Patent Application
20220127290
This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0141452, filed on Oct. 28, 2020, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated by reference herein in its entirety.
One or more embodiments that relate to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device are described herein.
Organic light-emitting devices (OLEDs) are self-emission devices that have improved characteristics compared to conventional devices, including wider viewing angles, faster response times, excellent brightness, driving voltage, and response speed, and the OLEDs produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons may then transition from an excited state to a ground state to thereby generate light, for example, visible light.
One or more embodiments relate to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect, provided is an organometallic compound represented by Formula 1.
wherein, in Formula 1,
M is a transition metal,
X1 to X4 in Formula 1 are each independently C or N,
X5 in Formula 1 is O, S, N(R′), C(R′)(R″), or C(═O),
wherein,
T1 to T4 in Formula 1 may each independently be a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*, *—C(R5a)═*′, *═C(R5a)—*, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
n1 to n4 in Formula 1 may each independently be 0 or 1, wherein at least three of n1 to n4 may each be 1,
when n1 in Formula 1 is 0, T1 is not present, when n2 in Formula 1 is 0, T2 is not present, when n3 in Formula 1 is 0, T3 is not present, and when n4 in Formula 1 is 0, T4 is not present,
Z1 to Z4 in Formula 1 may each independently be a group represented by Formula 51,
d1 to d4 in Formula 1 are each independently an integer from 0 to 20,
L1 to L4 and L51 in Formulae 1 and 51 are each independently a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
b1 to b4 and b51 in Formulae 1 and 51 are each independently an integer from 1 to 10,
R1 to R4, R5a, R5b, R′, R″, and Q51 to Q53 in Formulae 1 and 51 are each independently a group represented by Formula 51, hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), and
provided that none of Q51 to Q53 is a group represented by Formula 51,
at least one of Q51 to Q53 in Formula 51 may each independently be a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
c1 to c4 and a1 to a4 in Formula 1 may each independently be an integer from 0 to 20,
c51 in Formula 51 may be an integer from 1 to 20,
Formula 1 may satisfy at least one of Condition 1 and Condition 2,
two or more of a plurality of R1(s) in Formula 1 are optionally bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of R2(s) in Formula 1 are optionally bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of R3(s) in Formula 1 are optionally bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of R4(s) in Formula 1 are optionally bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R1 to R4, R5a and one or more of R1 to R4, R5b and one or more of R1 to R4, or R5a and R5b are each optionally bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R10a are as defined in connection with R1,
* and *′ each indicate a binding site to a neighboring atom, and
the substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof,
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a 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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a 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 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 which is 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 C1-C10 heterocycloalkenyl group; a C6-C60 aryl group which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a heteroaryloxy group; a C1-C60 heteroarylthio group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
According to another aspect, provided is an organic light-emitting device including a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organometallic compound represented by Formula 1.
According to another aspect, provided is an electronic apparatus including the organic light-emitting device.
The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may act as a dopant.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawing, in which
FIGURE is a schematic cross-sectional view of an organic light-emitting device according to aspects of one or more embodiments.
Reference will now be made in detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing, wherein like reference numerals refer to like elements throughout. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the exemplary embodiments are described below, by referring to the FIGURE, to explain one or more 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 aspect of the present disclosure provides an organometallic compound represented by Formula 1:
wherein M in Formula 1 is a transition metal.
In one or more embodiments, M may be Period 1 transition metal, Period 2 transition metal, or Period 3 transition metal of Periodic Table Elements.
In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), palladium (Pd), or gold (Au).
In one or more embodiments, M in Formula 1 may be Pt, Pd, or Au.
X1 to X4 in Formula 1 may each independently be C or N.
In one or more embodiments, X1 and X3 in Formula 1 may be C, and X2 and X4 in Formula 1 may be N.
X5 in Formula 1 is O, S, N(R′), C(R′)(R″), or C(═O).
The bond between X5 and M in Formula 1 may be a covalent bond.
One of a bond between X2 and M in Formula 1, a bond between X3 and M in Formula 1, and a bond between X4 and M in Formula 1 may be a covalent bond, and the other two may each be a coordinate bond.
In one or more embodiments, a bond between X2 and M in Formula 1 may be a coordinate bond.
In one or more embodiments, a bond between X5 and M in Formula 1 and a bond between X3 and M in Formula 1 may each be a covalent bond, and a bond between X2 and M in Formula 1 and a bond between X4 and M in Formula 1 may each be a coordinate bond.
Ring CY1 to ring CY4 in Formula 1 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, ring CY1 to ring CY4 in Formula 1 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other,
the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
In one or more embodiments, ring CY1 to ring CY4 in Formula 1 may each independently be a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In one or more embodiments, ring CY1 and ring CY3 may each independently be:
a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzothiophene group, or a dibenzofuran group; or
a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzothiophene group, or a dibenzofuran group, each condensed with a cyclohexane group, a cyclohexene group, a norbornane group, or a combination thereof.
In one or more embodiments, X2 may be N, and ring CY2 may be:
a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group; or
a benzimidazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, each condensed with a cyclohexane group, a cyclohexene group, a norbornane group, or a combination thereof.
In one or more embodiments, ring CY4 may be:
a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group; or
a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group, each condensed with a cyclohexane group, a cyclohexene group, a norbornane group, or a combination thereof.
T1 to T4 in Formula 1 may each independently be a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5a)═*′, *═C(R5a)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, T1 and T2 in Formula 1 may each be a single bond, and T3 in Formula 1 may be a single bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, or *—O—*′.
Each of n1 to n4 in Formula 1 indicate a number for each of T1 to T4, respectively, and are each independently 0 or 1, wherein at least three of n1 to n4 may each be 1. In other words, a ligand of the organometallic compound represented by Formula 1 may be a tetradentate ligand. For example, a sum of n1 to n4 may be 3 or 4.
When n1 in Formula 1 is 0, T1 is not present, when n2 in Formula 1 is 0, T2 is not present, when n3 in Formula 1 is 0, T3 is not present, and when n4 in Formula 1 is 0, T4 is not present.
In one or more embodiments, n1 to n3 in Formula 1 may each be 1, and n4 in Formula 1 may be 0.
Z1 to Z4 in Formula 1 are each independently a group represented by Formula 51:
wherein Formula 51 is the same as described herein.
Each of d1 to d4 in Formula 1 indicates a number for each of Z1 to Z4, respectively, and are each independently an integer from 0 to 20. When d1 is 2 or more, two or more of Z1(s) are identical to or different from each other, when d2 is 2 or more, two or more of Z2(s) are identical to or different from each other, when d3 is 2 or more, two or more of Z3(s) are identical to or different from each other, and when d4 is 2 or more, two or more of Z4(s) are identical to or different from each other. In one or more embodiments, d1 to d4 may each independently be 0, 1, 2, or 3.
L1 to L4 and L51 in Formulae 1 and 51 are each independently a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 to L4 and L51 in Formulae 1 and 51 may each independently be:
a single bond, or
a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group, each unsubstituted or substituted with at least one R10a.
In one or more embodiments, L1 to L4 and L51 in Formulae 1 and 51 may each independently be:
a single bond, or
a benzene group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a.
Each of b1 to b4 and b51 in Formulae 1 and 51 may indicate a number for each of L1 to L4 and L51, respectively, and are each independently an integer from 1 to 10. When b1 is 2 or more, two or more of L1(s) may be identical to or different from each other, when b2 is 2 or more, two or more of L2(s) may be identical to or different from each other, when b3 is 2 or more, two or more of L3(s) may be identical to or different from each other, when b4 is 2 or more, two or more of L4(s) may be identical to or different from each other, and when b51 is 2 or more, two or more of L51(s) may be identical to or different from each other. In one or more embodiments, b1 to b4 and b51 may each independently be 1, 2, or 3.
R1 to R4, R5a, R5b, R′, R″, and Q51 to Q53 in Formulae 1 and 51 are each independently a group represented by Formula 51, hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), wherein at least one of Q51 to Q53 in Formula 51 are each independently a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Q1 to Q9 may each be the same as described in the present specification.
None of Q51 to Q53 is a group represented by Formula 51. In other words, each of Q51 to Q53 is not a group represented by Formula 51.
In one or more embodiments, R1 to R4, R′ and R″ Formula 1 and Q51 to Q53 may not be a group represented by Formula 51.
In one or more embodiments, R1 to R4, R5a, R5b, R′, R″, and Q51 to Q53 in Formulae 1 and 51 may each independently be:
a group represented by Formula 51, 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 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (a bicyclo[2.2.1]heptyl 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)bicyclo[2.2.1]heptyl 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, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated 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 deuterated phenyl group, a fluorinated 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, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or
—N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
wherein Q1 to Q9 may each independently be:
deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, —CD2CDH2, —CF3, —CF2H, —CFH2, —CH2CF3, —CH2CF2H, —CH2CFH2, —CHFCH3, —CHFCF2H, —CHFCFH2, —CHFCF3, —CF2CF3, —CF2CF2H, or —CF2CFH2; or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a C1-C10 alkyl group, a phenyl group, or a combination thereof,
provided that none of Q51 to Q53 is a group represented by Formula 51.
In one or more embodiments, R1 to R4, R5a, R5b, R′, and R″ in Formula 1 may each independently be:
a group represented by Formula 51, hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group that is 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 C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, or a combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl 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 C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof; or
—Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5).
In one or more embodiments, in Formula 51, Q51 to Q53 may each independently be:
hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group that is 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 C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, or a combination thereof; or
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl 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 C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof,
wherein at least one of Q51 to Q53 (for example, Q53) may be a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl 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 C1-C10 heterocycloalkyl group, a fluorinated C1-C10 heterocycloalkyl group, a (C1-C20 alkyl)C1-C10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C1-C20 alkyl)biphenyl group, or a combination thereof.
In one or more embodiments, in Formula 51, i) Q51 and Q52 may each independently be hydrogen or deuterium, ii) Q51 may be hydrogen or deuterium, and Q52 may be neither hydrogen nor deuterium, or iii) both of Q51 and Q52 may be neither hydrogen nor deuterium.
In one or more embodiments, R1 to R4, R5a, R5b, R′, R″, and Q51 to Q53 in Formulae 1 and 51 may each independently be a group represented by Formula 51, hydrogen, deuterium, —F, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C2-C10 alkenyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-227, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-129, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5) (wherein Q3 to Q5 may each be the same as described in the present specification), and provided that none of Q51 to Q53 is a group represented by Formula 51.
In one or more embodiments, in Formula 51, Q51 and Q52 may each independently be hydrogen or deuterium, and Q53 may be a group represented by one of Formulae 10-12 to 10-129, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F.
In one or more embodiments, in Formula 51, Q51 may be hydrogen or deuterium, and Q52 may be —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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, or a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, and Q53 may be a group represented by one of Formulae 10-12 to 10-129, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F.
In one or more embodiments, in Formula 51, Q51 and Q52 may each independently be —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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, or a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, and Q53 may be a group represented by one of Formulae 10-12 to 10-129, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F.
In one or more embodiments, at least one of Q51 to Q53 in Formula 51 (for example, one of Q51 to Q53) may be a group represented by one of Formulae 10-12 to 10-129, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-12 to 10-129 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F:
wherein * in Formulae 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350 indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:
The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-227 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:
The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium” and “the group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:
The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with —F” and “the group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-617:
wherein c1 to c4 and a1 to a4 in Formula 1 may indicate numbers of R1 to R4, a group represented by *-[(L1)b1-(R1)c1], a group represented by *-[(L2)b2-(R2)c2], a group represented by *-[(L3)b3-(R3)c3], and a group represented by *-[(L4)b4-(R4)c4], respectively, and may each independently be an integer from 0 to 20. When c1 is 2 or more, two or more of R1(s) may be identical to or different from each other, when c2 is 2 or more, two or more of R2(s) may be identical to or different from each other, when c3 is 2 or more, two or more of R3(s) may be identical to or different from each other, when c4 is 2 or more, two or more of R4(s) may be identical to or different from each other, when a1 is 2 or more, two or more of groups represented by *-[(L1)b1-(R1)c1] may be identical to or different from each other, when a2 is 2 or more, two or more of groups represented by *-[(L2)b2-(R2)c2] may be identical to or different from each other, when a3 is 2 or more, two or more of groups represented by *-[(L3)b3-(R3)c3] may be identical to or different from each other, and when a4 is 2 or more, two or more of groups represented by *-[(L4)b4-(R4)c4] may be identical to or different from each other. In one or more embodiments, c1 to c4 and a1 to a4 in Formula 1 may each independently be 0, 1, 2, or 3.
c51 in Formula 51 may indicate the number of groups represented by *—C(Q51)(Q52)(Q53) and may be an integer from 1 to 20. When c51 is 2 or more, two or more groups represented by *—C(Q51)(Q52)(Q53) may be identical to or different from each other. In one or more embodiments, c51 may be 1 or 2.
The organometallic compound represented by Formula 1 may satisfy at least one of Condition 1 and Condition 2:
Condition 1
the sum of d1 to d4 in Formula 1 is 1 or more
Condition 2
at least one of T1 to T4 in Formula 1 is *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—C(R5a)═*′, *═C(R5a)—*′, or *—C(R5a)═C(R5b)—*′, and
at least one of R5a and R5b is a group represented by Formula 51
In other words, the organometallic compound represented by Formula 1 may include at least one group represented by Formula 51.
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition 1A and Condition 2A:
Condition 1A
in Formula 1,
i) d1 is 1, and each of d2, d3, and d4 is 0;
ii) d2 is 1, and each of d1, d3, and d4 is 0;
iii) d3 is 1, and each of d1, d2, and d4 is 0;
iv) d4 is 1, and each of d1, d2, and d3 is 0;
v) each of d1 and d2 is 1, and each of d3 and d4 is 0;
vi) each of d2 and d3 is 1, and each of d1 and d4 is 0; or
vii) each of d2 and d4 is 1, and each of d1 and d3 is 0.
Condition 2A
in Formula 1, n3 is 1, and
i) T3 is *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)═*′, or *═C(R5a)—*′, and R5a is a group represented by Formula 51; or
ii) T3 is *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, or *—C(R5a)═C(R5b)—*, and at least one of R5a and R5b is a group represented by Formula 51, wherein * and *′ may each indicate a binding site to a neighboring atom.
In Formula 1, i) two or more of a plurality of R2(s) may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, ii) two or more of a plurality of R3(s) may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iii) two or more of a plurality of R4(s) may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, and iv) two or more of R1 to R4, one or more of R1 to R4 and R5a, one or more of R1 to R4 and R5b, or R5a and R5b may each optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.
R10a may be the same as described in connection with R1.
In one or more embodiments, a group represented by *—C(Q51)(Q52)(Q53) in Formula 51 may be a group represented by one of Formulae 51-1 to 51-25:
Q51 and Q52 in Formulae 51-1 to 51-25 may each be the same as described in the present specification, and Q61 to Q66 in Formulae 51-1 to 51-25 may each be the same as described in connection with R10a in the present specification, wherein each of Q61 to Q65 in Formulae 51-1 to 51-25 may not be hydrogen, and * in Formulae 51-1 to 51-25 indicates a binding site to L51 in Formula 51.
In one or more embodiments, in Formulae 51-1 to 51-20,
i) Q51 and Q52 may each be hydrogen, and Q61 to Q65 may each independently be deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or a (C1-C20 alkyl)phenyl group,
ii) Q51 may be hydrogen, and Q52 and Q61 to Q65 may each independently be deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or a (C1-C20 alkyl)phenyl group, or
iii) Q51, Q52, and Q61 to Q65 may each independently be deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or a (C1-C20 alkyl)phenyl group.
In one or more embodiments, L51 in Formula 51 may be a single bond.
In one or more embodiments, in a group represented by Formula 51, L51 may be a single bond, and thus, the group represented by Formula 51 may be a group represented by one of Formulae 51-1 to 51-25, for example, one of Formulae 51-1 to 51-20.
In one or more embodiments, a group represented by Formula 51 may be a group represented by one of Formulae 51(1) to 51(19):
T11 to T15 in Formulae 51(1) to 51(19) may each be a group represented by *—C(Q51)(Q52)(Q53) in Formula 51, T11 to T15 in Formulae 51(1) to 51(19) may be identical to or different from each other, R10a in Formulae 51(1) to 51(19) may be the same as described in connection with R1 in the present specification, and * in Formulae 51(1) to 51(19) indicates a binding site to a neighboring atom.
In one or more embodiments, in Formula 1, n1 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY1(1) to CY1(20):
In Formulae CY1(1) to CY1(20),
X1 may be the same as described in the present specification,
X19 may be O, S, N(R19a), C(R19a)(R19b), or Si(R19a)(R19b),
R19a and R19b may each be the same as described in connection with R1 in the present specification,
* indicates a binding site to X5 in Formula 1, and
*′ indicates a binding site to T1 in Formula 1.
In one or more embodiments, in Formula 1, n1 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY1-1 to CY1-18 and ZCY1-1 to ZCY1-32:
In Formulae CY1-1 to CY1-18 and ZCY1-1 to ZCY1-32,
X1 may be the same as described in the present specification,
R11 to R14 may each be the same as described in connection with R1 in the present specification, wherein each of R11 to R14 may not be hydrogen,
Z1 to Z14 may each be the same as described in connection with Z1 in the present specification,
* indicates a binding site to X5 in Formula 1, and
*′ indicates a binding site to T1 in Formula 1.
In one or more embodiments, in Formula 1, each of n1 and n2 may be 1, and ring CY2 may be a group represented by Formula CY2A or CY2B:
In Formulae CY2A and CY2B,
X2 and ring CY2 may each be the same as described in the present specification,
Y21 to Y23 may each independently be O, S, N, C, or Si,
a bond between X2 and Y21, a bond between X2 and Y22, a bond between X2 and Y23, and a bond between Y22 and Y23 may each be a chemical bond,
*′ indicates a binding site to T1 in Formula 1,
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to T2 in Formula 1.
In one or more embodiments, in Formula 1, each of n1 and n2 may be 1, and a group represented by
may be a group represented by one of Formulae CY2(1) to CY2(16):
In Formulae CY2(1) to CY2(16),
X2 may be the same as described in the present specification,
X29 may be O, S, N-[(L2)b2-(R2)c2], N(Z24), C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described in the present specification,
Z24 may be the same as described in connection with Z2 in the present specification,
R29a and R29b may each be the same as described in connection with R2 in the present specification,
*′ indicates a binding site to T1 in Formula 1,
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to T2 in Formula 1.
In one or more embodiments, in Formula 1, each of n1 and n2 may be 1, and a group represented by
may be a group represented by one of Formulae CY2-1 to CY2-16 and ZCY2-1 to ZCY2-19:
In Formulae CY2-1 to CY2-16 and ZCY2-1 to ZCY2-19,
X2 may be the same as described in the present specification,
X29 may be O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described in the present specification,
Z21 to Z24 may each be the same as described in connection with Z2 in the present specification,
R21 to R23, R29a, and R29b may each be the same as described in connection with R2 in the present specification, wherein each of R21 to R23 may not be hydrogen,
*′ indicates a binding site to T1 in Formula 1,
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to T2 in Formula 1.
In one or more embodiments, in Formula 1, each of n2 and n3 may be 1, and a group represented by
may be a group represented by one of Formulae CY3(1) to CY3(15):
In Formulae CY3(1) to CY3(15),
X3 may be the same as described in the present specification,
X39 may be O, S, N(Z39a), C(R39a)(R39b), or Si(R39a)(R39b),
R39a and R39b may each be the same as described in connection with R3 in the present specification,
*″ indicates a binding site to T2 in Formula 1,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to T3 in Formula 1.
In one or more embodiments, in Formula 1, each of n2 and n3 may be 1, and a group represented by
may be a group represented by one of Formulae CY3-1 to CY3-13 and ZCY3-1 to ZCY3-12-:
In Formulae CY3-1 to CY3-13 and ZCY3-1 to ZCY3-12,
X3 may be the same as described in the present specification,
X39 may be O, S, N-[(L3)b3-(R3)c3], C(R39a)(R39b), or Si(R39a)(R39b),
L3, b3, R3, and c3 may each be the same as described in the present specification,
R31 to R33, R39a, and R39b may each be the same as described in connection with R3 in the present specification, wherein each of R31 to R33 may not be hydrogen,
Z31 to Z33 may each be the same as described in connection with Z3 in the present specification,
*″ indicates a binding site to T2 in Formula 1,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to T3 in Formula 1.
In one or more embodiments, in Formula 1, n3 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY4(1) to CY4(20):
In Formulae CY4(1) to CY4(20),
X4 may be the same as described in the present specification,
X49 may be O, S, N(R49a), C(R49a)(R49b), or Si(R49a)(R49b),
R49a and R49b may each be the same as described in connection with R4 in the present specification,
*′ indicates a binding site to T3 in Formula 1, and
* indicates a binding site to M in Formula 1.
In one or more embodiments, in Formula 1, n3 may be 1, n4 may be 0, and a group represented by
may be a group represented by one of Formulae CY4-1 to CY4-16 and ZCY4-1 to ZCY4-32:
In Formulae CY4-1 to CY4-16 and ZC4-1 to ZCY4-32,
X4 may be the same as described in the present specification,
R41 to R44 may each be the same as described in connection with R4 in the present specification, wherein each of R41 to R44 may not be hydrogen,
Z41 to Z44 may each be the same as described in connection with Z4 in the present specification,
*′ indicates a binding site to T3 in Formula 1, and
* indicates a binding site to M in Formula 1.
In one or more embodiments, the organometallic compound may be represented by one of Formulae 1-1 to 1-4:
In Formulae 1-1 to 1-4,
M, X1 to X5, T2, and T3 may each be the same as described in the present specification,
X11 may be N, C(R11), or C(Z11), X12 may be N, C(R12), or C(Z12), X13 may be N, C(R13), or C(Z13), and X14 may be N, C(R14), or C(Z14),
R11 to R14 may each be the same as described in connection with R1 in the present specification,
Z11 to Z14 may each be the same as described in connection with Z1 in the present specification,
two or more of R11 to R14 may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
X21 may be N, C(R21), or C(Z21), X22 may be N, C(R22), or C(Z22), and X23 may be N, C(R23), or C(Z23),
X29 may be O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
L2, b2, R2, and c2 may each be the same as described in the present specification,
R21 to R23, R29a, and R29b may each be the same as described in connection with R2 in the present specification,
Z21 to Z24 may each be the same as described in connection with Z2 in the present specification,
two or more of R21 to R23 may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
X31 may be N, C(R31), or C(Z31), X32 may be N, C(R32), or C(Z32), and X33 may be N, C(R33), or C(Z33),
R31 to R33 may each be the same as described in connection with R3 in the present specification,
Z31 to Z33 may each be the same as described in connection with Z3 in the present specification,
two or more of R31 to R33 may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
X41 may be N, C(R41), or C(Z41),
X42 may be N, C(R42), or C(Z42),
X43 may be N, C(R43), or C(Z43),
X44 may be N, C(R44), or C(Z44),
R41 to R44 may each be the same as described in connection with R4 in the present specification,
Z41 to Z44 may each be the same as described in connection with Z4 in the present specification,
two or more of R41 to R44 may optionally be bonded together to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
Formulae 1-1 and 1-2 may each include one of Z11 to Z14, one of Z21 to Z23, one of Z31 to Z33, one of Z41 to Z44, or a combination thereof, and
R5a in Formula 1-4 may be a group represented by Formula 51.
In one or more embodiments,
i) the organometallic compound may be represented by Formula 1-1 or 1-2, and Formulae 1-1 and 1-2 may each satisfy at least one of Condition (1′) to Condition (3′);
ii) the organometallic compound may be represented by Formula 1-3 or 1-4; or
iii) the organometallic compound may be represented by Formula 1-3 or 1-4, and Formulae 1-3 and 1-4 may each satisfy at least one of Condition (1′) to Condition (3′):
Condition (1′)
Condition (2′)
Condition (3′)
In one or more embodiments, Z1 to Z4, Z11 to Z14, Z21 to Z24, Z31 to Z33, and Z41 to Z44 in the present specification may each independently be a group represented by one of Formulae 51-1 to 51-25.
In one or more embodiments, Z1 to Z4, Z11 to Z14, Z21 to Z24, Z31 to Z33, and Z41 to Z44 in the present specification may each independently be a group represented by one of Formulae 51(1) to 51(19).
In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition A to Condition E:
Condition A
n1 in Formula 1 is 1, n4 in Formula 1 is 0, and a group represented by
in Formula 1 is a group represented by one of Formulae ZCY1-1 to ZCY1-32
Condition B
each of n1 and n2 in Formula 1 is 1, and a group represented by
in Formula 1 is a group represented by one of Formulae ZCY2-1 to ZCY2-19.
Condition C
each of n2 and n3 in Formula 1 is 1, and a group represented by
in Formula 1 is a group represented by one of Formulae ZCY3-1 to ZCY3-12
Condition D
n3 in Formula 1 is 1, n4 in Formula 1 is 0, and a group represented by
in Formula 1 is a group represented by one of Formulae ZCY4-1 to ZCY4-32
Condition E
n3 in Formula 1 is 1, T3 in Formula 1 is *—N(R5a)—*′, and R5a in Formula 1 is a group represented by Formula 51.
In one or more embodiments, the organometallic compound represented by Formula 1 may emit green light.
In one or more embodiments, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 750:
The organometallic compound represented by Formula 1 satisfies at least one of Condition 1 and Condition 2 as described in the present specification. In other words, the organometallic compound represented by Formula 1 includes, as a substituent, at least one group represented by Formula 51. Accordingly, the organometallic compound represented by Formula 1 may have improved planarity and orientation characteristics, and thus, an electronic device, for example, an organic light-emitting device, using the organometallic compound represented by Formula 1 may have improved characteristics in terms of luminescence efficiency and/or lifespan.
A highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, and T1 energy level of the exemplary organometallic compound represented by Formula 1 were evaluated using the Gaussian 09 program with the molecular structure optimization obtained by B3LYP-based density functional theory (DFT), and results thereof are shown in Table 1. The energy levels in Table 1 are in electron volts (eV).
From Table 1, it is confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use as a dopant for an electric device, for example, an organic light-emitting device.
Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.
Accordingly, the organometallic compound represented by Formula 1 is suitable for use as a material for an organic layer of an organic light-emitting device, for example, a dopant in an emission layer of the organic layer. Thus, according to another aspect, provided is an organic light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, and the organic layer includes at least one organometallic compound represented by Formula 1.
Because the organic light-emitting device includes an organic layer including the organometallic compound represented by Formula 1, the organic light-emitting device may have higher external quantum efficiency and long lifespan.
The organometallic compound represented by Formula 1 may be utilized between a pair of electrodes of an organic light-emitting device. In one or more embodiments, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host). The emission layer may emit, for example, green light or blue light.
The expression “(an organic layer) includes at least one organometallic compounds represented by Formula 1” used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
In one or more embodiments, the organic layer may include, as the organometallic compound, a single Compound 1. In this embodiment, the single Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term “organic layer” used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, a structure of an organic light-emitting device according to one or more embodiments of the present disclosure and a method of manufacturing an organic light-emitting device according to one or more embodiments of the present disclosure will be described in connection with FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
A substrate may be additionally located under (e.g., below) the first electrode 11 or above (e.g., on top of) the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. In one or more embodiments, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.
The organic layer 15 is located on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, each layer is sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100 to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec.
When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 rpm to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C.
Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
The hole transport region may include 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-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or a combination thereof:
Ar101 and Ar102 in Formula 201 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. In one or more embodiments, xa may be 1, and xb may be 0.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, or the like), or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like);
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, C1-C10 alkyl group, a C1-C10 alkoxy group, or a combination thereof.
R109 in Formula 201 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with 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:
R101, R111, R112, and R109 in Formula 201A may each be the same as described above.
In one or more embodiments, the hole transport region may include one of Compounds HT1 to HT20 or a combination thereof:
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generating material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or a combination thereof. In one or more embodiments, the p-dopant may be: a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), or F6-TCNNQ; metal oxide, such as tungsten oxide and molybdenum oxide; a cyano group-containing compound, 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 according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
In one or more embodiments, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include a material that is used in the hole transport region as described above, a host material described below, or a combination thereof. In one or more embodiments, when the hole transport region includes an electron blocking layer, mCP described below, Compound H-H1 described below, or a combination thereof may be used as the material for forming the electron blocking layer.
An emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary depending on a compound that is used to form the emission layer.
The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 as described herein.
The host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-H2, or a combination thereof:
When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 20 parts by weight based on 100 parts by weight of the host.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Then, an electron transport region may be located on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
In one or more embodiments, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or a combination thereof.
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics 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 of Compounds ET1 to ET25 or a combination thereof:
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 or ET-D2:
Also, the electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, Compound ET-D1, Compound ET-D2, or a combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device has been described with reference to FIGURE, but embodiments of the present disclosure are not limited thereto.
According to another aspect, the organic light-emitting device may be included in an electronic apparatus. Thus, an electronic apparatus including the organic light-emitting device is provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, and the like.
According to another aspect, provided is a diagnostic composition including at least one organometallic compound represented by Formula 1.
The organometallic compound represented by Formula 1 may provide high luminescence efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbons monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group—as used 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 may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof. For example, Formula 9-33 is a branched C6 alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
The term “C1-C60 alkoxy group” used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.
The term “C1-C60 alklythio group” used herein refers to a monovalent group represented by —SA101 (wherein A101 is the C1-C60 alkyl group).
The term “C2-C60 alkenyl group” as used herein has a structure including at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein has a structure including at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and the C3-C10 cycloalkylene group is a divalent group having the same structure as the C3-C10 cycloalkyl group.
Examples of the C3-C10 cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monocyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom instead of a carbon atom, and 1 to 10 carbon atoms, and the term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
Examples of the C1-C10 heterocycloalkyl group are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom instead of a carbon atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
The term “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group. The term “C7-C60 aryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C6-C60 aryl group.
The term “C1-C6 heteroaryl group” as used herein refers to a monovalent group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom instead of a carbon atom, and a cyclic aromatic system having 1 to 60 carbon atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom instead of a carbon atom, and a cyclic aromatic system having 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group. The C2-C60 heteroaryl alkyl group used herein refers to a C1-C60 alkyl group substituted with at least one C1-C60 heteroaryl group.
The term “C6-C60 aryloxy group” as used herein indicates a group of formula —OA102 (wherein A102 indicates the C6-C60 aryl group), the C6-C60 arylthio group indicates a group of formula —SA103 (wherein A103 indicates the C6-C60 aryl group), and the C1-C60 alkylthio group indicates a group of formula —SA104 (wherein A104 indicates the C1-C60 alkyl group).
The term “C1-C60 heteroaryloxy group” as used herein indicates a group of formula —OA102a (wherein A102a indicates the C1-C60 heteroaryl group), and the C1-C60 heteroarylthio group indicates a group of formula —SA103a (wherein A103a indicates the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, or B, other than carbon atoms, as a ring-forming atom, and non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Examples of a substituted or unsubstituted C5-C30 carbocyclic group 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(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, or a fluorene group, each unsubstituted or substituted with at least one R10a.
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B instead of a carbon ring atom, other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. The “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a)” may include, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-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-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (, each unsubstituted or substituted with at least one R10a).
In one or more embodiments, examples of the terms “C5-C30 carbocyclic group” and “C1-C30 heterocyclic group” as used herein may include i) a first ring, ii) a second ring, iii) a condensed cyclic group in which two or more first rings are condensed with each other, iv) a condensed cyclic group in which two or more second rings are condensed with each other, or v) a condensed cyclic group in which one or more first rings and one or more second rings are condensed with each other,
the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, and
the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
The terms “fluorinated C1-C60 alkyl group (or a fluorinated C1-C20 alkyl group or the like)”, “fluorinated C3-C10 cycloalkyl group”, “fluorinated C1-C10 heterocycloalkyl group,” and “fluorinated phenyl group” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the “fluorinated C1 alkyl group (that is, the fluorinated methyl group)” may include —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group (or, a fluorinated C1-C20 alkyl group, or the like)”, “the fluorinated C3-C10 cycloalkyl group”, “the fluorinated C1-C10 heterocycloalkyl group”, or “the fluorinated a phenyl group” may be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen included therein is substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen included therein is not substituted with a fluoro group.
The terms “deuterated C1-C60 alkyl group (or a deuterated C1-C20 alkyl group or the like)”, “deuterated C3-C10 cycloalkyl group”, “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” as used herein respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group (that is, the deuterated methyl group)” may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” are, for example, Formula 10-501 and the like. The “deuterated C1-C60 alkyl group (or, the deuterated C1-C20 alkyl group or the like)”, “the deuterated C3-C10 cycloalkyl group”, “the deuterated C1-C10 heterocycloalkyl group”, or “the deuterated phenyl group” may be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen included therein are substituted with deuterium, or ii) a partially deuterated C1-C60 alkyl group (or, a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen included therein are not substituted with deuterium.
The term “(C1-C20 alkyl) ‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl) phenyl group is a toluyl group.
The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxide group” respectively refer to heterocyclic groups having the same backbones as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group,” as used herein each refer to the respective group wherein at least one ring-forming carbon atom is substituted with nitrogen.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted 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 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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, 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 C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —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.
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 described herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group which is 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 C1-C10 heterocycloalkenyl group; a C6-C60 aryl group which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 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; or a monovalent non-aromatic condensed heteropolycyclic group.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 described herein may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2, or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.
Compound 317-1 (7.9 grams (g), 11.0 millimoles (mmol)) and K2PtCl4 (5.5 g, 13.2 mmol) were mixed with 100 milliliters (mL) of acetic acid, the mixture was stirred while refluxing for 18 hours to proceed with the reaction, and then temperature was lowered to room temperature. A solid generated therefrom was filtered, and a column chromatography was performed using methylene chloride (MC) and hexane, to thereby obtain 4.2 g (yield: 42%) of Compound 317.
High resolution mass spectrometry-matrix assisted laser desorption ionization (HRMS (MALDI)) calcd for C50H49D2N3OPt: m/z 906.3805 Found: 906.3811.
Compound 351-1 (7.9 g, 11.1 mmol) and K2PtCl4 (5.5 g, 13.3 mmol) were mixed with 100 mL of acetic acid, the mixture was stirred while refluxing for 18 hours to proceed with the reaction, and then temperature was lowered to room temperature. A solid generated therefrom was filtered, and a column chromatography was performed using MC and hexane, to thereby obtain 3.8 g (yield: 38%) of Compound 351.
HRMS(MALDI) calcd for C51H37N3OPt: m/z 902.2584 Found: 902.2589.
Compound 592-1 (7.9 g, 11.1 mmol) and K2PtCl4 (5.5 g, 13.3 mmol) were mixed with 100 mL of acetic acid, the mixture was stirred while refluxing for 18 hours to proceed with the reaction, and then temperature was lowered to room temperature. A solid generated therefrom was filtered, and a column chromatography was performed using MC and hexane, to thereby obtain 3.1 g (yield: 31%) of Compound 592.
HRMS(MALDI) calcd for C50H46DN3OPt: m/z 901.3430 Found: 901.3420.
Compound 741-1 (3.9 g, 5.9 mmol) and K2PtCl4 (3.0 g, 7.1 mmol) were mixed with 50 mL of acetic acid, the mixture was stirred while refluxing for 18 hours to proceed with the reaction, and then temperature was lowered to room temperature. A solid generated therefrom was filtered, and a column chromatography was performed using MC and hexane, to thereby obtain 2.1 g (yield: 42%) of Compound 741.
HRMS(MALDI) calcd for C47H40N2OPt: m/z 843.2788 Found: 843.2795.
0.5 g (yield: 40%) of Compound A was obtained in the same manner as in Synthesis Example 1, except that Compound A-1 was used instead of Compound 317-1.
HRMS(MALDI) calcd for C43H45N3OPt: m/z 814.3210 Found: 814.3205.
0.4 g (yield: 36%) of Compound B was obtained in the same manner as in Synthesis Example 2, except that Compound B-1 was used instead of Compound 351-1.
HRMS(MALDI) calcd for C42H27N3OPt: m/z 784.1802 Found: 784.1796.
0.6 g (yield: 45%) of Compound C was obtained in the same manner as in Synthesis Example 3, except that Compound C-1 was used instead of Compound 592-1.
HRMS(MALDI) calcd for C42H39N3OPt: m/z 796.2741 Found: 796.2744.
0.2 g (yield: 22%) of Compound D was obtained in the same manner as in Synthesis Example 4, except that Compound D-1 was used instead of Compound 741-1.
HRMS(MALDI) calcd for C38H30N2OPt: m/z 725.2006 Found: 725.2001
An ITO (as an anode)-patterned glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and purified water (deionized water), each for 5 minutes, and then cleaned by irradiation of ultraviolet rays thereto and exposure to ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
HT3 and F6TCNNQ were vacuum-codeposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å. H-H1 was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 300 Å.
Next, H-H1, H-H2, and Compound 317 (dopant) were co-deposited on the electron blocking layer at a weight ratio of 42.5:42.5:15 to form an emission layer having a thickness of 400 Å.
Then, ET3 and ET-D1 were co-deposited 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, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 2 were each used instead of Compound 317 as a dopant in forming an emission layer.
With respect to each of the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples A to D, a maximum value of external quantum efficiency (EQEmax) (%) and lifespan (LT97)(relative value, %) were evaluated, and results thereof are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A) were used as apparatuses for evaluation, and the lifespan (LT97) (at 18,000 candela per square meter (cd/m2) or nit) was obtained by measuring the amount of time (hours) that elapsed until luminance was reduced to 97% of the initial luminance of 100%, and the results are expressed as a relative value (%).
Table 2
317
A
351
B
592
C
741
D
From Table 2, it is seen that each of the organic light-emitting devices of Examples 1 to 4 has higher external quantum efficiency and improved lifespan characteristics, compared to each of the organic light-emitting devices of Comparative Examples A to D.
The organometallic compound as described herein has excellent thermal stability and electrical characteristics. Accordingly, an electronic device, for example, an organic light-emitting device, using the organometallic compound may have improved external quantum efficiency and improved lifespan characteristics, and may emit light having a relatively small full width at half maximum (FWHM).
It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense 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
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2020-0141452 | Oct 2020 | KR | national |
