Patent Application
20230011568
This application claims priority to Korean Patent Application No. 10-2020-0060898, filed on May 21, 2020, and Korean Patent Application No. 10-2021-0064010, filed on May 18, 2021, both in the Korean Intellectual Property Office, and all benefits accruing therefrom under 35 U.S.C. § 119, the entire contents of which are incorporated herein by reference.
The present disclosure relates to an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices (OLEDs) are self-emissive devices which produce full-color images. In addition, OLEDs have wide viewing angles and exhibit excellent driving voltage and response speed characteristics.
The structure of an OLED includes an anode, a cathode, and an organic layer located between the anode and the cathode, where the organic layer typically includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons may recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state to thereby generate light, for example, visible light.
One or more aspects provide an organometallic compound, an organic light-emitting device including at least one of the organometallic compound, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the detailed description which follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments of the disclosure.
According an aspect of one or more embodiments, an organometallic compound is represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1,
M may be a transition metal,
L1 may be a ligand represented by Formula 2A,
L2 may be a ligand represented by Formula 2B,
n1 and n2 may each independently be 1 or 2, when n1 is 2, two L1(s) may be identical to or different from each other, and when n2 is 2, two L2(s) may be identical to or different from each other,
the sum of n1 and n2 may be 2 or 3,
L1 may be different from L2,
wherein, in Formulae 2A and 2B,
Y4 is C or N,
X1 is Si or Ge,
X21 is O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30),
T1 to T4 are each independently C, N, a carbon atom bound to ring CY1, or a carbon atom bound to M in Formula 1, provided that one of T1 to T4 is a carbon atom bound to M in Formula 1, and another one of T1 to T4, which is not bound to M, is a carbon atom bound to ring CY1,
T5 to T8 are each independently C or N,
a total number of N atoms among T1 to T8 is 0 or 1,
ring CY1 and ring CY14 re each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
Are is a ring CY2 unsubstituted or substituted with at least one Z0, wherein ring CY2 is an unsaturated C5-C39 carbocyclic group or an unsaturated C1-C30 heterocyclic group,
R21 to R23 are each independently a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof,
Z0, Z1, Z2, Z29, Z30, and R11 to R14 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 C2-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 C8-C80 arylthio group, a substituted or unsubstituted C1-C60 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),
d2 is an integer from 1 to 6, and when d2 is 2 or greater, at least two Ar2(s) are identical to or different from each other,
a1 and b1 re each independently an integer from 0 to 20, when a1 is 2 or greater, at least two Z1(s) are identical to or different from each other, and when b1 is 2 or greater, at least two R14(s) are identical to or different from each other,
a2 is an integer from 0 to 5, and when a2 is 2 or greater, at least two Z2(s) are identical to or different from each other,
Condition 1 or Condition 2 is satisfied:
Condition 1
Condition 2
at least two of R21 to R23 are optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of a plurality of Z1(s) are optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of a plurality of Z2(s) re optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R12 and R13 are optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of a plurality of R14(s) are optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of Z0, Z1, Z2, Z29, Z30, and R11 to R14 are optionally bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, R10a is understood by referring to the description of R14 provided herein,
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 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 C2-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, —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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 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 C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alky 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; 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 unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C1-C60 alkylthio group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a 03-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with one or more of deuterium, a C1-C60 alkyl group, or a C6-C60 aryl group; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 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.
According to an aspect of one or more embodiments, an organic light-emitting device may include a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer may include an emission layer, and wherein the organic layer may include at least one organometallic compound described herein.
In one or more embodiments, the at least one organometallic compound is included in the emission layer of the organic layer. In one or more embodiments, the organometallic compound included in the emission layer may serve as a dopant.
According to another aspect of one or more embodiments, an electronic apparatus includes the organic light-emitting device.
The above and other aspects, features, and advantages of one or more exemplary embodiments will be more apparent from the following detailed description taken in conjunction with the accompanying drawing, in which:
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
An organometallic compound represented by Formula 1 is provided herein:
M(L1)n1(L2)n2 Formula 1
wherein, in Formula 1, M is a transition metal.
In one or more embodiments, M may be a first-row transition metal, a second-row transition metal, or a third-row transition metal.
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.
In Formula 1, L1 is a ligand represented by Formula 2A, n1 in Formula 1 indicates the number of L1(s) in Formula 1, and n1 is 1 or 2. When n1 is 2, two L1(s) are identical to or different from each other.
In Formula 1, L2 is a ligand represented by Formula 2B, n2 in Formula 1 indicates the number of L2(s) in Formula 1, and n2 is 1 or 2. When n2 is 2, two L2(s) are identical to or different from each other.
Formulae 2A and 2B may respectively be understood by referring to the descriptions of Formulae 2A and 2B provided herein.
L1 and L2 in Formula 1 may be different from each other. That is, the organometallic compound represented by Formula 1 may be a heteroleptic complex.
In one or more embodiments, M may be Ir, n1+n2=3; or M may be Pt, n1+n2=2.
In one or more embodiments, M may be Ir in Formula 1 and i) n1 may be 1 and n2 may be 2; or ii) n1 may be 2 and n2 may be 1.
In Formula 2B, Y4 may be C or N.
In one or more embodiments, in Formula 2B, Y4 may be C.
In Formula 2B, X1 is Si or Ge.
In Formula 2A, X21 is O, S, S(═O), N(Z29), C(Z29)(Z30), or Si(Z29)(Z30). Z29 and Z30 may respectively be understood by referring to the descriptions of Z29 and Z30 provided herein.
In one or more embodiments, X21 in Formula 2A is O or S.
In Formula 2A, T1 to T4 are each independently C, N, a carbon atom bound to ring CY1, or a carbon atom bound to M in Formula 1, provided that one of T1 to T4 is a carbon atom bound to M in Formula 1, and another one of T1 to T4, which is not bound to M, is a carbon atom bound to ring CY1, and T5 to T8 are each independently C or N.
A total number of N atoms among T1 to T8 in Formula 2A is 0 or 1.
In Formulae 2A and 2B, ring CY1 and ring CY14 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, Are in Formula 2A is a ring CY2 unsubstituted or substituted with at least one Z0, and the ring CY2 is an unsaturated C5-C30 carbocyclic group or an unsaturated C1-C30 heterocyclic group. Z0 is understood by referring to the description of Z0 provided herein.
In one or more embodiments, in Formulae 2A and 2B, ring CY1 and ring CY14 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In one or more embodiments, ring CY1 and ring CY14 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene 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, or an azadibenzosilole group.
In one or more embodiments, in Formula 2A, ring CY1 may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline.
In one or more embodiments, in Formula 2B, ring CY14 may be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.
In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In Formula 2B, R21 to R23 may each independently be a C1-C60 alkyl group or a C6-C60 aryl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, in Formula 2B, R21 to R23 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, in Formula 2B, R21 to R23 may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, or —CD2CH3.
In one or more embodiments, in Formula 2B, R21 to R23 may be identical to one another.
In one or more embodiments, in Formula 2B, at least two of R21 to R23 may be different from each other.
In Formulae 2A and 2B, Z0, Z1, Z2, Z29, Z30, and R11 to R14 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 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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)(Q9)(Q9), or —P(Q9)(Q9), wherein Q1 to Q9 may respectively be understood by referring to the descriptions of Q1 to Q9 provided herein.
In Formula 2A, d2 indicates the number of Ar2(s), and d2 may be an integer from 1 to 6. When d2 is 2 or greater, at least two Ar2(s) may be identical to different from each other. In one or more embodiments, d2 may be 1, 2, or 3. In one or more embodiments, d2 may be 1 or 2.
In Formulae 2A and 2B, a1 and b1 may respectively indicate the number of Z1(s) and R14(s), and a1 and b1 may each independently be an integer from 0 to 20. When a1 is 2 or greater, at least two Z1(s) may be identical to or different from each other. When b1 is 2 or greater, at least two R14(s) may be identical to or different from each other. In one or more embodiments, a1 and b1 may each independently be an integer from 0 to 10.
In Formula 2A, a2 indicates the number of Z2(s), and a2 may be an integer from 0 to 5. When a2 is 2 or greater, at least two Z2(s) may be identical to different from each other. In one or more embodiments, a2 may be 0, 1, 2, or 3.
In one or more embodiments, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano 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 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 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, or a combination thereof; or a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated C1-C20 alkoxy group, a fluorinated C1-C20 alkoxy 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 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 a biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof.
In one or more embodiments, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be:
hydrogen or deuterium;
a C1-C20 alkyl group unsubstituted or substituted with deuterium, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated C1-C10 heterocycloalkyl group, a (C1-C20 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof; or
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a deuterated heterocycloalkyl group, a (C1-C20 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof.
In one or more embodiments, Z0 and Z2 in Formula 2A and R14 in Formula 2B may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, a cyano 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 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, or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C1-C20 alkoxy group, a deuterated C1-C20 alkoxy group, a fluorinated C1-C20 alkoxy 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 heterocycloalkyl group, a fluorinated heterocycloalkyl group, a (C1-C20 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 a biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof; or —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in Formulae 2A and 2B, Z0, Z1, Z2, Z29, Z30, and R11 to R14 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a (phenyl)C1-C10 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, 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, an azadibenzothiophenyl group, or a combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2;
an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
In one or more embodiments, R21 to R23, Z1, Z2, and R11 to R14 in Formulae 2A and 2B may not include silicon (Si). Accordingly, an electronic device, e.g., an organic light-emitting device, including the organometallic compound represented by Formula 1 may have improved out-coupling characteristics.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions A, B, and C:
Condition A
Condition B
Condition C
The organometallic compound represented by Formula 1 satisfies Condition 1 or Condition 2:
Condition 1
Condition 2
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 1.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 1 and the number of carbon atoms included in R12 of Formula 2B may be 2 or greater.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 1 and R12 in Formula 2B may be:
a C2-C20 alkyl group or a C2-C20 alkoxy group;
a methyl group or a methoxy group, each substituted with a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof;
a C2-C20 alkyl group or a C2-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C7-C14 alky aryl group, a C7-C14 aryl alkyl group, a C1-C14 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof; or
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C20 alkyl group, a C1-C20 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C14 aryl group, a C7-C14 alky aryl group, a C7-C14 aryl alkyl group, a C1-C14 heteroaryl group, a substituted or unsubstituted C2-C14 alkyl heteroaryl group, a substituted or unsubstituted C2-C14 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 1 and R12 in Formula 2B may be:
a methyl group or a methoxy group, substituted with a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
a methyl group or a methoxy group, substituted with i) a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof, and ii) at least one deuterium;
a C2-C20 alkyl group or a C2-C20 alkoxy group, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof; or
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantanyl group, a (C1-C20 alkyl)norbornanyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, 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, an azadibenzothiophenyl group, or a combination thereof.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein, X1 in Formula 2B may be Si, and the total number of N atoms among T1 to T8 in Formula 2A may be 0.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein, X1 in Formula 2B may be Ge, and the total number of N atoms among T1 to T8 in Formula 2A may be 0.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein, X1 in Formula 2B may be Si, and the total number of N atoms among T1 to T8 in Formula 2A may be 1.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein, X1 in Formula 2B may be Ge, and the total number of N atoms among T1 to T8 in Formula 2A may be 1.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy Condition 2 as described herein, and R12 in Formula 2B may include at least one deuterium.
In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium, 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 include at least one deuterium.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions (1A), (2A), or (3) to (6); or the organometallic compound represented by Formula 1 may satisfy Condition (7):
Condition (1A)
Condition (2A)
Condition (3)
Condition (4)
Condition (5)
Condition (6)
Condition (7)
In one or more embodiments, in Formulae 2A and 2B, Z0, Z1, Z2, Z29, Z30, and R11 to R14 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 group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 may respectively be understood by referring to the descriptions of Q3 to Q5 provided herein.
In one or more embodiments, Z1 in Formula 2A and R11 to R13 in Formula 2B may each independently be hydrogen, deuterium, —CH3, —CD3, —CD2H, —CDH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-138 and 10-145, or a group represented by one of Formulae 10-1 to 10-138 and 10-145 in which at least one hydrogen is substituted with deuterium.
In one or more embodiments, Are in Formula 2A may be a group represented by one of Formulae 10-12 to 10-145, a group represented by one of Formulae 10-12 to 10-145 in which at least hone hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F.
In one or more embodiments, R12 in Formula 2B may be hydrogen, —CH3, —CH2D, —CHD2 or —CD3.
In one or more embodiments, R12 in Formula 2B may be hydrogen or a methyl group (—CH3).
In one or more embodiments, R12 in Formula 2B may be —CH2D, —CHD2 or —CD3.
In one or more embodiments, R12 in Formula 2B may be a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F.
In Formulae 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, “TMG” represents a trimethylgermyl group, and “OMe” represents 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 9-230 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-637:
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F” may 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 10-145 in which at least one hydrogen is substituted with a deuterium” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium” may each 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 10-145 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F” may each be, for example, a group represented by one of Formulae 10-601 to 10-636:
In Formulae 2A and 2B, i) at least two of R21 to R23 may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, ii) at least two of a plurality of Z1(s) may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, iii) at least two of a plurality of Z2(s) may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, iv) R12 and R13 may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, v) at least two of a plurality of R14(s) may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, vi) at least two of Z0, Z1, Z2, Z29, Z30, and R11 to R14 may optionally be bound to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
R10a as used herein may be understood by referring to the description of R14 provided herein.
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY1(1) to CY1(16):
wherein, in Formulae CY1(1) to CY1(16),
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to one of T1 to T4 in Formula 2A.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY1-1 to CY1-28:
wherein, in Formulae CY1-1 to CY1-28,
Z11 to Z14 may each be same as described in connection with Z1 provided herein, wherein Z11 to Z14 may not each be hydrogen,
ring CY10a may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R10a may be the same as described 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 one of T1 to T4 in Formula 2A.
In one or more embodiments, ring CY10a may be a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY1-1, CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.
In one or more embodiments, in Formula 2A, a group represented by
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, the number of N(s) among T3 to T8 in Formulae CY2-1 and CY2-6 may be 0 or 1, the number of N(s) among T1, T2, T5, T6, T7, and T8 in Formulae CY2-2 and CY2-5 may be 0 or 1, the number of N(s) among T1, T4, T5, T6, T7, and T8 in Formulae CY2-3 and CY2-4 may be 0 or 1,
X21 may be the same as described herein,
*″ indicates a binding site to ring CY1 in Formula 2A, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, a group represented by
in Formula 2A in the organometallic compound represented by Formula 1 may be a group represented by one of Formulae CY2-1 to CY2-6,
a) X1 in Formula 2B may be Si, R12 in Formula 2B may not be hydrogen and a methyl group, and the number of N(s) among T1 to T8 in Formulae CY2-1 to CY2-6 may be 0,
b) X1 in Formula 2B may be Si or Ge, R12 in Formula 2B may be hydrogen, a methyl group, or a deuterated methyl group, and the number of N(s) among T1 to T8 in Formulae CY2-1 to CY2-6 may be 0,
c) X1 in Formula 2B may be Si or Ge, R12 in Formula 2B may be hydrogen, a methyl group, or a deuterated methyl group, and the number of N(s) among T3 to T8 in Formulae CY2-1 and CY2-6 may be 1,
d) X1 in Formula 2B may be Si or Ge, R12 in Formula 2B may be hydrogen, a methyl group, or a deuterated methyl group, and the number of N(s) among T1, T2, T5, T6, T7 and T8 in Formulae CY2-2 and CY2-5 may be 1, or
e) X1 in Formula 2B may be Si or Ge, R12 in Formula 2B may be hydrogen, a methyl group, or a deuterated methyl group, and the number of N(s) among T1, T4, T5, T6, T7 and T8 in Formulae CY2-3 and CY2-4 may be 1.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(6):
wherein, in Formulae CY2(1) to CY2(6),
T21 may be N, C(Z21), or C(Ar21), T22 may be N, (Z22), or C(Ar22), T23 may be N, C(Z23), or C(Ar23), T24 may be N, C(Z24), or C(Ar24), T25 may be N, C(Z25), or C(Ar25), T26 may be N, C(Z26), or C(Ar26), T27 may be N, C(Z27), or C(Ar27), and T28 may be N, C(Z28), or C(Ar28),
the number of N(s) among T3 to T8 in Formulae CY2-1 and CY2-6 may be 0 or 1, the number of N(s) among T1, T2, T5, T6, T7, and T8 in Formulae CY2-2 and CY2-5 may be 0 or 1, the number of N(s) among T1, T4, T5, T6, T7, and T8 in Formulae CY2-3 and CY2-4 may be 0 or 1,
X21 may be the same as described herein,
Z21 to Z28 may each be the same as described in connection with Z2 provided herein,
Ar21 to Ar28 may each be the same as described in connection with Are provided herein,
Formulae CY2-1 and CY2-6 may include at least one of Ar23 to Ar28, Formulae CY2-2 and CY2-5 may include at least one of Ar21, Ar22, Ar25, Ar26, Ar27, and Ar28, and Formulae CY2-3 and CY2-4 may include at least one of Ar21, Ar24, Ar25, Ar26, Ar27, and Ar28,
*″ indicates a binding site to ring CY1 in Formula 2A, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(6), and at least one of Conditions 1-1 to 1-8 may be satisfied:
Condition 1-1
Condition 1-2
Condition 1-3
Condition 1-4
Condition 1-5
Condition 1-6
Condition 1-7
Condition 1-8
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(6), and at least one of Conditions 2-1 to 2-8 may be satisfied:
Condition 2-1
Condition 2-2
Condition 2-3
Condition 2-4
Condition 2-5
Condition 2-6
Condition 2-7
Condition 2-8
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(6), and one of Conditions 3-1 to 3-9 may be satisfied:
Condition 3-1
Condition 3-2
Condition 3-3
Condition 3-4
Condition 3-5
Condition 3-6
Condition 3-7
Condition 3-8
Condition 3-9
In one or more embodiments, a group represented by Formula CY2(1) may be a group represented by one of Formulae CY2(1)-1 to CY2(1)-4, a group represented by Formula CY2(2) may be a group represented by one of Formulae CY2(2)-1 to CY2(2)-4, a group represented by Formula CY2(3) may be a group represented by one of Formulae CY2(3)-1 to CY2(3)-3, a group represented by Formula CY2(4) may be a group represented by one of Formulae CY2(4)-1 to CY2(4)-3, a group represented by Formula CY2(5) may be a group represented by one of Formulae CY2(5)-1 to CY2(5)-4, and a group represented by Formula CY2(6) may be a group represented by one of Formulae CY2(6)-1 to CY2(6)-4:
wherein, in Formulae CY2(1)-1 to CY2(1)-4, CY2(2)-1 to CY2(2)-4, CY2(3)-1 to CY2(3)-3, CY2(4)-1 to CY2(4)-3, CY2(5)-1 to CY2(5)-4, and CY2(6)-1 to CY2(6)-4,
T21 to T28, X21, *″, and *′ may respectively be understood by referring to the descriptions of T21 to T28, X21, *″, and *′ in Formulae CY2(1) to CY2(6) provided herein,
ring CY20a may be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
R10a may be the same as described herein, and
aa may be an integer from 0 to 10.
In one or more embodiments, ring CY20a may be a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.
In one or more embodiments, in Formula 2A, a group represented by
may be a group represented by one of Formulae CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, and CY2-6-1 to CY2-6-65:
wherein, in Formulae CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, and CY2-6-1 to CY2-6-65,
X21 may be the same as described herein,
Z21 to Z28 may each be the same as described in connection with Z2 provided herein, wherein Z21 to Z28 may not each be hydrogen,
Ar21 to Ar28 may each be the same as described in connection with Ar2 provided herein,
*″ indicates a binding site to ring CY1 in Formula 2A, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, in Formula 2B, a group represented by
may be a group represented by one of Formulae CY14-1 to CY14-64:
wherein, in Formulae CY14-1 to CY14-64,
X14a may be O, S, N, C, or Si,
*″ indicates a binding site to a carbon atom in an adjacent pyridine ring in Formula 2B, and
*′ indicates a binding site to M in Formula 1.
Each of a carbon and X14a in Formulae CY14-1 to CY14-64 may be unsubstituted or substituted with R14 as described herein.
In one or more embodiments, in Formula 2B, a group represented by
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 may each be the same as described in connection with R14 provided herein, wherein R14a to R14d may not each be hydrogen,
X14 may be C(R1)(R2), N(R1), O, S, or Si(R1)(R2),
R1 to R8 may each be the same as described in connection with Ru provided herein,
*″ indicates a binding site to a carbon atom in an adjacent pyridine ring in Formula 2B, and
*′ indicates a binding site to M in Formula 1.
In one or more embodiments, the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1 or 2.
In one or more embodiments, the organometallic compound may be one of Compounds 1 to 5140:
In the organometallic compound represented by Formula 1, L1 may be a ligand represented by Formula 2A, n1, i.e., the number of L1(s), may be 1 or 2, L2 may be a ligand represented by Formula 2B, n2, i.e., the number of L2(s) may be 1 or 2, and L1 and L2 may be different from each other. That is, the organometallic compound may be heteroleptic complex that may essentially include, as ligands bound to metal M, at least one ligand represented by Formula 2A and at least one ligand represented by Formula 2B.
In Formula 1, a group represented by *—X1(R21)(R22)(R23) may be bound to the 5′-position of a pyridine ring in the ligand represented by Formula 2B (see Formula 2B). Accordingly, the organometallic compound including the ligand represented by Formula 2B may have excellent heat resistance and decomposition resistance. Therefore, an electronic device, e.g., an organic light-emitting device, including the organometallic compound may have excellent stability and long lifespan upon manufacture, storage, and/or driving.
Ar2 in Formula 2A of Formula 1 may be ring CY2 unsubstituted or substituted with at least one Z0, and ring CY2 may be an unsaturated C5-C30 carbocyclic group or an unsaturated C1-C30 heterocyclic group, and d2, i.e., the number of Ar2, may be an integer from 1 to 6. Thus, the organometallic compound represented by Formula 1 may have improved optical orientation characteristics, and the organometallic compound represented by Formula 1 may have a relatively narrow full width at half maximum (FWHM) of an emission spectrum or electroluminescence spectrum, and accordingly, an electronic device, e.g., an organic light-emitting device, including the organometallic compound may have improved emission efficiency.
In addition, the number of N(s) among T1 to T8 in Formula 2A of Formula 1 may be 0 or 1. Thus, the organometallic compound represented by Formula 1 may have stable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels, which lead to improved lifespan of an electronic device, e.g., an organic light-emitting device, including the organometallic compound.
The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, lowest excited singlet (S1) energy level, and lowest excited triplet (T1) energy level in electron volts (eV) of selected organometallic compounds represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimization at the B3LYP level. The results thereof are shown in Table 1.
Referring to the results of Table 1, the organometallic compound represented by Formula 1 was found to have suitable electrical characteristics for use as a dopant in an electronic device, e.g., an organic light-emitting device.
A method of synthesizing the organometallic compound represented by Formula 1 may be apparent to one of ordinary skill in the art by referring to Synthesis Examples provided herein.
The organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, e.g., as a dopant in the organic layer. Thus, according to another aspect, there is provided an organic light-emitting device that may include a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.
Since the organic light-emitting device has an organic layer including the organometallic compound represented by Formula 1, the organic light-emitting device may have a high external quantum efficiency and high lifespan characteristics.
The organometallic compound represented by Formula 1 may be used in a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this embodiment, the organometallic compound may serve as a dopant and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 may be smaller than that of the host). The emission layer, for example, may emit green light or blue light.
As used herein, the expression the “(organic layer) includes at least one organometallic compound” may be construed as meaning the “(organic layer) may include one organometallic compound of Formula 1 or two different organometallic compounds of Formula 1”.
For example, Compound 1 may only be included in the organic layer as an organometallic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, Compounds 1 and 2 may be included in the organic layer as organometallic compounds. In this embodiment, Compounds 1 and 2 may both be included in the same layer (for example, both Compounds 1 and 2 may be included in the emission layer).
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode. In one or more embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term “organic layer” as used herein refers to a single and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes including metals.
A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.
The first electrode 11 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material with a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 110 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like.
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. In one or more embodiments, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO.
The organic layer 15 may be on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
The hole transport region may include a hole injection layer only or a hole transport layer only. In one or more embodiments, the hole transport region may include a hole injection layer and a hole transport layer which are sequentially stacked on the first electrode 11. In one or more embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer, which are sequentially stacked on the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (A/sec) to about 100 Å/sec, though the conditions may vary depending on a compound that is used as a hole injection material and a structure and thermal properties of a desired hole injection layer.
When a hole injection layer is formed by spin coating, the spin coating may be performed at a coating rate in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and at a temperature in a range of about 80° C. to 200° C., to facilitate removal of a solvent after the spin coating, though the conditions may vary depending on a compound that is used as a hole injection material and a structure and thermal properties of a desired hole injection layer.
The conditions for forming a hole transport layer and an electron blocking layer may be inferred from the conditions for forming the hole injection layer.
The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor-sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof:
wherein, in Formula 201, Ar101 and Ar102 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alky 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, or a combination thereof.
In Formula 201, xa and xb may each independently be an integer from 0 to 5. In one or more embodiments, xa and xb may each independently be an integer from 0 to 2. In one or more embodiments, xa may be 1, and xb may be 0.
In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, or a hexyl group), or a C1-C10 alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group);
a C1-C10 alkyl group or a C1-C10 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof; or
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, or a combination thereof.
In Formula 201, R109 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A:
wherein, in Formula 201A, R101, R111, R112, and R109 may respectively be understood by referring to the descriptions of R101, R111, R112, and R109 provided herein.
In one or more embodiments, the hole transport region may include one or more of Compounds HT1 to HT20:
The thickness of the hole transport region may be in a range of about 100 (Angstroms) Å to about 10,000 Å, and in one or more embodiments, 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 combination thereof, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, and in one or more embodiments, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in one or more embodiments, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.
The charge generating material may include, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or a combination thereof. In one or more embodiments, the p-dopant may be a quinone derivative, such as tetracyanoquinodimethane (TCNQ), a 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; a compound containing a cyano group, such as Compound HT-D1; or a combination thereof:
The hole transport region may further include a buffer layer.
The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.
When the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include the material for forming a hole transport region, the host material described herein, or a combination thereof. In one or more embodiments, when the hole transport region includes an electron blocking layer, mCP, Compound H-H1, etc. as described herein, or the like, may be used for forming the electron blocking layer.
An emission layer may be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, vacuum deposition and coating conditions for forming the emission layer may be generally similar to those conditions for forming a hole injection layer, though the conditions may vary depending on a compound that is used.
The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 described herein.
The host may include TPBi, TBADN, ADN (also known as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-E43, or a combination thereof.
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, the emission layer may have a structure in which the red emission layer, the green emission layer, and/or the blue emission layer are layered to emit white light. In one or more embodiments, the structure of the emission layer may vary.
When the emission layer includes the host and the dopant, an amount of the dopant may be selected from a range of about 0.01 parts to about 15 parts by weight based on about 100 parts by weight of the host.
The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in one or more embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
Next, an electron transport region may be formed 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.
In one or more embodiments, the electron transport region may have a hole blocking layer/an electron transport layer/an electron injection layer structure or an electron transport layer/an electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
The conditions for forming a hole blocking layer, an electron transport layer, and an electron injection layer may be inferred based on the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof:
The thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, and in one or more embodiments, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or a combination thereof:
In one or more embodiments, the electron transport layer may include one or more of Compounds ET1 to ET25:
The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in one or more embodiments, about 150 Å to about 500 Å.
When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include a material containing metal, in addition to the materials described above.
The material containing metal may include a Li complex. The Li complex may include, e.g., Compound ET-D1 or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a material with a relatively low work function, such as a metal, an alloy, an electrically conductive compound, or any combination thereof. Examples of the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In one or more embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top emission light-emitting device. In one or more embodiments, the material for forming the second electrode 19 may vary.
Hereinbefore the organic light-emitting device 10 has been described with reference to
According to an aspect of another embodiment, an electronic apparatus may include the organic light-emitting device. Thus, an electronic apparatus including the organic light-emitting device may be provided. The electronic apparatus may include, for example, a display, lighting, a sensor, or the like.
According to an aspect of still another embodiment, a diagnostic composition may include at least one organometallic compound represented by Formula 1.
Since the organometallic compound represented by Formula 1 provides high luminescence efficiency, the diagnostic efficiency of the diagnostic composition that includes the organometallic compound represented by Formula 1 may be excellent.
The diagnostic composition may be applied in various ways, such as in a diagnostic kit, a diagnostic reagent, a biosensor, or a biomarker.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group as used herein may include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. In one or more embodiments, Formula 9-33 may be a branched C6 alkyl group. Formula 9-33 may be a tert-butyl group substituted with two methyl groups.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by -OA101 (wherein A101 is a C1-C1 alkyl group). Examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
The term “C2-C60 alkenyl group” as used herein refers to a group formed by placing at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a group formed by placing at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group. Examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent 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 as used herein include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl (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 cyclic group having 1 to 10 carbon atoms and at least one heteroatom of N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group as used herein may include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, or a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole is non-aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group including at least one heteroatom of N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C2-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C2-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include a plurality of rings, the plurality of rings may be fused to each other.
The term “C7-C60 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 a heterocyclic aromatic system having at least one heteroatom of N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom of N, O, P, Si, S, Se, Ge and B as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include a plurality of rings, the plurality of rings may be fused to each other.
The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group. The term “C7-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 is represented by -OA102 (wherein A102 is the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein is represented by —SA103 (wherein A103 is the C6-C60 aryl group). The term “C1-C60 alkylthio group” as used herein is represented by -SA104 (wherein A104 is the C1-C60 alkyl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and only carbon atoms (e.g., the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and a heteroatom selected from N, O, P, Si, S, Se, Ge, and B and carbon atoms (e.g., the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 5 to 30 carbon atoms only as ring-forming atoms. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. The term “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a (or at least one Z0)” may include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (a 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, or a fluorene group, each (unsubstituted or substituted with at least one R10a (or at least one Z0)).
The term “C1-C30 heterocyclic group” as used herein refers to saturated or unsaturated cyclic group including 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a (or at least one Z0))” may include a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophenegroup, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R10a (or at least one Z0)).
Examples of the “C5-C30 carbocyclic group” and the “C1-C30 heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring and at least one second ring are condensed,
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 isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and
wherein 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 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 refer to a C1-C60 alkyl group (or C1-C20 alkyl group or the like), C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). Examples of the “fluorinated C1 alkyl group (i.e., a fluorinated methyl group)” may include —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group”, or “fluorinated phenyl group” may respectively be: i) a fully fluorinated C1-C60 alkyl group (or fully fluorinated C1-C20 alkyl group or the like), fully fluorinated C3-C10 cycloalkyl group, fully fluorinated C1-C10 heterocycloalkyl group, or fully fluorinated phenyl group, in which all hydrogen atoms are substituted with fluoro groups; or ii) a partially fluorinated C1-C60 alkyl group (or partially fluorinated C1-C20 alkyl group or the like), partially fluorinated C3-C10 cycloalkyl group, partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, in which some of hydrogen atoms are substituted with fluoro groups.
The “deuterated C1-C60 alkyl group (or deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated heterocycloalkyl group”, and “deuterated phenyl group” as used herein may respectively be a C1-C60 alkyl group (or C1-C20 alkyl group or the like), C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. Examples of the “deuterated C1 alkyl group (i.e., a deuterated methyl group)” may include -CD3, —CD2H, and -CDH2. Examples of the “deuterated C3-C10 cycloalkyl group” may include Formula 10-501. The “deuterated C1-C60 alkyl group (or deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated heterocycloalkyl group”, or deuterated phenyl group may respectively be: i) a fully deuterated C1-C60 alkyl group (or fully deuterated C1-C20 alkyl group or the like), fully deuterated C3-C10 cycloalkyl group, fully deuterated heterocycloalkyl group, or fully deuterated phenyl group, in which all hydrogen atoms are substituted with deuterium atoms; or ii) a partially deuterated C1-C60 alkyl group (or partially deuterated C1-C20 alkyl group or the like), partially deuterated C3-C10 cycloalkyl group, partially deuterated heterocycloalkyl group, or partially deuterated phenyl group, in which some of hydrogen atoms are substituted with deuterium atoms.
The term “(C1-C20 alkyl) ‘X’ group” as used herein refers to a ‘X’ group 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 “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. Examples of the (C1 alkyl)phenyl group may include a toluyl group.
In the present specification, “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” each refer to a hetero ring in which at least one ring-forming carbon atom is substituted with nitrogen atom and respectively having an identical backbone as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group”.
At least one 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 C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, 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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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), —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 C2-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 deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39), or
a combination thereof.
In the present specification, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C1-C60 alkylthio group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, or a C6-C60 aryl group; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 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, or a combination thereof.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2,
an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
Hereinafter, a compound and an organic light-emitting device according to one or more exemplary embodiments will be described in further detail with reference to Synthesis Examples and Examples, however, the present disclosure is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used based on molar equivalence.
7.9 grams (g) (27.8 millimoles (mmol)) of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine and 4.4 g (12.6 mmol) of iridium chloride hydrate were mixed with 120 milliliters (mL) of ethoxyethanol and 40 mL of deionized (DI) water. Then, the mixture was stirred under reflux for 24 hours, and then the temperature was allowed to cool to room temperature. A solid was formed therefrom, and then separated by filtration. The solid was sufficiently washed with water, methanol, and hexane in the stated order, and dried in a vacuum oven to thereby obtain 7.6 g of Compound 65A (yield: 76%).
3.3 g (2.1 mmol) of Compound 65A was mixed with 90 mL of methylene chloride, and a solution, in which 1.1 g (4.1 mmol) of silver trifluoromethanesulfonate (silver triflate, AgOTf) was dissolved in 30 mL of methanol, was added thereto. Then, the mixture was stirred for 18 hours at room temperature while blocking light by using an aluminum foil. The resultant was celite-filtered to remove a solid formed therefrom and filtered under reduced pressure to thereby obtain a solid (Compound 65B). The solid was used in the following reaction without any further purification.
4.0 g (4.1 mmol) of Compound 65B and 1.7 g (4.5 mmol) of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine were mixed with 40 mL of ethanol and stirred under reflux for 18 hours, followed by reducing the temperature. The solvent was removed from the obtained mixture under reduced pressure to obtain a solid that was subjected to column chromatography (eluent: methylene chloride (MC) and hexane) to thereby obtain 1.8 g of Compound 65 (yield: 39%). The resulting compound was identified by using mass spectrometry (high resolution mass spectrometry using matrix assisted laser desorption ionization, HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.
HRMS (MALDI) calcd for C63H70IrN3OSi2: m/z 1133.4687 Found: 1133.4681.
7.2 g of Compound 206A (yield: 72%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 206B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 206A was used instead of Compound 65A. The resulting Compound 206B was used in the following reaction without any further purification.
1.4 g of Compound 206 (yield: 33%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 206B was used instead of Compound 65B, and 4-neopentyl-2-(8-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS(MALDI) calcd for C66H76IrN3OSi2: m/z 1175.5156 Found: 1175.5162.
8.1 g of Compound 363A (yield: 81%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 363B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 363A was used instead of Compound 65A. The resulting Compound 363B was used in the following reaction without any further purification.
1.2 g of Compound 363 (yield: 29%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 363B was used instead of Compound 65B, and 2-(7-(4-fluorophenyl)dibenzo[b,d]furan-4-yl)-4-isopropylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectroscopy and HPLC analysis.
HRMS (MALDI) calcd for C54H51FIrN3OSi2: m/z 1025.3184 Found: 1025.3189.
1.7 g of Compound 556 (yield: 36%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 206B was used instead of Compound 65B, and 5-(methyl-d3)-4-neopentyl-2-(8-phenyldibenzo[b,d]furan-2-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C67H75D3IrN3OSi2: m/z 1192.5501 Found: 1192.5496.
1.1 g of Compound 749 (yield: 27%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that 4-(cyclohexylmethyl)-2-(7-phenyldibenzo[b,d]thiophen-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C66H74IrN3SSi2: m/z 1189.4771 Found: 1189.4763.
8.8 g of Compound 2350A (yield: 88%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 4-(methyl-d3)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (yield: 88%).
Compound 2350B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2350A was used instead of Compound 65A. The resulting Compound 2350B was used in the following reaction without any further purification.
2.1 g of Compound 2350 (yield: 45%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2350B was used instead of Compound 65B, and 2-(7-phenyldibenzo[b,d]furan-4-yl)-4-(phenylmethyl-d2)pyridine was used instead of 2-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C60H48D8IrN3OSi2: m/z 1091.4093 Found: 1091.4090.
6.7 g of Compound 2508A (yield: 67%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 2-(2-fluoro-4-(methyl-d3)phenyl)-4-(phenylmethyl-d2)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 2508B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2508A was used instead of Compound 65A. The resulting Compound 2508B was used in the following reaction without further purification.
1.3 g of Compound 2508 (yield: 26%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2508B was used instead of Compound 65B, and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-(methyl-d3)phenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C73H57D15F2IrN3OSi2: m/z 1308.5753 Found: 1308.5760.
8.3 g of Compound 2566A (yield: 83%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 2-(4-(methyl-d3)phenyl)-4-(propan-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 2566B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2566A was used instead of Compound 65A. The resulting Compound 2566B was used in the following reaction without any further purification.
1.5 g of Compound 2566 (yield: 34%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2566B was used instead of Compound 65B, and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-fluorophenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C64H61D10FIrN3OSi2: m/z 1175.5377 Found: 1175.5383.
8.4 g of Compound 2579A (yield: 84%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 2-([1,1′-biphenyl]-3-yl)-4-(propan-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 2579B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2579A was used instead of Compound 65A. The resulting Compound 2579B was used in the following reaction without any further purification.
1.1 g of Compound 2579 (yield: 25%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2579B was used instead of Compound 65B, and 4-(cyclopentylmethyl-d2)-2-(7-(2,6-dimethylphenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C77H76IrN3OSi2: m/z 1315.5720 Found: 1315.5711.
7.2 g of Compound 2758A (yield: 72%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 4-(methyl-d3)-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 2758B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2758A was used instead of Compound 65A. The resulting Compound 2758B was used in the following reaction without any further purification.
1.6 g of Compound 2758 (yield: 37%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2758B was used instead of Compound 65B, and 5-(methyl-d3)-4-phenyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C60H47D9Ge2IrN3O: m/z 1184.3041 Found: 1184.3033.
0.9 g of Compound 485 (yield: 27%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that 2-(1,7-diphenyldibenzo[b,d]furan-4-yl)-4-isobutylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C69H74IrN3OSi2: m/z 1209.5000 Found: 1209.4992.
1.0 g of Compound 487 (yield: 32%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that 2-(7-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-4-yl)-4-isopropylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C68H72IrN3OSi2: m/z 1195.4843 Found: 1195.4840.
6.5 g of Compound 1703A (yield: 65%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 1703B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 1703A was used instead of Compound 65A. The resulting Compound 1703B was used in the following reaction without any further purification.
2.1 g of Compound 1703 (yield: 45%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 1703B was used instead of Compound 65B, and 4-isopropyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C54H52Ge2IrN3O: m/z 1099.2163 Found: 1099.2156.
3.6 g of Compound 2866A (yield: 72%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 4-neopentyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound 2866B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound 2866A was used instead of Compound 65A. The resulting Compound 2866B was used in the following reaction without further purification.
0.5 g of Compound 2866 (yield: 24%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 2866B was used instead of Compound 65B, and 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C75H74IrN3O2Si: m/z 1269.5180 Found: 1269.5188.
0.5 g of Compound A1 (yield: 42%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound 363B was used instead of Compound 65B, and 2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C46H44IrN3OSi2: m/z 903.2652 Found: 903.2645.
3.4 g of Compound A2A (yield: 86%) was obtained in substantially the same manner as in Synthesis of Compound 65A in Synthesis Example 1, except that 4-methyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.
Compound A2B was obtained in substantially the same manner as in Synthesis of Compound 65B in Synthesis Example 1, except that Compound A2A was used instead of Compound 65A. The resulting Compound A2B was used in the following reaction without further purification.
0.3 g of Compound A2 (yield: 41%) was obtained in substantially the same manner as in Synthesis of Compound 65 in Synthesis Example 1, except that Compound A2B was used instead of Compound 65B, and 2-(dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was identified by using mass spectrometry and HPLC analysis.
HRMS (MALDI) calcd for C47H46IrN3OSi2: m/z 917.2809 Found: 917.2801.
A glass substrate, on which an ITO as an anode was patterned, was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated in isopropyl alcohol and deionized water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Subsequently, the resultant glass substrate was mounted on a vacuum-deposition device.
Compounds HT3 and F6-TCNNQ were co-deposited by vacuum on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å, and Compound H-H1 was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 300 Å.
Subsequently, Compound H-H1, Compound H-E43 and Compound 65 (dopant) were co-deposited on the electron blocking layer at a weight ratio of 57:38:5 to form an emission layer having a thickness of 400 Å.
Then, Compound ET3 and ET-D1 were codeposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å. ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al was deposited on the electron injection layer to form a cathode having a thickness of 1000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of Compound 65 as a dopant in the formation of an emission layer.
The maximum value of external quantum efficiency (Max EQE, %), and lifespan (LT97, hours (hr)) of each organic light-emitting device manufactured in Examples 1 to 14 and Comparative Examples A1 and A2 were evaluated. The results thereof are shown in Table 2. A Keithley 2400 current voltmeter and a luminance meter (Minolta Cs-1000A) were used in the evaluation. The lifespan (T97) refers to the time (hr) required for the initial luminance of 16,000 candela per square meter (cd/m2, or nits) of the organic light-emitting device to reduce by 97% and is indicated as a relative value (%).
Referring to the results of Table 2, the organic light-emitting device of Examples 1 to 14 were found to have improved external quantum efficiency and lifespan, as compared with the organic light-emitting devices of Comparative Examples A1 and A2.
As provided in the foregoing detailed description and examples, the organometallic compound may have excellent electrical characteristics and heat resistance, and thus, an electronic device, e.g., an organic light-emitting device, including at least one organometallic corn pound may have improved external quantum efficiency (EQE) and excellent lifespan characteristics. Accordingly, by using the at least one organometallic compound, an organic light-emitting device with excellent quality and an electronic apparatus including the organic light-emitting device may be realized.
It should be understood that the one or more exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described in further detail 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 |
|---|---|---|---|
| 10-2020-0060898 | May 2020 | KR | national |
| 10-2021-0064010 | May 2021 | KR | national |
