Patent Application
20220306667
This application is based on and claims priority to Korean Patent Application No. 10-2021-0033629, filed on Mar. 15, 2021, in the Korean Intellectual Property Office, and all benefits accruing therefrom under 35 U.S.C. § 119, the entire content of which is incorporated by reference herein.
One or more embodiments relate 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, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer 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 recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.
One or more embodiments relate to 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 description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect, an organometallic compound represented by Formula 1 is provided:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1,
M is a transition metal,
L1 is a ligand represented by Formula 2-1,
L2 is a ligand represented by Formula 2-2,
n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, each L1 is identical to or different from another, and when n2 is 2, each L2 is identical to or different from another,
a sum of n1 and n2 is 2 or 3,
L1 and L2 are different from each other,
wherein, in Formulae 2-1, 2-2, and 3,
Y1 and Y4 are each independently C or N,
X1 is Si or Ge,
X21 is O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30),
ring CY1, ring CY21, ring CY22, and ring CY14 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
A1 is a group represented by Formula 3, and A1 is not —CD3,
c1 is an integer from 1 to 20,
R21 to R23 are each independently a C1-C60 alkyl group or a C6-C60 aryl group, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof,
Z1 to Z5, R11 to R14, Z29, and Z30 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 C6-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), provided that at least one of Z3 to Z8 of Formula 3 is deuterium or a deuterated group, provided that in Formula 2-2,
R12 is hydrogen, deuterium, a methyl group, or a deuterated methyl group; or
R12 and R13 are 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,
a1, a2, and b1 are each independently an integer from 0 to 20, and when a1 is 2 or more, two or more of Z1(s) are identical to or different from each other, when a2 is 2 or more, two or more of Z2(s) are identical to or different from each other, and when b1 is 2 or more, two or more of R14(s) are identical to or different from each other,
two or more of R21 to R23 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,
two or more of a plurality of Z1(s) 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,
two or more of a plurality of Z2(s) 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,
two or more of Z3 to Z5 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,
two or more of a plurality of R14(s) are optionally be 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,
two or more of Z1, Z2 and R11 to R14 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 defined in connection with R14,
* and *′ in Formulae 2-1 and 2-2 each indicates a binding site to M in Formula 1,
* in Formula 3 indicates a binding site to ring CY1 in Formula 2-1, and
at least one substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-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 C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted 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 is:
deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group,
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 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 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 C6-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
According to another aspect, provided is 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 and including 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 the emission layer of the organic layer, and the organometallic compound included in the emission layer may act as a dopant.
Another aspect provides an electronic apparatus including the organic light-emitting device.
The above and other aspects, features, and advantages of certain exemplary embodiments of the disclosure will be more apparent from the following detailed description taken in conjunction with the FIGURE, which is a schematic 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, wherein like reference numerals refer to like elements throughout. In this regard, the present 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 detail below, by referring to the FIGURE, to explain aspects.
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. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
It will be understood that, 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 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.
The organometallic compound is represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
M in Formula 1 is a transition metal.
For example, M may be a Period 1 transition metal of the Periodic Table of the Elements, a Period 2 transition metal of the Periodic Table of the Elements, or a Period 3 transition metal of the Periodic Table of the Elements.
In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In one or more embodiments, M may be Ir, Pt, Os, or Rh.
L1 in Formula 1 is a ligand represented by Formula 2-1, and n1 in Formula 1 indicates the number of L1 in Formula 1 and is 1 or 2. When n1 is 2, two L1(s) are identical to or different from each other.
L2 in Formula 1 is a ligand represented by Formula 2-2, and n2 in Formula 1 indicates the number of L2 in Formula 1 and is 1 or 2. When n2 is 2, two L2(s) are identical to or different from each other.
Formulae 2-1 and 2-2 are as described herein.
L1 and L2 in Formula 1 are different from each other. That is, the organometallic compound represented by Formula 1 is a heteroleptic complex.
The sum of n1 and n2 is 2 or 3.
In one or more embodiments, M may be Ir, and the sum of n1 and n2 may be 3; or M may be Pt, and the sum of n1 and n2 may be 2.
Y1 and Y4 in Formula 2-2 are each independently C or N.
For example, Y1 in Formula 2-1 may be N, and Y4 in Formula 2-2 may be C.
X1 in Formula 2-2 is Si or Ge.
X21 in Formula 2-1 is O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30). Z29 and Z30 are each as described in the present specification.
For example, X21 in Formula 2-1 may be O or S.
In one or more embodiments, X21 in Formula 2-1 may be O.
In one or more embodiments, X21 in Formula 2-1 may be S.
Ring CY1, ring CY21, ring CY22, and ring CY14 in Formulae 2-1 and 2-2 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, ring CY1, ring CY21, ring CY22, and ring CY14 in Formulae 1-1 and 1-2 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other,
the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one or more embodiments, ring CY1, ring CY21, ring CY22, and ring CY14 in Formulae 2-1 and 2-2 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl 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, 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, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole 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 phenyl group condensed with an adamantane group, a phenyl group condensed with a norbornane group, a pyridine group condensed with an adamantane group, or a pyridine group condensed with a norbornane group.
In one or more embodiments, ring CY1, ring CY21, ring CY22, and ring CY14 in Formulae 2-1 and 2-2 may each independently be a phenyl group, a naphthalene group, a 1, 2, 3, 4-tetrahydronaphthalene group, a phenanthrene group, an anthracene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, or a benzoquinazoline group.
In one or more embodiments, ring CY1 in Formula 2-1 may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In one or more embodiments, ring CY21 in Formula 2-1 may be a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a pyridine group, or a pyrimidine group.
In one or more embodiments, ring CY22 in Formula 2-1 may be a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, an anthracene group, a pyridine group, a pyrimidine group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, an azadibenzofuran group, an azadibenzothiophene group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, or a benzoquinazoline group.
In one or more embodiments, ring CY14 in Formulae 2-2 may be a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.
M of Formula 1 may be bonded to carbon of ring CY21 of Formula 2-1.
A1 in Formula 2-1 is a group represented by Formula 3, provided that A1 is not —CD3:
That is, a case in which all of Z3 to Z5 in Formula 3 are deuterium simultaneously, is excluded. In other words, at least one of Z3 to Z5 is not deuterium.
Details for Formula 3 are as described herein.
c1 in Formula 2-1 indicates the number of A1(s), and is an integer from 1 to 20, for example, 1, 2, or 3. When c1 is 2 or more, two or more of A1(s) are identical to or different from each other. In one or more embodiments, c1 may be 1.
R21 to R23 in Formula 2-2 are each independently a C1-C60 alkyl group or a C6-C60 aryl group, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof.
For example, R21 to R23 in Formula 2-2 may each independently be a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, R21 to R23 in Formula 2-2 may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, or —CD2CH3.
In one or more embodiments, R21 to R23 in Formula 2-2 may be identical to each other.
In one or more embodiments, two or more of R21 to R23 in Formula 2-2 may be different from each other.
Z1 to Z5, R11 to R14, Z29, and Z30 in Formulae 2-1, 2-2, and 3 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 C6-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), provided that at least one of Z3 to Z5 of Formula 3 is deuterium or a deuterated group, and provided that in Formula 2-2, R12 is hydrogen, deuterium, a methyl group, or a deuterated methyl group, or R12 and R13 are 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. Q1 to Q9 are as described in the present specification.
For example, Z1, Z2, R11, R13, R14, Z29, and Z30 in Formulae 2-1 and 2-2 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, or a C2-C20 alkenyl group;
a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, or a C2-C20 alkenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopropyl group, a (C1-C20 alkyl)cyclobutyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group or an azadibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopropyl group, a (C1-C20 alkyl)cyclobutyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or
—Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).
a1, a2 and b1 in Formulae 2-1 and 2-2 indicate the number of Z1(s), the number of Z2(s), and the number of R14(s), respectively, and are each independently an integer from 0 to 20. When a1 is 2 or more, two or more of Z1(s) are identical to or different from each other, when a2 is 2 or more, two or more of Z2(s) are identical to or different from each other, and when b1 is 2 or more, two or more of R14(s) are identical to or different from each other. For example, a1, a2, and b1 may each independently be an integer from 0 to 10. In one or more embodiments, a1, a2, and b1 may each independently be 0, 1, or 2.
In one or more embodiments, Z1 to Z5, R11, R13, R14, Z29 and Z30 in Formulae 2-1 and 2-2 may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C2-C20 alkenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a 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 C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, R12 in Formula 2-2 may be hydrogen, deuterium, a methyl group, —CDH2, —CD2H, or —CD3.
In one or more embodiments, R12 in Formula 2-2 may be hydrogen or a methyl group.
In one or more embodiments, in relation to Formula 3,
i) Z3 may be deuterium or a deuterated group, and each of Z4 and Z5 may be a deuterium-free group;
ii) each of Z3 and Z4 may be deuterium or a deuterated group, and Z5 may be a deuterium-free group; or
iii) each of Z3 to Z5 may be deuterium or a deuterated group, provided that a case in which all of Z3 to Z5 are deuterium simultaneously, may be excluded. In other words, each of Z3 to Z5 is deuterium or a deuterated group, provided that at least one of Z3 to Z5 is not deuterium.
In one or more embodiments, at least one of Z3 to Z5 of Formula 3 may each independently be:
deuterium; or
a deuterated C1-C20 alkyl group, a deuterated C1-C20 alkoxy group, a deuterated C1-C20 alkylthio group, a deuterated C2-C20 alkenyl group, a deuterated phenyl group, a deuterated naphthyl group, a deuterated pyridinyl group, a deuterated dibenzofuranyl group, or a deuterated dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a 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 C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl) biphenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, Z3 and Z4 in Formula 3 may each independently be:
deuterium; or
a deuterated C1-C20 alkyl group, a deuterated C1-C20 alkoxy group, a deuterated C1-C20 alkylthio group, a deuterated C2-C20 alkenyl group, a deuterated phenyl group, a deuterated naphthyl group, a deuterated pyridinyl group, a deuterated dibenzofuranyl group, or a deuterated dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a 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 C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl) biphenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof, and
Z5 may be:
—F or a cyano group;
a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C2-C20 alkenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of —F, a cyano group, a C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl) phenyl group, a biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl) biphenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35) (where each of Q33 to Q35 may not include deuterium), or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5) (wherein each of Q3 to Q5 may not include deuterium).
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition (1) to Condition (3):
Condition (1)
Z1 in Formula 2-1 is not hydrogen, and a1 is an integer from 1 to 20
Condition (2)
R14 in Formula 2-2 is not hydrogen, and b1 is an integer from 1 to 20
Condition (3)
in Formula 2-1, Z2 is not hydrogen and a2 is an integer from 1 to 6.
In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one fluoro group (—F), at least one cyano group (—CN), or a combination thereof.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition A to Condition H:
Condition A
Z1 in Formula 2-1 is not hydrogen, a1 is an integer from 1 to 20, and at least one of Z1(s) in the number of a1 includes deuterium
Condition B
Z2 in Formula 2-1 is not hydrogen, a2 is an integer from 1 to 6, and at least one of Z2(s) in the number of 2 includes deuterium
Condition C
Z2 in Formula 2-1 is not hydrogen, a2 is an integer from 1 to 6, and at least one of Z2(s) in the number of 2 includes a fluoro group (—F)
Condition D
Z2 in Formula 2-1 is not hydrogen, a2 is an integer from 1 to 6, and at least one of Z2(s) in the number of 2 includes a cyano group (—CN)
Condition E
Z2 in Formula 2-1 is not hydrogen, a2 is an integer from 1 to 6, and at least one of Z2(s) in the number of a2 is a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group
Condition F
at least one of R21 to R23 in Formula 2-2 includes deuterium
Condition G
R14 in Formula 2-2 is not hydrogen, b1 is an integer from 1 to 20, and at least one of R14(s) in the number of b1 includes deuterium
Condition H
R14 in Formula 2-2 is not hydrogen, b1 is an integer from 1 to 20, and at least one of R14(s) in the number of b1 includes a fluoro group (—F)
In one or more embodiments, in relation to Formula 2-1, Z2 may not be hydrogen, a2 may be an integer from 1 to 3, and at least one of Z2(s) in the number of a2 may each independently be a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl 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 C6-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
In one or more embodiments, in relation to Formula 2-1, Z2 is not hydrogen, a2 is an integer from 1 to 3, and at least one of Z2(s) in the number of a2 is a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
In one or more embodiments, Z1, Z2, R11, R13, R14, Z29, and Z30 in Formulae 2-1 and 2-2 may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a C2-C10 alkenyl group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-233, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-132, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-353, a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in relation to Formula 3, Z3 may be deuterium, —CD3, —CD2H, —CDH2, —OCDH2, —OCD2H, —OCD3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, and each of Z4 and Z5 may be hydrogen, —F, a cyano group, —CH3, —CF3, —CF2H, —CFH2, —OCH3, —SCH3, a C2-C10 alkenyl group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-233, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-132, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-353, a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q), or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in relation to Formula 3, Z3 and Z4 may be each independently be deuterium, —CD3, —CD2H, —CDH2, —OCDH2, —OCD2H, —OCD3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, and Z5 may be hydrogen, —F, a cyano group, —CH3, —CF3, —CF2H, —CFH2, —OCH3, —SCH3, a C2-C10 alkenyl group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-233, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-132, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-353, a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, Z3 to Z5 in Formula 3 may each independently be deuterium, —CD3, —CD2H, —CDH2, —OCDH2, —OCD2H, —OCD3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-233 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium, provided that a case in which all of Z3 to Z5 are deuterium simultaneously, may be excluded:
In Formulae 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-132, and 10-201 to 10-353, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, “TMG” is a trimethylgermyl group, and “Ome” is a methoxy group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-233 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 9-635:
In one or more embodiments, A1 in Formula 2-1 may be a group represented by one of Formulae 9-501 to 9-514 or 9-601 to 9-635.
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 9-233 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 9-701 to 9-710:
The “group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with deuterium” and “the group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
The “group represented by one of Formulae 10-1 to 10-132 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-353 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-620:
In relation to Formulae 2-1 and 2-2, i) two or more of R21 to R23 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 Z1(s) 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 Z2(s) 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 Z3 to Z5 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 (for example, see Compound 161, etc.), v) two or more of a plurality of R14(s) 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 vi) two or more of a plurality of Z1, Z2, and R11 to R14 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.
Two or more of Z3 to Z5 of Formula 3 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 (for example, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, or the like, each unsubstituted or substituted with at least one R10a) (for example, see Compound 161, or the like).
R10a is as described in connection with R14.
* and *′ in Formulae 2-1 and 2-2 each indicates a binding site to M in Formula 1.
* in Formula 3 is a binding site to ring CY1 in Formula 2-1.
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 CY1-10:
wherein, in Formulae CY1-1 to CY1-10,
Z11, Z12 and Z14 are as described in connection with Z1, and each of Z11, Z12, and Z14 may not be hydrogen,
A13 is as described in connection with A1,
ring CY10a may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R10a may be understood by referring to the description of R10a provided herein,
aa may be an integer from 0 to 10,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to ring CY21 in Formula 2-1.
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 CY2-6:
wherein, in Formulae CY2-1 to CY2-6,
T1 to T8 may each independently be C or N,
X21 is as described in the present specification,
* indicates a binding site to ring CY1 in Formula 2-1, and
*′ indicates a binding site to M in Formula 1.
For example,
a) T1 to T8 of Formulae CY2-1 to CY2-6 may each be C, and/or
b) at least one of T3 to T8 of Formulae CY2-1 and CY2-6 (for example, one or two of T3 to T8) may be N, and/or
c) at least one of T1, T2 and T5 to T8 of Formulae CY2-2 and CY2-5 (for example, one or two of T1, T2, and T5 to T8) may be N, and/or
d) at least one of T1 and T4 to T8 of Formulae CY2-3 and CY2-4 (for example, one or two of T1 and T4 to T8) may be N.
In one or more embodiments,
1) T1 to T8 in Formulae CY2-1 to CY2-6 may be C;
2) in relation to Formula CY2-1, one of T3 to T8 may be N, and the others of T3 to T8 which are not N, may be C;
3) in relation to Formula CY2-1, T3 and T8 may be N, and T4 to T7 may each be C;
4) in relation to Formula CY2-1, T6 and T8 may be N, and T3 to T5 and T7 may each be C;
5) in relation to Formula CY2-2, one of T1, T2 and T8 may be N, and the others of T1, T2 and T5 to T8 which are not N, may be C;
6) in relation to Formula CY2-2, T1 and T8 may be N, and T2 and T5 to T7 may each be C;
7) in relation to Formula CY2-2, T2 and T8 may each be N, and each of T1 and T5 to T7 may be C;
8) in relation to Formulae CY2-3 and CY2-4, one of T1, T4 and T5 may be N, and the others of T1, T4 and T5 to T8, which are not N, may be C;
9) in relation to Formulae CY2-3 and CY2-4, T1 and T8 may be N, and T4 and T5 to T7 may be C;
10) in relation to Formula CY2-3 and CY2-4, T4 and T8 may be N, and T1 and T5 to T7 may each be C;
11) in relation to Formula CY2-5, one of T1 and T8 may be N, and the others of T1, T2 and T5 to T8 which are not N, may be C;
12) in relation to Formula CY2-5, T1 and T8 may be N, and T2 and T5 to T7 may each be C;
13) in relation to Formula CY2-6, one of T4 and T7 may be N, and the others of T3 to T8 which are not N, may be C; or
14) in relation to Formula CY2-6, T4 and T4 may each be N, and T3 and T5 to T7 may each be C.
In one or more embodiments, a group represented by
in Formula 2-1 may be a group represented by one of Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065, or CY2-6001 to CY2-6065:
wherein, in Formulae CY2-1001 to CY2-1141, CY2-2001 to CY2-2092, CY2-3001 to CY2-3092, CY2-4001 to CY2-4092, CY2-5001 to CY2-5065, and CY2-6001 to CY2-6065,
X21 is as described in the present specification,
Z21 to Z28 are as described in connection with Z2, and each of Z21 to Z28 is not hydrogen,
* indicates a binding site to ring CY1 in Formula 2-1, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, a group represented by
in Formula 2-2 may be a group represented by one of Formulae CY14-1 to CY14-64:
wherein, in Formulae CY14-1 to CY14-64,
R14 are as described in the present specification, and
X14 may be C(R1)(R2), N(R1), O, S, or Si(R1)(R2),
R1 to R8 are as described in connection with R14,
b18 may be an integer from 0 to 8,
b16 may be an integer from 0 to 6,
b15 may be an integer from 0 to 5,
b14 may be an integer from 0 to 4,
b13 may be an integer from 0 to 3,
b12 may be an integer from 0 to 2,
*″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2-2, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, a group represented by
in Formula 2-2 may be a group represented by one of Formulae CY14(1) to CY14(63):
wherein, in Formulae CY14(1) to CY14(63),
R14a to R14d are each as described in connection with R14, and each of R14a to R14d is not hydrogen,
X14 may be C(R1)(R2), N(R1), O, S, or Si(R1)(R2),
R1 to R8 are as described in connection with R14,
*″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2-2, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, the organometallic compound may be represented by Formula 1A:
wherein, in Formula 1A,
M, n1, n2, X1, X21, R21 to R23, and R11 to R13 are each as described in the present specification,
T11 may be N, C(A11), or C(Z11), T12 may be N, C(A12), or C(Z12), T13 may be N, C(A13), or C(Z13), T14 may be N, C(A14), or C(Z14), Z11 to Z14 are as described in connection with Z1, and A1 to A14 are as described in connection with A1. In one or more exemplary embodiments, i) T11 may be C(A11), or ii) T12 may be C(A12), or iii) T13 may be C(A13), or iv) T14 may be C(A14),
T21 may be N, C(Z21), carbon bonded to a neighboring 6-membered ring (i.e., the ring containing N and T12 to T14), or carbon bonded to M in Formula 1, T22 may be N, C(Z22), carbon bonded to a neighboring 6-membered ring, or carbon bonded to M in Formula 1, T23 may be N, C(Z23), carbon bonded to a neighboring 6-membered ring, or carbon bonded to M in Formula 1, T24 may be N, C(Z24), carbon bonded to a neighboring 6-membered ring, or carbon bonded to M in Formula 1, T25 may be N or C(Z25), T26 may be N or C(Z26), T27 may be N or C(Z27), T28 may be N or C(Z28), and one of T21 to T24 is carbon bonded to M in Formula 1, one of the others of T21 to T24 which are not bonded to M, may be carbon bonded to a neighboring 6-membered ring, and Z21 to Z24 are as described in connection with Z2,
i) R12 may be hydrogen, deuterium, a methyl group, or deuterated methyl group, or ii) R12 and R13 may optionally be linked to each other to form a C5-C30carbocyclic 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,
T31 may be N or C(R14a), T32 may be N or C(R14b), T33 may be N or C(R14c), T34 may be N or C(R14d), and R14a to R14d are as described in connection with R14,
two or more of Z11 to Z14 may optionally be 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,
two or more of Z21 to Z28 may optionally be 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,
two or more of R14a to R14d may optionally be 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
R10a is as described in connection with R14.
Further description of Formula 1A is as described in connection with Formula 1.
For example, T13 in Formula 1A may be C(A13).
In one or more embodiments, the organometallic compound may be one of Compounds 1 to 1204:
L1 in the organometallic compound represented by Formula 1 is a ligand represented by Formula 2-1, n1, which is the number of L1(s), is 1 or 2, L2 is a ligand represented by Formula 2-2, n2, which is the number of L2(s), is 1 or 2, and L1 and L2 are different from each other. That is, the organometallic compound is a heteroleptic complex essentially including (or consisting essentially of), as a ligand bonded to metal M, at least one ligand represented by Formula 2-1 and at least one ligand represented by Formula 2-2.
In relation to Formula 2-2, R12 is hydrogen, deuterium, a methyl group, or a deuterated methyl group; or R12 and R13 are 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. Accordingly, the organometallic compound represented by Formula 1 may have excellent heat resistance, and an electronic device, for example, an organic light-emitting device using the organometallic compound may have a long lifespan.
A1 in Formula 2-1 is a group represented by Formula 3 (at least one of Z3 to Z5 in Formula 3 is deuterium, or a deuterated group), and is not —CD3 (that is, a case in which all of Z3 to Z5 in Formula 3 are deuterium simultaneously, may be excluded), and c1, which is the number of A1(s), is an integer from 1 to 20. That is, ring CY1 of Formula 2-1 is substituted with at least one A1. As a result, the transition dipole moment of the organometallic compound represented by Formula 1 is increased, and the orientation characteristics of the organometallic compound are improved, and thus the luminescence efficiency of an electronic device, for example, an organic light-emitting device using the organometallic compound may be improved.
Furthermore, a group represented by *—X1(R21)(R22)(R23) in Formula 2-2 may be bonded at position 5 of the pyridine ring in the ligand represented by Formula 2-2 (see Formula 2-2). Since the organometallic compound including the ligand represented by Formula 2-2 has excellent heat resistance and decomposition resistance, an electronic device, for example, an organic light-emitting device, including the organometallic compound may have high stability and long lifespan during manufacture, storage, and/or operation.
The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, single (Si) energy level, and triple (Ti) energy level of organometallic compounds represented by Formula 1 were evaluated by density functional theory (DFT) using the Gaussian 09 program with the molecular structure optimization obtained at the B3LYP basis level, and results thereof are shown in Table 1, where the energy levels are 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 as a dopant for an electronic device, for example, 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.
Therefore, since the organometallic compound represented by Formula 1 may be suitable for use as a dopant of an organic layer of an organic light-emitting device, for example, an emission layer in the organic layer, according to another aspect, provided is an organic light-emitting device including a first electrode, a second electrode, and an organic layer which is located between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes at least one organometallic compounds represented by Formula 1.
The organic light-emitting device may have low driving voltage, high external quantum efficiency, and longer lifespan characteristics due to the inclusion of an organic layer including the organometallic compound represented by Formula 1 as described herein.
The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 in the emission layer is less than an amount of the host in the emission layer). The emission layer may emit, for example, green light or blue light.
The expression “(an organic layer) includes at least one of 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 represented by Formula 1”.
For example, the organic layer may include, as the organometallic compound, 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 organometallic compound, Compound 1 and Compound 2. 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 is an anode, and the second electrode is 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” used herein refers to a single layer and/or a plurality of layers 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 FIGURE is a schematic view of a cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of an organic light-emitting device according to one or more embodiments will be described with reference to the FIGURE. In the FIGURE, the organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
A substrate may be additionally disposed under the first electrode 11 or 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 metal or metal alloy, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
The organic layer 15 is 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 (A/sec) to about 100 Å/sec.
When the hole injection layer is formed by spin coating, the coating conditions may vary depending on a material for forming the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature in a range of about 80° C. to about 200° C. for removing a solvent after coating.
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)trphenylamine (TDATA), 4,4′, 4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), pi-NPB, N,N′bis(3-methylphenyl)-N,N′-diphenyl-[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 below, a compound represented by Formula 202 below, or a combination thereof:
Ar101 and Ar102 in Formula 201 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C00 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: 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 C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, or the like), a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like), or a C1-C60 alkylthio group; a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 alkylthio 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, or a combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group or a pyrenyl group, each unsubstituted or substituted with 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-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, or a combination thereof.
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 in the present specification.
For example, the hole transport region may include at least one of Compounds HT1 to HT20, or a combination thereof:
A thickness of the hole transport region may be in the range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron-blocking layer, or a combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within 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 a quinone derivative, a metal oxide, a cyano group-containing compound, or a combination thereof. For example, the p-dopant may be: a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide, such as tungsten oxide or molybdenum oxide; a cyano group-containing compound, such as Compound HT-D1; or a combination thereof.
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 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 above, a host material described below, or a combination thereof. In one or more embodiments, when the hole transport region includes an electron-blocking layer, mCP, which will be described later may be used as an electron-blocking layer material.
Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied 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 the organometallic compound represented by Formula 1 as described herein.
The host may include 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), N,N′,N″-1,3,5-tricarbazoloylbenzene (TCP), 1,3-bis(carbazol-9-yl)benzene (mCP), Compound H50, Compound H51, Compound H52, or a combination thereof:
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 white light.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. 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.
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 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:
A thickness of the hole-blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole-blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include BCP, Bphen, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi), tris(8-hydroxyquinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (Balq), 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:
A thickness of the electron transport layer may be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, 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 material as described above.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 or ET-D2:
The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within 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 metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device according to one or more embodiments has been described in connection with the FIGURE. However, embodiments of the present disclosure 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 organiclight-emitting device is provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, and the like.
Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.
The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used here refers to a divalent group having the same structure as the C1-C60 alkyl group.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with 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. For example, Formula 9-33 is a branched C6 alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof are a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
The term “C1-C6 alkylthio group” as used herein refers to a monovalent group represented by —SA101 (wherein A101 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 a C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of a C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
Examples of the C3-C10 cycloalkyl group are a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group that includes at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and has no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring, and has no aromaticity. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include 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 having at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a cyclic aromatic system having 1 to 60 carbon atoms. The term “C1-C00 heteroarylene group” as used herein refers to a divalent group having at least one hetero atom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and a carbocyclic aromatic system having 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the 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 —OA102 (wherein A102 indicates the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 indicates the C6-C60 aryl group).
The term “C1-C60 heteroaryloxy group” as used herein indicates —OA102′ (wherein A102 indicates the C1-C60 heteroaryl group). The term “C1-C6 heteroarylthio group” as used herein indicates —SA103′ (wherein A103′ indicates the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group 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. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a)” used herein are 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 phenyl 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. 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, or a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R10a).
Examples of the “C5-C30 carbocyclic group” and the “C1-C30 heterocyclic group” as used herein are i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
wherein the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
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” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group (that is, a fluorinated methyl group)” includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or, a fluorinated C1-C20 alkyl group, or the like)”, “the fluorinated C3-C10 cycloalkyl group”, “the fluorinated C1-C10 heterocycloalkyl group”, or “the fluorinated a phenyl group” may be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, not all hydrogen included therein is substituted with a fluoro group.
The term “deuterated group” as used herein refers to a substituent group having at least one hydrogen atom substituted with deuterium. 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” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group (that is, the deuterated methyl group)” may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C1-C60 alkyl group (or, the deuterated C1-C20 alkyl group or the like)”, “the deuterated C3-C10 cycloalkyl group”, “the deuterated C1-C10 heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein 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, not all hydrogen included therein are substituted with deuterium.
The term “deuterium-free group” as used herein refers to a substituent group that does not have at least one hydrogen atom substituted with deuterium. That is, the term “deuterium-free group” as used herein refers to a substituent group that does not have a 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 is a toluyl group.
The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzothiophene 5,5-dioxide group,” in which, in each group, at least one carbon selected from ring-forming carbons is substituted with nitrogen.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted 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 C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C1-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 each independently be:
deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C00 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof.
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 used herein may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted 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 C6-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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 as described herein may each independently be: —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2, or 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, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
Hereinafter, a compound and an organic light-emitting device according to one or more 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.
80 milliliters (mL) of tetrahydrofuran (THF) and 30 mL of deionized (DI) water were mixed with 2-bromo-5-(trimethylsilyl)pyridine (10 grams (g), 43.44 millimoles (mmol)), phenylboronic acid (5.83 g, 47.79 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 2.51 g, 2.17 mmol), and potassium carbonate (K2CO3, 18.01 g, 130.33 mmol), and then, the mixture was stirred and heated under reflux at 80° C. for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using methylene chloride (MC), anhydrous magnesium sulfate (MgSO4) was added thereto to remove moisture, and the filtrate obtained by filtration was exposed to reduced pressure to obtain the residual product, which was then purified by column chromatography using ethyl acetate (EA) and hexane at a ratio of 1:4 (volume ratio, the same below), thereby obtaining 7.23 g (73%) of Compound C1.
90 mL of 2-ethoxyethanol and 30 mL of DI water were mixed with Compound C1 (5.0 g, 22.04 mmol) and iridium chloride trihydrate (IrCl3(H2O)n, n=3, 3.70 g, 10.49 mmol), and then, the mixture was stirred and heated under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, washed sufficiently with DI water, methanol (MeOH), and hexanes, in this stated order, and then dried in a vacuum oven to obtain 6.53 g (46%) of Compound B1.
Compound B1 (5.00 g, 3.67 mmol) was mixed with 90 mL of MC (i.e., DCM), and then, (trifluoromethanesulfonate)silver(I) (AgOTf, 2.03 g, 7.90 mmol) dissolved in 30 mL of methanol was added thereto. Afterwards, the resultant reaction solution was stirred to proceed a reaction for 18 hours at room temperature while light was blocked from the reaction solution with aluminum foil, and then filtered through CELITE to remove a solid produced therein. The filtrate was then subjected to reduced pressure to obtain a solid (Compound A1) that was used in the next reaction without an additional purification process.
2-bromo-4-(propan-2-yl-2-d)pyridine (4.44 g, 22.20 mmol), dibenzo[b,d]thiophen-4-ylboronic acid (5.06 g, 22.20 mmol), Pd(PPh3)4 (1.28 g, 1.11 mmol), and K2CO3 (9.20 g, 66.60 mmol) were mixed with 90 mL of THE and 30 mL of DI water, followed by stirring and heating under reflux for at 80° C. 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:2, thereby obtaining 4.93 g (73%) of Compound L1.
Compound A1 (5.15 g, 6.00 mmol) and Compound L1 (1.83 g, 6.00 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide (DMF), and then, the resultant solution was stirred and heated under reflux for 48 hours at a temperature of 120° C. Then, the temperature was allowed to lower to room temperature. After removing the solvents under reduced pressure, column chromatography was performed using EA and hexane at a ratio of 1:8 to obtain 1.42 g (25%) of Compound 1. The obtained compound was identified by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS(MALDI)) and high-performance liquid chromatography (HPLC) analysis.
HRMS (MALDI) calculated for C48H47DIrN3SSi2: m/z: 948.2799, found: 948.2805.
2-bromo-5-(trimethylsilyl)pyridine (10 g, 43.44 mmol), 4-fluorophenylboronic acid (6.08 g, 43.44 mmol), Pd(PPh3)4 (2.51 g, 2.17 mmol), and K2CO3 (18.01 g, 130.33 mmol) were mixed with 90 mL of tetrahydrofuran (THF) and 30 mL of DI water, and then stirred and heated under reflux at 80° C. for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:4, thereby obtaining 8.53 g (80%) of Compound C2.
Compound C2 (7.36 g, 30.00 mmol) and iridium chloride hydrate (8.66 g, 29.00 mmol) were mixed with 90 mL of 2-ethoxyethanol and 30 mL of DI water, and then, the mixture was stirred and heated under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, washed sufficiently with DI water, methanol, and hexanes, in this stated order, and then dried in a vacuum oven to obtain 8.60 g (80%) of Compound B2.
Compound B2 (5.26 g, 3.67 mmol) was mixed with 90 mL of MC, and then, AgOTf (1.13 g, 4.40 mmol) dissolved in 30 mL of methanol was added thereto. Afterwards, the resultant reaction solution was stirred to proceed a reaction for 18 hours at room temperature while light was blocked from the reaction solution with aluminum foil, and filtered through CELITE to remove a solid produced therein. The filtrate was then subjected to reduced pressure to obtain a solid (Compound A2) which was used in the next reaction without an additional purification process.
2-bromo-4-(phenylmethyl-d2)pyridine (5.00 g, 20.00 mmol), (1-methyl-7-phenyldibenzo[b,d]thiophen-4-yl)boronic acid (6.36 g, 20.00 mmol), Pd(PPh3)4 (1.14 g, 1.00 mmol), and K2CO3 (8.29 g, 60.00 mmol) were mixed with 90 mL of THE and 30 mL of DI water, followed by stirring and heating under reflux at 80° C. for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:2, thereby obtaining 7.72 g (87%) of Compound L2.
Compound A2 (3.00 g, 3.36 mmol) and Compound L2 (1.49 g, 3.36 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and then, the resultant solution was stirred under reflux for 48 hours at a temperature of 120° C. Then, the temperature was allowed to lower to room temperature. After removing the solvents under reduced pressure condition, column chromatography was performed using EA and hexane at a ratio of 1:10 to obtain 0.79 g (21%) of Compound 2. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C59H50D2F2IrN3SSi2: m/z: 1123.3143, found: 1123.3102.
2-bromo-4-methyl-5-(trimethylgermyl)pyridine (5 g, 17.32 mmol), phenylboronic acid (2.11 g, 17.32 mmol), Pd(PPh3)4 (1.20 g, 1.04 mmol), and K2CO3 (7.18 g, 51.96 mmol) were mixed with 90 mL of tetrahydrofuran (THF) and 30 mL of DI water, and then stirred and heated under reflux at 80° C. for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:8, thereby obtaining 4.21 g (85%) of Compound C3.
Compound C3 (8.58 g, 30.00 mmol) and iridium chloride hydrate (4.48 g, 15.00 mmol) were mixed with 90 mL of 2-ethoxyethanol and 30 mL of DI water, and then, the mixture was stirred and heated under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, washed sufficiently with DI water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 7.78 g (65%) of Compound B3.
Compound B3 (3.00 g, 1.88 mmol) was mixed with 90 mL of MC, and then, AgOTf (1.01 g, 3.95 mmol) dissolved in 30 mL of methanol was added thereto. Afterwards, the resultant reaction solution was stirred to proceed a reaction at 80° C. for 18 hours at room temperature while light was blocked from the reaction solution with aluminum foil, and filtered through CELITE to remove a solid produced therein. The filtrate was then subjected to reduced pressure to obtain a solid (Compound A3) which was used in the next reaction without an additional purification process.
2-bromo-4-(2,2-dimethylpropyl-1,1-d2)pyridine (5.00 g, 21.73 mmol), dibenzo[b,d]thiophen-4-ylboronic acid (4.96 g, 21.73 mmol), Pd(PPh3)4 (1.24 g, 1.09 mmol), and K2CO3 (9.01 g, 60.00 mmol) were mixed with 90 mL of THE and 30 mL of DI water, followed by stirring and heating under reflux for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was exposed to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:2, thereby obtaining 5.29 g (73%) of Compound L3.
Compound A3 (3.00 g, 3.08 mmol) and Compound L3 (1.03 g, 3.08 mmol) were mixed with 100 mL of ethanol, and the temperature was lowered after the reaction was carried out by stirring under reflux at 80° C. for 48 hours. After removing all solvent under reduced pressure, column chromatography was performed using EA and hexanes at the ratio of 1:10 to obtain 1.18 g (35%) of Compound 3. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C52H54D2Ge2lrN3S: m/z: 1097.2373, found: 1097.2398.
2-bromo-5-(trimethylgermyl)pyridine (5 g, 18.20 mmol), phenylboronic acid (2.22 g, 18.20 mmol), Pd(PPh3)4 (1.05 g, 0.91 mmol), and K2CO3 (7.55 g, 54.60 mmol) were mixed with 90 mL of THE and 30 mL of DI water, and then stirred and heated under reflux at 80° C. for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexane at a ratio of 1:8, thereby obtaining 4.06 g (82%) of Compound C4.
Compound C4 (8.16 g, 30.00 mmol) and iridium chloride hydrate (4.48 g, 15.00 mmol) were mixed with 90 mL of 2-ethoxyethanol and 30 mL of DI water, and then, the mixture was stirred and heated under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, washed sufficiently with DI water, methanol, and hexanes, in this stated order, and then dried in a vacuum oven to obtain 8.43 g (73%) of Compound B4.
Compound B4 (3.00 g, 1.95 mmol) was mixed with 90 mL of MC, and then, AgOTf (1.05 g, 4.10 mmol) dissolved in 30 mL of methanol was added thereto. Afterwards, the resultant reaction solution was stirred to proceed a reaction at 80° C. for 18 hours at room temperature while light was blocked from the reaction solution with aluminum foil, and filtered through CELITE to remove a solid produced therein. The filtrate was then subjected to reduced pressure to obtain a solid (Compound A4) which was used in the next reaction without an additional purification process.
2-bromo-4-(2,2-dimethylpropyl-1,1-d2)pyridine (5.00 g, 21.73 mmol), benzo[b]phenanthro[2,3-d]thiophen-11-ylboronic acid (7.13 g, 21.73 mmol), Pd(PPh3)4 (1.26 g, 1.09 mmol), and K2CO3 (9.01 g, 65.19 mmol) were mixed with 90 mL of THE and 30 mL of DI water, followed by stirring and heating under reflux for 18 hours. After the temperature was allowed to lower to room temperature, the organic layer was extracted using MC, anhydrous MgSO4 was added thereto to remove residual water, and the filtrate obtained by filtration was subjected to reduced pressure to obtain the residual product, which was then purified by column chromatography using EA and hexanes at the ratio of 1:10, thereby obtaining 8.29 g (88%) of Compound L4.
Compound A4 (3.00 g, 3.17 mmol) and Compound L4 (1.37 g, 3.17 mmol) were mixed with 100 mL of ethanol, and the reaction was carried out by stirring and heating under reflux at 80° C. for 48 hours, and then the temperature was allowed to lower to room temperature. After removing the solvent under reduced pressure, column chromatography was performed using EA and hexane at a ratio of 1:10 to obtain 1.11 g (30%) of Compound 4. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI) calculated for C58H54D2Ge2IrN3S: m/z: 1169.2373, found: 1169.2356.
A coated glass substrate with ITO/Ag/ITO (as an anode) deposited thereon to a thickness of 70 Å/1000 Å/70 Å was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water each for 5 minutes, and then cleaned by exposure to ultraviolet (UV) rays and ozone for 30 minutes. Then the resultant coated glass substrate was loaded onto a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino] biphenyl (hereinafter referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1350 Å.
Next, CBP (host) and Compound 1 (dopant) were co-deposited at a weight ratio of 98:2 on the hole transport layer to form an emission layer having a thickness of 400 Å.
Thereafter, BCP was vacuum-deposited on the emission layer to form a hole-blocking layer having a thickness of 50 Å, Alq3 was vacuum-deposited on the hole-blocking layer to form an electron transport layer having a thickness of 350 Å, LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and 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 in a similar manner as in Example 1, except that Compounds shown in Table 2 were each used instead of Compound 1 as a dopant in forming an emission layer.
For each of the organic light-emitting devices manufactured in Examples 1 to 4, the driving voltage(V), the maximum value of the external quantum efficiency (Max EQE) (%), and lifespan (LT97) (hr) were evaluated. The results are shown in Table 2 as a relative value (%) with respect to the values of Example 1. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as an apparatus for evaluation, the lifespan (LT97) (at 3500 candela per square meter, cd/m2 or nits) was obtained by measuring the amount of time (hr) that elapsed until luminance was reduced to 97% of the initial brightness of 100%.
From Table 2, it can be confirmed that the organic light-emitting devices of Examples 1 to 4 have excellent characteristics in terms of driving voltage, external quantum efficiency, and lifespan.
Since the organometallic compounds have excellent electrical characteristics and heat resistance, an electronic device, for example, an organic light-emitting device, using one or more of the organometallic compounds may have excellent characteristics in terms of driving voltage, external quantum efficiency (EQE), and lifespan. Therefore, the use of the organometallic compound(s) may provide a high-quality organic light-emitting device and an electron device including the same.
It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of certain features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more 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 |
|---|---|---|---|
| 10-2021-0033629 | Mar 2021 | KR | national |
