ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE

Information

  • Patent Application
  • 20240209012
  • Publication Number
    20240209012
  • Date Filed
    May 25, 2023
    a year ago
  • Date Published
    June 27, 2024
    6 months ago
Abstract
An organometallic compound, represented by Formula 1:
Description
CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0065551, filed on May 27, 2022, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated herein in its entirety by reference.


BACKGROUND
1. Field

The disclosure relates to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.


2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.


In an example, a typical organic light-emitting device includes an anode, a cathode, and an organic layer that is located between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons may recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.


SUMMARY

Aspects are directed to a an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.


Additional aspects will be set forth in part in the detailed description that follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments.


According to an aspect, an organometallic compound represented by Formula 1 is provided:





M(L1)n1(L2)n2  Formula 1


wherein, in Formula 1,

    • M is a transition metal,
    • L1 is a ligand represented by Formula 2-1,
    • L2 is a ligand represented by Formula 2-2,
    • n1 and n2 are each independently 1 or 2, when n1 is 2, two L1 are identical to or different from each other, and when n2 is 2, two L2 are identical to or different from each other,
    • L1 and L2 are different from each other,




embedded image


wherein, in Formulae 2-1 and 2-2,

    • X11 is Ge,
    • X2 is O, S, Se, N(R29), C(R29a)(R29b), or Si(R29a)(R29b),
    • A1 is C or N, A2 is C or N, A3 is C or N, and A4 is C or N, wherein one of A1 to A4 is C bonded to a neighboring pyridine group, and another of A1 to A4 is C bonded to M in Formula 1,
    • Y3 is N,
    • A31 is C or N, A32 is C or N, A33 is C or N, and A34 is C or N,
    • Y4 is C or N,
    • ring CY2 and ring CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein i) ring CY2 is a C3-C30 heterocyclic group including at least one N as a ring-forming atom, or ii) at least one of A1 to A4 is N, or iii) ring CY2 is a C3-C30 heterocyclic group including at least one N as a ring-forming atom, and at least one of A1 to A4 is N,
    • R1 to R4, R14 to R16, R29, R29a, and R29b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C1-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),
    • a1 is an integer from 0 to 3,
    • a2 is an integer from 0 to 6, and
    • a3 is an integer from 0 to 4,
    • a4 is an integer from 0 to 20,
    • two or more of a plurality of R1 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
    • two or more of a plurality of R2 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
    • two or more of a plurality of R3 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
    • two or more of a plurality of R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
    • two or more of R1 to R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
    • R10a is as described in connection with R2,
    • * and *′ each indicate a binding site to M in Formula 1,
    • at least one substituent of, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C1-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C1-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
    • deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a 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), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof,
    • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof,
    • N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39), or
    • a combination thereof,
    • wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.


According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organometallic compound represented by Formula 1.


The organometallic compound may be included in an emission layer, and the organometallic compound included in the emission layer may act as a dopant.


According to still another aspect, an electronic apparatus includes the organic light-emitting device described herein.





BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readily appreciated from the following detailed description of the exemplary embodiments, taken in conjunction with the FIGURE, which is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments.





DETAILED DESCRIPTION

Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing. In this regard, the exemplary embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the exemplary embodiments are merely described in further detail below by referring to the FIGURE, to explain aspects. The term “and/or” used herein includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.


The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.


It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.


Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.


It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.


Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.


“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within +30%, 20%, 10%, 5% of the stated value.


Hereinafter, a work function or a highest occupied molecular orbital (HOMO) energy level is expressed as an absolute value from a vacuum level. In addition, when the work function or the HOMO energy level is referred to be “deep,” “high” or “large,” the work function or the HOMO energy level has a large absolute value based on “0 electron Volt (eV)” of the vacuum level, while when the work function or the HOMO energy level is referred to be “shallow,” “low,” or “small,” the work function or HOMO energy level has a small absolute value based on “0 eV” of the vacuum level.


An organometallic compound is represented by Formula 1:





M(L1)n1(L2)n2  Formula 1


wherein M in Formula 1 is a transition metal.


For example, M may be a Period 1 transition metal of the Periodic Table of Elements, a Period 2 transition metal of the Periodic Table of Elements, or a Period 3 transition metal of the Periodic Table of Elements.


In one or more embodiments, M may be iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.


In one or more embodiments, M may be iridium, platinum, osmium, or rhodium.


In Formula 1, L1 is a ligand represented by Formula 2-1, and L2 is a ligand represented by Formula 2-2:




embedded image


wherein, Formulae 2-1 and 2-2 are as described herein.


n1 and n2 in Formula 1 respectively indicate the number of ligands L1 and the number of ligands L2, and n1 and n2 are each independently 1 or 2. When n1 is 2, two L1 are identical to or different from each other, and when n2 is 2, two L2 are identical to or different from each other.


For example, regarding Formula 1, i) n1 may be 2, and n2 may be 1; or ii) n1 may be 1, and n2 may be 2, but embodiments are not limited thereto.


In one or more embodiments, in Formula 1, i) M may be iridium or osmium, and a sum of n1 and n2 may be 3; or ii) M may be platinum, and a sum of n1 and n2 may be 2.


L1 and L2 in Formula 1 are different from each other. Accordingly, the organometallic compound represented by Formula 1 is a heteroleptic complex.


X11 in Formula 2-1 is Ge.


X2 in Formula 2-1 is O, S, Se, N(R29), C(R29a)(R29b), or Si(R29a)(R29b), wherein R29, R29a, and R29b are each as defined herein.


In one or more embodiments, X2 may be O or S.


In Formula 2-1, A1 is C or N, A2 is C or N, A3 is C or N, and A4 is C or N, wherein one of A1 to A4 is C bonded to a neighboring pyridine group, and another of A1 to A4 is C bonded to M in Formula 1.


In one or more embodiments, in Formula 2-1,

    • i) A1 may be C bonded to a neighboring pyridine group, A2 may be C bonded to M in Formula 1, and A3 and A4 may each independently be C or N,
    • ii) A2 may be C bonded to a neighboring pyridine group, A3 may be C bonded to M in Formula 1, and A1 and A4 may each independently be C or N,
    • iii) A3 may be C bonded to a neighboring pyridine group, A4 may be C bonded to M in Formula 1, and A1 and A2 may each independently be C or N,
    • iv) A2 may be C bonded to a neighboring pyridine group, A1 may be C bonded to M in Formula 1, and A3 and A4 may each independently be C or N,
    • v) A3 may be C bonded to a neighboring pyridine group, A2 may be C bonded to M in Formula 1, and A1 and A4 may each independently be C or N, or
    • vi) A4 may be C bonded to a neighboring pyridine group, A3 may be C bonded to M in Formula 1, and A1 and A2 may each independently be C or N.


In one or more embodiments, a group represented by




embedded image


of Formula 2-1 may be a group represented by one of Formulae CY2-A to CY2-F:




embedded image


wherein, in Formulae CY2-A to CY2-F,

    • X2 and ring CY2 are each as described herein,
    • A1 is C or N, A2 is C or N, A3 is C or N, and A4 is C or N,
    • *″ indicates a binding site to a neighboring pyridine group in Formula 2-1, and
    • * is a binding site to M in Formula 1.


Y3 in Formula 2-2 is N.


In Formula 2-2, A31 is C or N, A32 is C or N, A33 is C or N, and A34 is C or N.


In one or more embodiments, each of A31 to A34 may be C.


Y4 in Formula 2-2 is C or N.


In one or more embodiments, Y4 may be C.


In Formulae 2-1 and 2-2, ring CY2 and ring CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein i) ring CY2 is a C3-C30 heterocyclic group including at least one N as a ring-forming atom (for example, including, as a ring-forming moiety, one, two, or three *═N—*′, wherein * and *′ each indicate a binding site to an adjacent atom); ii) at least one of A1 to A4 is N; or iii) ring CY2 is a C3-C60 heterocyclic group including at least one N as a ring-forming atom (for example, including, as a ring-forming moiety, one, two, or three *═N—*′, wherein * and *′ each indicate a binding site to an adjacent atom), and at least one of A1 to A4 is N.


For example, ring CY2 and ring CY4 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring group in which at least two first rings are condensed to each other, iv) a condensed ring group in which at least two second rings are condensed to each other, or v) a condensed ring group in which at least one first ring and at least one second ring are condensed to each other,

    • the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, a germole group, a borole group, a selenophene group, a phosphole 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, an azasilole group, an azagermole group, an azaborole group, an azaselenophene group, or an azaphosphole group, and
    • the second ring may be an adamantane group, a norbornane group (a bicyclo[2.2.1]heptane group), a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.


In one or more embodiments, ring CY2 and ring CY4 may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a naphthobenzothiophene group, a naphthobenzofuran group, a naphthobenzoselenophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, a dinaphthothiophene group, a dinaphthofuran group, a dinaphthoselenophene group, a naphthocarbazole group, a naphthofluorene group, a phenanthrobenzosilole group, a phenanthrobenzothiophene group, a phenanthrobenzofuran group, a phenanthrobenzoselenophene group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azadibenzoselenophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzothiophene group, an azanaphthobenzofuran group, an azanaphthobenzoselenophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, an azadinaphthothiophene group, an azadinaphthofuran group, an azadinaphthoselenophene group, an azanaphthocarbazole group, an azanaphthofluorene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzoselenophene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with an adamantane group, a benzene group that is condensed with a norbornane group, a benzene group that is condensed with a norbornene group, a pyridine group that is condensed with an adamantane group, a pyridine group that is condensed with a norbornane group, or a pyridine group that is condensed with a norbornene group.


In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group.


In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group. In one or more embodiments, ring CY2 may be a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, or a dibenzoselenophene group, and at least one of A1 to A4 in Formula 2-1 may be N.


In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group, and at least one of A1 to A4 in Formula 2-1 may be N. In one or more embodiments, ring CY2 may be a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group, and all of A1 to A4 in Formula 2-1 may C.


In one or more embodiments, ring CY4 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group that is condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a naphthobenzothiophene group, a naphthobenzofuran group, a naphthobenzoselenophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, a dinaphthothiophene group, a dinaphthofuran group, a dinaphthoselenophene group, a naphthocarbazole group, a naphthofluorene group, a phenanthrobenzosilole group, a phenanthrobenzothiophene group, a phenanthrobenzofuran group, a phenanthrobenzoselenophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azadibenzoselenophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzothiophene group, an azanaphthobenzofuran group, an azanaphthobenzoselenophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, an azadinaphthothiophene group, an azadinaphthofuran group, an azadinaphthoselenophene group, an azanaphthocarbazole group, an azanaphthofluorene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzofuran group, or an azaphenanthrobenzoselenophene group.


R1 to R4, R14 to R16, R29, R29a, and R29b in Formulae 2-1 and 2-2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C0-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 are each as described herein. R2 represents a substituent group that may be bonded to any one or more of A1 to A4, and/or ring CY2.


In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not be —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 are each as described herein.


In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not include germanium (Ge).


In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not be —Si(Q3)(Q4)(Q5), wherein Q3 to Q5 are each as described herein.


In one or more embodiments, each of R1 to R4, R14 to R16, R29, R29a, and R29b may not include silicon (Si).


In one or more embodiments, in Formula 2-2, a3 may not be 0, at least one of R3 in the number of a3 may be —Si(Q3)(Q4)(Q5), and each of R1, R2, R4, R14 to R16, R29, R29a, and R29b may not include germanium (Ge) or silicon (Si), wherein Q3 to Q5 are each as described herein.


For example, R1 to R4, R14 to R16, R29, R29a, and R29b may each independently be:

    • hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group;
    • a C1-C20 alkyl group, a C1-C20 alkoxy group, or a C1-C20 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C1-C20 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)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 1,2,3,4-tetrahydronaphthyl 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 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio 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, 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 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, 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, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), 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 and Q33 to Q35 are each independently:
    • —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
    • an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C20 alkyl group, a phenyl group, or a combination thereof.


In one or more embodiments, R1 to R4, R29, R29a, and R29b may each independently be:

    • hydrogen, deuterium, —F, or a cyano group;
    • a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof; or
    • Si(Q3)(Q4)(Q5),
    • wherein Q3 to Q5 and Q33 to Q35 are each independently as described herein.


In one or more embodiments, R14 to R16 may each independently be a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.


In one or more embodiments, R14 to R16 in Formula 2-1 may each independently be —CH3, —CH2CH3, —CD3, —CD2H, —CDH2, —CH2CD3, —CD2CH3, or a phenyl group.


In one or more embodiments, R14 to R16 in Formula 2-1 may be identical to or different from each other.


In one or more embodiments, R1 to R4, R14 to R16, R29, R29a, and R29b in Formulae 2-1 and 2-2 may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —OCH3, —OCDH2, —OCD2H, —OCD3, —SCH3, —SCDH2, —SCD2H, —SCD3, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5), wherein Q3 to Q5 are each independently as described herein.


In one or more embodiments, at least one of R1 in the number of a1 in Formula 2-1 (for example, R11 of Formula CY1-1) may be a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium, or a group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


In Formulae 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is a trimethylgermyl group.


The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 or 9-601 to 9-637:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


wherein, in Formulae 9-501 to 9-514 and 9-601 to 9-637, * indicates a binding site to a neighboring atom.


The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 9-201 to 9-230 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 9-701 to 9-710:




embedded image


wherein, in Formulae 9-701 to 9-710, * indicates a binding site to a neighboring atom.


The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-553:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


wherein, in Formulae 10-501 to 10-553, * indicates a binding site to a neighboring atom.


The “group represented by one of Formulae 10-1 to 10-145 in which at least one hydrogen is substituted with —F” and the “group represented by one of Formulae 10-201 to 10-354 in which at least one hydrogen is substituted with —F” may be, for example, a group represented by one of Formulae 10-601 to 10-636:




embedded image


embedded image


embedded image


embedded image


wherein, in Formulae 10-601 to 10-636, * indicates a binding site to a neighboring atom.


a1 to a4 in Formula 2-1 and 2-2 indicate numbers of R1 to R4, respectively, and a1 is an integer from 0 to 3, a2 is an integer from 0 to 6, a3 is an integer from 0 to 4, and a4 is an integer from 1 to 20 (for example, an integer from 0 to 10). When a1 is 2 or greater, two or more of R1 may be identical to or different from each other, when a2 is 2 or greater, two or more of R2 may be identical to or different from each other, when a3 is 2 or greater, two or more of R3 may be identical to or different from each other, and when a4 is 2 or greater, two or more of R4 may be identical to or different from each other. For example, a1 to a4 may each independently be 0, 1, 2, or 3.


In one or more embodiments, in Formula 2-1, R2 may not be hydrogen.


In one or more embodiments, in Formula 2-2, R3 may not be hydrogen.


In one or more embodiments, the organometallic compound may include at least one of deuterium, a fluoro group, or a combination thereof.


In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of Condition 1 to Condition 8:


Condition 1





    • a1 in Formula 2-1 is not 0, and at least one of R1 in the number of a1 contains deuterium (for example, a1 in Formula 2-1 is not 0, and at least one of R1 in the number of a1 is deuterium or a deuterated C1-C20 alkyl group);





Condition 2





    • a2 in Formula 2-1 is not 0, and at least one of R2 in the number of a2 contains deuterium (for example, a2 in Formula 2-1 is not 0, and at least one of R2 in the number of a2 is deuterium or a deuterated C1-C20 alkyl group);





Condition 3





    • a3 in Formula 2-2 is not 0, and at least one of R3 in the number of a3 contains deuterium (for example, a3 in Formula 2-2 is not 0, and at least one of R3 in the number of a3 is deuterium or a deuterated C1-C20 alkyl group);





Condition 4





    • a4 in Formula 2-2 is not 0, and at least one of R4 in the number of a4 contains deuterium (for example, a4 in Formula 2-2 is not 0, and at least one of R4 in the number of a4 is deuterium or a deuterated C1-C20 alkyl group);





Condition 5





    • a1 in Formula 2-1 is not 0, and at least one of R1 in the number of a1 contains a fluoro group (for example, a1 in Formula 2-1 is not 0, and at least one of R1 in the number of a1 is a fluoro group or a fluorinated C1-C20 alkyl group);





Condition 6





    • a2 in Formula 2-1 is not 0, and at least one of R2 in the number of a2 contains a fluoro group (for example, a2 in Formula 2-1 is not 0, and at least one of R2 in the number of a2 is a fluoro group or a fluorinated C1-C20 alkyl group);





Condition 7





    • a3 in Formula 2-2 is not 0, and at least one of R3 in the number of a3 contains a fluoro group (for example, a3 in Formula 2-2 is not 0, and at least one of R3 in the number of a3 is a fluoro group or a fluorinated C1-C20 alkyl group);





Condition 8





    • a4 in Formula 2-2 is not 0, and at least one of R4 in the number of a4 contains a fluoro group (for example, a4 in Formula 2-2 is not 0, and at least one of R4 in the number of a4 is a fluoro group or a fluorinated C1-C20 alkyl group).





In Formulae 2-1 and 2-2, in each of i) two or more of a plurality of R1, ii) two or more of a plurality of R2, iii) two or more of a plurality of R3, iv) two or more of a plurality of R4, and v) two or more of R1 to R4, the two or more may be optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a. That is, i) two or more of a plurality of R1 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, ii) two or more of a plurality of R2 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iii) two or more of a plurality of R3 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, iv) two or more of a plurality of R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a, and v) two or more of R1 to R4 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a.


R10a is as described in connection with R2. For example, R10a may be as described in connection with R2, except that R10a may not be hydrogen.


* and *′ in Formulae 2-1 and 2-2 each indicate a binding site to M in Formula 1.


In one or more embodiments, a group represented by:




embedded image


in Formula 2-1 may be a group represented by one of Formulae CY1-1 to CY1-6:




embedded image


wherein, in Formulae CY1-1 to CY1-6,

    • X11, R14 to R16, and R10a are each as described herein,
    • R11 to R13 are each independently as described in connection with R1,
    • a14 may be an integer from 0 to 4,
    • a18 may be an integer from 0 to 8,
    • *′ indicates a binding site to M in Formula 1, and
    • *″ indicates a binding site to one of A1 to A4 in Formula 2-1.


For example, in one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen.


In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen or a methyl group.


In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen, a methyl group, or a cyano group.


In one or more embodiments, R11 in Formulae CY1-1 and/or CY1-4 may not be hydrogen, and R12 and R13 may each be hydrogen.


In one or more embodiments, R1 in Formulae CY1-1 and/or CY1-4 may include two or more carbon atoms, three or more carbon atoms, or four or more carbon atoms.


In one or more embodiments, R1 in Formulae CY1-1 and/or CY1-4 may be:

    • a methyl group that is substituted with at least one of deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof, or
    • a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof. Q33 to Q35 are each as defined herein.


In one or more embodiments, a group represented by




embedded image


in Formula 2-1 may be a group represented by one of Formulae CY2-1 to CY2-14:




embedded image


embedded image


embedded image


wherein, in Formulae CY2-1 to CY2-14,

    • X2 is as described herein,
    • A1 to A12 may each independently be C or N, and at least one of A1 to A8 of Formula CY2-1 may be N, at least one of A1 to A10 of Formulae CY2-2 to CY2-4 may be N, and at least one of A1 to A12 of Formulae CY2-5 to CY2-14 may be N,
    • *″ indicates a binding site to a neighboring pyridine group in Formula 2-1, and
    • * is a binding site to M in Formula 1.


For example, in one or more embodiments

    • at least one of A4 to A8 in Formula CY2-1 may be N,
    • at least one of A4 to A10 in Formulae CY2-2 to CY2-4 may be N, and
    • at least one of A4 to A12 in Formulae CY2-5 to CY2-14 may be N.


In one or more embodiments, a group represented by




embedded image


in Formula 2-1 may be a group represented by one of Formulae CY2(1) to CY2(60):




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


wherein, in Formulae CY2(1) to CY2(60),

    • X2 is as described herein,
    • R21 to R23 are each independently as described in connection with R2, wherein R21 to R23 are each not hydrogen,
    • *″ indicates a binding site to a neighboring pyridine group in Formula 2-1, and
    • * is a binding site to M in Formula 1.


In one or more embodiments, a group represented by




embedded image


in Formula 2-2 may be a group represented by one of Formulae CY3(1) to CY3(16):




embedded image


embedded image


embedded image


wherein, in Formulae CY3(1) to CY3(16),

    • Y3 is as described herein,
    • R31 to R34 are each independently as described in connection with R3, provided that each of R31 to R34 is not hydrogen,
    • *′ indicates a binding site to M in Formula 1, and
    • *″ indicates a binding site to a neighboring atom in Formula 2-2.


In one or more embodiments, a group represented by:




embedded image


in Formula 2-2 may be a group represented by one of Formulae CY4-1 to CY4-21:




embedded image


embedded image


embedded image


embedded image


wherein, in Formulae CY4-1 to CY4-21,

    • Y4 may be C,
    • A41 to A46 may each independently be C or N,
    • X4 may be O, S, Se, N(R49), C(R49a)(R49b), or Si(R49a)(R49b),
    • R49, R49a, and R49b are each independently as described in connection with R4,
    • * indicates a binding site to M in Formula 1, and
    • *″ indicates a binding site to a neighboring atom in Formula 2-2.


For example, A41 to A46 in Formulae CY4-16 to CY4-21 may each be C.


In one or more embodiments, A46 in Formulae CY4-16 to CY4-21 may be N.


In one or more embodiments, a group represented by:




embedded image


in Formula 2-2 may be a group represented by one of Formulae CY4-1 to CY4-16.


In one or more embodiments, a group represented by:




embedded image


in Formula 2-1 may be substituted with at least one R2, and a group represented by:




embedded image


may be unsubstituted or substituted with at least one R4, as defined herein.


In one or more embodiments, L1 in Formula 1 may be a ligand represented by one of Formulae B1 to B331:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


Each of * and in Formulae 131 to B331 indicates a binding site to M in Formula 1.


In one or more embodiments, L2 in Formula 1 may be a ligand represented by one of Formula A1 to A250:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


Each of * and *′ in Formulae A1 to A250 indicates a binding site to M in Formula 1.


In one or more embodiments, the organometallic compound is represented by Formula 1, wherein M in Formula 1 may be iridium, and L1, L2, n1, and n2 may each be as defined for the compounds shown in Tables 1 to 56:


















TABLE 1





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







2-1
B2
A1
1
2
2-208
B2
A208
1
2


2-2
B2
A2
1
2
2-209
B2
A209
1
2


2-3
B2
A3
1
2
2-212
B2
A212
1
2


2-5
B2
A5
1
2
2-213
B2
A213
1
2


2-8
B2
A8
1
2
2-214
B2
A214
1
2


2-35
B2
A35
1
2
2-215
B2
A215
1
2


2-36
B2
A36
1
2
2-216
B2
A216
1
2


2-45
B2
A45
1
2
2-217
B2
A217
1
2


2-47
B2
A47
1
2
2-221
B2
A221
1
2


2-49
B2
A49
1
2
2-222
B2
A222
1
2


2-60
B2
A60
1
2
2-224
B2
A224
1
2


2-86
B2
A86
1
2
2-225
B2
A225
1
2


2-94
B2
A94
1
2
2-226
B2
A226
1
2


2-99
B2
A99
1
2
2-228
B2
A228
1
2


2-101
B2
A101
1
2
2-229
B2
A229
1
2


2-139
B2
A139
1
2
2-231
B2
A231
1
2


2-161
B2
A161
1
2
2-232
B2
A232
1
2


2-162
B2
A162
1
2
2-233
B2
A233
1
2


2-181
B2
A181
1
2
2-235
B2
A235
1
2


2-182
B2
A182
1
2
2-236
B2
A236
1
2


2-191
B2
A191
1
2
2-237
B2
A237
1
2


2-192
B2
A192
1
2
2-238
B2
A238
1
2


2-193
B2
A193
1
2
2-239
B2
A239
1
2


2-194
B2
A194
1
2
2-241
B2
A241
1
2


2-196
B2
A196
1
2
2-242
B2
A242
1
2


2-197
B2
A197
1
2
2-243
B2
A243
1
2


2-199
B2
A199
1
2
2-246
B2
A246
1
2


2-200
B2
A200
1
2
2-247
B2
A247
1
2


2-201
B2
A201
1
2
2-248
B2
A248
1
2


2-203
B2
A203
1
2
2-249
B2
A249
1
2


2-206
B2
A206
1
2
2-250
B2
A250
1
2

























TABLE 2





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







3-1
B3
A1
1
2
3-208
B3
A208
1
2


3-2
B3
A2
1
2
3-209
B3
A209
1
2


3-3
B3
A3
1
2
3-212
B3
A212
1
2


3-5
B3
A5
1
2
3-213
B3
A213
1
2


3-8
B3
A8
1
2
3-214
B3
A214
1
2


3-35
B3
A35
1
2
3-215
B3
A215
1
2


3-36
B3
A36
1
2
3-216
B3
A216
1
2


3-45
B3
A45
1
2
3-217
B3
A217
1
2


3-47
B3
A47
1
2
3-221
B3
A221
1
2


3-49
B3
A49
1
2
3-222
B3
A222
1
2


3-60
B3
A60
1
2
3-224
B3
A224
1
2


3-86
B3
A86
1
2
3-225
B3
A225
1
2


3-94
B3
A94
1
2
3-226
B3
A226
1
2


3-99
B3
A99
1
2
3-228
B3
A228
1
2


3-101
B3
A101
1
2
3-229
B3
A229
1
2


3-139
B3
A139
1
2
3-231
B3
A231
1
2


3-161
B3
A161
1
2
3-232
B3
A232
1
2


3-162
B3
A162
1
2
3-233
B3
A233
1
2


3-181
B3
A181
1
2
3-235
B3
A235
1
2


3-182
B3
A182
1
2
3-236
B3
A236
1
2


3-191
B3
A191
1
2
3-237
B3
A237
1
2


3-192
B3
A192
1
2
3-238
B3
A238
1
2


3-193
B3
A193
1
2
3-239
B3
A239
1
2


3-194
B3
A194
1
2
3-241
B3
A241
1
2


3-196
B3
A196
1
2
3-242
B3
A242
1
2


3-197
B3
A197
1
2
3-243
B3
A243
1
2


3-199
B3
A199
1
2
3-246
B3
A246
1
2


3-200
B3
A200
1
2
3-247
B3
A247
1
2


3-201
B3
A201
1
2
3-248
B3
A248
1
2


3-203
B3
A203
1
2
3-249
B3
A249
1
2


3-206
B3
A206
1
2
3-250
B3
A250
1
2

























TABLE 3





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







4-1
B4
A1
1
2
4-208
B4
A208
1
2


4-2
B4
A2
1
2
4-209
B4
A209
1
2


4-3
B4
A3
1
2
4-212
B4
A212
1
2


4-5
B4
A5
1
2
4-213
B4
A213
1
2


4-8
B4
A8
1
2
4-214
B4
A214
1
2


4-35
B4
A35
1
2
4-215
B4
A215
1
2


4-36
B4
A36
1
2
4-216
B4
A216
1
2


4-45
B4
A45
1
2
4-217
B4
A217
1
2


4-47
B4
A47
1
2
4-221
B4
A221
1
2


4-49
B4
A49
1
2
4-222
B4
A222
1
2


4-60
B4
A60
1
2
4-224
B4
A224
1
2


4-86
B4
A86
1
2
4-225
B4
A225
1
2


4-94
B4
A94
1
2
4-226
B4
A226
1
2


4-99
B4
A99
1
2
4-228
B4
A228
1
2


4-101
B4
A101
1
2
4-229
B4
A229
1
2


4-139
B4
A139
1
2
4-231
B4
A231
1
2


4-161
B4
A161
1
2
4-232
B4
A232
1
2


4-162
B4
A162
1
2
4-233
B4
A233
1
2


4-181
B4
A181
1
2
4-235
B4
A235
1
2


4-182
B4
A182
1
2
4-236
B4
A236
1
2


4-191
B4
A191
1
2
4-237
B4
A237
1
2


4-192
B4
A192
1
2
4-238
B4
A238
1
2


4-193
B4
A193
1
2
4-239
B4
A239
1
2


4-194
B4
A194
1
2
4-241
B4
A241
1
2


4-196
B4
A196
1
2
4-242
B4
A242
1
2


4-197
B4
A197
1
2
4-243
B4
A243
1
2


4-199
B4
A199
1
2
4-246
B4
A246
1
2


4-200
B4
A200
1
2
4-247
B4
A247
1
2


4-201
B4
A201
1
2
4-248
B4
A248
1
2


4-203
B4
A203
1
2
4-249
B4
A249
1
2


4-206
B4
A206
1
2
4-250
B4
A250
1
2

























TABLE 4





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







6-1
B6
A1
1
2
6-208
B6
A208
1
2


6-2
B6
A2
1
2
6-209
B6
A209
1
2


6-3
B6
A3
1
2
6-212
B6
A212
1
2


6-5
B6
A5
1
2
6-213
B6
A213
1
2


6-8
B6
A8
1
2
6-214
B6
A214
1
2


6-35
B6
A35
1
2
6-215
B6
A215
1
2


6-36
B6
A36
1
2
6-216
B6
A216
1
2


6-45
B6
A45
1
2
6-217
B6
A217
1
2


6-47
B6
A47
1
2
6-221
B6
A221
1
2


6-49
B6
A49
1
2
6-222
B6
A222
1
2


6-60
B6
A60
1
2
6-224
B6
A224
1
2


6-86
B6
A86
1
2
6-225
B6
A225
1
2


6-94
B6
A94
1
2
6-226
B6
A226
1
2


6-99
B6
A99
1
2
6-228
B6
A228
1
2


6-101
B6
A101
1
2
6-229
B6
A229
1
2


6-139
B6
A139
1
2
6-231
B6
A231
1
2


6-161
B6
A161
1
2
6-232
B6
A232
1
2


6-162
B6
A162
1
2
6-233
B6
A233
1
2


6-181
B6
A181
1
2
6-235
B6
A235
1
2


6-182
B6
A182
1
2
6-236
B6
A236
1
2


6-191
B6
A191
1
2
6-237
B6
A237
1
2


6-192
B6
A192
1
2
6-238
B6
A238
1
2


6-193
B6
A193
1
2
6-239
B6
A239
1
2


6-194
B6
A194
1
2
6-241
B6
A241
1
2


6-196
B6
A196
1
2
6-242
B6
A242
1
2


6-197
B6
A197
1
2
6-243
B6
A243
1
2


6-199
B6
A199
1
2
6-246
B6
A246
1
2


6-200
B6
A200
1
2
6-247
B6
A247
1
2


6-201
B6
A201
1
2
6-248
B6
A248
1
2


6-203
B6
A203
1
2
6-249
B6
A249
1
2


6-206
B6
A206
1
2
6-250
B6
A250
1
2

























TABLE 5





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







10-1
B10
A1
1
2
10-208
B10
A208
1
2


10-2
B10
A2
1
2
10-209
B10
A209
1
2


10-3
B10
A3
1
2
10-212
B10
A212
1
2


10-5
B10
A5
1
2
10-213
B10
A213
1
2


10-8
B10
A8
1
2
10-214
B10
A214
1
2


10-35
B10
A35
1
2
10-215
B10
A215
1
2


10-36
B10
A36
1
2
10-216
B10
A216
1
2


10-45
B10
A45
1
2
10-217
B10
A217
1
2


10-47
B10
A47
1
2
10-221
B10
A221
1
2


10-49
B10
A49
1
2
10-222
B10
A222
1
2


10-60
B10
A60
1
2
10-224
B10
A224
1
2


10-86
B10
A86
1
2
10-225
B10
A225
1
2


10-94
B10
A94
1
2
10-226
B10
A226
1
2


10-99
B10
A99
1
2
10-228
B10
A228
1
2


10-101
B10
A101
1
2
10-229
B10
A229
1
2


10-139
B10
A139
1
2
10-231
B10
A231
1
2


10-161
B10
A161
1
2
10-232
B10
A232
1
2


10-162
B10
A162
1
2
10-233
B10
A233
1
2


10-181
B10
A181
1
2
10-235
B10
A235
1
2


10-182
B10
A182
1
2
10-236
B10
A236
1
2


10-191
B10
A191
1
2
10-237
B10
A237
1
2


10-192
B10
A192
1
2
10-238
B10
A238
1
2


10-193
B10
A193
1
2
10-239
B10
A239
1
2


10-194
B10
A194
1
2
10-241
B10
A241
1
2


10-196
B10
A196
1
2
10-242
B10
A242
1
2


10-197
B10
A197
1
2
10-243
B10
A243
1
2


10-199
B10
A199
1
2
10-246
B10
A246
1
2


10-200
B10
A200
1
2
10-247
B10
A247
1
2


10-201
B10
A201
1
2
10-248
B10
A248
1
2


10-203
B10
A203
1
2
10-249
B10
A249
1
2


10-206
B10
A206
1
2
10-250
B10
A250
1
2

























TABLE 6





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







12-1
B12
A1
1
2
12-208
B12
A208
1
2


12-2
B12
A2
1
2
12-209
B12
A209
1
2


12-3
B12
A3
1
2
12-212
B12
A212
1
2


12-5
B12
A5
1
2
12-213
B12
A213
1
2


12-8
B12
A8
1
2
12-214
B12
A214
1
2


12-35
B12
A35
1
2
12-215
B12
A215
1
2


12-36
B12
A36
1
2
12-216
B12
A216
1
2


12-45
B12
A45
1
2
12-217
B12
A217
1
2


12-47
B12
A47
1
2
12-221
B12
A221
1
2


12-49
B12
A49
1
2
12-222
B12
A222
1
2


12-60
B12
A60
1
2
12-224
B12
A224
1
2


12-86
B12
A86
1
2
12-225
B12
A225
1
2


12-94
B12
A94
1
2
12-226
B12
A226
1
2


12-99
B12
A99
1
2
12-228
B12
A228
1
2


12-101
B12
A101
1
2
12-229
B12
A229
1
2


12-139
B12
A139
1
2
12-231
B12
A231
1
2


12-161
B12
A161
1
2
12-232
B12
A232
1
2


12-162
B12
A162
1
2
12-233
B12
A233
1
2


12-181
B12
A181
1
2
12-235
B12
A235
1
2


12-182
B12
A182
1
2
12-236
B12
A236
1
2


12-191
B12
A191
1
2
12-237
B12
A237
1
2


12-192
B12
A192
1
2
12-238
B12
A238
1
2


12-193
B12
A193
1
2
12-239
B12
A239
1
2


12-194
B12
A194
1
2
12-241
B12
A241
1
2


12-196
B12
A196
1
2
12-242
B12
A242
1
2


12-197
B12
A197
1
2
12-243
B12
A243
1
2


12-199
B12
A199
1
2
12-246
B12
A246
1
2


12-200
B12
A200
1
2
12-247
B12
A247
1
2


12-201
B12
A201
1
2
12-248
B12
A248
1
2


12-203
B12
A203
1
2
12-249
B12
A249
1
2


12-206
B12
A206
1
2
12-250
B12
A250
1
2

























TABLE 7





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







15-1
B15
A1
1
2
15-208
B15
A208
1
2


15-2
B15
A2
1
2
15-209
B15
A209
1
2


15-3
B15
A3
1
2
15-212
B15
A212
1
2


15-5
B15
A5
1
2
15-213
B15
A213
1
2


15-8
B15
A8
1
2
15-214
B15
A214
1
2


15-35
B15
A35
1
2
15-215
B15
A215
1
2


15-36
B15
A36
1
2
15-216
B15
A216
1
2


15-45
B15
A45
1
2
15-217
B15
A217
1
2


15-47
B15
A47
1
2
15-221
B15
A221
1
2


15-49
B15
A49
1
2
15-222
B15
A222
1
2


15-60
B15
A60
1
2
15-224
B15
A224
1
2


15-86
B15
A86
1
2
15-225
B15
A225
1
2


15-94
B15
A94
1
2
15-226
B15
A226
1
2


15-99
B15
A99
1
2
15-228
B15
A228
1
2


15-101
B15
A101
1
2
15-229
B15
A229
1
2


15-139
B15
A139
1
2
15-231
B15
A231
1
2


15-161
B15
A161
1
2
15-232
B15
A232
1
2


15-162
B15
A162
1
2
15-233
B15
A233
1
2


15-181
B15
A181
1
2
15-235
B15
A235
1
2


15-182
B15
A182
1
2
15-236
B15
A236
1
2


15-191
B15
A191
1
2
15-237
B15
A237
1
2


15-192
B15
A192
1
2
15-238
B15
A238
1
2


15-193
B15
A193
1
2
15-239
B15
A239
1
2


15-194
B15
A194
1
2
15-241
B15
A241
1
2


15-196
B15
A196
1
2
15-242
B15
A242
1
2


15-197
B15
A197
1
2
15-243
B15
A243
1
2


15-199
B15
A199
1
2
15-246
B15
A246
1
2


15-200
B15
A200
1
2
15-247
B15
A247
1
2


15-201
B15
A201
1
2
15-248
B15
A248
1
2


15-203
B15
A203
1
2
15-249
B15
A249
1
2


15-206
B15
A206
1
2
15-250
B15
A250
1
2

























TABLE 8





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







22-1
B22
A1
1
2
22-208
B22
A208
1
2


22-2
B22
A2
1
2
22-209
B22
A209
1
2


22-3
B22
A3
1
2
22-212
B22
A212
1
2


22-5
B22
A5
1
2
22-213
B22
A213
1
2


22-8
B22
A8
1
2
22-214
B22
A214
1
2


22-35
B22
A35
1
2
22-215
B22
A215
1
2


22-36
B22
A36
1
2
22-216
B22
A216
1
2


22-45
B22
A45
1
2
22-217
B22
A217
1
2


22-47
B22
A47
1
2
22-221
B22
A221
1
2


22-49
B22
A49
1
2
22-222
B22
A222
1
2


22-60
B22
A60
1
2
22-224
B22
A224
1
2


22-86
B22
A86
1
2
22-225
B22
A225
1
2


22-94
B22
A94
1
2
22-226
B22
A226
1
2


22-99
B22
A99
1
2
22-228
B22
A228
1
2


22-101
B22
A101
1
2
22-229
B22
A229
1
2


22-139
B22
A139
1
2
22-231
B22
A231
1
2


22-161
B22
A161
1
2
22-232
B22
A232
1
2


22-162
B22
A162
1
2
22-233
B22
A233
1
2


22-181
B22
A181
1
2
22-235
B22
A235
1
2


22-182
B22
A182
1
2
22-236
B22
A236
1
2


22-191
B22
A191
1
2
22-237
B22
A237
1
2


22-192
B22
A192
1
2
22-238
B22
A238
1
2


22-193
B22
A193
1
2
22-239
B22
A239
1
2


22-194
B22
A194
1
2
22-241
B22
A241
1
2


22-196
B22
A196
1
2
22-242
B22
A242
1
2


22-197
B22
A197
1
2
22-243
B22
A243
1
2


22-199
B22
A199
1
2
22-246
B22
A246
1
2


22-200
B22
A200
1
2
22-247
B22
A247
1
2


22-201
B22
A201
1
2
22-248
B22
A248
1
2


22-203
B22
A203
1
2
22-249
B22
A249
1
2


22-206
B22
A206
1
2
22-250
B22
A250
1
2

























TABLE 9





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







24-1
B24
A1
1
2
24-208
B24
A208
1
2


24-2
B24
A2
1
2
24-209
B24
A209
1
2


24-3
B24
A3
1
2
24-212
B24
A212
1
2


24-5
B24
A5
1
2
24-213
B24
A213
1
2


24-8
B24
A8
1
2
24-214
B24
A214
1
2


24-35
B24
A35
1
2
24-215
B24
A215
1
2


24-36
B24
A36
1
2
24-216
B24
A216
1
2


24-45
B24
A45
1
2
24-217
B24
A217
1
2


24-47
B24
A47
1
2
24-221
B24
A221
1
2


24-49
B24
A49
1
2
24-222
B24
A222
1
2


24-60
B24
A60
1
2
24-224
B24
A224
1
2


24-86
B24
A86
1
2
24-225
B24
A225
1
2


24-94
B24
A94
1
2
24-226
B24
A226
1
2


24-99
B24
A99
1
2
24-228
B24
A228
1
2


24-101
B24
A101
1
2
24-229
B24
A229
1
2


24-139
B24
A139
1
2
24-231
B24
A231
1
2


24-161
B24
A161
1
2
24-232
B24
A232
1
2


24-162
B24
A162
1
2
24-233
B24
A233
1
2


24-181
B24
A181
1
2
24-235
B24
A235
1
2


24-182
B24
A182
1
2
24-236
B24
A236
1
2


24-191
B24
A191
1
2
24-237
B24
A237
1
2


24-192
B24
A192
1
2
24-238
B24
A238
1
2


24-193
B24
A193
1
2
24-239
B24
A239
1
2


24-194
B24
A194
1
2
24-241
B24
A241
1
2


24-196
B24
A196
1
2
24-242
B24
A242
1
2


24-197
B24
A197
1
2
24-243
B24
A243
1
2


24-199
B24
A199
1
2
24-246
B24
A246
1
2


24-200
B24
A200
1
2
24-247
B24
A247
1
2


24-201
B24
A201
1
2
24-248
B24
A248
1
2


24-203
B24
A203
1
2
24-249
B24
A249
1
2


24-206
B24
A206
1
2
24-250
B24
A250
1
2






















TABLE 10







Compound







No.
L1
L2
n1
n2






















26-1
B26
A1
1
2



26-2
B26
A2
1
2



26-3
B26
A3
1
2



26-5
B26
A5
1
2



26-8
B26
A8
1
2



26-35
B26
A35
1
2



26-36
B26
A36
1
2



26-45
B26
A45
1
2



26-47
B26
A47
1
2



26-49
B26
A49
1
2



26-60
B26
A60
1
2



26-86
B26
A86
1
2



26-94
B26
A94
1
2



26-99
B26
A99
1
2



26-101
B26
A101
1
2



26-139
B26
A139
1
2



26-161
B26
A161
1
2



26-162
B26
A162
1
2



26-181
B26
A181
1
2



26-182
B26
A182
1
2



26-191
B26
A191
1
2



26-192
B26
A192
1
2



26-193
B26
A193
1
2



26-194
B26
A194
1
2



26-196
B26
A196
1
2



26-197
B26
A197
1
2



26-199
B26
A199
1
2



26-200
B26
A200
1
2



26-201
B26
A201
1
2



26-203
B26
A203
1
2



26-206
B26
A206
1
2



26-208
B26
A208
1
2



26-209
B26
A209
1
2



26-212
B26
A212
1
2



26-213
B26
A213
1
2



26-214
B26
A214
1
2



26-215
B26
A215
1
2



26-216
B26
A216
1
2



26-217
B26
A217
1
2



26-221
B26
A221
1
2



26-222
B26
A222
1
2



26-224
B26
A224
1
2



26-225
B26
A225
1
2



26-226
B26
A226
1
2



26-228
B26
A228
1
2



26-229
B26
A229
1
2



26-231
B26
A231
1
2



26-232
B26
A232
1
2



26-233
B26
A233
1
2



26-235
B26
A235
1
2



26-236
B26
A236
1
2



26-237
B26
A237
1
2



26-238
B26
A238
1
2



26-239
B26
A239
1
2



26-241
B26
A241
1
2



26-242
B26
A242
1
2



26-243
B26
A243
1
2



26-246
B26
A246
1
2



26-247
B26
A247
1
2



26-248
B26
A248
1
2



26-249
B26
A249
1
2



26-250
B26
A250
1
2























TABLE 11







Compound







No.
L1
L2
n1
n2






















29-1
B29
A1
1
2



29-2
B29
A2
1
2



29-3
B29
A3
1
2



29-5
B29
A5
1
2



29-8
B29
A8
1
2



29-35
B29
A35
1
2



29-36
B29
A36
1
2



29-45
B29
A45
1
2



29-47
B29
A47
1
2



29-49
B29
A49
1
2



29-60
B29
A60
1
2



29-86
B29
A86
1
2



29-94
B29
A94
1
2



29-99
B29
A99
1
2



29-101
B29
A101
1
2



29-139
B29
A139
1
2



29-161
B29
A161
1
2



29-162
B29
A162
1
2



29-181
B29
A181
1
2



29-182
B29
A182
1
2



29-191
B29
A191
1
2



29-192
B29
A192
1
2



29-193
B29
A193
1
2



29-194
B29
A194
1
2



29-196
B29
A196
1
2



29-197
B29
A197
1
2



29-199
B29
A199
1
2



29-200
B29
A200
1
2



29-201
B29
A201
1
2



29-203
B29
A203
1
2



29-206
B29
A206
1
2



29-208
B29
A208
1
2



29-209
B29
A209
1
2



29-212
B29
A212
1
2



29-213
B29
A213
1
2



29-214
B29
A214
1
2



29-215
B29
A215
1
2



29-216
B29
A216
1
2



29-217
B29
A217
1
2



29-221
B29
A221
1
2



29-222
B29
A222
1
2



29-224
B29
A224
1
2



29-225
B29
A225
1
2



29-226
B29
A226
1
2



29-228
B29
A228
1
2



29-229
B29
A229
1
2



29-231
B29
A231
1
2



29-232
B29
A232
1
2



29-233
B29
A233
1
2



29-235
B29
A235
1
2



29-236
B29
A236
1
2



29-237
B29
A237
1
2



29-238
B29
A238
1
2



29-239
B29
A239
1
2



29-241
B29
A241
1
2



29-242
B29
A242
1
2



29-243
B29
A243
1
2



29-246
B29
A246
1
2



29-247
B29
A247
1
2



29-248
B29
A248
1
2



29-249
B29
A249
1
2



29-250
B29
A250
1
2























TABLE 12







Compound







No.
L1
L2
n1
n2






















32-1
B32
A1
1
2



32-2
B32
A2
1
2



32-3
B32
A3
1
2



32-5
B32
A5
1
2



32-8
B32
A8
1
2



32-35
B32
A35
1
2



32-36
B32
A36
1
2



32-45
B32
A45
1
2



32-47
B32
A47
1
2



32-49
B32
A49
1
2



32-60
B32
A60
1
2



32-86
B32
A86
1
2



32-94
B32
A94
1
2



32-99
B32
A99
1
2



32-101
B32
A101
1
2



32-139
B32
A139
1
2



32-161
B32
A161
1
2



32-162
B32
A162
1
2



32-181
B32
A181
1
2



32-182
B32
A182
1
2



32-191
B32
A191
1
2



32-192
B32
A192
1
2



32-193
B32
A193
1
2



32-194
B32
A194
1
2



32-196
B32
A196
1
2



32-197
B32
A197
1
2



32-199
B32
A199
1
2



32-200
B32
A200
1
2



32-201
B32
A201
1
2



32-203
B32
A203
1
2



32-206
B32
A206
1
2



32-208
B32
A208
1
2



32-209
B32
A209
1
2



32-212
B32
A212
1
2



32-213
B32
A213
1
2



32-214
B32
A214
1
2



32-215
B32
A215
1
2



32-216
B32
A216
1
2



32-217
B32
A217
1
2



32-221
B32
A221
1
2



32-222
B32
A222
1
2



32-224
B32
A224
1
2



32-225
B32
A225
1
2



32-226
B32
A226
1
2



32-228
B32
A228
1
2



32-229
B32
A229
1
2



32-231
B32
A231
1
2



32-232
B32
A232
1
2



32-233
B32
A233
1
2



32-235
B32
A235
1
2



32-236
B32
A236
1
2



32-237
B32
A237
1
2



32-238
B32
A238
1
2



32-239
B32
A239
1
2



32-241
B32
A241
1
2



32-242
B32
A242
1
2



32-243
B32
A243
1
2



32-246
B32
A246
1
2



32-247
B32
A247
1
2



32-248
B32
A248
1
2



32-249
B32
A249
1
2



32-250
B32
A250
1
2























TABLE 13







Compound







No.
L1
L2
n1
n2






















33-1
B33
A1
1
2



33-2
B33
A2
1
2



33-3
B33
A3
1
2



33-5
B33
A5
1
2



33-8
B33
A8
1
2



33-35
B33
A35
1
2



33-36
B33
A36
1
2



33-45
B33
A45
1
2



33-47
B33
A47
1
2



33-49
B33
A49
1
2



33-60
B33
A60
1
2



33-86
B33
A86
1
2



33-94
B33
A94
1
2



33-99
B33
A99
1
2



33-101
B33
A101
1
2



33-139
B33
A139
1
2



33-161
B33
A161
1
2



33-162
B33
A162
1
2



33-181
B33
A181
1
2



33-182
B33
A182
1
2



33-191
B33
A191
1
2



33-192
B33
A192
1
2



33-193
B33
A193
1
2



33-194
B33
A194
1
2



33-196
B33
A196
1
2



33-197
B33
A197
1
2



33-199
B33
A199
1
2



33-200
B33
A200
1
2



33-201
B33
A201
1
2



33-203
B33
A203
1
2



33-206
B33
A206
1
2



33-208
B33
A208
1
2



33-209
B33
A209
1
2



33-212
B33
A212
1
2



33-213
B33
A213
1
2



33-214
B33
A214
1
2



33-215
B33
A215
1
2



33-216
B33
A216
1
2



33-217
B33
A217
1
2



33-221
B33
A221
1
2



33-222
B33
A222
1
2



33-224
B33
A224
1
2



33-225
B33
A225
1
2



33-226
B33
A226
1
2



33-228
B33
A228
1
2



33-229
B33
A229
1
2



33-231
B33
A231
1
2



33-232
B33
A232
1
2



33-233
B33
A233
1
2



33-235
B33
A235
1
2



33-236
B33
A236
1
2



33-237
B33
A237
1
2



33-238
B33
A238
1
2



33-239
B33
A239
1
2



33-241
B33
A241
1
2



33-242
B33
A242
1
2



33-243
B33
A243
1
2



33-246
B33
A246
1
2



33-247
B33
A247
1
2



33-248
B33
A248
1
2



33-249
B33
A249
1
2



33-250
B33
A250
1
2























TABLE 14







Compound







No.
L1
L2
n1
n2






















53-1
B53
A1
1
2



53-2
B53
A2
1
2



53-3
B53
A3
1
2



53-5
B53
A5
1
2



53-8
B53
A8
1
2



53-35
B53
A35
1
2



53-36
B53
A36
1
2



53-45
B53
A45
1
2



53-47
B53
A47
1
2



53-49
B53
A49
1
2



53-60
B53
A60
1
2



53-86
B53
A86
1
2



53-94
B53
A94
1
2



53-99
B53
A99
1
2



53-101
B53
A101
1
2



53-139
B53
A139
1
2



53-161
B53
A161
1
2



53-162
B53
A162
1
2



53-181
B53
A181
1
2



53-182
B53
A182
1
2



53-191
B53
A191
1
2



53-192
B53
A192
1
2



53-193
B53
A193
1
2



53-194
B53
A194
1
2



53-196
B53
A196
1
2



53-197
B53
A197
1
2



53-199
B53
A199
1
2



53-200
B53
A200
1
2



53-201
B53
A201
1
2



53-203
B53
A203
1
2



53-206
B53
A206
1
2



53-208
B53
A208
1
2



53-209
B53
A209
1
2



53-212
B53
A212
1
2



53-213
B53
A213
1
2



53-214
B53
A214
1
2



53-215
B53
A215
1
2



53-216
B53
A216
1
2



53-217
B53
A217
1
2



53-221
B53
A221
1
2



53-222
B53
A222
1
2



53-224
B53
A224
1
2



53-225
B53
A225
1
2



53-226
B53
A226
1
2



53-228
B53
A228
1
2



53-229
B53
A229
1
2



53-231
B53
A231
1
2



53-232
B53
A232
1
2



53-233
B53
A233
1
2



53-235
B53
A235
1
2



53-236
B53
A236
1
2



53-237
B53
A237
1
2



53-238
B53
A238
1
2



53-239
B53
A239
1
2



53-241
B53
A241
1
2



53-242
B53
A242
1
2



53-243
B53
A243
1
2



53-246
B53
A246
1
2



53-247
B53
A247
1
2



53-248
B53
A248
1
2



53-249
B53
A249
1
2



53-250
B53
A250
1
2























TABLE 15







Compound







No.
L1
L2
n1
n2






















54-1
B54
A1
1
2



54-2
B54
A2
1
2



54-3
B54
A3
1
2



54-5
B54
A5
1
2



54-8
B54
A8
1
2



54-35
B54
A35
1
2



54-36
B54
A36
1
2



54-45
B54
A45
1
2



54-47
B54
A47
1
2



54-49
B54
A49
1
2



54-60
B54
A60
1
2



54-86
B54
A86
1
2



54-94
B54
A94
1
2



54-99
B54
A99
1
2



54-101
B54
A101
1
2



54-139
B54
A139
1
2



54-161
B54
A161
1
2



54-162
B54
A162
1
2



54-181
B54
A181
1
2



54-182
B54
A182
1
2



54-191
B54
A191
1
2



54-192
B54
A192
1
2



54-193
B54
A193
1
2



54-194
B54
A194
1
2



54-196
B54
A196
1
2



54-197
B54
A197
1
2



54-199
B54
A199
1
2



54-200
B54
A200
1
2



54-201
B54
A201
1
2



54-203
B54
A203
1
2



54-206
B54
A206
1
2



54-208
B54
A208
1
2



54-209
B54
A209
1
2



54-212
B54
A212
1
2



54-213
B54
A213
1
2



54-214
B54
A214
1
2



54-215
B54
A215
1
2



54-216
B54
A216
1
2



54-217
B54
A217
1
2



54-221
B54
A221
1
2



54-222
B54
A222
1
2



54-224
B54
A224
1
2



54-225
B54
A225
1
2



54-226
B54
A226
1
2



54-228
B54
A228
1
2



54-229
B54
A229
1
2



54-231
B54
A231
1
2



54-232
B54
A232
1
2



54-233
B54
A233
1
2



54-235
B54
A235
1
2



54-236
B54
A236
1
2



54-237
B54
A237
1
2



54-238
B54
A238
1
2



54-239
B54
A239
1
2



54-241
B54
A241
1
2



54-242
B54
A242
1
2



54-243
B54
A243
1
2



54-246
B54
A246
1
2



54-247
B54
A247
1
2



54-248
B54
A248
1
2



54-249
B54
A249
1
2



54-250
B54
A250
1
2























TABLE 16







Compound







No.
L1
L2
n1
n2






















62-1
B62
A1
1
2



62-2
B62
A2
1
2



62-3
B62
A3
1
2



62-5
B62
A5
1
2



62-8
B62
A8
1
2



62-35
B62
A35
1
2



62-36
B62
A36
1
2



62-45
B62
A45
1
2



62-47
B62
A47
1
2



62-49
B62
A49
1
2



62-60
B62
A60
1
2



62-86
B62
A86
1
2



62-94
B62
A94
1
2



62-99
B62
A99
1
2



62-101
B62
A101
1
2



62-139
B62
A139
1
2



62-161
B62
A161
1
2



62-162
B62
A162
1
2



62-181
B62
A181
1
2



62-182
B62
A182
1
2



62-191
B62
A191
1
2



62-192
B62
A192
1
2



62-193
B62
A193
1
2



62-194
B62
A194
1
2



62-196
B62
A196
1
2



62-197
B62
A197
1
2



62-199
B62
A199
1
2



62-200
B62
A200
1
2



62-201
B62
A201
1
2



62-203
B62
A203
1
2



62-206
B62
A206
1
2



62-208
B62
A208
1
2



62-209
B62
A209
1
2



62-212
B62
A212
1
2



62-213
B62
A213
1
2



62-214
B62
A214
1
2



62-215
B62
A215
1
2



62-216
B62
A216
1
2



62-217
B62
A217
1
2



62-221
B62
A221
1
2



62-222
B62
A222
1
2



62-224
B62
A224
1
2



62-225
B62
A225
1
2



62-226
B62
A226
1
2



62-228
B62
A228
1
2



62-229
B62
A229
1
2



62-231
B62
A231
1
2



62-232
B62
A232
1
2



62-233
B62
A233
1
2



62-235
B62
A235
1
2



62-236
B62
A236
1
2



62-237
B62
A237
1
2



62-238
B62
A238
1
2



62-239
B62
A239
1
2



62-241
B62
A241
1
2



62-242
B62
A242
1
2



62-243
B62
A243
1
2



62-246
B62
A246
1
2



62-247
B62
A247
1
2



62-248
B62
A248
1
2



62-249
B62
A249
1
2



62-250
B62
A250
1
2























TABLE 17







Compound







No.
L1
L2
n1
n2






















66-1
B66
A1
1
2



66-2
B66
A2
1
2



66-3
B66
A3
1
2



66-5
B66
A5
1
2



66-8
B66
A8
1
2



66-35
B66
A35
1
2



66-36
B66
A36
1
2



66-45
B66
A45
1
2



66-47
B66
A47
1
2



66-49
B66
A49
1
2



66-60
B66
A60
1
2



66-86
B66
A86
1
2



66-94
B66
A94
1
2



66-99
B66
A99
1
2



66-101
B66
A101
1
2



66-139
B66
A139
1
2



66-161
B66
A161
1
2



66-162
B66
A162
1
2



66-181
B66
A181
1
2



66-182
B66
A182
1
2



66-191
B66
A191
1
2



66-192
B66
A192
1
2



66-193
B66
A193
1
2



66-194
B66
A194
1
2



66-196
B66
A196
1
2



66-197
B66
A197
1
2



66-199
B66
A199
1
2



66-200
B66
A200
1
2



66-201
B66
A201
1
2



66-203
B66
A203
1
2



66-206
B66
A206
1
2



66-208
B66
A208
1
2



66-209
B66
A209
1
2



66-212
B66
A212
1
2



66-213
B66
A213
1
2



66-214
B66
A214
1
2



66-215
B66
A215
1
2



66-216
B66
A216
1
2



66-217
B66
A217
1
2



66-221
B66
A221
1
2



66-222
B66
A222
1
2



66-224
B66
A224
1
2



66-225
B66
A225
1
2



66-226
B66
A226
1
2



66-228
B66
A228
1
2



66-229
B66
A229
1
2



66-231
B66
A231
1
2



66-232
B66
A232
1
2



66-233
B66
A233
1
2



66-235
B66
A235
1
2



66-236
B66
A236
1
2



66-237
B66
A237
1
2



66-238
B66
A238
1
2



66-239
B66
A239
1
2



66-241
B66
A241
1
2



66-242
B66
A242
1
2



66-243
B66
A243
1
2



66-246
B66
A246
1
2



66-247
B66
A247
1
2



66-248
B66
A248
1
2



66-249
B66
A249
1
2



66-250
B66
A250
1
2























TABLE 18







Compound







No.
L1
L2
n1
n2






















67-1
B67
A1
1
2



67-2
B67
A2
1
2



67-3
B67
A3
1
2



67-5
B67
A5
1
2



67-8
B67
A8
1
2



67-35
B67
A35
1
2



67-36
B67
A36
1
2



67-45
B67
A45
1
2



67-47
B67
A47
1
2



67-49
B67
A49
1
2



67-60
B67
A60
1
2



67-86
B67
A86
1
2



67-94
B67
A94
1
2



67-99
B67
A99
1
2



67-101
B67
A101
1
2



67-139
B67
A139
1
2



67-161
B67
A161
1
2



67-162
B67
A162
1
2



67-181
B67
A181
1
2



67-182
B67
A182
1
2



67-191
B67
A191
1
2



67-192
B67
A192
1
2



67-193
B67
A193
1
2



67-194
B67
A194
1
2



67-196
B67
A196
1
2



67-197
B67
A197
1
2



67-199
B67
A199
1
2



67-200
B67
A200
1
2



67-201
B67
A201
1
2



67-203
B67
A203
1
2



67-206
B67
A206
1
2



67-208
B67
A208
1
2



67-209
B67
A209
1
2



67-212
B67
A212
1
2



67-213
B67
A213
1
2



67-214
B67
A214
1
2



67-215
B67
A215
1
2



67-216
B67
A216
1
2



67-217
B67
A217
1
2



67-221
B67
A221
1
2



67-222
B67
A222
1
2



67-224
B67
A224
1
2



67-225
B67
A225
1
2



67-226
B67
A226
1
2



67-228
B67
A228
1
2



67-229
B67
A229
1
2



67-231
B67
A231
1
2



67-232
B67
A232
1
2



67-233
B67
A233
1
2



67-235
B67
A235
1
2



67-236
B67
A236
1
2



67-237
B67
A237
1
2



67-238
B67
A238
1
2



67-239
B67
A239
1
2



67-241
B67
A241
1
2



67-242
B67
A242
1
2



67-243
B67
A243
1
2



67-246
B67
A246
1
2



67-247
B67
A247
1
2



67-248
B67
A248
1
2



67-249
B67
A249
1
2



67-250
B67
A250
1
2























TABLE 19







Compound







No.
L1
L2
n1
n2






















70-1
B70
A1
1
2



70-2
B70
A2
1
2



70-3
B70
A3
1
2



70-5
B70
A5
1
2



70-8
B70
A8
1
2



70-35
B70
A35
1
2



70-36
B70
A36
1
2



70-45
B70
A45
1
2



70-47
B70
A47
1
2



70-49
B70
A49
1
2



70-60
B70
A60
1
2



70-86
B70
A86
1
2



70-94
B70
A94
1
2



70-99
B70
A99
1
2



70-101
B70
A101
1
2



70-139
B70
A139
1
2



70-161
B70
A161
1
2



70-162
B70
A162
1
2



70-181
B70
A181
1
2



70-182
B70
A182
1
2



70-191
B70
A191
1
2



70-192
B70
A192
1
2



70-193
B70
A193
1
2



70-194
B70
A194
1
2



70-196
B70
A196
1
2



70-197
B70
A197
1
2



70-199
B70
A199
1
2



70-200
B70
A200
1
2



70-201
B70
A201
1
2



70-203
B70
A203
1
2



70-206
B70
A206
1
2



70-208
B70
A208
1
2



70-209
B70
A209
1
2



70-212
B70
A212
1
2



70-213
B70
A213
1
2



70-214
B70
A214
1
2



70-215
B70
A215
1
2



70-216
B70
A216
1
2



70-217
B70
A217
1
2



70-221
B70
A221
1
2



70-222
B70
A222
1
2



70-224
B70
A224
1
2



70-225
B70
A225
1
2



70-226
B70
A226
1
2



70-228
B70
A228
1
2



70-229
B70
A229
1
2



70-231
B70
A231
1
2



70-232
B70
A232
1
2



70-233
B70
A233
1
2



70-235
B70
A235
1
2



70-236
B70
A236
1
2



70-237
B70
A237
1
2



70-238
B70
A238
1
2



70-239
B70
A239
1
2



70-241
B70
A241
1
2



70-242
B70
A242
1
2



70-243
B70
A243
1
2



70-246
B70
A246
1
2



70-247
B70
A247
1
2



70-248
B70
A248
1
2



70-249
B70
A249
1
2



70-250
B70
A250
1
2























TABLE 20







Compound







No.
L1
L2
n1
n2






















75-1
B75
A1
1
2



75-2
B75
A2
1
2



75-3
B75
A3
1
2



75-5
B75
A5
1
2



75-8
B75
A8
1
2



75-35
B75
A35
1
2



75-36
B75
A36
1
2



75-45
B75
A45
1
2



75-47
B75
A47
1
2



75-49
B75
A49
1
2



75-60
B75
A60
1
2



75-86
B75
A86
1
2



75-94
B75
A94
1
2



75-99
B75
A99
1
2



75-101
B75
A101
1
2



75-139
B75
A139
1
2



75-161
B75
A161
1
2



75-162
B75
A162
1
2



75-181
B75
A181
1
2



75-182
B75
A182
1
2



75-191
B75
A191
1
2



75-192
B75
A192
1
2



75-193
B75
A193
1
2



75-194
B75
A194
1
2



75-196
B75
A196
1
2



75-197
B75
A197
1
2



75-199
B75
A199
1
2



75-200
B75
A200
1
2



75-201
B75
A201
1
2



75-203
B75
A203
1
2



75-206
B75
A206
1
2



75-208
B75
A208
1
2



75-209
B75
A209
1
2



75-212
B75
A212
1
2



75-213
B75
A213
1
2



75-214
B75
A214
1
2



75-215
B75
A215
1
2



75-216
B75
A216
1
2



75-217
B75
A217
1
2



75-221
B75
A221
1
2



75-222
B75
A222
1
2



75-224
B75
A224
1
2



75-225
B75
A225
1
2



75-226
B75
A226
1
2



75-228
B75
A228
1
2



75-229
B75
A229
1
2



75-231
B75
A231
1
2



75-232
B75
A232
1
2



75-233
B75
A233
1
2



75-235
B75
A235
1
2



75-236
B75
A236
1
2



75-237
B75
A237
1
2



75-238
B75
A238
1
2



75-239
B75
A239
1
2



75-241
B75
A241
1
2



75-242
B75
A242
1
2



75-243
B75
A243
1
2



75-246
B75
A246
1
2



75-247
B75
A247
1
2



75-248
B75
A248
1
2



75-249
B75
A249
1
2



75-250
B75
A250
1
2























TABLE 21







Compound







No.
L1
L2
n1
n2






















82-1
B82
A1
1
2



82-2
B82
A2
1
2



82-3
B82
A3
1
2



82-5
B82
A5
1
2



82-8
B82
A8
1
2



82-35
B82
A35
1
2



82-36
B82
A36
1
2



82-45
B82
A45
1
2



82-47
B82
A47
1
2



82-49
B82
A49
1
2



82-60
B82
A60
1
2



82-86
B82
A86
1
2



82-94
B82
A94
1
2



82-99
B82
A99
1
2



82-101
B82
A101
1
2



82-139
B82
A139
1
2



82-161
B82
A161
1
2



82-162
B82
A162
1
2



82-181
B82
A181
1
2



82-182
B82
A182
1
2



82-191
B82
A191
1
2



82-192
B82
A192
1
2



82-193
B82
A193
1
2



82-194
B82
A194
1
2



82-196
B82
A196
1
2



82-197
B82
A197
1
2



82-199
B82
A199
1
2



82-200
B82
A200
1
2



82-201
B82
A201
1
2



82-203
B82
A203
1
2



82-206
B82
A206
1
2



82-208
B82
A208
1
2



82-209
B82
A209
1
2



82-212
B82
A212
1
2



82-213
B82
A213
1
2



82-214
B82
A214
1
2



82-215
B82
A215
1
2



82-216
B82
A216
1
2



82-217
B82
A217
1
2



82-221
B82
A221
1
2



82-222
B82
A222
1
2



82-224
B82
A224
1
2



82-225
B82
A225
1
2



82-226
B82
A226
1
2



82-228
B82
A228
1
2



82-229
B82
A229
1
2



82-231
B82
A231
1
2



82-232
B82
A232
1
2



82-233
B82
A233
1
2



82-235
B82
A235
1
2



82-236
B82
A236
1
2



82-237
B82
A237
1
2



82-238
B82
A238
1
2



82-239
B82
A239
1
2



82-241
B82
A241
1
2



82-242
B82
A242
1
2



82-243
B82
A243
1
2



82-246
B82
A246
1
2



82-247
B82
A247
1
2



82-248
B82
A248
1
2



82-249
B82
A249
1
2



82-250
B82
A250
1
2























TABLE 22







Compound







No.
L1
L2
n1
n2






















89-1
B89
A1
1
2



89-2
B89
A2
1
2



89-3
B89
A3
1
2



89-5
B89
A5
1
2



89-8
B89
A8
1
2



89-35
B89
A35
1
2



89-36
B89
A36
1
2



89-45
B89
A45
1
2



89-47
B89
A47
1
2



89-49
B89
A49
1
2



89-60
B89
A60
1
2



89-86
B89
A86
1
2



89-94
B89
A94
1
2



89-99
B89
A99
1
2



89-101
B89
A101
1
2



89-139
B89
A139
1
2



89-161
B89
A161
1
2



89-162
B89
A162
1
2



89-181
B89
A181
1
2



89-182
B89
A182
1
2



89-191
B89
A191
1
2



89-192
B89
A192
1
2



89-193
B89
A193
1
2



89-194
B89
A194
1
2



89-196
B89
A196
1
2



89-197
B89
A197
1
2



89-199
B89
A199
1
2



89-200
B89
A200
1
2



89-201
B89
A201
1
2



89-203
B89
A203
1
2



89-206
B89
A206
1
2



89-208
B89
A208
1
2



89-209
B89
A209
1
2



89-212
B89
A212
1
2



89-213
B89
A213
1
2



89-214
B89
A214
1
2



89-215
B89
A215
1
2



89-216
B89
A216
1
2



89-217
B89
A217
1
2



89-221
B89
A221
1
2



89-222
B89
A222
1
2



89-224
B89
A224
1
2



89-225
B89
A225
1
2



89-226
B89
A226
1
2



89-228
B89
A228
1
2



89-229
B89
A229
1
2



89-231
B89
A231
1
2



89-232
B89
A232
1
2



89-233
B89
A233
1
2



89-235
B89
A235
1
2



89-236
B89
A236
1
2



89-237
B89
A237
1
2



89-238
B89
A238
1
2



89-239
B89
A239
1
2



89-241
B89
A241
1
2



89-242
B89
A242
1
2



89-243
B89
A243
1
2



89-246
B89
A246
1
2



89-247
B89
A247
1
2



89-248
B89
A248
1
2



89-249
B89
A249
1
2



89-250
B89
A250
1
2























TABLE 23







Compound







No.
L1
L2
n1
n2









91-1
B91
A1
1
2



91-2
B91
A2
1
2



91-3
B91
A3
1
2



91-5
B91
A5
1
2



91-8
B91
A8
1
2



91-35
B91
A35
1
2



91-36
B91
A36
1
2



91-45
B91
A45
1
2



91-47
B91
A47
1
2



91-49
B91
A49
1
2



91-60
B91
A60
1
2



91-86
B91
A86
1
2



91-94
B91
A94
1
2



91-99
B91
A99
1
2



91-101
B91
A101
1
2



91-139
B91
A139
1
2



91-161
B91
A161
1
2



91-162
B91
A162
1
2



91-181
B91
A181
1
2



91-182
B91
A182
1
2



91-191
B91
A191
1
2



91-192
B91
A192
1
2



91-193
B91
A193
1
2



91-194
B91
A194
1
2



91-196
B91
A196
1
2



91-197
B91
A197
1
2



91-199
B91
A199
1
2



91-200
B91
A200
1
2



91-201
B91
A201
1
2



91-203
B91
A203
1
2



91-206
B91
A206
1
2



91-208
B91
A208
1
2



91-209
B91
A209
1
2



91-212
B91
A212
1
2



91-213
B91
A213
1
2



91-214
B91
A214
1
2



91-215
B91
A215
1
2



91-216
B91
A216
1
2



91-217
B91
A217
1
2



91-221
B91
A221
1
2



91-222
B91
A222
1
2



91-224
B91
A224
1
2



91-225
B91
A225
1
2



91-226
B91
A226
1
2



91-228
B91
A228
1
2



91-229
B91
A229
1
2



91-231
B91
A231
1
2



91-232
B91
A232
1
2



91-233
B91
A233
1
2



91-235
B91
A235
1
2



91-236
B91
A236
1
2



91-237
B91
A237
1
2



91-238
B91
A238
1
2



91-239
B91
A239
1
2



91-241
B91
A241
1
2



91-242
B91
A242
1
2



91-243
B91
A243
1
2



91-246
B91
A246
1
2



91-247
B91
A247
1
2



91-248
B91
A248
1
2



91-249
B91
A249
1
2



91-250
B91
A250
1
2























TABLE 24







Compound







No.
L1
L2
n1
n2









99-1
B99
A1
1
2



99-2
B99
A2
1
2



99-3
B99
A3
1
2



99-5
B99
A5
1
2



99-8
B99
A8
1
2



99-35
B99
A35
1
2



99-36
B99
A36
1
2



99-45
B99
A45
1
2



99-47
B99
A47
1
2



99-49
B99
A49
1
2



99-60
B99
A60
1
2



99-86
B99
A86
1
2



99-94
B99
A94
1
2



99-99
B99
A99
1
2



99-101
B99
A101
1
2



99-139
B99
A139
1
2



99-161
B99
A161
1
2



99-162
B99
A162
1
2



99-181
B99
A181
1
2



99-182
B99
A182
1
2



99-191
B99
A191
1
2



99-192
B99
A192
1
2



99-193
B99
A193
1
2



99-194
B99
A194
1
2



99-196
B99
A196
1
2



99-197
B99
A197
1
2



99-199
B99
A199
1
2



99-200
B99
A200
1
2



99-201
B99
A201
1
2



99-203
B99
A203
1
2



99-206
B99
A206
1
2



99-208
B99
A208
1
2



99-209
B99
A209
1
2



99-212
B99
A212
1
2



99-213
B99
A213
1
2



99-214
B99
A214
1
2



99-215
B99
A215
1
2



99-216
B99
A216
1
2



99-217
B99
A217
1
2



99-221
B99
A221
1
2



99-222
B99
A222
1
2



99-224
B99
A224
1
2



99-225
B99
A225
1
2



99-226
B99
A226
1
2



99-228
B99
A228
1
2



99-229
B99
A229
1
2



99-231
B99
A231
1
2



99-232
B99
A232
1
2



99-233
B99
A233
1
2



99-235
B99
A235
1
2



99-236
B99
A236
1
2



99-237
B99
A237
1
2



99-238
B99
A238
1
2



99-239
B99
A239
1
2



99-241
B99
A241
1
2



99-242
B99
A242
1
2



99-243
B99
A243
1
2



99-246
B99
A246
1
2



99-247
B99
A247
1
2



99-248
B99
A248
1
2



99-249
B99
A249
1
2



99-250
B99
A250
1
2























TABLE 25







Compound







No.
L1
L2
n1
n2









106-1
B106
A1
1
2



106-2
B106
A2
1
2



106-3
B106
A3
1
2



106-5
B106
A5
1
2



106-8
B106
A8
1
2



106-35
B106
A35
1
2



106-36
B106
A36
1
2



106-45
B106
A45
1
2



106-47
B106
A47
1
2



106-49
B106
A49
1
2



106-60
B106
A60
1
2



106-86
B106
A86
1
2



106-94
B106
A94
1
2



106-99
B106
A99
1
2



106-101
B106
A101
1
2



106-139
B106
A139
1
2



106-161
B106
A161
1
2



106-162
B106
A162
1
2



106-181
B106
A181
1
2



106-182
B106
A182
1
2



106-191
B106
A191
1
2



106-192
B106
A192
1
2



106-193
B106
A193
1
2



106-194
B106
A194
1
2



106-196
B106
A196
1
2



106-197
B106
A197
1
2



106-199
B106
A199
1
2



106-200
B106
A200
1
2



106-201
B106
A201
1
2



106-203
B106
A203
1
2



106-206
B106
A206
1
2



106-208
B106
A208
1
2



106-209
B106
A209
1
2



106-212
B106
A212
1
2



106-213
B106
A213
1
2



106-214
B106
A214
1
2



106-215
B106
A215
1
2



106-216
B106
A216
1
2



106-217
B106
A217
1
2



106-221
B106
A221
1
2



106-222
B106
A222
1
2



106-224
B106
A224
1
2



106-225
B106
A225
1
2



106-226
B106
A226
1
2



106-228
B106
A228
1
2



106-229
B106
A229
1
2



106-231
B106
A231
1
2



106-232
B106
A232
1
2



106-233
B106
A233
1
2



106-235
B106
A235
1
2



106-236
B106
A236
1
2



106-237
B106
A237
1
2



106-238
B106
A238
1
2



106-239
B106
A239
1
2



106-241
B106
A241
1
2



106-242
B106
A242
1
2



106-243
B106
A243
1
2



106-246
B106
A246
1
2



106-247
B106
A247
1
2



106-248
B106
A248
1
2



106-249
B106
A249
1
2



106-250
B106
A250
1
2























TABLE 26







Compound







No.
L1
L2
n1
n2









111-1
B111
A1
1
2



111-2
B111
A2
1
2



111-3
B111
A3
1
2



111-5
B111
A5
1
2



111-8
B111
A8
1
2



111-35
B111
A35
1
2



111-36
B111
A36
1
2



111-45
B111
A45
1
2



111-47
B111
A47
1
2



111-49
B111
A49
1
2



111-60
B111
A60
1
2



111-86
B111
A86
1
2



111-94
B111
A94
1
2



111-99
B111
A99
1
2



111-101
B111
A101
1
2



111-139
B111
A139
1
2



111-161
B111
A161
1
2



111-162
B111
A162
1
2



111-181
B111
A181
1
2



111-182
B111
A182
1
2



111-191
B111
A191
1
2



111-192
B111
A192
1
2



111-193
B111
A193
1
2



111-194
B111
A194
1
2



111-196
B111
A196
1
2



111-197
B111
A197
1
2



111-199
B111
A199
1
2



111-200
B111
A200
1
2



111-201
B111
A201
1
2



111-203
B111
A203
1
2



111-206
B111
A206
1
2



111-208
B111
A208
1
2



111-209
B111
A209
1
2



111-212
B111
A212
1
2



111-213
B111
A213
1
2



111-214
B111
A214
1
2



111-215
B111
A215
1
2



111-216
B111
A216
1
2



111-217
B111
A217
1
2



111-221
B111
A221
1
2



111-222
B111
A222
1
2



111-224
B111
A224
1
2



111-225
B111
A225
1
2



111-226
B111
A226
1
2



111-228
B111
A228
1
2



111-229
B111
A229
1
2



111-231
B111
A231
1
2



111-232
B111
A232
1
2



111-233
B111
A233
1
2



111-235
B111
A235
1
2



111-236
B111
A236
1
2



111-237
B111
A237
1
2



111-238
B111
A238
1
2



111-239
B111
A239
1
2



111-241
B111
A241
1
2



111-242
B111
A242
1
2



111-243
B111
A243
1
2



111-246
B111
A246
1
2



111-247
B111
A247
1
2



111-248
B111
A248
1
2



111-249
B111
A249
1
2



111-250
B111
A250
1
2


























TABLE 27





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







115-1
B115
A1
1
2
115-208
B115
A208
1
2


115-2
B115
A2
1
2
115-209
B115
A209
1
2


115-3
B115
A3
1
2
115-212
B115
A212
1
2


115-5
B115
A5
1
2
115-213
B115
A213
1
2


111-8
B115
A8
1
2
115-214
B115
A214
1
2


115-35
B115
A35
1
2
115-215
B115
A215
1
2


115-36
B115
A36
1
2
115-216
B115
A216
1
2


115-45
B115
A45
1
2
115-217
B115
A217
1
2


115-47
B115
A47
1
2
115-221
B115
A221
1
2


115-49
B115
A49
1
2
115-222
B115
A222
1
2


115-60
B115
A60
1
2
115-224
B115
A224
1
2


115-86
B115
A86
1
2
115-225
B115
A225
1
2


115-94
B115
A94
1
2
115-226
B115
A226
1
2


115-99
B115
A99
1
2
115-228
B115
A228
1
2


115-101
B115
A101
1
2
115-229
B115
A229
1
2


115-139
B115
A139
1
2
115-231
B115
A231
1
2


115-161
B115
A161
1
2
115-232
B115
A232
1
2


115-162
B115
A162
1
2
115-233
B115
A233
1
2


115-181
B115
A181
1
2
115-235
B115
A235
1
2


115-182
B115
A182
1
2
115-236
B115
A236
1
2


115-191
B115
A191
1
2
115-237
B115
A237
1
2


115-192
B115
A192
1
2
115-238
B115
A238
1
2


115-193
B115
A193
1
2
115-239
B115
A239
1
2


115-194
B115
A194
1
2
115-241
B115
A241
1
2


115-196
B115
A196
1
2
115-242
B115
A242
1
2


115-197
B115
A197
1
2
115-243
B115
A243
1
2


115-199
B115
A199
1
2
115-246
B115
A246
1
2


115-200
B115
A200
1
2
115-247
B115
A247
1
2


115-201
B115
A201
1
2
115-248
B115
A248
1
2


115-203
B115
A203
1
2
115-249
B115
A249
1
2


115-206
B115
A206
1
2
115-250
B115
A250
1
2

























TABLE 28





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







122-1
B122
A1
1
2
122-208
B122
A208
1
2


122-2
B122
A2
1
2
122-209
B122
A209
1
2


122-3
B122
A3
1
2
122-212
B122
A212
1
2


122-5
B122
A5
1
2
122-213
B122
A213
1
2


122-8
B122
A8
1
2
122-214
B122
A214
1
2


122-35
B122
A35
1
2
122-215
B122
A215
1
2


122-36
B122
A36
1
2
122-216
B122
A216
1
2


122-45
B122
A45
1
2
122-217
B122
A217
1
2


122-47
B122
A47
1
2
122-221
B122
A221
1
2


122-49
B122
A49
1
2
122-222
B122
A222
1
2


122-60
B122
A60
1
2
122-224
B122
A224
1
2


122-86
B122
A86
1
2
122-225
B122
A225
1
2


122-94
B122
A94
1
2
122-226
B122
A226
1
2


122-99
B122
A99
1
2
122-228
B122
A228
1
2


122-101
B122
A101
1
2
122-229
B122
A229
1
2


122-139
B122
A139
1
2
122-231
B122
A231
1
2


122-161
B122
A161
1
2
122-232
B122
A232
1
2


122-162
B122
A162
1
2
122-233
B122
A233
1
2


122-181
B122
A181
1
2
122-235
B122
A235
1
2


122-182
B122
A182
1
2
122-236
B122
A236
1
2


122-191
B122
A191
1
2
122-237
B122
A237
1
2


122-192
B122
A192
1
2
122-238
B122
A238
1
2


122-193
B122
A193
1
2
122-239
B122
A239
1
2


122-194
B122
A194
1
2
122-241
B122
A241
1
2


122-196
B122
A196
1
2
122-242
B122
A242
1
2


122-197
B122
A197
1
2
122-243
B122
A243
1
2


122-199
B122
A199
1
2
122-246
B122
A246
1
2


122-200
B122
A200
1
2
122-247
B122
A247
1
2


122-201
B122
A201
1
2
122-248
B122
A248
1
2


122-203
B122
A203
1
2
122-249
B122
A249
1
2


122-206
B122
A206
1
2
122-250
B122
A250
1
2

























TABLE 29





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







146-1
B146
A1
1
2
146-208
B146
A208
1
2


146-2
B146
A2
1
2
146-209
B146
A209
1
2


146-3
B146
A3
1
2
146-212
B146
A212
1
2


146-5
B146
A5
1
2
146-213
B146
A213
1
2


146-8
B146
A8
1
2
146-214
B146
A214
1
2


146-35
B146
A35
1
2
146-215
B146
A215
1
2


146-36
B146
A36
1
2
146-216
B146
A216
1
2


146-45
B146
A45
1
2
146-217
B146
A217
1
2


146-47
B146
A47
1
2
146-221
B146
A221
1
2


146-49
B146
A49
1
2
146-222
B146
A222
1
2


146-60
B146
A60
1
2
146-224
B146
A224
1
2


146-86
B146
A86
1
2
146-225
B146
A225
1
2


146-94
B146
A94
1
2
146-226
B146
A226
1
2


146-99
B146
A99
1
2
146-228
B146
A228
1
2


146-101
B146
A101
1
2
146-229
B146
A229
1
2


146-139
B146
A139
1
2
146-231
B146
A231
1
2


146-161
B146
A161
1
2
146-232
B146
A232
1
2


146-162
B146
A162
1
2
146-233
B146
A233
1
2


146-181
B146
A181
1
2
146-235
B146
A235
1
2


146-182
B146
A182
1
2
146-236
B146
A236
1
2


146-191
B146
A191
1
2
146-237
B146
A237
1
2


146-192
B146
A192
1
2
146-238
B146
A238
1
2


146-193
B146
A193
1
2
146-239
B146
A239
1
2


146-194
B146
A194
1
2
146-241
B146
A241
1
2


146-196
B146
A196
1
2
146-242
B146
A242
1
2


146-197
B146
A197
1
2
146-243
B146
A243
1
2


146-199
B146
A199
1
2
146-246
B146
A246
1
2


146-200
B146
A200
1
2
146-247
B146
A247
1
2


146-201
B146
A201
1
2
146-248
B146
A248
1
2


146-203
B146
A203
1
2
146-249
B146
A249
1
2


146-206
B146
A206
1
2
146-250
B146
A250
1
2

























TABLE 30





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







183-1
B183
A1
1
2
183-208
B183
A208
1
2


183-2
B183
A2
1
2
183-209
B183
A209
1
2


183-3
B183
A3
1
2
183-212
B183
A212
1
2


183-5
B183
A5
1
2
183-213
B183
A213
1
2


183-8
B183
A8
1
2
183-214
B183
A214
1
2


183-35
B183
A35
1
2
183-215
B183
A215
1
2


183-36
B183
A36
1
2
183-216
B183
A216
1
2


183-45
B183
A45
1
2
183-217
B183
A217
1
2


183-47
B183
A47
1
2
183-221
B183
A221
1
2


183-49
B183
A49
1
2
183-222
B183
A222
1
2


183-60
B183
A60
1
2
183-224
B183
A224
1
2


183-86
B183
A86
1
2
183-225
B183
A225
1
2


183-94
B183
A94
1
2
183-226
B183
A226
1
2


183-99
B183
A99
1
2
183-228
B183
A228
1
2


183-101
B183
A101
1
2
183-229
B183
A229
1
2


183-139
B183
A139
1
2
183-231
B183
A231
1
2


183-161
B183
A161
1
2
183-232
B183
A232
1
2


183-162
B183
A162
1
2
183-233
B183
A233
1
2


183-181
B183
A181
1
2
183-235
B183
A235
1
2


183-182
B183
A182
1
2
183-236
B183
A236
1
2


183-191
B183
A191
1
2
183-237
B183
A237
1
2


183-192
B183
A192
1
2
183-238
B183
A238
1
2


183-193
B183
A193
1
2
183-239
B183
A239
1
2


183-194
B183
A194
1
2
183-241
B183
A241
1
2


183-196
B183
A196
1
2
183-242
B183
A242
1
2


183-197
B183
A197
1
2
183-243
B183
A243
1
2


183-199
B183
A199
1
2
183-246
B183
A246
1
2


183-200
B183
A200
1
2
183-247
B183
A247
1
2


183-201
B183
A201
1
2
183-248
B183
A248
1
2


183-203
B183
A203
1
2
183-249
B183
A249
1
2


183-206
B183
A206
1
2
183-250
B183
A250
1
2

























TABLE 31





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







201-1
B201
A1
1
2
201-208
B201
A208
1
2


201-2
B201
A2
1
2
201-209
B201
A209
1
2


201-3
B201
A3
1
2
201-212
B201
A212
1
2


201-5
B201
A5
1
2
201-213
B201
A213
1
2


201-8
B201
A8
1
2
201-214
B201
A214
1
2


201-35
B201
A35
1
2
201-215
B201
A215
1
2


201-36
B201
A36
1
2
201-216
B201
A216
1
2


201-45
B201
A45
1
2
201-217
B201
A217
1
2


201-47
B201
A47
1
2
201-221
B201
A221
1
2


201-49
B201
A49
1
2
201-222
B201
A222
1
2


201-60
B201
A60
1
2
201-224
B201
A224
1
2


201-86
B201
A86
1
2
201-225
B201
A225
1
2


201-94
B201
A94
1
2
201-226
B201
A226
1
2


201-99
B201
A99
1
2
201-228
B201
A228
1
2


201-101
B201
A101
1
2
201-229
B201
A229
1
2


201-139
B201
A139
1
2
201-231
B201
A231
1
2


201-161
B201
A161
1
2
201-232
B201
A232
1
2


201-162
B201
A162
1
2
201-233
B201
A233
1
2


201-181
B201
A181
1
2
201-235
B201
A235
1
2


201-182
B201
A182
1
2
201-236
B201
A236
1
2


201-191
B201
A191
1
2
201-237
B201
A237
1
2


201-192
B201
A192
1
2
201-238
B201
A238
1
2


201-193
B201
A193
1
2
201-239
B201
A239
1
2


201-194
B201
A194
1
2
201-241
B201
A241
1
2


201-196
B201
A196
1
2
201-242
B201
A242
1
2


201-197
B201
A197
1
2
201-243
B201
A243
1
2


201-199
B201
A199
1
2
201-246
B201
A246
1
2


201-200
B201
A200
1
2
201-247
B201
A247
1
2


201-201
B201
A201
1
2
201-248
B201
A248
1
2


201-203
B201
A203
1
2
201-249
B201
A249
1
2


201-206
B201
A206
1
2
201-250
B201
A250
1
2

























TABLE 32





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







214-1
B214
A1
1
2
214-208
B214
A208
1
2


214-2
B214
A2
1
2
214-209
B214
A209
1
2


214-3
B214
A3
1
2
214-212
B214
A212
1
2


214-5
B214
A5
1
2
214-213
B214
A213
1
2


214-8
B214
A8
1
2
214-214
B214
A214
1
2


214-35
B214
A35
1
2
214-215
B214
A215
1
2


214-36
B214
A36
1
2
214-216
B214
A216
1
2


214-45
B214
A45
1
2
214-217
B214
A217
1
2


214-47
B214
A47
1
2
214-221
B214
A221
1
2


214-49
B214
A49
1
2
214-222
B214
A222
1
2


214-60
B214
A60
1
2
214-224
B214
A224
1
2


214-86
B214
A86
1
2
214-225
B214
A225
1
2


214-94
B214
A94
1
2
214-226
B214
A226
1
2


214-99
B214
A99
1
2
214-228
B214
A228
1
2


214-101
B214
A101
1
2
214-229
B214
A229
1
2


214-139
B214
A139
1
2
214-231
B214
A231
1
2


214-161
B214
A161
1
2
214-232
B214
A232
1
2


214-162
B214
A162
1
2
214-233
B214
A233
1
2


214-181
B214
A181
1
2
214-235
B214
A235
1
2


214-182
B214
A182
1
2
214-236
B214
A236
1
2


214-191
B214
A191
1
2
214-237
B214
A237
1
2


214-192
B214
A192
1
2
214-238
B214
A238
1
2


214-193
B214
A193
1
2
214-239
B214
A239
1
2


214-194
B214
A194
1
2
214-241
B214
A241
1
2


214-196
B214
A196
1
2
214-242
B214
A242
1
2


214-197
B214
A197
1
2
214-243
B214
A243
1
2


214-199
B214
A199
1
2
214-246
B214
A246
1
2


214-200
B214
A200
1
2
214-247
B214
A247
1
2


214-201
B214
A201
1
2
214-248
B214
A248
1
2


214-203
B214
A203
1
2
214-249
B214
A249
1
2


214-206
B214
A206
1
2
214-250
B214
A250
1
2

























TABLE 33





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







223-1
B223
A1
1
2
223-208
B223
A208
1
2


223-2
B223
A2
1
2
223-209
B223
A209
1
2


223-3
B223
A3
1
2
223-212
B223
A212
1
2


223-5
B223
A5
1
2
223-213
B223
A213
1
2


223-8
B223
A8
1
2
223-214
B223
A214
1
2


223-35
B223
A35
1
2
223-215
B223
A215
1
2


223-36
B223
A36
1
2
223-216
B223
A216
1
2


223-45
B223
A45
1
2
223-217
B223
A217
1
2


223-47
B223
A47
1
2
223-221
B223
A221
1
2


223-49
B223
A49
1
2
223-222
B223
A222
1
2


223-60
B223
A60
1
2
223-224
B223
A224
1
2


223-86
B223
A86
1
2
223-225
B223
A225
1
2


223-94
B223
A94
1
2
223-226
B223
A226
1
2


223-99
B223
A99
1
2
223-228
B223
A228
1
2


223-101
B223
A101
1
2
223-229
B223
A229
1
2


223-139
B223
A139
1
2
223-231
B223
A231
1
2


223-161
B223
A161
1
2
223-232
B223
A232
1
2


223-162
B223
A162
1
2
223-233
B223
A233
1
2


223-181
B223
A181
1
2
223-235
B223
A235
1
2


223-182
B223
A182
1
2
223-236
B223
A236
1
2


223-191
B223
A191
1
2
223-237
B223
A237
1
2


223-192
B223
A192
1
2
223-238
B223
A238
1
2


223-193
B223
A193
1
2
223-239
B223
A239
1
2


223-194
B223
A194
1
2
223-241
B223
A241
1
2


223-196
B223
A196
1
2
223-242
B223
A242
1
2


223-197
B223
A197
1
2
223-243
B223
A243
1
2


223-199
B223
A199
1
2
223-246
B223
A246
1
2


223-200
B223
A200
1
2
223-247
B223
A247
1
2


223-201
B223
A201
1
2
223-248
B223
A248
1
2


223-203
B223
A203
1
2
223-249
B223
A249
1
2


223-206
B223
A206
1
2
223-250
B223
A250
1
2

























TABLE 34





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







242-1
B242
A1
1
2
242-208
B242
A208
1
2


242-2
B242
A2
1
2
242-209
B242
A209
1
2


242-3
B242
A3
1
2
242-212
B242
A212
1
2


242-5
B242
A5
1
2
242-213
B242
A213
1
2


242-8
B242
A8
1
2
242-214
B242
A214
1
2


242-35
B242
A35
1
2
242-215
B242
A215
1
2


242-36
B242
A36
1
2
242-216
B242
A216
1
2


242-45
B242
A45
1
2
242-217
B242
A217
1
2


242-47
B242
A47
1
2
242-221
B242
A221
1
2


242-49
B242
A49
1
2
242-222
B242
A222
1
2


242-60
B242
A60
1
2
242-224
B242
A224
1
2


242-86
B242
A86
1
2
242-225
B242
A225
1
2


242-94
B242
A94
1
2
242-226
B242
A226
1
2


242-99
B242
A99
1
2
242-228
B242
A228
1
2


242-101
B242
A101
1
2
242-229
B242
A229
1
2


242-139
B242
A139
1
2
242-231
B242
A231
1
2


242-161
B242
A161
1
2
242-232
B242
A232
1
2


242-162
B242
A162
1
2
242-233
B242
A233
1
2


242-181
B242
A181
1
2
242-235
B242
A235
1
2


242-182
B242
A182
1
2
242-236
B242
A236
1
2


242-191
B242
A191
1
2
242-237
B242
A237
1
2


242-192
B242
A192
1
2
242-238
B242
A238
1
2


242-193
B242
A193
1
2
242-239
B242
A239
1
2


242-194
B242
A194
1
2
242-241
B242
A241
1
2


242-196
B242
A196
1
2
242-242
B242
A242
1
2


242-197
B242
A197
1
2
242-243
B242
A243
1
2


242-199
B242
A199
1
2
242-246
B242
A246
1
2


242-200
B242
A200
1
2
242-247
B242
A247
1
2


242-201
B242
A201
1
2
242-248
B242
A248
1
2


242-203
B242
A203
1
2
242-249
B242
A249
1
2


242-206
B242
A206
1
2
242-250
B242
A250
1
2

























TABLE 35





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







253-1
B253
A1
1
2
253-208
B253
A208
1
2


253-2
B253
A2
1
2
253-209
B253
A209
1
2


253-3
B253
A3
1
2
253-212
B253
A212
1
2


253-5
B253
A5
1
2
253-213
B253
A213
1
2


253-8
B253
A8
1
2
253-214
B253
A214
1
2


253-35
B253
A35
1
2
253-215
B253
A215
1
2


253-36
B253
A36
1
2
253-216
B253
A216
1
2


253-45
B253
A45
1
2
253-217
B253
A217
1
2


253-47
B253
A47
1
2
253-221
B253
A221
1
2


253-49
B253
A49
1
2
253-222
B253
A222
1
2


253-60
B253
A60
1
2
253-224
B253
A224
1
2


253-86
B253
A86
1
2
253-225
B253
A225
1
2


253-94
B253
A94
1
2
253-226
B253
A226
1
2


253-99
B253
A99
1
2
253-228
B253
A228
1
2


253-101
B253
A101
1
2
253-229
B253
A229
1
2


253-139
B253
A139
1
2
253-231
B253
A231
1
2


253-161
B253
A161
1
2
253-232
B253
A232
1
2


253-162
B253
A162
1
2
253-233
B253
A233
1
2


253-181
B253
A181
1
2
253-235
B253
A235
1
2


253-182
B253
A182
1
2
253-236
B253
A236
1
2


253-191
B253
A191
1
2
253-237
B253
A237
1
2


253-192
B253
A192
1
2
253-238
B253
A238
1
2


253-193
B253
A193
1
2
253-239
B253
A239
1
2


253-194
B253
A194
1
2
253-241
B253
A241
1
2


253-196
B253
A196
1
2
253-242
B253
A242
1
2


253-197
B253
A197
1
2
253-243
B253
A243
1
2


253-199
B253
A199
1
2
253-246
B253
A246
1
2


253-200
B253
A200
1
2
253-247
B253
A247
1
2


253-201
B253
A201
1
2
253-248
B253
A248
1
2


253-203
B253
A203
1
2
253-249
B253
A249
1
2


253-206
B253
A206
1
2
253-250
B253
A250
1
2

























TABLE 36





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







265-1
B265
A1
1
2
265-208
B265
A208
1
2


265-2
B265
A2
1
2
265-209
B265
A209
1
2


265-3
B265
A3
1
2
265-212
B265
A212
1
2


265-5
B265
A5
1
2
265-213
B265
A213
1
2


265-8
B265
A8
1
2
265-214
B265
A214
1
2


265-35
B265
A35
1
2
265-215
B265
A215
1
2


265-36
B265
A36
1
2
265-216
B265
A216
1
2


265-45
B265
A45
1
2
265-217
B265
A217
1
2


265-47
B265
A47
1
2
265-221
B265
A221
1
2


265-49
B265
A49
1
2
265-222
B265
A222
1
2


265-60
B265
A60
1
2
265-224
B265
A224
1
2


265-86
B265
A86
1
2
265-225
B265
A225
1
2


265-94
B265
A94
1
2
265-226
B265
A226
1
2


265-99
B265
A99
1
2
265-228
B265
A228
1
2


265-101
B265
A101
1
2
265-229
B265
A229
1
2


265-139
B265
A139
1
2
265-231
B265
A231
1
2


265-161
B265
A161
1
2
265-232
B265
A232
1
2


265-162
B265
A162
1
2
265-233
B265
A233
1
2


265-181
B265
A181
1
2
265-235
B265
A235
1
2


265-182
B265
A182
1
2
265-236
B265
A236
1
2


265-191
B265
A191
1
2
265-237
B265
A237
1
2


265-192
B265
A192
1
2
265-238
B265
A238
1
2


265-193
B265
A193
1
2
265-239
B265
A239
1
2


265-194
B265
A194
1
2
265-241
B265
A241
1
2


265-196
B265
A196
1
2
265-242
B265
A242
1
2


265-197
B265
A197
1
2
265-243
B265
A243
1
2


265-199
B265
A199
1
2
265-246
B265
A246
1
2


265-200
B265
A200
1
2
265-247
B265
A247
1
2


265-201
B265
A201
1
2
265-248
B265
A248
1
2


265-203
B265
A203
1
2
265-249
B265
A249
1
2


265-206
B265
A206
1
2
265-250
B265
A250
1
2

























TABLE 37





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







282-1
B282
A1
1
2
282-208
B282
A208
1
2


282-2
B282
A2
1
2
282-209
B282
A209
1
2


282-3
B282
A3
1
2
282-212
B282
A212
1
2


282-5
B282
A5
1
2
282-213
B282
A213
1
2


282-8
B282
A8
1
2
282-214
B282
A214
1
2


282-35
B282
A35
1
2
282-215
B282
A215
1
2


282-36
B282
A36
1
2
282-216
B282
A216
1
2


282-45
B282
A45
1
2
282-217
B282
A217
1
2


282-47
B282
A47
1
2
282-221
B282
A221
1
2


282-49
B282
A49
1
2
282-222
B282
A222
1
2


282-60
B282
A60
1
2
282-224
B282
A224
1
2


282-86
B282
A86
1
2
282-225
B282
A225
1
2


282-94
B282
A94
1
2
282-226
B282
A226
1
2


282-99
B282
A99
1
2
282-228
B282
A228
1
2


282-101
B282
A101
1
2
282-229
B282
A229
1
2


282-139
B282
A139
1
2
282-231
B282
A231
1
2


282-161
B282
A161
1
2
282-232
B282
A232
1
2


282-162
B282
A162
1
2
282-233
B282
A233
1
2


282-181
B282
A181
1
2
282-235
B282
A235
1
2


282-182
B282
A182
1
2
282-236
B282
A236
1
2


282-191
B282
A191
1
2
282-237
B282
A237
1
2


282-192
B282
A192
1
2
282-238
B282
A238
1
2


282-193
B282
A193
1
2
282-239
B282
A239
1
2


282-194
B282
A194
1
2
282-241
B282
A241
1
2


282-196
B282
A196
1
2
282-242
B282
A242
1
2


282-197
B282
A197
1
2
282-243
B282
A243
1
2


282-199
B282
A199
1
2
282-246
B282
A246
1
2


282-200
B282
A200
1
2
282-247
B282
A247
1
2


282-201
B282
A201
1
2
282-248
B282
A248
1
2


282-203
B282
A203
1
2
282-249
B282
A249
1
2


282-206
B282
A206
1
2
282-250
B282
A250
1
2

























TABLE 38





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







287-1
B287
A1
1
2
287-208
B287
A208
1
2


287-2
B287
A2
1
2
287-209
B287
A209
1
2


287-3
B287
A3
1
2
287-212
B287
A212
1
2


287-5
B287
A5
1
2
287-213
B287
A213
1
2


287-8
B287
A8
1
2
287-214
B287
A214
1
2


287-35
B287
A35
1
2
287-215
B287
A215
1
2


287-36
B287
A36
1
2
287-216
B287
A216
1
2


287-45
B287
A45
1
2
287-217
B287
A217
1
2


287-47
B287
A47
1
2
287-221
B287
A221
1
2


287-49
B287
A49
1
2
287-222
B287
A222
1
2


287-60
B287
A60
1
2
287-224
B287
A224
1
2


287-86
B287
A86
1
2
287-225
B287
A225
1
2


287-94
B287
A94
1
2
287-226
B287
A226
1
2


287-99
B287
A99
1
2
287-228
B287
A228
1
2


287-101
B287
A101
1
2
287-229
B287
A229
1
2


287-139
B287
A139
1
2
287-231
B287
A231
1
2


287-161
B287
A161
1
2
287-232
B287
A232
1
2


287-162
B287
A162
1
2
287-233
B287
A233
1
2


287-181
B287
A181
1
2
287-235
B287
A235
1
2


287-182
B287
A182
1
2
287-236
B287
A236
1
2


287-191
B287
A191
1
2
287-237
B287
A237
1
2


287-192
B287
A192
1
2
287-238
B287
A238
1
2


287-193
B287
A193
1
2
287-239
B287
A239
1
2


287-194
B287
A194
1
2
287-241
B287
A241
1
2


287-196
B287
A196
1
2
287-242
B287
A242
1
2


287-197
B287
A197
1
2
287-243
B287
A243
1
2


287-199
B287
A199
1
2
287-246
B287
A246
1
2


287-200
B287
A200
1
2
287-247
B287
A247
1
2


287-201
B287
A201
1
2
287-248
B287
A248
1
2


287-203
B287
A203
1
2
287-249
B287
A249
1
2


287-206
B287
A206
1
2
287-250
B287
A250
1
2

























TABLE 39





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







293-1
B293
A1
1
2
293-208
B293
A208
1
2


293-2
B293
A2
1
2
293-209
B293
A209
1
2


293-3
B293
A3
1
2
293-212
B293
A212
1
2


293-5
B293
A5
1
2
293-213
B293
A213
1
2


293-8
B293
A8
1
2
293-214
B293
A214
1
2


293-35
B293
A35
1
2
293-215
B293
A215
1
2


293-36
B293
A36
1
2
293-216
B293
A216
1
2


293-45
B293
A45
1
2
293-217
B293
A217
1
2


293-47
B293
A47
1
2
293-221
B293
A221
1
2


293-49
B293
A49
1
2
293-222
B293
A222
1
2


293-60
B293
A60
1
2
293-224
B293
A224
1
2


293-86
B293
A86
1
2
293-225
B293
A225
1
2


293-94
B293
A94
1
2
293-226
B293
A226
1
2


293-99
B293
A99
1
2
293-228
B293
A228
1
2


293-101
B293
A101
1
2
293-229
B293
A229
1
2


293-139
B293
A139
1
2
293-231
B293
A231
1
2


293-161
B293
A161
1
2
293-232
B293
A232
1
2


293-162
B293
A162
1
2
293-233
B293
A233
1
2


293-181
B293
A181
1
2
293-235
B293
A235
1
2


293-182
B293
A182
1
2
293-236
B293
A236
1
2


293-191
B293
A191
1
2
293-237
B293
A237
1
2


293-192
B293
A192
1
2
293-238
B293
A238
1
2


293-193
B293
A193
1
2
293-239
B293
A239
1
2


293-194
B293
A194
1
2
293-241
B293
A241
1
2


293-196
B293
A196
1
2
293-242
B293
A242
1
2


293-197
B293
A197
1
2
293-243
B293
A243
1
2


293-199
B293
A199
1
2
293-246
B293
A246
1
2


293-200
B293
A200
1
2
293-247
B293
A247
1
2


293-201
B293
A201
1
2
293-248
B293
A248
1
2


293-203
B293
A203
1
2
293-249
B293
A249
1
2


293-206
B293
A206
1
2
293-250
B293
A250
1
2

























TABLE 40





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







295-1
B295
A1
1
2
295-208
B295
A208
1
2


295-2
B295
A2
1
2
295-209
B295
A209
1
2


295-3
B295
A3
1
2
295-212
B295
A212
1
2


295-5
B295
A5
1
2
295-213
B295
A213
1
2


295-8
B295
A8
1
2
295-214
B295
A214
1
2


295-35
B295
A35
1
2
295-215
B295
A215
1
2


295-36
B295
A36
1
2
295-216
B295
A216
1
2


295-45
B295
A45
1
2
295-217
B295
A217
1
2


295-47
B295
A47
1
2
295-221
B295
A221
1
2


295-49
B295
A49
1
2
295-222
B295
A222
1
2


295-60
B295
A60
1
2
295-224
B295
A224
1
2


295-86
B295
A86
1
2
295-225
B295
A225
1
2


295-94
B295
A94
1
2
295-226
B295
A226
1
2


295-99
B295
A99
1
2
295-228
B295
A228
1
2


295-101
B295
A101
1
2
295-229
B295
A229
1
2


295-139
B295
A139
1
2
295-231
B295
A231
1
2


295-161
B295
A161
1
2
295-232
B295
A232
1
2


295-162
B295
A162
1
2
295-233
B295
A233
1
2


295-181
B295
A181
1
2
295-235
B295
A235
1
2


295-182
B295
A182
1
2
295-236
B295
A236
1
2


295-191
B295
A191
1
2
295-237
B295
A237
1
2


295-192
B295
A192
1
2
295-238
B295
A238
1
2


295-193
B295
A193
1
2
295-239
B295
A239
1
2


295-194
B295
A194
1
2
295-241
B295
A241
1
2


295-196
B295
A196
1
2
295-242
B295
A242
1
2


295-197
B295
A197
1
2
295-243
B295
A243
1
2


295-199
B295
A199
1
2
295-246
B295
A246
1
2


295-200
B295
A200
1
2
295-247
B295
A247
1
2


295-201
B295
A201
1
2
295-248
B295
A248
1
2


295-203
B295
A203
1
2
295-249
B295
A249
1
2


295-206
B295
A206
1
2
295-250
B295
A250
1
2

























TABLE 41





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







312-1
B312
A1
1
2
312-208
B312
A208
1
2


312-2
B312
A2
1
2
312-209
B312
A209
1
2


312-3
B312
A3
1
2
312-212
B312
A212
1
2


312-5
B312
A5
1
2
312-213
B312
A213
1
2


312-8
B312
A8
1
2
312-214
B312
A214
1
2


312-35
B312
A35
1
2
312-215
B312
A215
1
2


312-36
B312
A36
1
2
312-216
B312
A216
1
2


312-45
B312
A45
1
2
312-217
B312
A217
1
2


312-47
B312
A47
1
2
312-221
B312
A221
1
2


312-49
B312
A49
1
2
312-222
B312
A222
1
2


312-60
B312
A60
1
2
312-224
B312
A224
1
2


312-86
B312
A86
1
2
312-225
B312
A225
1
2


312-94
B312
A94
1
2
312-226
B312
A226
1
2


312-99
B312
A99
1
2
312-228
B312
A228
1
2


312-101
B312
A101
1
2
312-229
B312
A229
1
2


312-139
B312
A139
1
2
312-231
B312
A231
1
2


312-161
B312
A161
1
2
312-232
B312
A232
1
2


312-162
B312
A162
1
2
312-233
B312
A233
1
2


312-181
B312
A181
1
2
312-235
B312
A235
1
2


312-182
B312
A182
1
2
312-236
B312
A236
1
2


312-191
B312
A191
1
2
312-237
B312
A237
1
2


312-192
B312
A192
1
2
312-238
B312
A238
1
2


312-193
B312
A193
1
2
312-239
B312
A239
1
2


312-194
B312
A194
1
2
312-241
B312
A241
1
2


312-196
B312
A196
1
2
312-242
B312
A242
1
2


312-197
B312
A197
1
2
312-243
B312
A243
1
2


312-199
B312
A199
1
2
312-246
B312
A246
1
2


312-200
B312
A200
1
2
312-247
B312
A247
1
2


312-201
B312
A201
1
2
312-248
B312
A248
1
2


312-203
B312
A203
1
2
312-249
B312
A249
1
2


312-206
B312
A206
1
2
312-250
B312
A250
1
2

























TABLE 42





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







327-1
B327
A1
1
2
327-208
B327
A208
1
2


327-2
B327
A2
1
2
327-209
B327
A209
1
2


327-3
B327
A3
1
2
327-212
B327
A212
1
2


327-5
B327
A5
1
2
327-213
B327
A213
1
2


327-8
B327
A8
1
2
327-214
B327
A214
1
2


327-35
B327
A35
1
2
327-215
B327
A215
1
2


327-36
B327
A36
1
2
327-216
B327
A216
1
2


327-45
B327
A45
1
2
327-217
B327
A217
1
2


327-47
B327
A47
1
2
327-221
B327
A221
1
2


327-49
B327
A49
1
2
327-222
B327
A222
1
2


327-60
B327
A60
1
2
327-224
B327
A224
1
2


327-86
B327
A86
1
2
327-225
B327
A225
1
2


327-94
B327
A94
1
2
327-226
B327
A226
1
2


327-99
B327
A99
1
2
327-228
B327
A228
1
2


327-101
B327
A101
1
2
327-229
B327
A229
1
2


327-139
B327
A139
1
2
327-231
B327
A231
1
2


327-161
B327
A161
1
2
327-232
B327
A232
1
2


327-162
B327
A162
1
2
327-233
B327
A233
1
2


327-181
B327
A181
1
2
327-235
B327
A235
1
2


327-182
B327
A182
1
2
327-236
B327
A236
1
2


327-191
B327
A191
1
2
327-237
B327
A237
1
2


327-192
B327
A192
1
2
327-238
B327
A238
1
2


327-193
B327
A193
1
2
327-239
B327
A239
1
2


327-194
B327
A194
1
2
327-241
B327
A241
1
2


327-196
B327
A196
1
2
327-242
B327
A242
1
2


327-197
B327
A197
1
2
327-243
B327
A243
1
2


327-199
B327
A199
1
2
327-246
B327
A246
1
2


327-200
B327
A200
1
2
327-247
B327
A247
1
2


327-201
B327
A201
1
2
327-248
B327
A248
1
2


327-203
B327
A203
1
2
327-249
B327
A249
1
2


327-206
B327
A206
1
2
327-250
B327
A250
1
2

























TABLE 43





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







2-1R
B2
A1
2
1
2-208R
B2
A208
2
1


2-2R
B2
A2
2
1
2-209R
B2
A209
2
1


2-3R
B2
A3
2
1
2-212R
B2
A212
2
1


2-5R
B2
A5
2
1
2-213R
B2
A213
2
1


2-8R
B2
A8
2
1
2-214R
B2
A214
2
1


2-35R
B2
A35
2
1
2-215R
B2
A215
2
1


2-36R
B2
A36
2
1
2-216R
B2
A216
2
1


2-45R
B2
A45
2
1
2-217R
B2
A217
2
1


2-47R
B2
A47
2
1
2-221R
B2
A221
2
1


2-49R
B2
A49
2
1
2-222R
B2
A222
2
1


2-60R
B2
A60
2
1
2-224R
B2
A224
2
1


2-86R
B2
A86
2
1
2-225R
B2
A225
2
1


2-94R
B2
A94
2
1
2-226R
B2
A226
2
1


2-99R
B2
A99
2
1
2-228R
B2
A228
2
1


2-101R
B2
A101
2
1
2-229R
B2
A229
2
1


2-139R
B2
A139
2
1
2-231R
B2
A231
2
1


2-161R
B2
A161
2
1
2-232R
B2
A232
2
1


2-162R
B2
A162
2
1
2-233R
B2
A233
2
1


2-181R
B2
A181
2
1
2-235R
B2
A235
2
1


2-182R
B2
A182
2
1
2-236R
B2
A236
2
1


2-191R
B2
A191
2
1
2-237R
B2
A237
2
1


2-192R
B2
A192
2
1
2-238R
B2
A238
2
1


2-193R
B2
A193
2
1
2-239R
B2
A239
2
1


2-194R
B2
A194
2
1
2-241R
B2
A241
2
1


2-196R
B2
A196
2
1
2-242R
B2
A242
2
1


2-197R
B2
A197
2
1
2-243R
B2
A243
2
1


2-199R
B2
A199
2
1
2-246R
B2
A246
2
1


2-200R
B2
A200
2
1
2-247R
B2
A247
2
1


2-201R
B2
A201
2
1
2-248R
B2
A248
2
1


2-203R
B2
A203
2
1
2-249R
B2
A249
2
1


2-206R
B2
A206
2
1
2-250R
B2
A250
2
1

























TABLE 44





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







4-1R
B4
A1
2
1
4-208R
B4
A208
2
1


4-2R
B4
A2
2
1
4-209R
B4
A209
2
1


4-3R
B4
A3
2
1
4-212R
B4
A212
2
1


4-5R
B4
A5
2
1
4-213R
B4
A213
2
1


4-8R
B4
A8
2
1
4-214R
B4
A214
2
1


4-35R
B4
A35
2
1
4-215R
B4
A215
2
1


4-36R
B4
A36
2
1
4-216R
B4
A216
2
1


4-45R
B4
A45
2
1
4-217R
B4
A217
2
1


4-47R
B4
A47
2
1
4-221R
B4
A221
2
1


4-49R
B4
A49
2
1
4-222R
B4
A222
2
1


4-60R
B4
A60
2
1
4-224R
B4
A224
2
1


4-86R
B4
A86
2
1
4-225R
B4
A225
2
1


4-94R
B4
A94
2
1
4-226R
B4
A226
2
1


4-99R
B4
A99
2
1
4-228R
B4
A228
2
1


4-101R
B4
A101
2
1
4-229R
B4
A229
2
1


4-139R
B4
A139
2
1
4-231R
B4
A231
2
1


4-161R
B4
A161
2
1
4-232R
B4
A232
2
1


4-162R
B4
A162
2
1
4-233R
B4
A233
2
1


4-181R
B4
A181
2
1
4-235R
B4
A235
2
1


4-182R
B4
A182
2
1
4-236R
B4
A236
2
1


4-191R
B4
A191
2
1
4-237R
B4
A237
2
1


4-192R
B4
A192
2
1
4-238R
B4
A238
2
1


4-193R
B4
A193
2
1
4-239R
B4
A239
2
1


4-194R
B4
A194
2
1
4-241R
B4
A241
2
1


4-196R
B4
A196
2
1
4-242R
B4
A242
2
1


4-197R
B4
A197
2
1
4-243R
B4
A243
2
1


4-199R
B4
A199
2
1
4-246R
B4
A246
2
1


4-200R
B4
A200
2
1
4-247R
B4
A247
2
1


4-201R
B4
A201
2
1
4-248R
B4
A248
2
1


4-203R
B4
A203
2
1
4-249R
B4
A249
2
1


4-206R
B4
A206
2
1
4-250R
B4
A250
2
1

























TABLE 45





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







6-1R
B6
A1
2
1
6-208R
B6
A208
2
1


6-2R
B6
A2
2
1
6-209R
B6
A209
2
1


6-3R
B6
A3
2
1
6-212R
B6
A212
2
1


6-5R
B6
A5
2
1
6-213R
B6
A213
2
1


6-8R
B6
A8
2
1
6-214R
B6
A214
2
1


6-35R
B6
A35
2
1
6-215R
B6
A215
2
1


6-36R
B6
A36
2
1
6-216R
B6
A216
2
1


6-45R
B6
A45
2
1
6-217R
B6
A217
2
1


6-47R
B6
A47
2
1
6-221R
B6
A221
2
1


6-49R
B6
A49
2
1
6-222R
B6
A222
2
1


6-60R
B6
A60
2
1
6-224R
B6
A224
2
1


6-86R
B6
A86
2
1
6-225R
B6
A225
2
1


6-94R
B6
A94
2
1
6-226R
B6
A226
2
1


6-99R
B6
A99
2
1
6-228R
B6
A228
2
1


6-101R
B6
A101
2
1
6-229R
B6
A229
2
1


6-139R
B6
A139
2
1
6-231R
B6
A231
2
1


6-161R
B6
A161
2
1
6-232R
B6
A232
2
1


6-162R
B6
A162
2
1
6-233R
B6
A233
2
1


6-181R
B6
A181
2
1
6-235R
B6
A235
2
1


6-182R
B6
A182
2
1
6-236R
B6
A236
2
1


6-191R
B6
A191
2
1
6-237R
B6
A237
2
1


6-192R
B6
A192
2
1
6-238R
B6
A238
2
1


6-193R
B6
A193
2
1
6-239R
B6
A239
2
1


6-194R
B6
A194
2
1
6-241R
B6
A241
2
1


6-196R
B6
A196
2
1
6-242R
B6
A242
2
1


6-197R
B6
A197
2
1
6-243R
B6
A243
2
1


6-199R
B6
A199
2
1
6-246R
B6
A246
2
1


6-200R
B6
A200
2
1
6-247R
B6
A247
2
1


6-201R
B6
A201
2
1
6-248R
B6
A248
2
1


6-203R
B6
A203
2
1
6-249R
B6
A249
2
1


6-206R
B6
A206
2
1
6-250R
B6
A250
2
1

























TABLE 46





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







22-1R
B22
A1
2
1
22-208R
B22
A208
2
1


22-2R
B22
A2
2
1
22-209R
B22
A209
2
1


22-3R
B22
A3
2
1
22-212R
B22
A212
2
1


22-5R
B22
A5
2
1
22-213R
B22
A213
2
1


22-8R
B22
A8
2
1
22-214R
B22
A214
2
1


22-35R
B22
A35
2
1
22-215R
B22
A215
2
1


22-36R
B22
A36
2
1
22-216R
B22
A216
2
1


22-45R
B22
A45
2
1
22-217R
B22
A217
2
1


22-47R
B22
A47
2
1
22-221R
B22
A221
2
1


22-49R
B22
A49
2
1
22-222R
B22
A222
2
1


22-60R
B22
A60
2
1
22-224R
B22
A224
2
1


22-86R
B22
A86
2
1
22-225R
B22
A225
2
1


22-94R
B22
A94
2
1
22-226R
B22
A226
2
1


22-99R
B22
A99
2
1
22-228R
B22
A228
2
1


22-101R
B22
A101
2
1
22-229R
B22
A229
2
1


22-139R
B22
A139
2
1
22-231R
B22
A231
2
1


22-161R
B22
A161
2
1
22-232R
B22
A232
2
1


22-162R
B22
A162
2
1
22-233R
B22
A233
2
1


22-181R
B22
A181
2
1
22-235R
B22
A235
2
1


22-182R
B22
A182
2
1
22-236R
B22
A236
2
1


22-191R
B22
A191
2
1
22-237R
B22
A237
2
1


22-192R
B22
A192
2
1
22-238R
B22
A238
2
1


22-193R
B22
A193
2
1
22-239R
B22
A239
2
1


22-194R
B22
A194
2
1
22-241R
B22
A241
2
1


22-196R
B22
A196
2
1
22-242R
B22
A242
2
1


22-197R
B22
A197
2
1
22-243R
B22
A243
2
1


22-199R
B22
A199
2
1
22-246R
B22
A246
2
1


22-200R
B22
A200
2
1
22-247R
B22
A247
2
1


22-201R
B22
A201
2
1
22-248R
B22
A248
2
1


22-203R
B22
A203
2
1
22-249R
B22
A249
2
1


22-206R
B22
A206
2
1
22-250R
B22
A250
2
1

























TABLE 47





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







24-1R
B24
A1
2
1
24-208R
B24
A208
2
1


24-2R
B24
A2
2
1
24-209R
B24
A209
2
1


24-3R
B24
A3
2
1
24-212R
B24
A212
2
1


24-5R
B24
A5
2
1
24-213R
B24
A213
2
1


24-8R
B24
A8
2
1
24-214R
B24
A214
2
1


24-35R
B24
A35
2
1
24-215R
B24
A215
2
1


24-36R
B24
A36
2
1
24-216R
B24
A216
2
1


24-45R
B24
A45
2
1
24-217R
B24
A217
2
1


24-47R
B24
A47
2
1
24-221R
B24
A221
2
1


24-49R
B24
A49
2
1
24-222R
B24
A222
2
1


24-60R
B24
A60
2
1
24-224R
B24
A224
2
1


24-86R
B24
A86
2
1
24-225R
B24
A225
2
1


24-94R
B24
A94
2
1
24-226R
B24
A226
2
1


24-99R
B24
A99
2
1
24-228R
B24
A228
2
1


24-101R
B24
A101
2
1
24-229R
B24
A229
2
1


24-139R
B24
A139
2
1
24-231R
B24
A231
2
1


24-161R
B24
A161
2
1
24-232R
B24
A232
2
1


24-162R
B24
A162
2
1
24-233R
B24
A233
2
1


24-181R
B24
A181
2
1
24-235R
B24
A235
2
1


24-182R
B24
A182
2
1
24-236R
B24
A236
2
1


24-191R
B24
A191
2
1
24-237R
B24
A237
2
1


24-192R
B24
A192
2
1
24-238R
B24
A238
2
1


24-193R
B24
A193
2
1
24-239R
B24
A239
2
1


24-194R
B24
A194
2
1
24-241R
B24
A241
2
1


24-196R
B24
A196
2
1
24-242R
B24
A242
2
1


24-197R
B24
A197
2
1
24-243R
B24
A243
2
1


24-199R
B24
A199
2
1
24-246R
B24
A246
2
1


24-200R
B24
A200
2
1
24-247R
B24
A247
2
1


24-201R
B24
A201
2
1
24-248R
B24
A248
2
1


24-203R
B24
A203
2
1
24-249R
B24
A249
2
1


24-206R
B24
A206
2
1
24-250R
B24
A250
2
1

























TABLE 48





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







26-1R
B26
A1
2
1
26-208R
B26
A208
2
1


26-2R
B26
A2
2
1
26-209R
B26
A209
2
1


26-3R
B26
A3
2
1
26-212R
B26
A212
2
1


26-5R
B26
A5
2
1
26-213R
B26
A213
2
1


26-8R
B26
A8
2
1
26-214R
B26
A214
2
1


26-35R
B26
A35
2
1
26-215R
B26
A215
2
1


26-36R
B26
A36
2
1
26-216R
B26
A216
2
1


26-45R
B26
A45
2
1
26-217R
B26
A217
2
1


26-47R
B26
A47
2
1
26-221R
B26
A221
2
1


26-49R
B26
A49
2
1
26-222R
B26
A222
2
1


26-60R
B26
A60
2
1
26-224R
B26
A224
2
1


26-86R
B26
A86
2
1
26-225R
B26
A225
2
1


26-94R
B26
A94
2
1
26-226R
B26
A226
2
1


26-99R
B26
A99
2
1
26-228R
B26
A228
2
1


26-101R
B26
A101
2
1
26-229R
B26
A229
2
1


26-139R
B26
A139
2
1
26-231R
B26
A231
2
1


26-161R
B26
A161
2
1
26-232R
B26
A232
2
1


26-162R
B26
A162
2
1
26-233R
B26
A233
2
1


26-181R
B26
A181
2
1
26-235R
B26
A235
2
1


26-182R
B26
A182
2
1
26-236R
B26
A236
2
1


26-191R
B26
A191
2
1
26-237R
B26
A237
2
1


26-192R
B26
A192
2
1
26-238R
B26
A238
2
1


26-193R
B26
A193
2
1
26-239R
B26
A239
2
1


26-194R
B26
A194
2
1
26-241R
B26
A241
2
1


26-196R
B26
A196
2
1
26-242R
B26
A242
2
1


26-197R
B26
A197
2
1
26-243R
B26
A243
2
1


26-199R
B26
A199
2
1
26-246R
B26
A246
2
1


26-200R
B26
A200
2
1
26-247R
B26
A247
2
1


26-201R
B26
A201
2
1
26-248R
B26
A248
2
1


26-203R
B26
A203
2
1
26-249R
B26
A249
2
1


26-206R
B26
A206
2
1
26-250R
B26
A250
2
1

























TABLE 49





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







67-1R
B67
A1
2
1
67-208R
B67
A208
2
1


67-2R
B67
A2
2
1
67-209R
B67
A209
2
1


67-3R
B67
A3
2
1
67-212R
B67
A212
2
1


67-5R
B67
A5
2
1
67-213R
B67
A213
2
1


67-8R
B67
A8
2
1
67-214R
B67
A214
2
1


67-35R
B67
A35
2
1
67-215R
B67
A215
2
1


67-36R
B67
A36
2
1
67-216R
B67
A216
2
1


67-45R
B67
A45
2
1
67-217R
B67
A217
2
1


67-47R
B67
A47
2
1
67-221R
B67
A221
2
1


67-49R
B67
A49
2
1
67-222R
B67
A222
2
1


67-60R
B67
A60
2
1
67-224R
B67
A224
2
1


67-86R
B67
A86
2
1
67-225R
B67
A225
2
1


67-94R
B67
A94
2
1
67-226R
B67
A226
2
1


67-99R
B67
A99
2
1
67-228R
B67
A228
2
1


67-101R
B67
A101
2
1
67-229R
B67
A229
2
1


67-139R
B67
A139
2
1
67-231R
B67
A231
2
1


67-161R
B67
A161
2
1
67-232R
B67
A232
2
1


67-162R
B67
A162
2
1
67-233R
B67
A233
2
1


67-181R
B67
A181
2
1
67-235R
B67
A235
2
1


67-182R
B67
A182
2
1
67-236R
B67
A236
2
1


67-191R
B67
A191
2
1
67-237R
B67
A237
2
1


67-192R
B67
A192
2
1
67-238R
B67
A238
2
1


67-193R
B67
A193
2
1
67-239R
B67
A239
2
1


67-194R
B67
A194
2
1
67-241R
B67
A241
2
1


67-196R
B67
A196
2
1
67-242R
B67
A242
2
1


67-197R
B67
A197
2
1
67-243R
B67
A243
2
1


67-199R
B67
A199
2
1
67-246R
B67
A246
2
1


67-200R
B67
A200
2
1
67-247R
B67
A247
2
1


67-201R
B67
A201
2
1
67-248R
B67
A248
2
1


67-203R
B67
A203
2
1
67-249R
B67
A249
2
1


67-206R
B67
A206
2
1
67-250R
B67
A250
2
1

























TABLE 50





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







70-1R
B70
A1
2
1
70-208R
B70
A208
2
1


70-2R
B70
A2
2
1
70-209R
B70
A209
2
1


70-3R
B70
A3
2
1
70-212R
B70
A212
2
1


70-5R
B70
A5
2
1
70-213R
B70
A213
2
1


70-8R
B70
A8
2
1
70-214R
B70
A214
2
1


70-35R
B70
A35
2
1
70-215R
B70
A215
2
1


70-36R
B70
A36
2
1
70-216R
B70
A216
2
1


70-45R
B70
A45
2
1
70-217R
B70
A217
2
1


70-47R
B70
A47
2
1
70-221R
B70
A221
2
1


70-49R
B70
A49
2
1
70-222R
B70
A222
2
1


70-60R
B70
A60
2
1
70-224R
B70
A224
2
1


70-86R
B70
A86
2
1
70-225R
B70
A225
2
1


70-94R
B70
A94
2
1
70-226R
B70
A226
2
1


70-99R
B70
A99
2
1
70-228R
B70
A228
2
1


70-101R
B70
A101
2
1
70-229R
B70
A229
2
1


70-139R
B70
A139
2
1
70-231R
B70
A231
2
1


70-161R
B70
A161
2
1
70-232R
B70
A232
2
1


70-162R
B70
A162
2
1
70-233R
B70
A233
2
1


70-181R
B70
A181
2
1
70-235R
B70
A235
2
1


70-182R
B70
A182
2
1
70-236R
B70
A236
2
1


70-191R
B70
A191
2
1
70-237R
B70
A237
2
1


70-192R
B70
A192
2
1
70-238R
B70
A238
2
1


70-193R
B70
A193
2
1
70-239R
B70
A239
2
1


70-194R
B70
A194
2
1
70-241R
B70
A241
2
1


70-196R
B70
A196
2
1
70-242R
B70
A242
2
1


70-197R
B70
A197
2
1
70-243R
B70
A243
2
1


70-199R
B70
A199
2
1
70-246R
B70
A246
2
1


70-200R
B70
A200
2
1
70-247R
B70
A247
2
1


70-201R
B70
A201
2
1
70-248R
B70
A248
2
1


70-203R
B70
A203
2
1
70-249R
B70
A249
2
1


70-206R
B70
A206
2
1
70-250R
B70
A250
2
1

























TABLE 51





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







106-1R
B106
A1
2
1
106-208R
B106
A208
2
1


106-2R
B106
A2
2
1
106-209R
B106
A209
2
1


106-3R
B106
A3
2
1
106-212R
B106
A212
2
1


106-5R
B106
A5
2
1
106-213R
B106
A213
2
1


106-8R
B106
A8
2
1
106-214R
B106
A214
2
1


106-35R
B106
A35
2
1
106-215R
B106
A215
2
1


106-36R
B106
A36
2
1
106-216R
B106
A216
2
1


106-45R
B106
A45
2
1
106-217R
B106
A217
2
1


106-47R
B106
A47
2
1
106-221R
B106
A221
2
1


106-49R
B106
A49
2
1
106-222R
B106
A222
2
1


106-60R
B106
A60
2
1
106-224R
B106
A224
2
1


106-86R
B106
A86
2
1
106-225R
B106
A225
2
1


106-94R
B106
A94
2
1
106-226R
B106
A226
2
1


106-99R
B106
A99
2
1
106-228R
B106
A228
2
1


106-101R
B106
A101
2
1
106-229R
B106
A229
2
1


106-139R
B106
A139
2
1
106-231R
B106
A231
2
1


106-161R
B106
A161
2
1
106-232R
B106
A232
2
1


106-162R
B106
A162
2
1
106-233R
B106
A233
2
1


106-181R
B106
A181
2
1
106-235R
B106
A235
2
1


106-182R
B106
A182
2
1
106-236R
B106
A236
2
1


106-191R
B106
A191
2
1
106-237R
B106
A237
2
1


106-192R
B106
A192
2
1
106-238R
B106
A238
2
1


106-193R
B106
A193
2
1
106-239R
B106
A239
2
1


106-194R
B106
A194
2
1
106-241R
B106
A241
2
1


106-196R
B106
A196
2
1
106-242R
B106
A242
2
1


106-197R
B106
A197
2
1
106-243R
B106
A243
2
1


106-199R
B106
A199
2
1
106-246R
B106
A246
2
1


106-200R
B106
A200
2
1
106-247R
B106
A247
2
1


106-201R
B106
A201
2
1
106-248R
B106
A248
2
1


106-203R
B106
A203
2
1
106-249R
B106
A249
2
1


106-206R
B106
A206
2
1
106-250R
B106
A250
2
1

























TABLE 52





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







111-1R
B111
A1
2
1
111-208R
B111
A208
2
1


111-2R
B111
A2
2
1
111-209R
B111
A209
2
1


111-3R
B111
A3
2
1
111-212R
B111
A212
2
1


111-5R
B111
A5
2
1
111-213R
B111
A213
2
1


111-8R
B111
A8
2
1
111-214R
B111
A214
2
1


111-35R
B111
A35
2
1
111-215R
B111
A215
2
1


111-36R
B111
A36
2
1
111-216R
B111
A216
2
1


111-45R
B111
A45
2
1
111-217R
B111
A217
2
1


111-47R
B111
A47
2
1
111-221R
B111
A221
2
1


111-49R
B111
A49
2
1
111-222R
B111
A222
2
1


111-60R
B111
A60
2
1
111-224R
B111
A224
2
1


111-86R
B111
A86
2
1
111-225R
B111
A225
2
1


111-94R
B111
A94
2
1
111-226R
B111
A226
2
1


111-99R
B111
A99
2
1
111-228R
B111
A228
2
1


111-101R
B111
A101
2
1
111-229R
B111
A229
2
1


111-139R
B111
A139
2
1
111-231R
B111
A231
2
1


111-161R
B111
A161
2
1
111-232R
B111
A232
2
1


111-162R
B111
A162
2
1
111-233R
B111
A233
2
1


111-181R
B111
A181
2
1
111-235R
B111
A235
2
1


111-182R
B111
A182
2
1
111-236R
B111
A236
2
1


111-191R
B111
A191
2
1
111-237R
B111
A237
2
1


111-192R
B111
A192
2
1
111-238R
B111
A238
2
1


111-193R
B111
A193
2
1
111-239R
B111
A239
2
1


111-194R
B111
A194
2
1
111-241R
B111
A241
2
1


111-196R
B111
A196
2
1
111-242R
B111
A242
2
1


111-197R
B111
A197
2
1
111-243R
B111
A243
2
1


111-199R
B111
A199
2
1
111-246R
B111
A246
2
1


111-200R
B111
A200
2
1
111-247R
B111
A247
2
1


111-201R
B111
A201
2
1
111-248R
B111
A248
2
1


111-203R
B111
A203
2
1
111-249R
B111
A249
2
1


111-206R
B111
A206
2
1
111-250R
B111
A250
2
1

























TABLE 53





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







115-1R
B115
A1
2
1
115-208R
B115
A208
2
1


115-2R
B115
A2
2
1
115-209R
B115
A209
2
1


115-3R
B115
A3
2
1
115-212R
B115
A212
2
1


115-5R
B115
A5
2
1
115-213R
B115
A213
2
1


111-8R
B115
A8
2
1
115-214R
B115
A214
2
1


115-35R
B115
A35
2
1
115-215R
B115
A215
2
1


115-36R
B115
A36
2
1
115-216R
B115
A216
2
1


115-45R
B115
A45
2
1
115-217R
B115
A217
2
1


115-47R
B115
A47
2
1
115-221R
B115
A221
2
1


115-49R
B115
A49
2
1
115-222R
B115
A222
2
1


115-60R
B115
A60
2
1
115-224R
B115
A224
2
1


115-86R
B115
A86
2
1
115-225R
B115
A225
2
1


115-94R
B115
A94
2
1
115-226R
B115
A226
2
1


115-99R
B115
A99
2
1
115-228R
B115
A228
2
1


115-101R
B115
A101
2
1
115-229R
B115
A229
2
1


115-139R
B115
A139
2
1
115-231R
B115
A231
2
1


115-161R
B115
A161
2
1
115-232R
B115
A232
2
1


115-162R
B115
A162
2
1
115-233R
B115
A233
2
1


115-181R
B115
A181
2
1
115-235R
B115
A235
2
1


115-182R
B115
A182
2
1
115-236R
B115
A236
2
1


115-191R
B115
A191
2
1
115-237R
B115
A237
2
1


115-192R
B115
A192
2
1
115-238R
B115
A238
2
1


115-193R
B115
A193
2
1
115-239R
B115
A239
2
1


115-194R
B115
A194
2
1
115-241R
B115
A241
2
1


115-196R
B115
A196
2
1
115-242R
B115
A242
2
1


115-197R
B115
A197
2
1
115-243R
B115
A243
2
1


115-199R
B115
A199
2
1
115-246R
B115
A246
2
1


115-200R
B115
A200
2
1
115-247R
B115
A247
2
1


115-201R
B115
A201
2
1
115-248R
B115
A248
2
1


115-203R
B115
A203
2
1
115-249R
B115
A249
2
1


115-206R
B115
A206
2
1
115-250R
B115
A250
2
1

























TABLE 54





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







201-1R
B201
A1
2
1
201-208R
B201
A208
2
1


201-2R
B201
A2
2
1
201-209R
B201
A209
2
1


201-3R
B201
A3
2
1
201-212R
B201
A212
2
1


201-5R
B201
A5
2
1
201-213R
B201
A213
2
1


201-8R
B201
A8
2
1
201-214R
B201
A214
2
1


201-35R
B201
A35
2
1
201-215R
B201
A215
2
1


201-36R
B201
A36
2
1
201-216R
B201
A216
2
1


201-45R
B201
A45
2
1
201-217R
B201
A217
2
1


201-47R
B201
A47
2
1
201-221R
B201
A221
2
1


201-49R
B201
A49
2
1
201-222R
B201
A222
2
1


201-60R
B201
A60
2
1
201-224R
B201
A224
2
1


201-86R
B201
A86
2
1
201-225R
B201
A225
2
1


201-94R
B201
A94
2
1
201-226R
B201
A226
2
1


201-99R
B201
A99
2
1
201-228R
B201
A228
2
1


201-101R
B201
A101
2
1
201-229R
B201
A229
2
1


201-139R
B201
A139
2
1
201-231R
B201
A231
2
1


201-161R
B201
A161
2
1
201-232R
B201
A232
2
1


201-162R
B201
A162
2
1
201-233R
B201
A233
2
1


201-181R
B201
A181
2
1
201-235R
B201
A235
2
1


201-182R
B201
A182
2
1
201-236R
B201
A236
2
1


201-191R
B201
A191
2
1
201-237R
B201
A237
2
1


201-192R
B201
A192
2
1
201-238R
B201
A238
2
1


201-193R
B201
A193
2
1
201-239R
B201
A239
2
1


201-194R
B201
A194
2
1
201-241R
B201
A241
2
1


201-196R
B201
A196
2
1
201-242R
B201
A242
2
1


201-197R
B201
A197
2
1
201-243R
B201
A243
2
1


201-199R
B201
A199
2
1
201-246R
B201
A246
2
1


201-200R
B201
A200
2
1
201-247R
B201
A247
2
1


201-201R
B201
A201
2
1
201-248R
B201
A248
2
1


201-203R
B201
A203
2
1
201-249R
B201
A249
2
1


201-206R
B201
A206
2
1
201-250R
B201
A250
2
1

























TABLE 55





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







253-1R
B253
A1
2
1
253-208R
B253
A208
2
1


253-2R
B253
A2
2
1
253-209R
B253
A209
2
1


253-3R
B253
A3
2
1
253-212R
B253
A212
2
1


253-5R
B253
A5
2
1
253-213R
B253
A213
2
1


253-8R
B253
A8
2
1
253-214R
B253
A214
2
1


253-35R
B253
A35
2
1
253-215R
B253
A215
2
1


253-36R
B253
A36
2
1
253-216R
B253
A216
2
1


253-45R
B253
A45
2
1
253-217R
B253
A217
2
1


253-47R
B253
A47
2
1
253-221R
B253
A221
2
1


253-49R
B253
A49
2
1
253-222R
B253
A222
2
1


253-60R
B253
A60
2
1
253-224R
B253
A224
2
1


253-86R
B253
A86
2
1
253-225R
B253
A225
2
1


253-94R
B253
A94
2
1
253-226R
B253
A226
2
1


253-99R
B253
A99
2
1
253-228R
B253
A228
2
1


253-101R
B253
A101
2
1
253-229R
B253
A229
2
1


253-139R
B253
A139
2
1
253-231R
B253
A231
2
1


253-161R
B253
A161
2
1
253-232R
B253
A232
2
1


253-162R
B253
A162
2
1
253-233R
B253
A233
2
1


253-181R
B253
A181
2
1
253-235R
B253
A235
2
1


253-182R
B253
A182
2
1
253-236R
B253
A236
2
1


253-191R
B253
A191
2
1
253-237R
B253
A237
2
1


253-192R
B253
A192
2
1
253-238R
B253
A238
2
1


253-193R
B253
A193
2
1
253-239R
B253
A239
2
1


253-194R
B253
A194
2
1
253-241R
B253
A241
2
1


253-196R
B253
A196
2
1
253-242R
B253
A242
2
1


253-197R
B253
A197
2
1
253-243R
B253
A243
2
1


253-199R
B253
A199
2
1
253-246R
B253
A246
2
1


253-200R
B253
A200
2
1
253-247R
B253
A247
2
1


253-201R
B253
A201
2
1
253-248R
B253
A248
2
1


253-203R
B253
A203
2
1
253-249R
B253
A249
2
1


253-206R
B253
A206
2
1
253-250R
B253
A250
2
1

























TABLE 56





Compound




Compound






No.
L1
L2
n1
n2
No.
L1
L2
n1
n2







293-1R
B293
A1
2
1
293-208R
B293
A208
2
1


293-2R
B293
A2
2
1
293-209R
B293
A209
2
1


293-3R
B293
A3
2
1
293-212R
B293
A212
2
1


293-5R
B293
A5
2
1
293-213R
B293
A213
2
1


293-8R
B293
A8
2
1
293-214R
B293
A214
2
1


293-35R
B293
A35
2
1
293-215R
B293
A215
2
1


293-36R
B293
A36
2
1
293-216R
B293
A216
2
1


293-45R
B293
A45
2
1
293-217R
B293
A217
2
1


293-47R
B293
A47
2
1
293-221R
B293
A221
2
1


293-49R
B293
A49
2
1
293-222R
B293
A222
2
1


293-60R
B293
A60
2
1
293-224R
B293
A224
2
1


293-86R
B293
A86
2
1
293-225R
B293
A225
2
1


293-94R
B293
A94
2
1
293-226R
B293
A226
2
1


293-99R
B293
A99
2
1
293-228R
B293
A228
2
1


293-101R
B293
A101
2
1
293-229R
B293
A229
2
1


293-139R
B293
A139
2
1
293-231R
B293
A231
2
1


293-161R
B293
A161
2
1
293-232R
B293
A232
2
1


293-162R
B293
A162
2
1
293-233R
B293
A233
2
1


293-181R
B293
A181
2
1
293-235R
B293
A235
2
1


293-182R
B293
A182
2
1
293-236R
B293
A236
2
1


293-191R
B293
A191
2
1
293-237R
B293
A237
2
1


293-192R
B293
A192
2
1
293-238R
B293
A238
2
1


293-193R
B293
A193
2
1
293-239R
B293
A239
2
1


293-194R
B293
A194
2
1
293-241R
B293
A241
2
1


293-196R
B293
A196
2
1
293-242R
B293
A242
2
1


293-197R
B293
A197
2
1
293-243R
B293
A243
2
1


293-199R
B293
A199
2
1
293-246R
B293
A246
2
1


293-200R
B293
A200
2
1
293-247R
B293
A247
2
1


293-201R
B293
A201
2
1
293-248R
B293
A248
2
1


293-203R
B293
A203
2
1
293-249R
B293
A249
2
1


293-206R
B293
A206
2
1
293-250R
B293
A250
2
1









In one or more embodiments, the organometallic compound represented by Formula 1 may emit a red light or a green light, for example, a red light or a green light having a maximum luminescence wavelength of about 500 nanometers (nm) or greater, for example, a maximum luminescence wavelength of about 500 nm to about 750 nm.


For example, the organometallic compound may emit a green light. In one or more embodiments, the organometallic compound may emit a light (for example, a green light) having a maximum emission wavelength of about 515 nm to about 550 nm, or about 520 nm to about 540 nm.


In relation to the organometallic compound represented by Formula 1, L1 is a ligand represented by Formula 2-1, L2 is a ligand represented by Formula 2-2, n1, which is the number of L1, and n2, which is the number of L2, may each independently be 1 or 2. Accordingly, the current efficiency and the lifespan of an electronic device, such as, an organic light-emitting device, including at least one organometallic compound represented by Formula 1, may be improved.


A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, and a triplet (Ti) energy level of some compounds of the organometallic compound represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimization obtained at the B3LYP level, and results thereof are shown in Table 57. The energy levels are expressed in electron volts (eV).












TABLE 57





Compound No.
HOMO (eV)
LUMO (eV)
T1(eV)







 1
−4.850
−1.254
2.536


(Compound 2-201 of Table 1)





 2
−4.813
−1.276
2.526


(Compound 22-1 of Table 8)





 3
−4.833
−1.289
2.536


(Compound 2-1R of Table 43)





 4
−4.879
−1.324
2.497


(Compound 6-215R of Table 45)





 5
−4.816
−1.229
2.533


(Compound 2-212R of Table 43)





 6
−4.784
−1.222
2.613


(Compound 201-2 of Table 31)





 7
−4.779
−1.229
2.486


(Compound 6-2 of Table 4)





 8
−4.826
−1.254
2.495


(Compound 106-206 of Table 25)





 9
−4.748
−1.183
2.484


(Compound 26-208 of Table 10)





10
−4.865
−1.289
2.492


(Compound 111-203 of Table 26)





11
−4.905
−1.359
2.509


(Compound 26-238R of Table 48)





12
−4.772
−1.154
2.530


(Compound 253-212 of Table 35)





13
−4.751
−1.205
2.495


(Compound 67-217 of Table 18)





14
−4.728
−1.196
2.386


(Compound 293-222 of Table 39)







embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image








From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.


Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.


Accordingly, the organometallic compound represented by Formula 1 is suitable for use as a material for an organic layer of organic light-emitting device, for example, a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and the organic layer includes at least one organometallic compound represented by Formula 1.


The organic light-emitting device includes an organic layer containing at least one organometallic compound represented by Formula 1. Accordingly, the organic light-emitting device may have improved external quantum efficiency and improved lifespan characteristics.


The organometallic compound of Formula 1 may be used or located between a pair of electrodes of an organic light-emitting device. For example, at least one organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the at least one organometallic compound represented by Formula 1 in the emission layer is less than an amount of the host in the emission layer). In other words, in one or more embodiments, an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound represented by Formula 1 in the emission layer, based on the total weight of the emission layer.


The emission layer may emit a red or a green light, for example, a red light or a green light having a maximum luminescence wavelength of about 500 nanometers (nm) or greater, for example, a maximum luminescence wavelength of about 500 nm to about 750 nm. For example, the organometallic compound may emit a green light. In one or more embodiments, the emission layer (or an organic light-emitting device) may emit a light (for example, a green light) having a maximum emission wavelength of about 515 nm to about 550 nm, or about 520 nm to about 540 nm.


The expression “(an organic layer) includes at least one organometallic compound represented by Formula 1” used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1, and a case in which “(an organic layer) includes two or more different organometallic compounds each represented by Formula 1.


For example, the organic layer may include, as the at least one organometallic compound represented by Formula 1, only Compound 1. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the at least one organometallic compound represented by Formula 1, Compound 1 and Compound 2, wherein Compound 1 and Compound 2 are different. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).


The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.


In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer, and an electron transport region located between the emission layer and the second electrode, and the hole transport region may include a hole injection layer, a hole transport layer, an electron-blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.


The term “organic layer” as used herein refers to a single layer and/or a plurality of layers located between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including a metal.


The FIG. 1s a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments will be described in further detail in connection with the FIGURE, but embodiments are not limited thereto. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.


A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water repellency.


The first electrode 11 may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).


The first electrode 11 may have a single-layered structure or the first electrode 11 may have a multi-layered structure including a plurality of layers. For example, in one or more embodiments, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO.


The organic layer 15 may be located on the first electrode 11.


The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.


The hole transport region may be located between the first electrode 11 and the emission layer.


The hole transport region may include a hole injection layer, a hole transport layer, an electron-blocking layer, a buffer layer, or a combination thereof.


The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron-blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.


When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.


When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec.


When the hole injection layer is formed by spin coating, the coating conditions may vary depending on a material for forming the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and heat treatment at about 80° C. to about 200° C. to remove solvent(s) after coating.


The conditions for forming the hole transport layer and the electron-blocking layer may be similar to or the same as the conditions for forming the hole injection layer.


The hole transport region may include at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof, but embodiments are not limited thereto:




embedded image


embedded image


embedded image


embedded image


embedded image


Ar101 and Ar102 in Formula 201 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C1-C60 aryloxy group, a C1-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.


xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.


R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:

    • hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or the like), a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like), or a C1-C10 alkylthio group;
    • a C1-C10 alkyl group, a C1-C10 alkoxy group, or a C1-C10 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof; or
    • a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, or a combination thereof.


R109 in Formula 201 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.


In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A:




embedded image


R101, R111, R112, and R109 in Formula 201A are each as described herein.


For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one of Compounds HT1 to HT20, but embodiments are not limited thereto:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


A thickness of the hole transport region may be about 100 angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. Without wishing to be bound to theory, when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.


The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.


The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant include a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), or the like; a metal oxide, such as a tungsten oxide, a molybdenum oxide, or the like; or a cyano group-containing compound, such as Compound HT-D1, but embodiments are not limited thereto.




embedded image


The hole transport region may include a buffer layer.


Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of a light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.


Meanwhile, when the hole transport region includes an electron-blocking layer, a material for forming the electron-blocking layer may include a material that is used in the hole transport region as described herein, a host material as described herein, or a combination thereof. For example, when the hole transport region includes an electron-blocking layer, mCP, Compound H-H1, or the like, which will be described herein, may be used as a material for the electron-blocking layer, but embodiments are not limited thereto.


An emission layer may be formed on the hole transport region, for example, by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, although the deposition or coating conditions may vary according to a material that is used to form the emission layer.


The emission layer may include a host and a dopant, and the dopant may include at least one organometallic compound represented by Formula 1.


The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalen-2-yl)anthracene (ADN) (also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-E43, or a combination thereof, but embodiments are not limited thereto:




embedded image


embedded image


embedded image


embedded image


When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit a white light.


When the emission layer includes both a host and a dopant, an amount (for example, a weight) of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the emission layer.


A thickness of the emission layer may be about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. Without wishing to be bound to theory, when the thickness of the emission layer is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.


Next, an electron transport region may be located on the emission layer.


The electron transport region may include a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.


For example, the electron transport region may have a hole-blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.


Conditions for forming the hole-blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood, for example, by referring to the conditions for forming the hole injection layer.


When the electron transport region includes a hole-blocking layer, the hole-blocking layer may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), or a combination thereof, but embodiments are not limited thereto:




embedded image


A thickness of the hole-blocking layer may be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. Without wishing to be bound to theory, when the thickness of the hole-blocking layer is within these ranges, excellent hole-blocking characteristics may be obtained without a substantial increase in driving voltage.


In one or more embodiments, the electron transport layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxy-quinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAIq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or a combination thereof.




embedded image


In one or more embodiments, the electron transport layer may include one of Compounds ET1 to ET25, or a combination thereof, but embodiments are not limited thereto:




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


A thickness of the electron transport layer may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Without wishing to be bound to theory, when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.


The electron transport layer may include a metal-containing material in addition to the materials as described herein.


The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2, but embodiments are not limited thereto:




embedded image


The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 into the electron transport region.


The electron injection layer may include, for example, LiF, NaCl, CsF, Li2O, BaO, or a combination thereof, but embodiments are not limited thereto.


A thickness of the electron injection layer may be about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. Without wishing to be bound to theory, when the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.


The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. Examples of the material for forming the second electrode 19 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.


Hereinbefore, the organic light-emitting device has been described in detail and with reference to the FIGURE, but embodiments are not limited thereto.


According to another aspect, the organic light-emitting device may be included in an electronic apparatus. Thus, an electronic apparatus including the organic light-emitting device is also provided. The electronic apparatus may include, for example, a display, an illumination, a sensor, or the like, but embodiments are not limited thereto.


Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.


The organometallic compound represented by Formula 1 provides a high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have a high diagnostic efficiency.


The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, or the like, but embodiments are not limited thereto.


The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.


Non-limiting examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or the like, each unsubstituted or substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or a combination thereof.


The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like.


The term “C1-C60 alkylthio group” as used herein refers to a monovalent group represented by —SA102 (wherein A102 is the C1-C60 alkyl group).


The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, a butenyl group, or the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.


The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethynyl group, a propynyl group, or the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.


The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.


Non-limiting examples of the C3-C10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl, cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.


The term “C1-C10“heterocycloalkyl group” as used herein refers to a saturated cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 10 carbon atoms. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.


Non-limiting examples of the C1-C10 heterocycloalkyl group include a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, or the like.


The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, or the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.


The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring.


Non-limiting examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.


The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.


The term “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group. The term “C7-C60 aryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C6-C60 aryl group.


The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group that includes a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group that includes a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.


The term “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group. The term “C2-C60 heteroaryl alkyl group” as used herein refers to a C1-C60 alkyl group substituted with at least one C1-C60 heteroaryl group.


The term “C6-C60 aryloxy group” as used herein indicates —OA103 (wherein A103 indicates the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein indicates —SA104 (wherein A104 indicates the C6-C60 aryl group).


The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group or the like. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.


The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described herein.


The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Non-limiting examples of the C5-C30 carbocyclic group (unsubstituted or substituted with at least one R10a) as used herein include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, and a fluorene group (each unsubstituted or substituted with at least one R10a).


The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Non-limiting examples of the C1-C30 heterocyclic group (unsubstituted or substituted with at least one R10a) may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, or the like (each unsubstituted or substituted with at least one R10a).


Non-limiting examples of the “C5-C30 carbocyclic group” and the “C1-C30 heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring system in which two or more first rings are condensed with each other, iv) a condensed ring system in which two or more second rings are condensed with each other, or v) a condensed ring system in which at least one first ring is condensed with at least one second ring,

    • the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and
    • 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” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). For example, the term “fluorinated C1 alkyl group” (that is, a fluorinated methyl group) includes —CF3, —CF2H, and —CFH2. The “fluorinated C1-C60 alkyl group” (or, a fluorinated C1-C20 alkyl group, or the like), the “fluorinated C3-C10 cycloalkyl group,” the “fluorinated C1-C10 heterocycloalkyl group,” and the “the fluorinated phenyl group” may respectively be i) a fully fluorinated C1-C60 alkyl group (or, a fully fluorinated C1-C20 alkyl group, or the like), a fully fluorinated C3-C10 cycloalkyl group, a fully fluorinated C1-C10 heterocycloalkyl group, or a fully fluorinated phenyl group, wherein, in each group, all hydrogen atoms included therein are substituted with a fluoro group, or ii) a partially fluorinated C1-C60 alkyl group (or, a partially fluorinated C1-C20 alkyl group, or the like), a partially fluorinated C3-C10 cycloalkyl group, a partially fluorinated C1-C10 heterocycloalkyl group, or partially fluorinated phenyl group, wherein, in each group, all hydrogen atoms included therein are not substituted with a fluoro group.


The terms “deuterated C1-C60 alkyl group” (or a deuterated C1-C20 alkyl group, or the like), “deuterated C3-C10 cycloalkyl group,” “deuterated C1-C10 heterocycloalkyl group,” and “deuterated phenyl group” respectively indicate a C1-C60 alkyl group (or a C1-C20 alkyl group or the like), a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. For example, the “deuterated C1 alkyl group” (that is, the deuterated methyl group) may include —CD3, —CD2H, and —CDH2, and examples of the “deuterated C3-C10 cycloalkyl group” include, for example, Formulae 10-501, 10-502, 10-503, 10-504, or the like. The “deuterated C1-C60 alkyl group” (or, the deuterated C1-C20 alkyl group, or the like), “the “deuterated C3-C10 cycloalkyl group,” “the “deuterated C1-C10 heterocycloalkyl group,” and “the deuterated phenyl group” may respectively be i) a fully deuterated C1-C60 alkyl group (or, a fully deuterated C1-C20 alkyl group, or the like), a fully deuterated C3-C10 cycloalkyl group, a fully deuterated C1-C10 heterocycloalkyl group, or a fully deuterated phenyl group, in which, in each group, all hydrogen atoms included therein are substituted with deuterium, or ii) a partially deuterated C1-C60 alkyl group (or, a partially deuterated C1-C20 alkyl group or the like), a partially deuterated C3-C10 cycloalkyl group, a partially deuterated C1-C10 heterocycloalkyl group, or a partially deuterated phenyl group, in which, in each group, all hydrogen atoms included therein are not substituted with deuterium.


The term “(C1-C20 alkyl)‘X’ group” as used herein refers to a ‘X’ group that is substituted with at least one C1-C20 alkyl group. For example, the term “(C1-C20 alkyl)C3-C10 cycloalkyl group” as used herein refers to a C3-C10 cycloalkyl group substituted with at least one C1-C20 alkyl group, and the term “(C1-C20 alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C1-C20 alkyl group. An example of a (C1 alkyl)phenyl group may include a toluyl group.


As used herein, the terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” each refers to a hetero ring group respectively having an identical backbone as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzothiophene 5,5-dioxide group, in which, in each group, at least one ring-forming carbon atom is substituted with N.”


As used herein, at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C1-C60 aryloxy group, the substituted C1-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

    • deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group;
    • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C1-C60 aryl group, a C7-C60 alkyl aryl group, a C1-C60 aryloxy group, a C1-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
    • a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C1-C60 alkylthio group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
    • N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
    • a combination thereof,
    • wherein Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 as used herein may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.


For example, Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 as described herein may each independently be:

    • —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2, or
    • an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, a C1-C10 alkyl group, a phenyl group, or a combination thereof.


Hereinafter, a compound and an organic light-emitting device according to exemplary embodiments are described in further detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.


EXAMPLES
Synthesis Example
Synthesis Example 1 (Compound 1)



embedded image


Synthesis of Compound A201(1)

Compound A201 (2-phenylpyridine) (7.0 grams (g), 45.1 millimoles (mmol)) and iridium chloride trihydrate (IrCl3(H2O)n, n=3) (7.63 g, 21.6 mmol) were mixed with 120 milliliters (mL) of ethoxyethanol and 40 mL of deionized (DI) water, and then, the resultant mixture was stirred and heated under reflux for 24 hours. Then, the temperature was allowed to lower to room temperature. The resultant solid was separated from the reaction mixture by filtration, washed sufficiently with DI water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 8.75 g (yield of 75%) of Compound A201(1).


Synthesis of Compound A201(2)

Compound A201(1) (3.00 g, 2.80 mmol) and 60 mL of methylene chloride (MC) were mixed together, and then, a separate mixture including silver trifluoromethanesulfonate (AgOTf) (1.51 g, 5.88 mmol) and 20 mL of methanol (MeOH) was added thereto. Afterwards, the resultant mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then the reaction mixture was filtered through a Celite plug to remove the resulting solid. The solvent was removed from the filtrate under a reduced pressure to obtain a solid (Compound A201(2)). Compound A201(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 1

40 mL of ethanol was mixed with Compound A201(2) (3.24 g, 4.54 mmol) and Compound B2 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine) (1.966 g, 4.54 mmol), and then, the reaction mixture was stirred and heated at 90° C. under reflux for 24 hours, and then, the temperature was allowed to lower to room temperature. The resulting solid product was separated by filtration, and purified by column chromatography using EA (ethyl acetate):hexane (1:1 by volume) as eluents to obtain 1.46 g (yield of 34%) of Compound 1. Compound 1 was characterized by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.


HRMS (MALDI) calculated for C46H43GeIrN4O: m/z 934.2278 grams per mole (g/mol), found: 934.2277 g/mol.


Synthesis Example 2 (Compound 2)



embedded image


embedded image


Synthesis of Compound A1(1)

Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine) (7.5 g, 33.1 mmol) and iridium chloride trihydrate (IrCl3(H2O)n) (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of DI water. The reaction mixture was stirred and heated under reflux for 24 hours, and then the temperature was allowed to lower to room temperature. The resultant solid was separated therefrom by filtration, washed sufficiently with DI water, methanol, and hexane, in this stated order, and then dried in a vacuum oven, to obtain 8.2 g (yield of 82%) of Compound A1(1).


Synthesis of Compound A1(2)

Compound A1(1) (1.60 g, 1.18 mmol) and 45 mL of MC were mixed, and then, a separate mixture including AgOTf (0.61 g, 2.35 mmol) and 15 mL of methanol were added thereto. Afterwards, the reaction mixture was stirred for 18 hours at room temperature while light was blocked with aluminum foil, and then filtered through a plug of Celite to remove the resulting solid. The solvent was removed from the filtrate under a reduced pressure to obtain a solid (Compound A1(2)). Compound A1(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 2

30 mL of ethanol was mixed with Compound A1(2) (1.610 g, 1.88 mmol) and Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) (0.818 g, 1.88 mmol), and then, the reaction mixture was stirred and heated under reflux at a temperature of 90° C. for 24 hours. Then, the temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, and the product was purified by column chromatography using EA:hexane (1:1 v/v) as eluents to obtain 0.71 g (yield of 35%) of Compound 2.


HRMS (MALDI) calculated for C52H56D3GeIrN4OSi2: m/z 1081.3257 g/mol, found: 1081.3256 g/mol.


Synthesis Example 3 (Compound 3)



embedded image


Synthesis of Compound B2(1)

12.1 g (yield of 71%) of Compound B2(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B2 (8-(4-isobutyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound B2(2)

Compound B2(2) was obtained in a similar manner as used to obtain Compound A1(2) in Synthesis Example 2, except that Compound B2(1) was used instead of Compound A1(1). The obtained Compound B2(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 3

Compound B2(2) (3.52 g, 2.78 mmol) and Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine) (0.631 g, 2.78 mmol) were mixed with 25 mL of 2-ethoxyethanol and 25 mL of N,N-dimethylformamide, and then, the reaction mixture was stirred and heated under reflux at a temperature of 130° C. for 48 hours. Then, the temperature was allowed to lower to room temperature. The solvent was removed from the resulting mixture under a reduced pressure to obtain a solid, and the solid was purified by column chromatography using EA:hexane (1:1 v/v) as eluents to obtain 1.18 g (yield of 33%) of Compound 3.


HRMS (MALDI) calculated for C62H70Ge2IrN5O2Si: m/z 1285.3352 g/mol, found: 1285.3351 g/mol.


Synthesis Example 4 (Compound 4)



embedded image


Synthesis of Compound B6(1)

11.6 g (yield of 74%) of Compound B6(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B6 (2-methyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (12.5 g, 33.15 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound B6(2)

Compound B6(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound B6(1) was used instead of Compound A1(1). The obtained Compound B6(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 4

1.10 g (yield of 36%) of Compound 4 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound B6(2) (3.20 g, 2.77 mmol) was used instead of compound B2(2), and Compound A215 (4-(methyl-d3)-2-phenylpyridine) (0.477 g, 2.77 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


HRMS (MALDI) calculated for C52H45D3Ge2IrN5O2: m/z 1118.2049 g/mol, found: 1118.2047 g/mol.


Synthesis Example 5 (Compound 5)



embedded image


0.98 g (yield of 31%) of Compound 5 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound A212 (4-isobutyl-2-phenylpyridine) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


HRMS (MALDI) calculated for C63H70Ge2IrN5O2: m/z 1269.3582 g/mol, found: 1269.3583 g/mol.


Synthesis Example 6 (Compound 6)



embedded image


Synthesis of Compound A2(1)

7.94 g (yield of 74%) of Compound A2(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A2 (4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine) (8.00 g, 28.22 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A2(2)

Compound A2(2) was obtained in a similar manner as was used to obtain Compound A1 (2) in Synthesis Example 2, except that Compound A2(1) was used instead of Compound A1(1). The obtained Compound A2(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 6

1.35 g (yield of 37%) of Compound 6 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A2(2) (3.15 g, 3.25 mmol) was used instead of Compound A1(2), and Compound B201 (6-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (3.25 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C55H65GeIrN4OSi2: m/z 1120.3538 g/mol, found: 1120.3536 g/mol.


Synthesis Example 7 (Compound 7)



embedded image


1.49 g (yield of 40%) of Compound 7 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A2(2) (3.18 g, 3.28 mmol) was used instead of Compound A1(2), and Compound B6 (2-methyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.236 g, 3.28 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C56H67GeIrN4OSi2: m/z 1134.3694 g/mol, found: 1134.3694 g/mol.


Synthesis Example 8 (Compound 8)



embedded image


embedded image


Synthesis of Compound A206(1)

6.50 g (yield of 82%) of Compound A206 (1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A206 (5-(methyl-d3)-2-phenylpyridine) (5.00 g, 29.03 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A206(2)

Compound A206(2) was obtained in a similar manner as used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A206(1) was used instead of Compound A1(1). The obtained Compound A206(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 8

1.32 g (yield of 35%) of Compound 8 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A206(2) (3.00 g, 4.01 mmol) was used instead of Compound A1(2), and Compound B106 (2-isopropyl-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.625 g, 4.01 mmol) was used instead of Compound B22(8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C46H37D6GeIrN4O: m/z 940.2654 g/mol, found: 940.2656 g/mol.


Synthesis Example 9 (Compound 9)



embedded image


embedded image


Synthesis of Compound A208(1)

6.82 g (yield of 77%) of Compound A208(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A208 (4-isopropyl-5-methyl-2-phenylpyridine) (6.00 g, 28.39 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A208(2)

Compound A208(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A208(1) was used instead of Compound A(1). The obtained Compound A208(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 9

1.38 g (yield of 35%) of Compound 9 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A208(2) (3.25 g, 3.93 mmol) was used instead of Compound A1(2), and Compound B26 (2-(methyl-d3)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.495 g, 3.93 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C50H48D3GeIrN4O: m/z: 993.3092 g/mol, found: 993.3091 g/mol.


Synthesis Example 10 (Compound 10)



embedded image


embedded image


Synthesis of Compound A203(1)

6.67 g (yield of 74%) of Compound A203(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A203 (5-isopropyl-2-phenylpyridine) (6.00 g, 30.41 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A203(2)

Compound A203(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A203(1) was used instead of Compound A1(1). The obtained Compound A203(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 10

1.25 g (yield of 32%) of Compound 10 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A203(2) (3.00 g, 3.76 mmol) was used instead of Compound A1(2), and Compound B111 (2-(2,6-dimethylphenyl)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (1.756 g, 3.76 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C55H53GeIrN4O: m/z: 1052.30604 g/mol, found: 1052.30604 g/mol.


Synthesis Example 11 (Compound 11)



embedded image


Synthesis of Compound B26(1)

4.87 g (yield of 78%) of Compound B26(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound B26 (2-(methyl-d3)-8-(5-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-b]pyridine) (5 g, 13.16 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound B26(2)

Compound B26(2) was obtained in a similar manner as was used to obtain Compound B2(2) in Synthesis Example 3, except that Compound B26(1) was used instead of Compound B2(1). The obtained Compound B26(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 11

1.12 g (yield of 35%) of Compound 11 was obtained in a similar manner as was used to obtain Compound 3 in Synthesis Example 3, except that Compound B26(2) (3.00 g, 2.58 mmol) was used instead of Compound B2(2), and Compound A238 (4-(tert-butyl)-2-(dibenzo[b,d]furan-4-yl)pyridine) (0.779 g, 2.58 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


HRMS (MALDI) calculated for C61H50D6Ge2IrN5O3: m/z: 1253.2813 g/mol, found: 1253.2815 g/mol.


Synthesis Example 12 (Compound 12)



embedded image


Synthesis of Compound A212(1)

5.62 g (yield of 76%) of Compound A212(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A212 (4-isobutyl-2-phenylpyridine) (5 g, 23.66 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A212(2)

Compound A212(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A212(1) was used instead of Compound A1(1). The obtained Compound A212(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 12

1.35 g (yield of 35%) of Compound 12 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A212(2) (3.00 g, 3.63 mmol) was used instead of Compound A1(2), and Compound B253 (2-(methyl-d3)-8-(4-isopropyl-5-(trimethylgermyl)pyridin-2-yl)benzothieno[2,3-b]pyridine) (1.59 g, 3.63 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C53H54D3GeIrN4S: m/z: 1051.3333 g/mol, found: 1051.3334 g/mol.


Synthesis Example 13 (Compound 13)



embedded image


Synthesis of Compound A217(1)

5.73 g (yield of 82%) of Compound A217(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A217 (4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridin) (5 g, 19.13 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A217(2)

Compound A217(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A217(1) was used instead of Compound A1(1). The obtained Compound A217(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 13

1.44 g (yield of 34%) of Compound 13 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A217(2) (3.50 g, 3.78 mmol) was used instead of Compound A1(2) and Compound B67 (1,3-bis(methyl-d3)-8-(5-(methyl-d3)-4-(trimethylgermyl)pyridin-2-yl)benzofuro[2,3-c]pyridine) (1.57 g, 3.78 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C58H42D25GeIrN4O: m/z: 1127.5725 g/mol, found: 1127.5727 g/mol.


Synthesis Example 14 (Compound 14)



embedded image


Synthesis of Compound A222(1)

5.58 g (yield of 81%) of Compound A222(1) was obtained in a similar manner as was used to obtain Compound A1(1) in Synthesis Example 2, except that Compound A222 (5-(tert-butyl)-2-phenyl-4-(propan-2-yl-2-d)pyridine) (5 g, 19.65 mmol) was used instead of Compound A1 (2-phenyl-5-(trimethylsilyl)pyridine).


Synthesis of Compound A222(2)

Compound A222(2) was obtained in a similar manner as was used to obtain Compound A1(2) in Synthesis Example 2, except that Compound A222(1) was used instead of Compound A1(1). The obtained Compound A222(2) was used in the next reaction step without an additional purification process.


Synthesis of Compound 14

1.35 g (yield of 31%) of Compound 14 was obtained in a similar manner as was used to obtain Compound 2 in Synthesis Example 2, except that Compound A222(2) (3.43 g, 3.76 mmol) was used instead of Compound A1 (2), and Compound B293 (9-(4-isopropyl-5-(trimethylgermyl)pyridin-2-yl)-2-methylbenzofuro[3,2-g]quinoline) (1.76 g, 3.76 mmol) was used instead of Compound B22 (8-(4-isobutyl-5-(trimethylgermyl)pyridine-2-nyl)-2-(methyl-d3)benzofuro[2,3-b]pyridine).


HRMS (MALDI) calculated for C63H69D2GeIrN4O: m/z: 1168.4594 g/mol, found: 1168.4595 g/mol.


Example 1

A glass substrate with ITO/Ag/ITO (as an anode) deposited thereon to a thickness of 70/1000/70 Å was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes each. Then, the resultant glass substrate was loaded onto a vacuum deposition apparatus.


Compound HT3 and Compound F6-TCNNQ were vacuum-deposited on the anode at the weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and, on the hole injection layer, Compound HT3 was vacuum-deposited to form a hole transport layer having a thickness of 1350 Å. Then, Compound H-H1 was deposited on the hole transport layer to form an electron-blocking layer having a thickness of 300 Å.


Then, Compound H-H1, Compound H-E43, and Compound 1 (dopant) were co-deposited on the electron-blocking layer at a weight ratio of 57:38:5 to form an emission layer having a thickness of 400 Å.


Then, Compound ET3 and Compound ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form an electron transport layer with a thickness of 350 Å, and LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and both Mg and Ag were co-deposited at a weight ratio of 90:10 on the electron injection layer to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device.




embedded image


embedded image


Examples 2 to 4 and Comparative Examples R1 to R4

Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 58 were each used instead of Compound 1 as a dopant when forming the emission layer.


Evaluation Example 1

The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples R1 to R4. Results thereof are shown in Table 58. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifespan (T97) (at 15,000 candela per square meter (cd/m2)) was evaluated as the time (hr) taken for luminance to reduce to 97% from 100% of the initial luminance. Each of the maximum current efficiency and lifespan was expressed as a relative value (%).


Meanwhile, Compound H-H1, Compound H-E43 and Compound 1 were co-deposited on a quartz substrate at a weight ratio of 57:38:5 to produce a film with a thickness of 40 nm, and then the emission spectrum of the film was measured by using the Quantaurus-QY absolute PL quantum yield spectrometer (on which a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere (011347-12) are mounted and which includes PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka) manufactured by Hamamatsu Inc.). At the time of measurement, the excitation wavelength was measured by scanning from 320 nm to 380 nm at intervals of 10 nm, and a spectrum measured at the excitation wavelength of 340 nm was used to evaluate the emission peak wavelength of Compound 1 in Table 58.


The emission peak wavelength evaluation was similarly performed for the remaining compounds shown in Table 58, and the results are shown in Table 58.













TABLE 58









Emission




Maximum

peak



Dopant in emission
current

wave-



layer
efficiency
LT97
length



Compound No.
(relative %)
(relative %)
(nm)



















Example 1
1
93
69
525


Comparative
R1
91
62
528


Example R1






Example 2
2
100
94
528


Comparative
R2
97
80
530


Example R2






Example 3
3
91
93
534


Comparative
R3
68
48
539


Example R3






Example 4
4
97
100
532


Comparative
R4
81
67
536


Example R4







embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image








From Table 58, it was confirmed that each of the organic light-emitting devices of Examples 1 to 4 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting devices of Comparative Examples R1 to R4.


Example 5 and Comparative Example R5

Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 59 were used instead of Compound 1 as a dopant when forming the emission layer.


Evaluation Example 2

The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Example 5 and Comparative Example R5 and the emission peak wavelength of Compound 5 and Compound R5 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 59.













TABLE 59






Dopant in






emission






layer
Maximum current

Emission peak



Compound
efficiency
LT97
wavelength



No.
(relative %)
(relative %)
(nm)



















Example 5
5
100
100
527


Comparative
R5
95
66
524


Example R5











embedded image


embedded image








From Table 59, it was confirmed that the organic light-emitting device of Example 5 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R5.


Example 6 and Comparative Example R6

Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 60 were used instead of Compound 1 as a dopant when forming the emission layer.


Evaluation Example 3

The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Example 6 and Comparative Example R6 and the emission peak wavelength of Compound 6 and Compound R6 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 60.













TABLE 60






Dopant
Maximum





in emission
current

Emission peak



layer
efficiency
LT97
wavelength



Compound No.
(relative %)
(relative %)
(nm)



















Example 6
6
100
100
519


Compara-
R6
97
89
520


tive






Example R6











embedded image


embedded image








From Table 60, it was confirmed that the organic light-emitting device of Example 6 emits a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R6.


Examples 7 to 14

Organic light-emitting devices were manufactured using a similar method as was used in Example 1, except that the compounds listed in Table 61 were used instead of Compound 1 as a dopant when forming the emission layer.


Evaluation Example 4

The maximum current efficiency (Max cd/A, %) and lifespan (LT97, %) at target color coordinates CIEx=0.245 were evaluated for each of the organic light-emitting devices manufactured in Examples 7 to 14 and the emission peak wavelength of Compound 7 to Compound 14 were evaluated by using a similar method as Evaluation Example 1. The results are shown in Table 61. For comparison, the data of Comparative Example R1 is also shown in Table 61.













TABLE 61






Dopant in
Maximum

Emission



emission
current
LT97
peak



layer
efficiency
(relative
wavelength



Compound No.
(relative %)
%)
(nm)



















Example 7
7
88
100
531


Example 8
8
81
69
529


Example 9
9
87
80
526


Example 10
10
88
70
528


Example 11
11
88
98
531


Example 12
12
87
81
526


Example 13
13
83
74
526


Example 14
14
100
71
532


Compara-
R1
77
60
528


tive






Example R1











embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


embedded image








From Table 61, it was confirmed that the organic light-emitting devices of Example 7 to 14 emit a green light while having improved maximum current efficiency and improved lifespan characteristics compared to the organic light-emitting device of Comparative Example R1.


Since the organometallic compounds have excellent thermal stability and/or electric characteristics, an electronic device using the organometallic compounds, for example, an organic light-emitting device using one or more of the organometallic compounds can have improved current efficiency and improved lifespan characteristics, and a high-quality electronic apparatus can be manufactured using the organic light-emitting device.


It should be understood that exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other embodiments.


While one or more exemplary embodiments have been described with reference to the FIGURE, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims
  • 1. An organometallic compound represented by Formula 1: M(L1)n1(L2)n2  Formula 1wherein, in Formula 1, M is a transition metal,L1 is a ligand represented by Formula 2-1,L2 is a ligand represented by Formula 2-2,n1 and n2 are each independently 1 or 2, when n1 is 2, two L1 are identical to or different from each other, and when n2 is 2, two L2 are identical to or different from each other, andL1 and L2 are different from each other,
  • 2. The organometallic compound of claim 1, wherein X2 is O or S.
  • 3. The organometallic compound of claim 1, wherein, in Formula 2-1, A1 is C bonded to a neighboring pyridine group, and A2 is C bonded to M in Formula 1, orA3 is C bonded to a neighboring pyridine group, and A2 is C bonded to M in Formula 1.
  • 4. The organometallic compound of claim 1, wherein ring CY2 is a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthridine group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, or an azadibenzoselenophene group.
  • 5. The organometallic compound of claim 1, wherein ring CY4 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group that is condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a naphthobenzothiophene group, a naphthobenzofuran group, a naphthobenzoselenophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, a dinaphthothiophene group, a dinaphthofuran group, a dinaphthoselenophene group, a naphthocarbazole group, a naphthofluorene group, a phenanthrobenzosilole group, a phenanthrobenzothiophene group, a phenanthrobenzofuran group, a phenanthrobenzoselenophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azadibenzoselenophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azanaphthobenzothiophene group, an azanaphthobenzofuran group, an azanaphthobenzoselenophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, an azadinaphthothiophene group, an azadinaphthofuran group, an azadinaphthoselenophene group, an azanaphthocarbazole group, an azanaphthofluorene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzofuran group, or an azaphenanthrobenzoselenophene group.
  • 6. The organometallic compound of claim 1, wherein R1 to R4, R29, R29a, and R29b are each independently: hydrogen, deuterium, —F, or a cyano group;a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), or a combination thereof; orSi(Q3)(Q4)(Q5), andR14 to R16 are each independently a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a fluorinated C3-C10cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.
  • 7. The organometallic compound of claim 1, wherein, in Formula 2-1, a2 is not 0, and R2 is not hydrogen.
  • 8. The organometallic compound of claim 1, wherein, in Formula 2-2, a3 is not 0, and R3 is not hydrogen.
  • 9. The organometallic compound of claim 1, wherein the organometallic compound comprises deuterium, a fluoro group, or a combination thereof.
  • 10. The organometallic compound of claim 1, wherein a group represented by
  • 11. The organometallic compound of claim 1, wherein a group represented by
  • 12. The organometallic compound of claim 11, wherein at least one of A4 to A8 in Formula CY2-1 is N,at least one of A4 to A10 in Formulae CY2-2 to CY2-4 is N, andat least one of A4 to A12 in Formulae CY2-5 to CY2-14 is N.
  • 13. The organometallic compound of claim 1, wherein a group represented by
  • 14. The organometallic compound of claim 1, wherein a group represented by
  • 15. An organic light-emitting device, comprising: a first electrode;a second electrode; andan organic layer located between the first electrode and the second electrode,wherein the organic layer comprises an emission layer, andwherein the organic layer comprises at least one organometallic compound of claim 1.
  • 16. The organic light-emitting device of claim 15, wherein the first electrode is an anode,the second electrode is a cathode, andthe organic layer further comprises 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,wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron-blocking layer, a buffer layer, or a combination thereof, andthe electron transport region comprises a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
  • 17. The organic light-emitting device of claim 15, wherein the emission layer comprises the at least one organometallic compound.
  • 18. The organic light-emitting device of claim 17, wherein the emission layer emits a green light.
  • 19. The organic light-emitting device of claim 17, wherein the emission layer further comprises a host, and the amount of the host in the emission layer is greater than the amount of the organometallic compound in the emission layer.
  • 20. An electronic apparatus, comprising the organic light-emitting device of claim 15.
Priority Claims (1)
Number Date Country Kind
10-2022-0065551 May 2022 KR national