WO2020209679A1 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2020209679A1
WO2020209679A1 PCT/KR2020/004926 KR2020004926W WO2020209679A1 WO 2020209679 A1 WO2020209679 A1 WO 2020209679A1 KR 2020004926 W KR2020004926 W KR 2020004926W WO 2020209679 A1 WO2020209679 A1 WO 2020209679A1
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김충한
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두산솔루스 주식회사
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more particularly, a novel pyrimidine derivative compound having excellent electron injection and transport capabilities, and the luminous efficiency and driving voltage by including the same in one or more organic material layers. , It relates to an organic electroluminescent device having improved characteristics such as lifetime.
  • An organic electroluminescent (EL) device is a self-luminous device using the principle that a fluorescent material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.
  • the material for forming the light-emitting layer of the organic EL device may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials for realizing better natural colors according to light emission colors.
  • a host/dopant system may be used as a light emitting material.
  • the dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB hole injection layer
  • BCP electron transport auxiliary layer
  • Alq 3 and the like anthracene derivatives have been reported as the light emitting layer material.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 are blue and green.
  • Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 are blue and green.
  • CBP 4,4-dicarbazolybiphenyl
  • the present invention can be applied to an organic electroluminescent device, and particularly has an object to provide a novel organic compound excellent in both electron injection and transport capabilities.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, exhibiting a low driving voltage and high luminous efficiency, and improving lifespan.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 to X 3 are each independently N or C (R 1 ), but at least two or more of them are N, and R 1 is hydrogen or a substituted or unsubstituted C 1 to C 60 alkyl,
  • L 1 to L 4 are each independently a direct bond, or selected from the group consisting of an arylene group of C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms,
  • a and B are each independently a substituted or unsubstituted C 6 to C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms, and at least one is a heteroaryl group including a nitrogen-containing heterocycle,
  • Ar 1 and Ar 2 is a C 6 ⁇ C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms, at least one is an aryl group or heteroaryl group substituted with a cyano group,
  • the arylene group and heteroarylene group of L 1 to L 4, the aryl group and heteroaryl group of A, B, Ar 1 and Ar 2 are each independently deuterium, halogen, cyano group, nitro group, C 1 to C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 6 ⁇ C 60 aryloxy group , C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group , C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 mono or diarylphosphine group and
  • Alkyl in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.
  • alkenyl is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds, examples of which are vinyl (vinyl), There are allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
  • alkynyl is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond, and examples thereof are ethynyl , 2-propynyl, and the like, but are not limited thereto.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • two or more rings are condensed with each other, contain only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule is a monovalent having non-aromacity Substituents may also be included.
  • aryl include phenyl, naphthyl, phenanthryl, anthryl, and fluorenyl, but are not limited thereto.
  • heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring may be substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply attached or condensed with each other, and a hetero atom selected from N, O, P, S and Se in addition to carbon as a ring forming atom is included, and the entire molecule is non-aromatic (non-aromatic) aromacity) is interpreted to include monovalent groups.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycylates such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl Click ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, and R means an aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R'means 1 to 40 alkyl, and has a linear, branched, or cyclic structure It is interpreted as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • Arylamine in the present invention means an amine substituted with an aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, Substituted by a hetero atom such as S or Se.
  • heterocycloalkyl include morpholine and piperazine, but are not limited thereto.
  • alkylsilyl refers to silyl substituted with an alkyl having 1 to 40 carbon atoms
  • arylsilyl refers to silyl substituted with an aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound of the present invention Since the compound of the present invention has excellent thermal stability and light emission properties, it can be used as a material for an organic material layer of an organic electroluminescent device.
  • an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long lifespan can be manufactured compared to conventional materials. Furthermore, it is possible to manufacture a full-color display panel with improved performance and lifespan.
  • FIG. 1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • the present invention is a pyrimidine-based/triazine-based organic light-emitting compound, which has excellent luminous efficiency compared to the existing electron injection and transport materials, and has excellent lifespan characteristics of the material, so that the driving life of the device is very excellent, as well as inducing an increase in power efficiency.
  • the compound according to the present invention is represented by the following formula (1).
  • X 1 to X 3 are each independently N or C (R 1 ), but at least two or more of them are N, and R 1 is hydrogen or a substituted or unsubstituted C 1 to C 60 alkyl,
  • L 1 to L 4 are each independently a direct bond, or selected from the group consisting of an arylene group of C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms,
  • a and B are each independently a substituted or unsubstituted C 6 to C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms, and at least one is a heteroaryl group including a nitrogen-containing heterocycle,
  • Ar 1 and Ar 2 is a C 6 ⁇ C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms, at least one is an aryl group or heteroaryl group substituted with a cyano group,
  • the arylene group and heteroarylene group of L 1 to L 4, the aryl group and heteroaryl group of A, B, Ar 1 and Ar 2 are each independently deuterium, halogen, cyano group, nitro group, C 1 to C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 6 ⁇ C 60 aryloxy group , C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 1 ⁇ C 40 alkylsilyl group , C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 mono or diarylphosphine group and
  • the compound represented by Formula 1 may be represented by Formula 1-1 or 1-2 below.
  • each of A and B is independently selected from the following substituent groups, and at least one or more may be a substituent including a nitrogen-containing heterocycle.
  • Ar 1 and Ar 2 are each independently selected from the following substituent groups, and at least one may be substituted with a cyano group.
  • L 1 to L 4 may each independently be a direct bond or an arylene.
  • the compound may be selected from the group consisting of the following compounds.
  • the compound of the present invention represented by Formula 1 can be synthesized according to a general synthesis method ( Chem. Rev. , 60 :313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457) (1995) et al.). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described later.
  • organic electroluminescent device including the compound represented by Formula 1 according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers It includes a compound represented by Formula 1.
  • the compound may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, of which at least one organic material layer contains the compound represented by Formula 1 above.
  • the electron transport layer, the electron transport auxiliary layer, or the light-emitting layer may include the compound represented by Formula 1 above.
  • the structure of the organic electroluminescent device according to the present invention is not particularly limited, but referring to FIG. 1 as an example, for example, an anode 10 and a cathode 20 facing each other, and the anode 10 and the cathode ( 20) includes an organic layer 30 positioned between.
  • the organic layer 30 may include a hole transport layer 31, an emission layer 32 and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode An electron injection layer 36 may be further included between the 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 not only improves the interfacial characteristics between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • it is a layer that has a function of smoothing the surface of ITO by being applied on the top of the ITO, which is not flat, and can be used without particular limitation, as long as it is commonly used in the art.
  • an amine compound can be used. It is not limited thereto.
  • the electron injection layer 36 is a layer that is stacked on top of the electron transport layer to facilitate electron injection from the cathode and ultimately improves power efficiency, and is a special layer that is commonly used in the art. It can be used without limitation, and materials such as LiF, Liq, NaCl, CsF, Li 2 O, and BaO may be used.
  • an electron transport auxiliary layer 35 may be further included between the electron transport layer 34 and the emission layer 32. Holes moving along the ionization potential level in the organic light-emitting device to the emission layer 32 are blocked by the high energy barrier of the electron transport auxiliary layer 35 and cannot diffuse or move to the electron transport layer, and as a result, holes are transferred to the emission layer. It serves as a limiting function. This function of restricting holes to the emission layer prevents the diffusion of holes to the electron transport layer that moves electrons by reduction, suppressing the reduction in lifespan through irreversible decomposition reactions caused by oxidation, and contributing to the improvement of the lifespan of the organic light emitting device. I can.
  • the compound represented by Chemical Formula 1 forms a basic skeleton by condensing an indene moiety and another indene moiety, which has a high efficiency effect in an electronic material.
  • an electron attractor (EWG) with high electron absorption such as a nitrogen-containing heterocycle (e.g., a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, the entire molecule has a bipolar property. It can increase the bonding power of electrons and electrons
  • the compound represented by Chemical Formula 1 has steric hindrance by spiro-type cyclohexyl. Accordingly, it has a high triplet energy, and excitons generated in the light-emitting layer can be prevented from being diffused into an electron transport layer or a hole transport layer adjacent to the light-emitting layer. The number of excitons contributing to light emission in the light emitting layer is increased, so that the luminous efficiency of the device can be improved, durability and stability of the device are improved, so that the life of the device can be efficiently increased.
  • spiro-type cyclohexyl described above has excellent thermal stability due to structural characteristics compared to conventional dimethyl or diphenyl. This makes it possible to compensate for the shortcomings of existing materials, and it is easy to synthesize long-lived materials.
  • the compound represented by Formula 1 is electrochemically stable, has excellent electron mobility, high glass transition temperature and thermal stability, and has physicochemical properties more suitable for an electron transport layer.
  • the compound represented by Chemical Formula 1 of the present invention may be used as a material for the organic material layer 30, preferably the electron transport layer 34 and the electron transport auxiliary layer 35 of the organic electroluminescent device.
  • the organic electroluminescent device including the compound of Formula 1 may have significantly improved performance and lifetime characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied may also maximize performance.
  • the organic electroluminescent device may include an anode, one or more organic material layers, and a cathode sequentially stacked as described above, and further include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (eg, an electron transport layer) is formed to include the compound represented by Formula 1 It can be manufactured by forming other organic material layers and electrodes.
  • the organic material layers eg, an electron transport layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, and the like may be used.
  • the anode material may be made of a conductor having a high work function to facilitate hole injection, for example, and may include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or S
  • a negative electrode material for example, it may be made of a conductor having a low work function to facilitate electron injection, and magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead The same metal or alloys thereof; And a multilayered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • Target compound 26g by performing the same procedure as in [Preparation Example 1], except that 4-(3,5-dibromophenyl)-2-(4-isocyanophenyl)-6-(naphthalen-2-yl)pyrimidine was used as a reactant Got HRMS [M]+: 539.08
  • the target compound 26g was obtained by performing the same procedure as in [Preparation Example 1].; HRMS [M]+: 565.09
  • the target compound 26g was obtained by performing the same procedure as in [Preparation Example 2].; HRMS [M]+: 565.09
  • the target compound 26g was obtained by performing the same procedure as in [Preparation Example 5].; HRMS [M]+: 565.09
  • the target compound 26g was obtained by performing the same procedure as in [Preparation Example 6].; HRMS [M]+: 565.09
  • 26g of the target compound was obtained by performing the same procedure as in [Preparation Example 1], except that quinolin-5-ylboronic acid was used as the reactant.; HRMS [M]+: 615.11
  • 26g of the target compound was obtained by performing the same procedure as in [Preparation Example 4], except that quinolin-5-ylboronic acid was used as the reactant.; HRMS [M]+: 616.11
  • 26g of the target compound was obtained by performing the same procedure as in [Preparation Example 7], except that quinolin-5-ylboronic acid was used as the reactant.; HRMS [M]+: 665.13
  • Target compound 26g by performing the same procedure as in [Preparation Example 25], except that 4-(3,5-dibromophenyl)-2-(4-isocyanophenyl)-6-(naphthalen-2-yl)pyrimidine was used as the reactant Got HRMS [M]+: 627.11
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that triphenylen-2-ylboronic acid was used as the reactant.; HRMS [M]+: 713.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that (9,9-dimethyl-9H-fluoren-3-yl)boronic acid was used as the reactant.; HRMS [M]+: 679.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that dibenzo[b,d]furan-2-ylboronic acid was used as the reactant.; HRMS [M]+: 653.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that dibenzo[b,e][1,4]dioxin-2-ylboronic acid was used as the reactant.; HRMS [M]+: 669.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that pyridin-3-ylboronic acid was used as the reactant.; HRMS [M]+: 564.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that 5-(hydroxy(methyl)boranyl)quinoline was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that (1,10-phenanthrolin-2-yl)boronic acid was used as the reactant.; HRMS [M]+: 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that (4-(pyridin-3-yl)phenyl)boronic acid was used as the reactant.; HRMS [M]+: 640.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 2] was used as the reactant.; HRMS [M] + : 663.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 713.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 679.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 728.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 653.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 2] was used as the reactant.; HRMS [M] + : 652.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 669.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 564.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 640.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 2] was used as the reactant.; HRMS [M]+: 679.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 3] was used as the reactant.; HRMS [M] + : 688.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 738.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 704.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 753.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 678.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 3] was used as the reactant.; HRMS [M] + : 677.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 694.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 589.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 639.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 690.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 3] was used as the reactant.; HRMS [M]+: 704.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 4] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 680.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 4] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 666.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 4] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 5] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 680.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 5] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 666.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 5] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 6] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 680.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 6] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 666.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 6] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 7] was used as the reactant.; HRMS [M] + : 713.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 763.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 729.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 778.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 7] was used as the reactant.; HRMS [M] + : 702.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7] except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 719.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 664.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 715.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 690.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 7] was used as the reactant.; HRMS [M]+: 629.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 8] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 680.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 8] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 666.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 8] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 9] was used as the reactant; HRMS [M] + : 663.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 9] was used as the reactant.; HRMS [M]+: 728.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 9] was used as the reactant.; HRMS [M]+: 653.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 9] was used as the reactant; HRMS [M] + : 652.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 9] was used as the reactant.; HRMS [M]+: 564.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 9] was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 10] was used as the reactant.; HRMS [M] + : 663.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 10] was used as the reactant.; HRMS [M]+: 728.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 10] was used as the reactant.; HRMS [M]+: 653.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 10] was used as the reactant.; HRMS [M] + : 652.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 10] was used as the reactant.; HRMS [M]+: 564.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 10] was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 11] was used as the reactant.; HRMS [M] + : 688.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 11] was used as the reactant.; HRMS [M]+: 753.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 11] was used as the reactant.; HRMS [M]+: 678.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 11] was used as the reactant.; HRMS [M] + : 677.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 11] was used as the reactant.; HRMS [M]+: 589.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 11] was used as the reactant.; HRMS [M]+: 639.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 12] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 12] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 12] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 12] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 12] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 12] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 13] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 13] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 13] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 13] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 13] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 13] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 14] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 14] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 14] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 14] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 14] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 14] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 15] was used as the reactant.; HRMS [M] + : 713.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 15] was used as the reactant.; HRMS [M]+: 778.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 15] was used as the reactant.; HRMS [M]+: 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 15] was used as the reactant.; HRMS [M] + : 702.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 15] was used as the reactant.; HRMS [M]+: 614.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 15] was used as the reactant.; HRMS [M]+: 664.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 16] was used as the reactant.; HRMS [M] + : 664.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 16] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 16] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 16] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 16] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 16] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 17] was used as the reactant; HRMS [M] + : 713.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 17] was used as the reactant.; HRMS [M]+: 778.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 17] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 17] was used as the reactant; HRMS [M] + : 702.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 17] was used as the reactant.; HRMS [M]+: 614.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 17] was used as the reactant.; HRMS [M]+: 664.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 18] was used as the reactant.; HRMS [M] + : 723.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 18] was used as the reactant.; HRMS [M]+: 778.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 18] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 18] was used as the reactant.; HRMS [M] + : 702.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 18] was used as the reactant.; HRMS [M]+: 614.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 18] was used as the reactant.; HRMS [M]+: 664.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 19] was used as the reactant.; HRMS [M] + : 738.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 19] was used as the reactant.; HRMS [M]+: 803.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 19] was used as the reactant.; HRMS [M]+: 728.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 19] was used as the reactant.; HRMS [M] + : 727.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 19] was used as the reactant.; HRMS [M]+: 639.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 19] was used as the reactant.; HRMS [M]+: 689.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 20] was used as the reactant.; HRMS [M] + : 714.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 20] was used as the reactant.; HRMS [M]+: 779.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 20] was used as the reactant.; HRMS [M]+: 704.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 20] was used as the reactant.; HRMS [M] + : 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 20] was used as the reactant.; HRMS [M]+: 615.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 20] was used as the reactant.; HRMS [M]+: 665.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 21] was used as the reactant.; HRMS [M] + : 714.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 21] was used as the reactant.; HRMS [M]+: 779.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 21] was used as the reactant.; HRMS [M]+: 704.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 21] was used as the reactant.; HRMS [M] + : 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 21] was used as the reactant.; HRMS [M]+: 615.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 21] was used as the reactant.; HRMS [M]+: 665.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 22] was used as the reactant.; HRMS [M] + : 614.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 22] was used as the reactant.; HRMS [M]+: 779.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 22] was used as the reactant.; HRMS [M]+: 704.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 22] was used as the reactant.; HRMS [M] + : 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 22] was used as the reactant.; HRMS [M]+: 615.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 22] was used as the reactant.; HRMS [M]+: 665.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 23] was used as the reactant.; HRMS [M] + : 763.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 23] was used as the reactant.; HRMS [M]+: 828.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 23] was used as the reactant.; HRMS [M]+: 753.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 23] was used as the reactant.; HRMS [M] + : 752.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 23] was used as the reactant.; HRMS [M]+: 664.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 23] was used as the reactant.; HRMS [M]+: 714.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 24] was used as the reactant.; HRMS [M] + : 714.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 24] was used as the reactant.; HRMS [M]+: 779.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 24] was used as the reactant.; HRMS [M]+: 704.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 24] was used as the reactant.; HRMS [M] + : 703.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 24] was used as the reactant.; HRMS [M]+: 615.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 24] was used as the reactant.; HRMS [M]+: 665.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 25] was used as the reactant; HRMS [M] + : 751.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 25] was used as the reactant.; HRMS [M]+: 815.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 25] was used as the reactant.; HRMS [M]+: 741.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 25] was used as the reactant; HRMS [M] + : 740.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 25] was used as the reactant.; HRMS [M]+: 652.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 25] was used as the reactant.; HRMS [M]+: 702.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 26] was used as the reactant.; HRMS [M] + : 761.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 26] was used as the reactant.; HRMS [M]+: 816.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 26] was used as the reactant.; HRMS [M]+: 741.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 26] was used as the reactant.; HRMS [M] + : 740.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 26] was used as the reactant.; HRMS [M]+: 652.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 26] was used as the reactant.; HRMS [M]+: 702.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 27] was used as the reactant.; HRMS [M] + : 776.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 27] was used as the reactant.; HRMS [M]+: 841.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 27] was used as the reactant.; HRMS [M]+: 766.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 27] was used as the reactant.; HRMS [M] + : 775.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 27] was used as the reactant.; HRMS [M]+: 677.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 27] was used as the reactant.; HRMS [M]+: 727.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 28] was used as the reactant.; HRMS [M] + : 752.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 28] was used as the reactant.; HRMS [M]+: 817.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 28] was used as the reactant.; HRMS [M]+: 742.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 28] was used as the reactant.; HRMS [M] + : 741.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 28] was used as the reactant.; HRMS [M]+: 653.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 28] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 29] was used as the reactant.; HRMS [M] + : 752.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 29] was used as the reactant.; HRMS [M]+: 817.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 29] was used as the reactant.; HRMS [M]+: 742.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 29] was used as the reactant.; HRMS [M] + : 741.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 29] was used as the reactant.; HRMS [M]+: 653.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 29] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 30] was used as the reactant.; HRMS [M] + : 652.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 30] was used as the reactant.; HRMS [M]+: 817.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 30] was used as the reactant.; HRMS [M]+: 742.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 30] was used as the reactant.; HRMS [M] + : 741.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 30] was used as the reactant.; HRMS [M]+: 653.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 30] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 31] was used as the reactant.; HRMS [M] + : 801.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 31] was used as the reactant.; HRMS [M]+: 866.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 31] was used as the reactant.; HRMS [M]+: 791.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 31] was used as the reactant.; HRMS [M] + : 790.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 31] was used as the reactant.; HRMS [M]+: 702.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 31] was used as the reactant.; HRMS [M]+: 752.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 32] was used as the reactant.; HRMS [M] + : 752.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 32] was used as the reactant.; HRMS [M]+: 817.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 32] was used as the reactant.; HRMS [M]+: 742.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 32] was used as the reactant.; HRMS [M] + : 741.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 32] was used as the reactant.; HRMS [M]+: 653.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 32] was used as the reactant.; HRMS [M]+: 703.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 664.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 680.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 729.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 653.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 670.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 33] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 34] was used as the reactant.; HRMS [M] + : 664.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 680.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 730.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 654.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 34] was used as the reactant.; HRMS [M] + : 653.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 670.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 565.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 670.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 641.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 34] was used as the reactant.; HRMS [M]+: 680.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 35] was used as the reactant.; HRMS [M] + : 689.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 739.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 705.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 754.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 679.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 35] was used as the reactant.; HRMS [M] + : 678.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 695.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 590.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 640.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 691.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 666.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 35] was used as the reactant.; HRMS [M]+: 705.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 36] was used as the reactant.; HRMS [M] + : 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 715.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 681.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 730.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 655.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 36] was used as the reactant.; HRMS [M] + : 654.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 671.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 566.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 616.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 667.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 642.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 36] was used as the reactant.; HRMS [M]+: 681.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 37] was used as the reactant.; HRMS [M] + : 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 715.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 681.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 730.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 655.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 37] was used as the reactant.; HRMS [M] + : 654.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 671.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 566.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 616.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 667.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 642.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 37] was used as the reactant.; HRMS [M]+: 681.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 38] was used as the reactant.; HRMS [M] + : 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 715.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 681.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 730.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 655.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 38] was used as the reactant.; HRMS [M] + : 654.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 671.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 566.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 616.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 667.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 642.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 38] was used as the reactant.; HRMS [M]+: 681.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 39] was used as the reactant.; HRMS [M] + : 714.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 764.28
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 730.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 779.29
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 704.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 39] was used as the reactant.; HRMS [M] + : 703.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 720.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 615.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 665.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 10], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 716.25
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 11], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 691.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 12], except that [Preparation Example 39] was used as the reactant.; HRMS [M]+: 630.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 1], except that [Preparation Example 40] was used as the reactant.; HRMS [M] + : 665.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 2], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 715.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 3], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 681.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 4], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 730.27
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 5], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 655.23
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 6], except that [Preparation Example 40] was used as the reactant.; HRMS [M] + : 654.24
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 7], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 671.26
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 8], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 566.21
  • the target compound was obtained by performing the same procedure as in [Synthesis Example 9], except that [Preparation Example 40] was used as the reactant.; HRMS [M]+: 616.23

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le comprenant. Le composé selon la présente invention est utilisé pour une couche de matériau organique d'un élément électroluminescent organique, de préférence une couche électroluminescente, de façon à améliorer l'efficacité lumineuse, la tension de commande, la durée de vie, etc. de l'élément électroluminescent organique.
PCT/KR2020/004926 2019-04-11 2020-04-10 Composé organique et élément électroluminescent organique le comprenant WO2020209679A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113816898A (zh) * 2021-03-29 2021-12-21 烟台显华化工科技有限公司 一种化合物、电子传输材料、有机电致发光器件和显示装置
CN114605402A (zh) * 2020-12-09 2022-06-10 江苏三月科技股份有限公司 一种含有三嗪结构的有机化合物及其应用
EP4043453A1 (fr) * 2021-02-11 2022-08-17 Idemitsu Kosan Co., Ltd. Composé, matériau pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant le composé
KR20230137903A (ko) 2021-01-29 2023-10-05 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광소자 및 전자 기기

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102517278B1 (ko) * 2020-11-12 2023-04-05 주식회사 랩토 트리아진 또는 피리미딘 유도체, 및 이를 포함한 유기전계발광소자
KR102577792B1 (ko) * 2020-12-23 2023-09-13 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140087804A (ko) * 2012-12-31 2014-07-09 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20150142822A (ko) * 2014-06-11 2015-12-23 삼성디스플레이 주식회사 유기 발광 소자
KR20160007985A (ko) * 2014-07-10 2016-01-21 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치
KR20160075492A (ko) * 2013-11-13 2016-06-29 이데미쓰 고산 가부시키가이샤 화합물, 유기 일렉트로루미네선스 소자용 재료, 유기 일렉트로루미네선스 소자 및 전자 기기
KR20160090238A (ko) * 2015-01-20 2016-07-29 삼성디스플레이 주식회사 유기 발광 소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2725080B1 (fr) 2011-06-27 2018-01-24 LG Chem, Ltd. Nouveau composé et dispositif électroluminescent organique l'utilisant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140087804A (ko) * 2012-12-31 2014-07-09 제일모직주식회사 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치
KR20160075492A (ko) * 2013-11-13 2016-06-29 이데미쓰 고산 가부시키가이샤 화합물, 유기 일렉트로루미네선스 소자용 재료, 유기 일렉트로루미네선스 소자 및 전자 기기
KR20150142822A (ko) * 2014-06-11 2015-12-23 삼성디스플레이 주식회사 유기 발광 소자
KR20160007985A (ko) * 2014-07-10 2016-01-21 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치
KR20160090238A (ko) * 2015-01-20 2016-07-29 삼성디스플레이 주식회사 유기 발광 소자

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CN114605402A (zh) * 2020-12-09 2022-06-10 江苏三月科技股份有限公司 一种含有三嗪结构的有机化合物及其应用
CN114605402B (zh) * 2020-12-09 2023-09-26 江苏三月科技股份有限公司 一种含有三嗪结构的有机化合物及其应用
KR20230137903A (ko) 2021-01-29 2023-10-05 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광소자 및 전자 기기
EP4043453A1 (fr) * 2021-02-11 2022-08-17 Idemitsu Kosan Co., Ltd. Composé, matériau pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant le composé
CN113816898A (zh) * 2021-03-29 2021-12-21 烟台显华化工科技有限公司 一种化合物、电子传输材料、有机电致发光器件和显示装置

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