This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2020-0121785, filed on Sep. 21, 2020, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
Provided is an organic light-emitting device including an emission layer that satisfies a predetermined condition.
Organic light-emitting devices are self-emission devices that produce full-color images, and also have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed, compared to devices in the art.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state to thereby generate light.
Provided is an organic light-emitting device including an emission layer that satisfies a certain condition.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect, provided is an organic light-emitting device including: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer, the emission layer includes a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and the emission layer satisfies Condition 1 below:
⊖H+S+E/⊖H+S×100>109(%). Condition 1
In Condition 1,
⊖H+S+E is a horizontal orientation ratio of the emission layer, and
⊖H+S is a horizontal orientation ratio of a thin film consisting of the host and the sensitizer included in the emission layer.
According to another aspect, provided is an organic light-emitting device including: a first electrode; a second electrode; and m emission units located between the first electrode and the second electrode and including at least one emission layer; and m−1 charge generation layers located between two adjacent emission units of the m emission units and including an n-type charge generation layer and a p-type charge generation layer, wherein a maximum emission wavelength of light emitted from the at least one emission unit of the m emission units is different from a maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units, wherein at least one of emission layers includes a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and the at least one emission layer satisfies Condition 1.
According to another aspect, provided is an organic light-emitting device including: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, wherein m is an integer of 2 or more, a maximum emission wavelength of light emitted from the at least one emission layer of the m emission layers is different from a maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers, wherein at least one of the m emission layers includes a host, a sensitizer, and an emitter, wherein the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, a actinide metal, or any combination thereof, and the emission layers satisfy Condition 1.
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. 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 organic light-emitting device 10 of
The organic layer 10A includes an emission layer 15, a hole transport region 12 located between the first electrode 11 and the emission layer 15, and an electron transport region 17 located between the emission layer 15 and the second electrode 19.
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 general organic light-emitting devices 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 a material 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. When the first electrode 11 is a transmissive electrode, a material for forming a first electrode may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof, but embodiments of the present disclosure are not limited thereto.
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers.
The emission layer 15 includes a host, a sensitizer, and an emitter.
Since the emission layer 15 includes a host, a sensitizer, and an emitter and fluorescence or delayed fluorescence is emitted from the emitter, the organic light-emitting device 10 may have higher efficiency and/or longer lifespan than other organic light-emitting devices, for example, an organic light-emitting device that does not include a sensitizer, and particularly, an increase in the efficiency thereof may be remarkable. Without wishing to be bound by theory, triplet excitons formed at a host, which is 75% of the total excitons, are transferred to a sensitizer through Dexter energy transfer, and energy of singlet excitons formed at the host, which is 25% of the total excitons, is transferred to singlet and triplet of the sensitizer, wherein the singlet undergoes intersystem crossing into a triplet, and then, the triplet energy of the sensitizer is transferred to an emitter through Förster energy transfer. Accordingly, by transferring all the singlet excitons and the triplet excitons generated in the emission layer to an emitter, an organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device with significantly reduced energy loss may be obtained, the lifespan characteristics of the organic light-emitting device may be improved.
The emission layer 15 may satisfy the following Condition 1:
⊖H+S+E/⊖H+S×100>about 109(%). Condition 1
In Condition 1,
⊖H+S+E is a horizontal orientation ratio of the emission layer 15, and
⊖H+S is a horizontal orientation ratio of a thin film consisting of the host and the sensitizer included in the emission layer.
⊖H+S+E is a value obtained by preparing a quartz substrate having a thickness of 50 nm and formed by depositing the host, the sensitizer, and the emitter at a weight ratio of {100−(a+b)}:a:b, and comparing a graph obtained by measuring photoluminescence (PL) intensity of the same according to an angle of 0° to 90° with simulated graphs having different horizontal orientation ratios, for example, a horizontal orientation ratio of 100% and a horizontal orientation ratio of 67%. Here, a and b are each an arbitrary constant.
⊖H+S is a value obtained by preparing a quartz substrate having a thickness of 50 nm and formed by depositing the host and the sensitizer at a weight ratio of (100−c):c, and comparing a graph obtained by measuring PL intensity of the same according to an angle of 0° to 90° with simulated graphs having different horizontal orientation ratios, for example, a horizontal orientation ratio of 100% and a horizontal orientation ratio of 67%. Here, c is an arbitrary constant.
When Condition 1 is satisfied, improved spectral overlap may be secured, and thus, efficiency and/or lifespan of the organic light-emitting device may be increased.
In detail, ⊖H+S+E/⊖H+S×100 of the emission layer 15 may be about 140% or less, about 135% or less, about 111% or more, or about 110% or more.
In an embodiment, a spectral overlap integral (SOI) constant (J) of the sensitizer and the emitter is greater than or equal to about 1×1014. J is a value obtained from the following Equation 1:
In Equation 1,
λ is an emission wavelength (nm),
FD(A) is an emission spectrum of the sensitizer, and εA(A) is an extinction coefficient spectrum of the emitter.
When Equation 1 is satisfied, J may be greater than or equal to about 1×1014, energy transfer to the emitter may be efficiency performed. Accordingly, the efficiency of the organic light-emitting device 10 and the lifespan of the organic light-emitting device may be increased at the same time.
In an embodiment, the host, the emitter, and the sensitizer may further satisfy the following Condition 2:
T1(H)≥T1(S)≥S1(E). Condition 2
In Condition 2,
T1(H) is a lowest excitation triplet energy level of the host,
S1(E) is a lowest excitation singlet energy level of the emitter, and
T1(S) is a lowest excitation triplet energy level of the sensitizer.
When the host, the emitter, and the sensitizer satisfy Condition 2, triplet excitons may be effectively transferred from the emission layer to the emitter, and thus, an organic light-emitting device having improved efficiency may be obtained. In addition, when Condition 2 is further satisfied, only the emitter substantially emits light in the emission layer, and thus, a horizontal orientation ratio of the emission layer may vary according to a type of the emitter, regardless of the composition of the emission layer.
In an embodiment, the host and the sensitizer may further satisfy the following Condition 3:
T1(H)>T1(S). Condition 3
In Condition 3,
T1(H) is a lowest excitation triplet energy level of the host, and
T1(S) is a lowest excitation triplet energy level of the sensitizer.
When the host and the sensitizer further satisfy Condition 3, in an emission layer consisting of the host and the sensitizer, only the sensitizer substantially emits light, and thus, a horizontal orientation ratio of the emission layer may vary according to a type of the sensitizer, regardless of the composition of the emission layer.
In an embodiment, ⊖H+S+E may be greater than or equal to about 80%. Because ⊖H+S+E is greater than or equal to 80%, the efficiency and/or the lifespan may be improved. In detail, because ⊖H+S+E is greater than or equal to about 80%, during the organic light-emitting device 10 is driven, an electric field may be emitted in a substantially horizontal direction (i.e., a direction parallel to the first electrode) with respect to the emission layer, and thus, optical loss due to a waveguide mode and/or a surface plasmon polariton mode may be reduced. Light emitted by such a mechanism may have high external extraction efficiency, and the organic light-emitting device 10 may achieve high luminescence efficiency.
In detail, ⊖H+S+E may be, for example, about 84% or more, about 87% or more, about 90% or more, about 93% or more, about 96% or more, about 99% or more, or 100% or less.
Among total emission components emitted from the emission layer, a proportion of emission components emitted from the emitter may be greater than or equal to about 80%. In an embodiment, the emitter may be a delayed fluorescence dopant emitting delayed fluorescence. A proportion of delayed fluorescence components to total emission components in time-resolved photoluminescence (TRPL) of the emitter may be about 85% or more, for example, about 90% or more, about 95% or more, or about 99% or more. The emitter emits delayed fluorescence. Accordingly, when the emitter is used, an organic light-emitting device having high efficiency may be obtained. The proportion of delayed fluorescence components (DF portion) may be evaluated using a known method. A more detailed evaluation method of the DF portion will be described with reference to embodiments to be described later.
Each of the host and the sensitizer may not emit light.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
The host may not include metal atoms.
In an embodiment, the host may include one type of host. When the host includes one type of host, the one type of host may be an amphiprotic host, an electron transport host, or a hole transport host, which will be described later.
In one or more embodiments, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron transport host and a hole transport host, a mixture of two different types of electron transport hosts, or a mixture of two different types of hole transport hosts. The electron transport host and the hole transport host may be understood by referring to the related description to be presented later.
In one or more embodiments, the host may include an electron transport host including at least one electron transport moiety and a hole transport host that does not include an electron transport moiety.
The electron transport host may include at least one electron transport moiety. The hole transport host may not include an electron transport moiety.
In the present specification, the electron transport moiety may be a cyano group, —F, —CFH2, —CF2H, —CF3, a π-electron-deficient nitrogen-containing cyclic group, or a group represented by one of the following formulae:
In the formulae, *, *′, and *″ each indicate a binding site to a neighboring atom.
In an embodiment, the electron transport host may include a cyano group, a π-electron-deficient nitrogen-containing cyclic group, or any combination thereof.
In one or more embodiments, the electron transport host may include at least one cyano group.
In one or more embodiments, the electron transport host may include at least one cyano group and at least one π-electron-deficient nitrogen-containing cyclic group.
In an embodiment, the hole transport host may include at least one π-electron-deficient nitrogen-free cyclic group and may not include an electron transport moiety.
In the present specification, the term “π-electron-deficient nitrogen-containing cyclic group” refers to a cyclic group having at least one *—N═*′ moiety, and for example, 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 phthalazine group, a naphthyridine group, a quinoxaline 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, and an azacarbazole group; or a condensed cyclic group of two or more π-electron-deficient nitrogen-containing cyclic groups.
In the present specification, the term “π-electron-deficient nitrogen-free 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 corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene 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, or a triindolobenzene group; or a condensed cyclic group of two or more π-electron-deficient nitrogen-free cyclic groups, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the electron transport host may be a compound represented by Formula E-1 and the hole transport host may be a compound represented by Formula H-1, but embodiments of the present disclosure are not limited thereto:
[Ar301]xb11-[(L301)xb1-R301]xb21 Formula E-1
In Formula E-1,
Ar301 is a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 is 1, 2, or 3,
L301 is a single bond, a group represented by the following formulae, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group, and *, *′, and *″ in the following formulae are each a binding site to a neighboring atom,
xb1 is an integer from 1 to 5,
R301 is 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 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 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 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, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), —S(═O)(Q301), —P(═O)(Q301)(Q302), or —P(═S)(Q301)(Q302),
xb21 is an integer from 1 to 5,
Q301 to Q303 are each independently a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
at least one of the following Condition A to Condition C is satisfied.
Condition A
at least one of Ar301, L301, and R301 in Formula E-1 each independently includes a π-electron-deficient nitrogen-containing cyclic group;
Condition B
L301 in Formula E-1 is a group represented by one of the following formulae:
Condition C
R301 in Formula E-1 is a cyano group, —S(═O)2(Q301), —S(═O)(Q301), —P(═O)(Q301)(Q302), or —P(═S)(Q301)(Q302).
In Formulae H-1, 11, and 12,
L401 is: 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 corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene 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, and a triindolobenzene group, each unsubstituted or substituted with at least one deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, or —Si(Q401)(Q402)(Q403),
xd1 is an integer from 1 to 10, wherein, when xd1 is 2 or more, two or more of L401(s) may be identical to or different from each other,
Ar401 is groups represented by Formulae 11 or 12,
Ar402 is: a group represented by Formulae 11 or 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group; or
a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, each substituted with at least one deuterium, a hydroxyl 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, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or any combination thereof,
CY401 and CY402 are each independently a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, or a benzonaphthosilole group,
A21 is a single bond, O, S, N(R51), C(R51)(R52), or Si(R51)(R52),
A22 is a single bond, O, S, N(R53), C(R53)(R54), or Si(R53)(R54),
at least one of A21 and A22 in Formula 12 is not a single bond,
R51 to R54, R60, and R70 are each independently:
hydrogen, deuterium, a hydroxyl 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, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with at least one deuterium, a hydroxyl 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 phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;
a π-electron-deficient nitrogen-free cyclic group (for example, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group);
a π-electron-deficient nitrogen-free cyclic group (for example, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group) that is substituted with at least one deuterium, a hydroxyl 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, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, or any combination thereof; or
—Si(Q404)(Q405)(Q406),
e1 and e2 are each independently an integer from 0 to 10,
Q401 to Q406 are each independently hydrogen, deuterium, a hydroxyl 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 phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, and
* indicates a binding site to an adjacent atom.
In one or more embodiments, in Formula E-1, Ar301 and L301 may each independently be a benzene group, a naphthalene 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 pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene 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 phthalazine group, a naphthyridine group, a quinoxaline 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, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof;
at least one of L301(s) in the number of xb1 may each independently 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 phthalazine group, a naphthyridine group, a quinoxaline 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, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyhdinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group. —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof;
R301 may 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing tetraphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q31 to Q33 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, Ar301 may be: a benzene group, a naphthalene 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 pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenyl pyridinyl group, a diphenyl pyridinyl group, a biphenyl pyridinyl group, a di(biphenyl) pyridinyl group, a pyrazinyl group, a phenyl pyrazinyl group, a diphenyl pyrazinyl group, a biphenyl pyrazinyl group, a di(biphenyl) pyrazinyl group, a pyridazinyl group, a phenyl pyridazinyl group, a diphenyl pyridazinyl group, a biphenyl pyridazinyl group, a di(biphenyl) pyridazinyl group, a pyrimidinyl group, a phenyl pyrimidinyl group, a diphenyl pyrimidinyl group, a biphenyl pyrimidinyl group, a di(biphenyl) pyrimidinyl group, a triazinyl group, a phenyl triazinyl group, a diphenyl triazinyl group, a biphenyl triazinyl group, a di(biphenyl) triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof; or
A group represented by one of Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33, and
L301 may be a group represented by one of Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33:
In Formulae 5-1 to 5-3 and 6-1 to 6-33,
Z1 is 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
d4 is 0, 1, 2, 3, or 4,
d3 is 0, 1, 2, or 3,
d2 is 0, 1, or 2, and
* and *′ each indicate a binding site to a neighboring atom.
Q31 to Q33 are the same as described above.
In one or more embodiments, L301 may be a group represented by one of Formulae 5-2, 5-3, and 6-8 to 6-33.
In one or more embodiments, R301 may be a cyano group or a group represented by one of Formulae 7-1 to 7-18, and at least one of Ar402 in the number of xd11 may be a group represented by one of Formulae 7-1 to 7-18, but embodiments of the present disclosure are not limited thereto:
in Formulae 7-1 to 7-18,
xb41 to xb44 are each 0, 1, or 2, wherein xb41 in Formula 7-10 is not 0, the sum of xb41 and xb42 in Formulae 7-11 to 7-13 is not 0, the sum of xb41, xb42, and xb43 in Formulae 7-14 to 7-16 is not 0, the sum of xb41, xb42, xb43, and xb44 in Formulae 7-17 and 7-18 is not 0, and * indicates a binding site to a neighboring atom.
Two or more of Ar301(s) in Formula E-1 are identical to or different from each other, two or more of L301(s) in Formula E-1 are identical to or different from each other, two or more of L401(s) in Formula H-1 are identical to or different from each other, and two or more of Ar402(s) in Formula H-1 are identical to or different from each other.
The electron transport host may be, for example, a compound of a group HE1 to HE7, but embodiments of the present disclosure are not limited thereto:
In one embodiment, the hole transport host may be one of Compounds H-H1 to H-H103, but embodiments of the present disclosure are not limited thereto:
In one embodiment, the amphiprotic host may be one of Group HEH1, but embodiments of the present disclosure are not limited thereto:
In Compounds 1 to 432,
Ph may be a phenyl group.
When the host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host to the hole transport host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5:5. When the weight ratio of the electron transport host to the hole transport host satisfies the above-described ranges, the hole-and-electron transport balance in the emission layer 15 may be achieved.
The sensitizer may include a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof.
In an embodiment, the sensitizer may include iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), silver (Ag), copper (Cu), ruthenium (Ru), rhenium (Re), rhodium (Rh), terbium (Tb), thulium (Tm), or any combination thereof.
In an embodiment, the sensitizer may include Ir, Pt, or any combination thereof.
In an embodiment, the sensitizer may be an organometallic compound represented by Formula 2:
M21(L21)n21(L22)n22 Formula 2
In Formula 2,
M21 includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof,
L21 is a ligand represented by one of Formulae 2-1 to 2-4,
L22 is a monodentate ligand or a bidentate ligand,
n11 is 1, 2, or 3, and
n12 is 0, 1, 2, 3, or 4,
In Formulae 2-1 to 2-4,
A21 to A24 are each independently a C5-C30 carbocyclic group, a C1-C30 heterocyclic group, or a non-cyclic group,
T21 to T24 are each independently a single bond, a double bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R25)(R26)—*′, *—C(R25)═C(R26)—*′, *—C(R25)═*′, *—Si(R25)(R28)—*′, *—B(R25)—*′, *—N(R25)—*′, or *—P(R25)—*′,
k21 to k24 are each independently 1, 2, or 3,
Y21 to Y24 are each independently a single bond, *—O—*′, *—C(R27)(R28)—*′, *—Si(R27)(R28)—*′, *—B(R27)—*′, *—N(R27)—*′, or *—P(R27)—*′,
*1, *2, *3, and *4 each indicate a binding site to M21,
R21 to R28 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 heterocycloalkenyl group, a substituted or unsubstituted C8-C80 aryl group, a substituted or unsubstituted C7-C80 alkyl 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 C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), R21 to R28 are optionally bonded to each other to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, and
b21 to b24 are each independently an integer from 0 to 10.
In detail, the sensitizer may be of Groups S-I to S-VI, but embodiments of the present disclosure are not limited thereto:
A compound represented by the following Formula A:
(L101)n101-M101-(L102)m101. Formula A
In Formula A, L101, n101, M101, L102, and m101 are the same as shown in Tables 1 to 3:
In Table 1, AN1 to AN5 are as follows:
In Tables 1 to 3, LM1 to LM243 may be understood with reference to the following Formulae 1-1 to 1-3 and the following Tables 4 to 6:
X1 to X10 and Y1 to Y18 in Tables 4 to 6 are as follows, and Ph in the tables refers to a phenyl group:
An amount of the sensitizer in the emission layer may be from about 5 wt % to about 50 wt %. Within this range, it is possible to achieve effective energy transfer in the emission layer, and accordingly, an organic light-emitting device having high efficiency and long lifespan may be embodied.
Because the emitter emits fluorescence, for example, delayed fluorescence, an organic light-emitting device including the emitter emitting fluorescence is clearly distinguished from an organic light-emitting device including a compound emitting phosphorescence.
In an embodiment, a horizontal orientation ratio of the emitter may be greater than or equal to about 90%.
The horizontal orientation ratio of the emitter is a value obtained by using a quartz substrate, in which the host and the emitter are deposited at a weight ratio of (100−d):d to have a thickness of 50 nm, and comparing a graph obtained by measuring PL intensity according to an angle for a range of 0° to 90° with respect to the quartz substrate with a simulated graph having different horizontal orientation ratios, for example, a horizontal orientation ratio of 100% and a horizontal orientation ratio of 67%. Here, d is an arbitrary constant. In the quartz substrate, only the emitter may substantially emit light and may further satisfy T1(H)>S1(E).
A maximum emission wavelength of an emission spectrum of the emitter may be about 400 nm or more and about 550 nm or less. In an embodiment, a maximum emission wavelength of an emission spectrum of the emitter may be about 400 nm or more and about 495 nm or less, or about 450 nm or more and about 495 or less, but embodiments of the present disclosure are not limited thereto. That is, the emitter may emit blue light. The “maximum emission wavelength” refers to a wavelength at which the emission intensity is the greatest and may also be referred to as “a peak emission wavelength”.
In an embodiment, the emitter does not include metal atoms.
The emitter may be a condensed cyclic compound represented by Formula 1 below:
In Formula 1,
X11 is NR14 or O,
X12 is NR16 or O,
X13 is NR16 or O,
k11 is 0 or 1, wherein, when k11 is 0, (X11)k11 does not exist,
A11 to A13 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R11 to R16 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), wherein at least one of R11 to R13 is not hydrogen,
b11 to b13 are each independently an integer from 0 to 10, and
Q1 to Q3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof, or a C6-C60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
In an, embodiment, in Formula 1, k11 may be 0.
In an embodiment, in Formula 1, at least one of R11 to R13 is a C1-C60 alkyl group, —C(Q1)(Q2)(Q3), or —N(Q1)(Q2), and
Q1 to Q3 are each independently a C1-C60 alkyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof, or a C6-C60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
In an embodiment, in Formula 1, A11 to A13 may each independently be a group represented by Formula 10A, a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, or a perylene group, and
in Formula 10A,
X101 may be NR104 or O,
X102 may be NR105 or O,
X103 may be NR106 or O,
k101 may be 0 or 1, wherein, when k101 is 0, (X101)k101 may not exist,
A101 to A103 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, or a perylene group,
R101 to R106 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
b101 to b103 may each independently be an integer from 0 to 10, and
Q1 to Q3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof, or a C6-C60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
In an embodiment, in Formula 1, A11 and A13 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, or a perylene group, and A12 may be a group represented by Formula 10A, or
A11 to A13 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, or a perylene group.
In an embodiment, in Formulae 1 and 10A, k11 and k101 may be 0.
In detail, the emitter may be a condensed cyclic compound represented by Formula 1-1 or 1-2:
In Formulae 1-1 and 1-2,
X12 is NR15 or O,
X13 is NR16 or O,
X102 is NR105 or O,
X103 is NR106 or O,
R11 to R13, R15, R16, R102, R103, R105, and R106 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), wherein, at least one of R11 to R13 in Formula 1-1 is not hydrogen and at least one of R11 to R13, R102, and R103 in Formula 1-2 is not hydrogen,
b11 to b13, b102, and b103 are each independently an integer from 0 to 10, and
Q1 to Q3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, and a C6-C60 aryl group, or a C6-C60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, or a C6-C60 aryl group.
In an embodiment, the emitter may be a compound the following Group E-I: Group E-I
An amount of the sensitizer in the emission layer may be from about 5 wt % to about 50 wt %. Within these ranges, it is possible to achieve effective energy transfer in the emission layer, and accordingly, an organic light-emitting device having high efficiency and long lifespan may be obtained.
The hole transport region 12 may be located between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.
The hole transport region 12 may have a single-layered structure or a multi-layered structure.
For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer/hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer structure, a hole transport layer/interlayer structure, a hole injection layer/hole transport layer/interlayer structure, a hole transport layer/electron blocking layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, but embodiments of the present disclosure are not limited thereto.
The hole transport region 12 may include any compound having hole transport properties.
In an embodiment, the hole transport region 12 may include an amine-based compound.
In one embodiment, the hole transport region 12 may include at least one a compound represented by Formula 201 to a compound represented by Formula 205, but embodiments of the present disclosure are not limited thereto:
In Formulae 201 to 205,
L201 to L209 may each independently be *—O—*′, *—S—*′, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group,
xa1 to xa9 may each independently be an integer from 0 to 5, and
R201 to R206 may each independently be 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein neighboring two groups of R201 to R206 may optionally be bonded to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
In an embodiment,
L201 to L209 may be
a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene 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 corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene 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, and a triindolobenzene group, each unsubstituted or substituted with at least one deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, or —Si(Q11)(Q12)(Q13),
xa1 to xa9 are each independently 0, 1, or 2,
R201 to R206 are each independently a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, or a benzothienocarbazolyl group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or any combination thereof, and
Q11 to Q13 and Q31 to Q33 are each independently a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound.
In an embodiment, the hole transport region 12 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.
The carbazole-containing amine-based compound may be, for example, a compound represented by Formula 201 including a carbazole group and further including at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, or a benzothienocarbazole group.
The carbazole-free amine-based compound may be, for example, a compound represented by Formula 201 which do not include a carbazole group and which include at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.
In one or more embodiments, the hole transport region 12 may include at least one compound represented by Formulae 201 or 202.
In one embodiment, the hole transport region 12 may include at least one compound represented by Formulae 201-1, 202-1, and 201-2, but embodiments of the present disclosure are not limited thereto:
In Formulae 201-1, 202-1, and 201-2, L201 to L203, L205, xa1 to xa3, xa5, R201, and R202 are the same as described herein, and R211 to R213 are each independently 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 C1-C20 alkyl group, a C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, or a pyridinyl group.
In an embodiment, the hole transport region 12 may include at least one of Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the hole transport region 12 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (for example, at least one compound represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.
In one embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be about −3.5 eV or less.
The p-dopant may include at least one of a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
In an embodiment, the p-dopant may include at least one of:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ),2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), F6-TCNNQ, or any combination thereof;
In Formula 221,
R221 to R223 are each independently 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-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and at least one of R221 to R223 may have at least one of a cyano group, —F, —Cl, —Br, —I, a C1-C20 alkyl group substituted with —F, a C1-C20 alkyl group substituted with —Cl, a C1-C20 alkyl group substituted with —Br, a C1-C20 alkyl group substituted with —I, or any combination thereof.
The hole transport region 12 may have a thickness of about 100 Å to about 10,000 Å, for example, about 400 Å to about 2,000 Å, and the emission layer 15 may have a thickness of about 100 Å to about 3,000 Å, for example, about 300 Å to about 1,000 Å. When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges described above, satisfactory hole transportation characteristics and/or luminescence characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region 17 is located between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.
The electron transport region 17 may have a single-layered structure or a multi-layered structure.
For example, the electron transport region 17 may have an electron transport layer, an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, a hole blocking layer/electron transport layer structure, a buffer layer/electron transport layer/electron injection layer structure, or a hole blocking layer/electron transport layer/electron injection layer structure, but embodiments of the present disclosure are not limited thereto. The electron transport region 17 may further include an electron control layer.
The electron transport region 17 may include known electron transport materials.
The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one 7-electron-deficient nitrogen-containing cyclic group. The π-electron-deficient nitrogen-containing cyclic group is the same as described above.
In an embodiment, the electron transport region may include a compound represented by Formula 601 below.
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
In Formula 601,
Ar601 and L601 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xe11 is 1, 2, or 3,
xe1 is an integer from 0 to 5,
R601 is 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 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, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), or —P(═O)(Q601)(Q602),
Q601 to Q603 are each independently a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
xe21 is an integer from 1 to 5.
In one embodiment, at least one of Ar601(s) in the number of xe11 and R601(s) in the number of xe21 may include the π-electron-deficient nitrogen-containing cyclic group.
In an embodiment, in Formula 601, ring Ar601 and L601 may each independently be a benzene group, a naphthalene 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 pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole 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 pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline 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, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof,
wherein Q31 to Q33 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
When xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be bonded to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In one or more embodiments, a compound represented by Formula 601 may be represented by Formula 601-1 below:
In Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), and at least one of X614 to X616 may be N,
L611 to L613 may each independently be the same as described in connection with L601,
xe611 to xe613 may each independently be the same as described in connection with xe1,
R611 to R613 may each independently be the same as described in connection with R601, and
R614 to R616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In one or more embodiments, R601 and R611 to R613 in Formulae 601 and 601-1 are each independently: a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or any combination thereof;
—S(═O)2(Q601) or —P(═O)(Q601)(Q602),
wherein Q601 and Q602 are the same as described above.
The electron transport region may include at least one compound Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, the electron transport region may include at least one 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, or any combination thereof.
The thickness of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
The electron transport region 17 (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include at least one of alkali metal complex, alkaline earth-metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, or a metal ion of the alkaline earth-metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:
The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may be in direct contact with the second electrode 19.
The electron injection layer may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure having a plurality of layers consisting of a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may be Li, Na, K, Rb, or Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure are not limited thereto.
The alkaline earth metal may be Mg, Ca, Sr, or Ba.
The rare earth metal may be Sc, Y, Ce, Tb, Yb, or Gd.
The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be an oxide or a halide (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, or the rare earth metal.
The alkali metal compound may be an alkali metal oxide, such as Li2O, Cs2O, or K2O, or an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compound may be LiF, Li2O, NaF, LiI, NaI, CsI, or KI, but embodiments of the present disclosure are not limited thereto.
The alkaline earth-metal compound may be an alkaline earth-metal oxide, such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), or BaxCa1-xO (0<x<1). In one embodiment, the alkaline earth-metal compound may be BaO, SrO, or CaO, but embodiments of the present disclosure are not limited thereto.
The rare earth metal compound may be YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, or TbF3. In one embodiment, the rare earth metal compound may be YbF3, ScF3, TbF3, YbI3, ScI3, or TbI3, but embodiments of the present disclosure are not limited thereto.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of an alkali metal, an alkaline earth-metal, or a rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, or cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include the organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
The second electrode 19 is located on the organic layer 10A having such a structure. The second electrode 19 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
The second electrode 19 may include at least one of lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, IZO, or any combination thereof, but embodiments of the present disclosure are not limited thereto. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 19 may have a single-layered structure having a single layer or a multi-layered structure including two or more layers.
Hereinbefore, the organic light-emitting device has been described with reference to
The organic light-emitting device 100 of
The first emission unit 151 includes a first emission layer 151-EM, and the second emission unit 152 includes a second emission layer 152-EM. A maximum emission wavelength of light emitted from the first emission unit 151 may be different from a maximum emission wavelength of light emitted from the second emission unit 152. In an embodiment, the mixed light of the light emitted from the first emission unit 151 and the light emitted from the second emission unit 152 may be white light, but embodiments of the present disclosure are not limited thereto.
The hole transport region 120 is located between the first emission unit 151 and the first electrode 110, and the second emission unit 152 includes the first hole transport region 121 located on the side of the first electrode 110.
An electron transport region 170 is located between the second emission unit 152 and the second electrode 190, and the first emission unit 151 includes a first electron transport region 171 located between the charge generation layer 141 and the first emission layer 151-EM.
The first emission layer 151-EM is a thin film including a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and a horizontal orientation ratio of the thin film may be greater than or equal to about 80%.
The second emission layer 152-EM is a thin film including a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and a horizontal orientation ratio of the thin film may be greater than or equal to about 80%.
The first electrode 110 and the second electrode 190 illustrated in
The first emission layer 151-EM and the second emission layer 152-EM illustrated in
The hole transport region 120 and the first hole transport region 121 illustrated in
The electron transport region 170 and the first electron transport region 171 illustrated in
Hereinbefore, referring to
The organic light-emitting device 200 includes a first electrode 210, a second electrode 290 facing the first electrode 210, and a first emission layer 251 and a second emission layer 252 which are stacked between the first electrode 210 and the second electrode 290.
A maximum emission wavelength of light emitted from the first emission layer 251 may be different from a maximum emission wavelength of light emitted from the second emission layer 252. In an embodiment, the mixed light of the light emitted from the first emission layer 251 and the light emitted from the second emission layer 252 may be white light, but embodiments of the present disclosure are not limited thereto.
Meanwhile, a hole transport region 220 may be located between the first emission layer 251 and the first electrode 210, and an electron transport region 270 may be located between the second emission layer 252 and the second electrode 290.
The first emission layer 251 is a thin film including a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and a horizontal orientation ratio of the thin film may be greater than or equal to about 80%.
The second emission layer 252 is a thin film including a host, a sensitizer, and an emitter, the sensitizer includes a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, a sixth-row transition metal of the Periodic Table of Elements, a lanthanide metal, an actinide metal, or any combination thereof, and a horizontal orientation ratio of the thin film may be greater than or equal to 80%.
The first electrode 210, the hole transport region 220, and the second electrode 290 illustrated in
The first emission layer 251 and the second emission layer 252 illustrated in
The electron transport region 270 illustrated in
Hereinbefore, referring to
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
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 include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C2-C60 alkenyl group” as used herein has a structure including 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 has a structure including 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 monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent monocyclic group having at least one heteroatom of N, O, P, Si, B, Se, Te, Ge, or any combination thereof, as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl 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 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 heteroatom N, O, P, Si, B, Se, Te, Ge, or any combination thereof, as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group 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 term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocarbocyclic aromatic system that has at least one heteroatom of N, O, P, Si, B, Se, Te, Ge, or any combination thereof, as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom of N, O, P, Si, B, Se, Te, Ge, or any combination thereof, as a ring-forming atom, and 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 C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The term “C6-C60 aryloxy group” as used herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group” used herein refers to a monovalent group in which two or more rings are condensed with each other, only carbon is used as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60) and the whole molecule is a non-aromaticity group. 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 the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other, a heteroatom of N, O, P, Si, B, Se, Te, Ge, or any combination thereof, other than carbon atoms(for example, having 1 to 60 carbon atoms), as a ring-forming atom, and non-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 the monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.
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 of N, O, P, Si, B, Se, Te, Ge, or any combination thereof, other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.
In the present specification, a substituent is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(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 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;
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 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, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or any combination thereof; or
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), or —P(═O)(Q38)(Q39),
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one of a C1-C60 alkyl group and 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, or a monovalent non-aromatic condensed heteropolycyclic group.
The term “room temperature” used herein refers to a temperature of about 25° C.
The terms “a biphenyl group, a terphenyl group, and a tetraphenyl group” used herein respectively refer to monovalent groups in which two, three, or four phenyl groups which are linked together via a single bond.
The terms “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group” used herein respectively refer to a phenyl group, a biphenyl group, a terphenyl group, and a tetraphenyl group, each of which is substituted with at least one cyano group. In “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group”, a cyano group may be substituted to any position of the corresponding group, and the “cyano-containing phenyl group, the cyano-containing biphenyl group, the cyano-containing terphenyl group, and the cyano-containing tetraphenyl group” may further include substituents other than a cyano group. For example, a phenyl group substituted with a cyano group, and a phenyl group substituted with a cyano group and a methyl group may all belong to “a cyano-containing phenyl group.”
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples 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.
Compounds used in the Examples are as follows.
A host, a sensitizer, an emitter described in the following Table 7 were vacuum-deposited on a quartz substrate at a weight ratio shown in Table 7 at a vacuum pressure of 10−7 torr, to thereby manufacture samples having a thickness of 50 nm. With respect to the samples, Luxol-OLED/analyzer LOA-100 available from CoCoLink company was used to measure PL intensity for each angle in the range of 0° to 90°, an analyzer fitting program was used to determine horizontal orientation ratios obtained by assuming that a horizontal orientation ratio is 67% in a fully anisotropic case and a horizontal orientation ratio is 100% in a fully oriented case, and the horizontal orientation ratios are shown in the following Table 7. A host and a sensitizer described in the following Table 8 were vacuum-deposited on a quartz substrate at a weight ratio shown in Table 8 at a vacuum pressure of 10−7 torr, to thereby manufacture samples having a thickness of 50 nm. A horizontal orientation ratio was calculated in the same manner with respect to the samples, and results are shown in Table 8. Based on values shown in Tables 7 and 8, ⊖H+S+E/⊖H+S×100 was calculated, and results are shown in Table 9.
Referring to Table 9, it was confirmed that a horizontal orientation ratio of a sample including an emitter is improved, a rate of increase of each of the horizontal orientation ratios of Samples 1 to 13 are relatively high, and the ratio of the horizontal orientation ratios are at least 109% or more.
With respect to the sensitizer and the emitter used in Evaluation Example 1, SOI constant (J) was calculated from Equation 1, and results are shown in Table 10.
In Equation 1,
λ is an emission wavelength (nm),
FD(λ) is an emission spectrum of the sensitizer, and εA(λ) is an extinction coefficient spectrum of the emitter.
A glass substrate with a 50 nm-thick of ITO electrode pattern was ultrasonically cleaned in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposure of UV ozone thereto for 30 minutes.
Subsequently, N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine (DNTPD) was deposited to a thickness of 40 nm, N,N,N′N′-tetra[(1,10-biphenyl)-4-yl]-(1,10-biphenyl)-4,4′-diamine (BPBPA) was deposited to a thickness of 10 nm, and 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP) was deposited to a thickness of 10 nm, on the ITO electrode (anode) of the glass substrate in this stated order.
Next, a host, a sensitizer, and an emitter shown in Table 9 were co-deposited at a ratio described in Table 11 to thereby form an emission layer having a thickness of 50 nm.
On the emission layer, 2,8-bis(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzo[b,d]thiophene (DBFTrz) was deposited to a thickness of 5 nm, 9,10-di(naphthalene-2-yl)anthracen-2-yl-(4,1-phenylene)(1-phenyl-1Hbenzo[d]imidazole (ZADN) was deposited to a thickness of 20 nm, LiF was deposited to a thickness of 1.5 nm, and Al was deposited to a thickness of 200 nm, to thereby complete the manufacture of an organic light-emitting device having a structure of ITO (50 nm)/DNTPD (40 nm)/BPBPA (10 nm)/mCBP (10 nm)/emission layer (30 nm)/DBFTrz (5 nm)/ZADN (20 nm)/LiF (1.5 nm)/Al (200 nm).
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that a corresponding host, a corresponding sensitizer, and a corresponding emitter were used as shown in Table 11 in forming an emission layer.
With respect to each of the organic light-emitting devices manufactured in Examples 1 to 13, external quantum efficiency (EQE) and lifespan were evaluated and calculated as a relative value (%) and results thereof are shown in Table 11. A luminance meter (Minolta Cs-1000A) was used as an evaluation apparatus. Lifespan (T95) was determined by evaluating the time that is taken for luminance to become 95% compared to the initial luminance of 100%, under the same luminance measurement conditions.
From Table 11, it was confirmed that the organic light-emitting devices of Examples 1 to 13 have improved efficiency and improved lifespan compared to the organic light-emitting device of Comparative Example 1.
A correlation between a change in a horizontal orientation ratio and external quantum efficiency, according to an absence/presence of emitter, is illustrated in
From
The organic light-emitting device may have improved efficiency and/or improved lifespan.
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 |
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10-2020-0121785 | Sep 2020 | KR | national |