Patent Application
20230089993
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application Nos. 10-2020-0156926, filed on Nov. 20, 2020, and 10-2021-0155885, filed on Nov. 12, 2021, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
One or more embodiments relate to a light-emitting device and an electronic apparatus including the same.
From among light-emitting devices, organic light-emitting devices are self-emission 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-transporting region may be located between the anode and the emission layer, and an electron-transporting 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-transporting region, and electrons provided from the cathode may move toward the emission layer through the electron-transporting 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.
One or more embodiments provide a light-emitting device having an emission layer and an electronic apparatus including the same.
Additional aspects will be set forth in part in the description, which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, a light-emitting device includes
a first electrode,
a second electrode facing the first electrode,
an emission layer between the first electrode and the second electrode,
the emission layer includes i) a first emission layer and ii) a second emission layer located between the first emission layer and the second electrode,
the first emission layer is in direct contact with the second emission layer,
the first emission layer includes a dopant, a first hole-transporting compound, and a first compound,
the second emission layer includes a dopant, a second hole-transporting compound, and a second compound,
the dopant included in the first emission layer and the dopant included in the second emission layer are identical to each other,
the first compound and the second compound are different from each other,
the absolute value of the difference between the highest occupied molecular orbital (HOMO) energy level of the second hole-transporting compound and the HOMO energy level of the second compound is 0.3 eV or less, and
the HOMO energy level of the second hole-transporting compound and the HOMO energy level of the second compound are negative values measured by using a photoelectron spectroscopy in air.
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
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.
It will be understood that when an element is referred to as being “on” another element, it can be directly on 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
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 herein.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.
“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items 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.
Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the figure Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.
“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% or 5% of the stated value.
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 disclosure 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.
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.
The light-emitting device may include: a first electrode; a second electrode facing the first electrode; and an emission layer located between the first electrode and the second electrode, wherein the emission layer may include i) a first emission layer; and ii) a second emission layer located between the first emission layer and the second electrode.
The first emission layer may be in direct contact with the second emission layer.
The first emission layer includes a dopant, a first hole-transporting compound, and a first compound, and the second emission layer includes a dopant, a second hole-transporting compound, and a second compound.
The dopant, the first hole-transporting compound, and the first compound included in the first emission layer may be different from each other.
The dopant, the second hole-transporting compound, and the second compound included in the second emission layer may be different from each other.
The total weight of the first hole-transporting compound and the first compound in the first emission layer may be greater than the weight of the dopant included in the first emission layer.
The total weight of the second hole-transporting compound and the second compound in the second emission layer may be greater than the weight of the dopant included in the second emission layer.
The dopant included in the first emission layer and the dopant included in the second emission layer may be identical to each other. The detailed description of the dopants is the same as described in the present specification.
In one or more embodiments, the dopant may be a phosphorescent dopant.
In one or more embodiments, the dopant may be a transition metal-containing organometallic compound.
In one or more embodiments, the dopant may be a transition metal-containing heteroleptic organometallic compound.
In one or more embodiments, the dopant may be an organometallic compound represented by Formula 1. Formula 1 will be described in detail later.
In one or more embodiments, the dopant includes a transition metal-containing organometallic compound, wherein the transition metal-containing organometallic compound includes a pyridine group, a benzimidazole group (or a naphthimidazole group), and a dibenzofuran group (or azadibenzofuran group, a dibenzothiophene group, or an azadibenzothiophene group), each of the pyridine group and the benzimidazole group (or a naphthimidazole group) may be attached to the transition metal of the transition metal-containing organometallic compound via nitrogen, and the dibenzofuran group (or azadibenzofuran group, a dibenzothiophene group, or an azadibenzothiophene group) may be attached to the transition metal of the transition metal-containing organometallic compound via carbon. The pyridine group, the benzimidazole group (or a naphthimidazole group), and the dibenzofuran group (or an azadibenzofuran group, a dibenzothiophene group, or an azadibenzothiophene group) may be optionally substituted with at least one R1. R1 is the same as described in connection with Formula 1.
In one or more embodiments, the dopant may be a transition metal-containing organometallic compound, and the transition metal-containing organometallic compound may include a group represented by —Si(Q3)(Q4)(Q5), a group represented by —Ge(Q3)(Q4)(Q5), or any combination thereof. —Si(Q3)(Q4)(Q5) and —Ge(Q3)(Q4)(Q5) are the same as described in connection with Formula 1.
Each of the first hole-transporting compound and the second hole-transporting compound may include at least one π electron rich C3-C60 cyclic group (for example, π electron rich C6-C60 cyclic group, such as a carbazole group, an indolocarbazole group, a benzene group, etc.) and may not include an electron-transporting group. Examples of the electron-transporting group include a cyano group, a fluoro group, a π electron-deficient nitrogen-containing C1-C60 cyclic group (for example, a π electron-deficient nitrogen-containing C5-C60 cyclic group), a phosphine oxide group, and a sulfoxide group.
In one or more embodiments, the first hole-transporting compound and the second hole-transporting compound may each be a compound represented by Formula 5. Formula 5 will be described in detail later.
In one or more embodiments, the first hole-transporting compound and the second hole-transporting compound may be different from each other.
In one or more embodiments, the first hole-transporting compound and the second hole-transporting compound may be identical to each other.
The first compound included in the first emission layer and the second compound included in the second emission layer may be different from each other.
In one or more embodiments, the first compound may be an electron-transporting compound. For example, the first compound may be a compound containing at least one electron-transporting group. The electron-transporting group may be a cyano group, a fluoro group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, a phosphine oxide group, a sulfoxide group, or a combination thereof.
In one or more embodiments, the first compound may be a compound represented by Formula 7. Formula 7 will be described in detail later.
The absolute value of the difference between the highest occupied molecular orbital (HOMO) energy level of the second hole-transporting compound included in the second emission layer and the HOMO energy level of the second compound included in the second emission layer may be about 0.3 eV or less. The second compound included in the second emission layer may be any compound that satisfies the absolute value relationship of the difference in HOMO energy levels as described above.
In one or more embodiments, the second compound may be a bipolar compound.
In one or more embodiments, the second compound may be a compound represented by Formula 9 below. Formula 9 is the same as described in the present specification.
The “HOMO energy level” is a found value measured by using a photoelectron spectroscopy in air, and is a negative value.
Hereinafter, the HOMO energy level relationship among the dopant, the first hole-transporting compound, the first compound, the second hole-transporting compound and the second compound will be described with reference to
The “HOMO energy level” illustrated in
The HOMO energy level of the first hole-transporting compound (HOMO(HT1)) may be smaller than the HOMO energy level of the second hole-transporting compound (HOMO(HT2)).
The minimum value from among the HOMO energy level of the first hole-transporting compound (HOMO(HT1)) and the HOMO energy level of the second hole-transporting compound (HOMO(HT2)) may be about −5.80 eV or more.
For example, the minimum value from among the HOMO energy level of the first hole-transporting compound (HOMO (HT1)) and the HOMO energy level of the second hole-transporting compound (HOMO (HT2)) may be about −5.80 eV or more, from about −5.80 eV to about −5.30 eV, from about −5.80 eV to about −5.40 eV, from about −5.70 eV to about −5.20 eV, from about −5.65 eV to about −5.20 eV, from about −5.70 eV to about −5.30 eV, from about −5.70 eV to about −5.40 eV, or from about −5.65 eV to about −5.45 eV.
In one or more embodiments, the HOMO energy level of the first hole-transporting compound (HOMO(HT1)) and the HOMO energy level of the second hole-transporting compound (HOMO(HT2)) may each be about −5.80 eV or more.
For example, the HOMO energy level of the first hole-transporting compound (HOMO(HT1)) and the HOMO energy level of the second hole-transporting compound (HOMO(HT2)) may each be about −5.80 eV or more, from about −5.80 eV to about −5.30 eV, from about −5.80 eV to about −5.40 eV, from about −5.70 eV to about −5.20 eV, from about −5.65 eV to about −5.20 eV, from about −5.70 eV to about −5.30 eV, from about −5.70 eV to about −5.40 eV, or from about −5.65 eV to about −5.45 eV.
The HOMO energy level of the first compound (HOMO(ET)) may be smaller than the HOMO energy level of the second compound (HOMO(BP)).
For example, the HOMO energy level of the first compound (HOMO(ET)) and the HOMO energy level of the second compound (HOMO(BP)) may be about −6.15 eV or more, or about −6.08 eV or more, respectively.
In one or more embodiments, the HOMO energy level of the second compound (HOMO(BP)) may be about −6.00 eV or more, about −5.90 eV or more, or about −5.80 eV or more.
The absolute value of the difference (ΔHOMO2) between the HOMO energy level of the second hole-transporting compound (HOMO(HT2)) and the HOMO energy level of the second compound (HOMO(BP)) may be about 0.30 eV or less, about 0.20 eV or less, about 0.16 eV or less, from about 0.001 eV to about 0.30 eV, from about 0.001 eV to about 0.20 eV, from about 0.001 eV to about 0.16 eV, from about 0.01 eV to about 0.20 eV, from about 0.01 eV to about 0.16 eV, from about 0.02 eV to about 0.16 eV, from about 0.03 eV to about 0.16 eV, from about 0.04 eV to about 0.16 eV, from about 0.05 eV to about 0.16 eV, from about 0.06 eV to about 0.16 eV, from about 0.07 eV to about 0.16 eV, from about 0.08 eV to about 0.16 eV, or from about 0.09 eV to about 0.16 eV.
The maximum value from among the HOMO energy level of the first hole-transporting compound (HOMO(HT1)), the HOMO energy level of the first compound (HOMO(ET)), the HOMO energy level of the second hole-transporting compound (HOMO(HT2)), and the HOMO energy level of the second compound (HOMO(BP)) may be smaller than the HOMO energy level of the dopant (HOMO(D)).
For example, the HOMO energy level of the dopant (HOMO(D)) may be from about −5.60 eV to about −5.20 eV, for ex ample, about −5.50 eV to about −5.25 eV.
In one or more embodiments, the first hole-transporting compound and the second hole-transporting compound may be different from each other, and may satisfy the condition of, as illustrated in
In the light-emitting device including the emission layer including the first emission layer and the second emission layer as described above, hole mobility in the second emission layer is improved, the electrical resistance of the emission layer is lowered when the light-emitting device is driven, and the exciton distribution into the second emission layer may be enlarged. Accordingly, the light-emitting device may have excellent characteristics in terms of driving voltage, luminescence efficiency, roll-off ratio and/or lifespan.
In one or more embodiments, in the second emission layer, the weight of the second compound may be the same as the weight of the second hole-transporting compound. In one or more embodiments, in the second emission layer, the weight of the second compound in the second emission layer may be greater than the weight of the second hole-transporting compound. In one or more embodiments, in the second emission layer, the weight of the second compound in the second emission layer may be less than the weight of the second hole-transporting compound. In one or more embodiments, in the second emission layer, the weight ratio of the second hole-transporting compound to the second compound may be from 2:8 to 8:2, for example, 3:7 to 7:3, or 4:6 to 6:4, or 5:5.
In one or more embodiments, the thickness of the second emission layer may be the same as the thickness of the first emission layer.
In one or more embodiments, the thickness of the second emission layer may be greater than the thickness of the first emission layer.
In one or more embodiments, the light emitted from the emission layer to the outside through at least one of the first electrode and the second electrode may not be white light.
In one or more embodiments, the light emitted from the emission layer to the outside through at least one of the first electrode and the second electrode may be green light having a maximum emission wavelength of about 500 nm to about 580 nm.
In one or more embodiments, the light-emitting device may further include a hole-transporting region located between the first electrode and the emission layer, and the hole-transporting region may not include a charge-generation layer or an emission layer. The hole-transporting region may include a hole injection layer, a hole-transporting layer, an electron-blocking layer, a buffer layer, or a combination thereof.
In one or more embodiments, the light-emitting device may further include an electron-transporting region located between the emission layer and the second electrode, and the electron-transporting region may not include a charge-generation layer and an emission layer. The electron-transporting region may include a hole-blocking layer, an electron-transporting layer, an electron injection layer, or any combination thereof.
In one or more embodiments, the emission layer may not include compounds of Group A:
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.
Formula 1 is shown below.
M(L1)n1(L2)n2
M in Formula 1 may be a transition metal.
For example, M may be a Period 1 transition metal, a Period 2 transition metal, or a Period 3 transition metal of the Periodic Table of Elements.
In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm)), or rhodium (Rh).
In one or more embodiments, M may be Ir, Pt, Os, or Rh.
In Formula 1, L1 may be a ligand represented by Formula 2A, and L2 may be a ligand represented by Formula 2B:
Formulae 2A and 2B are the same as described in the present specification.
n1 in Formula 1 may be 1, 2, or 3, wherein, when n1 is 2 or more, two or more of Li(s) may be identical to or different from each other.
n2 in Formula 1 may be 0, 1, or 2, wherein, when n2 is 2, two L2(s) may be identical to or different from each other.
The sum of n1 and n2 in Formula 1 may be 2 or 3. For example, the sum of the n1 and n2 may be 3.
In one or more embodiments, in Formula 1, i) M may be Ir, and the sum of n1 and n2 may be 3; or ii) M may be Pt, and the sum of n1 and n2 may be 2.
In one or more embodiments, in Formula 1, M may be Ir, and i) n1 may be 1 and n2 may be 2, or ii) n1 may be 2 and n2 may be 1.
L1 and L2 in Formula 1 may be different from each other.
Y1 to Y4 in Formulae 2A to 2B may be each independently be C or N. For example, Y1 and Y3 may each be N, and Y2 and Y4 may each be C.
Ring CY1 to ring CY4 in Formulae 2A and 2B may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, ring CY1 to ring CY4 may each independently be, i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensed ring in which two or more fourth rings are condensed with each other, or v) a condensed ring in which one or more third rings and one or more fourth rings are condensed with each other,
the third 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 fourth 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, ring CY1 to ring CY4 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 aza9H-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 isooxazole 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 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.
In one or more embodiments, ring CYC may 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 azaphenanthrene benzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza9H-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 isooxazole 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 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, ring CY2 and CY4 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 aza9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, or a benzene group condensed with a norbornane group.
In one or more embodiments, ring CY3 may 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 aza9H-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 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, ring CYC of Formula 2A may be a pyridine group, a benzimidazole group, a pyridinoimidazole group, or a pyrimidinoimidazole group.
In one or more embodiments, ring CY2 in Formula 2A may be 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, 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, or an azaphenanthrobenzoselenophene group.
In one or more embodiments, ring CY3 of Formula 2B may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine 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, ring CY4 of Formula 2B may be 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 benzene group condensed with a cyclohexane group, or a benzene group condensed with a norbornane group.
For example, ring CY1 and ring CY3 in Formulae 2A and 2B may be different from each other.
In one or more embodiments, ring CY2 and ring CY4 in Formulae 2A and 2B may be different from each other.
In one or more embodiments, ring CY1 to ring CY4 may be different from each other.
R1 to R4 in Formulae 2A and 2B 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 C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl 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)(Q9), or —P(Q8)(Q9). Q1 to Q9 are the same as described in the present specification.
In one or more embodiments, R1 to R4 in Formulae 2A and 2B 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 alkoxy group, or a C1-C20 alkylthio group;
a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with 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[2.2.2]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[2.2.2]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 any 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[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)a 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 benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl 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 azadibenzothiophenyl group, each unsubstituted or substituted with 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 (phenyl)C1-C10 alkyl group, a C1-C20 alkoxy 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[2.2.2]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[2.2.2]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 benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl 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 any 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 are each independently:
—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 deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
In one or more embodiments, R1 to R4 may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group unsubstituted or substituted with deuterium, 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 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 heterocycloalkyl group, a phenyl group, a deuterated a phenyl group, a fluorinated a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated a biphenyl group, a fluorinated a biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated a dibenzofuranyl group, a fluorinated a dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated a dibenzothiophenyl group, a fluorinated a dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated alkoxy group, a fluorinated C1-C20 alkoxy 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 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated a biphenyl group, a (C1-C20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated a dibenzofuranyl group, a (C1-C20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated a dibenzothiophenyl group, a (C1-C20 alkyl)dibenzothiophenyl group, or any combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
b1 to b4 in Formula 2A and 2B indicate the numbers of R1 to R4, respectively, and may each independently be an integer from 0 to 20. When b1 is 2 or more, two or more of R1(s) may be identical to or different from each other, when b2 is 2 or more, two or more of R2(s) may be identical to or different from each other, when b3 is 2 or more, two or more of R3(s) may be identical to or different from each other, and when b4 is 2 or more, two or more of R4(s) may be identical to or different from each other. For example, b1 to b4 may each independently be an integer from 0 to 8.
In one or more embodiments, n2 in Formula 1 may not be 0, b3 of Formula 2B may not be 0, and at least one of R3(s) in the number of b3 may be —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5). Q3 to Q5 are the same as described in the present specification.
For example, Q3 to Q5 may each independently be:
a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; or
a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any 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 deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
In one or more embodiments, Q3 to Q5 may be identical to each other.
In one or more embodiments, two or more of Q3 to Q5 may be different from each other.
In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition (1) to Condition (8):
Condition (1)
b1 in Formula 2A is not 0, and at least one of R1(s) in the number of b1 includes deuterium.
Condition (2)
b2 in Formula 2A is not 0, and at least one of R2(s) in the number of b2 includes deuterium.
Condition (3)
b3 in Formula 2B is not 0, and at least one of R3(s) in the number of b3 includes deuterium.
Condition (4)
b4 in Formula 2B is not 0, and at least one of R4(s) in the number of b4 includes deuterium.
Condition (5)
b1 in Formula 2A is not 0, and at least one of R1(s) in the number of b1 includes a fluoro group.
Condition (6)
b2 in Formula 2A is not 0, and at least one of R2(s) in the number of b2 includes a fluoro group.
Condition (7)
b3 in Formula 2B is not 0, and at least one of R3(s) in the number of b3 includes a fluoro group.
Condition (8)
b4 in Formula 2B is not 0, and at least one of R4(s) in the number of b4 includes a fluoro group
In one or more embodiments, R1 to R4 in Formulae 2A and 2B may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, 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 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5) (where Q3 to Q5 are the same as described in the present specification):
In Formulae 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145 and 10-201 to 10-354, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and OMe is a methoxy 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 9-230 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 9-637:
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 9-230 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:
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-354 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:
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-636:
In Formulae 2A and 2B, i) two or more of a plurality of R1(s) may be optionally linked 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, ii) two or more of a plurality of R2(s) may be optionally linked 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, iii) two or more of a plurality of R3(s) may be optionally linked 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, iv) two or more of a plurality of R4(s) may be optionally linked 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 the same as described in connection with R1.
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY1(1) to CY1(42):
In Formulae CY1(1) to CY1(42),
X19 is O, S, N(R19a), C(R19a)(R19b), or Si(R19a)(R19b), and R19a and R19b are the same as described in connection with R1, Y1 may be carbon or nitrogen, and
* indicates a binding site to M in Formula 1, and *″ indicates a binding site to a neighboring carbon atom in Formula 2A.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY1(1) to CY1(22).
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY1(23) to CY1(42).
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(1) to CY2(40):
In Formulae CY2(1) to CY2(40),
T1 to T8 may each be carbon or nitrogen,
Y2 may be carbon or nitrogen,
X29 is O, S, N(R29a), C(R29a)(R29b), or Si(R29a)(R29b), and R29a and R29b are the same as described in connection with R2,
*′ indicates a binding site to M in Formula 1, and *″ indicates a binding site to ring CYC in Formula 2A.
For example, T1 to T8 in Formulae CY2(17) to CY2(40) may each be carbon.
In one or more embodiments,
at least one of T3 to T8 in Formula CY2(17) may be nitrogen,
at least one of T3, T4, T7 and T8 in Formula CY2(18) may be nitrogen,
at least one of T3, T4, T5 and T8 in Formula CY2(19) may be nitrogen,
at least one of T3, T4, T5 and T6 in Formula CY2(20) may be nitrogen,
at least one of T1, T2, T5, T6, T7 and T8 in Formula CY2(21) may be nitrogen,
at least one of T1, T2, T7 and T8 in Formula CY2(22) may be nitrogen,
at least one of T1, T2, T5 and T8 in Formula CY2(23) may be nitrogen,
at least one of T1, T2, T5 and T6 of Formula CY2(24) may be nitrogen,
at least one of T1, T4, T5, T6, T7 and T8 in Formula CY2(25) may be nitrogen,
at least one of T1, T4, T7 and T8 in Formula CY2(26) may be nitrogen,
at least one of T1, T4, T5 and T8 in Formula CY2(27) may be nitrogen,
at least one of T1, T4, T5 and T6 in Formula CY2(28) may be nitrogen,
at least one of T2, T4, T5, T6, T7 and T8 in Formula CY2(29) may be nitrogen,
at least one of T2, T4, T7 and T8 in Formula CY2(30) may be nitrogen,
at least one of T2, T4, T5 and T8 in Formula CY2(31) may be nitrogen,
at least one of T2, T4, T5 and T6 of Formula CY2(32) may be nitrogen,
at least one of T1, T2, T5, T6, T7 and T8 in Formula CY2(33) may be nitrogen,
at least one of T1, T2, T7 and T8 in Formula CY2(34) may be nitrogen,
at least one of T1, T2, T5 and T8 in Formula CY2(35) may be nitrogen,
at least one of T1, T2, T5 and T6 of Formula CY2(36) may be nitrogen,
at least one of T3 to T8 of Formula CY2(37) may be nitrogen,
at least one of T3, T4, T7 and T8 of Formula CY2(38) may be nitrogen,
at least one of T3, T4, T5 and T8 in Formula CY2(39) may be nitrogen, or
at least one of T3 to T6 of Formula CY2(40) may be nitrogen.
In one or more embodiments, in Formulae CY2(17) to CY2(40), T8 may be N and T1 to T7 may each be carbon.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(17) to CY2(40).
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by Formula CY3(1):
In Formula CY3(1),
Y3 may be carbon or nitrogen,
X31 may be Si or Ge, and
R3 and Q3 to Q5 are the same as described in the present specification,
b33 may each independently be an integer from 0 to 3,
two or more of R3(s) in the number of b33 may optionally be linked 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 (for example, a cyclohexane group, a norbornane group, a benzene group, a pyridine group, a naphthalene group, a quinoline group, or an isoquinoline group, each unsubstituted or substituted with at least one R10a),
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to ring CY4 in Formula 2B.
For example, at least one of R3(s) in the number of b33 in Formula CY3(1) may include two or more of carbon.
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by one of Formulae CY3-1 to CY3-16:
In Formulae CY3-1 to CY3-16,
R31 to R34 are the same as described in connection with R3, and each of R31 to R34 is not hydrogen,
Y3 may be carbon or nitrogen
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to ring CY4 in Formula 2B.
For example, R32 in Formulae CY3-1 to CY3-16 may be a C1-C10 alkyl group substituted with at least one deuterium; —Si(Q3)(Q4)(Q5); or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, R33 in Formulae CY3-1 to CY3-16 may include two or more of carbons.
In one or more embodiments, R33 and R34 in Formulae CY3-1 to CY3-16 may optionally be linked 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 (for example, a cyclohexane group, a norbornane group, a benzene group, a pyridine group, a naphthalene group, a quinoline group, or an isoquinoline group, each unsubstituted or substituted with at least one R10a).
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by Formula CY3-3, CY3-6, CY3-9, CY3-10, CY3-12, CY3-13, CY3-15, or CY3-16, and R32 in Formulae CY3-3, CY3-6, CY3-9, CY3-10, CY3-12, CY3-13, CY3-15 and CY3-16 may be —Si(Q3)(Q4)(Q5); or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by one of Formulae CY4-1 to CY4-16:
In Formulae CY4-1 to CY4-16,
Y4 may be carbon or nitrogen, R41 to R44 are the same as described in connection with R4, and each of R41 to R44 is not hydrogen,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to ring CY3 in Formula 2B.
In one or more embodiments, the organometallic compound represented by Formula 1 may emit green light with a maximum emission wavelength in the range of about 500 nm to about 580 nm (in photoluminescence (PL) spectrum).
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 1 or Condition 2:
Condition 1
A group represented by
in Formula 2A is a group represented by one of Formulae CY1(1) to CY1(22), and
a group represented by
in Formula 2A is a group represented by one of Formulae CY2(17) to CY2(40), and
a group represented by
in Formula 2B is a group represented by Formula CY3(1) (for example, a group represented by Formula CY3-3, CY3-6, CY3-9, CY3-10, CY3-12, CY3-13, CY3-15, or CY3-16 in which R32 is —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5)), and
a group represented by
in Formula 2B is a group represented by one of Formulae CY4-1 to CY4-16.
Condition 2
A group represented by
in Formula 2A is a group represented by one of Formulae CY1(23) to CY1(42),
a group represented by
in Formula 2A is a group represented by one of Formulae CY2(17) to CY2(40),
a group represented by
in Formula 2B is a group represented by Formula CY3(1) (for example, a group represented by Formula CY3-3, CY3-6, CY3-9, CY3-10, CY3-12, CY3-13, CY3-15, or CY3-16 in which R32 is —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5)), and
a group represented by
in Formula 2B is a group represented by one of Formulae CY4-1 to CY4-16.
Ar1, Ar2, Ar11, Ar101, and Ar102 in Formulae 5, 7, and 9 may each independently be a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50 or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50,
Ar91 in Formula 9 may be a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R90, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R90,
Ar5 and Ar12 in Formulae 5 and 7 may each independently be a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50a, or may not exist,
n6 in Formula 5 may be 1, 2, or 3, and when n6 is 1, Ar5 may not exist,
p in Formula 7 may be 1, 2, or 3, and when p is 1, Ar12 may not exist,
a1 and a2 in Formula 5 may each independently be an integer from 0 to 5, and the sum of a1 and a2 may be 1 or more,
ring CY51, ring CY52, ring CY91 and ring CY92 in Formulae 5 and 9 may each independently be a C5-C60 carbocyclic group or a C1-C60 heterocyclic group, and ring CY51 and ring CY52 may be optionally combined with each other with a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50b or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50b therebetween,
L5 in Formula 5 may be a single bond, O, S, N(R50c), C(R50c)(R50d), or Si(R50c)(R50d), and n5 may be 0 or 1, wherein, when n5 is 0, L5 may not exist,
Het1 in Formula 7 may be a π electron-deficient nitrogen-containing C1-C60 cyclic group, and
a11, a91 and m in Formulae 7 and 9 may each independently be an integer from 1 to 10,
In Formula 9, X101 may be N or C(R101), X102 may be N or C(R102), X103 may be N or C(R103), and at least two of X101 to X103 may be N, and
X91 in Formula 9 may be a single bond, O, S, N(R91a), C(R91a)(R91b), or Si(R91a)(R91b).
The term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a cyclic group having 1 to 60 carbon atoms including at least one *—N=*′ as a ring-constituting moiety, and may be, for example, a) a first ring, b) a condensed ring in which two or more first rings are condensed with each other, or c) a condensed ring in which at least one first ring is condensed with at least one second ring. The first ring and the second ring are the same as described in the present specification.
The π electron-deficient nitrogen-containing C1-C60 cyclic group may be, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, a (benzothieno)phenanthrene group, or a pyridopyrazine group.
The term “π electron-rich C6-C60 cyclic group” used herein refers to a cyclic group having 3 to 60 carbon atoms not including *—N=*′ as a ring-constituting moiety, and may be, for example, a) a second ring or b) a condensed cyclic group in which two or more second rings are condensed with each other. The second ring are the same as described in the present specification.
The π electron-rich C6-C60 cyclic group may be, for example, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, a pyrrolophenanthrene group, a furanophenanthrene group, or a thienophenanthrene group.
In some embodiments,
Ar1, Ar2, Ar11, Ar101 and Ar102 in Formulae 5, 7 and 9 may each independently be a group derived from i) a first ring unsubstituted or substituted with at least one R50, ii) a second ring unsubstituted or substituted with at least one R50, iii) a condensed cyclic group in which two or more first rings, substituted or unsubstituted with at least one R50, are condensed with each other, iv) a condensed cyclic group in which two or more second rings, substituted or unsubstituted with at least one R50, are condensed with each other, or v) a condensed cyclic group in which at least one first ring unsubstituted or substituted with at least one R50 is condensed with at least one second ring unsubstituted or substituted with at least one R50,
Ar91 in Formula 9 may be a single bond, or a group derived from i) a first ring unsubstituted or substituted with at least one R90, ii) a second ring unsubstituted or substituted with at least one R90, iii) a condensed cyclic group in which two or more first rings, unsubstituted or substituted with at least one R90, are condensed with each other, iv) a condensed cyclic group in which two or more second rings, unsubstituted or substituted with at least one R90, are condensed with each other, or v) a condensed cyclic group in which at least one first ring unsubstituted or substituted with at least one R90 is condensed with at least one second ring unsubstituted or substituted with at least one R90,
Ar5 and Ar12 in Formulae 5 and 7 may each independently be a single bond, or a group derived from i) a first ring unsubstituted or substituted with at least one R50a, ii) a second ring unsubstituted or substituted with at least one R50a, iii) a condensed cyclic group in which two or more first rings, substituted or unsubstituted with at least one R50a, are condensed with each other, iv) a condensed cyclic group in which two or more second rings, substituted or unsubstituted with at least one R50a, are condensed with each other, or v) a condensed cyclic group in which at least one first ring unsubstituted or substituted with at least one R50a is condensed with at least one second ring unsubstituted or substituted with at least one R50a, or may not exist,
ring CY51, ring CY52, ring CY91 and ring CY92 in Formulae 5 and 9 may each independently 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 one or more first rings and one or more second rings are condensed with each other,
Het1 in Formula 7 may be a group derived from i) a first ring, ii) a condensed cyclic group in which two or more first rings are condensed with each other or iii) a condensed cyclic group in which at least one first ring is condensed with at least one second ring,
the first ring may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, or a thiadiazole group, and the second ring may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.
In one or more embodiments, Ar1, Ar2, Ar11, Ar101 and Ar102 in Formulae 5, 7, and 9 may each independently be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group, each unsubstituted or substituted with at least one R50.
In one or more embodiments, Ar91 in Formula 9 may be a single bond, or a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, an (an indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group, each unsubstituted or substituted with at least one R90.
In one or more embodiments, Ar5 and Ar12 in Formulae 5 and 7 may each independently be a single bond, or a benzene group, a naphthalene group, or a carbazole group, each unsubstituted or substituted with at least one R50a, or may not exist.
In one or more embodiments, ring CY51, ring CY52, ring CY91 and ring CY92 of Formulae 5 and 9 may each independently be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, an acridine group, a dihydroacridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyrrolophenanthrene group, a furanophenanthrene group, or a thienophenanthrene group.
In one or more embodiments, Het1 in Formula 7 may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, or a pyridopyrazine group.
In one or more embodiments, Ar1, Ar2, Ar11, Ar101 and Ar102 in Formulae 5, 7, and 9 may each independently be a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R50.
In one or more embodiments, Ar91 in Formula 9 may be a single bond, or a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R90.
In one or more embodiments, Ar5 and Ar12 in Formulae 5 and 7 may each independently be a single bond or a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R50a, or may not exist.
In one or more embodiments, ring CY51, ring CY52, ring CY91, and ring CY92 in Formulae 5 and 9 may each independently be a π electron-rich C3-C60 cyclic group.
In one or more embodiments, ring CY91 and ring CY92 in Formula 9 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In one or more embodiments, one of ring CY91 and ring CY92 in Formula 9 may be a benzene group, a naphthalene group, or a phenanthrene group, and the other one may be a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In one or more embodiments, n6 and p in Formulae 5 and 7 may each independently be 1 or 2.
In one or more embodiments, when n6 in Formula 5 is 1, at least one of ring CY51 and ring CY52 may not be a benzene group.
In one or more embodiments, when n6 in Formula 5 is 1, at least one of ring CY51 and ring CY52 may be a) a condensed ring in which two or more first rings are condensed with each other, b) a condensed ring in which two or more second rings are condensed with each other, or c) a condensed ring in which at least one first ring is condensed with at least one second ring. In this regard, the first ring and the second ring are the same as described in the present specification.
In one or more embodiments, the compound represented by Formula 5 may be a compound represented by Formula 5(1):
In Formula 5(1),
Ar5 may be a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50a,
Ar1, Ar2, Ar5, a1, a2, ring CY51, ring CY52, R51, R52, b51, and b52 are the same as described in the present specification,
Ar3 and Ar4 may each independently be a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50 or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50,
a3, a4, ring CY53, ring CY54, R53, R54, b53, and b54 are the same as described in connection with a1, a2, ring CY51, ring CY52, R51, R52, b51, and b52, respectively.
For example, Ar5 in Formula 5(1) may be a single bond.
In one or more embodiments, the compound represented by Formula 7 may include a compound represented by Formula 7(1):
In Formula 7(1),
Ar12 may be a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R50a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R50a,
Het1, Ar11, R70, R80, a11, b7, b8, and m are the same as described in the present specification, and
Het3, Ar13, R73, R83, a13, b73, b83, and m3 are the same as described in connection with Het1, Ar11, R70, R80, a11, b7, b8, and m, respectively.
In one or more embodiments, a group represented by
in Formula 5, a group represented by
in Formula 5(1) and a group represented by
in Formula 5(1) may each independently be a group represented by one of Formulae 2-1 to 2-93:
In Formulae 2-1 to 2-93,
X51 may be O, S, N(R51a), C(R51a)(R51b), or Si(R51a)(R51b),
X52 may be O, S, N(R52a), C(R52a)(R52b), or Si(R52a)(R52b), R51a, R51b, R52a, and R52b are the same as described in connection with R51, and
* indicates a binding site to Ar1 or Ar2 in Formula 5 or 5(1).
In one or more embodiments, Het1 in Formula 7 and Het1 and Het3 in Formula 7(1) may each independently be a group derived from one of Formulae 3-1 to 3-40:
In one or more embodiments, a group represented by
in Formula 9 may be a group represented by one of Formulae 9-1 to 9-6:
In Formulae 9-1 to 9-6,
X91 is the same as described above,
X92 may be O, S, N(R92a), C(R92a)(R92b), or Si(R92a)(R92b), and
* indicates a binding site to an adjacent atom.
In one or more embodiments, X101 to X103 in Formula 9 may be N.
a1 and a2 in Formulae 5 and 5(1) may indicate the number of Ar1(s) and the number of Ar2(s), respectively, and may each independently be an integer from 0 to 5 (for example, 0, 1, or 2), and the sum of a1 and a2 may be 1 or more. When a1 is 2 or more, two or more of Ar1(s) may be identical to or different from each other, and when a2 is 2 or more, two or more of Ar2(s) may be identical to each other or different from each other. When a1 is 0, *—(Ar1)a1—*′ in Formula 2 may be a single bond.
a11 and m in Formulae 7 and 7(1) indicate the number of Ar11(s) and the number of *—(Ar11)a11—(R70)a70 (s), respectively, and may each independently be an integer from 1 to 10. When a11 is 2 or more, two or more of Ar11(s) may be identical to or different from each other, and when m is 2 or more, two or more of *—(Ar11)a11—(R70)a70(s) may be identical to or different from each other.
In one or more embodiments, a11 and m in Formulae 7 and 7(1) may each independently be an integer from 1 to 3.
a91 in Formula 9 indicates the number of Ar91(s), and may be an integer from 1 to 10.
R50 to R54, R50a to R50d, R51a, R51b, R52a, R52b, R70, R73, R80, R83, R90 to R92, R91a, R91b, R92a, R92b, and R101 to R103 used herein may each independently be hydrogen, deuterium, —F, —Cl, —Br, —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 C3-C10 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl 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 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)(Q9), or —P(Q8)(Q9). Q1 to Q9 are the same as described in the present specification.
For example, R50 to R54, R50a to R50d, R51a, R51b, R52a, R52b, R70, R73, R80, R83, R90 to R92, R91a, R91b, R92a, R92b, and R101 to R103 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, or a C1-C20 alkoxy group; a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl 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 (norbornanyl 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)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 silolanyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl 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 silolanyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl 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 benzimidazolyl 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 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl 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)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 silolanyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl 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 benzimidazolyl 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 any combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q8)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 are each independently:
—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 deuterium, a C1-C20 alkyl group, a phenyl group, or any combination thereof.
b51 to b54, b7, b73, b8, b83, b91, and b92 indicates the numbers of R51 to R54, R70, R73, R80, R83, R91, and R92, respectively, and may each independently be an integer from 0 to 20. For example, b51 to b54, b7, b73, b8, b83, b91, and b92 may each independently be an integer from 0 to 10. when b51 is 2 or more, two or more of R51(s) may be identical to or different from each other, when b52 is 2 or more, two or more of R52(s) may be identical to or different from each other, when b53 is 2 or more, two or more of R53(s) may be identical to or different from each other, when b54 is 2 or more, two or more of R54(s) may be identical to or different from each other, when b7 is 2 or more, two or more of R70(s) may be identical to or different from each other, when b73 is 2 or more, two or more of R73(s) may be identical to or different from each other, when b8 is 2 or more, two or more of R80(s) may be identical to or different from each other, when b83 is 2 or more, two or more of R83(s) may be identical to or different from each other, when b91 is 2 or more, two or more of R91(s) may be identical to or different from each other, when b92 is 2 or more, two or more of R92(s) may be identical to or different from each other.
For example, R50 to R54, R50a to R50d, R51a, R51b, R52a, R52b, R70, R73, R80, R83, R90 to R92, R91a, R91b, R92a, R92b, and R101 to R103 may each independently be:
hydrogen or deuterium;
a C1-C29 alkyl group or a C1-C29 alkoxy group, each substituted or unsubstituted with deuterium, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C1-C10 alkyl)fluorenyl group, a di(C6-C69 aryl)fluorenyl group, a dibenzosilolyl group, a di(C1-C10 alkyl)dibenzosilolyl group, a di(C6-C60 aryl)dibenzosilolyl group, a carbazolyl group, a (C1-C10 alkyl)carbazolyl group, a (C6-C60 aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, —N(Q31)(Q32), or any combination thereof;
a π electron-rich C3-C60 cyclic group, unsubstituted or substituted with deuterium, a C1-C29 alkyl group, a C1-C29 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a alkyl)fluorenyl group, a di(C6-C60 aryl)fluorenyl group, a dibenzosilolyl group, a alkyl)dibenzosilolyl group, a di(C6-C60 aryl)dibenzosilolyl group, a carbazolyl group, a (C1-C10 alkyl)carbazolyl group, a (C6-C60 aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, —N(Q31)(Q32), or any combination thereof; or
—N(Q1)(Q2).
In this regard, Q1, Q2, Q31, and Q32 are the same as described in the present specification.
In one or more embodiments, R50 to R54, R50a to R50d, R51a, R51b, R52a, R52b, R70, R73, R80, R83, R90 to R92, R91a, R91b, R92a, R92b, and R101 to R103 may each independently be:
hydrogen or deuterium;
a C1-C29 alkyl group unsubstituted or substituted with deuterium, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C1-C10 alkyl)fluorenyl group, a di(C6-C60 aryl)fluorenyl group, a dibenzosilolyl group, a di(C1-C10 alkyl)dibenzosilolyl group, a di(C6-C60 aryl)dibenzosilolyl group, a carbazolyl group, a (C1-C10 alkyl)carbazolyl group, a (C6-C60 aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, —N(Q31)(Q32), or any combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a dibenzosilolyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a di(C1-C10 alkyl)fluorenyl group, a di(C6-C60 aryl)fluorenyl group, a dibenzosilolyl group, a di(C1-C10 alkyl)dibenzosilolyl group, a di(C6-C60 aryl)dibenzosilolyl group, a carbazolyl group, a (C1-C10 alkyl)carbazolyl group, a (C6-C60 aryl)carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
In this regard, Q31 and Q32 are the same as described in the present specification.
In Formulae 5, 7, and 9, 1) two or more of R51(s) may optionally be combined with each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, 2) two or more of R52(s) may optionally be combined with each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and 3) two or more of ring CY51, ring CY52, R51, and R52 may optionally be combined with each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a. R10a may be the same as described in connection with R1.
In one or more embodiments, the dopants included in the first emission layer and the second emission layer may be one of compounds of Group 1-1 to Group 1-7:
In compounds 1 to 1621 of [Group 1-1], OMe represents a methoxy group.
In one or more embodiments, the first hole-transporting compound and the second hole-transporting compound may each independently be at least one of Compounds H1-1 to H1-72 of [Group 5-1], Compounds H1-1 to H1-20 of [Group 5-2], or a combination thereof:
In one or more embodiments, the first compound may be at least one of Compounds E1-1 to E1-62:
In one or more embodiments, the second compound may be at least one of Compounds BP1-1 to BP1-17:
Description of
The organic light-emitting device 10 of
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 organic light-emitting devices available in the 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.
In one or more embodiments, 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 be selected from 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), 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, but the structure of the first electrode 11 is not limited thereto.
The hole-transporting region 13 may be located between the first electrode 11 and the emission layer 15.
The hole-transporting region 13 may include a hole injection layer, a hole-transporting layer, an electron-blocking layer, a buffer layer, or a combination thereof.
The hole-transporting region 13 may include only a hole injection layer or only a hole-transporting layer. In one or more embodiments, the hole-transporting region 13 may have a hole injection layer/hole-transporting layer structure or a hole injection layer/hole-transporting layer/electron-blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
When the hole-transporting region 13 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 (LB) 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 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 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. However, the coating conditions are not limited thereto.
The conditions for forming the hole-transporting layer and the electron-blocking layer may be the same as the conditions for forming the hole injection layer.
The hole-transporting region 13 may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, 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 sulfonicacid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:
Ar101 and Ar102 in Formula 201 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 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 C1-C60 alkoxy 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any 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, but xa and xb are not limited thereto.
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, 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 (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, or the like) or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like);
a C1-C10 alkyl group or a C1-C10 alkoxy group, each unsubstituted or substituted with 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, or any combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group or a pyrenyl group, each unsubstituted or substituted with 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-C10 alkyl group, a C1-C10 alkoxy group, or any combination thereof.
R109 in Formula 201 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with 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-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A:
R101, R111, R112, and R109 in Formula 201A may be understood by referring to the description provided herein.
For example, the hole-transporting region 13 may include one of Compounds HT1 to HT20 or any combination thereof:
The thickness of the hole-transporting region 13 may be from about 100 Å to about 10000 Å, for example about 100 Å to about 1000 Å. When the hole-transporting region 13 includes a hole injection layer, a hole-transporting layer, an electron-blocking layer or a combination thereof, the 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-transporting 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-transporting region, the hole injection layer and the hole-transporting layer are within these ranges, satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
In addition to the above-described materials, the hole-transporting region 13 may further include a charge-generation material to improve conductivity. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole-transporting region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may include a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination. For example, the p-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 any combination thereof.
The hole-transporting region 13 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, efficiency of a formed organic light-emitting device may be improved.
Meanwhile, when the hole-transporting region 13 includes an electron-blocking layer, the material for the electron-blocking layer may include a material that can be used in the hole-transporting region 13 as described above, a host material, or a combination thereof. For example, when the hole-transporting region includes an electron-blocking layer, mCP, Compound H1-8 of [Group 5-2], or the like may be used as a material for the electron-blocking layer.
The emission layer 15 may be formed on the hole-transporting region 13 by using, for example, a vacuum deposition method, a spin coating method, a cast method, or an LB method. When the emission layer 15 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 depending on a material that is used to form the emission layer.
The emission layer 15 may include a first emission layer 15-1 and a second emission layer 15-2 as described herein.
The amount (weight) of the dopant in the first emission layer 15-1 may be from about 0.01 to about 20 parts by weight based on 100 parts by weight, which is the total weight of the first hole-transporting compound and the first compound.
The amount (weight) of the dopant in the second emission layer 15-2 may be from about 0.01 to about 20 parts by weight based on 100 parts by weight, which is the total weight of the second hole-transporting compound and the second compound.
A thickness of the emission layer 15 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 15 is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Next, the electron-transporting region 17 may be located on the emission layer 15.
The electron-transporting region 17 may include a hole-blocking layer, an electron-transporting layer, an electron injection layer, or a combination thereof.
For example, the electron-transporting region 17 may have a hole-blocking layer/electron-transporting layer/electron injection layer structure or an electron-transporting layer/electron injection layer structure. The electron-transporting layer may have a single-layered structure or a multi-layered structure including two or more different materials.
The conditions for the formation of the hole-blocking layer, the electron-transporting layer and the electron injection layer in the electron-transporting region 17 are the same as the conditions for the formation of the hole injection layer.
When the electron-transporting region 17 includes a hole-blocking layer, the hole-blocking layer may include, for example, at least one of the following BCP, Bphen and BAlq.
In one or more embodiments, the hole-blocking layer may include any host material, and a material for an electron-transporting layer, a material for an electron injection layer, or a combination thereof, which will be described later.
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 300 Å. When the thickness of the hole-blocking layer is within these ranges, excellent hole-blocking characteristics can be obtained without a substantial increase in driving voltage.
The electron-transporting layer may include BCP, Bphen, TPBi, Alq3, Balq, TAZ, NTAZ, or any combination thereof:
In one or more embodiments, the electron-transporting layer may include at least one of Compounds ET1 to ET25.
A thickness of the electron-transporting 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-transporting layer is within the range described above, the electron-transporting layer may have satisfactory electron-transporting characteristics without a substantial increase in driving voltage.
The electron-transporting 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:
In one or more embodiments, the electron-transporting region 17 may include an electron injection layer (EIL) that facilitates injection of electrons from the second electrode 19.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any 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, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
A second electrode 19 may be provided on the electron-transporting region 17. 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), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) 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.
Hereinbefore, the organic light-emitting device has been described with reference to
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, and 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 herein 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 are 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 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 any 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” used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof are a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy 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, and a butenyl group. 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, and a propynyl group. 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 are 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, and a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monocyclic 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 C1-C10 heterocycloalkylene group refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
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, and a cycloheptenyl group. 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 are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. 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, and a chrysenyl group. 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 C7-C60 alkylaryl group used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having 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 having at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a carbocyclic 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 rings may be fused to each other.
The C2-C60 alkylheteroaryl group used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 indicates the C6-C60 aryl group), the C6-C60 arylthio group indicates —SA103 (wherein A103 indicates the C6-C60 aryl group), and the C1-C60 alkylthio group indicates —SA104 (wherein A104 indicates the C1-C60 alkyl 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, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. 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 heterocondensed polycyclic 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, and 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” used herein include i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensed ring in which two or more fourth rings are condensed with each other, or v) a condensed ring in which at least one third ring is condensed with at least one fourth ring, the third 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 fourth 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” 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 a 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 heterocycloalkyl group,” and “deuterated phenyl group” 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 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 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein are substituted with 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 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein are 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” 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, and 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 C2-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 alkylaryl 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 monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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-C60 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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-C10heterocycloalkenyl 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any 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 monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10heterocycloalkenyl 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof,
Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 described herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro 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 which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; 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 which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
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 deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
As used herein, the number of carbons in each group that is substituted (e.g., C1-C60) excludes the number of carbons in the substituent. For example, a C1-C60 alkyl group can be substituted with a C1-C60 alkyl group. The total number of carbons included in the C1-C60 alkyl group substituted with the C1-C60 alkyl group is not limited to 60 carbons. In addition, more than one C1-C60 alkyl substituent may be present on the C1-C60 alkyl group. This definition is not limited to the C1-C60 alkyl group and applies to all substituted groups that recite a carbon range.
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic 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.
4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (33.1 mmol) and iridium chloride (IrCl3(H2O)n) (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water and then, stirred under reflux for 24 hours, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed sufficiently with water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 7.4 g (74% of yield) of Compound 1390A.
Compound 1390A (1.2 mmol) and 45 mL of methylene chloride were mixed, and then, AgOTf (silver trifluoromethanesulfonate) (0.6 g, 2.3 mmol) was added thereto after being mixed with 15 mL of methanol. Thereafter, the mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then filtered through Celite to remove the resulting solid, and the filtrate was subjected to reduced pressure to obtain a solid (Compound 1390B). Compound 1390B was used in the next reaction without an additional purification process.
Compound 1390B (2.3 mmol) and 1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(7-phenyldibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole (2.8 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide and then, stirred under reflux for 48 hours and then, the temperature was lowered to a room temperature. The obtained mixture was subjected to a reduced pressure to obtain a solid, on which column chromatography (eluent: methylene chloride (MC) and hexane) was performed to obtain 0.56 g (yield of 39%) of D-Ir(1) (Compound 1390 of [Group 1-3]). The obtained compound was identified by mass spectrometry (MS) and high performance liquid chromatography (HPLC) analysis.
High resolution mass spectrometry (matrix-assisted laser desorption ionization) (HRMS(MALDI)) calcd for C79H83IrN4OSi2: m/z 1352.5735 Found: 1352.5733
The HOMO energy levels of the following compounds were found by the measurement using a photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3) in air, and the found values are shown in Table 1.
An ITO (as an anode)-patterned glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water, each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
HT3 and F6-TCNNQ were vacuum 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-transporting layer having a thickness of 1,350 Å. HT(1) was vacuum-deposited on the hole-transporting layer to form an electron-blocking layer having a thickness of 300 Å.
Then, a first hole-transporting compound (HT(1)), a first compound (E1-62), and dopant (Ir(ppy)3) were co-deposited on the electron-blocking layer to form a first emission layer having a thickness of 100 Å (10 nm), and a second hole-transporting compound (HT(2)), a second compound (BP1-10), and dopant (Ir(ppy)3) were co-deposited on the first emission layer to form a second emission layer having a thickness of 300 Å (30 nm). The amount of the dopant in the first emission layer was 7 parts by weight based on 100 parts by weight of the first emission layer, the weight ratio of the first hole-transporting compound to the first compound in the first emission layer is shown in Table 2, and the amount of the dopant in the second emission layer was 7 parts by weight based on 100 parts by weight of the second emission layer, and the weight ratio of the second hole-transporting compound to the second compound in the second emission layers is shown in Table 2.
Then, ET3 and ET-D1 were co-deposited at the volume ratio of 50:50 on the emission layer to form an electron-transporting layer having a thickness of 350 Å, and ET-D1 was vacuum-deposited on the electron-transporting layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same method as in Example 1, except that the configuration of an emission layer was changed as described in Table 2 (Comparative Example 1 did not include a second emission layer and Comparative Example 2 did not include a first emission layer)
For each of the organic light-emitting devices manufactured in Example 1 and Comparative Examples 1 to 3, the driving voltage (V), maximum value of luminescence efficiency (cd/A), roll-off ratio (%), power efficiency (Im/W), and lifespan (LT97) were evaluated, and the results are shown in Table 3. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifespan (LT97) (at 8000 nit) was evaluated as the time taken for luminance to reduce to 97% of 100% of the initial luminance. Lifespan (LT97) of Table 3 was represented as a relative value (%). The roll-off ratio was calculated according to Equation 20 below.
Roll-off ratio={1−(luminescence efficiency (at 8000 nit)/maximum luminescence efficiency)}×100% <Equation 20>
From Table 3, it is confirmed that the organic light-emitting device of Example 1 has improved characteristics in terms of driving voltage, luminescence efficiency, roll-off ratio, power efficiency and lifespan, compared to the organic light-emitting devices of Comparative Examples 1 to 3.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the configuration of an emission layer is changed as shown in Table 4.
For each of the organic light-emitting devices manufactured according to Examples 11 to 16, the driving voltage (V), the maximum value of luminescence efficiency (cd/A), the roll-off ratio (%), power efficiency (Im/W), and the lifespan (LT97) were evaluated by using the same method as described in Evaluation Example 2, and the results are shown in Table 5. For reference, the data of Comparative Example 3 are shown in Table 5.
From Table 5, it can be seen that the organic light-emitting devices of Examples 11 to 16 have excellent characteristics in terms of driving voltage, luminescence efficiency, roll-off ratio, power efficiency and lifespan.
Light-emitting devices according to embodiments of the present disclosure have excellent characteristics in terms of driving voltage, luminescence efficiency, roll-off ratio, power efficiency and lifespan. Accordingly, high-quality electronic devices can be manufactured using the light-emitting devices.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, 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 |
|---|---|---|---|
| 10-2020-0156926 | Nov 2020 | KR | national |
| 10-2021-0155885 | Nov 2021 | KR | national |
