Patent Application
20250115625
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2023-0128488, filed on Sep. 25, 2023, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
The disclosure relates to a condensed cyclic compound, a light-emitting device including the same, and an electronic apparatus including the light-emitting device.
Organic light-emitting devices among light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed, compared to devices in the art, and can produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an interlayer that is arranged between the anode and the cathode and includes an emission layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided 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. The excitons may transition from an excited state to a ground state, thereby generating light.
Provided are a novel condensed cyclic compound, a light-emitting device including the same, 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 condensed cyclic compound represented by Formula 1 is provided:
According to another aspect of the disclosure, a light-emitting device includes a first electrode, a second electrode, and an interlayer that is arranges between the first electrode and the second electrode and includes an emission layer, wherein the interlayer includes at least one of the condensed cyclic compound.
According to another aspect of the disclosure, electronic equipment 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 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 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 condensed cyclic compound provided herein may be represented by Formula 1:
wherein, in Formula 1, ring Y1 to ring Y3 may each independently be a C5-C60 carbocyclic group or a C3-C60 heterocyclic group.
In an embodiment, in Formula 1, ring Y1 to ring Y3 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.
In one or more embodiments, ring Y1 to ring Y3 may each independently be a benzene group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In Formula 1, W2 may be a single bond, O, S, N[(Ar2)d2-(T2)e2], C(T2a)(T2b), or Si(T2a)(T2b), and W3 may be a single bond, O, S, N[(Ar3)d3-(T3)e3], C(T3a)(T3b), or Si(T3a)(T3b). Ar2, Ar3, d2, d3, T2, T3, e2, e3, T2a, T2b, T3a, and T3b may each be the same as described herein.
In Formula 1, n2 and n3 may each independently be 0 or 1, and the sum of n2 and n3 may be 1 or more. When n2 is 0, *—(W2)n2—*′ may be absent, and when n3 is 0, *—(W3)n3—*′ may be absent.
For example, in Formula 1,
In an embodiment, in Formula 1, n2 may be 1, and W2 may be N[(Ar2)d2-(T2)e2].
L1, L2, L3, Ar1, Ar2, and Ar3 may each independently be a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R1a, or a C3-C60 heterocyclic group unsubstituted or substituted with at least one R1a. R1a may be the same as described herein.
In an embodiment, L1, L2, L3, Ar1, Ar2, and Ar3 may each independently be:
In one or more embodiments, each of Ar1, Ar2, and Ar3 may not be a single bond.
a1, a2, a3, d1, d2, and d3 may represent the number of L1, L2, L3, Ar1, Ar2, and Ar3, respectively, and may each independently be an integer from 1 to 5. When a1 is 2 or more, two or more of L1 may be identical to or different from each other, when a2 is 2 or more, two or more of L2 may be identical to or different from each other, when a3 is 2 or more, two or more of L3 may be identical to or different from each other, when d1 is 2 or more, two or more of Ar1 may be identical to or different from each other, when d2 is 2 or more, two or more of Ar2 may be identical to or different from each other, and when d3 is 2 or more, two or more of Ar3 may be identical to or different from each other. For example, a1, a2, a3, d1, d2, and d3 may each independently be 1, 2, or 3.
Z1, Z2, Z3, T1, T2, T3, T2a, T2b, T3a, T3b, and R1a may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), —P(Q8)(Q9), or a group represented by Formula 2:
Q1 to Q9 may each be the same as described herein.
In an embodiment, Z1, Z2, Z3, T1, T2, T3, T2a, T2b, T3a, T3b, and R1a may each independently be:
Q1 and Q2 may each independently be a C1-C20 alkyl group, a phenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, or a dibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a phenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a fluorenyl group, a dibenzosilolyl group, or any combination thereof.
In one or more embodiments, in Formula 2, R1 and R2 may each independently be hydrogen; R1 may be hydrogen, and R2 may be deuterium; or R1 and R2 may each independently be deuterium.
In one or more embodiments, in Formula 2, R3 to R5 may each independently be a C1-C10 alkyl group unsubstituted or substituted with deuterium, —F, cyano group, or any combination thereof.
In the present specification, examples of a C1-C60 alkyl group, a C1-C20 alkyl group, or a C1-C10 alkyl group may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, and the like.
In one or more embodiments, the group represented by Formula 2 may include at least one deuterium.
b1, b2, b3, c1, c2, c3, e1, e2, and e3 may represent the number of Z1, Z2, Z3, a group represented by *-(L1)a1-(Z1)b1, a group represented by *-(L2)a2-(Z2)b2, a group represented by *-(L3)a3-(Z3)b3, T1, T2, and T3, respectively, and may each independently be an integer from 1 to 20. When b1 is 2 or more, two or more of Z1 may be identical to or different from each other, when b2 is 2 or more, two or more of Z2 may be identical to or different from each other, when b3 is 2 or more, two or more of Z3 may be identical to or different from each other, when c1 is 2 or more, two or more of a group represented by *-(L1)a1-(Z1)b1 may be identical to or different from each other, when c2 is 2 or more, two or more of a group represented by *-(L2)a2-(Z2)b2 may be identical to or different from each other, when c3 is 2 or more, two or more of a group represented by *-(L3)a3-(Z3)b3 may be identical to or different from each other, when e1 is 2 or more, two or more of T1 may be identical to or different from each other, when e2 is 2 or more, two or more of T2 may be identical to or different from each other, and when e3 is 2 or more, two or more of T3 may be identical to or different from each other. For example, b1, b2, b3, c1, c2, c3, e1, e2, and e3 may each independently be an integer from 1 to 10 or an integer from 1 to 6.
Formula 1 may include at least one of the group represented by Formula 2.
In an embodiment, Formula 1 may satisfy at least one of Conditions 1 to 5:
In one or more embodiments, Formula 1 may satisfy at least one of Conditions 1A, 2A, 3A, 4A, 4B, 5A, and Condition 5B:
In one or more embodiments, Formula 1 may satisfy at least one of Conditions 6 to 8:
In an embodiment, in Formulae 3, 4, 5-1, and 5-2, Zn to Z18, Z21 to Z28, and Z31 to Z38 may each independently be:
In one or more embodiments, in Formulae 3, 4, 5-1, and 5-2, Z11 to Z18, Z21 to Z28, and Z31 to Z38 may each independently be hydrogen or deuterium.
In one or more embodiments, regarding Z11 to Z18 in Formula 3, i) at least one of Z13 and Z16 may be a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remaining groups of Z11 to Z18 may each be hydrogen or deuterium.
In one or more embodiments, regarding Z21 to Z28 in Formula 4, i) at least one of Z23 and Z26 may be a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remaining groups of Z21 to Z28 may each be hydrogen or deuterium.
In one or more embodiments, regarding Z31 to Z38 in Formula 5-1, i) at least one of Z33 and Z36 may be a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remaining groups of Z31 to Z38 may each be hydrogen or deuterium.
In one or more embodiments, regarding Z31 to Z35 in Formula 5-2, i) Z33 may be a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remaining of Z31 to Z35 may each be hydrogen or deuterium.
In one or more embodiments, n2 is 1, W2 is N[(Ar2)d2-(T2)e2], and the at least one of *-(L1)a1-(Z1)b1, *-(L2)a2-(Z2)b2, and *-(L3)a3-(Z3)3 includes a group represented by Formula 2.
In one or more embodiments, a group represented by *—(Ar1)a1-(T1)e1 in Formula 1 may be a group represented by one of Formulae 7-1 to 7-6:
For example, T13 in Formulae 7-1 and 7-2, at least one of Y11, T12, and T14 in Formulae 7-3 and 7-4, and at least one of Y11, T12, T14, X12, and X14 in Formulae 7-5 and 7-6 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2.
In an embodiment, in Formulae 7-1 to 7-6, T11 to T15 and Y11 to Y14 may each independently be:
In one or more embodiments, in Formulae 7-1 to 7-6, T11 to T15, Y11 to Y14, and X11 to X15 may each independently be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15 and Y11 to Y14 in Formulae 7-1 and 7-2, i) T13 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15 and Y11 to Y14 in Formulae 7-3 and 7-4, i) Y11 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15 and Y11 to Y14 in Formulae 7-3 and 7-4, i) Y11 and T12 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15 and Y11 to Y14 in Formulae 7-3 and 7-4, i) Y11, T12, and T14 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15, Y11 to Y13, and X11 to X15 in Formulae 7-5 and 7-6, i) Y11 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T11 to T15, Y11 to Y13, and X11 to X15 in Formulae 7-5 and 7-6, i) Y11, T12, and X12 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, in Formula 1, n2 may be 1, W2 may be N[(Ar2)d2-(T2)e2], and a group represented by *—(Ar2)d2-(T2)e2 may be a group represented by one of Formulae 8-1 to 8-6:
For example, T23 in Formulae 8-1 and 8-2, at least one of Y21, T22, and T24 in Formulae 8-3 and 8-4, and at least one of Y21, T22, T24, X22, and X24 in Formulae 8-5 and 8-6 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2.
In an embodiment, in Formulae 8-1 to 8-6, T21 to T25 and Y21 to Y24 may each independently be:
In one or more embodiments, in Formulae 8-1 to 8-6, T21 to T25, Y21 to Y24, and X21 to X25 may each independently be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25 and Y21 to Y24 in Formulae 8-1 and 8-2, i) T23 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25 and Y21 to Y24 in Formulae 8-3 and 8-4, i) Y21 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25 and Y21 to Y24 in Formulae 8-3 and 8-4, i) Y21 and T22 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25 and Y21 to Y24 in Formulae 8-3 and 8-4, i) Y21, T22, and T24 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25, Y21 to Y23, and X21 to X25 in Formulae 8-5 and 8-6, i) Y21 may be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, regarding T21 to T25, Y21 to Y23, and X21 to X25 in Formulae 8-5 and 8-6, i) Y21, T22, and X22 may each independently be: a phenyl group or a tert-butyl group, each unsubstituted or substituted with at least one deuterium; or a group represented by Formula 2, and ii) the remainder may each be hydrogen or deuterium.
In one or more embodiments, the number of the group represented by 2 included in the condensed cyclic compound represented by Formula 1 may be 1 to 10, for example, 1 to 6.
In one or more embodiments, two or more of Z1, Z2, Z3, T1, T2, T3, T2a, T2b, T3a, and T3b may optionally be linked together to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a.
In one or more embodiments, the condensed cyclic compound represented by Formula 1 may have a symmetric structure.
In one or more embodiments, in Formula 1, W2 may be N[(Ar2)d2-(T2)e2], and a group represented by *—(Ar1)d1-(T1)e1 and a group represented by *—(Ar2)d2-(T2)e2 may be identical to each other.
In one or more embodiments, in Formula 1, a group represented by *-(L1)a1-(Z1)b1 and a group represented by represented by *-(L2)a2-(Z2)e2 may be identical to each other.
In one or more embodiments, the condensed cyclic compound represented by Formula 1 may have an asymmetric structure.
In one or more embodiments, in Formula 1, W2 may be N[(Ar2)d2-(T2)e2], and a group represented by *—(Ar1)d1-(T1)e1 and a group represented by *—(Ar2)d2-(T2)e2 may be different from each other.
In one or more embodiments, in Formula 1, a group represented by *-(L1)a1-(Z1)b1 and a group represented by represented by *-(L2)a2-(Z2)e2 may be different from each other.
In one or more embodiments, n2 is 1, W2 is N[(Ar2)d2-(T2)e2], the at least one of *-(L1)a1-(Z1)b1, *-(L2)a2-(Z2)b2, and *-(L3)a3-(Z3)3 includes a group represented by Formula 2, *—(Ar1)d1-(T1)e1 is represented by Formula 7-5 and *—(Ar2)d2-(T2)e2 is represented by Formula 8-5.
In one or more embodiments, the condensed cyclic compound represented by Formula 1 may be represented by Formula 1A, 1B, or 1C:
The description of Formula 1 may also be applied to Formulae 1A to 1C.
For example, Formulae 1A to 1C may satisfy at least one of Conditions 1 to 5.
In one or more embodiments, Formulae 1A to 1C may satisfy at least one of Conditions 1A, 2A, 3A, 4A, 4B, 5A, and Condition 5B.
In one or more embodiments, Formulae 1A to 1C may satisfy at least one of Conditions 6 to 8.
In one or more embodiments, a group represented by *—(Ar1)d1-(T1)e1 in Formulae 1A to 1C may be a group represented by one of Formulae 7-1 to 7-6.
In one or more embodiments, a group represented by *—(Ar2)d2-(T2)e2 in Formulae 1A to 1C may be a group represented by one of Formulae 8-1 to 8-6.
In one or more embodiments, Formulae 1 and 1A to 1C may include at least one deuterium, at least one tert-butyl group, or any combination thereof.
In one or more embodiments, the condensed cyclic compound may be a multiple resonance thermally activated delayed fluorescence material.
In one or more embodiments, the condensed cyclic compound may be one of Compounds 1 to 760:
Formula 1 may include at least one group represented by Formula 2:
In Formula 2, each of R1 and R2 may not include carbon, and each of R3 to R5 may not be hydrogen and deuterium, but may be a C1-C60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof. In this regard, the reaction rate of electrophilic carbon to which R1 and R2 are bonded may be slowed down, so that the bond dissociation energy (BDE) of chemical bonds between “the group represented by Formula 2” and “atoms (e.g., carbon)” bonded to the group represented by Formula 2 in the condensed cyclic compound of Formula 1 may be increased, and thereby the thermal stability of the condensed cyclic compound of Formula 1 may be increased. In addition, since each of R3 to R5 is a C1-C60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof, the condensed cyclic compound represented by Formula 1 may have relatively high singlet energy. Accordingly, a light-emitting device including the condensed cyclic compound represented by Formula 1 may have excellent lifespan and excellent luminescence efficiency characteristics.
In an embodiment, a full width at half maximum (FWHM) of an emission spectrum of the condensed cyclic compound may be in a range of about 5 nm to about 30 nm, for example, about 10 nm to about 25 nm.
In one or more embodiments, the emission peak wavelength of the emission spectrum of the condensed cyclic compound may be in a range of about 400 nm to about 500 nm, for example, about 440 nm to about 470 nm.
In one or more embodiments, a singlet (S1) energy level of the condensed cyclic compound may be in a range of about 2.4 eV to about 3.1 eV, for example, about 2.7 eV to about 2.8 eV.
In one or more embodiments, an absolute value of the difference between a singlet (S1) energy level and a triplet (T1) energy level of the condensed cyclic compound may be in a range of about 0 eV to about 1 eV, for example, about 0.08 eV to about 0.2 eV.
In one or more embodiments, an absolute value of a highest occupied molecular orbital (HOMO) energy level of the condensed cyclic compound may be in a range of about 4.0 eV to about 6.5 eV, for example, about 4.8 eV to about 5.0 eV.
In one or more embodiments, the absolute value of the HOMO energy level of the condensed cyclic compound may be in a range of about 1.1 eV to 1.7 eV, for example, about 1.2 eV to about 1.41 eV.
Synthesis methods for the condensed cyclic compound may be recognized by those skilled in the art with reference to Synthesis Examples to be described later.
The condensed cyclic compound may be suitable for use as an interlayer of a light-emitting device, for example, as an emission layer material in the interlayer. In this regard, another 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 interlayer includes at least one condensed cyclic compound represented by Formula 1.
Such a light-emitting device is provided with an interlayer including at least one condensed cyclic compound represented by Formula 1. In this regard, the light-emitting device may be able to emit blue light having a relatively narrow FWHM and a short-wavelength shift, and may have improved driving voltage, improved external quantum efficiency, improved luminescence efficiency, and/or improved lifespan characteristics.
The condensed cyclic compound may be used between a pair of electrodes of the light-emitting device. For example, the condensed cyclic compound may be included in the emission layer. Here, the emission layer may further include a host. The amount of the host may be greater than that of the condensed cyclic compound. The emission layer may emit red light, green light, or blue light. For example, the emission layer may emit blue light.
In an embodiment, the CIEy value of light emitted from the emission layer may be in a range of about 0.040 to about 0.170, about 0.050 to about 0.170, about 0.060 to about 0.170, about 0.040 to about 0.165, about 0.050 to about 0.165, or about 0.060 to about 0.165.
In one or more embodiments, the emission peak wavelength of light emitted from the emission layer may be in a range of about 440 nm to about 470 nm, about 445 nm to about 470 nm, about 450 nm to about 470 nm, about 455 nm to about 470 nm, about 460 nm to about 470 nm, about 440 nm to about 465 nm, about 445 nm to about 465 nm, about 450 nm to about 465 nm, about 455 nm to about 465 nm, or about 460 nm to about 465 nm.
The emission layer may further include a host. A detailed description of the host may be the same as described herein.
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
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, 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 “interlayer” as used herein refers to a single layer and/or multiple layers arranged between the first electrode and the second electrode of the light-emitting device.
The “interlayer” may include, in addition to an organic compound, an organometallic complex including metal or the like.
For example, the emission layer may include a first embodiment or a second embodiment.
The emission layer may include at least one condensed cyclic compound represented by Formula 1, and the condensed cyclic compound may serve as an emitter, e.g., a delayed fluorescence emitter. That is, the condensed cyclic compound may be an emitter. For example, among total luminescent components in the emission layer, luminescent components derived from the condensed cyclic compound may account for 80% or more, 85% or more, 90% or more, or 95% or more. Light emitted from the condensed cyclic compound may be blue light. The emission layer may further include a sensitizer, and the sensitizer and the condensed cyclic compound may be different from each other. The sensitizer may be an organometallic compound, a delayed fluorescence material, a prompt fluorescence material, or any combination thereof. The amount (weight) of the sensitizer may be about 0.01 parts by weight to about 10 parts by weight, per 100 parts by weight of the emission layer.
The emission layer may include at least one condensed cyclic compound represented by Formula 1, and the condensed cyclic compound may serve as a sensitizer or an auxiliary dopant. That is, the condensed cyclic compound may be a sensitizer or an auxiliary dopant. The sensitizer may effectively transfer excitons from the host to the emitter. The emission layer may further include an emitter, and the emitter may be different from the condensed cyclic compound. The emitter may be an organometallic compound, a prompt fluorescence material, a delayed fluorescence material, or any combination thereof.
In the present specification, the emitter may be a material that receives excitons from a host, a sensitizer, and/or an auxiliary dopant and emits light through transition to the ground state.
In the first embodiment and the second embodiment, the amount of the condensed cyclic compound may be about 0.01 parts by weight to about 40 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 1 part by weight to about 20 parts by weight, per 100 parts by weight of the emission layer.
In the first embodiment and the second embodiment, the organometallic compound may include a transition metal and n ligand(s) bonded to the transition metal, wherein n may be an integer from 1 to 4.
In an embodiment, the transition metal in the organometallic compound may be platinum (Pt) or palladium (Pd), n may be 1, and the ligand may be a tetradentate ligand.
The tetradentate ligand may include, for example, a carbene moiety bonded to the transition metal.
In one or more embodiments, the organometallic compound may include a transition metal and a tetradentate ligand bonded to the transition metal, wherein the transition metal may be Pt or Pd, and the tetradentate ligand may include a carbene moiety bonded to the transition metal.
In one or more embodiments, in the organometallic compound, the transition metal may be iridium (Ir) or osmium (Os), and n may be 3, wherein at least one ligand among the n ligand(s) may be: a bidentate ligand including —F, a cyano group, or a combination thereof; or a bidentate ligand including a carbene moiety bonded to the transition metal. For example, the bidentate ligand may further include an imidazole group or a triazole group.
In one or more embodiments, the organometallic compound may be an organometallic compound represented by Formula 3A and/or an organometallic compound represented by Formula 5. A detailed description of Formulae 3A and 5 will be provided below.
In the first embodiment and the second embodiment, the delayed fluorescence material may be, for example, a thermally activated delayed fluorescence material. In one or more embodiments, the delayed fluorescence material may be a multiple resonance thermally activated delayed fluorescence material.
The multiple resonance thermally activated delayed fluorescence material may be a polycyclic compound that i) does not include a transition metal, and ii) includes a core in which two or more C3-C60 cyclic groups are condensed with each other. Here, two C3-C60 cyclic groups of the core may be condensed with each other while sharing boron (B) or nitrogen (N).
In an embodiment, the delayed fluorescence material may be a polycyclic compound represented by Formula 4A. A detailed description of Formula 4A will be provided below.
In the first embodiment and the second embodiment, the prompt fluorescence material may be an amino group-containing compound, a styryl group-containing compound, or the like. For example, the prompt fluorescence material may include a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group (i.g., a tetracene group), a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a group represented by one of Formulae 501-1 to 501-21, or any combination thereof:
In one or more embodiments, the prompt fluorescence material may include a compound represented by Formula 501A or 501B:
In one or more embodiments, the prompt fluorescence material may include a compound represented by Formula 501A or 501B, wherein xd4 in Formula 501A may be 1, 2, 3, 4, 5, or 6, and xd4 in Formula 501B may be 2, 3, or 4.
The emission layer may include m1 host(s) which may include a hole transport compound, an electron transport compound, a bipolar compound, or any combination thereof. m1 may be an integer from 1 to 3. Each of the m1 host(s) may not include a transition metal.
For example, in the emission layer, m1 may be 2, and two hosts in the emission layer may include a hole transport compound and an electron transport compound, respectively, wherein the hole transport compound and the electron transport compound may be different from each other.
In an embodiment, the hole transport compound may include at least one π electron-rich C3-C60 cyclic group, and may not include an electron transport group. Examples of the electron transport group may include a cyano group, a fluoro group (—F), a π-electron deficient nitrogen-containing cyclic group, a phosphine oxide group, a sulfoxide group, and the like.
The term “π-electron deficient nitrogen-containing cyclic group” as used herein refers to a C1-C60 heterocyclic group including at least one *—N=*′ moiety as a ring-forming moiety. Examples of the π-electron deficient nitrogen-containing cyclic group may include a triazine group, an imidazole group, and the like.
The term “r electron-rich C3-C60 cyclic group” as used herein refers to a C3-C60 cyclic group not including *—N=*′ moiety as a ring-forming moiety. Examples of the r electron-rich C3-C60 cyclic group may include a benzene group, a naphthalene group, a triphenylene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, and the like.
For example, the hole transport compound may include two or more carbazole groups.
In one or more embodiments, the electron transport compound may be a compound including at least one electron transport group. Examples of the electron transport group may include a cyano group, a fluoro group, a r electron deficient nitrogen-containing C1-C60 cyclic group, a phosphine oxide group, a sulfoxide group, or any combination thereof. In an embodiment, the electron transport compound may include a triazine group.
For example, the electron transport compound may include at least one electron transport group (e.g., a triazine group) and at least one r electron-rich C3-C60 cyclic group (e.g., a benzene group, a naphthalene group, a triphenylene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, or any combination thereof).
In an embodiment, the hole transport compound may be a compound represented by Formula 6:
Q3 to Q5 and Q33 to Q35 may each be the same as described herein.
In one or more embodiments, the hole transport compound may be a compound represented by Formula 6-1, 6-2, or 6-3:
wherein, in Formulae 6-1 to 6-3, L61, L62, R61 to R64, e61, e62, a63, and a64 may each be the same as described herein.
In one or more embodiments, the hole transport compound may be one of Compounds HTH1 to HTH6:
In one or more embodiments, the electron transport compound may be a compound represented by Formula 7:
Q3 to Q5 and Q33 to Q35 may each be the same as described herein.
In one or more embodiments, each of X74 to X76 in Formula 7 may be N.
In one or more embodiments, L71 to L73 in Formula 7 may each independently be a benzene group, a naphthalene group, a triphenylene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, —Si(Q33)(Q34)(Q35), or any combination thereof.
In one or more embodiments, in Formula 7, at least one of e71 L71(s), at least one of e72 L72(s), at least one of e73 L73(s), or any combination thereof may each independently be a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, —Si(Q33)(Q34)(Q35), or any combination thereof.
In one or more embodiments, in Formula 7, at least one of e71 L71(s), at least one of e72 L72(s), at least one of e73 L73(s), or any combination thereof may each independently include a carbazole group, an indolocarbazole group, a benzocarbazole group, a naphthocarbazole group, or a dibenzocarbazole group, wherein a nitrogen atom of a pyrrole group of the carbazole group, the indolocarbazole group, the benzocarbazole group, the naphthocarbazole group, or the dibenzocarbazole group may be linked to a carbon atom of a 6-membered ring including X74 to X76 in Formula 7, via a single bond or neighboring L71, L72, and/or L73.
In one or more embodiments, in Formula 7, e71 to e73 indicate the numbers of L71 to L73, respectively, and may each independently be 1, 2, 3, 4, or 5.
In one or more embodiments, R71 to R76 in Formula 7 may each independently be:
In one or more embodiments, the electron transport compound may be one of Compounds ETH1 to ETH7:
In the first embodiment and the second embodiment, the organometallic compound may be an organometallic compound represented by Formula 3A:
In an embodiment, M31 in Formula 3A may be Pt, Pd, or Au.
In an embodiment, M31 in Formula 3A may be Pt or Pd.
In one or more embodiments, in Formula 3A, a bond between X11 and M31 may be a coordinate bond.
In one or more embodiments, in Formula 3A, X11 may be C, and a bond between X11 and M31 may be a coordinate bond. That is, X11 in Formula 3A may be C in a carbene moiety.
In one or more embodiments, ring CY31 to ring CY34 in Formula 3A may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
In an embodiment, R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b may each independently be:
In an embodiment, the organometallic compound represented by Formula 3A may be an organometallic compound represented by Formula 3-1 or an organometallic compound represented by Formula 3-2:
In Formula 3-2, a bond between carbon of the benzimidazole group and M31 may be a coordinate bond. That is, in Formula 3-2, the benzimidazole group may include a carbene moiety bonded to M31.
In Formulae 3-1 and 3-2,
In an embodiment, in Formulae 3-1 and 3-2,
For example, in Formulae 3-1 and 3-2, at least one of R311 to R317 may include
In the first embodiment and the second embodiment, the organometallic compound may be an organometallic compound represented by Formula 5 wherein M51 in Formula 5 may be a transition metal.
M51(L51)n51(L52)n52 Formula 5
In an embodiment, 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), titanium (T1), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In one or more embodiments, M51 may be Ir, Pt, Os, or Rh.
In one or more embodiments, M51 may be Ir or Os.
In Formula 5, L51 may be a ligand represented by Formula 5A, and L52 may be a ligand represented by Formula 5B:
wherein Formulae 5A and 5B may each be the same 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 L52 may be identical to or different from each other.
The sum of n51 and n52 in Formula 5 may be 2 or 3. For example, the sum of n51 and n52 may be 3.
In an embodiment, in Formula 5, i) M may be Ir, and n51+n52=3; or ii) M may be Pt, and n51+n52=2.
In one or more embodiments, in Formula 5, M 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.
L51 and L52 in Formula 5 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.
Ring CY51 to ring CY54 in Formulae 5A and 5B may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, ring CY51 to ring CY54 in Formulae 5A and 5B may each independently include i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensed ring in which two or more fourth rings are condensed with each other, or v) a condensed ring in which at least one third ring is condensed with at least one fourth ring, wherein the third ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and the fourth ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one or more embodiments, in Formulae 5A and 5B, ring CY1 to ring CY4 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole 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.
For example, ring CY51 and ring CY53 in Formulae 5A and 5B may be different from each other.
In one or more embodiments, ring CY52 and ring CY54 in Formulae 5A and 5B may be different from each other.
In one or more embodiments, ring CY51 to ring CY54 in Formulae 5A and 5B may be different from each other.
R51 to R54 in Formulae 5A and 5B may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q51)(Q52), —Si(Q53)(Q54)(Q55), —Ge(Q53)(Q54)(Q55), —B(Q56)(Q57), —P(═O)(Q58)(Q59), or —P(Q58)(Q59). Q51 to Q59 are each the same as described in the present specification.
In an embodiment, R51 to R54 in Formulae 5A and 5B 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, —SFs, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
In one or more embodiments, R51 to R54 may each independently be:
In Formulae 5A and 5B, b51 to b54 indicate the numbers of R51 to 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, in Formula 5A, Y52 may be C, a bond between Y52 and M51 may be a covalent bond, and at least one of b52 R52(s) may be a cyano group or —F.
In one or more embodiments, in Formula 5A, Y51 may be N, a bond between Y51 and M51 may be a coordinate bond, CY51 may be an imidazole group, a triazole group, a benzimidazole group, or a triazolopyridine group, and at least one of b52 R52(s) may be a cyano group or —F.
In one or more embodiments, in Formula 5A, Y51 may be C, and a bond between Y51 and M51 may be a coordinate bond.
In one or more embodiments, in Formula 5A, Y51 may be C, a bond between Y51 and M51 may be a coordinate bond, and CY51 may be a benzimidazole group or an imidazopyrazine group.
Specific examples of organometallic compound of Formulae 3A or 5
For example, the organometallic compound represented by Formulae 3A or 5 may be one of Compounds P1 to P52:
In the first embodiment and the second embodiment, the delayed fluorescence material may be a polycyclic compound represented by Formula 4A:
In an embodiment, ring CY41 to ring CY43 may each independently be i) a benzene group, or ii) a polycyclic group in which two or more C3-C30 cyclic groups are condensed with each other. Here, two C3-C30 cyclic groups of the polycyclic group may be condensed with each other while sharing boron (B) or nitrogen (N).
In one or more embodiments, at least one of b41 to b43 may be 1, or at least wo of b41 to b43 may each be 1. In one or more embodiments, two of b41 to b43 may be 1, and the remaining one may be 0.
In one or more embodiments, R41 to R49 may each independently be:
In one or more embodiments, the polycyclic compound represented by Formula 4A may be a polycyclic compound represented by one of Formulae 4-1 to 4-9:
The polycyclic compound represented by Formula 4A may be selected from Compounds D1 to D30:
The
In the FIGURE, an organic light-emitting device 10 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an interlayer 10A arranged between the first electrode 11 and the second electrode 19.
The interlayer 10A includes an emission layer 15, a hole transport region 12 is arranged between the first electrode 11 and the emission layer 15, and an electron transport region 17 is arranged between the emission layer 15 and the second electrode 19.
A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.
The first electrode 11 may be formed by, for example, depositing or sputtering, onto the substrate, a material for forming the first electrode 11. 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. In an embodiment, when the first electrode 11 is a transmissive electrode, the material for forming the first electrode 11 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 11 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers.
A thickness of the emission layer 15 may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer 15 is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
In an embodiment, the emission layer 15 may include the aforementioned condensed cyclic compound represented by Formula 1. The emission layer 15 may include the first embodiment or the second embodiment.
The emission layer 15 may further include, in addition to the condensed cyclic compound, the sensitizer, and/or the emitter, the host.
Hole transport region 12
The hole transport region 12 may be arranged between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.
The hole transport region 12 may have a single-layer structure or a multi-layer structure.
For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer/hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer/electron blocking layer structure, a hole transport layer/organic layer structure, a hole injection layer/hole transport layer/organic layer structure, a hole transport layer/electron blocking layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure.
The hole transport region 12 may include any compound having hole-transporting properties.
For example, the hole transport region 12 may include an amine-based compound.
In an embodiment, the hole transport region 12 may include m-MTDATA, TDATA, 2-TNATA, NPB, β—NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor-sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by one of Formulae 201 to 205, or any combination thereof:
For example, L201 to L209 may be
In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound.
In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.
The carbazole-containing amine-based compound may include, for example, compounds represented by Formula 201 including a carbazole group and further including at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.
The carbazole-free amine-based compound may include, for example, compounds represented by Formula 201 not including a carbazole group and including at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.
In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201-1, 202-1, or 201-2, or any combination thereof:
wherein, in Formulae 201-1, 202-1, and 201-2, L201 to L203, L205, xa1 to xa3, xa5, R201 and R202 are each the same as described in connection with Formulae 201 to 205 herein, and R211 to R213 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, or a pyridinyl group.
In an embodiment, the hole transport region 12 may include one of Compounds HT1 to HT39 or any combination thereof:
In one or more embodiments, the hole transport region 12 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (for example, at least one of compounds represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.
In an embodiment, the LUMO energy level of the p-dopant may be less than or equal to about −3.5 eV.
The p-dopant may include a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.
For example, the p-dopant may include:
The compound represented by Formula 221 may include, for example, Compound HT-D2:
The hole transport region 12 may have a thickness in a range about 100 Å to about 10,000 Å, for example, about 400 Å to about 2,000 Å, and the emission layer 15 may have a thickness in a range of about 100 Å to about 3,000 Å, for example, about 300 Å to about 1,000 Å. When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges, satisfactory hole transportation characteristics and/or luminescence characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region 12 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 15, and thus, efficiency of a formed organic light-emitting device may be improved.
The hole transport region 12 may further include an electron blocking layer. The electron blocking layer may include a known material, for example, mCP or DBFPO:
The electron transport region 17 is arranged between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.
The electron transport region 17 may have a single-layer structure or a multi-layer structure.
For example, the electron transport region 17 may have an electron transport layer, an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, hole blocking layer/electron transport layer structure, a buffer layer/electron transport layer/electron injection layer structure, or a hole blocking layer/electron transport layer/electron injection layer structure. The electron transport region 17 may further include an electron control layer.
The electron transport region 17 may include known electron-transporting materials.
The electron transport region 17 (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing C1-C60 cyclic group. The π electron-deficient nitrogen-containing C1-C60 cyclic group is the same as described herein.
For example, the electron transport region 17 may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21. Formula 601
In an embodiment, at least one of Ar601(s) in the number of xe11 and R601(s) in the number of xe21 may include the π electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, Ar601 and L601 in Formula 601 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof, and
When xe11 in Formula 601 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:
In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In one or more embodiments, R601 and R611 to R613 in Formulae 601 and 601-1 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or any combination thereof; or
The electron transport region 17 may include one of Compounds ET1 to ET36 or any combination thereof:
In one or more embodiments, the electron transport region 17 may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, DBFPO, or any combination thereof. For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include BCP or Bphen:
Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region 17 (for example, the electron transport layer in the electron transport region 17) may further include, in addition to the aforementioned materials, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may include a Li ion, a Na ion, a K ion, a Rb ion, a Cs ion, or any combination thereof, and a metal ion of the alkaline earth metal complex may include a Be ion, a Mg ion, a Ca ion, a Sr ion, a Ba ion, or any combination thereof. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxydiphenyloxadiazole, a hydroxydiphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may directly contact the second electrode 19.
The electron injection layer may have i) a single-layer structure consisting of a single layer including a single material, ii) a single-layer structure consisting of a single layer including multiple materials that are different from each other, or iii) a multi-layer structure consisting of multiple layers including multiple materials that are different from each other.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs.
The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof.
The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides and/or halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, the rare earth metal, or any combination thereof.
The alkali metal compound may include: one of alkali metal oxides such as Li2O, Cs2O, K2O, and the like; one of alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and the like; or any combination thereof. In an embodiment, the alkali metal compound may include LiF, Li2O, NaF, LiI, NaI, CsI, KI, or any combination thereof.
The alkaline earth-metal compound may include one of alkaline earth-metal compounds, such as BaO, SrO, CaO, BaxSr1-xO (wherein 0<x<1), BaxCa1-xO (wherein 0<x<1), or any combination thereof. In an embodiment, the alkaline earth metal compound may include BaO, SrO, CaO, or any combination thereof.
The rare earth metal compound may include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, TbF3, or any combination thereof. In an embodiment, the rare earth metal compound may include YbF3, ScF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth metal complex, or the rare earth metal complex may include hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 is arranged on the aforementioned interlayer 10A. The second electrode 19 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be selected from a metal, an alloy, an electrically conductive compound, or any combination thereof, which have a relatively low work function.
The second electrode 19 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg—In, Mg—Ag, ITO, IZO, or any combination thereof. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 19 may have a single-layer structure having a single layer or a multi-layer structure including two or more layers.
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 are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof.
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, 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 are 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 are 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 as a ring-forming atom, 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 are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (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 as a ring-forming atom, and the term “the 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 are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent hydrocarbon cyclic group that includes 3 to 10 carbon atoms as a ring-forming atom and at least one carbon-carbon double bond in the ring thereof and has no aromaticity, and examples thereof are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms as a ring-forming atom, and at least one carbon-carbon double bond in the ring thereof and has no aromaticity. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms as a ring-forming atom, 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 as a ring-forming atom. Examples of the C6-C60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group that includes a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms as a ring-forming atom, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group that includes a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms as a ring-forming atom. 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, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group in which two or more rings are condensed with each other, only carbon atom is used as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the whole molecule is a non-aromaticity group. An example of the monovalent non-aromatic condensed polycyclic group is 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 described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed with each other, a heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in the entire molecular structure thereof. An example of the monovalent non-aromatic condensed heteropolycyclic group is 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 described above.
The term “π electron-depleted nitrogen-containing C1-C60 cyclic group” as used herein refers to a cyclic group having 1 to 60 carbon atoms and including at least one *—N=*′ (wherein * and *′ each indicate a binding site to a neighboring atom) as a ring-forming moiety. For example, the π electron-depleted nitrogen-containing C1-C60 cyclic group may be a) a first ring, b) a condensed ring in which at least two first rings are condensed, or c) a condensed ring in which at least one first ring and at least one second ring are condensed.
The term “π electron-rich C3-C60 cyclic group” as used herein refers to a cyclic group having 3 to 60 carbon atoms and not including at least one *—N=*′ (wherein * and *′ each indicate a binding site to an adjacent atom) as a ring-forming moiety. For example, the π electron-rich C3-C60 cyclic group may be a) a second ring or b) a condensed ring in which at least two second rings are condensed.
The term “C5-C60 carbocyclic group” and “C5-C30 carbocyclic group” as used herein refers to a monocyclic or polycyclic group having 5 to 60 or 5 to 30 carbon atoms as a ring-forming atom, respectively, and may be, for example, a) a third ring or b) a condensed ring in which two or more third rings are condensed with each other.
The term “C1-C60 heterocyclic group” and “C1-C30 heterocyclic group” as used herein refers to a monocyclic or polycyclic group that has 1 to 60 or 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, respectively, and may be, for example, a) a fourth ring, b) a condensed ring in which two or more fourth rings are condensed with each other, or c) a condensed ring in which at least one third ring is condensed with at least one fourth ring.
The “first ring” as used herein may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, or a thiadiazole group.
The “second ring” as used herein may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.
The “third ring” as used herein may be a cyclopentane group, a cyclopentadiene group, an indene group, 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 group (a norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, or a benzene group.
The “fourth ring” as used herein may be a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, a triazasilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
For example, the π electron-depleted nitrogen-containing C1-C60 cyclic group may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group.
For example, the π electron-rich C3-C60 cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, a pyrrolophenanthrene group, a furanophenanthrene group, a thienophenanthrene group, a benzonaphthofuran group, a benzonapthothiophene group, an (indolo)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothieno)phenanthrene group.
For example, the C5-C60 carbocyclic group or the C5-C30 carbocyclic group may be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, an indene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, an indene group, a fluorene 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.
For example, the C1-C60 heterocyclic group or the C1-C30 heterocyclic group may be a thiophene group, a furan group, a pyrrole group, a cyclopentadiene 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-fluorene-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-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 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, or a benzothiadiazole group.
The terms “a π electron-deficient nitrogen-containing C1-C60 cyclic group, a π electron-rich C3-C60 cyclic group, a C5-C60 carbocyclic group, a C5-C30 carbocyclic group, a C1-C60 heterocyclic group, and a C1-C30 heterocyclic group” as used herein each refer to a part of a condensed ring or a monovalent, a divalent, a trivalent, a tetravalent, a pentavalent, or a hexavalent group, depending on the formula structure.
A substituent of the substituted π electron-deficient nitrogen-containing C1-C60 cyclic group, the substituted π electron-rich C3-C60 carbocyclic group, the substituted C5-C30 cyclic group, the substituted C5-C60 cyclic group, the substituted C1-C60 heterocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkylene group, the substituted C2-C60 alkenylene group, the substituted C2-C60 alkynylene group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic 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 C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be hydrogen; deuterium; —F; or a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
Unless otherwise defined, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be, for example:
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 term “room temperature” as used herein refers to a temperature of about 25° C.
The terms “a biphenyl group, a terphenyl group, and a quaterphenyl group (a tetraphenyl group)” used herein respectively refer to monovalent groups in which two, three, or four phenyl groups which are linked together via a single bond. A term “(C1-C20 alkyl) X group” (e.g., (C1-C20 alkyl) phenyl group) used herein refers to an X group (e.g., a phenyl group) substituted with at least one C1-C20 alkyl.
Hereinafter, a compound and a light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the compound and the light-emitting device is not limited thereto. The wording “‘B’ was used instead of ‘A’” used in describing Synthesis Examples means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.
In a nitrogen atmosphere, 5-neopentyl-N1,N3-bis(3,3″,5′-tri-tert-butyl-[1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,3-diamine (20.00 g, 20.59 mmol), 1-bromo-3-iodobenzene (19.97 g, 70.59 mmol), Cul (1.96 g, 10.29 mmol), K2CO3 (1.42 g, 10.29 mmol), and dimethyl formamide (DMF, 82 ml) were mixed together and heated at 150° C. for 24 hours. Then, the reaction was terminated with an aqueous ammonium chloride solution thereto. Afterwards, a resultant product obtained by extraction with dichloromethane was dried with MgSO4, filtered, and the filtrate was concentrated to remove the solvent. The crude product was purified by column chromatography using methylene chloride (MC) and hexane (in a volume ratio of 1:5), so as to obtain a while solid, Compound 181-2 (15.42 g).
LCMS (m/z) calculated: 1280.591 g/mol, measured: [M+] 1280.935 g/mol
In a nitrogen atmosphere, Compound 181-2 (15.42 g, 12.03 mmol) was mixed with 120 ml of 1,2-dichlorobenzene and BI3 (7.07 g, 18.05 mol), and the mixed solution was stirred for 24 hours after raising the temperature to 150° C. Afterwards, the temperature was lowered to room temperature, and the reaction was terminated with a Na2CO3 (aq.) solution. The organic layer obtained by performing an extraction process thereon was dried with MgSO4, the solvent was removed, and the crude product was then purified by column chromatography using MC and hexane (in a volume ratio of 1:4), so as to obtain Compound 181-1 (3.68 g).
LCMS (m/z) calculated: 1288.578 g/mol, measured: [M+] 1289.423 g/mol
In a nitrogen atmosphere, Compound 181-1 (1.00 g, 0.78 mmol), carbazole (0.31 g, 1.86 mmol), Pd2(dba)3 (0.071 g, 0.078 mmol), S-phos (0.064 g, 0.16 mmol), and sodium tert-butoxide (0.26 g, 2.71 mmol) were mixed with toluene, and heated at 110° C. for 5 hours. Then, the reaction was terminated with an ammonium chloride solution. An organic layer obtained by performing an extraction process thereon was dried with MgSO4 to remove the solvent therefrom, and then purified by column chromatography using MC and hexane (in a volume ratio of 1:3), so as to obtain Compound 181 (0.50 g).
LCMS (m/z) calculated: 1460.875 g/mol, measured: [M+] 1461.745 g/mol
In a nitrogen atmosphere, N1,N3-bis(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)-5-neopentylbenzene-1,3-diamine (15 g, 20.08 mmol), 1-bromo-3-iodobenzene (19.47 g, 68.82 mmol), Cul (1.91 g, 10.04 mmol), K2CO3 (1.39 g, 10.04 mmol), and DMF (82 ml) were mixed and heated at 150° C. for 24 hours. Then, the reaction was terminated with an aqueous ammonium chloride solution. Afterwards, the reaction mixture was extracted with dichloromethane. The organic layer was dried with MgSO4, the solvent was removed, and the crude product was then purified by column chromatography using MC and hexane (in a volume ratio of 1:3), so as to obtain a while solid, Compound 161-2 (12.48 g).
LCMS (m/z) calculated: 1056.344 g/mol, measured: [M+] 1055.428 g/mol
In a nitrogen atmosphere, Compound 161-2 (12.48 g, 11.81 mmol) was mixed with 120 ml of 1,2-dichlorobenzene and BI3 (6.93 g, 17.71 mmol), and the mixed solution was stirred for 24 hours after raising the temperature to 150° C. Afterwards, the temperature was lowered to room temperature, and the reaction was terminated with an aqueous Na2CO3 solution. The organic layer was dried with MgSO4 and the solvent was removed therefrom, and then the crude product was purified by column chromatography using MC and hexane (in a volume ratio of 1:2), so as to obtain Compound 161-1 (3.31 g).
LCMS (m/z) calculated: 1062.329 g/mol, measured: [M+] 1063.512 g/mol
In a nitrogen atmosphere, Compound 161-1 (1.00 g, 0.94 mmol), carbazole (0.38 g, 2.27 mmol), Pd2(dba)3 (0.086 g, 0.094 mmol), S-phos (0.077 g, 0.19 mmol), and sodium tert-butoxide (0.32 g, 3.33 mmol) were mixed with toluene, and heated at 110° C. for 5 hours. Then, the reaction was terminated with an aqueous ammonium chloride solution. The organic layer was dried with MgSO4, the solvent was removed therefrom, and then the crude product purified by column chromatography using MC and hexane (in a volume ratio of 1:3), so as to obtain Compound 161 (0.8 g).
LCMS (m/z) calculated: 1236.624 g/mol, measured: [M+] 1237.521 g/mol Evaluation Example 1
For each of Compounds R1, R2, 181, and 161, by using a Gaussian 16 program, the density functional theory (DFT) calculation based on the molecular structure optimized through B3LYP/6-31G(d,p) functions was performed to evaluate HOMO energy level, LUMO energy level, S1 energy level, T1 energy level, and ΔEst (absolute value of a difference between S1 energy and T1 energy) of each of Compounds R1, R2, 181, and 161. The results are summarized in Table 1.
Next, for each of Compounds R1, R2, 181, and 161, the thermal analysis was performed by using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) (N2 atmosphere, temperature range:room temperature to 800° C. (10° C./min) for TGA, room temperature to 400° C. for DSC, Pan Type:Pt Pan in disposable Al Pan (TGA), disposable Al pan (DSC)). The results are also summarized in Table 1. In Table 1, “Ts_10%” indicates sublimation temperature, specifically, a temperature at which the compounds lost 10% of their weight in the thermal analysis.
Referring to Table 1, it was confirmed that Compounds 181 and 161 had electrical properties suitable for light-emitting devices. Also, based on the relatively low sublimation temperatures that Compounds 181 and 161 had, it was confirmed that thin films with excellent performance could be prepared by using Compounds 181 and 161.
For each of Compounds 181, R4, R7, R9, and R10, the bond dissociation energy (BDE) was measured between a group indicated by the dotted line and carbon to which the group indicated by the dotted line bonded, the BDE with the carbon at the ground state (S0 BDE) by DFT calculation based on the molecular structure optimized through B3LYP/6-31G(d,p) functions by using a Gaussian 16 program. The results are summarized in Table 2.
Referring to Table 2, it was confirmed that Compound 181, which includes the group represented by Formula 2 as the group indicated by the dotted line, had the highest S0 BDE value.
A glass substrate with a 1,500 Å-thick ITO electrode formed thereon was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with acetone isopropyl alcohol and pure water each for 15 minutes, and cleaned by UV-ozone-irradiation for 30 minutes.
Subsequently, m-MTDATA was deposited on the ITO electrode (i.e., anode) of the glass substrate to form a hole injection layer having a thickness of 600 Å, and α-NPD was deposited on the hole injection layer to form a hole transport layer having a thickness of 250 Å.
Next, Compound R1 (emitter) and mCP (host) were co-deposited on the hole transport layer in a weight ratio of 10:90 to form an emission layer having a thickness of 400 Å.
BAlq was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was 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 second electrode (i.e., cathode) having a thickness of 1,200 Å, thereby completing the manufacture of a light-emitting device having a structure of ITO/m-MTDATA (600 Å)/α—NPD (250 Å)/mCP+Compound R1 (10 wt %) (400 Å)/BAlq(50 Å)/Alq3 (300 Å)/LiF (10 Å)/Al (1,200 Å).
Light-emitting devices were manufactured in the same manner as in Comparative Example R1, except that compounds shown in Table 3 were each used instead of Compound R1 in forming an emission layer.
For each of the light-emitting devices of Comparative Examples R1 and R2 and Examples 1 and 2, emission peak wavelength (i.e., maximum emission wavelength or peak emission wavelength) and FWHM of the electroluminescence (EL) spectrum, FWHM, driving voltage, and lifetime (LT95 at 1,000 nit) were evaluated, and the results are shown in Table 3. The emission peak wavelengths of the EL spectrum and the FWHM were evaluated for each light-emitting device based on the EL spectrum measured by using a luminance meter (Minolta Cs-1000A). The driving voltage and lifetime were evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The lifetime (LT95 at 1,000 nit) is the time (hr) required for the luminance to reach 95% of the initial luminance of 100%, and is expressed by converting the measured time into relative values (%).
Referring to Table 3, it was confirmed that the light-emitting devices of Examples 1 and 2 that emitted blue light had improved or equivalent driving voltage and improved lifespan characteristics, compared to the light-emitting devices of Comparative Examples R1 and R2.
According to the one or more embodiments, a condensed cyclic compound represented by Formula 1 may emit blue light with a narrow full width at half maximum. Moreover, the condensed cyclic compound represented by Formula 1 may have a relatively small singlet energy and a relatively high thermal stability, and thus an electronic device, e.g., a light-emitting device, including the condensed cyclic compound may have improved lifespan characteristics. The electronic device, e.g., the light-emitting device may further have improved driving voltage.
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 |
|---|---|---|---|
| 10-2023-0128488 | Sep 2023 | KR | national |
