Patent Application
20230054166
This application claims priority to Korean Patent Applications Nos. 10-2021-0076312, filed on Jun. 11, 2021, and 10-2022-0070184, filed on Jun. 9, 2022, both in the Korean Intellectual Property Office, and all benefits accruing therefrom under 35 U.S.C. § 119, the entire contents of which are incorporated by reference herein.
Provided are a composition, a layer including the composition, a light-emitting device including the composition, and an electronic apparatus including the light-emitting device.
From among light-emitting devices, organic light-emitting devices (OLEDs) are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, luminance, driving voltage, and response speed, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.
Provided are a composition capable of providing excellent luminescence efficiency and lifespan characteristics and the like, a layer including the composition, a light-emitting device including the composition, an electronic apparatus including the light-emitting device.
Additional aspects will be set forth in part in the description, which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments as described herein.
According to an aspect, provided is a composition including a first compound represented by Formula 1 and a second compound represented by Formula 2.
Ir(L11)n11(L12)n12(L13)n13 Formula 1
Ir(L21)n21(L22)n22(L23)n23 Formula 2
wherein, in Formulae 1 and 2,
L11, L12, L13, L21, L22, and L23 are each:
i) a bidentate ligand bonded to iridium (Ir) of Formula 1 via two nitrogen atoms, or a bidentate ligand bonded to iridium of Formula 2 via two nitrogen atoms,
ii) a bidentate ligand bonded to iridium of Formula 1 via a nitrogen atom and a carbon atom, or a bidentate ligand bonded to iridium of Formula 2 via a nitrogen atom and a carbon atom, or
iii) a bidentate ligand bonded to iridium of Formula 1 via two carbon atoms, or a bidentate ligand bonded to iridium of Formula 2 via two carbon atoms,
L11, L12, and L13 are different from one another,
n11 and n12 are each independently 1 or 2,
n13 is 0 or 1,
the sum of n11, n12, and n13 is 3,
L21, L22, and L23 are different from one another,
n21 and n22 are each independently 1 or 2,
n23 is 0 or 1,
the sum of n21, n22, and n23 is 3, and
L11 and L21 are different from each other.
According to another aspect, provided is a layer including the composition described herein.
According to another aspect, provided is a light-emitting device including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes the composition described herein.
In one or more embodiments, the emission layer of the light-emitting device may include the composition described herein.
According to another aspect, provided is an electronic apparatus including the light-emitting device described herein.
The above and other aspects, features, and advantages of certain embodiments will be more apparent from the following description taken in conjunction with the accompanying drawings, in which
The FIGURE shows a schematic cross-sectional view of a light-emitting device according to aspects of one or more embodiments.
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
A composition according to one or more embodiments includes a first compound represented by Formula 1 and a second compound represented by Formula 2:
Ir(L11)n11(L12)n12(L13)n13 Formula 1
Ir(L21)n21(L22)n22(L23)n23 Formula 2
wherein each of Formulae 1 and 2 includes one iridium (Ir).
Each of the first compound and the second compound may be electrically neutral.
In Formulae 1 and 2, L11, L12, L13, L21, L22, and L23 are each independently:
i) a bidentate ligand bonded to iridium (Ir) of Formula 1 via two nitrogen atoms, or a bidentate ligand bonded to iridium of Formula 2 via two nitrogen atoms,
ii) a bidentate ligand bonded to iridium of Formula 1 via a nitrogen atom and a carbon atom, or a bidentate ligand bonded to iridium of Formula 2 via a nitrogen atom and a carbon atom, or
iii) a bidentate ligand bonded to iridium of Formula 1 via two carbon atoms, or a bidentate ligand bonded to iridium of Formula 2 via two carbon atoms.
In one or more embodiments, in Formulae 1 and 2, L11, L12, L13, L21, L22, and L23 may each be a bidentate ligand bonded to iridium in Formula 1 or 2 via a nitrogen atom and a carbon atom.
L11, L12, and L13 in Formula 1 are different from one another.
In Formula 1, n11 and n12 are each independently 1 or 2, and n13 is 0 or 1. The sum of n11, n12, and n13 is 3.
In one or more embodiments, in Formula 1, i) n11 may be 1, n12 may be 2, and n13 may be 0; or ii) n11 may be 2, n12 may be 1, and n13 may be 0.
L21, L22, and L23 in Formula 2 are different from one another.
In Formula 2, n21 and n22 re each independently 1 or 2, and n23 is 0 or 1. The sum of n21, n22, and n23 is 3.
In one or more embodiments, in Formula 2, i) n21 may be 1, n22 may be 2, and n23 may be 0; or ii) n21 may be 2, n22 may be 1, and n23 may be 0.
Each of the first compound and the second compound may be a heteroleptic complex.
In one or more embodiments, n13 in Formula 1 may be 0, and n23 in Formula 2 may be 0.
In Formulae 1 and 2,
L11 may be a ligand represented by Formula 1-1,
L12 may be a ligand represented by Formula 1-2,
L13 may be a ligand represented by Formula 1-1 or a ligand represented by Formula 1-2,
L21 may be a ligand represented by Formula 2-1,
L22 may be a ligand represented by Formula 2-2, and
L23 may be a ligand represented by Formula 2-1 or a ligand represented by Formula 2-2:
wherein Y1 to Y8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be N or C.
In one or more embodiments, Y1, Y3, Y5, and Y7 may be N, and Y2, Y4, Y6, and Y8 may be C.
In one or more embodiments, i) Y1 and Y2 may each be C, ii) Y3 and Y4 may each be C, iii) Y5 and Y6 may each be C, or iv) Y7 and Y8 may each be C.
In Formulae 1, 2, 1-1, 1-2, 2-1, and 2-2, i) a bond between Y1 and iridium, a bond between Y3 and iridium, a bond between Y5 and iridium, and a bond between Y7 and iridium may each be a coordinate bond, and ii) a bond between Y2 and iridium, a bond between Y4 and iridium, a bond between Y6 and iridium, and a bond between Y8 and iridium may each be a covalent bond. Thus, each of the first compound and the second compound may be electrically neutral.
In Formulae 1-1, 1-2, 2-1, and 2-2, ring A1, ring A2, ring A3, ring A4, ring A5, ring A6, ring A7, and ring A8 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, i) ring A1, ring A3, ring A5, and ring A7 may each be a C1-C30 heterocyclic group, and ii) ring A2, ring A4, ring A6, and ring A8 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, i) ring A1, ring A3, ring A5, and ring A7 may each be a C1-C30 heterocyclic group, ii) ring A2, ring A4, ring A6, and ring A8 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, iii) Y1, Y3, Y5, and Y7 may each be N, and iv) Y2, Y4, Y6, and Y8 may each be C.
In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A1, ring A3, ring A5, and ring A7 may each independently be i) ring T1, ii) a condensed ring in which two or more ring T1 are condensed with each other, or iii) a condensed ring in which at least one ring T1 and at least one ring T2 are condensed with each other,
ring T1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
ring T2 may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, or a benzene group.
In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A2, ring A4, ring A6, and ring A8 may each be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other, the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A1, ring A3, ring A5, and ring A7 may each independently be an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidino pyrrole group, a pyrimidino pyrazole group, a pyrimidino imidazole group, a pyrimidino oxazole group, a pyrimidino isoxazole group, a pyrimidino thiazole group, a pyrimidino isothiazole group, a pyrimidino oxadiazole group, a pyrimidinothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthooxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthooxadiazole group, a naphthothiadiazole group, a phenanthrenopyrrole group, a phenanthrenopyrazole group, a phenanthrenoimidazole group, a phenanthrenooxazole group, a phenanthrenoisoxazole group, a phenanthrenothiazole group, a phenanthrenoisothiazole group, a phenanthrenooxadiazole group, a phenanthrenothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.
In one or more embodiments, in Formulae 1-1, 1-2, 2-1, and 2-2, ring A2, ring A4, ring A6, and ring A8 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidinopyrrole group, a pyrimidinopyrazole group, a pyrimidinoimidazole group, a pyrimidinooxazole group, a pyrimidinoisoxazole group, a pyrimidinothiazole group, a pyrimidinoisothiazole group, a pyrimidinooxadiazole group, a pyrimidinothiadiazole group, a naphthopyrrole group, a naphthopyrazole group, a naphthoimidazole group, a naphthooxazole group, a naphthoisoxazole group, a naphthothiazole group, a naphthoisothiazole group, a naphthooxadiazole group, a naphthothiadiazole group, a phenanthrenopyrrole group, a phenanthrenopyrazole group, a phenanthrenoimidazole group, a phenanthrenooxazole group, a phenanthrenoisoxazole group, a phenanthrenothiazole group, a phenanthrenoisothiazole group, a phenanthrenooxadiazole group, a phenanthrenothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, a benzene group condensed with a norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.
Ring A1 and ring A3 in Formulae 1-1 and 1-2 may be different from each other.
In one or more embodiments, a Y1-containing monocyclic group in ring A1, a Y2-containing monocyclic group in ring A2, and a Y4-containing monocyclic group in ring A4 may each be a 6-membered ring. In other words, ring A1, ring A2, and ring A4 may each comprise a 6-membered ring. For example, ring A1 and ring A2 may each be a 6-membered ring, and ring A4 may comprise a 6-membered ring.
In one or more embodiments, a Y3-containing monocyclic group in ring A3 may be a 6-membered ring. In other words, ring A3 may comprise a 6-membered ring.
In one or more embodiments, a Y3-containing monocyclic group in ring A3 may be a 5-membered ring. In other words, ring A3 may comprise a 5-membered ring.
In one or more embodiments, a Y1-containing monocyclic group in ring A1 may be a 6-membered ring, and a Y3-containing monocyclic group in ring A3 may be a 5-membered ring. In other words, ring A1 may comprise a 6-membered ring and ring A3 may comprise a 5-membered ring. For example, ring A1 may be a 6-membered ring and ring A3 may comprise a 5-membered ring.
Ring A5 and ring A7 in Formulae 2-1 and 2-2 may be identical to each other.
In one or more embodiments, a Y5-containing monocyclic group in ring A5, a Y6-containing monocyclic group in ring A6, and a Y8-containing monocyclic group in ring A8 may each be a 6-membered ring. In other words, ring A5, ring A6, and ring A8 may each comprise a 6-membered ring. For example, ring A5 and ring A6 may each be a 6-membered ring, and ring A8 may comprise a 6-membered ring.
In one or more embodiments, a Y7-containing monocyclic group in ring A7 may be a 6-membered ring. In other words, ring A7 may comprise a 6-membered ring. For example, ring A7 may be a 6-membered ring.
In one or more embodiments, a Y7-containing monocyclic group in ring A7 may be a 5-membered ring. In other words, ring A7 may comprise a 5-membered ring. For example, ring A7 may be a 5-membered ring.
In one or more embodiments, a Y5-containing monocyclic group in ring A5 and a Y7-containing monocyclic group in ring A7 may each be a 6-membered ring.
In one or more embodiments, ring A1, ring A3, ring A5, and ring A7 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be i) an A group, ii) a polycyclic group in which two or more A groups are condensed with each other, or iii) a polycyclic group in which at least one A group and at least one B group are condensed with each other,
the A group may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
the B group may be a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, or a silole group.
In one or more embodiments, in Formulae 1-2 and 2-2, ring A3 and ring A7 may each independently be i) a C group, ii) a polycyclic group in which two or more C groups are condensed with each other, or iii) a polycyclic group in which at least one C group and at least one D group are condensed with each other,
the C group may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, or an isothiazole group, and
the D group may be a cyclohexane group, a cyclohexene group, a norbornane group, a benzene group, a furan group, a thiophene group, a selenophene group, a cyclopentadiene group, a silole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group.
In one or more embodiments, ring A1 and ring A5 in Formulae 1-1 and 2-1 may each independently be:
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group; or
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.
In one or more embodiments, ring A3 and ring A7 in Formulae 1-2 and 2-2 may each independently be:
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group;
a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof; or
an imidazole group, a benzimidazole group, a naphthoimidazole group, a phenanthrenoimidazole group, a pyridinooimidazole group, an oxazole group, a benzoxazole group, a naphthooxazole group, a phenanthrenooxazole group, a pyridinoooxazole group, a thiazole group, a benzothiazole group, a naphthothiazole group, a phenanthrenothiazole group, or a pyridinoothiazole group.
In one or more embodiments, ring A2 and ring A4 in Formulae 1-1 and 1-2 may be different from each other.
In one or more embodiments, ring A6 and ring A8 in Formulae 2-1 and 2-2 may be different from each other.
In one or more embodiments, ring A2, ring A4, ring A6, and ring A8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be i) an E group, ii) a polycyclic group in which two or more E groups are condensed with each other, or iii) a polycyclic group in which at least one E group and at least one F group are condensed with each other,
the E group may be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
the F group may be a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, or an isothiazole group.
In one or more embodiments, ring A2 in Formula 1-1 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.
In one or more embodiments, ring A4 in Formula 1-2 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.
In one or more embodiments, ring A6 in Formula 2-1 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.
In one or more embodiments, ring A8 in Formula 2-2 may be a polycyclic group in which two or more E groups and at least one F group are condensed with each other.
In one or more embodiments, ring A2 and ring A6 in Formulae 1-1 and 2-1 may each independently be:
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group, each condensed with at least one of a cyclohexane group, a norbornane group, a benzene group, or a combination thereof.
In one or more embodiments, ring A4 and ring A8 in Formulae 1-2 and 2-2 may each independently be:
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group or a phenanthrobenzofuran group; or
a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group, each condensed with at least one of a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a cyclohexane group, a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, a silole group, a pyrazole group, an imidazole group, an oxazole group, a thiazole group, an isoxazole group, an isothiazole group, or a combination thereof.
W1 to W8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be a single bond, a C1-C20 alkylene group that is unsubstituted or substituted with at least one R10a, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
For example, W1 to W8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:
a single bond; or
a C1-C20 alkylene group, a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, W1 to W8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:
a single bond; or
a benzene group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, W1 to W8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:
a single bond; or
a C1-C20 alkylene group, a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.
Z1 to Z8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q), or —P(Q8)(Q). Q1 to Q9 are respectively as described herein.
In one or more embodiments, Z1 to Z8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 may each independently be:
deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, —CD2CDH2, —CF3, —CF2H, —CFH2, —CH2CF3, —CH2CF2H, —CH2CFH2, —CHFCH3, —CHFCF2H, —CHFCFH2, —CHFCF3, —CF2CF3, —CF2CF2H, or —CF2CFH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, —F, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, Z1 to Z8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 a heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated C1-C20 alkoxy group, a fluorinated C1-C20 alkoxy group, a C1-C20 alkylthio group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in Formula 1-1,
e1 and d1 may each not be 0, and
one or more Z1(s) may each independently be:
a C1-C20 alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;
—Si(Q3)(Q4)(Q5); or
—Ge(Q3)(Q4)(Q5).
Q3 to Q5 are respectively as described herein.
In one or more embodiments, in Formula 2-1,
e5 and d5 may each not be 0, and
one or more Z5(s) may each independently be:
a C1-C20 alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;
—Si(Q3)(Q4)(Q5); or
—Ge(Q3)(Q4)(Q5).
Q3 to Q5 are respectively as described herein.
In one or more embodiments, Q3 to Q5 may each independently be:
a C1-C60 alkyl group unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; or
a C6-C60 aryl group unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof.
In one or more embodiments, Q3 to Q5 may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, Q3 to Q5 may be identical to each other (i.e., the same).
In one or more embodiments, two or more of Q3 to Q5 may be different from each other.
In one or more embodiments, Z1 to Z8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be: hydrogen, deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C1-C10 alkenyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-227, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-129, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 are respectively as described herein:
In Formulae 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:
wherein * indicates a binding site to a neighboring atom
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:
wherein * indicates a binding site to a neighboring atom
The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
wherein * indicates a binding site to a neighboring atom
The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-617:
wherein * indicates a binding site to a neighboring atom.
e1 to e8 and d1 to d8 in Formulae 1-1, 1-2, 2-1, and 2-2 indicates numbers of Z1 to Z8 group(s), a group represented by *—[W1—(Z1)e1], a group represented by *—[W2—(Z2)e2], a group represented by *—[W3—(Z3)e3], a group represented by *—[W4—(Z4)e4], a group represented by *—[W5—(Z5)e5], a group represented by *—[W6—(Z6)e6], a group represented by *—[W7—(Z7)e7], and a group represented by *—[W8—(Z8)e8], respectively, and may each independently be an integer from 0 to 20. When e1 is 2 or more, two or more of Z1(s) may be identical to or different from each other, when e2 is 2 or more, two or more of Z2(s) may be identical to or different from each other, when e3 is 2 or more, two or more of Z3(s) may be identical to or different from each other, when e4 is 2 or more, two or more of Z4(s) may be identical to or different from each other, when e5 is 2 or more, two or more of Z5(s) may be identical to or different from each other, when e6 is 2 or more, two or more of Z6(s) may be identical to or different from each other, when e7 is 2 or more, two or more of Z7(s) may be identical to or different from each other, when e8 is 2 or more, two or more of Z8(s) may be identical to or different from each other, when d1 is 2 or more, two or more of groups represented by *—[W1—(Z1)e1] may be identical to or different from each other, when d2 is 2 or more, two or more of groups represented by *—[W2—(Z2)e2] may be identical to or different from each other, when d3 is 2 or more, two or more of groups represented by *—[W3—(Z3)e3] may be identical to or different from each other, when d4 is 2 or more, two or more of groups represented by *—[W4—(Z4)e1] may be identical to or different from each other, when d5 is 2 or more, two or more of groups represented by *—[W5—(Z5)e5] may be identical to or different from each other, when d6 is 2 or more, two or more of groups represented by *—[W6—(Z6)e6] may be identical to or different from each other, when d7 is 2 or more, two or more of groups represented by *—[W7—(Z7)e7] may be identical to or different from each other, and when d8 is 2 or more, two or more of groups represented by *—[W8—(Z8)e8] may be identical to or different from each other. In one or more embodiments, e1 to e8 and d1 to d8 in Formulae 1-1, 1-2, 2-1, and 2-2 may each independently be 0, 1, 2, or 3.
* and *′ herein each indicate a binding site to a neighboring atom, unless otherwise stated.
In Formulae 1-1, 1-2, 2-1, and 2-2, one or more of i) two or more of a plurality of Z1(s), ii) two or more of a plurality of Z2(s), iii) two or more of a plurality of Z3(s), iv) two or more of a plurality of Z4(s), v) two or more of a plurality of Z5(s), vi) two or more of a plurality of Z6(s), vii) two or more of a plurality of Z7(s), and viii) two or more of a plurality of Z8(s) may respectively optionally be bonded to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
R10a may be as described in connection with Z1 herein.
* and *′ in Formulae 1-1, 1-2, 2-1, and 2-2 each indicate a binding site to iridium in Formulae 1 and 2.
In one or more embodiments, a group represented by
in Formula 1-1 may be a group represented by one of Formulae A1-1 to A1-3.
In one or more embodiments, a group represented by
in Formula 2-1 may be a group represented by one of Formulae A5-1 to A5-3:
In Formulae A1-1 to A1-3 and A5-1 to A5-3,
Z11 to Z14 are respectively as described in connection with Z1 herein,
Z51 to Z54 are respectively as described in connection with Z5 herein,
R10a is as described herein,
a14 may be an integer from 0 to 4,
a18 may be an integer from 0 to 8,
*′ indicates a binding site to iridium in Formulae 1 and 2, and
*″ indicates a binding site to ring A2 or ring A6.
In one or more embodiments, at least one of Z11, Z12, and Z14 (for example, Z14) in Formulae A1-1 to A1-3 and at least one of Z51, Z52, and Z54 (for example, Z54) in Formulae A5-1 to A5-3 may each independently be:
a C1-C20 alkyl group that is unsubstituted or substituted with at least one of deuterium, —F, a phenyl group, or a combination thereof;
—Si(Q3)(Q4)(Q5); or
—Ge(Q3)(Q4)(Q5).
In one or more embodiments,
Y3 in Formula 1-2 and Y7 in Formula 2-2 may each be N, and
a group represented by
a group represented by
in Formula 2-2 may each independently be a group represented by one of Formulae NR1 to NR48:
wherein, in Formulae NR1 to NR48,
Y39 may be O, S, Se, N—[W3—(Z3)e3], N—[W7—(Z7)e7], C(Z39a)(Z39b), C(Z79a)(Z79b), Si(Z39a)(Z39b), or Si(Z79a)(Z79b),
W3, W7, Z3, Z7, e3, and e7 are respectively as described herein, Z39a and Z39b are respectively as described in connection with Z3 herein, and Z79a and Z79b are each as described in connection with Z7 herein,
*′ indicates a binding site to iridium in Formula 1 or 2, and
*″ indicates a binding site to ring A4 or ring A8.
In one or more embodiments, a group represented by
in Formula 1-2 may be a group represented by one of Formulae NR30 to NR48.
In one or more embodiments,
Y2 in Formula 1-1, Y4 in Formula 1-2, Y6 in Formula 2-1, and Y8 in Formula 2-2 may each be C, and
a group represented by
a group represented by
a group represented by
a group represented by
in Formula 2-2 may each independently be a group represented by one of Formulae CR1 to CR29:
wherein, in Formulae CR1 to CR29,
Y49 may be O, S, Se, N—[W2—(Z2)e2], N—[W4—(Z4)e4], N—[W6—(Z6)e6], N—[W8—(Z8)e8], C(Z29a)(Z29b), C(Z49a)(Z49b), C(Z69a)(Z69b), C(Z89a)(Z89b), Si(Z29a)(Z29b), Si(Z49a)(Z49b), Si(Z69a)(Z69b), or Si(Z89a)(Z89b),
W2, W4, W6, W8, Z2, Z4, Z6, Z8, e2, e4, e6, and e8 are respectively as described herein, Z29a and Z29b are respectively as described in connection with Z2 herein, Z49a and Z49b are respectively as described in connection with Z4 herein, Z69a and Z69b are respectively as described in connection with Z6 herein, and Z89a and Z89b are respectively as described in connection with Z8 herein,
Y21 to Y24 may each independently be N or C,
ring A40 may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group (for example, a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, or benzoquinazoline group),
* indicates a binding site to iridium in Formulae 1 and 2, and
*″ indicates a binding site to ring A1, ring A3, ring A5, and ring A7.
In one or more embodiments, a group represented by
in Formulae CR24 to CR29 may be a group represented by one of Formulae CR(1) to CR(13):
wherein, in Formulae CR(1) to CR(13),
Y49 is as described herein, and
Y31 to Y34 and Y41 to Y48 may each independently be C or N.
In one or more embodiments, the first compound may include at least one deuterium.
In one or more embodiments, the second compound may include at least one deuterium.
The first compound may emit a first light including a first spectrum, and λP(1) may be an emission peak wavelength (in nanometers, nm) of the first spectrum.
The second compound may emit a second light including a second spectrum, and λP(2) may be an emission peak wavelength (nm) of the second spectrum.
The λP(1) and the λP(2) may be evaluated from a photoluminescence (PL) spectra measured for a first film and a second film, respectively.
As used herein, the “first film” is a film including the first compound, and the “second film” is a film including the second compound. The first film and the second film may be manufactured using various methods such as any method, for example, a vacuum deposition method, a coating and heating method. The first film and the second film may further include other compounds, for example, a host described herein, in addition to the first compound and the second compound.
In one or more embodiments, each of the λP(1) and the λP(2) may be about 480 nm to about 580 nm, or about 510 nm to about 570 nm.
In one or more embodiments, an absolute value of a difference between the λP(1) and the λP(2) may be about 0 nm to about 30 nm, about 0 nm to about 20 nm, or about 0 nm to about 10 nm.
In one or more embodiments, the first light and the second light may each be green light.
In one or more embodiments, the first light may be green light, and the second light may be yellow-green light.
In one or more embodiments, the first light and the second light may each be yellow-green light.
In one or more embodiments, the first light may be yellow-green light, and the second light may be yellow light.
In one or more embodiments, the first light and the second light may each be yellow light.
In one or more embodiments, L11 and L13 in Formula 1, L21 and L23 in Formula 2, a ligand represented by Formula 1-1, and a ligand represented by Formula 2-1 may each independently be represented by one of Formulae A1 to A380:
In one or more embodiments, L12 and L13 in Formula 1, L22 and L23 in Formula 2, a ligand represented by Formula 1-2, and a ligand represented by Formula 2-2 may each independently be represented by one of B1 to B1542:
wherein * and *′ each indicate a binding site to iridium.
In one or more embodiments, L12 and L13 in Formula 1 and a ligand represented by Formula 1-2 may each independently be selected from B to B780.
In one or more embodiments, L22 and L23 in Formula 2 and a ligand represented by Formula 2-2 may each independently be selected from B781 to B1542.
In one or more embodiments, the first compound and the second compound may each be one of compounds described in Tables 1 to 11 below.
Among the compounds in Tables 1 to 11, a compound of Group 1 is represented by Ir(L1)2(L2), and L1 and L2 among compounds represented by Ir(L1)2(L2) of Group 1 are as described in Tables 1 to 11.
Among the compounds in Tables 1 to 11, a compound of Group 2 is represented by Ir(L1)(L2)2, and L1 and L2 among compounds represented by Ir(L1)(L2)2 of Group 2 are as described in Tables 1 to 11.
x in Tables 1 to 11 is an integer from 1 to 380. Ax, i.e., A1 to A380, is as described above.
For example, in Tables 1 to 11,
1) Compound 93-10 (i.e., x=93) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A93 and L2 is B10, and may be represented by Compound 1 below,
2) Compound 298-58 (i.e., x=298) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A298 and L2 is B58, and may be represented by Compound 2 below,
3) Compound 260-373 (i.e., x=260) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A260 and L2 is B373, and may be represented by Compound 3 below,
4) Compound 198-1465 (i.e., x=198) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A198 and L2 is B1465, and may be represented by Compound 4,
5) Compound 1-1541 (i.e., x=1) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A1 and L2 is B1541, and may be represented Compound 5,
6) Compound 260-1542 (i.e., x=260) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A260 and L2 is B1542, and may be represented by Compound 6,
7) Compound 201-1070 (i.e., x=201) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A201 and L2 is B1070, and may be represented by Compound 7,
8) Compound 202-721 (i.e., x=202) of Group 1 is a compound represented by Ir(L1)2(L2) in which L1 is A202 and L2 is B721, and may be represented by Compound 8, and
9) Compound 93-10 (i.e., x=93) of Group 2 is a compound represented by Ir(L1)(L2)2 in which L1 is A93 and L2 is B10, and may be represented by Compound 9:
The remaining compounds in Tables 1 to 11 may also be recognized in the same manner as described above.
A composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described above may emit light (for example, light having an emission peak wavelength in a range of about 480 nm to about 580 nm, or about 510 nm to about 570 nm, such as green light, yellow-green light, or yellow light) having excellent luminescence efficiency and excellent lifespan. Thus, a layer including the composition, a light-emitting device including the composition, and an electronic apparatus including the light-emitting device may be provided.
According to another aspect, a layer including the composition including the first compound and the second compound as described above may be provided.
In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 480 nm to about 580 nm, for example, about 510 nm to about 570 nm.
In one or more embodiments, the layer may emit green light, yellow-green light, or yellow light.
In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 510 nm to about 540 nm.
In one or more embodiments, the layer may emit light having an emission peak wavelength in a range of about 540 nm to about 570 nm.
A weight ratio of the first compound to the second compound included in the layer may be about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60.
In one or more embodiments, a weight ratio of the first compound to second compound may be about 50:50, that is, about 1:1.
The layer may be formed i) by a co-deposition of the first compound and the second compound, or ii) by using a first mixture including the first compound and the second compound.
In one or more embodiments, the layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition including the first compound and the second compound. The layer may be formed i) by a co-deposition of the host and the dopant, or ii) by using a second mixture including the host and the dopant.
A weight of the host in the layer may be greater than a weight of the dopant.
In one or more embodiments, a weight ratio of the host to the dopant in the layer may be about 99:1 to about 55:45, or about 97:3 to about 60:40, or about 95:5 to about 70:30.
The host in the layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.
According to another aspect, provided is a light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition including the first compound and the second compound as described above.
The light-emitting device includes the composition including the first compound and the second compound as described above, and thus, may have excellent driving voltage, excellent external quantum efficiency, and excellent lifespan characteristics. Also, the light-emitting device may have an excellent side luminance ratio.
In one or more embodiments, the emission layer in the organic layer of the light-emitting device may include the composition including the first compound and the second compound.
In one or more embodiments, the emission layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition.
The host in the emission layer may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof.
In one or more embodiments, the host may include a hole transport compound and an electron transport compound, and the hole transport compound and the electron transport compound may be different from each other.
The emission layer may be formed by a co-deposition of the host and the dopant, or may be formed by using a second mixture including the host and the dopant.
The emission layer may emit third light having a third spectrum, and λP(EML) is an emission peak wavelength (in nm) of the third spectrum. In one or more embodiments, the λP(EML) may be evaluated from electroluminescence spectrum of the light-emitting device.
Fourth light having a fourth spectrum may be extracted to the outside of the light-emitting device (i.e., the organic light-emitting device) through the first electrode and/or the second electrode of the light-emitting device, and λP(OLED) is an emission peak wavelength (nm) of the fourth spectrum. In one or more embodiments, the λP(OLED) may be evaluated from electroluminescence spectrum of the light-emitting device.
In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 480 nm to about 580 nm, for example, about 510 nm to about 570 nm.
In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 510 nm to about 540 nm.
In one or more embodiments, the λP(EML) and the λP(OLED) may each independently be about 540 nm to about 570 nm.
In one or more embodiments, the third light and the fourth light may each be green light, yellow-green light, or yellow light.
In one or more embodiments, the third light and the fourth light may not be white light.
In one or more embodiments, the third spectrum may include i) a main emission peak having the λP(EML), and may not include ii) an additional emission peak having an emission peak wavelength of (λP(EML)+about 50 nm) or greater or (λP(EML)−about 50 nm) or less.
In one or more embodiments, the third spectrum may include i) a main emission peak having the λP(EML), and may not include ii) an additional emission peak having an emission peak wavelength of red light and/or blue light region.
In one or more embodiments, the fourth spectrum may include i) a main emission peak having the λP(OLED), and may not include ii) an additional emission peak having an emission peak wavelength of (λP(OLED)+about 50 nm) or greater or (λP(OLED)−about 50 nm) or less.
In one or more embodiments, the fourth spectrum may include i) a main emission peak having the λP(OLED), and may not include ii) an additional emission peak having an emission peak wavelength of red light and/or blue light region.
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
In one or more embodiments, in the light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, the organic layer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode of the light-emitting device.
The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
The FIGURE is a schematic cross-sectional view of a light-emitting device 10 according to one or more embodiments described herein. Hereinafter, the structure and manufacturing method of the light-emitting device 10 according to one or more embodiments will be described with reference to FIGURE. The light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.
A substrate may be additionally located under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in light-emitting devices of the related art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
The organic layer 15 is located on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, each layer is sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (L-B) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec.
When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C.
The conditions for forming the hole transport layer and the electron blocking layer may be similar to or the same as the conditions for forming the hole injection layer.
The hole transport region may include 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB), 3-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or a combination thereof:
In Formula 201, Ar101 and Ar102 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C10 alkylthio group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.
R101 to R108, R111 to R119 and R121 to R124 in Formulae 201 and 202 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group), a C1-C10 alkoxy group(for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group), or a C1-C10 alkylthio group;
a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 alkylthio group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, or a combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, or a combination thereof.
In Formula 201, R109 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.
In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A:
wherein R101, R111, R112, and R109 in Formula 201A are respectively as described above.
In one or more embodiments, the hole transport region may include one of Compounds HT1 to HT20 or a combination thereof:
A thickness of the hole transport region may be in the range of about 100 angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-type dopant. The p-type dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or a combination thereof. For example, the p-type dopant may be: a quinone derivative such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; metal oxide, such as tungsten oxide and molybdenum oxide; a cyano group-containing compound, such as Compound HT-D1; or a combination thereof.
The hole transport region may further include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, luminescence efficiency of a light-emitting device may be improved.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include a material that is used in the hole transport region as described above, a host material described below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP, Compound H-H1, or a combination thereof may be used as the material for forming the electron blocking layer.
Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, L-B deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a material that is used to form the emission layer.
The emission layer may include the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein. In one or more embodiments, the emission layer may include a layer including the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein.
In one or more embodiments, the emission layer may include a host and a dopant, the host may not include a transition metal, and the dopant may include the composition including the first compound represented by Formula 1 and the second compound represented by Formula 2 as described herein.
The host may include 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN, also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-H2, or a combination thereof:
When the light-emitting device is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
An electron transport region may be located on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (Balq), or a combination thereof:
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include BCP, Bphen, TPBi, tris(8-hydroxyquinolinato)aluminum (Alq3), Balq, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or a combination thereof:
In one or more embodiments, the electron transport layer may include one or more of Compounds ET1 to ET25, or a combination thereof:
A thickness of the electron transport layer may be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.
The electron transport layer may include a metal-containing material in addition to the material as described above.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 or ET-D2:
Also, the electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, Compound ET-D1, Compound ET-D2, or a combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
In one or more embodiments, the composition, a layer including the composition, and an emission layer in a light-emitting device including the composition may not include a compound of [Group A] and mCP (1,3-bis(N-carbazolyl)benzene):
Hereinbefore, the light-emitting device has been described in connection with FIGURE, but embodiments are not limited thereto.
According to another aspect, the light-emitting device may be included in an electronic apparatus. Thus, an electronic apparatus including the light-emitting device is provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, or the like.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group, as used here refers to a divalent group having the same structure as the C1-C60 alkyl group.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof. For example, Formula 9-33 is a branched C6 alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like.
The term “C1-C60 alkylthio group” as used herein refers to a monovalent group having the formula of —SA101 (where A101 is the C1-C60 alkyl group).
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, a butenyl group, or the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, a propynyl group, or the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and the C3-C10 cycloalkylene group is a divalent group having the same structure as the C3-C10 cycloalkyl group.
Examples of the C3-C10 cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, or the like.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated cyclic group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms, and the term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group may include a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, or the like.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, or the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group. The term “C7-C60 aryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C6-C60 aryl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the two or more rings may be fused to each other.
The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group. The term “C2-C60 heteroaryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C1-C60 heteroaryl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 indicates the C6-C60 aryl group), the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 indicates the C6-C60 aryl group), and the term “C1-C60 alkylthio group” as used herein indicates —SA104 (wherein A104 indicates the C1-C60 alkyl group). The term “C1-C60 heteroaryloxy group” as used herein indicates —OA102′ (wherein A102′ indicates the C1-C60 heteroaryl group), and the term “C1-C60 heteroarylthio group” as used herein indicates —SA103′ (wherein A103′ indicates the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, including at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a)” used herein are an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, or a fluorene group (each unsubstituted or substituted with at least one R10a).
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. The “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a)” may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R10a).
In one or more embodiments, examples of the “C5-C30 carbocyclic group” and “C1-C30 heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,
the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
The terms “fluorinated C1-C60 alkyl group (or a fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group,” and “fluorinated phenyl group” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group (that is, a fluorinated methyl group)” includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or, a fluorinated C1-C20 alkyl group, or the like)”, “the fluorinated C3-C10 cycloalkyl group”, “the fluorinated C1-C10 heterocycloalkyl group”, or “the fluorinated phenyl group” may be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen included therein is not substituted with a fluoro group.
The terms “deuterated C1-C60 alkyl group (or a deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group (that is, the deuterated methyl group)” may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C1-C60 alkyl group (or, the deuterated C1-C20 alkyl group or the like)”, “the deuterated C3-C10 cycloalkyl group”, “the deuterated C1-C10 heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein is substituted with at least one of deuterium, or ii) a partially deuterated C1-C60 alkyl group (or, a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein is not substituted with deuterium.
The term “(C1-C20 alkyl) ‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group.
The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” as used herein respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group,” in which, in each group, at least one carbon selected from ring-forming carbons is substituted with nitrogen.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
a C1-C6 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof.
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 herein may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 described herein may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
Hereinafter, a compound and a light-emitting device according to one or more example embodiments are described in further detail with reference to Synthesis Example and Examples. However, the light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.
2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine (4.52 grams (g), 18.5 millimoles (mmol)) and iridium chloride hydrate (IrCl3.(H2O)n, n=3) (2.96 g, 8.40 mmol) were mixed with 30 milliliters (mL) of 2-ethoxyethanol and 10 mL of deionized (DI) water and then stirred while heating at reflux for 24 hours, and then, the temperature was allowed to cool to room temperature. The resulting solid was separated by filtration, washed sufficiently with water, methanol, and hexanes, in this stated order, and then dried in a vacuum oven to obtain 5.22 g (yield of 87%) of Compound 1A.
Compound 1 Å (2.4 g, 1.68 mmol) and 60 mL of methylene chloride (MC) were mixed together, and then, silver trifluoromethanesulfonate (silver triflate, AgOTf) (0.86 g, 3.36 mmol) were mixed with 20 mL of methanol (MeOH) and then added thereto. Afterwards, the mixture was stirred for 18 hours at room temperature while light was blocked from the reaction contents with aluminum foil, and then the resulting product was filtered through diatomaceous earth to remove the resulting solid, and the filtrate was subjected to reduced pressure to obtain a resulting product (Compound 1 B). Compound 1 B was used in the next reaction without an additional purification process.
Compound 1B (2.66 g, 2.98 mmol) and Compound 1C (1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(7-phenyldibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole) (1.78 g, 2.98 mmol) were mixed with 30 mL of 2-ethoxyethanol and 30 mL of N,N-dimethylformamide and then stirred while heating at reflux for 48 hours, and then the temperature was allowed to cool to room temperature. The obtained mixture was subjected to a reduced pressure to obtain a solid, on which column chromatography (eluent: ethyl acetate (EA) and hexanes) was performed to obtain 1.13 g (yield of 30%) of Compound 1. The obtained compound was identified by high resolution mass spectrometry (HRMS) with matrix assisted laser desorption ionization (MALDI) and by high performance liquid chromatography (HPLC) analysis.
HRMS (MALDI) calcd for C73H65D6IrN4OSi2: m/z 1274.5172 Found: 1274.5171.
6.3 g (yield of 90%) of Compound 2A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 2A(1) (2-(4-methyl-d3)phenyl-4-(propan-2-yl-2-d)-5-(trimethylgermyl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.
Compound 2B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 2A was used instead of Compound 1A. The obtained Compound 2B was used in the next reaction without an additional purification process.
1.61 g (yield of 40%) of Compound 2 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 2B was used instead of Compound 1 B and Compound 2C (1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(7-fluorodibenzo[b,d]furan-4-yl)-1H-naphtho[1,2-d]imidazole) was used instead of Compound 1C.
HRMS (MALDI) calcd for C77H72D8FIrN4OGe2: m/z 1444.4871 Found: 1444.4870.
6.13 g (yield of 88%) of Compound 3A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 3A(1) (2-phenyl-4-(propan-2-yl-2-d)-5-(trimethylgermyl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.
Compound 3B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 3A was used instead of Compound 1A. The obtained Compound 3B was used in the next reaction without an additional purification process.
1.32 g (yield of 36%) of Compound 3 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 3B was used instead of Compound 1B and Compound 3C (8-(1-(2,6-diisopropylphenyl)-1H-benzo[d]imidazol-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) was used instead of Compound 1C.
HRMS (MALDI) calcd for C65H67D5Ge2IrN5O: m/z 1284.4104 Found: 1281.4106.
4.31 g (yield of 81%) of Compound 4A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 4A(1) (4,5-bis(methyl-d3)-2-(6-(methyl-d3)-[1,1′-biphenyl]-3-yl)pyridine) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.
Compound 4B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 4A was used instead of Compound 1A. The obtained Compound 4B was used in the next reaction without an additional purification process.
1.44 g (yield of 38%) of Compound 4 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 4B was used instead of Compound 1B and Compound 4C (8-(4-(2,2-dimethylpropyl-1,1-d2)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) was used instead of Compound 1C.
HRMS (MALDI) calcd for C62H34D23IrN4O: m/z 1089.5605 Found: 1089.5606.
0.98 g (yield of 36%) of Compound 5 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 5B was used instead of Compound 1 B and Compound 5C was used instead of Compound 1C.
HRMS (MALDI) calcd for C46H56IrN3Si3: m/z 927.3411 Found: 927.3412.
1.12 g (yield of 32%) of Compound 6 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 3B was used instead of Compound 1 B and Compound 6C was used instead of Compound 1C.
HRMS (MALDI) calcd for C60H62D2Ge2IrN3O: m/z 1185.3228 Found: 1185.3226.
4.53 g (yield of 91%) of Compound 7A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that 2-phenyl-5-(trimethylgermyl)pyridine was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.
Compound 7B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 7A was used instead of Compound 1A. The obtained Compound 7B was used in the next reaction without an additional purification process.
1.25 g (yield of 37%) of Compound 7 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 7B was used instead of Compound 1 B and Compound 7C was used instead of Compound 1C.
HRMS (MALDI) calcd for C5H54D2Ge2IrN3O: m/z 1153.2602 Found: 1153.2600.
4.32 g (yield of 86%) of Compound 8A was obtained in a similar manner as used to obtain Compound 1A of Synthesis Example 1, except that Compound 8A(1) was used instead of 2-(4-(methyl-d3)phenyl)-5-(trimethylsilyl)pyridine.
Compound 8B was obtained in a similar manner as used to obtain Compound 1 B of Synthesis Example 1, except that Compound 8A was used instead of Compound 1A.
The obtained Compound 8B was used in the next reaction without an additional purification process.
1.49 g (yield of 36%) of Compound 8 was obtained in a similar manner as used to obtain Compound 1 of Synthesis Example 1, except that Compound 8B was used instead of Compound 1 B and Compound 8C was used instead of Compound 1C.
HRMS (MALDI) calcd for C75H79Ge2IrN4O: m/z 1392.4307 Found: 1392.4305.
As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water, each for 5 minutes, and then cleaned by irradiation of ultraviolet light and exposure of ozone for 30 minutes. The resultant ITO-patterned glass substrate was loaded onto a vacuum deposition apparatus.
HT3 and F6-TCNNQ were vacuum co-deposited on the anode at the weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and then, HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å. H-H1 was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 300 Å.
Next, a host and a dopant were co-deposited on the electron blocking layer at a weight ratio described in Table 12 to form an emission layer having a thickness of 400 Å.
H-H1 and H-H2 were used at a weight ratio of 5:5 as the host, and the first compound and second compound described in Table 12 were used at a weight ratio of 1:1 as the dopant.
Afterwards, ET3 and ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and A1 was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of OLED 1.
Manufacture of OLEDs 2 to 6 and A to C
OLEDs 2 to 6 and A to C were manufactured in a similar manner as used to manufacture OLED 1, except that, in forming an emission layer, compounds described in Table 12 below were used as a dopant.
A driving voltage (volts, V), emission peak wavelength (λmax, nm), maximum value of external quantum efficiency (Max EQE, relative % to OLED A), and lifespan (LT97, relative % to OLED A) (hr) of each of OLEDs 1 to 6 and A to C were evaluated, and the results are shown in Tables 12 to 14. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as an apparatus for evaluation, the lifespan (LT97) (at 16,000 candela per square meter (cd/m2) or nit) was obtained by measuring the amount of time (hour, hr) that elapsed until luminance was reduced to 97% of the initial brightness (from the initial luminance, which is set as 100%), and the results are expressed as a relative value (%) to OLED A. Max EQE of Tables 12 to 14 was also expressed as a relative value (%) to OLED A.
It was confirmed that 1) referring to Table 12, OLED 1 emits green light, and improved or equivalent external quantum efficiency and improved lifespan characteristics, compared to those of each of OLEDs A to C, 2) referring to Table 12, each of OLEDs 3 and 4 emit green light, and have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of each of OLED C, 3) referring to Table 13, each of OLEDs 5 and 6 emit green light, and have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of each of OLEDs B and C, and 3) referring to Table 14, OLED 2 emits green light, and has improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics compared to those of OLED C.
An electronic device, for example, a light-emitting device, including the composition may have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics.
It should be understood that the one or more exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the FIGURE, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2021-0076312 | Jun 2021 | KR | national |
| 10-2022-0070184 | Jun 2022 | KR | national |
