Patent Application
20180114928
This application claims priority to Korean Patent Application No. 10-2016-0140443, filed on Oct. 26, 2016, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated herein in its entirety by reference.
One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
Organic light-emitting devices (OLEDs) are self-emission devices, which have superior characteristics in terms of a viewing angle, a response time, and a brightness, a driving voltage, and a response speed, and which produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
Meanwhile, luminescent compounds may be used to monitor, sense, or detect a biological material such as a cell protein. Examples of such luminescent compounds include a phosphorescent luminescent compound.
Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.
One or more embodiments include a novel organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.
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.
According to one or more embodiments, an organometallic compound is represented by Formula 1:
In Formula 1,
According to one or more embodiments, an organic light-emitting device includes:
The organometallic compounds may act as a dopant in the emission layer.
According to one or more embodiments, a diagnostic composition includes at least one organometallic compound represented by Formula 1.
These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present disclosure. 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 in contact with 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 of the present embodiments.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
The term “or” means “and/or.” 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.
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 general inventive concept 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.
“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%, 5% of the stated value.
An organometallic compound according to an embodiment may be represented by Formula 1:
M in Formula 1 may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
In an embodiment, M in Formula 1 may be platinum, but embodiments of the present disclosure are not limited thereto.
The organometallic compound represented by Formula 1 may be a neutral compound which does not consist of an ion pair of an anion and a cation.
In Formula 1, X1 may be O or S, and a bond between X1 and M may be a covalent bond.
In Formula 1, X3 and X4 may each independently be N or C, a bond between N and M may be a coordinate bond, and one of a bond selected from a bond between X3 and M and a bond between X4 and M may be a covalent bond, and the other may be a coordinate bond.
For example, X1 in Formula 1 may be 0, but embodiments of the present disclosure are not limited thereto.
In Formula 1, Y1, Y7, Y8, and Y9 may each independently be C or N, Y11 may be C, N, O, or S, and a bond between X3 and Y7, a bond between X3 and Y8, a bond between X4 and Y9, and a bond between X4 and Y11 may each independently be a single bond or a double bond.
For example, Y1, Y7, Y8, and Y9 in Formula 1 may each be C, and Y11 may be N or C.
In an embodiment, in Formula 1, X3 may be C, X4 may be N, a bond between X3 and M may be a covalent bond, a bond between X4 and M may be a coordinate bond, and Y1, Y7, Y8, and Y9 may each be C, but embodiments of the present disclosure are not limited thereto.
CY3 and CY4 in Formula 1 may each independently be selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group.
For example, in Formula 1,
In an embodiment, in Formula 1,
In an embodiment, in Formula 1, CY3 may be a benzene group or a pyridine group, and CY4 may be a pyridine group, a quinoline group, an isoquinoline group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, but embodiments of the present disclosure are not limited thereto.
In Formula 1, X11 may be N or C-[(L11)c11-(R11)a11], X12 may be N or C-[(L12)c12-(R12)a12], X13 may be N or C-[(L13)c13-(R13)a13], X14 may be N or C-[(L14)c14-(R14)a14], X21 may be N or C-[(L21)c21-(R21)a21], X22 may be N or C-[(L22)c22-(R22)a22], X23 may be N or C-[(L23)c23-(R23)a23], provided that at least one of X11 to X14 and X21 to X23 may be N.
For example, in Formula 1, 1) one or two of X11 to X14 may be N and all of X21 to X23 may not be N, 2) all of X11 to X14 may not be N and one or two of X21 to X23 may be N, or 3) one or two of X11 to X14 may be N and one or two of X21 to X23 may be N.
In an embodiment, in Formula 1, 1) one of X11 to X14 may be N and the others thereof may not be N, and all of X21 to X23 may not be N, 2) all of X11 to X14 may not be N, and one of X21 to X23 may be N and the others thereof may not be N, or 3) one of X11 to X14 may be N and the others may not be N, and one of X21 to X23 may be N and the others thereof may not be N.
T1 to T3 in Formula 1 may each independently be selected from *—O—*′, *—S—*′, *—C(R5)(R6)—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—N(R5)—*′, *—Si(R5)(R6)—*′, and *—P(R5)(R6)—*′. R5 and R6 are the same as described below. * and *′ each indicate a binding site to a neighboring atom.
R5 and R6 may optionally be linked via a first linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, T1 to T3 in Formula 1 may each independently be selected from *—O—*′, *—S—*′, *—C(R5)(R6)—*′, *—N(R5)—*′, *—Si(R5)(R6)—*′, and *—P(R5)(R6)—*′.
In one or more embodiments, in Formula 1,
b1, b2, and b3 in Formula 1 respectively indicate the number of T1, the number of T2, and the number of T3, and may each independently be 0, 1, 2, or 3. When b1 is zero, *-(T1)b1-*′ may be a single bond, when b1 is two or more, two or more groups T1 may be identical to or different from each other, when b2 is zero, *-(T2)b2-*′ may be a single bond, when b2 is two or more, two or more groups T2 may be identical to or different from each other, when b3 is zero, *-(T3)b3-*′ may be a single bond, and when b3 is two or more, two or more groups T3 may be identical to or different from each other.
For example, b1 to b3 may each independently be 0 or 1.
The sum of b1, b2, and b3 in Formula 1 may be 0, or may be 1 or more.
In one or more embodiments, in Formula 1,
X51 in Formula 1 may be selected from O, S, N(R7), C(R7)(R8), Si(R7)(R8), and C(═O). R7 and R8 are the same as described herein.
R7 and R8 may optionally be linked via a second linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
The first linking group and the second linking group may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(R9)(R10)—*′, *—C(R9)=*′, *═C(R9)—*′, *—C(R9)═C(R10)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—N(R9)—*′, *—Si(R9)(R10)—*′, and *—P(R9)(R10)—*′, and R9 and R10 are the same as described herein.
In an embodiment, X51 in Formula 1 may be selected from O, S, N-[(L7)c7-(R7)a7], C(R7)(R8), Si(R7)(R8), and C(═O), but embodiments of the present disclosure are not limited thereto.
For example, X51 in Formula 1 may be O, S, or N-[(L7)c7-(R7)a7], but embodiments of the present disclosure are not limited thereto.
R7 and R8 may optionally be linked via a second linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
L3, L4, L7, L11 to L14, and L21 to L23 may each independently be selected from a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, and a substituted or unsubstituted C1-C30 heterocyclic group.
For example, L3, L4, L7, L11 to L14, and L21 to L23 may each independently be selected from:
c3, c4, c7, c11, c12, c13, c14, c21, c22, and c23 respectively indicate the number of groups L3, the number of groups L4, the number of groups L7, the number of groups L11, the number of groups L12, the number of groups L13, the number of groups L14, the number of groups L21, the number of groups L22, and the number of groups L23, may each independently be an integer from 1 to 5, or may each independently be 1 or 2.
R3 to R8, R11 to R14, and R21 to R23 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl 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), —B(Q6)(Q7), and —P(═O)(Q8)(Q9). Q1 to Q09 are each independently the same as described herein.
For example, R3 to R8, R11 to R14, and R21 to R23 may each independently be selected from:
In an embodiment, R3 to R8, R11 to R14, and R21 to R23 may each independently be selected from:
In an embodiment, R3 to R8, R11 to R14, and R21 to R23 may each independently be selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-139, and —Si(Q3)(Q4)(Q5), but embodiments of the present disclosure are not limited thereto:
Q3 to Q9 may each independently be selected from:
a3, a4, a7, a11 to a14, a21 to a23, d3, and d4 in Formula 1 may each independently be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2.
In Formula 1, two of *-(L11)c11-(R11)a11, *-(L12)c12-(R12)a12, *-(L13)c13-(R13)a13, and *-(L14)c14-(R14)a14 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of *-(L21)c21-(R21)a21, *-(L22)c22-(R22)a22, and *-(L23)c23-(R23)a23 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, two of groups *-(L3)c3-(R3)a3 in the number of d3 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, and two groups *-(L4)c4-(R4)a4 in the number of d4 may optionally be linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
For example, in Formula 1, the substituted or unsubstituted C5-C30 carbocyclic group or the substituted or unsubstituted C1-C30 heterocyclic group, which may be formed by optionally linking two of *-(L11)c11-(R11)a11, *-(L12)c12-(R12)a12, *-(L13)c13-(R13)a13, and *-(L14)c14-(R14)a14, the substituted or unsubstituted C5-C30 carbocyclic group or the substituted or unsubstituted C1-C30 heterocyclic group, which may be formed by optionally linking two of *-(L21)c21-(R21)a21, *-(L22)c22-(R22)a22, and *-(L23)c23-(R23)a23, the substituted or unsubstituted C5-C30 carbocyclic group or the substituted or unsubstituted C1-C30 heterocyclic group, which may be formed by optionally linking two of groups *-(L3)c3-(R3)a3 in the number of d3, and the substituted or unsubstituted C5-C30 carbocyclic group or the substituted or unsubstituted C1-C30 heterocyclic group, which may be formed by optionally linking two of groups *-(L4)c4-(R4)a4 in the number of d4, may be selected from:
R1a is the same as described in connection with R3.
In an embodiment, a moiety represented by
in Formula 1 may be selected from groups represented by Formulae CY1-1 to CY1-16, and
in Formula 1 may be selected from groups represented by Formulae CY2-1 to CY2-5:
In Formulae CY1-1 to CY1-16,
In Formulae CY2-1 to CY2-5,
For example,
in Formula 1 may be selected from groups represented by Formulae CY1-1 to CY1-16, provided that i) at least one of X11 to X14 in Formula CY1-1 is N, at least one of X13 and X14 in Formulae CY1-2, CY1-5, CY1-8, CY1-11, and CY1-12 is N, at least one of X11 and X14 in Formulae CY1-3, CY1-6, CY1-9, CY1-13, and CY1-14 is N, and at least one of X11 and X12 in Formulae CY1-4, CY1-7, CY1-10, CY1-15, and CY1-16 is N, and ii) a moiety represented by
may be a group represented by Formula CY2-1;
in Formula 1 may be selected from groups represented by Formulae CY1-1 to CY1-16, provided that i) all of X11 to X14 in Formulae CY1-1 to CY1-16 are not N, and ii) a moiety represented by
may be selected from groups represented by Formulae CY2-2 to CY2-5; or
in Formula 1 may be selected from groups represented by Formulae CY1-1 to CY1-16, provided that i) at least one of X11 to X14 in Formula CY1-1 is N, at least one of X13 and X14 in Formulae CY1-2, CY1-5, CY1-8, CY1-11, and CY1-12 is N, at least one of X11 and X14 in Formulae CY1-3, CY1-6, CY1-9, CY1-13, and CY1-14 is N, and at least one of X11 and X12 in Formulae CY1-4, CY1-7, CY1-10, CY1-15, and CY1-16 is N, and ii) a moiety represented by
may be selected from groups represented by Formulae CY2-2 to CY2-5, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments,
in Formula 1 may be selected from groups represented by Formulae CY3-1 to CY3-22:
In Formulae CY3-1 to CY3-22,
In one or more embodiments,
a moiety represented by
in Formula 1 may be selected from groups represented by Formulae CY4-1 to CY4-8:
In Formulae CY4-1 to CY4-8,
In one or more embodiments, the organometallic compound may be represented by Formula 1-1 or 1-2,
may be selected from groups represented by Formulae CY1-1(2) to CY1-1(8), and a moiety represented by
may be a group represented by Formula CY2-1;
may be a group represented by Formula CY1-1(1), and a moiety represented by
may be selected from groups represented by Formulae CY2-2 to CY2-5; or
may be selected from groups represented by Formulae CY1-1(2) to CY1-1(8), and a moiety represented by
may be selected from groups represented by Formulae CY2-2 to CY2-5, but embodiments of the present disclosure are not limited thereto:
In Formulae 1-1, 1-2, CY1-1(1) to CY1-1(8), and CY2-1 to CY2-5,
For example, the organometallic compound may be one of Compounds 1 to 822, but embodiments of the present disclosure are not limited thereto:
An electronic device, for example, an organic light-emitting device which includes the organometallic compound represented by Formula 1, may have improved characteristics in terms of a driving voltage, a current density, luminance, current efficiency, power efficiency, color purity, a roll-off ratio, and/or a lifespan.
For example, a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a singlet (Si) energy level, a triplet (T1) energy level, and a maximum emission wavelength of each of Compounds 2, 153, 821, 822, 261, and 241 were evaluated by a density functional theory (DFT) method of a Gaussian program (the structure was optimized at a B3LYP, 6-31G(d,p) level). Evaluation results are shown in Table 1.
From Table 1, it has been determined that the organometallic compound represented by Formula 1 has electrical characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by those of ordinary skill in the art by referring to Synthesis Examples provided below.
The organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant of an emission layer in the organic layer. Thus, another aspect of the present disclosure provides an organic light-emitting device including:
The organic light-emitting device may have, due to the inclusion of the organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high luminescent efficiency, high power efficiency, high quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.
The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
The expression “(an organic layer) includes at least one of organometallic compounds” as used herein may include an embodiment in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and an embodiment in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may be included in an emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be included in an identical layer (for example, Compound 1 and Compound 2 all may be included in an emission layer).
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.
In an embodiment, in the organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and wherein the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
The FIGURE is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
The organic layer 15 is disposed on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be disposed between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
A hole injection layer may be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 1002C to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 Angstroms per second (A/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
The hole transport region may include at least one selected from 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/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:
Ar101 and Ar102 in Formula 201 may each independently be selected from:
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xb are not limited thereto.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and so on), or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);
a C1-C10 alkyl group or a C1-C10 alkoxy group, each substituted with at least one selected from 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, and a phosphoric acid group or a salt thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, and a C1-C10 alkoxy group, but embodiments of the present disclosure are not limited thereto.
R109 in Formula 201 may be selected from:
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.
According to an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:
R101, R111, R112, and R109 in Formula 201A may be understood by referring to the description provided herein.
For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include compounds HT1 to HT20 illustrated below, but are not limited thereto.
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, and for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and for example, about 100 Å to about 1,500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenium oxide; and a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto.
The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied to form the hole injection layer although the deposition or coating conditions may vary according to the compound that is used to form the emission layer.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.
The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
The host may include at least one selected from TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and Compound H51:
In one or more embodiments, the host may further include a compound represented by Formula 301 below.
Ar111 and Ar112 in Formula 301 may each independently be selected from:
a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and
a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.
Ar113 to Ar116 in Formula 301 may each independently be selected from:
a C1-C10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.
g, h, i, and j in Formula 301 may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.
Ar113 to Ar116 in Formula 301 may each independently be selected from:
a C1-C10 alkyl group, the substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, a phenanthrenyl group, and a fluorenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group; and
but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the host may include a compound represented by Formula 302 below:
Ar122 to Ar125 in Formula 302 are the same as described in detail in connection with Ar113 in Formula 301.
Ar126 and Ar127 in Formula 302 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
k and l in Formula 302 may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.
The compound represented by Formula 301 and the compound represented by Formula 302 may include Compounds H1 to H42 illustrated below, but are not limited thereto.
When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stack structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Then, an electron transport region may be disposed on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq but embodiments of the present disclosure are not limited thereto.
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.
The electron transport layer may further include at least one selected from BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ.
In one or more embodiments, the electron transport layer may include at least one of ET1 and ET2, but are not limited thereto:
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2.
The electron transport region may also include an electron injection layer that facilitates injection of electrons from the second electrode 19.
The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li2O, and BaO.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be selected from metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.
Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1.
The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnosis efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy (iso-propoxy) group.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and that has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, 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), the term a C6-C60 arylthio group as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group), and the term “C7-C60 arylalkyl group” as used herein indicates -A104A105 (wherein A104 is the C6-C59 aryl group and A105 is the C1-C53 alkyl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted 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 C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 heteroaryloxy group, the substituted C2-C60 heteroarylthio group, the substituted C3-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), and —P(═O)(Q18)(Q19);
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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), and —P(═O)(Q28)(Q29); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37) and —P(═O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting “substituted” group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group and the carbon atoms (if any) contained in the substituent.
For example, when the term “substituted C1-C30 alkyl” refers to a C1-C30 alkyl group substituted with C6-C30 aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C7-C60.
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was used in place of A.
10 grams (g) (0.035 moles, mol) of 1-bromo-3-iodobenzene and 13.5 g (0.053 mol, 1.5 equivalents, equiv.) of bis(pinacolato)diboron were added to a flask, and 6.9 g (0.071 mol, 2 equiv.) of potassium acetate and 1.44 g (0.05 equiv.) of PdCl2(dppf) were added thereto. Then, 100 milliliters (mL) of toluene was added thereto, and the resultant mixture was refluxed at a temperature of 100° C. overnight. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon to obtain 5.4 g (yield: 54%) of Intermediate A. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C12H16BBrO2: m/z 282.0427, Found: 282.0428.
5.4 g (0.019 mol, 1.2 equiv.) of the synthesized Intermediate A, 2.5 g (0.016 mol, 1 equiv.) of 2-bromopyridine, 1.28 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 4.19 g (0.040 mol, 2.5 equiv.) of sodium carbonate were mixed with 60 mL of a solvent (0.6 molar, M) in which toluene, distilled water (H2O), and ethanol (EtOH) were mixed at a ratio of 3:1:1, and then refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon (while increasing a rate of MC/Hex to between 25% and 50%) to obtain 3 g (yield: 80%) of Intermediate B. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C11H8BrN: m/z 232.9840, Found: 232.9842.
3 g (0.013 mol) of Intermediate B (2-(3-bromophenyl)pyridine) and 4.9 g (0.019 mol, 1.5 equiv.) of bis(pinacolato)diboron were added to a flask, and 2.5 g (0.026 mol, 2 equiv.) of potassium acetate and 0.52 g (0.05 equiv.) of PdCl2(dppf) were added thereto.
Then, 42 mL of toluene was added thereto, and the resultant mixture was refluxed at a temperature of 100° C. overnight. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon to obtain 2.3 g (yield: 63%) of Intermediate C. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C17H20BNO2: m/z 281.1587, Found: 281.1587.
2.3 g (0.008 mol, 1.2 equiv.) of the synthesized Intermediate C, 2.5 g (0.007 mol, 1 equiv.) of Intermediate D (2-(4-bromo-1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)phenol), 0.55 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 2.8 g (0.020 mol, 3 equiv.) of potassium carbonate were mixed with 23 mL of a solvent in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a ratio of 3:1, and then refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography (while increasing a rate of MC/Hex to between 20% and 35%) was performed thereon to obtain 2.2 g (yield: 73%) of Intermediate E. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C29H20N4O: m/z 440.1637, Found: 440.1638.
2.2 g (5 mmol) of Intermediate E and 2.5 g (6 mmol, 1.2 equiv.) of K2PtCl4 were mixed with 25 mL of a solvent in which 20 mL of AcOH and 5 mL of H2O were mixed, and then refluxed for 16 hours. The refluxed mixture thus obtained therefrom was cooled to room temperature, and a precipitate was filtered therefrom. The precipitate was dissolved again in MC and washed by using H2O. Then, column chromatography (MC 40%, EA 1%, Hex 59%) was performed thereon to obtain 1.2 g (purity: 99% or more) of Compound 261. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C29H18N4OPt: m/z 633.1128, Found: 633.1127.
10 g (0.035 mol) of 1-bromo-3-iodobenzene and 13.5 g (0.053 mol, 1.5 equiv.) of bis(pinacolato)diboron were added to a flask, and 6.9 g (0.071 mol, 2 equiv.) of potassium acetate and 1.44 g (0.05 equiv.) of PdCl2(dppf) were added thereto. Then, 100 mL of toluene was added thereto, and the resultant mixture was refluxed at a temperature of 100° C. overnight. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon to obtain 5.4 g (yield: 54%) of Intermediate F. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C12H16BBrO2: m/z 282.0427, Found: 282.0428.
5.4 g (0.019 mol, 1.2 equiv.) of the synthesized Intermediate F, 2.5 g (0.016 mol, 1 equiv.) of 2-bromopyridine, 1.28 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 4.19 g (0.040 mol, 2.5 equiv.) of sodium carbonate were mixed with 60 mL of a solvent (0.6M) in which toluene, distilled water (H2O), and ethanol (EtOH) were mixed at a ratio of 3:1:1, and then refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography (while increasing a rate of MC/Hex to between 25% and 50%) was performed thereon to form 3 g (yield: 80%) of Intermediate G. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C11H8BrN: m/z 232.9840, Found: 232.9842.
3 g (0.013 mol) of Intermediate G (2-(3-bromophenyl)pyridine) and 4.9 g (0.019 mol, 1.5 equiv.) of bis(pinacolato)diboron were added to a flask, and 2.5 g (0.026 mol, 2 equiv.) of potassium acetate and 0.52 g (0.05 equiv.) of PdCl2(dppf) were added thereto. Then, 42 mL of toluene was added thereto, and the resultant mixture was refluxed at a temperature of 100° C. overnight. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon to obtain 2.3 g (yield: 63%) of Intermediate H. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C17H20BNO2: m/z 281.1587, Found: 281.1587.
2.3 g (0.008 mol, 1.2 equiv.) of the synthesized Intermediate C, 2.0 g (0.007 mol, 1 equiv.) of Intermediate J (2-(4-bromo-1-methyl-1H-imidazo[4,5-c]pyridin-2-yl)phenol), 0.53 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 2.7 g (0.020 mol, 3 equiv.) of potassium carbonate were mixed with 22 mL of a solvent in which THF and distilled water (H2O) were mixed at a ratio of 3:1, and then refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. A filtrate obtained therefrom was washed by using EA/H2O, and column chromatography was performed thereon (while increasing a rate of MC/Hex to between 20% and 35%) to obtain 1.7 g (yield: 70%) of Intermediate K. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C24H18N4O: m/z 378.1481, Found: 378.1482.
1.7 g (3.8 mmol) of Intermediate K and 1.9 g (4.6 mmol, 1.2 equiv.) of K2PtCl4 were mixed with 25 mL of a solvent including 20 mL of AcOH and 5 mL of H2O, and then refluxed for 16 hours. The refluxed mixture thus obtained was cooled to room temperature, and a precipitate was filtered therefrom. The precipitate was dissolved again in MC and washed by using H2O. Then, column chromatography (MC 40%, EA 1%, Hex 59%) was performed thereon to obtain 1.0 g (purity: 99% or more) of Compound 241. The obtained product was confirmed by Mass and HPLC analysis.
HRMS (MALDI) calcd for C24H16N4OPt: m/z 571.0972, Found: 571.0973.
Since the organometallic compound has excellent electrical characteristics and thermal stability, an organic light-emitting device including the organometallic compound has excellent driving voltage, luminescent efficiency, power efficiency, color purity, and lifespan characteristics. Also, since the organometallic compound has excellent phosphorescent emission characteristics, a diagnostic composition having high diagnostic efficiency may be provided by using the organometallic compound.
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 of the present description as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2016-0140443 | Oct 2016 | KR | national |
