Patent Application
20230363272
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application Nos. 10-2022-0055746, filed on May 4, 2022, and 10-2023-0057346, filed on May 2, 2023, in the Korean Intellectual Property Office, the content of which are herein incorporated by reference in their entirety.
The disclosure relates to a light-emitting device and an electronic apparatus including the same.
Organic light-emitting devices are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is arranged between the anode and the cathode and includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged 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 may recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thereby generating light.
The need remains for novel materials for organic light-emitting devices.
Provided are a light-emitting device using a novel host combination and an electronic apparatus including the light-emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect of the disclosure, a light-emitting device includes a first electrode, a second electrode, and an interlayer arranged between the first electrode and the second electrode and including an emission layer,
wherein the emission layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2:
The emission layer may include, in addition to the first compound and the second compound, a third compound, a fourth compound, or any combination thereof. In this regard, the first compound and the second compound may each act as a host, and the third compound and the fourth compound may each act as a dopant.
According to another aspect of the disclosure, an electronic apparatus includes the light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the FIGURE which is a schematic cross-sectional view of a light-emitting device according to an exemplary embodiment.
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 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. 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.
An aspect of the disclosure provides a light-emitting device including: a first electrode; a second electrode; and an interlayer arranged between the first electrode and the second electrode and including an emission layer, wherein the emission layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2.
In Formula 1, CY11 and CY12 may each independently be a C5-C30 carbocyclic group.
For example, CY11 and CY12 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, or a fluorene group.
In Formula 1, CY13 and CY14 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY13 and CY14 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, CY11 and CY12 may each independently be a benzene group or a naphthalene group, and CY13 and CY14 may each independently be a benzene group, a naphthalene group, or a pyridine group.
In Formula 1, Y11 may be O, S, or Se.
In Formula 1, T13 and T14 may each independently be a group represented by Formula 1A:
Details of Formula 1 may be as described herein.
In Formula 1, a13 and a14 may each independently be an integer from 1 to 10.
In an embodiment, the sum of a13 and a14 may be 1 or more.
For example, the sum of a3 and a4 may be 1 or 2.
In Formula 1, R11 and R12 may each independently be hydrogen, deuterium, —F, —C1, —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 substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C1 heterocycloalkenyl 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 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, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, R11 and R12 may each independently be:
In an embodiment, R11 and R12 may each independently be:
In Formulae 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-11, 10-211 to 10-304, 10-315 to 10-345, and 10-347 to 10-354, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, “TMG” represents a trimethylgermyl group, and “t-Bu” represents a t-butyl group.
In Formula 1, R13 and R14 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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 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, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, R13 and R14 may each independently be:
In an embodiment, R13 and R14 may each independently be:
In Formulae 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-354, indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, “TMG” represents a trimethylgermyl group, and “t-Bu” represents a t-butyl group.
In Formula 1, b11 to b14 may each independently be an integer from 1 to 10.
In Formula 1A, CY15 and CY16 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY15 and CY16 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, CY15 and CY16 may each independently be a benzene group, a naphthalene group, or a pyridine group.
In Formula 1A, * indicates a binding site to a neighboring atom.
In Formula 1A, R15 and R16 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C1 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 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, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, R15 and R16 may each independently be:
In an embodiment, R5 and R6 may each independently be:
In Formula 1A, b15 and b16 may each independently be an integer from 1 to 10.
In an embodiment, Formula 1 may be represented by one of Formulae 1(1)-1 to 1(1)-4:
In Formulae 1(1)-1 to 1(1)-4, CY11, CY13, CY14, Y11, T13, T14, a13, a14, R11 to R14, b11, b13, and b14 may each be as defined herein, and d12 may be an integer from 1 to 3.
In an embodiment, a moiety represented by
in Formula 1 may be a group represented by one of Formulae 1(2)-1 to 1(2)-4:
In Formulae 1(2)-1 to 1(2)-4,
In an embodiment, Formula 1A may be a group represented by one of Formulae 1A-1 to 1A-5:
In Formulae 1A-1 to 1A-5,
In an embodiment, in Formula 1, at least one of R11 in the number of b1, R12 in the number of b12, R13 in the number of b13, R14 in the number of b14, R1 in the number of b R1, and R18 in the number of b16 may be deuterium.
For example, R11 in the number of b11 and R12 in the number of b12 may each be deuterium, R13 in the number of b13 and R4 in the number of b14 may each be deuterium, or R15 in the number of b15 and R16 in the number of b16 may each be deuterium.
For example, R11 in the number of b11, R12 in the number of b12, R13 in the number of b13, and R14 in the number of b14 may each be deuterium, or R11 in the number of b11, R12 in the number of b12, R13 in the number of b13, R14 in the number of b14, R1 in the number of b15, and R16 in the number of b16 may each be deuterium.
In an embodiment, the first compound may be represented by one of Formulae 1-1 to 1-16:
In Formulae 1-1 to 1-16,
In an embodiment, in Formulae 1-1 to 1-16, at least one of R11 in the number of b11, R12 in the number of d12, R13 in the number of b13, R14 in the number of d14, R15 in the number of b15, and R16 in the number of b16 may be deuterium.
In an embodiment, the first compound may be a compound selected from Compounds H1 to H32 in which at least one hydrogen atom is substituted with a deuterium atom:
In the “compound selected from Compounds H1 to H32 in which at least one hydrogen atom is substituted with a deuterium atom” as used herein, 1 to 22 hydrogen atoms may be substituted with deuterium atoms.
“Compound Hx(y)” as used herein refers to Compound Hx in which hydrogen atoms in the number of y are substituted with deuterium atoms. For example, “Compound H9(22)” as used herein refers to Compound H9 in which 22 hydrogen atoms are substituted with deuterium atoms.
In Formula 2, CY23 and CY24 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY23 and CY24 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, CY23 and CY24 may each independently be a benzene group, a naphthalene group, or a pyridine group.
In Formula 2, X21 may be N or C(R21a), X22 may be N or C(R22a), and X23 may be N or C(R23a).
In an embodiment, at least one of X21 to X23 may be N.
For example, one of X21 to X23 may be N, two of X21 to X23 may each be N, or X21 to X23 may each be N.
In Formula 2, L21 and L22 may each independently be a single bond, a substituted or unsubstituted C3-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group.
For example, L21 and L22 may each independently be:
In an embodiment, L21 and L22 may each independently be a single bond; or a benzene group, a naphthalene group, a pyridine group, or a carbazole group, each unsubstituted or substituted with at least one R10a.
In an embodiment, L21 and L22 may each independently be a single bond; or a group represented by one of Formulae L-1 to L-12
In Formulae L-1 to L-12,
In an embodiment, in Formulae L-1 to L-12, Z1 to Z4 may each independently be a phenyl group, a naphthyl group, a biphenyl group, —SiPh3, or a carbazolyl group, each unsubstituted or substituted with deuterium.
In Formula 2, n21 and n22 may each independently be an integer from 1 to 5.
In Formula 2, R21 to R24, R21a, R22a, and R23a may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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 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, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
For example, R21 to R24, R21a, R22a, and R23a may each independently be: hydrogen, 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, —SF5, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
In an embodiment, R21 to R24, R21a, R22a, and R23a may each independently be:
In Formulae 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-354, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, “TMG” represents a trimethylgermyl group, and “t-Bu” represents a t-butyl group.
In an embodiment, R21 and R22 may each independently be:
In an embodiment, R21 and R22 may each independently be a C6-C60 aryl group unsubstituted or substituted with at least one R10a, a group represented by Formula 2A, or a group represented by Formula 2B, wherein R10a may be defined as in connection with R23:
In Formulae 2A and 2B,
In Formula 2, b21 to b24 may each independently be an integer from 1 to 10.
In an embodiment, the second compound may be one of Compounds E1 to E39:
In the light-emitting device according to the disclosure, the emission layer includes the first compound represented by Formula 1 and the second compound represented by Formula 2. By including the first compound and the second compound at the same time, the light-emitting device may have improved lifespan characteristics.
In one or more embodiments, the emission layer in the light-emitting device may further include, in addition to the first compound and the second compound, a third compound, a fourth compound, or any combination thereof.
For example, the emission layer may include i) the first compound, the second compound, and the third compound, ii) the first compound, the second compound, and the fourth compound, or iii) the first compound, the second compound, the third compound, and the fourth compound.
Hereinafter, the third compound and the fourth compound will be described.
The third compound may include a transition metal.
In an embodiment, the third compound may be a phosphorescent dopant. For example, the third compound may be a blue phosphorescence-emitting dopant. For example, the third compound may be a blue platinum dopant.
In one or more embodiments, the third compound (for example, the phosphorescent dopant) may be a sensitizer compound that may be used with the fourth compound to be described below, for example, a fluorescent dopant represented by Formula 4, to transfer excitons to a fluorescent dopant.
In an embodiment, the third compound may include a transition metal and a tetradentate ligand. In one or more embodiments, the third compound may include a transition metal and at least one monodentate ligand, bidentate ligand, or tridentate ligand.
In an embodiment, the third compound may include an organometallic compound represented by Formula 3:
In Formula 3, M31 may be a transition metal.
In an embodiment, M31 may be Pt, Pd, or Au.
In Formula 3, X31 to X34 may each independently be C or N, and two bonds of a bond between X31 and M31, a bond between X32 and M31, a bond between X33 and M31, and a bond between X34 and M31 may each be a coordinate bond, and the other two bonds may each be a covalent bond.
In an embodiment, a bond between X31 and M31 may be a coordinate bond.
In an embodiment, X31 may be C, and a bond between X31 and M31 may be a coordinate bond. That is, in Formula 3, X31 may be C in a carbene moiety.
In Formula 3, CY31 to CY34 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In an embodiment, CY31 to CY34 may each independently be:
In Formula 3, L31 may be a single bond, a double bond, *—N(R35a)—*′, *—B(R35a)—*′, *—P(R35a)—*′, *—C(R35a)(R35b)—*′, *—Si(R35a)(R35b)—*′, *—Ge(R35a)(R35b)—*′, *—S—*′, *—Se—*,*—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R35a)═*′, *═C(R35a)—*′, *—C(R35a)═C(R35b)—*′, *—C(═S)—*′, *—C≡C—*′, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
In Formula 3, n31 to n34 may each independently be an integer from 0 to 5, wherein three or more of n31 to n34 may each independently be an integer from 1 to 5.
In Formula 3, when n31 is 0, L31 may not be present, when n32 is 0, L32 may not be present, when n33 is 0, L33 may not be present, and when n34 is 0, L34 may not be present.
In Formula 3, when n31 is 2 or more, two or more of L31 may be identical to or different from each other, when n32 is 2 or more, two or more of L32 may be identical to or different from each other, when n33 is 2 or more, two or more of L33 may be identical to or different from each other, and when n34 is 2 or more, two or more of L34 may be identical to or different from each other.
In Formula 3, R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 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 C2-C1 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 arylalkyl 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 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9).
In an embodiment, R31 to R34, R35a, R35b, R36a, R35b, R37a, R37b, R38a, and R38b may each independently be:
In an embodiment, the third compound may include an organometallic compound represented by Formula 3-1 or Formula 3-2:
In Formula 3, b31 to b34 may each independently be an integer from 0 to 203.
In Formula 3, two or more of R31 in the number of b31 may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
Two or more of R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, and
In Formulae 3-1 and 3-2,
In an embodiment, in Formulae 3-1 and 3-2, R311 to R317 may each independently be:
For example, in Formulae 3-1 and 3-2, at least one of R311 to R317 may include a C1-C20 alkyl group, a C6-C60 aryl group, or a C7-C60 arylalkyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a cumyl group, or a combination thereof.
In one or more embodiments, the third compound may include an organometallic compound represented by Formula 5:
M51(L51)n51(L52)n52. Formula 5
In Formula 5, M51 may be a transition metal.
For example, M51 may be a first-row transition metal, a second-row transition metal, or a third-row transition metal of the Periodic Table of Elements.
In one or more embodiments, M51 may be iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In an embodiment, M51 may be Ir, Pt, Os, or Rh.
In Formula 5, L51 may be a ligand represented by Formula 5A, and L52 may be a ligand represented by Formula 5B:
Details of Formulae 5A and 5B may be as described herein.
In Formula 5, n51 may be 1, 2, or 3, wherein, when n51 is 2 or more, two or more of L51 may be identical to or different from each other.
In Formula 5, n52 may be 0, 1, or 2, wherein, when n52 is 2, two of L52 may be identical to or different from each other.
In Formula 5, the sum of n51 and n52 may be 2 or 3. For example, the sum of n51 and n52 may be 3.
In an embodiment, in Formula 5, i) M51 may be Ir, and the sum of n51 and n52 may be 3; or ii) M51 may be Pt, and the sum of n51 and n52 may be 2.
In one or more embodiments, in Formula 5, M51 may be Ir, and i) n51 may be 1, and n52 may be 2, or ii) n51 may be 2, and n52 may be 1.
In Formula 5, L51 and L52 may be different from each other.
In Formulae 5A and 5B, Y51 to Y54 may each independently be C or N. For example, Y51 and Y53 may each be N, and Y52 and Y54 may each be C.
In Formulae 5A and 5B, CY51 to CY54 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY51 to CY54 may each independently include i) a third ring, ii) a fourth ring, iii) a condensed cyclic group in which two or more third rings are condensed with each other, iv) a condensed cyclic group in which two or more fourth rings are condensed with each other, or v) a condensed cyclic group in which at least one third ring is condensed with at least one fourth ring,
In one or more embodiments, in Formulae 5A and 5B, ring CY51 to ring CY54 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinooxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinooxadiazole group, a pyridinothiadiazole group, a pyrimidinopyrrole group, a pyrimidinopyrazole group, a pyrimidinoimidazole group, a pyrimidinooxazole group, a pyrimidinoisoxazole group, a pyrimidinothiazole group, a pyrimidinoisothiazole group, a pyrimidinooxadiazole group, a pyrimidinothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, a benzene group condensed with a norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.
In an embodiment, CY51 and CY53 may be different from each other.
In one or more embodiments, CY25 and CY54 may be different from each other.
In one or more embodiments, CY51 to CY54 may be different from one another.
In Formulae 5A and 5B, R51 to R54 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 may each be as defined herein.
In an embodiment, in Formulae 5A and 5B, R51 to R54 may each independently be:
In one or more embodiments, R51 to R54 may each independently be:
In Formulae 5A and 5B, b51 to b54 indicate the number of R51 to the number of R54, respectively, and may each independently be an integer from 0 to 20. When b51 is 2 or more, two or more of R51 may be identical to or different from each other, when b52 is 2 or more, two or more of R52 may be identical to or different from each other, when b53 is 2 or more, two or more of R53 may be identical to or different from each other, and when b54 is 2 or more, two or more of R54 may be identical to or different from each other. For example, b51 to b54 may each independently be an integer from 0 to 8.
In an embodiment, the third compound may be one of Compounds P1 to P52:
When the third compound is selected from Compounds P1 to P52, formation of exciplexes with host compounds, such as the first compound and the second compound, that of a host compound by including a bulky substituent (for example, a tert-butyl group, a cumyl group, etc.), thereby facilitating formation of an exciplex. In the case of the third compound, a gap between a lowest unoccupied molecular orbital (LUMO) level of an electron transporting (ET) host and a highest occupied molecular orbital (HOMO) level of the third compound may be reduced, thereby facilitating formation of an exciplex.
A difference between a triplet energy level and a singlet energy level of the fourth compound may be equal to or less than 0.4 eV.
In an embodiment, the fourth compound may be a fluorescent dopant. For example, the fluorescent dopant may be a thermally activated delayed fluorescence dopant and a blue dopant.
In an embodiment, the fourth compound (for example, the fluorescent dopant) may be a luminescence emitter that may emit light by receiving excitons from an exciplex of a host and a phosphorescent dopant according to embodiments so that the received excitons transition to a ground state.
In an embodiment, the fluorescent dopant may be a compound represented by Formula 4:
In Formula 4,
In an embodiment, R41 to R49 may each independently be:
In an embodiment, Formula 4 may be selected from Formulae 4-1 to 4-8:
In Formulae 4-1 to 4-9,
In an embodiment, the fourth compound may be selected from Compounds D1 to D30:
In an embodiment, an amount of the fourth compound included in the emission layer may be in a range of 0 weight percent (wt %) to about 5 wt %.
In an embodiment, the emission layer of the light-emitting device may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 400 nanometers (nm) to about 490 nm.
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode. In one or more embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, an auxiliary layer, or any combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
The FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to an exemplary embodiment. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to an embodiment will be described with reference to the FIGURE. The organic light-emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in this stated order.
A substrate may be additionally arranged under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 11 may be, for example, formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (“ITO”), indium zinc oxide (“IZO”), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.
The organic layer 15 may be arranged on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be arranged between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in a range of about 100° C. to about 500° C., a vacuum pressure in a range of about 108 torr to about 103 torr, and a deposition rate in a range of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec, but embodiments are not limited thereto.
When the hole injection layer is formed by spin coating, the coating conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature for removing a solvent after coating in a range of about 80° C. to about 200° C., but embodiments are not limited thereto.
Conditions for forming the hole transport layer and the electron blocking layer may be the same as the conditions for forming the hole injection layer.
The hole transport region may include, for example, at least one of “m-MTDATA,” “TDATA,” “2-TNATA,” “NPB”, “β-NPB,” “TPD,” “Spiro-TPD,” “Spiro-NPB,” methylated NPB, “TAPC,” “HMTPD,” 4,4′,4″-tris(N-carbazolyl)triphenylamine (“TCTA”), polyaniline/dodecylbenzenesulfonic acid (“PANI”/“DBSA”), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (“PEDOT”/“PSS”), polyaniline/camphor sulfonic acid (“PANI”/“CSA”), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In Formula 201, Ar101 and Ar102 may each independently be:
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but embodiments are not limited thereto.
In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be:
In Formula 201, R109 may be:
In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:
In Formula 201A, R101, R111, R112, and R109 may each be as defined herein.
For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT20, but embodiments are not limited thereto:
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the ranges described above, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to the materials described above, a charge-generation material for improving conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (“TCNQ”), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (“F4-TCNQ”), and “F6-TCNQ;” a metal oxide, such as a tungsten oxide and a molybdenum oxide; and a cyano group-containing compound, such as Compounds HT-D1 and F12, but embodiments are not limited thereto:
The hole transport region may further include a buffer layer.
The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.
The emission layer may be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and LB deposition. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, though the deposition or coating conditions may vary according to a material that is used.
When the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be selected from materials for the hole transport region described above and host materials to be described below, but embodiments are not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be mCP, which will be described below.
In an embodiment, the emission layer may include a host and a dopant.
For example, the host may include the first compound and the second compound described above.
For example, the dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof, wherein the phosphorescent dopant may include the third compound described above, and the fluorescent dopant may include the fourth compound described above.
An amount of the dopant in the emission layer may be in a range of about 0.1 parts by weight to about 20 parts by weight based on 100 parts by weight of the emission layer.
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light, and various modifications are possible.
Next, the electron transport region may be arranged on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but embodiments are not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be the same as the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but embodiments are not limited thereto:
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within the ranges described above, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include at least one of BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:
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 ranges described above, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include, in addition to the materials described above, a metal-containing material.
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 may include an electron injection layer that facilitates electron injection from the second electrode 19.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be arranged on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which has a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device 10 has been described with reference to the FIGURE, but embodiments are not limited thereto.
Another aspect of the disclosure provides a diagnostic composition including at least one of the organometallic compounds represented by Formula 3 or 5.
Since the organometallic compound represented by Formula 3 or 5 provides high luminescence efficiency, the diagnostic composition including the organometallic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications, such as a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
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 are 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, a hexyl group, and the like. 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” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof are a methoxy group, an ethoxy group, an isopropoxy group, and the like.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are an ethenyl group, a propenyl group, a butenyl group, and the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are an ethynyl group, a propynyl group, and the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. 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 selected from N, O, P, Si, Ti, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof are a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. 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 are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, Ti, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in the ring thereof. Examples of the C2-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. The term “C2-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C2-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 are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other. The term “C7-C60 alkylaryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C30 heteroaryl group” as used herein refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, Ti, B, Se, Te, Ge, S, 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 selected from N, O, P, Ti, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the rings may be fused to each other. The term “C2-C60 alkylheteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein 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 “C1-C60 heteroaryloxy group” as used herein refers to —OA104 (wherein A104 is the C1-C60 heteroaryl group), and the term “C1-C30 heteroarylthio group” as used herein refers to —SA105 (wherein A105 is the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are a fluorenyl group and the like. 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 (for example, having 2 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are a carbazolyl group and the like. 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 5 to 30 carbon atoms only as ring-forming atoms. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
The term “C1-C60 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, Ti, B, Se, Te, Ge, S, or any combination thereof as ring-forming atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
In an embodiment, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group, 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, or a C2-C10 heterocycloalkenyl group, each unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C3-C10 cycloalkyl group, a C6-C60 aryl group, or any combination thereof; or a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
Hereinafter, a compound and an organic light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples, but the disclosure 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.
3 grams (g) of 2-bromodibenzo[b,d]furan-1,3,4,6,7,8,9-d7, 2.1 g of 9H-3,9′-bicarbazole, 0.27 g of Pd2(dba)3, and 0.85 g of sodium tert-butoxide were added to 30 milliliters (ml) of toluene. The mixture was stirred after 0.4 ml of a P(tBu)3 50% solution was added thereto, and then heated under reflux. After 6 hours, the resulting solution was filtered through a silica pad and then purified by column chromatography to obtain Compound H9(22) (2.5 g, 4.8 mmol), in which 22 deuterium atoms are substituted.
LC-Mass [M]+: 520.3 g/mol.
Compound E1 was synthesized according to the following reaction scheme.
9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (9.56 g, 21.45 mmol), triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (10.91 g, 23.59 mmol), Pd(PPh3)4 (2.48 g, 2.14 mmol), and K2CO3 (5.93 g, 42.90 mmol) were dissolved in tetrahydrofuran/distilled water (54 ml/22 ml). The mixture was heated and then stirred under reflux for 12 hours. After completion of the reaction, the temperature was lowered to room temperature, and then methanol (1,000 mL) was added thereto. The resulting solid was filtered and then purified by silica column chromatography to obtain 8.50 g (yield of 53%) of Compound E1.
LC-Mass (calculated: 745.27 g/mol, found: M+1=746 g/mol).
Compound D3 was synthesized in the same manner as in the method disclosed in WO2021-014001.
9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS 38537-24-5, 2 equivalents “eq”) was reacted with n-BuLi (2 eq) at room temperature. After 15 minutes, cyanuric chloride (1 eq) was slowly added dropwise and reacted overnight at 70° C. to obtain Intermediate E34-1. Intermediate E34-1 was confirmed by LC-MS.
LC-Mass (calculated: 461.21 g/mol, found: M+1=462.33 g/mol).
1,3-dibromobenzene-2,4,5,6-d4 (CAS 1616983-07-3, 1 eq) was reacted with n-BuLi (1.1 eq) at −78° C. After 60 minutes, chlorotris(phenyl-d5)silane (CAS 59620-15-4, 1.2 eq) was slowly added dropwise, and the temperature was slowly raised to room temperature and reacted overnight to obtain Intermediate E34-2. Intermediate E34-2 was confirmed by LC-MS.
LC-Mass (calculated: 433.16 g/mol, found: M+1=434.21 g/mol).
Intermediate E34-2 was reacted with n-BuLi under the condition of −78° C. After 60 minutes, trimethylborate was slowly added dropwise, and then the temperature was slowly raised to room temperature and reacted overnight to obtain Intermediate E34-3. Intermediate E34-3 was confirmed by LC-MS.
LC-Mass (calculated: 399.26 g/mol, found: M+1=400.10 g/mol).
3.1 g of Intermediate E34-1, 3.2 g of Intermediate E34-3, 0.31 g of tetrakis(triphenylphosphine)palladium, and 2.3 g of potassium carbonate were put into a reaction vessel and dissolved in 40 mL of toluene, 10 mL of ethanol, and 10 mL of distilled water. The mixture was heated and then stirred under reflux for 24 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate, the collected organic layer was dried with magnesium sulfate, and the solvent was evaporated. The residue obtained by evaporation was separated by silica gel column chromatography and purified to obtain 3.4 g (yield: 64%) of Compound E34. Compound E34 was confirmed by LC-MS.
LC-Mass (calculated: 780.49 g/mol, found: M+1=781.51 g/mol).
A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) electrode (first electrode, anode) formed thereon was cleaned by ultrasonication using distilled water. After the completion of ultrasonication using distilled water, ultrasonic cleaning was performed on the substrate using solvents, such as isopropyl alcohol, acetone, and methanol. Then, the substrate was dried, transferred to a plasma cleaner, cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum depositor.
Compound HT3 and Compound HT-D2 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 100 Å, Compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å, and mCP was deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å, thereby forming a hole transport region.
A combination of host compounds and a dopant compound shown in Table 1 (Example 1-1) or a combination of host compounds and dopant compounds shown in Table 2 (Example 2-1) was co-deposited on the hole transport region to form an emission layer having a thickness of 400 Å.
BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, Compound ET3 and LiQ were co-vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and an Al second electrode (cathode) having a thickness of 1,200 Å was formed on the electron injection layer, thereby completing the manufacture of a light-emitting device.
Light-emitting devices were manufactured in the same manner as in Example 1-1, except that compounds shown in Table 1 were each used in forming the emission layer. Example 2-2 and Comparative Examples 2-1 to 2-4
Light-emitting devices were manufactured in the same manner as in Example 2-1, except that compounds shown in Table 2 were each used in forming the emission layer. Evaluation Example 1: Evaluation of characteristics of light-emitting devices
The lifespan (LT95) of the light-emitting devices according to Examples and Comparative Examples was measured, and the results are shown in Tables 1 and 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A) were used as apparatuses for evaluation, and the lifespan (LT95) (at 1,000 nit) was obtained by measuring the amount of time that elapsed until luminance was reduced to 95% of the initial luminance of 100%, and the results are expressed as relative values.
In Table 1, the weight ratio of the host compound to the dopant compound is 87:13, and the weight ratio of the first compound to the second compound in the host compound is 57:30.
In Table 2, the weight ratio of the host compound to the dopant compound is 86.2:13.8, the weight ratio of the first compound to the second compound in the host compound is 56:30.2, and the weight ratio of the third compound to the fourth compound in the dopant compound is 13:0.8.
From Table 1, it was confirmed that the light-emitting device of Examples 1-1 and 1-2 had long lifespan characteristics, as compared with the light-emitting devices of Comparative Examples 1-1 to 1-4.
From Table 2, it was confirmed that the light-emitting device of Examples 2-1 and 2-2 had long lifespan characteristics, as compared with the light-emitting devices of Comparative Examples 2-1 to 2-4.
As described above, a light-emitting device using the first compound and the second compound in an emission layer may have long lifespan characteristics. Accordingly, a high-quality electronic apparatus may be implemented by using the light-emitting device.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0055746 | May 2022 | KR | national |
| 10-2023-0057346 | May 2023 | KR | national |
