Patent Application
20240209012
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0065551, filed on May 27, 2022, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated herein in its entirety by reference.
The disclosure relates to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices (OLEDs) are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.
In an example, a typical organic light-emitting device includes an anode, a cathode, and an organic layer that is located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons may recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.
Aspects are directed to a an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the detailed description that follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments.
According to an aspect, an organometallic compound represented by Formula 1 is provided:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1,
wherein, in Formulae 2-1 and 2-2,
According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organometallic compound represented by Formula 1.
The organometallic compound may be included in an emission layer, and the organometallic compound included in the emission layer may act as a dopant.
According to still another aspect, an electronic apparatus includes the organic light-emitting device described herein.
These and/or other aspects will become apparent and more readily appreciated from the following detailed description of the exemplary embodiments, taken in conjunction with the FIGURE, which is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.
Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing. In this regard, the exemplary embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the exemplary embodiments are merely described in further detail below by referring to the FIGURE, to explain aspects. The term “and/or” used herein 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.
The terminology used herein is for the purpose of describing one or more exemplary 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.
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.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
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.
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.
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within +30%, 20%, 10%, 5% of the stated value.
Hereinafter, a work function or a highest occupied molecular orbital (HOMO) energy level is expressed as an absolute value from a vacuum level. In addition, when the work function or the HOMO energy level is referred to be “deep,” “high” or “large,” the work function or the HOMO energy level has a large absolute value based on “0 electron Volt (eV)” of the vacuum level, while when the work function or the HOMO energy level is referred to be “shallow,” “low,” or “small,” the work function or HOMO energy level has a small absolute value based on “0 eV” of the vacuum level.
An organometallic compound is represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
wherein M in Formula 1 is a transition metal.
For example, M may be a Period 1 transition metal of the Periodic Table of Elements, a Period 2 transition metal of the Periodic Table of Elements, or a Period 3 transition metal of the Periodic Table of Elements.
In one or more embodiments, M may be iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.
In one or more embodiments, M may be iridium, platinum, osmium, or rhodium.
In Formula 1, L1 is a ligand represented by Formula 2-1, and L2 is a ligand represented by Formula 2-2:
wherein, Formulae 2-1 and 2-2 are as described herein.
n1 and n2 in Formula 1 respectively indicate the number of ligands L1 and the number of ligands L2, and n1 and n2 are each independently 1 or 2. When n1 is 2, two L1 are identical to or different from each other, and when n2 is 2, two L2 are identical to or different from each other.
For example, regarding Formula 1, i) n1 may be 2, and n2 may be 1; or ii) n1 may be 1, and n2 may be 2, but embodiments are not limited thereto.
In one or more embodiments, in Formula 1, i) M may be iridium or osmium, and a sum of n1 and n2 may be 3; or ii) M may be platinum, and a sum of n1 and n2 may be 2.
L1 and L2 in Formula 1 are different from each other. Accordingly, the organometallic compound represented by Formula 1 is a heteroleptic complex.
X11 in Formula 2-1 is Ge.
X2 in Formula 2-1 is O, S, Se, N(R29), C(R29a)(R29b), or Si(R29a)(R29b), wherein R29, R29a, and R29b are each as defined herein.
In one or more embodiments, X2 may be O or S.
In Formula 2-1, A1 is C or N, A2 is C or N, A3 is C or N, and A4 is C or N, wherein one of A1 to A4 is C bonded to a neighboring pyridine group, and another of A1 to A4 is C bonded to M in Formula 1.
In one or more embodiments, in Formula 2-1,
In one or more embodiments, a group represented by
of Formula 2-1 may be a group represented by one of Formulae CY2-A to CY2-F:
wherein, in Formulae CY2-A to CY2-F,
Y3 in Formula 2-2 is N.
In Formula 2-2, A31 is C or N, A32 is C or N, A33 is C or N, and A34 is C or N.
In one or more embodiments, each of A31 to A34 may be C.
Y4 in Formula 2-2 is C or N.
In one or more embodiments, Y4 may be C.
In Formulae 2-1 and 2-2, ring CY2 and ring CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein i) ring CY2 is a C3-C30 heterocyclic group including at least one N as a ring-forming atom (for example, including, as a ring-forming moiety, one, two, or three *═N—*′, wherein * and *′ each indicate a binding site to an adjacent atom); ii) at least one of A1 to A4 is N; or iii) ring CY2 is a C3-C60 heterocyclic group including at least one N as a ring-forming atom (for example, including, as a ring-forming moiety, one, two, or three *═N—*′, wherein * and *′ each indicate a binding site to an adjacent atom), and at least one of A1 to A4 is N.
For example, ring CY2 and ring CY4 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring group in which at least two first rings are condensed to each other, iv) a condensed ring group in which at least two second rings are condensed to each other, or v) a condensed ring group in which at least one first ring and at least one second ring are condensed to each other,
In one or more embodiments, ring CY2 and ring CY4 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a naphthobenzothiophene group, a naphthobenzofuran group, a naphthobenzoselenophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, a dinaphthothiophene group, a dinaphthofuran group, a dinaphthoselenophene group, a naphthocarbazole group, a naphthofluorene group, a phenanthrobenzosilole group, a phenanthrobenzothiophene group, a phenanthrobenzofuran group, a phenanthrobenzoselenophene 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-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azadibenzoselenophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzothiophene group, an azanaphthobenzofuran group, an azanaphthobenzoselenophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, an azadinaphthothiophene group, an azadinaphthofuran group, an azadinaphthoselenophene group, an azanaphthocarbazole group, an azanaphthofluorene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzoselenophene 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 phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with an adamantane group, a benzene group that is condensed with a norbornane group, a benzene group that is condensed with a norbornene group, a pyridine group that is condensed with an adamantane group, a pyridine group that is condensed with a norbornane group, or a pyridine group that is condensed with a norbornene group.
In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group.
In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group. In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, or a dibenzoselenophene group, and at least one of A1 to A4 in Formula 2-1 may be N.
In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group, and at least one of A1 to A4 in Formula 2-1 may be N. In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group, and all of A1 to A4 in Formula 2-1 may C.
In one or more embodiments, ring CY4 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group that is condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a naphthobenzothiophene group, a naphthobenzofuran group, a naphthobenzoselenophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, a dinaphthothiophene group, a dinaphthofuran group, a dinaphthoselenophene group, a naphthocarbazole group, a naphthofluorene group, a phenanthrobenzosilole group, a phenanthrobenzothiophene group, a phenanthrobenzofuran group, a phenanthrobenzoselenophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azadibenzoselenophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzothiophene group, an azanaphthobenzofuran group, an azanaphthobenzoselenophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, an azadinaphthothiophene group, an azadinaphthofuran group, an azadinaphthoselenophene group, an azanaphthocarbazole group, an azanaphthofluorene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzofuran group, or an azaphenanthrobenzoselenophene group.
R1 to R4, R14 to R16, R29, R29a, and R29b in Formulae 2-1 and 2-2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C0-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 are each as described herein. R2 represents a substituent group that may be bonded to any one or more of A1 to A4, and/or ring CY2.
In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not be —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 are each as described herein.
In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not include germanium (Ge).
In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not be —Si(Q3)(Q4)(Q5), wherein Q3 to Q5 are each as described herein.
In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not include silicon (Si).
In one or more embodiments, in Formula 2-2, a3 may not be 0, at least one of R3 in the number of a3 may be —Si(Q3)(Q4)(Q5), and each of R1, R2, R4, R14 to R16, R29, R29a, and R29b may not include germanium (Ge) or silicon (Si), wherein Q3 to Q5 are each as described herein.
For example, R1 to R4, R14 to R16, R29, R29a, and R29b may each independently be:
In one or more embodiments, R1 to R4, R29, R29a, and R29b may each independently be:
In one or more embodiments, R14 to R16 may each independently be a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.
In one or more embodiments, R14 to R16 in Formula 2-1 may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, —CD2CH3, or a phenyl group.
In one or more embodiments, R14 to R16 in Formula 2-1 may be identical to or different from each other.
In one or more embodiments, R1 to R4, R14 to R16, R29, R29a, and R29b in Formulae 2-1 and 2-2 may each independently be hydrogen, deuterium, —F, 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, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 are each independently as described herein.
In one or more embodiments, at least one of R1 in the number of a1 in Formula 2-1 (for example, R11 of Formula CY1-1) may be a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F:
In Formulae 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is 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 9-230 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 or 9-601 to 9-637:
wherein, in Formulae 9-501 to 9-514 and 9-601 to 9-637, * indicates a binding site to a neighboring atom.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:
wherein, in Formulae 9-701 to 9-710, * indicates a binding site to a neighboring atom.
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
wherein, in Formulae 10-501 to 10-553, * indicates a binding site to a neighboring atom.
The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-636:
wherein, in Formulae 10-601 to 10-636, * indicates a binding site to a neighboring atom.
a1 to a4 in Formula 2-1 and 2-2 indicate numbers of R1 to R4, respectively, and a1 is an integer from 0 to 3, a2 is an integer from 0 to 6, a3 is an integer from 0 to 4, and a4 is an integer from 1 to 20 (for example, an integer from 0 to 10). When a1 is 2 or greater, two or more of R1 may be identical to or different from each other, when a2 is 2 or greater, two or more of R2 may be identical to or different from each other, when a3 is 2 or greater, two or more of R3 may be identical to or different from each other, and when a4 is 2 or greater, two or more of R4 may be identical to or different from each other. For example, a1 to a4 may each independently be 0, 1, 2, or 3.
In one or more embodiments, in Formula 2-1, R2 may not be hydrogen.
In one or more embodiments, in Formula 2-2, R3 may not be hydrogen.
In one or more embodiments, the organometallic compound may include at least one of deuterium, a fluoro group, or a combination thereof.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition 1 to Condition 8:
In Formulae 2-1 and 2-2, in each of i) two or more of a plurality of R1, ii) two or more of a plurality of R2, iii) two or more of a plurality of R3, iv) two or more of a plurality of R4, and v) two or more of R1 to R4, the two or more may be optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a. That is, i) two or more of a plurality of R1 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, ii) two or more of a plurality of R2 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iii) two or more of a plurality of R3 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iv) two or more of a plurality of R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, and v) two or more of R1 to R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
R10a is as described in connection with R2. For example, R10a may be as described in connection with R2, except that R10a may not be hydrogen.
* and *′ in Formulae 2-1 and 2-2 each indicate a binding site to M in Formula 1.
In one or more embodiments, a group represented by:
in Formula 2-1 may be a group represented by one of Formulae CY1-1 to CY1-6:
wherein, in Formulae CY1-1 to CY1-6,
For example, in one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen.
In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen or a methyl group.
In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen, a methyl group, or a cyano group.
In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen, and R12 and R13 may each be hydrogen.
In one or more embodiments, R1 in Formulae CY1-1 and/or CY1-4 may include two or more carbon atoms, three or more carbon atoms, or four or more carbon atoms.
In one or more embodiments, R1 in Formulae CY1-1 and/or CY1-4 may be:
In one or more embodiments, a group represented by
in Formula 2-1 may be a group represented by one of Formulae CY2-1 to CY2-14:
wherein, in Formulae CY2-1 to CY2-14,
For example, in one or more embodiments
In one or more embodiments, a group represented by
in Formula 2-1 may be a group represented by one of Formulae CY2(1) to CY2(60):
wherein, in Formulae CY2(1) to CY2(60),
In one or more embodiments, a group represented by
in Formula 2-2 may be a group represented by one of Formulae CY3(1) to CY3(16):
wherein, in Formulae CY3(1) to CY3(16),
In one or more embodiments, a group represented by:
in Formula 2-2 may be a group represented by one of Formulae CY4-1 to CY4-21:
wherein, in Formulae CY4-1 to CY4-21,
For example, A41 to A46 in Formulae CY4-16 to CY4-21 may each be C.
In one or more embodiments, A46 in Formulae CY4-16 to CY4-21 may be N.
In one or more embodiments, a group represented by:
in Formula 2-2 may be a group represented by one of Formulae CY4-1 to CY4-16.
In one or more embodiments, a group represented by:
in Formula 2-1 may be substituted with at least one R2, and a group represented by:
may be unsubstituted or substituted with at least one R4, as defined herein.
In one or more embodiments, L1 in Formula 1 may be a ligand represented by one of Formulae B1 to B331:
Each of * and in Formulae 131 to B331 indicates a binding site to M in Formula 1.
In one or more embodiments, L2 in Formula 1 may be a ligand represented by one of Formula A1 to A250:
Each of * and *′ in Formulae A1 to A250 indicates a binding site to M in Formula 1.
In one or more embodiments, the organometallic compound is represented by Formula 1, wherein M in Formula 1 may be iridium, and L1, L2, n1, and n2 may each be as defined for the compounds shown in Tables 1 to 56:
In one or more embodiments, the organometallic compound represented by Formula 1 may emit a red light or a green light, for example, a red light or a green light having a maximum luminescence wavelength of about 500 nanometers (nm) or greater, for example, a maximum luminescence wavelength of about 500 nm to about 750 nm.
For example, the organometallic compound may emit a green light. In one or more embodiments, the organometallic compound may emit a light (for example, a green light) having a maximum emission wavelength of about 515 nm to about 550 nm, or about 520 nm to about 540 nm.
In relation to the organometallic compound represented by Formula 1, L1 is a ligand represented by Formula 2-1, L2 is a ligand represented by Formula 2-2, n1, which is the number of L1, and n2, which is the number of L2, may each independently be 1 or 2. Accordingly, the current efficiency and the lifespan of an electronic device, such as, an organic light-emitting device, including at least one organometallic compound represented by Formula 1, may be improved.
A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, and a triplet (Ti) energy level of some compounds of the organometallic compound represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimization obtained at the B3LYP level, and results thereof are shown in Table 57. The energy levels are expressed in electron volts (eV).
From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.
Accordingly, the organometallic compound represented by Formula 1 is suitable for use as a material for an organic layer of organic light-emitting device, for example, a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and the organic layer includes at least one organometallic compound represented by Formula 1.
The organic light-emitting device includes an organic layer containing at least one organometallic compound represented by Formula 1. Accordingly, the organic light-emitting device may have improved external quantum efficiency and improved lifespan characteristics.
The organometallic compound of Formula 1 may be used or located between a pair of electrodes of an organic light-emitting device. For example, at least one organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the at least one organometallic compound represented by Formula 1 in the emission layer is less than an amount of the host in the emission layer). In other words, in one or more embodiments, an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound represented by Formula 1 in the emission layer, based on the total weight of the emission layer.
The emission layer may emit a red or a green light, for example, a red light or a green light having a maximum luminescence wavelength of about 500 nanometers (nm) or greater, for example, a maximum luminescence wavelength of about 500 nm to about 750 nm. For example, the organometallic compound may emit a green light. In one or more embodiments, the emission layer (or an organic light-emitting device) may emit a light (for example, a green light) having a maximum emission wavelength of about 515 nm to about 550 nm, or about 520 nm to about 540 nm.
The expression “(an organic layer) includes at least one organometallic compound represented by Formula 1” used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1, and a case in which “(an organic layer) includes two or more different organometallic compounds each represented by Formula 1.
For example, the organic layer may include, as the at least one organometallic compound represented by Formula 1, only Compound 1. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the at least one organometallic compound represented by Formula 1, Compound 1 and Compound 2, wherein Compound 1 and Compound 2 are different. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer, and an electron transport region located between the emission layer and the second electrode, and 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 layer and/or a plurality of layers located between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including a metal.
The
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/or water repellency.
The first electrode 11 may be produced 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 materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or the first electrode 11 may have a multi-layered structure including a plurality of layers. For example, in one or more embodiments, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
The organic layer 15 may be located 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 located 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 only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron-blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec.
When the hole injection layer is formed by spin coating, the coating conditions may vary depending on a material for forming the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and heat treatment at about 80° C. to about 200° C. to remove solvent(s) after coating.
The conditions for forming the hole transport layer and the electron-blocking layer may be similar to or the same as the conditions for forming the hole injection layer.
The hole transport region may include at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof, but embodiments are not limited thereto:
Ar101 and Ar102 in Formula 201 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with at least one of 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C1-C60 aryloxy group, a C1-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:
R109 in Formula 201 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with at least one of 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A:
R101, R111, R112, and R109 in Formula 201A are each as described herein.
For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one of Compounds HT1 to HT20, but embodiments are not limited thereto:
A thickness of the hole transport region may be 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 at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. Without wishing to be bound to theory, when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyano group-containing compound, but embodiments are not limited thereto. 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), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), or the like; a metal oxide, such as a tungsten oxide, a molybdenum oxide, or the like; or a cyano group-containing compound, such as Compound HT-D1, but embodiments are not limited thereto.
The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of a light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
Meanwhile, when the hole transport region includes an electron-blocking layer, a material for forming the electron-blocking layer may include a material that is used in the hole transport region as described herein, a host material as described herein, or a combination thereof. For example, when the hole transport region includes an electron-blocking layer, mCP, Compound H-H1, or the like, which will be described herein, may be used as a material for the electron-blocking layer, but embodiments are not limited thereto.
An emission layer may be formed on the hole transport region, for example, by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, although the deposition or coating conditions may vary according to a material that is used to form the emission layer.
The emission layer may include a host and a dopant, and the dopant may include at least one organometallic compound represented by Formula 1.
The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalen-2-yl)anthracene (ADN) (also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-E43, or a combination thereof, but embodiments are not limited thereto:
When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit a white light.
When the emission layer includes both a host and a dopant, an amount (for example, a weight) of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the emission layer.
A thickness of the emission layer may be about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. Without wishing to be bound to theory, when the thickness of the emission layer is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Next, an electron transport region may be located on the emission layer.
The electron transport region may include a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, the electron transport region may have a hole-blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole-blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood, for example, by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole-blocking layer, the hole-blocking layer may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), or a combination thereof, but embodiments are not limited thereto:
A thickness of the hole-blocking layer may be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. Without wishing to be bound to theory, when the thickness of the hole-blocking layer is within these ranges, excellent hole-blocking characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the electron transport layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxy-quinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAIq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or a combination thereof.
In one or more embodiments, the electron transport layer may include one of Compounds ET1 to ET25, or a combination thereof, but embodiments are not limited thereto:
A thickness of the electron transport layer may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Without wishing to be bound to theory, when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.
The electron transport layer may include a metal-containing material in addition to the materials as described herein.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2, but embodiments are not limited thereto:
The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 into the electron transport region.
The electron injection layer may include, for example, LiF, NaCl, CsF, Li2O, BaO, or a combination thereof, but embodiments are not limited thereto.
A thickness of the electron injection layer may be about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. Without wishing to be bound to theory, when the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. Examples of the material for forming the second electrode 19 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device has been described in detail and with reference to the FIGURE, but embodiments are not limited thereto.
According to another aspect, the organic light-emitting device may be included in an electronic apparatus. Thus, an electronic apparatus including the organic light-emitting device is also provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, or the like, but embodiments are not limited thereto.
Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.
The organometallic compound represented by Formula 1 provides a high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have a high diagnostic efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, or the like, but embodiments are not limited thereto.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
Non-limiting examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or the like, each unsubstituted or substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like.
The term “C1-C60 alkylthio group” as used herein refers to a monovalent group represented by —SA102 (wherein A102 is the C1-C60 alkyl group).
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, a butenyl group, or the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethynyl group, a propynyl group, or the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 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.
Non-limiting examples of the C3-C10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C1-C10“heterocycloalkyl group” as used herein refers to a saturated cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Non-limiting examples of the C1-C10 heterocycloalkyl group include a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, or the like.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, or the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring.
Non-limiting examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group. The term “C7-C60 aryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C6-C60 aryl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group that includes a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group that includes a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The term “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 “C2-C60 heteroaryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C1-C60 heteroaryl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA103 (wherein A103 indicates the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein indicates —SA104 (wherein A104 indicates the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group or the like. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described herein.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Non-limiting examples of the C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a) as used herein include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, and a fluorene group (each unsubstituted or substituted with at least one R10a).
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Non-limiting examples of the C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a) may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an 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, a 5,6,7,8-tetrahydroquinoline group, or the like (each unsubstituted or substituted with at least one R10a).
Non-limiting examples of the “C5-C30 carbocyclic group” and the “C1-C30 heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring system in which two or more first rings are condensed with each other, iv) a condensed ring system in which two or more second rings are condensed with each other, or v) a condensed ring system in which at least one first ring is condensed with at least one second ring,
The terms “fluorinated C1-C60 alkyl group” (or a fluorinated C1-C20 alkyl group or the like),” “fluorinated C3-C10 cycloalkyl group,” “fluorinated C1-C10 heterocycloalkyl group,” and “fluorinated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group” (that is, a fluorinated methyl group) includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group” (or, a fluorinated C1-C20 alkyl group, or the like), the “fluorinated C3-C10 cycloalkyl group,” the “fluorinated C1-C10 heterocycloalkyl group,” and the “the fluorinated phenyl group” may respectively be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen atoms included therein are substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen atoms included therein are not substituted with a fluoro group.
The terms “deuterated C1-C60 alkyl group” (or a deuterated C1-C20 alkyl group, or the like), “deuterated C3-C10 cycloalkyl group,” “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group” (that is, the deuterated methyl group) may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” include, for example, Formulae 10-501, 10-502, 10-503, 10-504, or the like. The “deuterated C1-C60 alkyl group” (or, the deuterated C1-C20 alkyl group, or the like), “the “deuterated C3-C10 cycloalkyl group,” “the “deuterated C1-C10 heterocycloalkyl group,” and “the deuterated phenyl group” may respectively be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group, or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen atoms included therein are substituted with deuterium, or ii) a partially deuterated C1-C60 alkyl group (or, a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen atoms included therein are not substituted with deuterium.
The term “(C1-C20 alkyl)‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl)phenyl group may include a toluyl group.
As used herein, the terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” each refers to a hetero ring group 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-fluoren-9-one group, and a dibenzothiophene 5,5-dioxide group, in which, in each group, at least one ring-forming carbon atom is substituted with N.”
As used herein, at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C1-C60 aryloxy group, the substituted C1-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 as described herein may each independently be:
Hereinafter, a compound and an organic light-emitting device according to exemplary embodiments are described in further detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.
Compound A201 (2-phenylpyridine) (7.0 grams (g), 45.1 millimoles (mmol)) and iridium chloride trihydrate (IrCl3(H2O)n, n=3) (7.63 g, 21.6 mmol) were mixed with 120 milliliters (mL) of ethoxyethanol and 40 mL of deionized (DI) water, and then, the resultant mixture was stirred and heated under reflux for 24 hours. Then, the temperature was allowed to lower to room temperature. The resultant solid was separated from the reaction mixture by filtration, washed sufficiently with DI water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 8.75 g (yield of 75%) of Compound A201(1).
Compound A201(1) (3.00 g, 2.80 mmol) and 60 mL of methylene chloride (MC) were mixed together, and then, a separate mixture including silver trifluoromethanesulfonate (AgOTf) (1.51 g, 5.88 mmol) and 20 mL of methanol (MeOH) was added thereto. Afterwards, the resultant mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then the reaction mixture was filtered through a Celite plug to remove the resulting solid. The solvent was removed from the filtrate under a reduced pressure to obtain a solid (Compound A201(2)). Compound A201(2) was used in the next reaction step without an additional purification process.
40 mL of ethanol was mixed with Compound A201(2) (3.24 g, 4.54 mmol) and Compound B2 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine) (1.966 g, 4.54 mmol), and then, the reaction mixture was stirred and heated at 90° C. under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid product was separated by filtration, and purified by column chromatography using EA (ethyl acetate):hexane (1:1 by volume) as eluents to obtain 1.46 g (yield of 34%) of Compound 1. Compound 1 was characterized by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.
HRMS (MALDI) calculated for C46H43GeIrN4O: m/z 934.2278 grams per mole (g/mol), found: 934.2277 g/mol.
Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine) (7.5 g, 33.1 mmol) and iridium chloride trihydrate (IrCl3(H2O)n) (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of DI water. The reaction mixture was stirred and heated under reflux for 24 hours, and then the temperature was allowed to lower to room temperature. The resultant solid was separated therefrom by filtration, washed sufficiently with DI water, methanol, and hexane, in this stated order, and then dried in a vacuum oven, to obtain 8.2 g (yield of 82%) of Compound A1(1).
Compound A1(1) (1.60 g, 1.18 mmol) and 45 mL of MC were mixed, and then, a separate mixture including AgOTf (0.61 g, 2.35 mmol) and 15 mL of methanol were added thereto. Afterwards, the reaction mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then filtered through a plug of Celite to remove the resulting solid. The solvent was removed from the filtrate under a reduced pressure to obtain a solid (Compound A1(2)). Compound A1(2) was used in the next reaction step without an additional purification process.
30 mL of ethanol was mixed with Compound A1(2) (1.610 g, 1.88 mmol) and Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) (0.818 g, 1.88 mmol), and then, the reaction mixture was stirred and heated under reflux at a temperature of 90° C. for 24 hours. Then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, and the product was purified by column chromatography using EA:hexane (1:1 v/v) as eluents to obtain 0.71 g (yield of 35%) of Compound 2.
HRMS (MALDI) calculated for C52H56D3GeIrN4OSi2: m/z 1081.3257 g/mol, found: 1081.3256 g/mol.
12.1 g (yield of 71%) of Compound B2(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B2 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound B2(2) was obtained in a similar manner as used to obtain Compound A1(2) in Synthesis Example 2, except that Compound B2(1) was used instead of Compound A1(1). The obtained Compound B2(2) was used in the next reaction step without an additional purification process.
Compound B2(2) (3.52 g, 2.78 mmol) and Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine) (0.631 g, 2.78 mmol) were mixed with 25 mL of 2-ethoxyethanol and 25 mL of N,N-dimethylformamide, and then, the reaction mixture was stirred and heated under reflux at a temperature of 130° C. for 48 hours. Then, the temperature was allowed to lower to room temperature. The solvent was removed from the resulting mixture under a reduced pressure to obtain a solid, and the solid was purified by column chromatography using EA:hexane (1:1 v/v) as eluents to obtain 1.18 g (yield of 33%) of Compound 3.
HRMS (MALDI) calculated for C62H70Ge2IrN5O2Si: m/z 1285.3352 g/mol, found: 1285.3351 g/mol.
11.6 g (yield of 74%) of Compound B6(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B6 (2-methyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (12.5 g, 33.15 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound B6(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound B6(1) was used instead of Compound A1(1). The obtained Compound B6(2) was used in the next reaction step without an additional purification process.
1.10 g (yield of 36%) of Compound 4 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound B6(2) (3.20 g, 2.77 mmol) was used instead of compound B2(2), and Compound A215 (4-(methyl-d3)-2-phenylpyridine) (0.477 g, 2.77 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
HRMS (MALDI) calculated for C52H45D3Ge2IrN5O2: m/z 1118.2049 g/mol, found: 1118.2047 g/mol.
0.98 g (yield of 31%) of Compound 5 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound A212 (4-isobutyl-2-phenylpyridine) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
HRMS (MALDI) calculated for C63H70Ge2IrN5O2: m/z 1269.3582 g/mol, found: 1269.3583 g/mol.
7.94 g (yield of 74%) of Compound A2(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A2 (4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine) (8.00 g, 28.22 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A2(2) was obtained in a similar manner as was used to obtain Compound A1 (2) in Synthesis Example 2, except that Compound A2(1) was used instead of Compound A1(1). The obtained Compound A2(2) was used in the next reaction step without an additional purification process.
1.35 g (yield of 37%) of Compound 6 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A2(2) (3.15 g, 3.25 mmol) was used instead of Compound A1(2), and Compound B201 (6-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (3.25 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C55H65GeIrN4OSi2: m/z 1120.3538 g/mol, found: 1120.3536 g/mol.
1.49 g (yield of 40%) of Compound 7 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A2(2) (3.18 g, 3.28 mmol) was used instead of Compound A1(2), and Compound B6 (2-methyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.236 g, 3.28 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C56H67GeIrN4OSi2: m/z 1134.3694 g/mol, found: 1134.3694 g/mol.
6.50 g (yield of 82%) of Compound A206 (1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A206 (5-(methyl-d3)-2-phenylpyridine) (5.00 g, 29.03 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A206(2) was obtained in a similar manner as used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A206(1) was used instead of Compound A1(1). The obtained Compound A206(2) was used in the next reaction step without an additional purification process.
1.32 g (yield of 35%) of Compound 8 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A206(2) (3.00 g, 4.01 mmol) was used instead of Compound A1(2), and Compound B106 (2-isopropyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.625 g, 4.01 mmol) was used instead of Compound B22(8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C46H37D6GeIrN4O: m/z 940.2654 g/mol, found: 940.2656 g/mol.
6.82 g (yield of 77%) of Compound A208(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A208 (4-isopropyl-5-methyl-2-phenylpyridine) (6.00 g, 28.39 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A208(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A208(1) was used instead of Compound A(1). The obtained Compound A208(2) was used in the next reaction step without an additional purification process.
1.38 g (yield of 35%) of Compound 9 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A208(2) (3.25 g, 3.93 mmol) was used instead of Compound A1(2), and Compound B26 (2-(methyl-d3)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.495 g, 3.93 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C50H48D3GeIrN4O: m/z: 993.3092 g/mol, found: 993.3091 g/mol.
6.67 g (yield of 74%) of Compound A203(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A203 (5-isopropyl-2-phenylpyridine) (6.00 g, 30.41 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A203(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A203(1) was used instead of Compound A1(1). The obtained Compound A203(2) was used in the next reaction step without an additional purification process.
1.25 g (yield of 32%) of Compound 10 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A203(2) (3.00 g, 3.76 mmol) was used instead of Compound A1(2), and Compound B111 (2-(2,6-dimethylphenyl)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.756 g, 3.76 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C55H53GeIrN4O: m/z: 1052.30604 g/mol, found: 1052.30604 g/mol.
4.87 g (yield of 78%) of Compound B26(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B26 (2-(methyl-d3)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (5 g, 13.16 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound B26(2) was obtained in a similar manner as was used to obtain Compound B2(2) in Synthesis Example 3, except that Compound B26(1) was used instead of Compound B2(1). The obtained Compound B26(2) was used in the next reaction step without an additional purification process.
1.12 g (yield of 35%) of Compound 11 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound B26(2) (3.00 g, 2.58 mmol) was used instead of Compound B2(2), and Compound A238 (4-(tert-butyl)-2-(dibenzo[b,d]furan-4-yl)pyridine) (0.779 g, 2.58 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
HRMS (MALDI) calculated for C61H50D6Ge2IrN5O3: m/z: 1253.2813 g/mol, found: 1253.2815 g/mol.
5.62 g (yield of 76%) of Compound A212(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A212 (4-isobutyl-2-phenylpyridine) (5 g, 23.66 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A212(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A212(1) was used instead of Compound A1(1). The obtained Compound A212(2) was used in the next reaction step without an additional purification process.
1.35 g (yield of 35%) of Compound 12 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A212(2) (3.00 g, 3.63 mmol) was used instead of Compound A1(2), and Compound B253 (2-(methyl-d3)-8-(4-isopropyl-5-(trimethylgermyl)pyridin-2-yl)benzothieno[2,3-b]pyridine) (1.59 g, 3.63 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C53H54D3GeIrN4S: m/z: 1051.3333 g/mol, found: 1051.3334 g/mol.
5.73 g (yield of 82%) of Compound A217(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A217 (4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridin) (5 g, 19.13 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A217(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A217(1) was used instead of Compound A1(1). The obtained Compound A217(2) was used in the next reaction step without an additional purification process.
1.44 g (yield of 34%) of Compound 13 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A217(2) (3.50 g, 3.78 mmol) was used instead of Compound A1(2) and Compound B67 (1,3-bis(methyl-d3)-8-(5-(methyl-d3)-4-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-c]pyridine) (1.57 g, 3.78 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C58H42D25GeIrN4O: m/z: 1127.5725 g/mol, found: 1127.5727 g/mol.
5.58 g (yield of 81%) of Compound A222(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A222 (5-(tert-butyl)-2-phenyl-4-(propan-2-yl-2-d)pyridine) (5 g, 19.65 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).
Compound A222(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A222(1) was used instead of Compound A1(1). The obtained Compound A222(2) was used in the next reaction step without an additional purification process.
1.35 g (yield of 31%) of Compound 14 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A222(2) (3.43 g, 3.76 mmol) was used instead of Compound A1 (2), and Compound B293 (9-(4-isopropyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[3,2-g]quinoline) (1.76 g, 3.76 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-nyl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).
HRMS (MALDI) calculated for C63H69D2GeIrN4O: m/z: 1168.4594 g/mol, found: 1168.4595 g/mol.
A glass substrate with ITO/Ag/ITO (as an anode) deposited thereon to a thickness of 70/1000/70 Å was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes each. Then, the resultant glass substrate was loaded onto a vacuum deposition apparatus.
Compound HT3 and Compound F6-TCNNQ were vacuum-deposited on the anode at the weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and, on the hole injection layer, Compound HT3 was vacuum-deposited to form a hole transport layer having a thickness of 1350 Å. Then, Compound H-H1 was deposited on the hole transport layer to form an electron-blocking layer having a thickness of 300 Å.
Then, Compound H-H1, Compound H-E43, and Compound 1 (dopant) were co-deposited on the electron-blocking layer at a weight ratio of 57:38:5 to form an emission layer having a thickness of 400 Å.
Then, Compound ET3 and Compound ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer with a thickness of 350 Å, and LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and both Mg and Ag were co-deposited at a weight ratio of 90:10 on the electron injection layer to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 58 were each used instead of Compound 1 as a dopant when forming the emission layer.
The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples R1 to R4. Results thereof are shown in Table 58. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifespan (T97) (at 15,000 candela per square meter (cd/m2)) was evaluated as the time (hr) taken for luminance to reduce to 97% from 100% of the initial luminance. Each of the maximum current efficiency and lifespan was expressed as a relative value (%).
Meanwhile, Compound H-H1, Compound H-E43 and Compound 1 were co-deposited on a quartz substrate at a weight ratio of 57:38:5 to produce a film with a thickness of 40 nm, and then the emission spectrum of the film was measured by using the Quantaurus-QY absolute PL quantum yield spectrometer (on which a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere (011347-12) are mounted and which includes PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka) manufactured by Hamamatsu Inc.). At the time of measurement, the excitation wavelength was measured by scanning from 320 nm to 380 nm at intervals of 10 nm, and a spectrum measured at the excitation wavelength of 340 nm was used to evaluate the emission peak wavelength of Compound 1 in Table 58.
The emission peak wavelength evaluation was similarly performed for the remaining compounds shown in Table 58, and the results are shown in Table 58.
From Table 58, it was confirmed that each of the organic light-emitting devices of Examples 1 to 4 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting devices of Comparative Examples R1 to R4.
Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 59 were used instead of Compound 1 as a dopant when forming the emission layer.
The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Example 5 and Comparative Example R5 and the emission peak wavelength of Compound 5 and Compound R5 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 59.
From Table 59, it was confirmed that the organic light-emitting device of Example 5 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R5.
Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 60 were used instead of Compound 1 as a dopant when forming the emission layer.
The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Example 6 and Comparative Example R6 and the emission peak wavelength of Compound 6 and Compound R6 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 60.
From Table 60, it was confirmed that the organic light-emitting device of Example 6 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R6.
Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 61 were used instead of Compound 1 as a dopant when forming the emission layer.
The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Examples 7 to 14 and the emission peak wavelength of Compound 7 to Compound 14 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 61. For comparison, the data of Comparative Example R1 is also shown in Table 61.
From Table 61, it was confirmed that the organic light-emitting devices of Example 7 to 14 emit a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R1.
Since the organometallic compounds have excellent thermal stability and/or electric characteristics, an electronic device using the organometallic compounds, for example, an organic light-emitting device using one or more of the organometallic compounds can have improved current efficiency and improved lifespan characteristics, and a high-quality electronic apparatus can be manufactured using the organic light-emitting device.
It should be understood that 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 typically be considered as available for other similar features or aspects in other embodiments.
While one or more exemplary embodiments have been described with reference to the FIGURE, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0065551 | May 2022 | KR | national |
