, m14, m16, m18, m20, m22, and m23 is 5, and R15's, R17's, R19's, R21's, R24's, R26's, R28's, R30's, R32's, and R33's are each hydrogen may be the same as the case (e.g., embodiments) where each of m5, m7, m9, m11, m14, m16, m18, m20, m22, and m23 is 0 in Formula 1-1d to Formula 1-1g and Formula 1-1i to Formula 1-1m. When each of m5, m7, m9, m11, m14, m16, m18, m20, m22, and m23 is an integer of 2 or greater, a plurality of R15's, R17's, R19's, R21's, R24's, R26's, R28's, R30's, R32's, and R33's each may be the same, or at least one among the plurality of R15's, R17's, R19's, R21's, R24's, R26's, R28's, R30's, R32's, and R33's may be different from the others.
In Formula 1-1h, m12 may be an integer of 0 to 9. In Formula 1-1h, when m12 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R22. In Formula 1-1h, the case (e.g., embodiments) where m12 is 9 and R22's are all hydrogens may be the same as the case (embodiments) where m12 is 0 in Formula 1-1h. When m12 is an integer of 2 or greater, a plurality of R22's may all be the same, or at least one among the plurality of R22's may be different from the others.
In Formula 1-1i, m19 may be an integer of 0 to 8. In Formula 1-1i, when m19 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R29. In Formula 1-1i, the case (e.g., embodiments) where m19 is 8 and R29's are all hydrogens may be the same as the case (e.g., embodiments) where m19 is 0 in Formula 1-1i. When m19 is an integer of 2 or more, a plurality of R29's may all be the same, or at least one among the plurality of R29's may be different from the others.
In Formula 1-1m, m21 may be an integer of 0 to 3. In Formula 1-1m, when m21 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R31. In Formula 1-1m, the case (e.g., embodiments) where m21 is 3 and R31's are all hydrogens may be the same as the case (e.g., embodiments) where m21 is 0 in Formula 1-1m. When m21 is an integer of 2 or greater, a plurality of R31's may all be the same, or at least one among the plurality of R31's may be different from the others.
In Formula 1-1a to Formula 1-1m, is a position linked to Formula 1.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may further include a first sub-substituent linked to the fused ring core. The first sub-substituent may be linked to the third aromatic ring. The first sub-substituent may be linked to the third aromatic ring at the ortho-portion with respect to the first heteroatom of the fused ring core. For example, the first sub-substituent may be linked at the ortho-position with respect to the carbon atom, linked to the first heteroatom, among the carbon atoms constituting the third aromatic ring. In one or more embodiments, the first sub-substituent may be 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. For example, in some embodiments, the first sub-substituent may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group. In the fused polycyclic compound according to one or more embodiments, the first sub-substituent may be substituted at the ortho-position with respect to the first heteroatom, and thus may effectively protect the fused ring core due to the steric hindrance effect. Accordingly, the fused polycyclic compound of one or more embodiments may have improved structural stability, and thus service life characteristics of the light emitting element may be improved. In the present disclosure, the first sub-substituent may refer to that a hydrogen atom in Ry in Formula 1 as described above is excluded.
In one or more embodiments, Ry may be 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 one or more embodiments, the substituent represented by Ry may be hydrogen or represented by Formula A-1 or Formula A-2:
In Formula A-1 and Formula A-2, Ra1 to Ra3 may each independently be hydrogen, deuterium, a halogen, 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, in some embodiments, Ra1 to Ra3 may each independently be hydrogen, deuterium, or a substituted or unsubstituted t-butyl group.
In Formula A-1, b1 may be an integer of 0 to 5. In Formula A-1, when b1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with Ra1. In Formula A-1, the case (e.g., embodiments) where b1 is 5 and Ra1's are all hydrogens may be the same as the case (e.g., embodiments) where b1 is 0 in Formula A-1. When b1 is an integer of 2 or greater, a plurality of Ra1's may be all the same, or at least one among the plurality of Ra1's may be different from the others.
In Formula A-2, b2 and b3 may each independently be an integer of 0 to 4. In Formula A-2, when each of b2 and b3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of Ra2 and Ra3. In Formula A-2, the case (e.g., embodiments) where each of b2 and b3 is 4 and Ra2's and Ra3's are each hydrogen may be the same as the case (e.g., embodiments) where each of b2 and b3 is 0 in Formula A-2. When each of b2 and b3 is an integer of 2 or more, a plurality of Ra2's and Ra3's each may be the same, or at least one among the plurality of Ra2's and Ra3's may be different from the others.
In Formula A-1 and Formula A-2, is a position linked to Formula 1.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 2-1 to Formula 2-3:
Formula 2-1 to Formula 2-3 represent the cases (e.g., embodiments) where X and m are specified in Formula 1. Formula 2-1 represents the case (e.g., embodiments) where X is O or S, and m is 0 in Formula 1. Formula 2-2 represents the case (e.g., embodiments) where X is O or S, and m is 1 in Formula 1. Formula 2-3 represents the case (e.g., embodiments) where X is NRX2, and m is 1 in Formula 1.
In Formula 2-1 and Formula 2-2, Xa may be O or S.
In Formula 2-1 to Formula 2-3, the same as described in Formula 1 may be applied to RX1, RX2, R1 to R5, Ry, and n1 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 3-1 to Formula 3-3:
Formula 3-1 to Formula 3-3 represent the cases (e.g., embodiments) where the types (kinds) of X and/or Ry are specified in Formula 1. Formula 3-1 represents the case (e.g., embodiments) where Ry may be hydrogen or deuterium in Formula 1. Formula 3-2 represents the case (e.g., embodiments) where X may be O or S, and Ry may be a substituted or unsubstituted phenyl group in Formula 1. Formula 3-3 represents the case (e.g., embodiments) where X may be O or S, and Ry may be a substituted or unsubstituted carbazole group in Formula 1.
In Formula 3-2 and Formula 3-3, Xa may be O or S.
In Formula 3-1, A1 may be hydrogen or deuterium.
In Formula 3-2 and Formula 3-3, R41 to R43 may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, R41 to R43 may each independently be hydrogen, deuterium, or a substituted or unsubstituted t-butyl group.
In Formula 3-2, n41 may be an integer of 0 to 5. In Formula 3-2, when n41 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R41. In Formula 3-2, the case (e.g., embodiments) where n41 is 5 and R41's are all hydrogens may be the same as the case (e.g., embodiments) where n41 is 0 in Formula 3-2. When n41 is an integer of 2 or greater, a plurality of R41's may all be the same, or at least one among the plurality of R41's may be different from the others.
In Formula 3-3, n42 and n43 may each independently be an integer of 0 to 4. In Formula 3-3, when each of n42 and n43 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R42 and R43. In Formula 3-3, the case (e.g., embodiments) where each of n42 and n43 is 4 and R42's and R43's are each hydrogen may be the same as the case (e.g., embodiments) where each of n42 and n43 is 0 in Formula 3-3. When each of n42 and n43 is an integer of 2 or greater, a plurality of R42's and R43's may each be the same, or at least one among the plurality of R42's and R43's may be different from the others.
In Formula 3-1 to Formula 3-3, the same as described in Formula 1 may be applied to X, Y, RX1, R1 to R5, m, and n1 to n5.
In the fused polycyclic compound of one or more embodiments, the first heteroatom may be nitrogen. For example, the fused polycyclic compound of one or more embodiments may include a structure in which the first to third aromatic rings are fused via the boron atom, the first nitrogen atom, and a third nitrogen atom. When the fused polycyclic compound of one or more embodiments includes the third nitrogen atom, the fused polycyclic compound of one or more embodiments may further include a third substituent. The third substituent may be linked to the third nitrogen atom. The third substituent may include a third benzene ring, and include a structure in which a fourth benzene ring is linked to carbon at a specific position of the third benzene ring. For example, in some embodiments, the third substituent may include a structure in which the third benzene ring linked to the third nitrogen atom is linked to the fourth benzene ring which is linked to the ortho-position carbon with respect to the carbon atom linked to the third nitrogen atom among carbon atoms constituting the third benzene ring. In the present disclosure, the third benzene ring and fourth benzene ring linked to each other may be referred to as a “second biphenyl ring.” The second biphenyl ring may be represented by Formula R2. In one or more embodiments, the third substituent may include a second ring which is fused with or linked to the second biphenyl ring. The second ring may be fused so as to share at least two carbon atoms among the carbon atoms constituting the second biphenyl ring or covalently linked to one carbon atom constituting the second biphenyl ring. For example, referring to Formula R2, the second ring may be fused so as to share at least two carbons selected from among c1 carbon, c2 carbon, and d1 carbon to d5 carbon, or may be covalently linked to any one selected from among c2 carbon, and d2 carbon to d5 carbon. In one or more embodiments, the second ring may be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring. For example, in some embodiments, the second ring may be a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted benzene ring. In some embodiments, the third substituent may include at least one second ring. For example, the second ring may be provided alone or in plurality. In the present disclosure, the third substituent may refer to a substituent represented by Formula 1-2 which will be described later.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 4:
In Formula 4, RX2′ may be represented by Formula 1-2:
In Formula 1-2, ring G to ring L may each independently be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, or a substituted or unsubstituted six-membered aromatic hydrocarbon ring. In one or more embodiments, ring G to ring L may be a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted benzene ring.
In Formula 1-2, at least one selected from among ring G to ring L may be present, and the rest may be absent. For example, in one or more embodiments, the third substituent represented by Formula 1-2 may include at least one selected from among ring G to ring L. For example, in some embodiments, in Formula 1-2, ring G may be present, and the remaining ring H to ring L may be absent. In some embodiments, in Formula 1-2, ring H may be present, and the remaining ring G and ring I to ring L may be absent. In some embodiments, in Formula 1-2, ring I may be present, and the remaining ring G, ring H, and ring J to ring L may be absent. In some embodiments, in Formula 1-2, ring J may be present, and the remaining ring G to ring I, ring K, and ring L may be absent. In some embodiments, in Formula 1-2, ring K may be present, and the remaining ring G to ring J, and ring L may be absent. In some embodiments, in Formula 1-2, ring J and ring L may be present, and the remaining ring G to ring I, and ring K may be absent.
In Formula 1-2, RZ3 and RZ4 may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, RZ3 and RZ4 may each independently be hydrogen, deuterium, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In Formula 1-2, c is an integer of 0 to 5. In Formula 1-2, when c is 0, the fused polycyclic compound of one or more embodiments may not be substituted with RZ3. In Formula 1-2, the case (e.g., embodiments) where c is 5 and RZ3's are all hydrogens may be the same as the case (e.g., embodiments) where c is 0 in Formula 1-2. When c is an integer of 2 or greater, a plurality of RZ3's may be all the same, or at least one among the plurality of RZ3's may be different from the others.
In Formula 1-2, d is an integer of 0 to 3. In Formula 1-2, when d is 0, the fused polycyclic compound of one or more embodiments may not be substituted with RZ4. In Formula 1-2, the case (e.g., embodiments) where d is 3 and RZ4's are all hydrogens may be the same as the case (e.g., embodiments) where d is 0 in Formula 1-2. When d is an integer of 2 or greater, a plurality of RZ4's may be all the same or at least one among the plurality of RZ4's may be different from the others.
In Formula 1-2, is a position linked to Formula 4.
In Formula 4, the same as described in Formula 1 may be applied to RX1, R1 to R5, Ry, and n1 to n5.
In one or more embodiments, the substituent represented by Formula 1-2 may be represented by any one selected from among Formula 1-2-1 to Formula 1-2-7:
Formula 1-2-1 to Formula 1-2-7 represent the cases (e.g., embodiments) where it is specified whether each of ring G to ring L is included in Formula 1-2. Formula 1-2-1 represents the case (e.g., embodiments) where in Formula 1-2, ring G is present, and the remaining ring H to ring L are absent. Formula 1-2-2 represents the case (e.g., embodiments) where in Formula 1-2, ring H is present, and the remaining ring G and ring I to ring L are absent. Formula 1-2-3 represents the case (e.g., embodiments) where in Formula 1-2, ring I is present, and the remaining ring G, ring H, and ring J to ring L are absent. Formula 1-2-4 represents the case (e.g., embodiments) where in Formula 1-2, ring J is present, and the remaining ring G to ring I, ring K, and ring L are absent. Formula 1-2-5 represents the case (e.g., embodiments) where in Formula 1-2, ring J and ring L are present, and the remaining ring G to ring I and ring K are absent. Formula 1-2-6 represents the case (e.g., embodiments) where in Formula 1-2, ring H and ring J are present, and the remaining ring G, ring I, ring K, and ring L are absent. Formula 1-2-7 represents the case (e.g., embodiments) where in Formula 1-2, ring K is present, and the remaining ring G to ring J, and ring L are absent.
In one or more embodiments, RX2's may be represented by any one selected from among Formula 1-2a to Formula 1-2m:
In Formula 1-2a to Formula 1-2m, R51 to R73 may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, R51 to R73 may each independently be hydrogen, deuterium, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In Formula 1-2a, d1 may be an integer of 0 to 15. In Formula 1-2a, when d1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R51. In Formula 1-2a, the case (e.g., embodiments) where d1 is 15 and R51's are all hydrogens may be the same as the case (e.g., embodiments) where d1 is 0 in Formula 1-2a. When d1 is an integer of 2 or greater, a plurality of R51's may all be the same, or at least one among the plurality of R51's may be different from the others.
In Formula 1-2b and Formula 1-2c, d2 and d3 may each independently be an integer of 0 to 7. In Formula 1-2b and Formula 1-2c, when each of d2 and d3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R52 and R53. In Formula 1-2b and Formula 1-2c, the case (e.g., embodiments) where each of d2 and d3 is 7 and R52's and R53's are each hydrogen may be the same as the case (e.g., embodiments) where each of d2 and d3 is 0 in Formula 1-2b and Formula 1-2c. When each of d2 and d3 is an integer of 2 or greater, a plurality of R52's and R53's may each be the same, or at least one among the plurality of R52's and R53's may be different from the others.
In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2k, d4, d6, d8, d10, d13, d15, and d17 may each independently be an integer of 0 to 6. In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2k, when each of d4, d6, d8, d10, d13, d15, and d17 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R54, R56, R58, R60, R63, R65, and R67. In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2k, the case (e.g., embodiments) where each of d4, d6, d8, d10, d13, d15, and d17 is 6, and R54's, R56's, R58's, R60's, R63's, R65's, and R67's are each hydrogen may be the same as the case (e.g., embodiments) where each of d4, d6, d8, d10, d13, d15, and d17 is 0 in Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2k. When each of d4, d6, d8, d10, d13, d15, and d17 is an integer of 2 or greater, a plurality of R54's, R56's, R58's, R60's, R63's, R65's, and R67's each may be the same, or at least one among the plurality of R54's, R56's, R58's, R60's, R63's, R65's, and R67's may be different from the others.
In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2m, d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 may each independently be an integer of 0 to 5. In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2m, when each of d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of R55, R57, R59, R61, R64, R66, R68, R70, R72, and R73. In Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2m, the case (e.g., embodiments) where each of d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 is 5, and R55's, R57's, R59's, R61's, R64's, R66's, R68's, R70's, R72's, and R73's are each hydrogen may be the same as the case (e.g., embodiments) where each of d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 is 0 in Formula 1-2d to Formula 1-2g and Formula 1-2i to Formula 1-2m. When each of d5, d7, d9, d11, d14, d16, d18, d20, d22, and d23 is an integer of 2 or greater, a plurality of R55's, R57's, R55's, R61's, R64's, R66's, R68's, R70's, R72's, and R73's each may be the same, or at least one among the plurality of R55's, R57's, R59's, R61's, R64's, R66's, R68's, R70's, R72's, and R73's may be different from the others.
In Formula 1-2h, d12 may be an integer of 0 to 9. In Formula 1-2h, when d12 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R62. In Formula 1-2h, the case (e.g., embodiments) where d12 is 9 and R62's are all hydrogens may be the same as the case (e.g., embodiments) where d12 is 0 in Formula 1-2h. When d12 is an integer of 2 or greater, a plurality of R62's may all be the same, or at least one among the plurality of R62's may be different from the others.
In Formula 1-2l, d19 may be an integer of 0 to 8. In Formula 1-2l, when d19 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R69. In Formula 1-2l, the case (e.g., embodiments) where d19 is 8 and R69's are all hydrogens may be the same as the case where d19 is 0 in Formula 1-2l. When d19 is an integer of 2 or more, a plurality of R69's may all be the same, or at least one among the plurality of R69's may be different from the others.
In Formula 1-2m, d21 may be an integer of 0 to 3. In Formula 1-2m, when d21 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R71. In Formula 1-2m, the case (e.g., embodiments) where d21 is 3 and R71's are all hydrogens may be the same as the case (e.g., embodiments) where d21 is 0 in Formula 1-2m. When d21 is an integer of 2 or greater, a plurality of R71's may all be the same, or at least one among the plurality of R71's may be different from the others.
In Formula 1-2a to Formula 1-2m, is a position linked to Formula 4.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 5-1 to Formula 5-3:
In Formula 5-1 to Formula 5-3, R2′ and R2″ may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, R2′ and R2″ may each independently be hydrogen or deuterium.
In Formula 5-1 and Formula 5-2, n2′ is an integer of 0 to 3. In Formula 5-1 and Formula 5-2, when n2′ is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R2′. In Formula 5-1 and Formula 5-2, the case (e.g., embodiments) where n2′ is 3 and R2″s are all hydrogens may be the same as the case (e.g., embodiments) where n2′ is 0 in Formula 5-1 and Formula 5-2. When n2′ is an integer of 2 or greater, a plurality of R2″s may all be the same, or at least one among the plurality of R2″s may be different from the others.
In Formula 5-3, n2″ is an integer of 0 to 2. In Formula 5-3, when n2″ is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R2″. In Formula 5-3, the case (e.g., embodiments) where n2″ is 2 and R2″'s are all hydrogens may be the same as the case (e.g., embodiments) where n2″ is 0 in Formula 5-3. When n2″ is 2, a plurality of R2″'s may all be the same, or at least one among the plurality of R2″'s may be different from the others.
In Formula 5-1 to Formula 5-3, R2a and R2b may each independently be represented by Formula B-1 or Formula B-2:
In Formula B-1 and Formula B-2, Rb1 to Rb3 may each independently be hydrogen, deuterium, a halogen, 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 some embodiments, Rb1 to Rb3 may each independently be hydrogen or deuterium.
In Formula B-1, c1 may be an integer of 0 to 5. In Formula B-1, when c1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with Rb1. In Formula B-1, the case (e.g., embodiments) where c1 is 5 and Rb1's are all hydrogens atoms may be the same as the case (e.g., embodiments) where c1 is 0 in Formula B-1. When c1 is an integer of 2 or greater, a plurality of Rb1's may be all the same, or at least one among the plurality of Rb1's may be different from the others.
In Formula B-2, c2 and c3 may each independently be an integer of 0 to 4. In Formula B-2, when each of c2 and c3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of Rb2 and Rb3. In Formula B-2, the case (e.g., embodiments) where each of c2 and c3 is 4 and Rb2's and Rb3's are each hydrogen may be the same as the case (e.g., embodiments) where each of c2 and c3 is 0 in Formula B-2. When each of c2 and c3 is an integer of 2 or more, a plurality of Rb2's and Rb3's each may be the same, or at least one among the plurality of Rb2's and Rb3's may be different from the others.
In Formula 5-1 to Formula 5-3, the same as described in Formula 1 may be applied to X, Y, RX1, R1, R3 to R5, Ry, m, n1, and n3 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from among Formula 6-1 to Formula 6-3:
In Formula 6-1 and Formula 6-2, Ry′ may be represented by Formula A-1 or Formula A-2 as described above.
In Formula 6-3, RX2″ may be represented by any one selected from among Formula 1-2a to Formula 1-2m as described above.
In Formula 6-1 to Formula 6-3, the same as described in Formula 1 may be applied to Y, RX1, R1 to R5, Ry, m, and n1 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 7-1 or Formula 7-2:
In Formula 7-1 and Formula 7-2, Rc1 to Rc3 may each independently be hydrogen, deuterium, a halogen, 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. For example, in one or more embodiments, Rc1 to Rc3 may each independently be hydrogen or deuterium.
In Formula 7-1, e1 may be an integer of 0 to 5. In Formula 7-1, when e1 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with Rc1. In Formula 7-1, the case (e.g., embodiments) where e1 is 5 and Rc1's are all hydrogens may be the same as the case (e.g., embodiments) where e1 is 0 in Formula 7-1. When e1 is an integer of 2 or greater, a plurality of Rc1's may be all the same, or at least one among the plurality of Rc1's may be different from the others.
In Formula 7-2, e2 and e3 may each independently be an integer of 0 to 4. In Formula 7-2, when each of e2 and e3 is 0, the fused polycyclic compound of one or more embodiments may not be substituted with each of Rc2 and Rc3. In Formula 7-2, the case (e.g., embodiments) where each of e2 and e3 is 4 and Rc2's and Rc3's are each hydrogen may be the same as the case (e.g., embodiments) where each of e2 and e3 is 0 in Formula 7-2. When each of e2 and e3 is an integer of 2 or more, a plurality of Rc2's and Rc3's each may be the same, or at least one among the plurality of Rc2's and Rc3's may be different from the others.
In Formula 7-1 and Formula 7-2, the same as described in Formula 5-1 and Formula 5-2 may be applied to R2′ and n2′.
In Formula 7-1 and Formula 7-2, the same as described in Formula 1 may be applied to X, Y, RX1, R1, R3 to R5, Ry, m, n1, and n3 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 8:
In Formula 8, R1′ may be hydrogen, deuterium, a halogen, 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. For example, in some embodiments, R1′ may be hydrogen or deuterium. n1′ may be an integer of 0 to 2. When n1′ is 0, the fused polycyclic compound of one or more embodiments may not be substituted with R1′. In Formula 8, the case (e.g., embodiments) where n1′ is 2 and R1′(s) are all hydrogens may be the same as the case (e.g., embodiments) where n1′ is 0 in Formula 8. When n1′ is 2, two R1′(s) may be the same or different from each other.
In Formula 8, Ria may be 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, in some embodiments, Ria may be a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.
In Formula 8, the same as described in Formula 1 may be applied to Y, RX1, R2 to R5, Ry, m, and n2 to n5.
In one or more embodiments, the fused polycyclic compound represented by Formula 1 may include at least one deuterium atom as a substituent. In one or more embodiments, R1 to R5 in Formula 1 and at least one of RZ1 or RZ2 in RX1 represented by Formula 1-1 in Formula 1 may include deuterium or a substituent containing deuterium.
The fused polycyclic compound of one or more embodiments may be any one selected from among compounds represented in Compound Group 1. The light emitting element ED of one or more embodiments may include at least one fused polycyclic compound selected from among the compounds represented in Compound Group 1 in the emission layer EML.
In the example compounds presented in Compound Group 1, “D” refers to deuterium.
The fused polycyclic compound represented by Formula 1 according to one or more embodiments has a structure into which the first substituent and the second substituent are introduced, and thus may achieve high luminous efficiency and long service life (e.g., lifespan).
The fused polycyclic compound of one or more embodiments has a structure in which a plurality of aromatic rings are fused by the boron atom, the first nitrogen atom, and the first heteroatom, and desirably includes, as a substituent, the first substituent linked to the first nitrogen atom constituting the fused ring (e.g., fused ring core). The first substituent may include the first biphenyl ring. The first biphenyl ring may have a structure in which the first benzene ring linked to the first nitrogen atom is linked to the second benzene ring which is linked to the ortho-position carbon with respect to the carbon atom linked to the first nitrogen atom among carbon atoms constituting the first benzene ring. In some embodiments, the first substituent may include the first ring which is fused with or linked to the first biphenyl ring. Accordingly, the fused polycyclic compound of one or more embodiments may effectively maintain a trigonal planar structure of the boron atom through the steric hindrance effect due to the first 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 light emitting element. According to the present disclosure, the fused polycyclic compound represented by Formula 1 includes the first 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 one or more embodiments, the fused polycyclic compound of one or more embodiments may have an increase in the luminous efficiency because the intermolecular interaction may be suppressed or reduced by the introduction of the first substituent, thereby controlling the formation of excimer or exciplex. In one or more embodiments, the fused polycyclic compound of one or more embodiments includes the first substituent, thereby a dihedral angle between the plane containing the fused ring core structure having the boron atom at the center thereof and the plane containing the first substituent may increase, and thus the intermolecular distance increases so that there is an effect of reducing 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, 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 one or more embodiments 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 one or more embodiments is applied to the emission layer EML of the light emitting element ED, the luminous efficiency may be increased and the device service life may also be improved.
The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes the second substituent having electron donor properties, and thus may have an increase in multiple resonance effects and have a low ΔEST, which is a difference between a lowest triplet energy level (T1 level) of the fused polycyclic compound and a lowest singlet energy level (S1 level) of the fused polycyclic compound. Accordingly, because reverse intersystem crossing (RISC) from the triplet excited state to the singlet excited state easily occurs, delayed fluorescence characteristics may be enhanced, thereby improving the luminous efficiency. In addition, the fused polycyclic compound represented by Formula 1 according to one or more embodiments includes the second substituent at a particular position, and thus a deep blue emission color may be provided. The second substituent includes a carbazole moiety or a diphenylamine moiety having electron donor properties, and is substituted at the para-position with respect to the first heteroatom of the fused polycyclic compound, and thus allows the fused polycyclic compound represented by Formula 1 to have a low singlet energy level (S1). Therefore, the fused polycyclic compound represented by Formula 1 may cause a blue shift of the emission wavelength, and thus when the fused polycyclic compound is applied as a dopant in the emission layer of the light emitting element, high luminous efficiency and high color purity may be achieved. Moreover, the emission wavelength of about several nanometers to about several score nanometers may be easily controlled or selected according to the type or kind of the second substituent and/or the type or kind of substituent substituted at the second substituent. For example, the fused polycyclic compound of one or more embodiments includes an oxygen atom, a sulfur atom, or a nitrogen atom as the first heteroatom, and a structure in which the second substituent is substituted at the para-position with respect to the first heteroatom, and thus the emission wavelength may be blue-shifted and at the same time may be controlled or selected finely. For example, the fused polycyclic compound of one or more embodiments may be controlled to have a desired or suitable emission wavelength within a blue light wavelength range while the optical and physical properties are not greatly changed.
The emission spectrum of the fused polycyclic compound represented by Formula 1 of one or more embodiments has a full width of half maximum (FWHM) of about 10 nm to about 50 nm, or a FWHM of about 20 nm to about 40 nm. The emission spectrum of the fused polycyclic compound, as a first dopant, represented by Formula 1 of one or more embodiments has the above range of FWHM, thereby improving luminous efficiency when applied to a light emitting element. In one or more embodiments, when the fused polycyclic compound of one or more embodiments is utilized as a blue light emitting element material for the light emitting element, the element service life may be improved.
The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a thermally activated delayed fluorescence emitting material. Furthermore, the fused polycyclic compound represented by Formula 1 of one or more embodiments may be a thermally activated delayed fluorescence dopant having a difference (ΔEST) between the lowest triplet exciton energy level (T1 level) and the lowest singlet exciton energy level (S1 level) of about 0.6 eV or less. In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescence dopant having the difference (ΔEST) between a lowest triplet exciton energy level (T1 level) and a lowest singlet exciton energy level (S1 level) of 0.2 eV or less.
The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a luminescent material having a luminescence center wavelength in a wavelength region of about 430 nm to about 490 nm. For example, in one or more embodiments, the fused polycyclic compound represented by Formula 1 may be a blue thermally activated delayed fluorescence (TADF) dopant. However, embodiments of the present disclosure are not limited thereto, when the fused polycyclic compound of one or more embodiments is utilized as a luminescent material, the first dopant may be utilized as a dopant material that emits light in one or more suitable wavelength regions, such as a red emitting dopant or a green emitting dopant.
The emission layer EML in the light emitting element ED of one or more embodiments may be to emit delayed fluorescence. For example, in some embodiments, the emission layer EML may be to emit thermally activated delayed fluorescence (TADF).
In some embodiments, the emission layer EML of the light emitting element ED may be to emit blue light. For example, the emission layer EML of the organic electroluminescence element ED (i.e., light emitting element ED) of one or more embodiments may be to emit blue light in the wavelength range of about 490 nm or less. However, embodiments of the present disclosure are not limited thereto, for example, the emission layer EML may be to emit green light or red light.
In one or more embodiments, the fused polycyclic compound of one or more embodiments may be included in the emission layer EML. The fused polycyclic compound of one or more embodiments may be included as a dopant material in the emission layer EML. The fused polycyclic compound of one or more embodiments may be a thermally activated delayed fluorescence material. The fused polycyclic compound of one or more embodiments may be utilized as a thermally activated delayed fluorescence dopant. For example, in the light emitting element ED of one or more embodiments, the emission layer EML may include, as a thermally activated delayed fluorescence dopant, at least one selected from among the fused polycyclic compounds represented in Compound Group 1 as described above. However, a utilization of the fused polycyclic compound of one or more embodiments is not limited thereto.
In one or more embodiments, the emission layer EML may include multiple compounds. The emission layer EML of one or more embodiments may include the fused polycyclic compound represented by Formula 1, i.e., the first compound, and at least one selected from among a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.
In one or more embodiments, the emission layer EML may include the first compound represented by Formula 1 and further include at least one selected from among a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1.
In one or more embodiments, the emission layer EML may include a second compound represented by Formula HT-1. In one or more embodiments, the second compound may be utilized as a hole transport host material in the emission layer EML.
In Formula HT-1, A1 to A8 may each independently be N or CR51. For example, in some embodiments, all A1 to A8 may be CR51. In some embodiments, any one selected from among A1 to A8 may be N, and the remainder may be CR51.
In Formula HT-1, L1 may be a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms. For example, in some embodiments, 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, and/or the like, but embodiments of the present disclosure are not limited thereto.
In Formula HT-1, Ya may be a direct linkage, CR52R53, or SiR54R55. For example, it may refer to that two benzene rings connected with the nitrogen atom of Formula HT-1 may be connected via a direct linkage,
In Formula HT-1, when Ya is a direct linkage, the compound represented by Formula HT-1 may include a carbazole moiety.
In Formula HT-1, Ar1 may be a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. For example, in some embodiments, 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, and/or the like, but embodiments of the present disclosure are not limited thereto.
In Formula HT-1, R51 to R55 may each independently be hydrogen, deuterium, a halogen, 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 of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms. In some embodiments, one or more selected from among R51 to R55 may be combined with an adjacent group to form a ring. For example, in some embodiments, R51 to R55 may each independently be hydrogen or deuterium. In some embodiments, R51 to R55 may each independently be an unsubstituted methyl group or an unsubstituted phenyl group.
In one or more embodiments, the second compound represented by Formula HT-1 may be represented by any one selected from among compounds represented in Compound Group 2. The emission layer EML may include at least one selected from among the compounds represented in Compound Group 2 as a hole transport host material.
In the example compounds in Compound Group 2, “D” refers to deuterium, and “Ph” may refer to a substituted or unsubstituted phenyl group. For example, in the example compounds in Compound Group 2, “Ph” may be an unsubstituted phenyl group.
In one or more embodiments, the emission layer EML may include a third compound represented by Formula ET-1. For example, in one or more embodiments, the third compound may be utilized as an electron transport host material in the emission layer EML.
In Formula ET-1, at least one selected from among X1 to X3 may be N, and the remainder may be CR56. For example, in some embodiments, one selected from among X1 to X3 may be N, and the remainder two may each independently be CR56. In these embodiments, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, two selected from among X1 to X3 may be N, and the remainder may be CR56. In these embodiments, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X1 to X3 may be all N. In these embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.
In Formula ET-1, R56 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms.
In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.
In Formula ET-1, Ar2 to Ar4 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. For example, in some embodiments, Ar2 to Ar4 may be substituted or unsubstituted phenyl groups or substituted or unsubstituted carbazole groups.
In Formula ET-1, L2 to L4 may each independently be a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms. In some embodiments, when each of b1 to b3 is an integer of 2 or more, L2's to L4's may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms.
In one or more embodiments, the third compound may be represented by any one selected from among compounds in Compound Group 3. The light emitting element ED of one or more embodiments may include any one selected from among the compounds in Compound Group 3.
In the example compounds in Compound Group 3, “D” refers to deuterium, and “Ph” refers to an unsubstituted phenyl group.
In one or more embodiments, the emission layer EML may include the second compound and the third compound, and the second compound and the third compound may form exciplex. In the emission layer EML, exciplex may be formed by a hole transport host and an electron transport host. In this case, the triplet energy of the exciplex formed by the hole transport host and the electron transport host may correspond to a difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.
For example, in one or more embodiments, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole transport host and the electron transport host may be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy of the exciplex may be a smaller value than the energy gap of each host material. The exciplex may have a triplet energy of about 3.0 eV or less, that is the energy gap between the hole transport host and the electron transport host.
In one or more embodiments, the emission layer EML may include a fourth compound in addition to the first compound to the third compound. The fourth compound may be utilized as a phosphorescence sensitizer of the emission layer EML. Because energy may transfer from the fourth compound to the first compound, light emission may arise.
For example, in one or more embodiments, the emission layer EML may include an organometallic complex including platinum (Pt) as a central metal atom and ligands bonded to the central metal atom, as the fourth compound. In the light emitting element ED of one or more embodiments, the emission layer EML may include a compound represented by Formula D-1 as the fourth compound.
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 of 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle of 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 alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms. In L11 to L13, “” refers to a part connected with 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 be unconnected. When b2 is 0, C2 and C3 may be unconnected. When b3 is 0, C3 and C4 may be unconnected.
In Formula D-1, R61 to R66 may each independently be hydrogen, deuterium, a halogen, 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 of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms. In some embodiments, one or more selected from among R61 to R66 may be combined with an adjacent group to form a ring. In some embodiments, R61 to R66 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 d1 to d4 each are 0, the fourth compound may be unsubstituted with corresponding R61 to R64. A case (e.g., embodiments) where d1 to d4 each are 4, and R61 to R64 are hydrogens, may be the same as a case (e.g., embodiments) where d1 to d4 each are 0. When d1 to d4 are integers of 2 or more, each of multiple R61's to R64's may be all the same, or at least one selected from among multiple R61's to R64's may be different.
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 selected from among C-1 to C-4.
In C-1 to C-4, P1 may be C or CR74, P2 may be N
or NR81, P3 may be N
or NR82, and P4 may be C
or CR88. R71 to R88 may each independently be a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring.
In C-1 to C-4,
is a part connected with a central metal atom of Pt, and “” corresponds to a part connected with an adjacent ring group (C1 to C4) or linker (L11 to L13).
The emission layer EML of one or more embodiments may include the first compound that is a fused polycyclic compound of the present disclosure, and at least one selected from among the second to fourth compounds. For example, in some embodiments, 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 exciplex, and via the exciplex, energy transfer to the first compound may arise, and light emission may arise.
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 exciplex, and via the exciplex, energy transfer to the fourth compound and the first compound may arise, and light emission may arise. In some embodiments, the fourth compound may be a sensitizer. In the light emitting element ED of one or more embodiments, the fourth compound included in the emission layer EML may act as a sensitizer and may play the role of transferring energy from a host to the first compound that is a light-emitting dopant. For example, the fourth compound that plays the role of an auxiliary dopant may accelerate energy transfer to the first compound that is a light emitting dopant and increase the light emitting ratio of the first compound. Accordingly, the emission efficiency of the emission layer EML of one or more embodiments may be improved. In some embodiments, when the energy transfer to the first compound increases, excitons formed in the emission layer EML may not be accumulated but rapidly emit light, and the deterioration of a device may be reduced. As a result, the lifetime of the light emitting element ED of one or more embodiments may increase.
The light emitting element ED of one or more embodiments 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 element ED of one or more embodiments, the emission layer EML may include the second compound and the third compound, which are two different hosts, the first compound which emits delayed fluorescence, and the fourth compound including an organometallic complex, concurrently (e.g., simultaneously), and may show excellent or suitable emission efficiency properties.
In one or more embodiments, the fourth compound represented by Formula D-1 may be at least one selected from among compounds represented in Compound Group 4. The emission layer EML may include at least one selected from among the compounds represented in Compound Group 4 as a sensitizer material.
In the example compounds in Compound Group 4, “D” refers to deuterium.
In one or more embodiments, the light emitting device ED of one or more embodiments may include multiple emission layers. Multiple emission layers may be stacked in order and provided, and for example, a light emitting element ED including multiple emission layers may be to emit white light (e.g., combined white light). The light emitting element including multiple emission layers may be a light emitting element of a tandem structure. When the light emitting element ED includes multiple emission layers, at least one emission layer EML may include the first compound represented by Formula 1 of one or more embodiments. In some embodiments, when the light emitting element ED includes multiple 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. In the light emitting device ED of one or more embodiments, when the emission layer EML includes all of the first compound, the second compound, and the third compound, the amount of the first compound may be about 0.1 wt % to about 5 wt % based on the total weight of the first compound, the second compound, and the third compound. However, embodiments of the present disclosure are not limited thereto. When the amount of the first compound satisfies the above-described ratio, energy transfer from the second compound and the third compound to the first compound may increase, and accordingly, the emission efficiency and device lifetime may increase.
In the emission layer EML, the total amount of the second compound and the third compound may be the remaining amount excluding the amount of the first compound. For example, the total amount of the second compound and the third compound may be about 65 wt % to about 95 wt % based on the total weight of the first compound, the second compound, and the third compound.
In the total amount 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 total amount of the second compound and the third compound satisfies the above-described ratio, charge balance properties in the emission layer EML may be improved, and emission efficiency and device lifetime may be improved and/or increased. When the total amount of the second compound and the third compound deviates from the above-described ratio range, charge balance in the emission layer EML may be broken, emission efficiency may be degraded and/or decreased, and the device may be easily deteriorated.
In one or more embodiments, when the emission layer EML includes the fourth compound, the amount of the fourth compound may be about 4 wt % to 30 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound in the emission layer EML. However, embodiments of the present disclosure are not limited thereto. When the amount of the fourth compound satisfies the above-described amount, energy transfer from a host to the first compound that is a light emitting dopant may increase, and emission ratio may be improved. Accordingly, the emission efficiency of the emission layer EML may be improved. When the amount ratio of the first compound, the second compound, the third compound, and the fourth compound, included in the emission layer EML satisfies the above-described amount ratio, excellent or suitable emission efficiency and long lifetime of the light emitting element may be achieved.
In the light emitting element ED of one or more embodiments, the emission layer EML may further include at least one of anthracene derivatives, pyrene derivatives, fluoranthene derivatives, chrysene derivatives, dihydrobenzanthracene derivatives, or triphenylene derivatives. For example, in some embodiments, the emission layer EML may include one or more anthracene derivatives and/or one or more pyrene derivatives.
In the light emitting elements ED of one or more embodiments, shown in
In Formula E-1, R31 to R40 may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring. In some embodiments, one or more selected from R31 to R40 may be combined with an adjacent group to form a saturated hydrocarbon ring, 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.
The compound represented by Formula E-1 may be any one selected from among Compound E1 to Compound E19.
In one or more embodiments, 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 phosphorescence host material.
In Formula E-2a, “a” may be an integer of 0 to 10, La may be a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms. In some embodiments, when “a” is an integer of 2 or more, multiple La's may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 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 hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or may be combined with an adjacent group to form a ring. In some embodiments, one or more selected from among Ra to Ri may be combined with an adjacent group to form a hydrocarbon ring or a heterocycle including N, O, S, etc. as a ring-forming atom.
In some embodiments, in Formula E-2a, two or three selected from A1 to A5 may be N, and the remainder may be CRi.
In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group of 6 to 30 ring-forming carbon atoms. Lb may be a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 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, multiple Lb's may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms.
The compound represented by Formula E-2a or Formula E-2b may be any one selected from among compounds in Compound Group E-2. However, the compounds shown in Compound Group E-2 are only examples, and the compound represented by Formula E-2a or Formula E-2b is not limited to the compounds represented in Compound Group E-2.
In one or more embodiments, the emission layer EML may further include a material well-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, embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinolinato)aluminum (Alq3), 9,10-di(naphthalen-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 the host material.
In one or more embodiments, the emission layer EML may include a compound represented by Formula M-a. The compound represented by Formula M-a may be utilized as a phosphorescence dopant material.
In Formula M-a, Y1 to Y4, and Z1 to Z4 may each independently be CR1 or N, and R1 to R4 may each independently be hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or may be combined with 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 phosphorescence dopant.
The compound represented by Formula M-a may be any one selected from among Compounds M-a1 to M-a25. However, Compounds M-a1 to M-a25 are mere examples, and the compound represented by Formula M-a is not limited to the compounds represented by Compounds M-a1 to M-a25.
In one or more embodiments, the emission layer EML may further include a compound represented by any one selected from among Formula F-a to Formula F-c. The compounds represented by Formula F-a to Formula F-c may be utilized as fluorescence dopant materials.
In Formula F-a, two selected from Ra to Rj may each independently be substituted with *—NAr1Ar2. The remainder not substituted with *—NAr1Ar2 among Ra to Rj may each independently be hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. In *—NAr1Ar2, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. For example, in some embodiments, at least one selected from among Ar1 and Ar2 may be a heteroaryl group including O or S as a ring-forming atom.
In Formula F-b, Ra and Rb may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or may be combined with an adjacent group to form a ring. Ar1 to Ar4 may each independently be a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.
In Formula F-b, U and V may each independently be a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocycle of 2 to 30 ring-forming carbon atoms. In some embodiments, at least one selected from among Ar1 to Ar4 may be a heteroaryl group including 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 forms a fused ring at the designated part by U or V, and when the number of U or V is 0, a ring is not present at the designated part 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, a fused ring having the fluorene core of Formula F-b may be a ring compound with four rings. In some embodiments, when the number of both (e.g., simultaneously) U and V is 0, the fused ring of Formula F-b may be a ring compound with three rings. In some embodiments, when the number of both (e.g., simultaneously) U and V is 1, a fused ring having the fluorene core of Formula F-b may be a ring compound with five rings.
In Formula F-c, A1 and A2 may each independently be O, S, Se, or NRm, and Rm may be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. R1 to R11 may each independently be hydrogen, deuterium, a halogen, 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 thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring.
In Formula F-c, A1 and A2 may each independently be combined with the substituents of an adjacent ring to form a fused ring. For example, when A1 and A2 may each independently be NRm, A1 may be combined with R4 or R5 to form a ring. In some embodiments, A2 may be combined with R7 or R8 to form a ring.
In one or more embodiments, the emission layer EML may include as a suitable dopant material, one or more selected from styryl derivatives (for example, 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-phenylbenzenamine (N-BDAVBi), and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and the derivatives thereof (for example, 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and the derivatives thereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene, and 1,4-bis(N,N-diphenylamino)pyrene), etc.
In one or more embodiments, the emission layer EML may include a suitable phosphorescence dopant material. For example, the phosphorescence dopant may utilize a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). For example, iridium(III) bis(4,6-difluorophenylpyridinato-N,C2′)picolinate (Firpic), bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (Fir6), or platinum octaethyl porphyrin (PtOEP) may be utilized as the phosphorescence dopant. However, embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the emission layer may include quantum dot(s).
In the present disclosure, the quantum dot refers to a crystal of a semiconductor compound. The quantum dot may be to emit light having one or more suitable emission wavelengths depending on the size of crystal. The quantum dot may be to emit light having one or more suitable emission wavelengths as the elemental ratio in the quantum dot compound is adjusted.
The quantum dot may have a diameter of, for example, about 1 nm to about 10 nm. In the present disclosure, when dots or dot particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the dot or dot particles are non-spherical, the “diameter/size” indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, a similar process thereto, and/or the like.
The wet chemical process is a method in which a precursor material of a quantum dot is mixed with an organic solvent to grow quantum dot particle crystals. When the crystals grow, the organic solvent naturally may act as a dispersant coordinated on the surface of the quantum dot crystals and control the growth of the crystals. Thus, the wet chemical process may control the growth of quantum dot particles through a process which is more easily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), and which is performed at low costs.
In one or more embodiments, the emission layer EML may include a quantum dot material. In one or more embodiments, the quantum dot material may have a core/shell structure. The core of the quantum dot may be selected from a II-VI group compound, a III-VI group compound, a I-III-VI group compound, a III-V group compound, a III-II-V group compound, a IV-VI group compound, a IV group element, a IV group compound, and combinations thereof.
The Group II-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, and a mixture thereof. In some embodiments, the Group II-VI compound may further include a Group I metal and/or a Group IV element. The Group I-II-VI compound may be selected from CuSnS and/or CuZnS, and the Group II-IV-VI compound may be selected from ZnSnS and/or the like. The Group I-II-IV-VI compound may be selected from quaternary compounds selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and a mixture thereof.
The III-VI group compound may include a binary compound such as In2S3 and/or In2Se3, a ternary compound such as InGaS3 and/or InGaSe3, or one or more combinations thereof.
The I-III-VI group compound may be selected from a ternary compound selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof, and/or a quaternary compound such as AgInGaS2 and/or CuInGaS2.
The III-V group 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 mixtures 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 mixtures 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 mixtures thereof. In some embodiments, the III-V group compound may further include a II group metal. For example, InZnP, etc. may be selected as a III-II-V group 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 II-IV-V compound may be selected from a ternary compound selected from the group consisting of ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, and CdGeP2, 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.
Each element included in the multi-element compound such as the binary compound, ternary compound, and quaternary compound may be present in particles at a substantially uniform concentration or a non-substantially uniform concentration. For example, Formula above indicates the types (kinds) of elements included in a compound, and element ratios in the compound may be different. For example, AgInGaS2 may indicate AgInxGa1-xS2 (x is a real number between 0 and 1).
In one or more embodiments, the binary compound, the ternary compound, or the quaternary compound may be present at substantially uniform concentration in a particle or may be present at a partially different concentration distribution within the same particle. In some embodiments, a core/shell structure in which one quantum dot wraps another quantum dot may be desirable. The interface of the core and the shell may have a concentration gradient in which the concentration of an element present in the shell is decreased toward the center.
In some embodiments, the quantum dot may have the above-described core-shell structure including a core including a nanocrystal and a shell wrapping the core. The shell of the quantum dot may play the role of a protection layer for preventing or reducing the chemical deformation of the core to maintain semiconductor properties and/or a charging layer for imparting the quantum dot with electrophoretic properties. The shell may have a single layer or a multilayer. Examples of the shell of the quantum dot may include a metal or non-metal oxide, a semiconductor compound, or combinations thereof.
For example, the metal or non-metal oxide for the shell may include a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO, and/or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4, but embodiments of the present disclosure are not limited thereto.
Also, the semiconductor compound suitable as a shell 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 embodiments of the present disclosure are not limited thereto.
The quantum dot may have a full width of half maximum (FWHM) of emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or, about 30 nm or less. Within this range, the color purity or color reproducibility of the light emitting element may be improved. In some embodiments, light emitted via such quantum dots is emitted in all directions, and light view angle properties may be improved.
In some embodiments, the shape of the quantum dot may be generally utilized shapes in the art, without specific limitation. In one or more embodiments, the shape of spherical nanoparticle, pyramidal nanoparticle, multi-arm nanoparticle, or cubic nanoparticle, nanotube, nanowire, nanofiber, nanoplate particle, etc. may be utilized.
As the size of the quantum dot or the ratio of elements in the quantum dot compound is regulated, the energy band gap of the quantum dot may be accordingly controlled or selected to obtain light of one or more suitable wavelengths from a quantum dot emission layer. Therefore, by utilizing the quantum dots as described above (e.g., utilizing quantum dots of different sizes or having different element ratios in the quantum dot compound), a light emitting device emitting light of one or more suitable wavelengths may be obtained. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound may be regulated to emit red, green, and/or blue light. In some embodiments, the quantum dots may be configured to emit white light by combining light of one or more suitable colors.
In the light emitting elements ED of one or more embodiments, as shown in
The electron transport region ETR may have a single layer formed utilizing a single material, a single layer formed utilizing multiple different materials, or a multilayer structure having multiple layers formed utilizing multiple different materials.
For example, in some embodiments, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or a single layer structure formed utilizing an electron injection material and an electron transport material. Further, in some embodiments, the electron transport region ETR may have a single layer structure formed utilizing multiple different materials, or a structure stacked from the emission layer EML of electron transport layer ETL/electron injection layer EIL, or hole blocking layer HBL/electron transport layer ETL/electron injection layer EIL, without limitation. A thickness of the electron transport region ETR may be, for example, from about 1,000 Å to about 1,500 Å.
The electron transport region ETR may be formed utilizing one or more suitable methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and/or a laser induced thermal imaging (LITI) method.
In one or more embodiments, the electron transport region ETR may include a compound represented by Formula ET-2.
In Formula ET-2, at least one selected from among X1 to X3 may be N, and the remainder are CRa. Ra may be hydrogen, deuterium, a substituted or unsubstituted alkyl of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms. Ar1 to Ar3 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.
In Formula ET-2, “a” to “c” may each independently be an integer of 0 to 10. In Formula ET-2, L1 to L3 may each independently be a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms. In some embodiments, when “a” to “c” are integers of 2 or more, L1's to L3's may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms.
In one or more embodiments, the electron transport region ETR may include an anthracene-based compound. However, embodiments of the present disclosure are not limited thereto, for example, in some embodiments, the electron transport region ETR may include, for example, at least one selected from among 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-phenylbenzimidazolyl-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-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-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(naphthalen-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and mixtures thereof, without limitation.
In one or more embodiments, the electron transport region ETR may include at least one selected from among Compounds ET1 to ET36.
In some embodiments, the electron transport region 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-depositing material of the metal halide and the lanthanide metal. For example, in some embodiments, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc., as the co-depositing material. In some embodiments, the electron transport region ETR may utilize a metal oxide such as Li2O and/or BaO, or 8-hydroxy-lithium quinolate (Liq). However, embodiments of the present disclosure are not limited thereto. In some embodiments, the electron transport region ETR also may be formed utilizing a mixture material of an electron transport material and an insulating organo metal salt. The organo metal salt may be a material having an energy band gap of about 4 eV or more. For example, the organo metal salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and/or metal stearates.
In one or more embodiments, the electron transport region ETR may 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 aforementioned materials. However, embodiments of the present disclosure are not limited thereto.
The electron transport region ETR may include the compounds of the electron transport region in at least one selected from among an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL.
When the electron transport region ETR includes an electron transport layer ETL, a thickness of the electron transport layer ETL may be from about 100 Å to about 1,000 Å, for example, from about 150 Å to about 500 Å. When the thickness of the electron transport layer ETL satisfies the above-described range, satisfactory electron transport properties may be obtained without a substantial increase in driving voltage. When the electron transport region ETR includes an electron injection layer EIL, a thickness of the electron injection layer EIL may be from about 1 Å to about 100 Å, or from about 3 Å to about 90 Å. When the thickness of the electron injection layer EIL satisfies the above described range, satisfactory electron injection properties may be obtained without inducing a substantial increase in driving voltage.
The second electrode EL2 may be 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 embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second cathode 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 include a transparent metal oxide, for example, ITO, IZO, ZnO, 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, compounds thereof, or mixtures thereof (for example, AgMg, AgYb, or MgYb). In some embodiments, the second electrode EL2 may have a multilayered structure including a reflective layer or a transflective layer formed utilizing one or more selected from the above-described materials and a transparent conductive layer formed utilizing ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include one selected from the aforementioned metal materials, combinations of two or more metal materials selected from the aforementioned metal materials, or oxides of the aforementioned metal materials.
In some embodiments, 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 decrease.
In some embodiments, on the second electrode EL2 in the light emitting element ED of one or more embodiments, a capping layer CPL may be further disposed. The capping layer CPL may include a multilayer or a single layer.
In one or more embodiment, the capping layer CPL may be an organic layer or an inorganic layer. For example, in some embodiments, when the capping layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF2, SiON, SiNx, SiOy, etc.
For example, in some embodiments, when the capping layer CPL includes an organic material, the organic material may include 2,2′-dimethyl-N,N′-di-[(1-naphthyl)-N,N′-diphenyl]-1,1′-biphenyl-4,4′-diamine (α-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-9-yl) triphenylamine (TCTA), etc., and/or may include an epoxy resin and/or acrylate such as methacrylate. In some embodiments, the capping layer CPL may include at least one selected from among Compounds P1 to P5, but embodiments of the present disclosure are not limited thereto.
In some embodiments, the refractive index of the capping layer CPL may be about 1.6 or more. For example, in one or more embodiments, the refractive index of the capping layer CPL with respect to light in a wavelength range of about 550 nm to about 660 nm may be about 1.6 or more.
Referring to
The light emitting device ED may include a first electrode EL1, a hole transport region HTR on the first electrode EL1, an emission layer EML on the hole transport region HTR, an electron transport region ETR on the emission layer EML, and a second electrode EL2 on the electron transport region ETR. In one or more embodiments, the same structures as the light emitting elements of
The emission layer EML of the light emitting device ED included in the display device DD-a according to one or more embodiments may include the fused polycyclic compound of one or more embodiments described above.
Referring to
The light controlling layer CCL may be disposed on the display panel DP. The light controlling layer CCL may include a light converter. The light converter may be a quantum dot and/or a phosphor. The light converter may transform the wavelength of light provided and then emit. For example, the light controlling layer CCL may be a layer including a quantum dot or a layer including a phosphor.
The light controlling layer CCL may include multiple light controlling parts CCP1, CCP2, and CCP3. The light controlling parts CCP1, CCP2, and CCP3 may be separated and apart from one another.
Referring to
The light controlling layer CCL may include a first light controlling part CCP1 including a first quantum dot QD1 converting first color light provided from the light emitting device ED into second color light, a second light controlling part CCP2 including a second quantum dot QD2 converting first color light into third color light, and a third light controlling part CCP3 transmitting first color light. In one or more embodiments, the first light controlling part CCP1 may provide red light which is the second color light, and the second light controlling part CCP2 may provide green light which is the third color light. The third color controlling part CCP3 may be to transmit and provide blue light which is the first color light provided from the light emitting device ED. For example, in some embodiments, the first quantum dot QD1 may be a red quantum dot to emit red light, and the second quantum dot QD2 may be a green quantum dot to emit green light. On the quantum dots QD1 and QD2, the same content as those described above may be applied.
In some embodiments, the light controlling layer CCL may further include a scatterer SP. The first light controlling part CCP1 may include the first quantum dot QD1 and the scatterer SP, the second light controlling part CCP2 may include the second quantum dot QD2 and the scatterer SP, and the third light controlling part CCP3 may not include a (e.g., may exclude any) quantum dot but include the scatterer SP.
The scatterer SP may be an inorganic particle. For example, the scatterer SP may include at least one selected from among TiO2, ZnO, Al2O3, SiO2, and hollow silica. In one or more embodiments, the scatterer SP may include at least one selected from among TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of two or more materials selected from among TiO2, ZnO, Al2O3, SiO2, and hollow silica.
The first light controlling part CCP1, the second light controlling part CCP2, and the third light controlling part CCP3 may respectively include base resins BR1, BR2, and BR3 dispersing the quantum dots QD1 and QD2 and the scatterer SP. In one or more embodiments, the first light controlling part CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in a first base resin BR1, the second light controlling part CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in a second base resin BR2, and the third light controlling part CCP3 may include the scatterer particle SP dispersed in a third base resin BR3.
The base resins BR1, BR2, and BR3 are mediums in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be composed 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 each independently be acrylic resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In some embodiments, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same or different from each other.
In one or more embodiments, the light controlling layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may play the role of blocking the penetration of moisture and/or oxygen (hereinafter, will be referred to as “humidity/oxygen”). The barrier layer BFL1 may block or reduce the exposure of the light controlling parts CCP1, CCP2, and CCP3 to humidity/oxygen. In some embodiments, the barrier layer BFL1 may cover the light controlling parts CCP1, CCP2, and CCP3. In some embodiments, a color filter layer CFL, which will be explained later, may include a barrier layer BFL2 disposed on the light controlling parts CCP1, CCP2, and CCP3.
The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, in some embodiments, the barrier layers BFL1 and BFL2 may each independently be formed by including an inorganic material. For example, the barrier layers BFL1 and BFL2 may each independently be formed by including one or more selected from silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, and a metal thin film securing light transmittance. In some embodiments, the barrier layers BFL1 and BFL2 may each further include an organic layer. The barrier layers BFL1 and BFL2 may each be composed of a single layer or multiple layers.
In the display apparatus DD-a of one or more embodiments, the color filter layer CFL may be disposed on the light controlling layer CCL. For example, the color filter layer CFL may be disposed directly on the light controlling layer CCL. In these embodiments, the barrier layer BFL2 may not be provided.
The color filter layer CFL may include filters CF1, CF2, and CF3. Each of the first to third filters CF1, CF2, and CF3 may be disposed corresponding to a red luminous area PXA-R, a green luminous area PXA-G, and a blue luminous area PXA-B, respectively.
The color filter layer CFL may include a first filter CF1 transmitting the second color light, a second filter CF2 transmitting the third color light, and a third filter CF3 transmitting the first color light. For example, in some embodiments, 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. Each of the filters CF1, CF2, and CF3 may include a polymer 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.
However, embodiments of the present disclosure are not limited thereto, and the third filter CF3 may not include the (e.g., may exclude any) pigment and/or dye. The third filter CF3 may include a polymer photosensitive resin and not include the pigment and/or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed utilizing a transparent photosensitive resin.
In some embodiments, the first filter CF1 and the second filter CF2 may each be yellow filters. In some embodiments, the first filter CF1 and the second filter CF2 may be provided in one body without distinction.
In one or more embodiments, the color filter layer CFL may further include a light blocking part. The light blocking part may be a black matrix. The light blocking part may be formed by including an organic light blocking material and/or an inorganic light blocking material including a black pigment and/or black dye. The light blocking part may prevent or reduce light leakage phenomenon and divide the boundaries among adjacent filters CF1, CF2, and CF3.
On the color filter layer CFL, a base substrate BL may be disposed/provided. The base substrate BL may be a member providing a base surface on which the color filter layer CFL, the light controlling layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, the base substrate BL may not be provided.
For example, in some embodiments, the light emitting device ED-BT included in the display apparatus DD-TD may be a light emitting device of a tandem structure including multiple emission layers.
In one or more embodiments shown in
Between neighboring light emitting structures OL-B1, OL-B2, and OL-B3, charge generating layers CGL1 and CGL2 may be disposed. The charge generating layers CGL1 and CGL2 may include a p-type or kind charge (e.g., P-charge) generating layer and/or an n-type or kind charge (e.g., N-charge) generating layer.
At least one selected from among the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display device DD-TD of one or more embodiments may include the above-described fused polycyclic compound of one or more embodiments. For example, at least one selected from among the plurality of emission layers included in the light emitting device ED-BT may include the fused polycyclic compound of one or more embodiments.
Referring to
In one or more embodiments, 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 addition, the third light emitting device ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. 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, an emission auxiliary part OG may be disposed.
The emission auxiliary part OG may include a single layer or a multilayer. The emission auxiliary part OG may include a charge generating layer. In one or more embodiments, the emission auxiliary part OG may include an electron transport region, a charge generating layer, and a hole transport region stacked in order (e.g., in the stated order). The emission auxiliary part OG may be provided as a common layer in all of the first to third light emitting devices ED-1, ED-2, and ED-3. However, embodiments of the present disclosure are not limited thereto, and the emission auxiliary part OG may be patterned and provided in an opening part OH defined in a pixel definition layer PDL.
The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may each 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 each be disposed between the emission auxiliary part OG and the hole transport region HTR.
For example, in one or more embodiments, the first light emitting device ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary part OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2, stacked in order (e.g., in the stated order). The second light emitting device ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary part OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2, stacked in order (e.g., in the stated order). The third light emitting device ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary part OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2, stacked in order (e.g., in the stated order).
In some embodiments, an optical auxiliary layer PL may be disposed on a display device layer DP-ED. The optical auxiliary layer PL may include a polarization layer. The optical auxiliary layer PL may be disposed on a display panel DP and may control reflected light at the display panel DP by external light. In some embodiments, the optical auxiliary layer PL may not be provided in the display apparatus.
In one or more embodiments, at least one emission layer included in the display device DD-b illustrated in
Different from
Charge generating layers CGL1, CGL2, and CGL3 disposed among neighboring light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type or kind charge (e.g., P-charge) generating layer and/or an n-type or kind charge (e.g., N-charge) generating layer.
At least one selected from among the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c according to one or more embodiments may include the fused polycyclic compound of one or more embodiments described above. For example, in one or more embodiments, at least one selected from among the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may include the fused polycyclic compound of one or more embodiments described above.
The light emitting element/device ED described above according to one or more embodiments of the present disclosure includes the fused polycyclic compound of one or more embodiments in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, and may thus exhibit excellent or suitable light emitting efficiency and improved lifespan. For example, the fused polycyclic compound according to one or more embodiments may be included in the emission layer EML of the light emitting element ED of one or more embodiments, and the light emitting element of one or more embodiments may exhibit long lifespan.
In one or more embodiments, an electronic apparatus may include a display apparatus including multiple light emitting devices and a control part controlling the display apparatus. The electronic apparatus of one or more embodiments may be an apparatus activated according to electrical signals. The electronic apparatus may include display apparatuses of one or more suitable embodiments. For example, the electronic apparatus may include at least one selected from televisions, monitors, large-size display apparatuses such as outside billboards, personal computers, laptop computers, personal digital terminals, display apparatuses for automobiles, game consoles, portable electronic devices, and medium- and small-size display apparatuses such as cameras.
In
In one or more embodiments, at least one selected from among the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the light emitting element ED of one or more embodiments as described with reference to
Referring to
A first display apparatus DD-1 may be disposed in a first region overlapping with the steering wheel HA. For example, the first display apparatus DD-1 may be a digital cluster displaying first information of the automobile AM. The first information may include a first graduation showing the travel speed of the automobile AM, a second graduation showing the number of revolution of an engine (i.e., revolutions per minute (RPM)), and images showing a fuel state. The first graduation and second graduation may be represented by digital images.
A second display apparatus DD-2 may be disposed in a second region facing a driver seat and overlapping with the front window GL. The driver seat may be a seat where the steering wheel HA faces. For example, the second display apparatus DD-2 may be a head up display (HUD) showing second information of the automobile AM. The second display apparatus DD-2 may be optically clear. The second information may include digital numbers showing the travel speed of the automobile AM and may further include information including the current time. In some embodiments, the second information of the second display apparatus DD-2 may be projected and displayed on the front window GL.
A third display apparatus DD-3 may be disposed in a third region adjacent to the gear GR. For example, the third display apparatus DD-3 may be a center information display (CID) for the automobile, disposed between a driver seat and a passenger seat and showing third information. The passenger seat may be a seat separated from the driver seat with the gear GR therebetween. The third information may include information on road conditions (for example, navigation information), on playing music or radio, on playing a dynamic image (or image), on the temperature in the automobile AM, and/or the like.
A fourth display apparatus DD-4 may be disposed in a fourth region separated from the steering wheel HA and the gear GR and adjacent to a side of the automobile AM. For example, the fourth display apparatus DD-4 may be a digital wing mirror displaying fourth information. The fourth display apparatus DD-4 may display external images of the automobile AM, taken by a camera module CM disposed at the outside of the automobile AM. The fourth information may include external images of the automobile AM.
The above-described first to fourth information are mere examples, and the first to fourth display apparatuses DD-1, DD-2, DD-3, and DD-4 may further display information on the inside and outside of the automobile. The first to fourth information may include different information from each other. However, embodiments of the present disclosure are not limited thereto, for example, in some embodiments, a portion of the first to fourth information may include the same information.
Hereinafter, with reference to Examples and Comparative Examples, a fused polycyclic compound according to one or more embodiments of the present disclosure and a light emitting element of one or more embodiments will be described in more detail. In addition, Examples described 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 the fused polycyclic compound according to one or more embodiments will be described by illustrating the synthetic methods of Compounds 4, 35, 37, 40, 44, 59, and 90. In addition, the synthetic methods of the fused polycyclic compounds as described herein are only examples, and the synthetic method of the fused polycyclic compound according to one or more embodiments of the present disclosure is not limited to the following examples.
In an Ar atmosphere, toluene (200 mL) and a mixture (100 mL) of EtOH and water in a volume ratio of 1:1 were added to 1,3-dibromo-5-fluorobenzene (25.00 g, 98.46 mmol), (4-(tert-butyl)phenyl)boronic acid (70.12 g, 393.86 mmol), K3PO4 (41.8 g, 196.93 mmol), and Pd(Ph3P)4 (11.38 g, 9.85 mmol), and then the resultant mixture was heated for about 24 hours while maintaining a temperature at about 80° C. The mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 4-1 (22.38 g, yield 74%). The molecular weight of Intermediate 4-1 was about 307 as measured by fast atom bombardment mass spectrometry (FAB MS).
In an Ar atmosphere, Intermediate 4-2 (21 g, 68.36 mmol), 4-chlorophenol (10.55 g, 82.03 mmol), and K2CO3 (42.51 g, 307.61 mmol) were added to 210 mL of N-methyl-2-Pyrrolidinone (NMP), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 180° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 4-2 (25.01 g, yield 88%). The molecular weight of Intermediate 4-2 was about 416 as measured by FAB MS.
In an Ar atmosphere, Intermediate 4-2 (24.01 g, 57.73 mmol), (3s,5s,7s)-adamantan-1-amine (9.17 g, 60.61 mmol), palladium(0) bis(dibenzylideneacetone) (Pd(dba)2) (3.32 g, 5.77 mmol), (tBu)3PHBF4 (3.35 g, 11.55 mmol), and tBuONa (12.76 g, 132.77 mmol) were added to 288 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 4-3 (20.2 g, yield 72%). The molecular weight of Intermediate 4-3 was about 486 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 4-3 (20.00 g, 42.41 mmol), 4′-iodo-1,1′:2′,1″-terphenyl (120.85 g, 339.26 mmol), CuI (8.48 g, 44.53 mmol), and K2CO3 (46.89 g, 339.26 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 4-4 (19.39 g, yield 64%). The molecular weight of Intermediate 4-4 was about 714 as measured by FAB MS.
In an Ar atmosphere, Intermediate 4-4 (19.00 g, 26.6 mmol) was dissolved in o-dichlorobenzene (ODCB) (266 mL), BBr3 (13.33 g, 53.19 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, N, N-diisopropylethylamine (DIPEA) (41.17 g, 319.15 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 4-5 (9.22 g, yield 48%). The molecular weight of Intermediate 4-5 was about 722 as measured by FAB MS.
In an Ar atmosphere, Intermediate 4-5 (5.00 g, 6.92 mmol), 3,6-di-tert-butyl-9H-carbazole (5.8 g, 20.77 mmol), Pd(dba)2 (0.4 g, 0.69 mmol), (tBu)3PHBF4 (0.4 g, 1.38 mmol), and tBuONa (2.66 g, 27.69 mmol) were added to 34 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 4 (5.68 g, yield 85%). The molecular weight of Compound 4 was about 965 as measured by FAB MS.
The purification by sublimation was performed (340° C., 3.3×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, Intermediate 4-1 (10.52 g, 34.24 mmol), 5-chloro-[1,1′-biphenyl]-2-ol (8.41 g, 41.09 mmol), and K2CO3 (21.3 g, 154.1 mmol) were added to 105 mL of NMP, and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 180° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 35-1 (14.32 g, yield 85%). The molecular weight of Intermediate 35-1 was about 492 as measured by FAB MS.
In an Ar atmosphere, Intermediate 35-1 (13.95 g, 28.36 mmol), 3-phenyldibenzo[b,d]furan-4-amine (7.72 g, 29.78 mmol), Pd(dba)2 (1.63 g, 2.84 mmol), (tBu)3PHBF4 (1.65 g, 5.67 mmol), and tBuONa (10.9 g, 113.45 mmol) were added to 141 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 35-2 (16.16 g, yield 85%). The molecular weight of Intermediate 35-2 was about 670 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 35-2 (15.95 g, 23.8 mmol), 4′-iodo-1, 1:2′,1″-terphenyl (67.81 g, 190.38 mmol), CuI (4.76 g, 24.99 mmol), and K2CO3 (26.31 g, 190.38 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 35-3 (12.4 g, yield 58%). The molecular weight of Intermediate 35-3 was about 899 as measured by FAB MS.
In an Ar atmosphere, Intermediate 35-3 (11.78 g, 13.11 mmol) was dissolved in ODCB (131 mL), BBr3 (6.57 g, 26.22 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (20.29 g, 157.32 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 35-4 (5.35 g, yield 45%). The molecular weight of Intermediate 35-4 was about 906 as measured by FAB MS.
In an Ar atmosphere, Intermediate 35-4 (3.75 g, 4.14 mmol), 9H-carbazole (2.08 g, 12.41 mmol), Pd(dba)2 (0.24 g, 0.41 mmol), (tBu)3PHBF4 (0.24 g, 0.83 mmol), and tBuONa (1.59 g, 16.55 mmol) were added to 20 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 35 (3.9 g, yield 91%). The molecular weight of Compound 35 was about 1037 as measured by FAB MS.
The purification by sublimation was performed (350° C., 3.1×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, Intermediate 35-1 (11.85 g, 24.09 mmol), 3-phenylnaphthalen-2-amine (5.55 g, 25.3 mmol), Pd(dba)2 (1.39 g, 2.41 mmol), (tBu)3PHBF4 (1.4 g, 4.82 mmol), and tBuONa (3.47 g, 36.14 mmol) were added to 120 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 37-1 (13.97 g, yield 92%). The molecular weight of Intermediate 37-1 was about 630 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 37-1 (13.55 g, 21.5 mmol), 1-chloro-3-iodobenzene (41.01 g, 172 mmol), CuI (4.3 g, 22.58 mmol), and K2CO3 (23.77 g, 172 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 37-2 (11.79 g, yield 74%). The molecular weight of Intermediate 37-2 was about 741 as measured by FAB MS.
In an Ar atmosphere, Intermediate 37-2 (13.21 g, 17.83 mmol) was dissolved in ODCB (178 mL), BBr3 (8.93 g, 35.67 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (27.61 g, 213.99 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 37-3 (6.27 g, yield 47%). The molecular weight of Intermediate 37-3 was about 749 as measured by FAB MS.
In an Ar atmosphere, Intermediate 37-3 (4.52 g, 5.84 mmol) and 9H-carbazole (2.93 g, 17.51 mmol), Pd(dba)2 (0.34 g, 0.58 mmol), (tBu)3PHBF4 (0.34 g, 1.17 mmol), and tBuONa (2.24 g, 23.34 mmol) were added to 29 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 37 (4.53 g, yield 75%). The molecular weight of Compound 37 was about 1036 as measured by FAB MS.
The purification by sublimation was performed (340° C., 2.8×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, Intermediate 4-1 (10.48 g, 34.11 mmol), 2,4-dichlorophenol (6.67 g, 40.94 mmol), and K2CO3 (21.22 g, 153.51 mmol) were added to 104 mL of NMP, and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 180° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 40-1 (12.44 g, yield 81%). The molecular weight of Intermediate 40-1 was about 450 as measured by FAB MS.
In an Ar atmosphere, Intermediate 40-1 (12.03 g, 26.72 mmol), [1,1′:3′,1″-terphenyl]-2′-amine (6.88 g, 28.06 mmol), Pd(dba)2 (1.54 g, 2.67 mmol), (tBu)3PHBF4 (1.55 g, 5.34 mmol), and tBuONa (3.85 g, 40.08 mmol) were added to 133 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 40-2 (13.14 g, yield 80%). The molecular weight of Intermediate 40-2 was about 615 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 40-2 (12.96 g, 21.09 mmol), 4-iodo-1,1′-biphenyl (47.25 g, 168.69 mmol), CuI (4.22 g, 22.14 mmol), and K2CO3 (23.31 g, 168.69 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 40-3 (7.76 g, yield 48%). The molecular weight of Intermediate 40-3 was about 767 as measured by FAB MS.
In an Ar atmosphere, Intermediate 40-3 (7.35 g, 9.59 mmol) was dissolved in ODCB (96 mL), BBr3 (4.8 g, 19.17 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (14.84 g, 115.02 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 40-4 (2.82 g, yield 38%). The molecular weight of Intermediate 40-4 was about 775 as measured by FAB MS.
In an Ar atmosphere, Intermediate 40-4 (3.75 g, 4.84 mmol), 9H-carbazole (2.43 g, 14.52 mmol), Pd(dba)2 (0.28 g, 0.48 mmol), (tBu)3PHBF4 (0.28 g, 0.97 mmol), and tBuONa (1.86 g, 19.37 mmol) were added to 24 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 40 (4.56 g, yield 91%). The molecular weight of Compound 40 was about 1036 as measured by FAB MS.
The purification by sublimation was performed (350° C., 3.5×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, Intermediate 4-1 (11.22 g, 36.52 mmol), 2,4-dichlorobenzenethiol (7.85 g, 43.83 mmol), and K2CO3 (22.71 g, 164.35 mmol) were added to 112 mL of NMP, and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 180° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 44-1 (14.13 g, yield 83%). The molecular weight of Intermediate 44-1 was about 466 as measured by FAB MS.
In an Ar atmosphere, Intermediate 44-1 (13.51 g, 28.98 mmol), 3-phenyldibenzo[b,d]thiophen-4-amine (8.38 g, 30.42 mmol), Pd(dba)2 (1.67 g, 2.9 mmol), (tBu)3PHBF4 (1.68 g, 5.8 mmol), and tBuONa (4.18 g, 43.46 mmol) were added to 144 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 44-2 (17.61 g, yield 92%). The molecular weight of Intermediate 44-2 was about 661 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 44-2 (16.82 g, 25.46 mmol), 4-iodo-1,1′-biphenyl (57.05 g, 203.66 mmol), CuI (5.09 g, 26.73 mmol), and K2CO3 (28.15 g, 203.66 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 44-3 (12.83 g, yield 62%). The molecular weight of Intermediate 44-3 was about 813 as measured by FAB MS.
In an Ar atmosphere, Intermediate 44-3 (12.66 g, 15.57 mmol) was dissolved in ODCB (156 mL), BBr3 (7.8 g, 31.15 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (24.11 g, 186.88 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 44-4 (5.24 g, yield 41%). The molecular weight of Intermediate 44-4 was about 821 as measured by FAB MS.
In an Ar atmosphere, Intermediate 44-4 (5.21 g, 6.35 mmol), 9H-carbazole (3.18 g, 19.04 mmol), Pd(dba)2 (0.37 g, 0.63 mmol), (tBu)3PHBF4 (0.37 g, 1.27 mmol), and tBuONa (2.44 g, 25.39 mmol) were added to 31 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 44 (5.50 g, yield 80%). The molecular weight of Compound 44 was about 1082 as measured by FAB MS.
The purification by sublimation was performed (365° C., 2.7×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, Intermediate 4-1 (11.22 g, 36.52 mmol), 5-chloro-[1,1′-biphenyl]-2-thiol (0 g, 0 mmol), and K2CO3 (22.71 g, 164.35 mmol) were added to 112 mL of NMP, and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 180° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 59-1 (17.62 g, yield 95%). The molecular weight of Intermediate 59-1 was about 508 as measured by FAB MS.
In an Ar atmosphere, Intermediate 59-1 (17.52 g, 34.49 mmol), phenanthren-4-amine (13.33 g, 68.99 mmol), Pd(dba)2 (1.98 g, 3.45 mmol), (tBu)3PHBF4 (2 g, 6.9 mmol), and tBuONa (7.62 g, 79.34 mmol) were added to 172 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 59-2 (17.97 g, yield 84%). The molecular weight of Intermediate 59-2 was about 620 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 59-2 (17.66 g, 28.47 mmol), 4-iodo-1,1′-biphenyl (63.8 g, 227.78 mmol), CuI (5.69 g, 29.9 mmol), and K2CO3 (31.48 g, 227.78 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 59-3 (12.76 g, yield 58%). The molecular weight of Intermediate 59-3 was about 772 as measured by FAB MS.
In an Ar atmosphere, Intermediate 59-3 (12.33 g, 15.96 mmol) was dissolved in ODCB (160 mL), BBr3 (8 g, 31.92 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (24.71 g, 191.55 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 59-4 (3.49 g, yield 28%). The molecular weight of Intermediate 59-4 was about 780 as measured by FAB MS.
In an Ar atmosphere, Intermediate 59-4 (3.23 g, 3.94 mmol), 9H-carbazole (1.97 g, 11.81 mmol), Pd(dba)2 (0.23 g, 0.39 mmol), (tBu)3PHBF4 (0.23 g, 0.79 mmol), and tBuONa (1.51 g, 15.74 mmol) were added to 19 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 59 (3.92 g, yield 92%). The molecular weight of Compound 59 was about 1082 as measured by FAB MS.
The purification by sublimation was performed (390° C., 2.8×10−3 Pa) to perform device evaluation.
In an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (12 g, 41.09 mmol), 2-phenyldibenzo[b,d]furan-1-amine (11.19 g, 43.15 mmol), Pd(dba)2 (2.36 g, 4.11 mmol), (tBu)3PHBF4 (2.38 g, 8.22 mmol), and tBuONa (5.92 g, 61.64 mmol) were added to 205 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 90-1 (17.2 g, yield 89%). The molecular weight of Intermediate 90-1 was about 470 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 90-1 (14.95 g, 31.78 mmol), 1-chloro-4-iodobenzene (60.63 g, 254.25 mmol), CuI (6.36 g, 33.37 mmol), and K2CO3 (35.14 g, 254.25 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 90-2 (11.26 g, yield 61%). The molecular weight of Intermediate 90-2 was about 581 as measured by FAB MS.
In an Ar atmosphere, Intermediate 90-2 (11.05 g, 19.02 mmol), 2-phenyldibenzo[b,d]furan-1-amine (5.18 g, 19.97 mmol), Pd(dba)2 (1.09 g, 1.9 mmol), (tBu)3PHBF4 (1.1 g, 3.8 mmol), and tBuONa (2.74 g, 28.53 mmol) were added to 95 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 90-3 (13.29 g, yield 92%). The molecular weight of Intermediate 90-3 was about 759 as measured by FAB MS.
A small amount of toluene (about 10 mL) was added to Intermediate 90-3 (14.95 g, 19.69 mmol), 4-iodo-1,1′-biphenyl (44.12 g, 157.5 mmol), CuI (3.94 g, 20.67 mmol), and K2CO3 (21.77 g, 157.5 mmol), and the resultant mixture was heated for about 24 hours while maintaining a temperature at about 215° C. The mixture was diluted with CH2Cl2, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 90-4 (10.95 g, yield 61%). The molecular weight of Intermediate 90-4 was about 912 as measured by FAB MS.
In an Ar atmosphere, Intermediate 90-4 (10.82 g, 11.87 mmol) was dissolved in ODCB (119 mL), BBr3 (5.95 g, 23.74 mmol) was added thereto, and the resultant mixture was heated and stirred at about 170° C. for about 10 hours. The resultant mixture was cooled to room temperature, DIPEA (18.37 g, 142.44 mmol) was added thereto, water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Intermediate 90-5 (4.36 g, yield 40%). The molecular weight of Intermediate 90-5 was about 919 as measured by FAB MS.
In an Ar atmosphere, Intermediate 90-5 (4.01 g, 4.89 mmol), 3,6-diphenyl-9H-carbazole (2.45 g, 14.66 mmol), Pd(dba)2 (0.28 g, 0.49 mmol), (tBu)3PHBF4 (0.28 g, 0.98 mmol), and tBuONa (1.88 g, 19.54 mmol) were added to 24 mL of toluene, and the resultant mixture was heated and stirred at about 100° C. for about 8 hours. Water was added thereto, and the resultant mixture was subjected to celite filtering and then liquid separation to concentrate an organic layer. The concentrated organic layer was purified by silica gel column chromatography to obtain Compound 90 (3.97 g, yield 75%). The molecular weight of Compound 90 was about 1082 as measured by FAB MS.
The purification by sublimation was performed (340° C., 2.6×10−3 Pa) to perform device evaluation.
The light emitting element of an example including the fused polycyclic compound of an example in an emission layer of the light emitting element was manufactured as follows. Fused polycyclic compounds of Compounds 4, 35, 37, 40, 44, 59, and 90, which are Example Compounds as described above, were utilized as a dopant material for an emission layer to manufacture the light emitting elements of Examples 1 to 7, respectively. Comparative Examples 1 to 10 correspond to the light emitting elements manufactured by utilizing respective Comparative Example Compounds X-1 to X-10 as emission layer dopant materials, respectively.
ITO was utilized to form a 150 nm-thick first electrode on a substrate, dipyrazino[2,3-f: 2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HATCN) was utilized to form a 10 nm-thick hole injection layer on the first electrode, N,N-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (NPD) was utilized to form a 80 nm-thick hole transport layer on the hole injection layer, 1,3-bis(N-carbazolyl)benzene (mCP) was utilized to form a 5 nm-thick emission auxiliary layer on the hole transport layer, Example Compound or Comparative Example Compound was doped by 1% by weight to 3,3′-di(9H-carbazol-9-yl)-1,1′-biphenyl (mCBP) to form a 20 nm-thick emission layer on the emission auxiliary layer, 2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi) was utilized to form a 30 nm-thick electron transport layer on the emission layer, LiF was utilized to form a 0.5 nm-thick electron injection layer on the electron transport layer, and Al was utilized to form a 300 nm-thick second electrode on the electron injection layer. Each layer was formed by a deposition method in a vacuum atmosphere.
Compounds utilized for manufacturing the light emitting elements of Examples and Comparative Examples are disclosed herein. The compounds are suitable materials, and commercial products were subjected to sublimation purification and utilized to manufacture the devices:
Evaluation results of each of the light emitting elements of Examples 1 to 7 and Comparative Examples 1 to 10 are listed in Table 1. A maximum emission wavelength (λmax), a delayed fluorescence service life (e.g., lifespan), roll-off, and a relative service life (LT50) in each of the manufactured light emitting elements are listed in comparison in Table 1.
In the characteristic evaluation results of Examples and Comparative Examples listed in Table 1, the roll-off is represented by [[(external quantum efficiency at 1 cd/m2)−(1,000 cd/m2)]/(external quantum efficiency at 1 cd/m2)]×100. In addition, the relative service life is shown by evaluating a brightness half-life from an initial brightness of 100 cd/m2. The relative service life is shown relatively on the basis of the result of Comparative Example 3.
Referring to the results of Table 1, it may be confirmed that Examples of the light emitting elements, in which the fused polycyclic compounds according to examples of the present disclosure are utilized as luminescent materials, each have improved service life characteristics as compared with Comparative Examples. Example Compounds include the fused ring core in which the first to third aromatic rings are fused about the boron atom, the first nitrogen atom, and the first heteroatom, and include a structure in which the first substituent, a steric hindrance substituent at the first nitrogen atom, and thus may effectively protect the boron atom, thereby achieving high efficiency and long service life. Example Compounds may have an increase in the luminous efficiency and may suppress or reduce the red shift of emission wavelength because the intermolecular interaction may be suppressed or reduced by the introduction of the first substituent, thereby controlling the formation of excimer or exciplex. In addition, Example Compounds each have 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.
Moreover, Example Compounds include the second substituent having electron donor properties linked to the fused ring core, and thus may have an increase in multiple resonance effects and have a low ΔEST. Accordingly, because reverse intersystem crossing (RISC) from the triplet excited state to the singlet excited state easily occurs, delayed fluorescence characteristics may be enhanced, thereby improving the luminous efficiency. In addition, Example Compounds have a structure in which the second substituent is substituted at the para-position with respect to the first heteroatom, so that a singlet energy level (S1) may be increased, thereby providing a deep blue emission color.
The light emitting element of one or more embodiments includes the fused polycyclic compound of one or more embodiments as a light emitting dopant of a thermally activated delayed fluorescence (TADF) light emitting element, and thus may achieve long service life.
It may be confirmed that the emission wavelengths of Examples 1 to 6 show color purity close to pure blue around 460 nm, and all exhibit long service life characteristics compared to Comparative Examples 1 to 10.
The fused polycyclic compounds of the present disclosure all have a structure that the first substituent, which is bulky, is substituted at the first nitrogen atom with respect to the fused ring core in which the first to third aromatic rings are fused about the boron atom, the first nitrogen atom, and the first heteroatom, and thus have an effect of spatially protecting the fused ring core due to the first substituent. In addition, like the part indicated by the arrow in Formula E1, the second substituent is introduced into the para-position with X atom corresponding to the first heteroatom, so that it may be easy to control the wavelength.
It may be confirmed that Examples 1 to 4 all show color purity close to pure blue around 460 nm.
Comparative Example 3 is a compound having rigidity in service life characteristics, and in the element evaluation, the relative service life of Comparative Example 3 was set as a baseline, 1. The relative service lives of Examples 1 to 4 are 1.8-fold to 2.8-fold, and exhibit an effect of improving service life compared to Comparative Example 3. It is thought that this service life improving effect is obtained by introducing the bulky first substituent into the first nitrogen atom in the fused ring core skeleton.
It may be seen that Examples 1 to 4 all have a much longer relative service life than Comparative Examples 1, 2, and 4 to 10 having one boron atom as the fused ring core-constituting atom, and the fused polycyclic compound of an embodiment of the present disclosure thus should have a relatively long service life effect.
In addition, when Example 1 is compared with Examples 2 to 4, Compound 4 of Example 1 corresponds to a compound having hydrogen as the substituent represented by Ry in the fused polycyclic compound represented by Formula 1. It may be confirmed that the relative service life of Example 1 is 1.8, which exhibits longer service life characteristics than Comparative Examples, but as the relative service lives of Examples 2 to 4 are 2.3 to 2.8, when the substituent Ry is 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 rather than hydrogen, the service life characteristics are further improved.
Examples 5 and 6 all show color purity close to pure blue around 460 nm. In addition, the relative service lives of Examples 5 and 6 are 3.3 and 2.9, which exhibit longer service lives than Comparative Examples.
Example 7 exhibits an emission wavelength of 463 nm and a relative service life of 2.8-fold, and the service life characteristics are improved compared to Comparative Examples. It is thought that this service life improving effect is obtained by introducing the first substituent into the fused ring core skeleton, and it may be confirmed that the relative service life is greatly increased compared to Comparative Examples 1, 2, and 7 having a structure similar to Example 7.
The light emitting element of one or more embodiments of the present disclosure may exhibit improved element characteristics with a relatively long service life.
The fused polycyclic compound of one or more embodiments may be included in an emission layer of a light emitting element to contribute to relatively long service life of the light emitting element.
As utilized herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The light-emitting element/device, the display device, the display apparatus, or any other relevant apparatuses/devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
Although the present disclosure has been described with reference to example embodiments of the present disclosure, it will be understood that the present disclosure should not be limited to these 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 present disclosure, but is intended to be defined by the appended claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0029486 | Mar 2023 | KR | national |
