Patent Application
20220131085
This application claims the benefit of and priority to Korean Patent Application No. 10-2020-0007377, filed on Jan. 20, 2020, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the entire content of which is incorporated herein by reference.
One or more embodiments of the present disclosure relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices (OLEDs) are self-emission devices which produce full-color images. In addition, OLEDs have wide viewing angles and exhibit excellent driving voltage and response speed characteristics.
OLEDs include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including 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 to thereby generate light.
Provided are a novel organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect of an embodiment, an organometallic compound may be represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1,
M may be a transition metal,
L1 may be a ligand represented by Formula 2,
n1 may be 1, 2, or 3, and when n1 is 2 or greater, at least two L1 groups may be identical to or different from each other,
L2 may be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,
n2 may be 0, 1, 2, 3, or 4, and when n2 is 2 or greater, at least two L2 groups may be identical to or different from each other,
L1 may be different from L2,
wherein, in Formula 2,
A21 to A24 may each independently be N or C,
X1 may be O or S,
L13 may be a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
ring CY1 may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R1 to R3 may each independently be hydrogen, deuterium, —F, —C, —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-C60 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q), —P(═O)(Q8)(Q9), or —P(Q)(Q9),
b1 may be an integer from 0 to 20,
b2 may be an integer from 0 to 4,
at least two groups from a plurality of R1 groups may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two groups from a plurality of R2 groups may optionally be bonded together to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R1 and R2 may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R10a may be understood by referring to the description of R1 provided herein,
* and *′ each indicate a bonding site to M in Formula 1, and substituents of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C60 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C60 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
deuterium, —F, —C, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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, C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —C, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; 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 unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group, a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
According to an aspect of another embodiment, an organic light-emitting device may include: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.
The organometallic compound may be included in the emission layer, and the organometallic compound included in the emission layer may serve as a dopant.
According to an aspect of another embodiment, an electronic apparatus may include the organic light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the FIGURE, which is a schematic cross-sectional view of an organic light-emitting device according to one or more exemplary embodiments.
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 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 a cross section illustration that is a schematic illustration of one or more idealized embodiments. As such, variations from the shapes of the illustration 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 figure 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%, or 5% of the stated value.
An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1, M may be a transition metal.
In some embodiments, M may be a first-row transition metal, a second-row transition metal, or a third-row transition metal of periodic table of elements.
In some embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In an embodiment, M may be Ir, Pt, Os, or Rh.
In Formula 1, L1 may be a ligand represented by Formula 2:
Formula 2 may be understood by referring to the description thereof provided herein.
In Formula 1, n1 indicates the number of L1 groups, and n1 may be 1, 2, or 3. When n1 is 2 or greater, at least two L1 groups may be identical to or different from each other. In some embodiments, n1 may be 1 or 2.
L2 in Formula 1 may be any suitable organic ligand. In some embodiments, L2 may be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. L2 may be understood by referring to the description of L2 provided herein.
In Formula 2, n2 indicates the number of L2 groups, and n2 may be 0, 1, 2, 3, or 4. When n2 is 2 or greater, at least two L2 groups may be identical to different from each other. In some embodiments, n2 may be 1 or 2.
In Formula 1, L1 and L2 may be different from each other.
In an embodiment, in Formula 1, M may be Ir or Os, and the sum of n1 and n2 may be 3 or 4, or M may be Pt, and the sum of n1 and n2 may be 2.
In one or more embodiments, in Formula 1, M may be Ir, n1 and n2 may each independently be 1 or 2, and the sum of n1 and n2 may be 3.
In one or more embodiments, in Formula 1, M may be Ir, n1 may be 3, and n2 may be 0. In this embodiment, three L1 groups may be identical to one another.
In Formula 2, A21 to A24 may each independently be N or C. In some embodiments, A21 to A24 may each be C.
In Formula 2, X1 may be O or S.
In Formula 2, L13 may be a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
In some embodiments, L13 in Formula 2 may be:
a single bond; or
a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole 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, each independently unsubstituted or substituted with at least one R10a.
In an embodiment, L13 in Formula 2 may be:
a single bond; or
a benzene group, a naphthalene group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group, each unsubstituted or substituted with at least one R10a.
In Formula 2, ring CY1 may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In some embodiments, in Formula 2, ring CY1 may be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed with each other, iv) a condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,
wherein the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole 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 iso-thiadiazole 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, or a triazasilole group, and
the second ring may be an adamantane group, a norbornane group (a bicyclo[2.2.1]heptane group), a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane 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 an embodiment, in Formula 2, ring CY1 may be i) the first ring or ii) the second ring.
In one or more embodiments, in Formula 2, ring CY1 may be a condensed ring in which at least two rings are condensed with each other.
In some embodiments, in Formula 2, ring CY1 may be iii) a condensed ring in which at least two first rings are condensed with each other, iv) a condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other.
In some embodiments, in Formula 2, ring CY1 may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane 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 pyrrole group, borole group, a phosphole group, a cyclopentadiene group, a silole group, a germole group, a thiophene group, a selenophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an azaborole group, an azaphosphole group, an azacyclopentadiene group, an azasilole group, an azagermole group, an azaselenophene group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In one or more embodiments, in Formula 2, ring CY1 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group.
In Formula 2, R1 to R3 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 (e.g., a substituted or unsubstituted C2-C10 heterocycloalkenyl group), a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-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), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 may respectively be understood by referring to the descriptions of Q1 to Q9 provided herein.
In some embodiments, in Formula 2, R1 to R3 may each independently be: hydrogen, deuterium, —F, —C, —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, —SF5, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group; a C1-C20 alkyl group, a C2-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof,
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 may each independently be:
deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, —CD2CDH2, —CF3, —CF2H, —CFH2, —CH2CF3, —CH2CF2H, —CH2CFH2, —CHFCH3, —CHFCF2H, —CHFCFH2, —CHFCF3, —CF2CF3, —CF2CF2H, or —CF2CFH2; or
an n-propyl group, an iso-propyl 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, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a C1-C60 alkyl group, a phenyl group, or a combination thereof.
In some embodiments, in Formula 2, R1 to R3 may each independently be hydrogen, deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C1-C60 alkoxy group, a C1-C10 alkylthio group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-236, a group represented by one of Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-130, a group represented by one of Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-358, a group represented by one of Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 may respectively be understood by referring to the descriptions of Q3 to Q5 provided herein:
In Formulae 9-1 to 9-39, 9-201 to 9-236, 10-1 to 10-130, and 10-201 to 10-358, * indicates a bonding site to an adjacent atom, “Ph” represents a phenyl group, “TMS” and “SiMe3” each represent a trimethylsilyl group, and “TMG” and “GeMe3” each represent a trimethylgermyl group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-236 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 9-701 to 710:
The “group represented by one of Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with a deuterium” and the “group represented by one of Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 10-501 to 553:
The “group represented by one of Formulae 10-1 to 10-130 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-358 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 10-601 to 617:
In some embodiments, in Formula 2,
R2 may be hydrogen, deuterium, —F, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5),
R3 may be a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C60 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or
a combination thereof.
In Formula 2, b1 indicates the number of R1 groups, and b1 may be an integer from 0 to 20. When b1 is an integer of 2 or greater, at least two R1 groups may be identical to or different from each other. In some embodiments, b1 may be an integer from 0 to 10.
In Formula 2, b2 indicates the number of R2 groups, and b2 may be an integer from 0 to 4. When b2 is 2 or greater, at least two R2 groups may be identical to different from each other. In some embodiments, b2 may be 0, 1, or 2.
In an embodiment, a group represented by
in Formula 2 may be represented by one of Formulae 2(1) to 2(31):
wherein, in Formulae 2(1) to 2(31),
X1 may be understood by referring to the description of X1 provided herein,
* indicates a bonding site to M in Formula 1, and
*″ indicates a bonding site to an adjacent carbon atom.
In one or more embodiments, a group represented by
in Formula 2 may be represented by one of Formulae 2-1 to 2-57:
wherein, in Formulae 2-1 to 2-57,
X1 may be understood by referring to the description of X1 provided herein,
R11 to R16 may each be understood by referring to the description of R1 provided herein, wherein R11 to R16 may each not be hydrogen,
* indicates a bonding site to M in Formula 1, and
*″ indicates a bonding site to an adjacent carbon atom.
In some embodiments, L2 in Formula 1 may be a bidentate ligand each bonded to M in Formula 1 via O, S, Se, N, C, P, Si, As, or a combination thereof.
In some embodiments, L2 in Formula 1 may be a bidentate ligand each bonded to M in Formula 1 via N and C or a bidentate ligand each bonded to M in Formula 1 via two O atoms.
In one or more embodiments, L2 in Formula 1 may be a group represented by one of Formulae 3A to 3F:
wherein, in Formulae 3A to 3F,
Y13 may be O, N, N(Z1), P(Z1)(Z2), or As(Z1)(Z2),
Y14 may be O, N, N(Z3), P(Z3)(Z4), or As(Z3)(Z4),
T11 may be a single bond, a double bond, *—C(Z11)(Z12)—*′, *—C(Z11)═C(Z12)—*′, *═C(Z11)—*′, *—C(Z11)=*′, *═C(Z11)—C(Z12)═C(Z13)—*′, *—C(Z11)═C(Z12)—C(Z13)=*′, *—N(Z11)—*′, or a C5-C30 carbocyclic group unsubstituted or substituted with at least one Z11,
a11 may be an integer from 1 to 10, and when a11 is 2 or greater, at least two T11 groups may be identical to or different from each other,
Y11 and Y12 may each independently be C or N,
T21 may be a single bond, a double bond, O, S, C(Z11)(Z12), Si(Z11)(Z12), or N(Z11),
ring CY11 and ring CY12 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
A1 may be P or As,
Z1 to Z4 and Z11 to Z13 may each be understood by referring to the descriptions of R1 provided herein,
d1 and d2 may each independently be an integer from 0 to 20, and
* and *′ each indicate a bonding site to M in Formula 1.
In some embodiments, a group represented by
in Formula 3D may be represented by one of Formulae CY11-1 to CY11-34, and/(or),
a group represented by
in Formulae 3C and 3D may be represented by one of Formulae CY12-1 to CY12-34:
wherein, in Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34,
X31 may be O, S, N(Z11), C(Z11)(Z12), or Si(Z11)(Z12),
X41 may be O, S, N(Z21), C(Z21)(Z22), or Si(Z21)(Z22),
Y11, Y12, Z1, and Z2 may respectively be understood by referring to the descriptions of Y11, Y12, Z1, and Z2 provided herein,
Z11 to Z18 and Z21 to Z28 may each be understood by referring to the descriptions of R1 provided herein,
d12 and d22 may each independently be an integer from 0 to 2,
d13 and d23 may each independently be an integer from 0 to 3,
d14 and d24 may each independently be an integer from 0 to 4,
d15 and d25 may each independently be an integer from 0 to 5,
d16 and d26 may each independently be an integer from 0 to 6,
in the Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34, * and *′ each indicate a bonding site to M in Formula 1, and *″ indicates a bonding site to an adjacent atom in Formula 3C or T21 in Formula 3D.
In one or more embodiments, L2 in Formula 1 may be a ligand represented by Formula 3D, and at least one of Z1 and Z2 in Formula 3D may each independently be deuterium; —Si(Q3)(Q4)(Q5); —Ge(Q3)(Q4)(Q5); or a C1-C60 alkyl group substituted with at least one deuterium.
In one or more embodiments, L2 in Formula 1 may be a ligand represented by one of Formulae 3-1 and 3-101 to 3-112:
wherein, in Formulae 3-1 and 3-101 to 3-112,
Y11, Y12, ring CY12, Z1 to Z4, Z11 to Z13, and d2 may respectively be understood by referring to the descriptions of Y11, Y12, ring CY12, Z1 to Z4, Z11 to Z13, and d2 provided herein,
Z14 may be understood by referring to the descriptions for Z1 provided herein,
e2 may be an integer from 0 to 2,
e3 may be an integer from 0 to 3,
e4 may be an integer from 0 to 4, and
* and *′ each indicate a bonding site to M in Formula 1.
In some embodiments, in Formula 3-1, Y11 may be N, and Y12 may be C.
In some embodiments, Z12 in Formula 3-1 may be —Si(Q3)(Q4)(Q5); —Ge(Q3)(Q4)(Q); or a C1-C10 alkyl group substituted with at least one deuterium.
In some embodiments, Z12 in Formula 3-1 may be —Si(Q3)(Q4)(Q) or —Ge(Q3)(Q4)(Q), and Z13 may not be hydrogen and a methyl group.
In some embodiments, a group represented by
in Formula 3-1 may be represented by one of Formulae 3-1-1 to 3-1-16, and/(or)
a group represented by
in Formula 3-1 may be represented by one of Formulae 3-1(1) to 3-1(16):
wherein, in Formulae 3-1-1 to 3-1-16 and 3-1(1) to 3-1(16),
Z11 to Z14 may respectively be understood by referring to the descriptions of Z11 to Z14 provided herein, Z21 to Z24 may each be understood by referring to the descriptions of Z2 provided herein, wherein Z11 to Z14 and Z21 to Z24 may not each be hydrogen,
* and *′ each indicate a bonding site to M in Formula 1, and
*″ indicates a bonding site to an adjacent atom.
In Formula 2, i) at least two groups from a plurality of R1 groups may optionally be bonded to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, ii) at least two groups from a plurality of R2 groups may optionally be bonded to from a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, and iii) R1 and R2 may optionally be bonded to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
R10a as used herein may be understood by referring to the description of R1 provided herein.
In Formula 2, * and *′ each indicate a bonding site to M in Formula 1.
In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.
In some embodiments, L1 in Formula 1 may include at least one deuterium.
In some embodiments, in Formula 1, n2 may not be 0, and L2 may include at least one deuterium.
In some embodiments, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 2023:
The group L1 in the organometallic compound represented by Formula 1 may be a ligand represented by Formula 2, and n1, i.e., the number of L1 groups, may be 1, 2, or 3. That is, the organometallic compound may essentially include at least one ligand represented by Formula 2, as a ligand bonded to metal M.
In the ligand represented by Formula 2, ring A may be a condensed ring in which a 6-membered ring is condensed with an imidazole ring, and ring B may be a condensed ring in which ring CY1 is condensed with a 5-membered ring including X1 (see Formula 2′ below). By including ring A having excellent stability and ring B having a long conjugation length, the organometallic compound represented by Formula 1 may have improved stability, and the organometallic compound represented by Formula 1 may have relatively small full widths at half maximum (FWHM) of emission peaks of a photoluminescence (PL) spectrum and/or electroluminescence (EL) spectrum. Thus, an electronic device, e.g., an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved lifespan.
The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, Si energy level, and T1 energy level of some of the organometallic compounds represented by Formula 1 were evaluated by using Gaussian 09 program that performs molecular structure optimizations according to density functional theory (DFT) at a degree of B3LYP. The results thereof are shown in Table 1.
Referring to the results shown in Table 1, the organometallic compound represented by Formula 1 was found to have suitable electrical characteristics for use as a dopant in an electronic device, e.g., an organic light-emitting device.
A method of synthesizing the organometallic compound represented by Formula 1 may be apparent to one of ordinary skill in the art by referring to Synthesis Examples provided herein.
The organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, e.g., as a dopant in the organic layer. Thus, according to another aspect, there is provided an organic light-emitting device that may include a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.
Since the organic light-emitting device has an organic layer including the organometallic compound represented by Formula 1, the organic light-emitting device may have a low driving voltage, high external quantum efficiency, and a low roll-off ratio.
The organometallic compound represented by 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 embodiment, the organometallic compound may serve as a dopant and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 may be smaller than that of the host). The emission layer may emit red light or green light.
As used herein, the expression the “(organic layer) includes at least one organometallic compound” may be construed as meaning the “(organic layer) may include one organometallic compound of Formula 1 or two different organometallic compounds of Formula 1”.
For example, Compound 1 may only be included in the organic layer as an organometallic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In some embodiments, Compounds 1 and 2 may be included in the organic layer as organometallic compounds. In this embodiment, Compounds 1 and 2 may both be included in the same layer (for example, both Compounds 1 and 2 may be included in the 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. In some embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region 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 may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term “organic layer” as used herein refers to a single and/or a plurality of layers disposed between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes including metals.
The FIGURE illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, a structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device will be described with reference to the FIGURE. The organic light-emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially layered in this stated order.
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 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 a material with a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In some embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO.
The organic layer 15 may be 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 a combination thereof.
The hole transport region may include a hole injection layer only or a hole transport layer only. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer which are sequentially stacked on the first electrode 11. In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer, which are sequentially stacked on the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum-deposition, for example, the vacuum deposition may be performed at a temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10-3 torr, and at a rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer.
When a hole injection layer is formed by spin coating, the spin coating may be performed at a rate in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a temperature in a range of about 80° C. to 200° C. to facilitate removal of a solvent after the spin coating, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer.
The conditions for forming a hole transport layer and an electron blocking layer may be inferred from the conditions for forming the hole injection layer.
The hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor-sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof:
In Formula 201, Ar101 and Ar102 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
In Formula 201, xa and xb may each independently be an integer from 0 to 5. In some embodiments, xa and xb may each independently be an integer from 0 to 2. In some embodiments, xa may be 1, and xb may be 0.
In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be: hydrogen, deuterium, —F, —C, —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 (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, or a hexyl group), or a C1-C10 alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group);
a C1-C10 alkyl group or a C1-C10 alkoxy group, each substituted with deuterium, —F, —C, —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, or a combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, or a combination thereof.
In Formula 201, R109 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A:
wherein, in Formula 201A, R101, R111, R112, and R109 may respectively be understood by referring to the descriptions of R101, R111, R112, and R109 provided herein.
In some embodiments, the hole transport region may include at least one of Compounds HT1 to HT20:
The thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.
The charge generating material may include, for example, a p-dopant. The p-dopant may include one of a quinone derivative, a metal oxide, and a compound containing a cyano group. For example, non-limiting examples of the p-dopant include a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a compound containing a cyano group, such as Compound HT-D1:
The hole transport region may further include a buffer layer.
The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.
When the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include the material for forming a hole transport region, the host material described herein, or a combination thereof. In some embodiments, when the hole transport region includes an electron blocking layer, mCP described herein may be used for forming the electron blocking layer.
An emission layer may be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, vacuum deposition and coating conditions for forming the emission layer may be generally similar to those conditions for forming a hole injection layer, though the conditions may vary depending on a compound that is used.
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 TPBi, TBADN, ADN (also known as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or a combination thereof:
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In some embodiments, the emission layer may have a structure in which the red emission layer, the green emission layer, and/or the blue emission layer are layered to emit white light. In some embodiments, the structure of the emission layer may vary.
When the emission layer includes the host and the dopant, an amount of the dopant may be in a range of about 0.01 parts to about 15 parts by weight based on about 100 parts by weight of the host.
The dopant may be the organometallic compound represented by Formula 1 described herein. In some embodiments, the dopant may be a green phosphorescent dopant.
The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
An electron transport region may be over the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
In some embodiments, the electron transport region may have a hole blocking layer/an electron transport layer/an electron injection layer structure or an electron transport layer/an electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
The conditions for forming a hole blocking layer, an electron transport layer, and an electron injection layer may be inferred based on the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, BPhen, BAlq or a combination thereof:
The thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include BCP, BPhen, Alq3, BAq, TAZ, NTAZ, or a combination thereof:
In some embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25:
The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include a material containing metal, in addition to the materials described above.
The material containing metal may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (LiQ) or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.
The electron injection layer may include LiF, NaCl, CsF, Li2, BaO, or a combination thereof.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a material with a relatively low work function, such as a metal, an alloy, an electrically conductive compound, or a mixture thereof. Examples of the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In some embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top emission light-emitting device. In some embodiments, the material for forming the second electrode 19 may vary.
Hereinbefore the organic light-emitting device 10 has been described with reference to the FIGURE, but embodiments are not limited thereto.
According to an aspect of another embodiment, an electronic apparatus including the organic light-emitting device may be provided. The electronic apparatus may be used for various purposes such as a display, lighting, and a mobile phone.
According to an aspect of still another embodiment, a diagnostic composition may include at least one organometallic compound represented by Formula 1.
Since the organometallic compound represented by Formula 1 provides high luminescence efficiency, the diagnostic efficiency of the diagnostic composition that includes the organometallic compound represented by Formula 1 may be excellent.
The diagnostic composition may be applied in various ways, such as in a diagnostic kit, a diagnostic reagent, a biosensor, or 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. The term “C1-C60 alkylene group” as used herein 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 as used herein may include a methyl group, an ethyl group, an n-propyl group, an iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl 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 iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, or a combination thereof. In some embodiments, Formula 9-33 may be a branched C alkyl group. Formula 9-33 may be a tert-butyl group substituted with two methyl groups.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is a C1-C60 alkyl group).
Examples of the C1-C60 alkoxy group, the C1-C20 alkoxy group, or the C1-C10 alkoxy group as used herein may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.
The term “C2-C60 alkenyl group” as used herein refers to a group formed by placing at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group. 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 group formed by placing at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group. 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 cyclic saturated hydrocarbon group including 3 to 10 carbon atoms. 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 as used herein may include 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, or a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom that can be N, O, P, Si, Se, Ge, B, or S as a ring-forming atom and 1 to 10 carbon atoms. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group as used herein may include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, or a tetrahydrothiophenyl 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 its ring, wherein the molecular structure as a whole is non-aromatic. 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 including at least one heteroatom that is N, O, P, Si, Se, Ge, B, or S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl 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. The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include a plurality of rings, the plurality of rings may be fused to each other.
The term “C7-C60 alkylaryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom that is N, O, P, Si, Se, Ge, B, or 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 having at least one heteroatom that is N, O, P, Si, Se, Ge, B, or S as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include a plurality of rings, the plurality of rings may be fused to each other.
The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein is represented by —OA102 (wherein A102 is the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein is represented by —SA103 (wherein A103 is the C6-C60 aryl group). The term “C1-C60 alkylthio group” as used herein is represented by —SA104 (wherein A104 is the C1-C60 alkyl group).
The term “C1-C60 heteroaryloxy group” as used herein refers to —OA106 (wherein A106 is the C1-C60 heteroaryl group), the term “C1-C60 heteroarylthio group” as used herein indicates —SA107 (wherein A107 is the C1-C60 heteroaryl group), and the term “C2-C60 heteroarylalkyl group” as used herein refers to -A106A109 (A109 is a C1-C59 heteroaryl group, and A108 is a C1-C59 alkylene group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and only carbon atoms (e.g., the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. 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 substantially 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 that has two or more condensed rings and a heteroatom that is N, O, P, Si, Se, Ge, B, or S and carbon atoms (e.g., the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. 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 substantially 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 including 5 to 30 carbon atoms only as ring-forming atoms. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a)” may include an adamantane group, a norbornene group, a norbornane group (a bicyclo[2.2.1]heptane group), a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silole group, or a fluorene group, each (unsubstituted or substituted with at least one R10a).
The term “C1-C30 heterocyclic group” as used herein refers to saturated or unsaturated cyclic group including 1 to 30 carbon atoms and at least one heteroatom that is N, O, P, Si, Se, Ge, B, or S as ring-forming atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a)” may include a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene 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 dibenzoselenophenegroup, 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-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R10a).
The “deuterated C1-C60 alkyl group (or, deuterated C1-C20 alkyl group, deuterated C2-C20 alkyl group, or the like)” as used herein refers to a C1-C60 alkyl group substituted with at least one deuterium (or, a C1-C20 alkyl group substituted with at least one deuterium, a C2-C20 alkyl group substituted with at least one deuterium, or the like). Examples of the “deuterated C1 alkyl group (e.g., a deuterated a methyl group)” include —CD3, —CD2H, and —CDH2.
The “deuterated C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one deuterium. Examples of the “deuterated C3-C10 cycloalkyl group” include Formula 10-501.
The “fluorinated C1-C60 alkyl group (or fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group”, and “fluorinated phenyl group” as used herein may respectively be a C1-C60 alkyl group (or C1-C20 alkyl group or the like), C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). Examples of the “fluorinated C1 alkyl group (i.e., a fluorinated methyl group)” may include —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, or “fluorinated C1-C60 heterocycloalkyl group” may respectively be: i) a fully fluorinated C1-C60 alkyl group (or fully fluorinated C1-C20 alkyl group or the like), fully fluorinated C3-C10 cycloalkyl group, or fully fluorinated C1-C60 heterocycloalkyl group, in which all hydrogen atoms are substituted with fluoro groups; or ii) a partially fluorinated C1-C60 alkyl group (or partially fluorinated C1-C20 alkyl group or the like), partially fluorinated C3-C10 cycloalkyl group, or partially fluorinated C1-C60 heterocycloalkyl group, in which some of hydrogen atoms are substituted with fluoro groups.
The “(C1-C20 alkyl)‘X’ group” refers to a ‘X’ group substituted with at least one C1-C20 alkyl group. For example, The “(C1-C20 alkyl)C3-C60 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. Examples of the (C1 alkyl)phenyl group may include a toluyl group.
As used herein, “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” each refer to a heterocyclic ring in which at least one ring-forming carbon atom is replaced with a nitrogen atom and respectively having an identical backbone as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group”.
At least one substitutent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alklythio 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 C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
deuterium, —F, —C, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an 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 C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —S(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an 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 C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group,
—N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof.
In the formulae of the present disclosure, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; 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-C60 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group, a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a C2-C60 heteroarylalkyl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
Hereinafter, an exemplary compound and an exemplary organic light-emitting device according to one or more embodiments will be described in detail with reference to Synthesis Examples and Examples. However, the present disclosure is not limited thereto. The wording “compound B was used instead of compound A” used in describing Synthesis Examples means that an amount of compound B used was identical to an amount of compound A used based on molar equivalence, wherein components A and B are not the same.
The synthesis of Compound 1 is shown in Scheme 1.
10 grams (g) (35.33 millimoles, mmol) of Compound 1-1 and 6.17 g (17.50 mmol) of iridium chloride were mixed with 90 milliliters (mL) of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred under reflux for 24 hours, and then the temperature was dropped to room temperature. A solid was formed therefrom and separated by filtration. The solid was sufficiently washed with water, methanol, and hexane in this stated order and dried in a vacuum oven to thereby obtain 11.5 g of Compound 1-2 (83%).
45 mL of methylene chloride (MC) was mixed with 5.00 g (3.16 mmol) of Compound 1-2, and a mixture of 1.70 g (6.62 mmol) of silver triflate (AgOTf) and 15 mL of methanol was added thereto. Then, the mixture was stirred for about 18 hours at room temperature while blocking light by using an aluminum foil. The resultant was filtered using diatomaceous earth to remove a solid formed therefrom and filtered under reduced pressure to thereby obtain a solid (Compound 1-3). The solid was used in the following reaction without any further purification.
10 g (23.07 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole), 6.33 g (23.07 mmol) of 4,4,5,5-tetramethyl-2-(5-methylbenzo[b]thiophen-3-yl)-1,3,2-dioxaborolane, 0.80 g (0.69 mmol) of Pd(PPh3)4, and 15.94 g (117.27 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using ethyl acetate (EA) and hexane at a ratio of 1:3 to thereby obtain 10.51 g of Compound 1-4 (91%).
5.00 g (5.15 mmol) of Compound 1-3 and 2.84 g (5.67 mmol) of Compound 1-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 2.20 g of Compound 1 (31%). The resulting compound was identified by using mass spectroscopy and high-performance liquid chromatography (HPLC) analysis. HRMS(MALDI) calculated for C70H79IrN4SSi2: m/z 1256.5193, Found: 1256.5198.
The synthesis of Compound 2 is shown in Scheme 2.
10 g (23.07 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole), 3.74 g (23.07 mmol) of benzofuran-3-ylboronic acid, 0.80 g (0.69 mmol) of Pd(PPh3)4, and 15.94 g (117.27 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using EA and hexane at a ratio of 1:3 to thereby obtain 8.69 g of Compound 2-4 (80%).
3.00 g (3.09 mmol) of Compound 1-3 and 1.60 g (3.40 mmol) of Compound 2-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 1.06 g of Compound 2 (28%). The resulting compound was identified by using mass spectroscopy and high-performance liquid chromatography (HPLC) analysis. HRMS(MALDI) calcd. for C69H77IrN4OSi2: m/z 1226.5265, Found: 1226.5269.
The synthesis of Compound 3 is shown in Scheme 3.
5 g (11.54 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole), 2.93 g (11.54 mmol) of 5-phenylbenzothiophene-3-ylboronic acid, 0.40 g (0.35 mmol) of Pd(PPh3)4, and 7.97 g (58.63 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using EA and hexane at a ratio of 1:3 to thereby obtain 5.46 g of Compound 3-4 (84%).
2.20 g (2.27 mmol) of Compound 1-3 and 1.41 g (2.50 mmol) of Compound 3-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 0.87 g of Compound 3 (29%). The resulting compound was identified by using mass spectroscopy and high-performance liquid chromatography (HPLC) analysis. HRMS(MALDI) calcd. for C75H81IrN4SSi2: m/z 1318.5350, Found: 1318.5352.
The synthesis of Compound 4 is shown in Scheme 4.
6.32 g (14.59 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole), 3.80 g (14.59 mmol) of 2-(benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.42 g (0.36 mmol) of Pd(PPh3)4, and 10.08 g (72.95 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using EA and hexane at a ratio of 1:3 to thereby obtain 5.33 g of Compound 4-4 (75%).
1.50 g (1.55 mmol) of Compound 1-3 and 0.75 g (1.55 mmol) of Compound 4-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 0.40 g of Compound 4 (21%). The resulting compound was identified by using mass spectroscopy and HPLC analysis. HRMS (MALDI) calcd. for C69H77IrN4SSi2: m/z 1242.5037, Found: 1242.5041.
The synthesis of Compound 5 is shown in Scheme 5.
3.00 g (6.92 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole), 1.22 g (6.92 mmol) of (5-methylbenzofuran-3-yl)boronic acid, 0.16 g (0.14 mmol) of Pd(PPh3)4, and 4.78 g (34.60 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using EA and hexane at a ratio of 1:3 to thereby obtain 2.92 g of Compound 5-4 (87%).
2.00 g (2.06 mmol) of Compound 1-3 and 1.10 g (2.27 mmol) of Compound 5-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 0.89 g of Compound 5 (35%). The resulting compound was identified by using mass spectroscopy and HPLC analysis. HRMS (MALDI) calcd. for C70H79IrN4OSi2: m/z 1240.5422, Found: 1240.5422.
The synthesis of Compound 821 is shown in Scheme 6.
10 g (52.83 mmol) of Compound 821-1 (5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridine) and 8.47 g (24.01 mmol) of iridium chloride were mixed with 90 mL of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred under reflux for 24 hours to carry out the reaction, and then the temperature was dropped to room temperature. A solid was formed therefrom and separated by filtration. The solid was sufficiently washed with water, methanol, and hexane in this stated order and dried in a vacuum oven to thereby obtain 12.04 g of Compound 821-2 (83%).
45 mL of MC was mixed with 3.00 g (2.48 mmol) of Compound 821-2, and a solution, in which 1.40 g (5.46 mmol) of AgOTf is dissolved in 15 mL of methanol, was added thereto. Then, the mixture was stirred for about 18 hours to carry out a reaction at room temperature while blocking light by using an aluminum foil. The resultant was filtered using diatomaceous earth to remove a solid formed therefrom and filtered under reduced pressure to thereby obtain a solid (Compound 821-3). The solid was used in the following reaction without any further purification.
3 g (10.98 mmol) of 2-bromo-1-phenyl-1H-benzo[d]imidazole, 2.33 g (10.98 mmol) of 4-naphtho[2,1-b]furan-1-ylboronic acid, 0.25 g (0.22 mmol) of Pd(PPh3)4, and 7.59 g (54.90 mmol) of K2CO3 were mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. Then, the mixture was stirred for 18 hours under reflux. Once the temperature was dropped to room temperature, an organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer. The resultant was filtered, and the solvent in the resulting filtrate was removed under reduced pressure. The residual was purified through column chromatography using EA and hexane at a ratio of 1:3 to thereby obtain 2.57 g of Compound 821-4 (65%).
3 g (2.56 mmol) of Compound 821-3 and 1.02 g (2.82 mmol) of Compound 821-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 0.74 g of Compound 821 (31%). The resulting compound was identified by using mass spectroscopy and HPLC analysis. HRMS (MALDI) calcd. for C51H27D12IrN4O: m/z 928.3506, Found: 928.3504.
The synthesis of Compound 822 is shown in Scheme 7.
5 g (32.22 mmol) of Compound 822-1 (2-phenylpyridine) and 5.17 g (14.65 mmol) of iridium chloride were mixed with 90 mL of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred while refluxing for about 24 hours to carry out a reaction, and then the temperature was dropped to room temperature. A solid was formed therefrom and separated by filtration. The solid was sufficiently washed with water, methanol, and hexane in this stated order and dried in a vacuum oven to thereby obtain 5.50 g of Compound 822-2 (70%).
45 mL of MC was mixed with 3.00 g (2.80 mmol) of Compound 822-2, and a solution, in which 1.29 g (5.02 mmol) of AgOTf is dissolved in 15 mL of methanol, was added thereto. Then, the mixture was stirred for about 18 hours to carry out a reaction at room temperature while blocking light by using an aluminum foil. The resultant was filtered using diatomaceous earth to remove a solid formed therefrom and filtered under reduced pressure to thereby obtain a solid (Compound 822-3). The solid was used in the following reaction without any further purification.
2 g (2.80 mmol) of Compound 822-3 and 1.45 g (3.08 mmol) of Compound 2-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. Then, the mixture was stirred under reflux for 18 hours at 120° C. to carry out the reaction. Then, the temperature was dropped. The resulting mixture was filtered to obtain a solid. Then, the solid was sufficiently washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane at a ratio of 1:50 to thereby obtain 0.54 g of Compound 822 (20%). The resulting compound was identified by using mass spectroscopy and HPLC analysis. HRMS (MALDI) calcd. for C55H45IrN4O: m/z 970.3223, Found: 970.3227.
The synthesis of Compound 767 is shown in Scheme 8.
5 g (9.99 mmol) of Compound 1-4 and 1.76 g (5.00 mmol) of iridium chloride were mixed with 90 mL of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred under reflux for 24 hours to carry out the reaction, and then the temperature was dropped to room temperature. A solid was formed therefrom and separated by filtration. The solid was sufficiently washed with water, methanol, and hexane in this stated order and dried in a vacuum oven to thereby obtain 4.91 g of Compound 767-2(80%).
4 g (1.63 mmol) of Compound 767-2 and 1.80 g (18 mmol) of acetylacetone, and 2.49 g (18 mmol) of K2CO3 were added to 60 mL of 2-ethoxyethanol, followed by stirring at room temperature for 24 hours. The resulting solid product was removed therefrom by filtration, followed by performing column chromatography using ethyl acetate and hexane to thereby obtain 0.63 g of Compound 767 (30%). The resulting compound was identified by using mass spectroscopy and HPLC analysis. HRMS (MALDI) calcd. for C73H71IrN4O2S2: m/z 1292.4648, Found: 1292.4644.
A glass substrate, on which ITO is patterned as an anode, was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated in isopropyl alcohol and water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Subsequently, the glass substrate was mounted on a vacuum-deposition device.
Compound HT3 and Compound F6-TCNNQ were co-vacuum-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å. Compound HT3 was then vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.
Subsequently, Compound CBP (as a host) and Compound 1 (as a dopant) were co-deposited on the hole transport layer at a weight ratio of 95:5 to form an emission layer having a thickness of 400 Å.
Compound ET3 and Compound ET-D1 were co-deposited at a volume ratio of 50:50 on the emission layer to form an electron transport layer having a thickness of 350 Å, Compound ET-D1 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 cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of Compound 1 as a dopant in the formation of an emission layer.
The driving voltage (V), the maximum external quantum efficiency (Max EQE, %), and the roll-off ratio (%) of the organic light-emitting devices manufactured in Examples 1 to 7 and Comparative Example A were evaluated. The evaluation results are shown in Table 2. A Keithley 2400 current voltmeter and a luminance meter (Minolta Cs-1000A) were used in evaluation. The roll-off ratio was calculated by Equation 20. The max EQE in Table 2 are shown in relative values (%).
Roll-off ratio={1−(efficiency (at 8,000 nit)/maximum luminescence efficiency)}×100% Equation 20
Referring to Table 2, the organic light-emitting devices of Examples 1 to 7 were found to have improved driving voltage, improved external quantum efficiency, and improved roll-off ratio, as compared with the organic light-emitting device of Comparative Example A.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 3 were used instead of Compound 1 as a dopant in the formation of an emission layer.
The driving voltage (V), the Max EQE (%), and the roll-off ratio (%) of the organic light-emitting devices manufactured in Example 8 and Comparative Example B were evaluated in substantially the same manner as in Evaluation Example 1. The evaluation results are shown in Table 3. The Max EQE in Table 3 are shown in relative values (%).
Referring to Table 3, the organic light-emitting device of Example 8 was found to have improved driving voltage, improved external quantum efficiency, and improved roll-off ratio, as compared with the organic light-emitting device of Comparative Example B.
As apparent from the foregoing description, the organometallic compound may have excellent electrical characteristics, and thus, an electronic device, e.g., an organic light-emitting device, including the organometallic compound may have improved driving voltage, improved external quantum efficiency, and/or improved roll-off ratio characteristics.
It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should be considered as an available feature or aspect of other exemplary 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 |
|---|---|---|---|
| 10-2020-0007377 | Jan 2020 | KR | national |
