Patent Application
20230276693
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2022-0025500, filed on Feb. 25, 2022, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
The present disclosure relates to a light-emitting device, an electronic apparatus including the light-emitting device, and a mixture (also referred to as “a composition”).
From among light-emitting devices, organic light-emitting devices are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, luminance, driving voltage, and response speed, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an interlayer arranged between the anode and the cathode, wherein the interlayer 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 recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.
Provided are a light-emitting device having excellent luminescence efficiency and lifespan characteristics at the same time and an apparatus including the light-emitting device. In addition, provided is a mixture that may be used in manufacturing 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 an embodiment, a light-emitting device includes:
M(L1)n1(L2)n2 Formula 1
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an 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 C2-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), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
According to an aspect of another embodiment, an electronic apparatus includes the light-emitting device.
According to an aspect of another embodiment, a mixture includes:
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 FIGURE which shows a schematic cross-sectional view of a light-emitting device according to an 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 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.
A light-emitting device according to an embodiment of the present disclosure may include: a first electrode; a second electrode; and an interlayer arranged between the first electrode and the second electrode and including an emission layer.
The interlayer may include a first compound represented by Formula 1, a second compound that is free of an electron-transporting group, and a third compound represented by Formula 7. In this regard, the second compound may not include an indolocarbazole group. In addition, the second compound and the third compound may be different from each other.
M in Formula 1 may be a transition metal.
For example, M may be a Period 1 transition metal, a Period 2 transition metal, or a Period 3 transition metal.
In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In an embodiment, M may be Ir, Pt, Os, or Rh.
L1 in Formula 1 may be a ligand represented by Formula 2A, and n1 in Formula 1 indicates the number of L1(s) in Formula 1 and may be 1 or 2. When n1 is 2, two of L1(s) may be identical to or different from each other.
L2 in Formula 1 may be a ligand represented by Formula 2B, and n2 in Formula 1 indicates the number of L2(s) in Formula 1 and may be 1 or 2. When n2 is 2, two of L2(s) may be identical to or different from each other.
Formulae 2A and 2B will be described in detail later.
The sum of n1 and n2 in Formula 1 may be 2 or 3.
L1 and L2 in Formula 1 may be different from each other. That is, the first compound represented by Formula 1 may be a heteroleptic complex.
In an embodiment, M may be Ir, and the sum of n1 and n2 may be 3; or M may be Pt, and the sum of n1 and n2 may be 2.
In one or more embodiments, M may be Ir, and i) n1 may be 1 and n2 may be 2; or ii) n1 may be 2 and n2 may be 1.
Y4 in Formula 2B may be C or N.
For example, Y4 in Formula 2B may be C.
X1 in Formula 2B may be Si or Ge.
In an embodiment, X1 in Formula 2B may be Si.
In one or more embodiments, in Formula 2B, X1 may be Si, and R12 may not be hydrogen, or R12 may not be hydrogen or a methyl group.
In one or more embodiments, in Formula 2B, X1 may be Si, and R12 may be —CD3, —CD2H, or —CDH2.
In one or more embodiments, in Formula 2B, X1 may be Si, and the number of carbon atoms included in R12 may be 2 or more.
In one or more embodiments, X1 in Formula 2B may be Ge.
In one or more embodiments, in Formula 2B, X1 may be Ge, and R12 may not be hydrogen, or R12 may not be hydrogen or a methyl group.
In one or more embodiments, in Formula 2B, X1 may be Ge, and R12 may be —CD3, —CD2H, or —CDH2.
In one or more embodiments, in Formula 2B, X1 may be Ge, and the number of carbon atoms included in R12 may be 2 or more.
X21 in Formula 2A may be O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30). Z29 and Z30 are respectively the same as those described herein.
For example, X21 in Formula 2A may be O or S.
In Formula 2A, T1 to T4 may each independently be C, N, a carbon atom bonded to ring CY1, or a carbon atom bonded to M in Formula 1, one of T1 to T4 may be a carbon atom bonded to M in Formula 1, one of the remaining T1 to T4 that are not bonded to M may be a carbon atom bonded to ring CY1, and T5 to T8 may each independently be C or N.
In an embodiment, the number of N(s) among T1 to T8 in Formula 2A may be 0, 1, 2, or 3.
In one or more embodiments, the number of N(s) among T1 to T8 in Formula 2A may be 0.
In one or more embodiments, Ta in Formula 2A may be N.
Ring CY1 and ring CY14 in Formulae 2A and 2B may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, Ar2 in Formula 2A may be ring CY2 unsubstituted or substituted with at least one Z0, and ring CY2 may be an unsaturated C5-C30 carbocyclic group or an unsaturated C1-C30 heterocyclic group. Z0 is the same as Z0 described herein.
In an embodiment, ring CY1 and ring CY14 in Formulae 2A and 2B may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a silole group, a germole group, a selenophene 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, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In one or more embodiments, ring CY1 and ring CY14 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.
In one or more embodiments, ring CY1 in Formula 2A may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In one or more embodiments, ring CY14 in Formula 2B may be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.
In one or more embodiments, ring CY2 may 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, a borole group, a phosphole group, a silole group, a germole group, a selenophene 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.
Ring CY71 and ring CY72 in Formula 7 may each independently be a benzene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, or a fluorene group.
In an embodiment, ring CY71 may be a benzene group.
In one or more embodiments, ring CY72 may be a benzene group or a carbazole group.
L71 to L73 in Formula 7 may each independently be a single bond, 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.
For example, L71 to L73 may each independently be:
R21 to R23 in Formula 2B may each independently be a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or any combination thereof.
For example, R21 to R23 in Formula 2B may each independently be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or any combination thereof.
In an embodiment, R21 to R23 in Formula 2B may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, or —CD2CH3.
In one or more embodiments, R21 to R23 in Formula 2B may be identical to each other.
In one or more embodiments, two or more of R21 to R23 in Formula 2B may be different from each other.
Z0, Z1, Z2, Z29, Z30, R11 to R14, and R71 to R76 in Formulae 2A, 2B, and 7 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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 are respectively the same as those described herein.
d2 and e71 to e73 in Formulae 2A and 7 indicate the numbers of Ar2(s) and L71(s) to L73(s), respectively, and may each independently be an integer from 1 to 6. When d2 is 2 or more, two or more of Ar2(s) may be identical to or different from each other, when e71 is 2 or more, two or more of L71(s) may be identical to or different from each other, when e72 is 2 or more, two or more of L72(s) may be identical to or different from each other, and when e73 is 2 or more, two or more of L73(s) may be identical to or different from each other. For example, d2 and e71 to e73 may each independently be 1, 2, or 3. In an embodiment, d2 and e71 to e73 may each independently be 1 or 2.
a1 and b1 in Formulae 2A and 2B indicate the numbers of Z1(s) and R14(s), respectively, and may each independently be an integer from 0 to 20. When a1 is 2 or more, two or more of Z1(s) may be identical to or different from each other, and when b1 is 2 or more, two or more of R14(s) may be identical to or different from each other. For example, a1 and b1 may each independently be an integer from 0 to 10.
a2 in Formula 2A indicates the number of Z2(s), and may be an integer from 0 to 5. When a2 is 2 or more, two or more of Z2(s) may be identical to or different from each other. For example, a2 may be 0, 1, 2, or 3.
a73 in Formula 7 indicates the number of R73(s), and may be an integer from 0 to 8. When a73 is 2 or more, two or more of R73(s) may be identical to or different from each other. For example, a73 may be 0, 1, or 2.
In an embodiment, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be:
In one or more embodiments, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be:
In one or more embodiments, Z0 and Z2 in Formula 2A and R14 in Formula 2B may each independently be:
In one or more embodiments, R12 in Formula 2B may be hydrogen or a methyl group.
In one or more embodiments, R12 in Formula 2B may be a deuterated methyl group (for example, —CD3, —CD2H, or —CDH2).
In one or more embodiments, the number of carbon atoms included in R12 in Formula 2B may be 2 or more.
In one or more embodiments, R12 in Formula 2B may be:
In one or more embodiments, R12 in Formula 2B may be:
In one or more embodiments, R71 to R73 in Formula 7 may each independently be:
In one or more embodiments, Z0, Z1, Z2, Z29, Z30, R11 to R14, and R71 to R76 in Formulae 2A, 2B, and 7 may each independently be:
In one or more embodiments, Z1 in Formula 2A may not include Si.
In one or more embodiments, Z1 in Formula 2A may not be a group represented by —Si(Q3)(Q4)(Q5).
In one or more embodiments, R21 to R23, Z1, Z2, and R11 to R14 in Formulae 2A and 2B may each not include silicon (Si). As a result, an electronic device, such as an organic light-emitting device, including the first compound represented by Formula 1 may have improved out-coupling characteristics.
In one or more embodiments, the first compound represented by Formula 1 may satisfy at least one of Conditions A to C:
Condition A: in Formula 2A, Z1 is not hydrogen, and a1 is not 0.
Condition B: in Formula 2A, Z2 is not hydrogen, and a2 is not 0.
Condition C: in Formula 2B, R14 is not hydrogen, and b1 is not 0.
In one or more embodiments, the first compound represented by Formula 1 may include at least one deuterium atom, at least one fluoro group (—F), at least one cyano group (—CN), or any combination thereof.
In one or more embodiments, the first compound represented by Formula 1 may include at least one deuterium atom.
In one or more embodiments, the first compound represented by Formula 1 may satisfy at least one of Conditions (1) to (6), or Condition (7):
Condition (1): in Formula 2A, a1 is not 0, and at least one of Z1(s) in the number of a1 includes deuterium.
Condition (2): in Formula 2A, a2 is not 0, and at least one of Z2(s) in the number of a2 includes deuterium, a fluoro group (—F), a cyano group, or any combination thereof.
Condition (3): at least one of Ar2(s) in the number of d2 in Formula 2A includes deuterium, a fluoro group (—F), a cyano group, or any combination thereof.
Condition (4): at least one of R21 to R23 in Formula 2B includes deuterium.
Condition (5): R12 in Formula 2B includes at least one deuterium atom.
Condition (6): in Formula 2B, b1 is not 0, and at least one of R14(s) in the number of b1 includes deuterium, a fluoro group (—F), a cyano group, or any combination thereof.
Condition (7): Z1, Z2, and Ar2 in Formula 2A and R11 to R14 and R21 to R23 in Formula 2B each consist of only carbon and hydrogen.
In one or more embodiments, Z0, Z1, Z2, Z29, Z30, R11 to R14, and R71 to R76 in Formulae 2A, 2B, and 7 may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5) (wherein Q3 to Q5 are respectively the same as those described herein).
In one or more embodiments, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be hydrogen, deuterium, —CH3, —CD3, —CD2H, —CDH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-138 and 10-145, or a group represented by one of Formulae 10-1 to 10-138 and 10-145 in which at least one hydrogen is substituted with deuterium.
In one or more embodiments, Ar2 in Formula 2A may be a group represented by one of Formulae 10-12 to 10-145, a group represented by one of Formulae 10-12 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F.
In one or more embodiments, R12 in Formula 2B may be hydrogen, —CH3, —CH2D, —CHD2, or —CD3.
In one or more embodiments, R12 in Formula 2B may be hydrogen or a methyl group (—CH3).
In one or more embodiments, R12 in Formula 2B may be —CH2D, —CHD2, or —CD3.
In one or more embodiments, R12 in Formula 2B may be a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F.
In Formulae 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and OMe is a methoxy group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-637:
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-636:
In Formulae 2A and 2B, each of: i) two or more of R21 to R23; ii) two or more of a plurality of Z1(s); iii) two or more of a plurality of Z2(s); iv) R12 and R13; v) two or more of a plurality of R14(s); and vi) two or more of Z0, Z1, Z2, Z29, Z30, and R11 to R14 may optionally be linked together 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. That is, i) two or more of R21 to R23 may optionally be linked together 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, ii) two or more of a plurality of Z1(s) may optionally be linked together 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, iii) two or more of a plurality of Z2(s) may optionally be linked together 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, iv) R12 and R13 may optionally be linked together 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, v) two or more of a plurality of R14(s) may optionally be linked together 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 vi) two or more of Z0, Z1, Z2, Z29, Z30, and R11 to R14 may optionally be linked together 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.
R10a is the same as described in connection with R14.
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1.
In an embodiment, a group represented by
in Formula 2A may be a group represented by one of Formulae CY1(1) to CY1(16):
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY1-1 to CY1-28:
For example, ring CY10a may be a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.
In one or more embodiments, a group represented by in
Formula 2A may be a group represented by one of Formulae CY1-1, CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2-1 to CY2-6:
For example, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2-1 to CY2-6, and
In one or more embodiments,
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(1) to CY2(6):
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(1) to CY2(6), and may satisfy at least one of Conditions 1-1 to 1-8:
Condition 1-1: T28 in Formulae CY2(1) to CY2(6) is C(Ar28).
Condition 1-2: T27 in Formulae CY2(1) to CY2(6) is C(Ar27).
Condition 1-3: T26 in Formulae CY2(1) to CY2(6) is C(Ar26).
Condition 1-4: T25 in Formulae CY2(1) to CY2(6) is C(Ar25).
Condition 1-5: T24 in Formulae CY2(1), CY2(3), CY2(4), and CY2(6) is C(Ar24).
Condition 1-6: T23 in Formulae CY2(1) and CY2(6) is C(Ar23).
Condition 1-7: T22 in Formulae CY2(2) and CY2(5) is C(Ar22).
Condition 1-8: T21 in Formulae CY2(2) to CY2(5) is C(Ar21).
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(1) to CY2(6), and may satisfy at least one of Conditions 2-1 to 2-8:
Condition 2-1: in Formulae CY2(1) to CY2(6), T28 is C(Z28), and Z28 is not hydrogen.
Condition 2-2: in Formulae CY2(1) to CY2(6), T27 is C(Z27), and Z27 is not hydrogen.
Condition 2-3: in Formulae CY2(1) to CY2(6), T26 is C(Z26), and Z26 is not hydrogen.
Condition 2-4: in Formulae CY2(1) to CY2(6), T25 is C(Z25), and Z25 is not hydrogen.
Condition 2-5: in Formulae CY2(1), CY2(3), CY2(4), and CY2(6), T24 is C(Z24), and Z24 is not hydrogen.
Condition 2-6: in Formulae CY2(1) and CY2(6), T23 is C(Z23), and Z23 is not hydrogen.
Condition 2-7: in Formulae CY2(2) and CY2(5), T22 is C(Z22), and Z22 is not hydrogen.
Condition 2-8: in Formulae CY2(2) to CY2(5), T21 is C(Z21), and Z21 is not hydrogen.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2(1) to CY2(6), and may satisfy one of Conditions 3-1 to 3-9.
Condition 3-1: each of T21 to T28 in Formulae CY2(1) to CY2(6) is not N.
Condition 3-2: T28 in Formulae CY2(1) to CY2(6) is N.
Condition 3-3: T27 in Formulae CY2(1) to CY2(6) is N.
Condition 3-4: T26 in Formulae CY2(1) to CY2(6) is N.
Condition 3-5: T25 in Formulae CY2(1) to CY2(6) is N.
Condition 3-6: T24 in Formulae CY2(1), CY2(3), CY2(4), and CY2(6) is N.
Condition 3-7: T23 in Formulae CY2(1) and CY2(6) is N.
Condition 3-8: T22 in Formulae CY2(2) and CY2(5) is N.
Condition 3-9: T21 in Formulae CY2(2) to CY2(5) is N.
In one or more embodiments, a group represented by Formula CY2(1) may be a group represented by one of Formulae CY2(1)-1 to CY2(1)-4, a group represented by Formula CY2(2) may be a group represented by one of Formulae CY2(2)-1 to CY2(2)-4, a group represented by Formula CY2(3) may be a group represented by one of Formulae CY2(3)-1 to CY2(3)-3, a group represented by Formula CY2(4) may be a group represented by one of Formulae CY2(4)-1 to CY2(4)-3, a group represented by Formula CY2(5) may be a group represented by one of Formulae CY2(5)-1 to CY2(5)-4, and a group represented by Formula CY2(6) may be a group represented by one of Formulae CY2(6)-1 to CY2(6)-4:
For example, ring CY20a may be a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by one of Formulae CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, CY2-6-1 to CY2-6-65, and CY2-1-1N to CY2-1-25N:
In one or more embodiments, a group represented by
in Formula 2A may be a group represented by Formula CY2-1-25 or CY2-1-21N.
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by one of Formulae CY14-1 to CY14-64:
Alternatively, in Formulae CY14-1 to CY14-64,
In one or more embodiments, a group represented by
in Formula 2B may be a group represented by one of Formulae CY14(1) to CY14(63):
In one or more embodiments, the number of silicon (Si) atoms in the first compound represented by Formula 1 may be 1 or 2.
In one or more embodiments, the first compound represented by Formula 1 may be one of Compounds 1 to 5140 of Group A, one of Compounds 661 to 800, 1001 to 1280, and 1381 to 1620 of Group B, or one of Compounds 1-1 to 1-5 of Group C:
Meanwhile, the second compound is free of an electron-transporting group. The electron-transporting group may be, for example, a π-electron deficient nitrogen-containing cyclic group, a cyano group, a phosphine oxide group, a sulfoxide group, or the like.
The “π-electron deficient nitrogen-containing cyclic group” as used herein may be a C1-C60 heterocyclic group which has, as a ring-forming moiety, at least one *—N═*′ moiety. Examples of the π-electron deficient nitrogen-containing cyclic group may include a triazine group, an imidazole group, and the like.
For example, the second compound may include two or more carbazole groups.
In an embodiment, the second compound may be a compound represented by Formula 6:
In one or more embodiments, the second compound may be a compound represented by Formula 6-1, 6-2, or 6-3:
In one or more embodiments, L61 and L62 in Formulae 6 and 6-1 to 6-3 may each independently be a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, R61 to R64 in Formulae 6 and 6-1 to 6-3 may each independently be:
In one or more embodiments, the second compound may be one of Compounds 2-1 to 2-13:
Meanwhile, X74 to X76 in Formula 7 may each be N.
In an embodiment, ring CY71 in Formula 7 may be a benzene group.
In one or more embodiments, a group represented by
in Formula 7 may be represented by one of Formulae 7-1 to 7-7:
In one or more embodiments, L71 to L73 in Formula 7 may each independently be:
In one or more embodiments, R71 to R73 in Formula 7 may each independently be:
In one or more embodiments, in Formula 7,
In one or more embodiments, in Formula 7,
In one or more embodiments, the third compound may be one of Compounds 3-1 to 3-12:
In the descriptions of Formulae 6, 6-1 to 6-3, and 7 provided herein, R10a may be, for example:
For example, a highest occupied molecular orbital (HOMO) energy level of the second compound may be −5.5 eV or more.
In an embodiment, the HOMO energy level of the second compound may be in a range of about −5.5 eV to about −4.81 eV, about −5.5 eV to about −4.85 eV, or about −5.5 eV to about −4.9 eV.
In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the third compound may be about −1.8 eV or less.
In an embodiment, the LUMO energy level of the third compound may be in a range of about −2.5 eV to about −1.85 eV, about −2.5 eV to about −1.90 eV, or about −2.5 eV to about −1.95 eV.
The “HOMO energy level” as used herein may be a negative value that is evaluated based on density functional theory (DFT).
The first compound, the second compound, and the third compound as described herein may be included in the emission layer of the light-emitting device.
For example, the emission layer may include a mixture of the first compound, the second compound, and the third compound.
In an embodiment, the emission layer may include a dopant and a host, the dopant may include the first compound, and the host may include the second compound and the third compound. That is, the first compound may act as a dopant or an emitter in the emission layer. In this regard, a weight ratio of the second compound to the third compound may be in a range of about 1:9 to about 9:1, about 2:8 to about 8:2, about 3:7 to about 7:3, or about 4:6 to about 6:4. When the weight ratio of the second compound to the third compound is within the range described above, excitons may be effectively generated in the emission layer, and thus, the luminescence efficiency of the light-emitting device may be improved.
In one or more embodiments, in the emission layer, a total amount (for example, a weight) of the second compound and the third compound may be greater than an amount (for example, a weight) of the first compound.
In one or more embodiments, the emission layer may emit green light.
In one or more embodiments, the emission layer may emit green light having a maximum emission wavelength (or emission peak wavelength) in a range of about 500 nm to about 560 nm.
In the light-emitting device including the first compound, the second compound, and the third compound as described herein, migration of holes and electrons may be performed in a balanced manner, and excitons may be effectively formed. Accordingly, the light-emitting device may have excellent luminescence efficiency and long lifespan characteristics at the same time.
In the light-emitting device, 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. Alternatively, 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 light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the interlayer 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, 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, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
FIGURE schematically illustrates a cross-sectional view of an organic light-emitting device 10, which is a light-emitting device according to an embodiment of the present disclosure. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to an embodiment of the present disclosure will be described with reference to FIGURE. The organic light-emitting device 10 may have a structure in which a first electrode 11, an interlayer 15, and a second electrode 19 are sequentially stacked.
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 include materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 15 may be arranged on the first electrode 11.
The interlayer 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, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material for forming 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 10−8 torr to about 10−3 torr, and a deposition rate in a range of about 0.01 Å/sec to about 100 Å/sec.
When the hole injection layer is formed by spin coating, the coating conditions may vary depending on a material for forming 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 rpm to about 5,000 rpm and a heat treatment temperature in a range of about 80° C. to about 200° C. for removing a solvent after coating.
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 m-MTDATA, TDATA, 2-TNATA, NPB, 3-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:
Ar101 and Ar102 in Formula 201 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.
xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:
R109 in Formula 201 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.
In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A:
For example, the hole transport region may include one of Compounds HT1 to HT20 or any combination thereof:
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 3,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within 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 as 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 a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. For example, the p-dopant may be: a quinone derivative such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; metal oxide, such as tungsten oxide and molybdenum oxide; a cyano group-containing compound, such as Compound HT-D1; or any combination thereof.
The hole 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 increase efficiency.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include a material that is used in the hole transport region as described above, a host material described below, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP described below, Compound 2-1 described above, or the like may be used as the material for forming the emission layer.
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, or 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 although the deposition or coating conditions may vary according to a material that is used to form the hole transport layer.
For example, the emission layer may include a host and a dopant, wherein the dopant may include the first compound, and the host may include the second compound and the third compound. The first compound, the second compound, and the third compound are respectively the same as those described herein.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.
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 1,000 Å. When the thickness of the emission layer is within the range described above, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Next, the electron transport region is arranged on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be 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, BCP, Bphen, BAlq, or any combination thereof:
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within the range described above, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
In one or more embodiments, the electron transport layer may include one of Compounds ET1 to ET25 or any combination thereof:
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, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may 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 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 range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 is arranged on the interlayer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (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 FIGURE, but embodiments of the present disclosure are not limited thereto.
According to another aspect, the light-emitting device as described herein may be included in an electronic apparatus. Thus, an electronic apparatus including the light-emitting device is provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, and the like.
According to another aspect, provided is a mixture including:
In an embodiment, the mixture may include the third compound and the first compound.
In one or more embodiments, the mixture may include the third compound and the second compound.
In one or more embodiments, the mixture may include all of the third compound, the second compound, and the first compound.
The first compound, the second compound, and the third compound are respectively the same as those described herein.
The mixture may be used in various methods, for example, deposition, coating, and the like, when forming the light-emitting device as described herein.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used here refers to a divalent group having the same structure as the C1-C60 alkyl group.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. For example, Formula 9-33 is a branched C6 alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
The term “C1-C60 alkoxy group” as 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, a propoxy group, a butoxy group, and a pentoxy group.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and the term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
Examples of the C3-C10 cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms, and the term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group may include a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and has 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 “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the ring thereof. Examples of the C2-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 C2-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group that includes 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 that includes 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 two or more 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-C60 heteroaryl group” as used herein refers to a monovalent group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a carbocyclic aromatic system having 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the two or more rings may be fused to each other.
The C2-C60 alkylheteroaryl group used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group), and the term “C1-C60 alkylthio group” as used herein indicates —SA104 (wherein A104 is the C1-C60 alkyl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as 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 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as 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. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a (or at least one Z0))” as used herein may include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, and a fluorene group (each unsubstituted or substituted with at least one R10a (or at least one Z0)).
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a (or at least one Z0))” as used herein may include a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an 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, and a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R10a (or at least one Z0)).
Examples of the “C5-C30 carbocyclic group” and “C1-C30 heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
The terms “fluorinated C1-C60 alkyl group (or a fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group,” and “fluorinated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group (that is, a fluorinated methyl group)” includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or a fluorinated C1-C20 alkyl group or the like)”, “the fluorinated C3-C10 cycloalkyl group”, “the fluorinated C1-C10 heterocycloalkyl group”, or “the fluorinated a phenyl group” may be i) a fully fluorinated C1-C60 alkyl group (or a fully fluorinated C1-C20 alkyl group or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or a partially fluorinated C1-C20 alkyl group or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or a partially fluorinated phenyl group, wherein, in each group, all hydrogen included therein is not substituted with a fluoro group.
The terms “deuterated C1-C60 alkyl group (or a deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group (that is, the deuterated methyl group)” may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C1-C60 alkyl group (or the deuterated C1-C20 alkyl group or the like)”, “the deuterated C3-C10 cycloalkyl group”, “the deuterated C1-C10 heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C1-C60 alkyl group (or a fully deuterated C1-C20 alkyl group or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein is substituted with deuterium, or ii) a partially deuterated C1-C60 alkyl group (or a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein is not substituted with deuterium.
The term “(C1-C20 alkyl) ‘X’ group” as used herein refers to an ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl) phenyl group is a toluyl group.
As used herein, the number of carbons in each group that is substituted (e.g., C1-C60) excludes the number of carbons in the substituent. For example, a C1-C60 alkyl group can be substituted with a C1-C60 alkyl group. The total number of carbons included in the C1-C60 alkyl group substituted with the C1-C60 alkyl group is not limited to 60 carbons. In addition, more than one C1-C60 alkyl substituent may be present on the C1-C60 alkyl group. This definition is not limited to the C1-C60 alkyl group and applies to all substituted groups that recite a carbon range.
The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzothiophene 5,5-dioxide group,” in which, in each group, at least one carbon selected from ring-forming carbons is substituted with nitrogen.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted 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 each independently be:
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 as used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C1-C60 alkylthio group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 as used herein may each independently be:
Hereinafter, an organic light-emitting device according to an embodiment of the present disclosure will be described in detail with reference to Examples. However, the present disclosure is not limited to the following examples.
The HOMO energy level and LUMO energy level of each of Compounds 2-1, 2-A, 3-1, 3-A, and 3-B were evaluated using the Gaussian 09 program with molecular structure optimization obtained by B3LYP-based DFT. Results thereof are summarized in Table 1.
An ITO (as an anode)-patterned glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water, each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
Compound HT3 and F6-TCNNQ were vacuum-co deposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å, and then, Compound 2-1 was deposited on the hole transport layer to form a buffer layer having a thickness of 300 Å.
Next, Compound 2-1 (second compound), Compound 3-1 (third compound), and Compound 1-A (first compound) were co-deposited on the buffer layer at a weight ratio of 57:38:5 to form an emission layer having a thickness of 400 Å.
Then, Compound ET3 and ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Comparative Example A, except that each of the first compound, the second compound, and the third compound was changed as shown in Table 2 in forming the emission layer. Compound 1(1) is the same compound as Compound 21 of Group A described herein.
The maximum value of external quantum efficiency (Max EQE) (%) and lifespan (LT97) (hr) of each of the organic light-emitting devices manufactured according to Comparative Examples A to D and Example 1 were evaluated. Results thereof are summarized in Table 2 as relative values (%). A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as apparatuses for evaluation, the lifespan (LT97) (at 16,000 nit) was obtained by measuring the amount of time (hr) that elapsed until luminance was reduced to 97% of the initial luminance of 100%, and the results were converted into relative values (%).
From Table 2, it was confirmed that the organic light-emitting device of Example 1 had excellent luminescence efficiency (external quantum efficiency) and lifespan characteristics at the same time, as compared with the organic light-emitting devices of Comparative Examples A to D.
Organic light-emitting devices were manufactured in the same manner as in Comparative Example A, except that the first compound in the emission layer was changed as shown in Table 3.
The maximum value of external quantum efficiency (Max EQE) (%) and lifespan (LT97) (hr) of each of the organic light-emitting devices manufactured according to Examples 11 to 15 were evaluated in the same manner as in Evaluation Example 2. Results thereof are summarized in Table 3 as relative values (%). For comparison, the external quantum efficiency and lifespan data of Comparative Example A are also shown in Table 3.
From Table 3, it was confirmed that the organic light-emitting devices of Examples 11 to 15 had excellent luminescence efficiency (external quantum efficiency) and lifespan characteristics at the same time, as compared with the organic light-emitting device of Comparative Example A.
The light-emitting device according to an embodiment of the present disclosure may have excellent luminescence efficiency (external quantum efficiency) and excellent lifespan characteristics at the same time. Accordingly, a high-quality electronic apparatus may be manufactured 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 |
|---|---|---|---|
| 10-2022-0025500 | Feb 2022 | KR | national |
