Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to: a novel compound having excellent electronic stability; and an organic electroluminescent device comprising the compound in at least one organic layer so as to have improved characteristics such as luminous efficiency, driving voltage and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the novel compound and the same in one or more organic layers.

[0002] Research on organic electroluminescent (EL) devices began in 1987 with the introduction of a laminated organic EL device divided into functional layers: a hole layer and a light-emitting layer. Since then, the development of high-efficiency, long-life organic EL devices has progressed by introducing characteristic organic layers within the device, leading to the development of specialized materials for this purpose.

[0003] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified according to their function, such as luminescent materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0004] The light-emitting layer materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials according to the emission color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. In addition, a host / dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. The dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials is focusing on not only phosphorescent dopants but also phosphorescent host materials because it can theoretically improve luminous efficiency by up to four times compared to fluorescence. Currently, NPB, BCP, Alq3, etc. are widely known as materials used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as luminescent materials. In particular, among luminescent materials, Ir-containing metal complex compounds such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2 are used as blue, green, and red dopant materials, as phosphorescent materials that have great advantages in terms of improving efficiency. Currently, CBP has shown excellent properties as a phosphorescent host material.

[0005] However, while conventional luminescent materials offer advantages in terms of luminescence properties, their poor electronic stability prevents them from achieving satisfactory lifetimes in organic electroluminescent devices. Therefore, the development of luminescent materials with superior performance is urgently needed.

[0006] In addition, various phosphorescent materials have been developed to date, and in particular, CBP (4,4'-N,N'-dicarbazolbiphenyl) is the most widely known phosphorescent host material to date, and organic electroluminescent devices using materials in which various substituents are introduced into carbazole (Japanese Patent Application Laid-Open No. 2008-214244) or BAlq derivatives as hosts are known.

[0007] However, organic electroluminescent devices using phosphorescent materials have a higher operating voltage than devices using fluorescent materials when using host materials such as BAlq and CBP, so there is no significant advantage in terms of power efficiency. In addition, the lifespan of the device is not satisfactory, so there is a demand for the development of more stable and high-performance host materials.

[0008] [Prior Art Literature]

[0009] [Patent Document]

[0010] (Patent Document 1) Korean Patent Publication No. 10-2023-0145302

[0011] The present invention has been devised to solve the above-mentioned problems, and more specifically, the technical task is to provide a novel compound having excellent electronic stability and being usable as an organic layer material of an organic electroluminescent device, specifically as a host material of a light-emitting layer.

[0012] In addition, another technical task of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound described above.

[0013] Other objects and advantages of the present invention can be more clearly explained by the detailed description of the invention and the claims below.

[0014] To achieve the above technical task, the present invention provides a compound represented by the following chemical formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] X1 to X3 are the same or different from each other, and are each independently N or CR, provided that at least one of X1 to X3 is N,

[0019] Y1 and Y2 are the same or different from each other, and are each independently selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5), and Si(Ar6)(Ar7),

[0020] L1 and L2 are the same or different and are each independently C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms,

[0021] Ar1 to Ar7 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C6~C 40 Aryl group of, heteroaryl group of 5 to 40 nuclear atoms, C6~C 40 Aryloxy group of C1~C 40 Alkyloxy group, C6~C 40 Arylamine group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C1~C 40 Alkylsilyl group, C1~C 40 Alkyl boron group, C6~C 40 Aryl boron group, C6~C 40 Arylphosphine group, C6~C 40 Arylphosphine oxide group and C6~C 40 is selected from the group consisting of arylsilyl groups, or these can combine with any adjacent groups to form a condensed ring,

[0022] m is an integer from 1 to 3,

[0023] o is an integer from 0 to 2,

[0024] Dn represents the number of deuterium atoms and is an integer greater than or equal to 0.

[0025] R1 is a halogen group, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It can be selected from the group consisting of arylamine groups,

[0026] The alkyl group, alkenyl group, alkynyl group, and aryl group of the above Ar1 to Ar7; and R1 are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of aryl groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0027] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0028] For example, the organic layer of one or more layers includes at least one selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer, and the light-emitting layer may include a compound represented by the chemical formula 1 as a host, specifically, an N-type host.

[0029] As one embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material of an organic electroluminescent device because it has excellent carrier transport ability, luminescence ability, and heat resistance.

[0030] In particular, when the compound represented by the chemical formula 1 of the present invention is used as a host for a light-emitting layer, it can exhibit low driving voltage, fast mobility, high current efficiency, and long life characteristics compared to conventionally known host materials.

[0031] Accordingly, the organic electroluminescent device including the compound of the above chemical formula 1 can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0032] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0033] Hereinafter, the present invention will be described in detail.

[0034] Organic compounds

[0035] The novel compound of the present invention has a basic skeletal structure comprising two dibenzo moieties (e.g., a ring containing Y1 and Y2) and one azine group (e.g., a ring containing X1 to X3), wherein at least one moiety (e.g., Ar1 and / or Ar2) is introduced into the azine group, and the two dibenzo moieties are connected by at least one linker (Linker, L1).

[0036] Specifically, the compound represented by Chemical Formula 1 according to the present invention is a novel N-type host that essentially comprises two dibenzo moieties (e.g., rings containing Y1 and Y2) and one azine group (e.g., rings containing X1 to X3). Such a compound has stronger electron stability than existing host materials, specifically, N-type host materials, and thus can maximize its performance as an N-type host.

[0037] Furthermore, compared to existing N-type host materials, it exhibits superior electronic stability, enabling the device to maintain stable lifetime characteristics even during initial device characteristics. Accordingly, when the compound is used as a light-emitting layer material, the electronic stability of the device itself is enhanced, enabling the production of high-performance OLED devices.

[0038] Meanwhile, in terms of potential energy, deuterium (D) has a higher molecular mass and lower zero-point energy than hydrogen (H), making it relatively more difficult for deuterium to dissociate in a reaction. This low zero-point energy increases the bond dissociation energy, which lowers the reactivity and thus increases the stability of molecules containing deuterium (Molecules 2014, 19 Chem. Commun., 2014, 50, 14870-14872 J. Org. Chem. 2004, 69, 7212-7219).

[0039] Accordingly, when the compound of chemical formula 1 of the present invention is substituted with deuterium (D), the green color purity can be maximized compared to a compound of the same structure that does not contain deuterium, and the weakened intramolecular bonding force between carbon and hydrogen can be further increased, and the stability of the material can be strengthened, thereby significantly improving the lifespan characteristics of the device.

[0040] In one embodiment of the present invention, the number of substituted deuterium atoms (Dn) in the compound of the above chemical formula 1 may be 0 or more, specifically 0 to 50, and more specifically 0 to 30.

[0041] As described above, when the compound represented by the chemical formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably as an emitting layer material (a blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, or a life-span improvement layer material, the performance and life-span characteristics of the organic electroluminescent device can be significantly improved. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0042] Specifically, the compound represented by the chemical formula 1 of the present invention has a basic skeletal structure including two dibenzo moieties (e.g., a ring containing Y1 and Y2) and one azine group (e.g., a ring containing X1 to X3), to which at least one moiety (e.g., Ar1 and / or Ar2) is introduced, and the two dibenzo moieties are connected by at least one linker (Linker, L1).

[0043] Y1 and Y2 included in the above two dibenzo moieties are the same or different, and can be independently selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5), and Si(Ar6)(Ar7). Specifically, Y1 and Y2 can be the same.

[0044] In one embodiment of the present invention, when Y1 and Y2 are O, the compound of the above formula 1 contains two dibenzofuran groups, and when Y1 and Y2 are S, it contains two dibenzothiophene groups.

[0045] Meanwhile, in the present invention, two dibenzo moieties (e.g., Y1 and Y2-containing rings) are conveniently referred to as a first dibenzo moiety (e.g., Y1-containing ring) and a second dibenzo moiety (e.g., Y2-containing ring).

[0046] One phenyl ring of the first dibenzo moiety (e.g., the Y1-containing ring), for example, one phenyl ring that is not connected to the second dibenzo moiety, may be substituted with various substituents for R1. Such R1 may be a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, a C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It can be selected from the group consisting of arylamine groups.

[0047] In one embodiment of the present invention, R1 is C6~C 60 It may be an aryl group or a heteroaryl group having 5 to 60 nuclear atoms.

[0048] In this way, by introducing an aryl group or heteroaryl group other than hydrogen to R1, the stability for injected electrons can be increased, and accordingly, a synergy effect of the overall characteristics of the organic electroluminescent device having the compound of the above chemical formula 1 can be realized.

[0049] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 2 to 5, depending on the position of R1 introduced into the first dibenzo moiety.

[0050] [Chemical Formula 2]

[0051]

[0052] [Chemical Formula 3]

[0053]

[0054] [Chemical Formula 4]

[0055]

[0056] [Chemical Formula 5]

[0057]

[0058]

[0059] In one embodiment of the present invention, when the compound represented by the chemical formula 1 is chemical formula 2 or chemical formula 5, it may have long-life characteristics.

[0060] In the above chemical formulas 2 to 5, X1, X2, X3, Y1, Y2, L1, L2, Ar1, Ar2, m, o, Dn, and R1 are each as defined in the above chemical formula 1.

[0061] In the present invention, a second dibenzo moiety (e.g., a Y2-containing ring) is positioned between a first dibenzo moiety (e.g., a Y1-containing ring) and an azine group (e.g., a X1 to X3-containing ring), and a linker (linker1, L1) connecting the first dibenzo moiety and the second dibenzo moiety exists between them. In this way, when a linker exists between the first dibenzo moiety and the second dibenzo moiety, the HOMO region can be expanded, thereby providing a benefit to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate HOMO-LUMO overlap. In addition, the stability of the molecule can be increased.

[0062] In one embodiment of the present invention, the L1 may be at least one or more, and may be C6~C 60 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms. Here, m in the chemical formula 1 is an integer of 1 to 3, specifically an integer of 1 to 2, and more specifically 1.

[0063] In this way, by introducing an arylene group or heteroarylene group to L1, the stability for injected electrons can be increased, and accordingly, a synergy effect of the overall characteristics of the organic electroluminescent device including the compound of the above chemical formula 1 can be realized.

[0064] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 6 to 9, depending on the position of L1 introduced into the first dibenzo moiety. However, the present invention is not limited thereto.

[0065] [Chemical Formula 6]

[0066]

[0067]

[0068] [Chemical Formula 7]

[0069]

[0070]

[0071] [Chemical Formula 8]

[0072]

[0073]

[0074] [Chemical Formula 9]

[0075]

[0076] In the above chemical formulas 6 to 9, X1, X2, X3, Y1, Y2, L1, L2, Ar1, Ar2, m, o, Dn, and R1 are each as defined in the above chemical formula 1.

[0077] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 10 to 13 depending on the position of L1 introduced into the second dibenzo moiety. However, the present invention is not limited thereto.

[0078] [Chemical Formula 10]

[0079]

[0080]

[0081] [Chemical Formula 11]

[0082]

[0083]

[0084] [Chemical Formula 12]

[0085]

[0086]

[0087] [Chemical Formula 13]

[0088]

[0089] In the above chemical formulas 10 to 13, X1, X2, X3, Y1, Y2, L1, L2, Ar1, Ar2, m, o, Dn, and R1 are each as defined in the above chemical formula 1.

[0090] Although not shown in the aforementioned chemical formula 1, a compound in which one or both phenyl rings of the second dibenzo moiety are substituted with at least one substituent known in the art (e.g., the same as the R definition) also falls within the scope of the present invention.

[0091] In the chemical formula 1 according to the present invention, among the two dibenzo moieties (e.g., Y1 or Y2-containing rings), the other phenyl ring of the second dibenzo moiety (e.g., Y2-containing ring) may be directly connected to an azine group (e.g., X1 to X3-containing ring) or may be connected by a linker (linker2, L2). Here, o in the chemical formula 1 of the present invention is an integer from 0 to 2.

[0092] In one embodiment of the present invention, each of L1 and / or L2 may be a linker selected from the following structural formula.

[0093]

[0094]

[0095] In the present invention, the azine group (e.g., X1 to X3-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom. In one embodiment of the nitrogen-containing heteroaromatic ring, X1 to X3 are the same or different, and are each independently N or C(R), provided that at least one of X1 to X3 contains N. For example, the azine group may contain 2 or 3 Ns. By including a nitrogen-containing heterocycle in this way, it exhibits better electron absorption properties, which is advantageous for electron injection and transport.

[0096] In an embodiment of the present invention, the X1 to X3 containing ring may be any one selected from the following structural formulas, but is not limited thereto.

[0097]

[0098]

[0099] In the above formula,

[0100] * is (L2) of the above chemical formula 1 o It means a part connected to, and Ar1 and Ar2 are each as defined in chemical formula 1.

[0101] The compound represented by chemical formula 1 according to the present invention described above can be further specified as a compound represented by any one of compounds A-1 to Z-2 exemplified below. However, the compound represented by chemical formula 1 of the present invention is not limited to those exemplified below.

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] In the present invention, “alkyl” refers to a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0110] In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0111] In the present invention, “alkynyl” refers to a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond. Examples of such alkynyl include, but are not limited to, ethynyl and 2-propynyl.

[0112] In the present invention, “cycloalkyl” refers to 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.

[0113] In the present invention, “heterocycloalkyl” means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0114] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, forms in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0115] In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0116] In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0117] In the present invention, “aryloxy” is a monovalent substituent represented by RO-, wherein R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0118] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 6 to 60 carbon atoms.

[0119] In the present invention, “alkylboron” means boron substituted with an alkyl having 1 to 40 carbon atoms, and “arylboron” means boron substituted with an aryl having 6 to 60 carbon atoms.

[0120] In the invention, “arylphosphine” means a phosphine substituted with an aryl having 6 to 60 carbon atoms, and “arylphosphine oxide group” means a phosphine substituted with an aryl having 6 to 60 carbon atoms that contains O.

[0121] In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0122] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms.

[0123] The compound represented by Chemical Formula 1 of the present invention can be prepared without limitation according to methods known in the art. For example, it can be synthesized in various ways by referring to the synthetic process of the following examples.

[0124]

[0125] Organic electroluminescent devices

[0126] The present invention provides an organic electroluminescent device comprising a compound represented by the above chemical formula 1.

[0127] Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1.

[0128] The organic layer of one or more layers includes at least one selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer, and at least one of the organic layers includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a life-span improvement layer, and more specifically, the organic layer including the compound of the chemical formula 1 is a light-emitting layer, and in this case, the compound of the chemical formula 1 may be included as a host material.

[0129] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and / or a dopant material, wherein the compound of formula 1 can be used as the host material, specifically, an N-type host material. In addition to the host material of formula 1, the light-emitting layer may further comprise at least one of a conventional P-type host and an N-type host known in the art.

[0130] When the compound represented by the above chemical formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound represented by the chemical formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light-emitting layer having high efficiency.

[0131] Additionally, the present invention may further include, without limitation, dopants known in the art. The content ratio (mixing ratio) of these is not particularly limited and may be appropriately adjusted within a content range known in the art. For example, the light-emitting layer may include 70 to 99.9 parts by weight of the host and 0.1 to 30 parts by weight of the dopant, based on the total weight of the light-emitting layer.

[0132] The dopant included in the above-mentioned light-emitting layer is not particularly limited as long as it is known in the art, and may include, for example, at least one of a fluorescent dopant and a phosphorescent dopant. Non-limiting examples of usable dopants include anthracene derivatives, pyrene derivatives, arylamine derivatives, metal complex compounds including iridium (Ir) or platinum (Pt), and the like. These dopants can be classified into red dopants, green dopants, and blue dopants, and red dopants, green dopants, and blue dopants commonly known in the art can be used without particular limitation.

[0133] The structure of the organic electroluminescent device of the present invention including the above-described configuration is not particularly limited and may have a configuration known in the art. A non-limiting example thereof may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially laminated. In this case, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

[0134] The organic electroluminescent device according to the present invention can be manufactured by forming the organic layer and electrode using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by Chemical Formula 1.

[0135] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0136] The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, etc. can be used.

[0137] In addition, the anode material may include, but is not limited to, 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 SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0138] Additionally, cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0139] In addition, the hole injection layer, hole transport layer, and electron injection layer are not particularly limited, and conventional materials known in the art can be used.

[0140]

[0141] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0142]

[0143] [Preparation Example 1] Synthesis of DLD-1

[0144]

[0145] <Step 1> Synthesis of 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0146]

[0147]

[0148] Under a nitrogen stream, 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), Pd(PPh3)4 (17.9 g, 15.5 mmol), K2CO3 (106.9 g, 773.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0149] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]furan (73.6 g, yield 67%).

[0150] Mass (theoretical: 354.83, measured: 354 g / mol)

[0151] <Step 2> Synthesis of 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)-1,3,2-dioxaborolane

[0152]

[0153] Under a nitrogen stream, 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]furan (73.6 g, 207.3 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (57.9 g, 228.0 mmol), Pd2(dba)3 (5.7 g, 6.2 mmol), X-Phos (13.8 g, 29.0 mmol), KOAc (39.0 g, 414.6 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0154] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)-1,3,2-dioxaborolane (48.1 g, yield 52%).

[0155] Mass (Theoretical: 446.35 Measured: 446 g / mol)

[0156]

[0157] <Step 3> Synthesis of 1-chloro-8-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan

[0158]

[0159]

[0160] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)-1,3,2-dioxaborolane (48.1 g, 107.8 mmol), 8-bromo-1-chlorodibenzo[b,d]furan (36.4 g, 129.4 mmol), Pd(PPh3)4 (6.2 g, 5.4 mmol), K2CO3 (32.2 g, 269.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0161] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 1-chloro-8-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan (33.1 g, yield 59%).

[0162] Mass (theoretical: 521.01, measured: 521 g / mol)

[0163]

[0164] <Step 4> Synthesis of DLD-1

[0165]

[0166]

[0167]

[0168] Under a nitrogen stream, 1-chloro-8-(2-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan (33.1 g, 63.6 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (17.8 g, 70.0 mmol), Pd2(dba)3 (1.7 g, 1.9 mmol), X-Phos (4.2 g, 8.9 mmol), KOAc (12.0 g, 127.2 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0169] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-1 (21.4 g, yield 55%).

[0170] Mass (theoretical: 612.53, measured: 612 g / mol)

[0171]

[0172] [Preparation Example 2] Synthesis of DLD-2

[0173] <Step 1-4> Synthesis of DLD-2

[0174]

[0175]

[0176]

[0177] The same procedure as steps 1 to 4 of Preparation Example 1 was followed except that (3-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), thereby obtaining the target compound DLD-2 (25.6 g, final yield 13.5%).

[0178] Mass (theoretical: 612.53, measured: 612 g / mol)

[0179]

[0180] [Preparation Example 3] Synthesis of DLD-3

[0181]

[0182] <Step 1-4> Synthesis of DLD-3

[0183]

[0184]

[0185] The same procedure as steps 1 to 4 of Preparation Example 1 was followed except that (4-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-3 (27.9 g, final yield 14.7%).

[0186] Mass (theoretical: 612.53, measured: 612 g / mol)

[0187]

[0188] [Preparation Example 4] Synthesis of DLD-4

[0189]

[0190] <Step 1-4> Synthesis of DLD-4

[0191]

[0192]

[0193] The same procedure as in steps 1 to 4 of Preparation Example 1 was followed except that 3-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), to obtain the target compound DLD-4 (32.6 g, final yield 17.2%).

[0194] Mass (theoretical: 612.53, measured: 612 g / mol)

[0195]

[0196] [Preparation Example 5] Synthesis of DLD-5

[0197]

[0198] <Step 1-4> Synthesis of DLD-5

[0199]

[0200]

[0201] The same procedure as in Steps 1 to 4 of Preparation Example 1 was followed, except that 3-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (3-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-5 (30.6 g, final yield 16.1%).

[0202] Mass (theoretical: 612.53, measured: 612 g / mol)

[0203]

[0204] [Preparation Example 6] Synthesis of DLD-6

[0205]

[0206] <Step 1-4> Synthesis of DLD-6

[0207]

[0208]

[0209] The same procedure as in Steps 1 to 4 of Preparation Example 1 was followed, except that 3-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (4-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-6 (27.0 g, final yield 14.3%).

[0210] Mass (theoretical: 612.53, measured: 612 g / mol)

[0211]

[0212] [Preparation Example 7] Synthesis of DLD-7

[0213]

[0214] <Step 1-4> Synthesis of DLD-7

[0215]

[0216]

[0217] The same procedure as steps 1 to 4 of Preparation Example 1 was followed except that 2-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), to obtain the target compound DLD-7 (48.2 g, final yield 25.4%).

[0218] Mass (theoretical: 612.53, measured: 612 g / mol)

[0219]

[0220] [Preparation Example 8] Synthesis of DLD-8

[0221]

[0222] <Step 1-4> Synthesis of DLD-8

[0223]

[0224]

[0225] The same procedure as in Steps 1 to 4 of Preparation Example 1 was followed, except that 2-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (3-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-8 (29.8 g, final yield 15.7%).

[0226] Mass (theoretical: 612.53, measured: 612 g / mol)

[0227]

[0228] [Preparation Example 9] Synthesis of DLD-9

[0229]

[0230] <Step 1-4> Synthesis of DLD-9

[0231]

[0232]

[0233] The same procedure as in Steps 1 to 4 of Preparation Example 1 was followed, except that 2-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (4-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-9 (36.5 g, final yield 19.2%).

[0234] Mass (theoretical: 612.53, measured: 612 g / mol)

[0235]

[0236] [Preparation Example 10] Synthesis of DLD-10

[0237]

[0238] <Step 1-4> Synthesis of DLD-10

[0239]

[0240]

[0241] The same procedure as steps 1 to 4 of Preparation Example 1 was followed except that 1-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), to obtain the target compound DLD-10 (34.7 g, final yield 18.3%).

[0242] Mass (theoretical: 612.53, measured: 612 g / mol)

[0243]

[0244] [Preparation Example 11] Synthesis of DLD-11

[0245]

[0246] <Step 1-4> Synthesis of DLD-11

[0247]

[0248]

[0249] The same procedure as steps 1 to 4 of Preparation Example 1 was followed, except that 1-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (3-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-11 (30.8 g, final yield 16.3%).

[0250] Mass (theoretical: 612.53, measured: 612 g / mol)

[0251]

[0252] [Preparation Example 12] Synthesis of DLD-12

[0253]

[0254] <Step 1-4> Synthesis of DLD-12

[0255]

[0256]

[0257] The same procedure as steps 1 to 4 of Preparation Example 1 was followed, except that 1-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (4-chlorophenyl)boronic acid (58.1 g, 371.3 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-12 (38.1 g, final yield 20.1%).

[0258] Mass (theoretical: 612.53, measured: 612 g / mol)

[0259]

[0260] [Preparation Example 13] Synthesis of DLD-13

[0261]

[0262] <Step 1-4> Synthesis of DLD-13

[0263]

[0264]

[0265] The same procedure as in steps 1 to 4 of Preparation Example 1 was followed except that 4-bromo-6-phenyldibenzo[b,d]thiophene (100.0 g, 294.8 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), to obtain the target compound DLD-13 (31.5 g, final yield 17.0%).

[0266] Mass (theoretical: 628.59, measured: 628 g / mol)

[0267]

[0268] [Preparation Example 14] Synthesis of DLD-14

[0269]

[0270] <Step 1-4> Synthesis of DLD-14

[0271]

[0272]

[0273] The same procedure as steps 1 to 4 of Preparation Example 1 was followed, except that 6-bromo-1-phenyldibenzo[b,d]thiophene (100.0 g, 294.8 mmol) was used instead of 4-bromo-6-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), and (3-chlorophenyl)boronic acid (55.3 g, 353.7 mmol) was used instead of (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), to obtain the target compound DLD-14 (37.2 g, final yield 20.1%).

[0274] Mass (theoretical: 628.59, measured: 628 g / mol)

[0275]

[0276] [Preparation Example 15] Synthesis of DLD-15

[0277]

[0278] <Step 1> Synthesis of 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6

[0279]

[0280]

[0281]

[0282] Under a nitrogen atmosphere, 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), (3-chlorophenyl-2,4,5,6-d4)boronic acid (54.9 g, 342.5 mmol), Pd(PPh3)4 (16.5 g, 14.3 mmol), K2CO3 (98.6 g, 713.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0283] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (78.2 g, yield 71%).

[0284] Mass (theoretical: 385.99, measured: 385 g / mol)

[0285]

[0286] <Step 2> Synthesis of 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6

[0287]

[0288]

[0289]

[0290] Under a nitrogen stream, 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (78.2 g, 202.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (56.6 g, 222.9 mmol), Pd2(dba)3 (5.6 g, 6.1 mmol), X-Phos (13.5 g, 28.4 mmol), KOAc (38.2 g, 405.3 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0291] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (50.3 g, yield 52%).

[0292] Mass (Theoretical: 477.51 Measured: 477 g / mol)

[0293]

[0294] <Step 3> Synthesis of 1-chloro-8-(3-(6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl-1,2,3,7,8,9-d6)phenyl-2,4,5,6-d4)dibenzo[b,d]furan-2,3,4,6,7,9-d6

[0295]

[0296]

[0297]

[0298] Under a nitrogen atmosphere, 4-(3-chlorophenyl-2,4,5,6-d4)-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (50.3 g, 105.4 mmol), 8-bromo-1-chlorodibenzo[b,d]furan-2,3,4,6,7,9-d6 (36.4 g, 126.5 mmol), Pd(PPh3)4 (6.1 g, 5.3 mmol), K2CO3 (36.4 g, 263.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0299] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 1-chloro-8-(3-(6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl-1,2,3,7,8,9-d6)phenyl-2,4,5,6-d4)dibenzo[b,d]furan-2,3,4,6,7,9-d6 (31.2 g, yield 53%).

[0300] Mass (theoretical: 558.20, measured: 558 g / mol)

[0301]

[0302] <Step 4> Synthesis of DLD-15

[0303]

[0304]

[0305]

[0306] Under a nitrogen atmosphere, 1-chloro-8-(3-(6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl-1,2,3,7,8,9-d6)phenyl-2,4,5,6-d4)dibenzo[b,d]furan-2,3,4,6,7,9-d6 (31.2 g, 55.9 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (15.6 g, 61.4 mmol), Pd2(dba)3(1.5 g, 1.7 mmol), X-Phos (3.7 g, 7.8 mmol), KOAc (10.5 g, 111.7 mmol) and 1,4-Dioxane (2000 ml) were mixed. Stirred at 130℃ for 12 hours.

[0307] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-15 (26.5 g, yield 73%).

[0308] Mass (theoretical: 649.72, measured: 649 g / mol)

[0309]

[0310] [Preparation Example 16] Synthesis of DLD-16

[0311]

[0312] <Step 1-4> Synthesis of DLD-16

[0313]

[0314]

[0315] The same procedure as steps 1 to 4 of Preparation Example 15 was followed except that 6-bromo-1-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol) was used instead of 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), to obtain the target compound DLD-16 (29.1 g, final yield 15.7%).

[0316] Mass (theoretical: 649.72, measured: 649 g / mol)

[0317]

[0318] [Preparation Example 17] Synthesis of DLD-17

[0319]

[0320] <Step 1-4> Synthesis of DLD-17

[0321]

[0322]

[0323] The same procedure as steps 1 to 4 of Preparation Example 15 was followed except that 4-bromo-6-(phenyl-d5)dibenzo[b,d]furan-1,2,3,7,8,9-d6 (100.0 g, 299.2 mmol) was used instead of 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), to obtain the target compound DLD-17 (30.3 g, final yield 16.0%).

[0324] Mass (theoretical: 633.66, measured: 633 g / mol)

[0325]

[0326] [Preparation Example 18] Synthesis of DLD-18

[0327]

[0328] <Step 1-4> Synthesis of DLD-18

[0329]

[0330]

[0331] The same procedure as steps 1 to 4 of Preparation Example 15 was followed except that 6-bromo-1-(phenyl-d5)dibenzo[b,d]furan-2,3,4,7,8,9-d6 (100.0 g, 299.2 mmol) was used instead of 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), thereby obtaining the target compound DLD-18 (30.6 g, final yield 16.2%).

[0332] Mass (theoretical: 633.66, measured: 633 g / mol)

[0333]

[0334] [Preparation Example 19] Synthesis of DLD-19

[0335]

[0336] <Step 1-4> Synthesis of DLD-19

[0337]

[0338]

[0339] The same procedure as in Steps 1 to 4 of Preparation Example 15 was followed, except that 3-bromo-6-(phenyl-d5)dibenzo[b,d]furan-1,2,4,7,8,9-d6 (100.0 g, 299.2 mmol) was used instead of 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), and (4-chlorophenyl-2,3,5,6-d4)boronic acid (57.6 g, 359.0 mmol) was used instead of (3-chlorophenyl-2,4,5,6-d4)boronic acid (57.6 g, 359.0 mmol), to obtain the target compound DLD-19 (49.5 g, final yield 26.1%).

[0340] Mass (theoretical: 633.66, measured: 633 g / mol)

[0341]

[0342] [Preparation Example 20] Synthesis of DLD-20

[0343]

[0344] <Step 1-4> Synthesis of DLD-20

[0345]

[0346]

[0347] The same procedure as in Steps 1 to 4 of Preparation Example 15 was followed, except that 7-bromo-1-(phenyl-d5)dibenzo[b,d]furan-2,3,4,6,8,9-d6 (100.0 g, 299.2 mmol) was used instead of 4-bromo-6-(phenyl-d5)dibenzo[b,d]thiophene-1,2,3,7,8,9-d6 (100.0 g, 285.5 mmol), and (4-chlorophenyl-2,3,5,6-d4)boronic acid (57.6 g, 359.0 mmol) was used instead of (3-chlorophenyl-2,4,5,6-d4)boronic acid (57.6 g, 359.0 mmol), to obtain the target compound DLD-20 (46.7 g, final yield 24.7%).

[0348] Mass (theoretical: 633.66, measured: 633 g / mol)

[0349]

[0350] [Preparation Example 21] Synthesis of DLD-21

[0351]

[0352] <Step 1> Synthesis of 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]thiophene

[0353]

[0354]

[0355]

[0356] Under a nitrogen stream, 4-bromo-6-phenyldibenzo[b,d]thiophene (100.0 g, 294.8 mmol), (2-chlorophenyl)boronic acid (55.3 g, 353.7 mmol), Pd(PPh3)4 (17.0 g, 14.7 mmol), K2CO3 (101.8 g, 736.9 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0357] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]thiophene (76.5 g, yield 70%).

[0358] Mass (theoretical: 370.89, measured: 370 g / mol)

[0359]

[0360] <Step 2> Synthesis of 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)-1,3,2-dioxaborolane

[0361]

[0362]

[0363]

[0364] Under a nitrogen stream, 4-(2-chlorophenyl)-6-phenyldibenzo[b,d]thiophene (76.5 g, 206.3 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (57.6 g, 227.0 mmol), Pd2(dba)3 (5.7 g, 6.2 mmol), X-Phos (13.8 g, 29.0 mmol), KOAc (39.0 g, 412.7 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0365] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)-1,3,2-dioxaborolane (69.7 g, yield 73%).

[0366] Mass (Theoretical: 462.41 Measured: 462 g / mol)

[0367]

[0368] <Step 3> Synthesis of 1-chloro-8-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)dibenzo[b,d]thiophene

[0369]

[0370]

[0371]

[0372] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)-1,3,2-dioxaborolane (69.7 g, 150.6 mmol), 8-bromo-1-chlorodibenzo[b,d]thiophene (53.8 g, 180.8 mmol), Pd(PPh3)4 (8.7 g, 7.5 mmol), K2CO3 (52.0 g, 376.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0373] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 1-chloro-8-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)dibenzo[b,d]thiophene (49.2 g, yield 59%).

[0374] Mass (theoretical: 553.13, measured: 553 g / mol)

[0375]

[0376] <Step 4> Synthesis of DLD-21

[0377]

[0378]

[0379]

[0380] Under a nitrogen stream, 1-chloro-8-(2-(6-phenyldibenzo[b,d]thiophen-4-yl)phenyl)dibenzo[b,d]thiophene (49.2 g, 88.9 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (24.8 g, 97.8 mmol), Pd2(dba)3 (2.4 g, 2.7 mmol), X-Phos (5.9 g, 12.4 mmol), KOAc (16.7 g, 177.7 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0381] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-21 (41.2 g, yield 72%).

[0382] Mass (theoretical: 644.65, measured: 644 g / mol)

[0383]

[0384] [Preparation Example 22] Synthesis of DLD-22

[0385]

[0386] <Step 1> Synthesis of 2-(2-chlorophenyl)-9,9-dimethyl-5-phenyl-9H-fluorene

[0387]

[0388]

[0389]

[0390] Under a nitrogen stream, 2-bromo-9,9-dimethyl-5-phenyl-9H-fluorene (100.0 g, 286.3 mmol), (2-chlorophenyl)boronic acid (53.7 g, 343.6 mmol), Pd(PPh3)4 (16.5 g, 14.3 mmol), K2CO3 (98.9 g, 715.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0391] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 2-(2-chlorophenyl)-9,9-dimethyl-5-phenyl-9H-fluorene (74.2 g, yield 68%).

[0392] Mass (theoretical: 380.92, measured: 380 g / mol)

[0393]

[0394] <Step 2> Synthesis of 2-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0395]

[0396]

[0397]

[0398] Under a nitrogen stream, 2-(2-chlorophenyl)-9,9-dimethyl-5-phenyl-9H-fluorene (74.2 g, 194.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (54.4 g, 214.2 mmol), Pd2(dba)3 (5.3 g, 5.8 mmol), X-Phos (13.0 g, 27.3 mmol), KOAc (36.7 g, 389.4 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0399] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 2-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (65.3 g, yield 71%).

[0400] Mass (Theoretical: 472.44 Measured: 472 g / mol)

[0401]

[0402] <Step 3> Synthesis of 1-chloro-8-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)dibenzo[b,d]furan

[0403]

[0404]

[0405]

[0406] Under a nitrogen stream, 2-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (65.3 g, 138.2 mmol), 8-bromo-1-chlorodibenzo[b,d]furan (46.7 g, 165.9 mmol), Pd(PPh3)4 (8.0 g, 6.9 mmol), K2CO3 (47.8 g, 345.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0407] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 1-chloro-8-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)dibenzo[b,d]furan (49.2 g, yield 65%).

[0408] Mass (theoretical: 547.09, measured: 547 g / mol)

[0409]

[0410] <Step 4> Synthesis of DLD-22

[0411]

[0412]

[0413]

[0414] Under a nitrogen stream, 1-chloro-8-(2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)phenyl)dibenzo[b,d]furan (49.2 g, 89.9 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (25.1 g, 98.8 mmol), Pd2(dba)3 (2.5 g, 2.7 mmol), X-Phos (6.0 g, 12.6 mmol), KOAc (16.9 g, 179.7 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0415] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-22 (40.2 g, yield 70%).

[0416] Mass (theoretical: 638.61, measured: 638 g / mol)

[0417]

[0418] [Preparation Example 23] Synthesis of DLD-23

[0419]

[0420] <Step 1> Synthesis of 3-(3-chlorophenyl)-9-phenyl-9H-carbazole

[0421]

[0422]

[0423]

[0424] Under a nitrogen stream, 3-bromo-9-phenyl-9H-carbazole (100.0 g, 310.4 mmol), (2-chlorophenyl)boronic acid (58.2 g, 372.4 mmol), Pd(PPh3)4 (17.9 g, 15.5 mmol), K2CO3 (107.2 g, 775.9 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0425] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 3-(3-chlorophenyl)-9-phenyl-9H-carbazole (82.4 g, yield 75%).

[0426] Mass (theoretical: 353.85, measured: 353 g / mol)

[0427]

[0428] <Step 2> Synthesis of 9-phenyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

[0429]

[0430]

[0431]

[0432] Under a nitrogen stream, 3-(3-chlorophenyl)-9-phenyl-9H-carbazole (82.4 g, 232.8 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (65.0 g, 256.0 mmol), Pd2(dba)3 (6.4 g, 7.0 mmol), X-Phos (15.5 g, 32.6 mmol), KOAc (43.8 g, 465.5 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0433] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 9-phenyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (76.7 g, yield 74%).

[0434] Mass (Theoretical: 445.37 Measured: 445 g / mol)

[0435]

[0436] <Step 3> Synthesis of 3-(3-(9-chlorodibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole

[0437]

[0438]

[0439]

[0440] Under a nitrogen stream, 9-phenyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (76.7 g, 172.3 mmol), 8-bromo-1-chlorodibenzo[b,d]furan (58.2 g, 206.7 mmol), Pd(PPh3)4 (10.0 g, 8.6 mmol), K2CO3 (59.5 g, 430.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0441] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 3-(3-(9-chlorodibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole (66.3 g, yield 74%).

[0442] Mass (theoretical: 520.03, measured: 520 g / mol)

[0443]

[0444] <Step 4> Synthesis of DLD-23

[0445]

[0446]

[0447]

[0448] Under a nitrogen stream, 3-(3-(9-chlorodibenzo[b,d]furan-2-yl)phenyl)-9-phenyl-9H-carbazole (66.3 g, 127.5 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (35.6 g, 140.2 mmol), Pd2(dba)3 (3.5 g, 3.8 mmol), X-Phos (8.5 g, 17.8 mmol), KOAc (24.0 g, 254.9 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0449] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-23 (58.5 g, yield 75%).

[0450] Mass (theoretical: 611.55, measured: 611 g / mol)

[0451]

[0452] [Preparation Example 24] Synthesis of DLD-24

[0453]

[0454] <Step 1> Synthesis of 8-(3-chlorophenyl)-1-phenyldibenzo[b,d]furan

[0455]

[0456]

[0457]

[0458] Under a nitrogen stream, 8-bromo-1-phenyldibenzo[b,d]furan (100.0 g, 309.4 mmol), (2-chlorophenyl)boronic acid (58.1 g, 371.3 mmol), Pd(PPh3)4 (17.9 g, 15.5 mmol), K2CO3 (106.9 g, 773.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0459] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 8:1 (v / v)) to obtain 8-(3-chlorophenyl)-1-phenyldibenzo[b,d]furan (74.7 g, yield 68%).

[0460] Mass (theoretical: 354.83, measured: 354 g / mol)

[0461]

[0462] <Step 2> Synthesis of 4,4,5,5-tetramethyl-2-(3-(9-phenyldibenzo[b,d]furan-2-yl)phenyl)-1,3,2-dioxaborolane

[0463]

[0464]

[0465]

[0466] Under a nitrogen stream, 8-(3-chlorophenyl)-1-phenyldibenzo[b,d]furan (74.7 g, 210.4 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (58.8 g, 231.4 mmol), Pd2(dba)3 (5.8 g, 6.3 mmol), X-Phos (14.0 g, 29.5 mmol), KOAc (39.6 g, 420.8 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0467] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(3-(9-phenyldibenzo[b,d]furan-2-yl)phenyl)-1,3,2-dioxaborolane (67.6 g, yield 72%).

[0468] Mass (Theoretical: 446.35 Measured: 446 g / mol)

[0469]

[0470] <Step 3> Synthesis of 8-(3-(9-chlorodibenzo[b,d]thiophen-2-yl)phenyl)-1-phenyldibenzo[b,d]furan

[0471]

[0472]

[0473]

[0474] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(3-(9-phenyldibenzo[b,d]furan-2-yl)phenyl)-1,3,2-dioxaborolane (67.6 g, 151.5 mmol), 8-bromo-1-chlorodibenzo[b,d]thiophene (54.1 g, 181.8 mmol), Pd(PPh3)4 (8.8 g, 7.6 mmol), K2CO3 (52.3 g, 378.7 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0475] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:DCM = 5:1 (v / v)) to obtain 8-(3-(9-chlorodibenzo[b,d]thiophen-2-yl)phenyl)-1-phenyldibenzo[b,d]furan (56.1 g, yield 69%).

[0476] Mass (theoretical: 537.07, measured: 537 g / mol)

[0477]

[0478] <Step 4> Synthesis of DLD-24

[0479]

[0480]

[0481]

[0482] Under a nitrogen stream, 8-(3-(9-chlorodibenzo[b,d]thiophen-2-yl)phenyl)-1-phenyldibenzo[b,d]furan (56.1 g, 104.5 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (29.2 g, 115.0 mmol), Pd2(dba)3 (2.9 g, 3.1 mmol), X-Phos (7.0 g, 14.6 mmol), KOAc (19.7 g, 209.1 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0483] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain DLD-24 (46.7 g, yield 71%).

[0484] Mass (theoretical: 628.59, measured: 628 g / mol)

[0485]

[0486] [Synthesis Example 1] Synthesis of A-1

[0487]

[0488]

[0489]

[0490] Under a nitrogen stream, DLD-1 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0491] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound A-1 (8.0 g, yield 68%).

[0492] Mass (theoretical: 717.83, measured: 717 g / mol)

[0493]

[0494] [Synthesis Example 2] Synthesis of A-2

[0495]

[0496]

[0497]

[0498] The same procedure as in Synthetic Example 1 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-2 (7.0 g, yield 59%).

[0499] Mass (theoretical: 727.89, measured: 727 g / mol)

[0500]

[0501] [Synthesis Example 3] Synthesis of A-3

[0502]

[0503]

[0504]

[0505] The same procedure as in Synthesis Example 1 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-3 (6.7 g, yield 52%).

[0506] Mass (theoretical: 793.93, measured: 793 g / mol)

[0507]

[0508] [Synthesis Example 4] Synthesis of A-4

[0509]

[0510]

[0511]

[0512] The same procedure as in Synthesis Example 1 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-4 (8.8 g, yield 68%).

[0513] Mass (theoretical: 793.93, measured: 793 g / mol)

[0514]

[0515] [Synthesis Example 5] Synthesis of A-5

[0516]

[0517]

[0518]

[0519] The same procedure as in Synthesis Example 1 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-5 (7.9 g, yield 61%).

[0520] Mass (theoretical: 793.93, measured: 793 g / mol)

[0521]

[0522] [Synthesis Example 6] Synthesis of A-6

[0523]

[0524]

[0525]

[0526] The same procedure as in Synthesis Example 1 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-6 (9.5 g, yield 72%).

[0527] Mass (theoretical: 807.91, measured: 807 g / mol)

[0528]

[0529] [Synthesis Example 7] Synthesis of B-1

[0530]

[0531]

[0532]

[0533] Under a nitrogen stream, DLD-2 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0534] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound B-1 (8.3 g, yield 71%).

[0535] Mass (theoretical: 717.83, measured: 717 g / mol)

[0536]

[0537] [Synthesis Example 8] Synthesis of B-2

[0538]

[0539]

[0540]

[0541] The same procedure as in Synthetic Example 7 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-2 (7.6 g, yield 64%).

[0542] Mass (theoretical: 727.89, measured: 727 g / mol)

[0543]

[0544] [Synthesis Example 9] Synthesis of B-3

[0545]

[0546]

[0547]

[0548] The same procedure as in Synthetic Example 7 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-3 (8.0 g, yield 62%).

[0549] Mass (theoretical: 793.93, measured: 793 g / mol)

[0550]

[0551] [Synthesis Example 10] Synthesis of B-4

[0552]

[0553]

[0554]

[0555] The same procedure as in Synthetic Example 7 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-4 (8.8 g, yield 68%).

[0556] Mass (theoretical: 793.93, measured: 793 g / mol)

[0557]

[0558] [Synthesis Example 11] Synthesis of B-5

[0559]

[0560]

[0561]

[0562] The same procedure as in Synthetic Example 7 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-5 (8.0 g, yield 62%).

[0563] Mass (theoretical: 793.93, measured: 793 g / mol)

[0564]

[0565] [Synthesis Example 12] Synthesis of B-6

[0566]

[0567]

[0568]

[0569]

[0570] *The same procedure as in Synthetic Example 7 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-6 (9.2 g, yield 70%).

[0571] Mass (theoretical: 807.91, measured: 807 g / mol)

[0572]

[0573] [Synthesis Example 13] Synthesis of C-1

[0574]

[0575]

[0576]

[0577] Under a nitrogen stream, DLD-3 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0578] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound C-1 (8.1 g, yield 69%).

[0579] Mass (theoretical: 717.83, measured: 717 g / mol)

[0580]

[0581] [Synthesis Example 14] Synthesis of C-2

[0582]

[0583]

[0584]

[0585] The same procedure as in Synthetic Example 13 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-2 (8.1 g, yield 68%).

[0586] Mass (theoretical: 727.89, measured: 727 g / mol)

[0587]

[0588] [Synthesis Example 15] Synthesis of C-3

[0589]

[0590]

[0591]

[0592] The same procedure as in Synthetic Example 13 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-3 (8.6 g, yield 66%).

[0593] Mass (theoretical: 793.93, measured: 793 g / mol)

[0594]

[0595] [Synthesis Example 16] Synthesis of C-4

[0596]

[0597]

[0598]

[0599] The same procedure as in Synthetic Example 13 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-4 (8.2 g, yield 63%).

[0600] Mass (theoretical: 793.93, measured: 793 g / mol)

[0601]

[0602] [Synthesis Example 17] Synthesis of C-5

[0603]

[0604]

[0605]

[0606] The same procedure as in Synthetic Example 13 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-5 (8.8 g, yield 68%).

[0607] Mass (theoretical: 793.93, measured: 793 g / mol)

[0608]

[0609] [Synthesis Example 18] Synthesis of C-6

[0610]

[0611]

[0612]

[0613] The same procedure as in Synthetic Example 13 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-6 (8.6 g, yield 65%).

[0614] Mass (theoretical: 807.91, measured: 807 g / mol)

[0615]

[0616] [Synthesis Example 19] Synthesis of D-1

[0617]

[0618]

[0619]

[0620] Under a nitrogen stream, DLD-4 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0621] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound D-1 (8.3 g, yield 71%).

[0622] Mass (theoretical: 717.83, measured: 717 g / mol)

[0623]

[0624] [Synthesis Example 20] Synthesis of D-2

[0625]

[0626]

[0627]

[0628] The same procedure as in Synthetic Example 19 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-2 (8.3 g, yield 70%).

[0629] Mass (theoretical: 727.89, measured: 727 g / mol)

[0630]

[0631] [Synthesis Example 21] Synthesis of D-3

[0632]

[0633]

[0634]

[0635] The same procedure as in Synthetic Example 19 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-3 (8.8 g, yield 68%).

[0636] Mass (theoretical: 793.93, measured: 793 g / mol)

[0637]

[0638] [Synthesis Example 22] Synthesis of D-4

[0639]

[0640]

[0641]

[0642] The same procedure as in Synthetic Example 19 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-4 (8.7 g, yield 67%).

[0643] Mass (theoretical: 793.93, measured: 793 g / mol)

[0644]

[0645] [Synthesis Example 23] Synthesis of D-5

[0646]

[0647]

[0648]

[0649] The same procedure as in Synthetic Example 19 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-5 (8.4 g, yield 65%).

[0650] Mass (theoretical: 793.93, measured: 793 g / mol)

[0651]

[0652] [Synthesis Example 24] Synthesis of D-6

[0653]

[0654]

[0655]

[0656] The same procedure as in Synthetic Example 19 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-6 (9.4 g, yield 71%).

[0657] Mass (theoretical: 807.91, measured: 807 g / mol)

[0658]

[0659] [Synthesis Example 25] Synthesis of E-1

[0660]

[0661]

[0662]

[0663] Under a nitrogen stream, DLD-5 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0664] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound E-1 (7.6 g, yield 65%).

[0665] Mass (theoretical: 717.83, measured: 717 g / mol)

[0666]

[0667] [Synthesis Example 26] Synthesis of E-2

[0668]

[0669]

[0670]

[0671] The same procedure as in Synthetic Example 25 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-2 (7.7 g, yield 65%).

[0672] Mass (theoretical: 727.89, measured: 727 g / mol)

[0673]

[0674] [Synthesis Example 27] Synthesis of E-3

[0675]

[0676]

[0677]

[0678] The same procedure as in Synthetic Example 25 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-3 (8.2 g, yield 63%).

[0679] Mass (theoretical: 793.93, measured: 793 g / mol)

[0680]

[0681] [Synthesis Example 28] Synthesis of E-4

[0682]

[0683]

[0684]

[0685] The same procedure as in Synthetic Example 25 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-4 (8.8 g, yield 68%).

[0686] Mass (theoretical: 793.93, measured: 793 g / mol)

[0687]

[0688] [Synthesis Example 29] Synthesis of E-5

[0689]

[0690]

[0691]

[0692] The same procedure as in Synthetic Example 25 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-5 (8.9 g, yield 69%).

[0693] Mass (theoretical: 793.93, measured: 793 g / mol)

[0694]

[0695] [Synthesis Example 30] Synthesis of E-6

[0696]

[0697]

[0698]

[0699] The same procedure as in Synthetic Example 25 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-6 (8.3 g, yield 63%).

[0700] Mass (theoretical: 807.91, measured: 807 g / mol)

[0701]

[0702] [Synthesis Example 31] Synthesis of F-1

[0703]

[0704]

[0705]

[0706] Under a nitrogen stream, DLD-6 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0707] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound F-1 (8.3 g, yield 71%).

[0708] Mass (theoretical: 717.83, measured: 717 g / mol)

[0709]

[0710] [Synthesis Example 32] Synthesis of F-2

[0711]

[0712]

[0713]

[0714] The same procedure as in Synthetic Example 31 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-2 (8.6 g, yield 72%).

[0715] Mass (theoretical: 727.89, measured: 727 g / mol)

[0716]

[0717] [Synthesis Example 33] Synthesis of F-3

[0718]

[0719]

[0720]

[0721] The same procedure as in Synthetic Example 31 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-3 (9.1 g, yield 70%).

[0722] Mass (theoretical: 793.93, measured: 793 g / mol)

[0723]

[0724] [Synthesis Example 34] Synthesis of F-4

[0725]

[0726]

[0727]

[0728] The same procedure as in Synthetic Example 31 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-4 (9.5 g, yield 73%).

[0729] Mass (theoretical: 793.93, measured: 793 g / mol)

[0730]

[0731] [Synthesis Example 35] Synthesis of F-5

[0732]

[0733]

[0734]

[0735] The same procedure as in Synthetic Example 31 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-5 (9.7 g, yield 75%).

[0736] Mass (theoretical: 793.93, measured: 793 g / mol)

[0737]

[0738] [Synthesis Example 36] Synthesis of F-6

[0739]

[0740]

[0741]

[0742] The same procedure as in Synthesis Example 31 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-6 (9.2 g, yield 70%).

[0743] Mass (theoretical: 807.91, measured: 807 g / mol)

[0744]

[0745] [Synthesis Example 37] Synthesis of G-1

[0746]

[0747]

[0748]

[0749] Under a nitrogen stream, DLD-7 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0750] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound G-1 (8.0 g, yield 68%).

[0751] Mass (theoretical: 717.83, measured: 717 g / mol)

[0752]

[0753] [Synthesis Example 38] Synthesis of G-2

[0754]

[0755]

[0756]

[0757] The same procedure as in Synthesis Example 37 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-2 (8.2 g, yield 69%).

[0758] Mass (theoretical: 727.89, measured: 727 g / mol)

[0759]

[0760] [Synthesis Example 39] Synthesis of G-3

[0761]

[0762]

[0763]

[0764] The same procedure as in Synthesis Example 37 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-3 (8.3 g, yield 64%).

[0765] Mass (theoretical: 793.93, measured: 793 g / mol)

[0766]

[0767] [Synthesis Example 40] Synthesis of G-4

[0768]

[0769]

[0770]

[0771] The same procedure as in Synthesis Example 37 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-4 (8.8 g, yield 68%).

[0772] Mass (theoretical: 793.93, measured: 793 g / mol)

[0773]

[0774] [Synthesis Example 41] Synthesis of G-5

[0775]

[0776]

[0777]

[0778] The same procedure as in Synthesis Example 37 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-5 (8.4 g, yield 65%).

[0779] Mass (theoretical: 793.93, measured: 793 g / mol)

[0780]

[0781] [Synthesis Example 42] Synthesis of G-6

[0782]

[0783]

[0784]

[0785] The same procedure as in Synthesis Example 37 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-6 (8.4 g, yield 64%).

[0786] Mass (theoretical: 807.91, measured: 807 g / mol)

[0787]

[0788] [Synthesis Example 43] Synthesis of H-1

[0789]

[0790]

[0791]

[0792] Under a nitrogen stream, DLD-8 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0793] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound H-1 (7.6 g, yield 65%).

[0794] Mass (theoretical: 717.83, measured: 717 g / mol)

[0795]

[0796] [Synthesis Example 44] Synthesis of H-2

[0797]

[0798]

[0799]

[0800] The same procedure as in Synthesis Example 43 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-2 (8.0 g, yield 67%).

[0801] Mass (theoretical: 727.89, measured: 727 g / mol)

[0802]

[0803] [Synthesis Example 45] Synthesis of H-3

[0804]

[0805]

[0806]

[0807] The same procedure as in Synthesis Example 43 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-3 (8.8 g, yield 68%).

[0808] Mass (theoretical: 793.93, measured: 793 g / mol)

[0809]

[0810] [Synthesis Example 46] Synthesis of H-4

[0811]

[0812]

[0813]

[0814] The same procedure as in Synthesis Example 43 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-4 (8.2 g, yield 63%).

[0815] Mass (theoretical: 793.93, measured: 793 g / mol)

[0816]

[0817] [Synthesis Example 47] Synthesis of H-5

[0818]

[0819]

[0820]

[0821] The same procedure as in Synthesis Example 43 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-5 (8.6 g, yield 66%).

[0822] Mass (theoretical: 793.93, measured: 793 g / mol)

[0823]

[0824] [Synthesis Example 48] Synthesis of H-6

[0825]

[0826]

[0827]

[0828] The same procedure as in Synthesis Example 43 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-6 (9.4 g, yield 71%).

[0829] Mass (theoretical: 807.91, measured: 807 g / mol)

[0830]

[0831] [Synthesis Example 49] Synthesis of I-1

[0832]

[0833]

[0834]

[0835] Under a nitrogen stream, DLD-9 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0836] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound I-1 (6.9 g, yield 59%).

[0837] Mass (theoretical: 717.83, measured: 717 g / mol)

[0838]

[0839] [Synthesis Example 50] Synthesis of I-2

[0840]

[0841]

[0842]

[0843] The same procedure as in Synthesis Example 49 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-2 (7.7 g, yield 65%).

[0844] Mass (theoretical: 727.89, measured: 727 g / mol)

[0845]

[0846] [Synthesis Example 51] Synthesis of I-3

[0847]

[0848]

[0849]

[0850] The same procedure as in Synthesis Example 49 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-3 (8.6 g, yield 66%).

[0851] Mass (theoretical: 793.93, measured: 793 g / mol)

[0852]

[0853] [Synthesis Example 52] Synthesis of I-4

[0854]

[0855]

[0856]

[0857] The same procedure as in Synthesis Example 49 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-4 (8.3 g, yield 64%).

[0858] Mass (theoretical: 793.93, measured: 793 g / mol)

[0859]

[0860] [Synthesis Example 53] Synthesis of I-5

[0861]

[0862]

[0863]

[0864] The same procedure as in Synthesis Example 49 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-5 (8.8 g, yield 68%).

[0865] Mass (theoretical: 793.93, measured: 793 g / mol)

[0866]

[0867] [Synthesis Example 54] Synthesis of I-6

[0868]

[0869]

[0870]

[0871] The same procedure as in Synthesis Example 49 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-6 (8.6 g, yield 65%).

[0872] Mass (theoretical: 807.91, measured: 807 g / mol)

[0873]

[0874] [Synthesis Example 55] Synthesis of J-1

[0875]

[0876]

[0877]

[0878] Under a nitrogen stream, DLD-10 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0879] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound J-1 (7.5 g, yield 64%).

[0880] Mass (theoretical: 717.83, measured: 717 g / mol)

[0881]

[0882] [Synthesis Example 56] Synthesis of J-2

[0883]

[0884]

[0885]

[0886] The same procedure as in Synthetic Example 55 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-2 (8.1 g, yield 68%).

[0887] Mass (theoretical: 727.89, measured: 727 g / mol)

[0888]

[0889] [Synthesis Example 57] Synthesis of J-3

[0890]

[0891]

[0892]

[0893] The same procedure as in Synthesis Example 55 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-3 (8.7 g, yield 67%).

[0894] Mass (theoretical: 793.93, measured: 793 g / mol)

[0895]

[0896] [Synthesis Example 58] Synthesis of J-4

[0897]

[0898]

[0899]

[0900] The same procedure as in Synthesis Example 55 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-4 (8.0 g, yield 62%).

[0901] Mass (theoretical: 793.93, measured: 793 g / mol)

[0902]

[0903] [Synthesis Example 59] Synthesis of J-5

[0904]

[0905]

[0906]

[0907] The same procedure as in Synthesis Example 55 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-5 (8.4 g, yield 65%).

[0908] Mass (theoretical: 793.93, measured: 793 g / mol)

[0909]

[0910] [Synthesis Example 60] Synthesis of J-6

[0911]

[0912]

[0913]

[0914] The same procedure as in Synthesis Example 55 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-6 (8.7 g, yield 66%).

[0915] Mass (theoretical: 807.91, measured: 807 g / mol)

[0916]

[0917] [Synthesis Example 61] Synthesis of K-1

[0918]

[0919]

[0920]

[0921] Under a nitrogen stream, DLD-11 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0922] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound K-1 (8.1 g, yield 69%).

[0923] Mass (theoretical: 717.83, measured: 717 g / mol)

[0924]

[0925] [Synthesis Example 62] Synthesis of K-2

[0926]

[0927]

[0928]

[0929] The same procedure as in Synthesis Example 61 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-2 (7.6 g, yield 64%).

[0930] Mass (theoretical: 727.89, measured: 727 g / mol)

[0931]

[0932] [Synthesis Example 63] Synthesis of K-3

[0933]

[0934]

[0935]

[0936] The same procedure as in Synthesis Example 61 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-3 (9.2 g, yield 71%).

[0937] Mass (theoretical: 793.93, measured: 793 g / mol)

[0938]

[0939] [Synthesis Example 64] Synthesis of K-4

[0940]

[0941]

[0942]

[0943] The same procedure as in Synthesis Example 61 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-4 (8.8 g, yield 68%).

[0944] Mass (theoretical: 793.93, measured: 793 g / mol)

[0945]

[0946] [Synthesis Example 65] Synthesis of K-5

[0947]

[0948]

[0949]

[0950] The same procedure as in Synthesis Example 61 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-5 (9.1 g, yield 70%).

[0951] Mass (theoretical: 793.93, measured: 793 g / mol)

[0952]

[0953] [Synthesis Example 66] Synthesis of K-6

[0954]

[0955]

[0956]

[0957] The same procedure as in Synthesis Example 61 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-6 (9.4 g, yield 71%).

[0958] Mass (theoretical: 807.91, measured: 807 g / mol)

[0959]

[0960] [Synthesis Example 67] Synthesis of L-1

[0961]

[0962]

[0963]

[0964] Under a nitrogen stream, DLD-12 (10.0 g, 16.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0965] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound L-1 (8.3 g, yield 71%).

[0966] Mass (theoretical: 717.83, measured: 717 g / mol)

[0967]

[0968] [Synthesis Example 68] Synthesis of L-2

[0969]

[0970]

[0971]

[0972] The same procedure as in Synthesis Example 67 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.4 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-2 (8.3 g, yield 70%).

[0973] Mass (theoretical: 727.89, measured: 727 g / mol)

[0974]

[0975] [Synthesis Example 69] Synthesis of L-3

[0976]

[0977]

[0978]

[0979] The same procedure as in Synthesis Example 67 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-3 (9.5 g, yield 73%).

[0980] Mass (theoretical: 793.93, measured: 793 g / mol)

[0981]

[0982] [Synthesis Example 70] Synthesis of L-4

[0983]

[0984]

[0985]

[0986] The same procedure as in Synthesis Example 67 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-4 (8.6 g, yield 66%).

[0987] Mass (theoretical: 793.93, measured: 793 g / mol)

[0988]

[0989] [Synthesis Example 71] Synthesis of L-5

[0990]

[0991]

[0992]

[0993] The same procedure as in Synthesis Example 67 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-5 (8.3 g, yield 64%).

[0994] Mass (theoretical: 793.93, measured: 793 g / mol)

[0995]

[0996] [Synthesis Example 72] Synthesis of L-6

[0997]

[0998]

[0999]

[1000] The same procedure as in Synthesis Example 67 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-6 (9.0 g, yield 68%).

[1001] Mass (theoretical: 807.91, measured: 807 g / mol)

[1002]

[1003] [Synthesis Example 73] Synthesis of M-1

[1004]

[1005]

[1006]

[1007] Under a nitrogen stream, DLD-13 (10.0 g, 15.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1008] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain the target compound M-1 (6.5 g, yield 56%).

[1009] Mass (theoretical: 733.89, measured: 733 g / mol)

[1010]

[1011] [Synthesis Example 74] Synthesis of M-2

[1012]

[1013]

[1014]

[1015] The same procedure as in Synthesis Example 73 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-2 (6.9 g, yield 58%).

[1016] Mass (theoretical: 743.95, measured: 743 g / mol)

[1017]

[1018] [Synthesis Example 75] Synthesis of M-3

[1019]

[1020]

[1021]

[1022] The same procedure as in Synthesis Example 73 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-3 (8.0 g, yield 62%).

[1023] Mass (theoretical: 809.99, measured: 810 g / mol)

[1024]

[1025] [Synthesis Example 76] Synthesis of M-4

[1026]

[1027]

[1028]

[1029] The same procedure as in Synthesis Example 73 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-4 (8.2 g, yield 64%).

[1030] Mass (theoretical: 809.99, measured: 810 g / mol)

[1031]

[1032] [Synthesis Example 77] Synthesis of M-5

[1033]

[1034]

[1035]

[1036] The same procedure as in Synthesis Example 73 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-5 (7.6 g, yield 59%).

[1037] Mass (theoretical: 809.99, measured: 810 g / mol)

[1038]

[1039] [Synthesis Example 78] Synthesis of M-6

[1040]

[1041]

[1042]

[1043] The same procedure as in Synthesis Example 73 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-6 (6.9 g, yield 53%).

[1044] Mass (theoretical: 823.97, measured: 824 g / mol)

[1045]

[1046] [Synthesis Example 79] Synthesis of N-1

[1047]

[1048]

[1049]

[1050] Under a nitrogen stream, DLD-14 (10.0 g, 15.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1051] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 6:1 (v / v)) to obtain the target compound N-1 (7.1 g, yield 61%).

[1052] Mass (theoretical: 733.89, measured: 733 g / mol)

[1053]

[1054] [Synthesis Example 80] Synthesis of N-2

[1055]

[1056]

[1057]

[1058] The same procedure as in Synthesis Example 79 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-2 (7.0 g, yield 59%).

[1059] Mass (theoretical: 743.95, measured: 743 g / mol)

[1060]

[1061] [Synthesis Example 81] Synthesis of N-3

[1062]

[1063]

[1064]

[1065] The same procedure as in Synthesis Example 79 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-3 (7.1 g, yield 55%).

[1066] Mass (theoretical: 809.99, measured: 810 g / mol)

[1067]

[1068] [Synthesis Example 82] Synthesis of N-4

[1069]

[1070]

[1071]

[1072] The same procedure as in Synthesis Example 79 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-4 (7.3 g, yield 57%).

[1073] Mass (theoretical: 809.99, measured: 810 g / mol)

[1074]

[1075] [Synthesis Example 83] Synthesis of N-5

[1076]

[1077]

[1078]

[1079] The same procedure as in Synthesis Example 79 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-5 (7.9 g, yield 61%).

[1080] Mass (theoretical: 809.99, measured: 810 g / mol)

[1081]

[1082] [Synthesis Example 84] Synthesis of N-6

[1083]

[1084]

[1085]

[1086] The same procedure as in Synthesis Example 79 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-6 (7.2 g, yield 55%).

[1087] Mass (theoretical: 823.97, measured: 824 g / mol)

[1088]

[1089] [Synthesis Example 85] Synthesis of O-1

[1090]

[1091]

[1092]

[1093] Under a nitrogen stream, DLD-15 (10.0 g, 15.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.5 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.3 g, 38.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1094] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain the target compound O-1 (6.0 g, yield 52%).

[1095] Mass (theoretical: 755.02, measured: 755 g / mol)

[1096]

[1097] [Synthesis Example 86] Synthesis of O-2

[1098]

[1099]

[1100]

[1101] The same procedure as in Synthesis Example 85 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.1 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-2 (6.4 g, yield 54%).

[1102] Mass (theoretical: 765.08, measured: 765 g / mol)

[1103]

[1104] [Synthesis Example 87] Synthesis of O-3

[1105]

[1106]

[1107]

[1108] The same procedure as in Synthesis Example 85 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-3 (6.8 g, yield 53%).

[1109] Mass (theoretical: 831.12, measured: 831 g / mol)

[1110]

[1111] [Synthesis Example 88] Synthesis of O-4

[1112]

[1113]

[1114]

[1115] The same procedure as in Synthesis Example 85 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-4 (7.7 g, yield 60%).

[1116] Mass (theoretical: 831.12, measured: 831 g / mol)

[1117]

[1118] [Synthesis Example 89] Synthesis of O-5

[1119]

[1120]

[1121]

[1122] The same procedure as in Synthesis Example 85 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-5 (6.5 g, yield 51%).

[1123] Mass (theoretical: 831.12, measured: 831 g / mol)

[1124]

[1125] [Synthesis Example 90] Synthesis of O-6

[1126]

[1127]

[1128]

[1129] The same procedure as in Synthesis Example 85 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-6 (7.9 g, yield 61%).

[1130] Mass (theoretical: 845.10, measured: 845 g / mol)

[1131]

[1132] [Synthesis Example 91] Synthesis of P-1

[1133]

[1134]

[1135]

[1136] Under a nitrogen stream, DLD-16 (10.0 g, 15.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.5 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.3 g, 38.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1137] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain the target compound P-1 (6.3 g, yield 54%).

[1138] Mass (theoretical: 755.02, measured: 755 g / mol)

[1139]

[1140] [Synthesis Example 92] Synthesis of P-2

[1141]

[1142]

[1143]

[1144] The same procedure as in Synthesis Example 91 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.1 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-2 (6.6 g, yield 56%).

[1145] Mass (theoretical: 765.08, measured: 765 g / mol)

[1146]

[1147] [Synthesis Example 93] Synthesis of P-3

[1148]

[1149]

[1150]

[1151] The same procedure as in Synthesis Example 91 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-3 (7.0 g, yield 55%).

[1152] Mass (theoretical: 831.12, measured: 831 g / mol)

[1153]

[1154] [Synthesis Example 94] Synthesis of P-4

[1155]

[1156]

[1157]

[1158] The same procedure as in Synthesis Example 91 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-4 (6.7 g, yield 52%).

[1159] Mass (theoretical: 831.12, measured: 831 g / mol)

[1160]

[1161] [Synthesis Example 95] Synthesis of P-5

[1162]

[1163]

[1164]

[1165] The same procedure as in Synthesis Example 91 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-5 (8.1 g, yield 63%).

[1166] Mass (theoretical: 831.12, measured: 831 g / mol)

[1167]

[1168] [Synthesis Example 96] Synthesis of P-6

[1169]

[1170]

[1171]

[1172] The same procedure as in Synthesis Example 91 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.6 g, 18.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-6 (9.1 g, yield 70%).

[1173] Mass (theoretical: 845.10, measured: 845 g / mol)

[1174]

[1175] [Synthesis Example 97] Synthesis of Q-1

[1176]

[1177]

[1178]

[1179] Under a nitrogen stream, DLD-17 (10.0 g, 18.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1180] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound Q-1 (7.5 g, yield 64%).

[1181] Mass (theoretical: 738.96, measured: 738 g / mol)

[1182]

[1183] [Synthesis Example 98] Synthesis of Q-2

[1184]

[1185]

[1186]

[1187] The same procedure as in Synthesis Example 97 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-2 (7.4 g, yield 63%).

[1188] Mass (theoretical: 749.02, measured: 749 g / mol)

[1189]

[1190] [Synthesis Example 99] Synthesis of Q-3

[1191]

[1192]

[1193]

[1194] The same procedure as in Synthesis Example 97 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-3 (8.7 g, yield 68%).

[1195] Mass (theoretical: 815.05, measured: 815 g / mol)

[1196]

[1197] [Synthesis Example 100] Synthesis of Q-4

[1198]

[1199]

[1200]

[1201] The same procedure as in Synthesis Example 97 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-4 (9.1 g, yield 71%).

[1202] Mass (theoretical: 815.05, measured: 815 g / mol)

[1203]

[1204] [Synthesis Example 101] Synthesis of Q-5

[1205]

[1206]

[1207]

[1208] The same procedure as in Synthesis Example 97 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-5 (9.0 g, yield 70%).

[1209] Mass (theoretical: 815.05, measured: 815 g / mol)

[1210]

[1211] [Synthesis Example 102] Synthesis of Q-6

[1212]

[1213]

[1214]

[1215] The same procedure as in Synthesis Example 97 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-6 (9.0 g, yield 69%).

[1216] Mass (theoretical: 829.04, measured: 829 g / mol)

[1217]

[1218] [Synthesis Example 103] Synthesis of R-1

[1219]

[1220]

[1221]

[1222] Under a nitrogen stream, DLD-18 (10.0 g, 18.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1223] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound R-1 (6.8 g, yield 58%).

[1224] Mass (theoretical: 738.96, measured: 738 g / mol)

[1225]

[1226] [Synthesis Example 104] Synthesis of R-2

[1227]

[1228]

[1229]

[1230] The same procedure as in Synthesis Example 103 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-2 (7.3 g, yield 62%).

[1231] Mass (theoretical: 749.02, measured: 749 g / mol)

[1232]

[1233] [Synthesis Example 105] Synthesis of R-3

[1234]

[1235]

[1236]

[1237] The same procedure as in Synthesis Example 103 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-3 (8.1 g, yield 63%).

[1238] Mass (theoretical: 815.05, measured: 815 g / mol)

[1239]

[1240] [Synthesis Example 106] Synthesis of R-4

[1241]

[1242]

[1243]

[1244] The same procedure as in Synthesis Example 103 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-4 (8.4 g, yield 65%).

[1245] Mass (theoretical: 815.05, measured: 815 g / mol)

[1246]

[1247] [Synthesis Example 107] Synthesis of R-5

[1248]

[1249]

[1250]

[1251] The same procedure as in Synthesis Example 103 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-5 (8.0 g, yield 62%).

[1252] Mass (theoretical: 815.05, measured: 815 g / mol)

[1253]

[1254] [Synthesis Example 108] Synthesis of R-6

[1255]

[1256]

[1257]

[1258] The same procedure as in Synthesis Example 103 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-6 (8.0 g, yield 61%).

[1259] Mass (theoretical: 829.04, measured: 829 g / mol)

[1260]

[1261] [Synthesis Example 109] Synthesis of S-1

[1262]

[1263]

[1264]

[1265] Under a nitrogen stream, DLD-19 (10.0 g, 18.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1266] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound S-1 (8.2 g, yield 70%).

[1267] Mass (theoretical: 738.96, measured: 738 g / mol)

[1268]

[1269] [Synthesis Example 110] Synthesis of S-2

[1270]

[1271]

[1272]

[1273] The same procedure as in Synthesis Example 109 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-2 (8.0 g, yield 68%).

[1274] Mass (theoretical: 749.02, measured: 749 g / mol)

[1275]

[1276] [Synthesis Example 111] Synthesis of S-3

[1277]

[1278]

[1279]

[1280] The same procedure as in Synthesis Example 109 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-3 (8.6 g, yield 67%).

[1281] Mass (theoretical: 815.05, measured: 815 g / mol)

[1282]

[1283] [Synthesis Example 112] Synthesis of S-4

[1284]

[1285]

[1286]

[1287] The same procedure as in Synthesis Example 109 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-4 (8.5 g, yield 66%).

[1288] Mass (theoretical: 815.05, measured: 815 g / mol)

[1289]

[1290] [Synthesis Example 113] Synthesis of S-5

[1291]

[1292]

[1293]

[1294] The same procedure as in Synthesis Example 109 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-5 (8.2 g, yield 64%).

[1295] Mass (theoretical: 815.05, measured: 815 g / mol)

[1296]

[1297] [Synthesis Example 114] Synthesis of S-6

[1298]

[1299]

[1300]

[1301] The same procedure as in Synthesis Example 109 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-6 (8.2 g, yield 63%).

[1302] Mass (theoretical: 829.04, measured: 829 g / mol)

[1303]

[1304] [Synthesis Example 115] Synthesis of T-1

[1305]

[1306]

[1307]

[1308] Under a nitrogen stream, DLD-20 (10.0 g, 18.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.5 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1309] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound T-1 (8.5 g, yield 73%).

[1310] Mass (theoretical: 738.96, measured: 738 g / mol)

[1311]

[1312] [Synthesis Example 116] Synthesis of T-2

[1313]

[1314]

[1315]

[1316] The same procedure as in Synthesis Example 115 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-2 (83 g, yield 70%).

[1317] Mass (theoretical: 749.02, measured: 749 g / mol)

[1318]

[1319] [Synthesis Example 117] Synthesis of T-3

[1320]

[1321]

[1322]

[1323] The same procedure as in Synthesis Example 115 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-3 (9.3 g, yield 72%).

[1324] Mass (theoretical: 815.05, measured: 815 g / mol)

[1325]

[1326] [Synthesis Example 118] Synthesis of T-4

[1327]

[1328]

[1329]

[1330] The same procedure as in Synthesis Example 115 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-4 (9.0 g, yield 70%).

[1331] Mass (theoretical: 815.05, measured: 815 g / mol)

[1332]

[1333] [Synthesis Example 119] Synthesis of T-5

[1334]

[1335]

[1336]

[1337] The same procedure as in Synthesis Example 115 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.5 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-5 (9.5 g, yield 74%).

[1338] Mass (theoretical: 815.05, measured: 815 g / mol)

[1339]

[1340] [Synthesis Example 120] Synthesis of T-6

[1341]

[1342]

[1343] The same procedure as in Synthesis Example 115 was followed except that 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.8 g, 18.9 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-6 (9.3 g, yield 71%).

[1344] Mass (theoretical: 829.04, measured: 829 g / mol)

[1345]

[1346] [Synthesis Example 121] Synthesis of Compound U-1

[1347]

[1348] Under a nitrogen stream, compound DLD-21 (10.0 g, 15.5 mmol) obtained in Preparation Example 21, 2-chloro-4,6-diphenylpyrimidine (5.0 g, 18.6 mmol), Pd(PPh3)4 (0.90 g, 0.78 mmol), K2CO3 (5.4 g, 38.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[1349] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound U-1 (8.2 g, yield 71%).

[1350] Mass (theoretical: 748.96, measured: 748 g / mol)

[1351]

[1352] [Synthesis Example 122] Synthesis of Compound U-2

[1353]

[1354] The same procedure as in Synthesis Example 121 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.2 g, 18.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 121, to obtain the target compound U-2 (8.0 g, yield 68%).

[1355] Mass (theoretical: 760.01, measured: 760 g / mol)

[1356]

[1357] [Synthesis Example 123] Synthesis of compound U-3

[1358]

[1359] Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (6.4 g, 18.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 121, the same procedure as in Synthesis Example 121 was performed to obtain the target compound U-3 (7.9 g, yield 62%).

[1360] Mass (theoretical: 825.06, measured: 825 g / mol)

[1361]

[1362] [Synthesis Example 124] Synthesis of compound U-4

[1363]

[1364] Except that 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine (6.4 g, 18.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 121, the same procedure as in Synthesis Example 121 was performed to obtain the target compound U-4 (9.0 g, yield 70%).

[1365] Mass (theoretical: 825.06, measured: 825 g / mol)

[1366]

[1367] [Synthesis Example 125] Synthesis of compound U-5

[1368]

[1369] The same procedure as in Synthesis Example 121 was followed, except that 4-chloro-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (6.6 g, 18.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 121, to obtain the target compound U-5 (9.2 g, yield 71%).

[1370] Mass (theoretical: 839.04, measured: 839 g / mol)

[1371]

[1372] [Synthesis Example 126] Synthesis of compound U-6

[1373]

[1374] The same procedure as in Synthesis Example 121 was followed, except that 4-chloro-2-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)pyrimidine (8.1 g, 18.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 121, to obtain the target compound U-6 (9.8 g, yield 69%).

[1375] Mass (theoretical: 915.14, measured: 915 g / mol)

[1376]

[1377] [Synthesis Example 127] Synthesis of Compound V-1

[1378]

[1379] Under a nitrogen stream, compound DLD-22 (10.0 g, 15.7 mmol) obtained in Preparation Example 22, 2-chloro-4,6-diphenylpyrimidine (5.0 g, 18.8 mmol), Pd(PPh3)4 (0.90 g, 0.78 mmol), K2CO3 (5.4 g, 39.1 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[1380] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound V-1 (7.6 g, yield 65%).

[1381] Mass (theoretical: 742.92, measured: 742 g / mol)

[1382]

[1383] [Synthesis Example 128] Synthesis of Compound V-2

[1384]

[1385] The same procedure as in Synthesis Example 127 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.2 g, 18.8 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 127, to obtain the target compound V-2 (7.8 g, yield 66%).

[1386] Mass (theoretical: 753.97, measured: 753 g / mol)

[1387]

[1388] [Synthesis Example 129] Synthesis of Compound V-3

[1389]

[1390] The same procedure as in Synthesis Example 127 was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (6.4 g, 18.8 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 127, to obtain the target compound V-3 (8.2 g, yield 64%).

[1391] Mass (theoretical: 819.02, measured: 819 g / mol)

[1392]

[1393] [Synthesis Example 130] Synthesis of Compound V-4

[1394]

[1395] The same procedure as in Synthesis Example 127 was followed, except that 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine (6.4 g, 18.8 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine, to obtain the target compound V-4 (8.7 g, yield 68%).

[1396] Mass (theoretical: 819.02, measured: 819 g / mol)

[1397]

[1398] [Synthesis Example 131] Synthesis of Compound V-5

[1399]

[1400] The same procedure as in Synthesis Example 127 was followed, except that 4-chloro-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (6.7 g, 18.8 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine, to obtain the target compound V-5 (9.0 g, yield 69%).

[1401] Mass (theoretical: 833.00, measured: 833 g / mol)

[1402]

[1403] [Synthesis Example 132] Synthesis of Compound V-6

[1404]

[1405] Except that 4-chloro-2-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)pyrimidine (8.1 g, 18.8 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 127, the same procedure as in Synthesis Example 127 was performed to obtain the target compound V-6 (9.3 g, yield 65%).

[1406] Mass (theoretical: 909.10, measured: 909 g / mol)

[1407]

[1408] [Synthesis Example 133] Synthesis of Compound W-1

[1409]

[1410] Under a nitrogen stream, compound DLD-23 (10.0 g, 16.4 mmol) obtained in Preparation Example 23, 2-chloro-4,6-diphenylpyrimidine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.94 g, 0.82 mmol), K2CO3 (5.6 g, 41.0 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[1411] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound W-1 (8.0 g, yield 68%).

[1412] Mass (theoretical: 715.86, measured: 715 g / mol)

[1413]

[1414] [Synthesis Example 134] Synthesis of Compound W-2

[1415]

[1416] The same procedure as in Synthesis Example 133 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.5 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 133, to obtain the target compound W-2 (8.0 g, yield 67%).

[1417] Mass (theoretical: 726.91, measured: 726 g / mol)

[1418]

[1419] [Synthesis Example 135] Synthesis of Compound W-3

[1420]

[1421] The same procedure as in Synthesis Example 133 was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 133, to obtain the target compound W-3 ​​(8.5 g, yield 66%).

[1422] Mass (theoretical: 791.95, measured: 791 g / mol)

[1423]

[1424] [Synthesis Example 136] Synthesis of compound W-4

[1425]

[1426] The same procedure as in Synthesis Example 133 was followed, except that 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 133, to obtain the target compound W-4 (8.8 g, yield 68%).

[1427] Mass (theoretical: 791.95, measured: 791 g / mol)

[1428]

[1429] [Synthesis Example 137] Synthesis of compound W-5

[1430]

[1431] The same procedure as in Synthesis Example 133 was followed, except that 4-chloro-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (7.0 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 133, to obtain the target compound W-5 (9.5 g, yield 72%).

[1432] Mass (theoretical: 805.94, measured: 805 g / mol)

[1433]

[1434] [Synthesis Example 138] Synthesis of compound W-6

[1435]

[1436] Except that 4-chloro-2-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)pyrimidine (8.5 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 133, the same procedure as in Synthesis Example 133 was performed to obtain the target compound W-6 (9.5 g, yield 66%).

[1437] Mass (theoretical: 882.04, measured: 882 g / mol)

[1438]

[1439] [Synthesis Example 139] Synthesis of Compound X-1

[1440]

[1441] Under a nitrogen stream, compound DLD-24 (10.0 g, 15.9 mmol) obtained in Preparation Example 24, 2-chloro-4,6-diphenylpyrimidine (5.1 g, 19.1 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), K2CO3 (5.5 g, 39.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[1442] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound X-1 (8.3 g, yield 71%).

[1443] Mass (theoretical: 732.90, measured: 732 g / mol)

[1444]

[1445] [Synthesis Example 140] Synthesis of Compound X-2

[1446]

[1447] The same procedure as in Synthesis Example 139 was followed, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (5.3 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 139, to obtain the target compound X-2 (8.5 g, yield 72%).

[1448] Mass (theoretical: 743.95, measured: 743 g / mol)

[1449]

[1450] [Synthesis Example 141] Synthesis of Compound X-3

[1451]

[1452] Except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (6.5 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 139, the same procedure as in Synthesis Example 139 was performed to obtain the target compound X-3 (9.0 g, yield 70%).

[1453] Mass (theoretical: 809.00, measured: 809 g / mol)

[1454]

[1455] [Synthesis Example 142] Synthesis of Compound X-4

[1456]

[1457] Except that 4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine (6.5 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 139, the same procedure as in Synthesis Example 139 was performed to obtain the target compound X-4 (9.3 g, yield 72%).

[1458] Mass (theoretical: 809.00, measured: 809 g / mol)

[1459]

[1460] [Synthesis Example 143] Synthesis of Compound X-5

[1461]

[1462] Except that 4-chloro-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine (6.8 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 139, the same procedure as in Synthesis Example 139 was performed to obtain the target compound X-5 (9.6 g, yield 73%).

[1463] Mass (theoretical: 822.98, measured: 822 g / mol)

[1464]

[1465] [Synthesis Example 144] Synthesis of Compound X-6

[1466]

[1467] Except that 4-chloro-2-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)pyrimidine (8.3 g, 19.1 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 139, the same procedure as in Synthesis Example 139 was performed to obtain the target compound X-6 (10.2 g, yield 71%).

[1468] Mass (theoretical: 899.08, measured: 899 g / mol)

[1469]

[1470] [Synthesis Example 145] Synthesis of Compound Y-1

[1471]

[1472] Under a nitrogen stream, compound DLD-1 (10.0 g, 16.3 mmol) obtained in Preparation Example 1, 2-chloro-4,6-diphenylpyrimidine (5.2 g, 19.6 mmol), Pd(PPh3)4 (0.94 g, 0.82 mmol), K2CO3 (5.6 g, 40.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[1473] After the reaction was completed, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound Y-1 (8.0 g, yield 68%).

[1474] Mass (theoretical: 716.84, measured: 716 g / mol)

[1475]

[1476] [Synthesis Example 146] Synthesis of Compound Y-2

[1477]

[1478] The same procedure as in Synthesis Example 145 was followed, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 145, to obtain the target compound Y-2 (8.4 g, yield 65%).

[1479] Mass (theoretical: 792.94, measured: 792 g / mol)

[1480]

[1481] [Synthesis Example 147] Synthesis of Z-1

[1482]

[1483] Under a nitrogen stream, DLD-18 (10.0 g, 15.8 mmol), 2-chloro-4,6-diphenylpyrimidine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.4 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1484] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the resultant was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound Z-1 (8.4 g, yield 72%).

[1485] Mass (theoretical: 737.97, measured: 737 g / mol)

[1486]

[1487] [Synthesis Example 148] Synthesis of Z-2

[1488]

[1489]

[1490] Under a nitrogen stream, DLD-18 (10.0 g, 15.8 mmol), 2-chloro-4,6-diphenylpyrimidine (5.1 g, 18.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), K2CO3 (5.5 g, 39.4 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 5 hours.

[1491] After the reaction was completed, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain the target compound Z-2 (8.6 g, yield 74%).

[1492] Mass (theoretical: 737.97, measured: 737 g / mol)

[1493]

[1494] [Example 1] Fabrication of a green organic EL device

[1495] After the compound A-1 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, a green organic EL device was manufactured according to the following process.

[1496] First, a glass substrate coated with a 1500 A (Angstrom) thick thin film of ITO (Indium tin oxide) was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[1497] On the ITO transparent electrode prepared in this way, an organic EL device was manufactured by stacking HT + 2% PA (100 A) / HT (1200 A) / HA (300 A) / 60% compound A-1 + 30% compound HPGH + 10% Ir(ppy)3(400 A) / EA (50 A) / ET + LiQ (300 A_1:1) / LiF (10 A) / Al (1000 A) in that order. At this time, the structures of HT, HA, PA, HPGH, Ir(ppy)3, EA, and ET used are as follows.

[1498]

[1499]

[1500] [Example 2] ~ [Example 148] - Manufacture of green organic EL device

[1501] A green organic EL device was manufactured in the same manner as in Example 1, except that Compounds A-2 to Z-2 described in Table 2 were used instead of Compound A-1, which was used as host 1 among the luminescent host materials when forming the luminescent layer in Example 1.

[1502]

[1503] [Comparative Example 1] ~ [Comparative Example 8] Fabrication of a green organic EL device

[1504] A green organic EL device was manufactured using the same process as in Example 1, except that ET-1 to ET-8 were used instead of compound A-1 as a light-emitting host material when forming the light-emitting layer in Example 1. The structures of ET-1 to ET-8 used are as follows.

[1505]

[1506]

[1507] [Evaluation Example 1]

[1508] For the green organic EL devices manufactured in Examples 1 to 120 and Comparative Examples 1 to 4, the driving voltage, current efficiency, luminescence (EL) peak, and lifespan at a current density of (10) mA / cm2 were measured, and the results are shown in Table 1 below.

[1509] Sample host driving voltage EL peak current efficiency life (V) (nm) (cd / A) (hr, T 97) Example 1A-13.6651866.4381 Example 2A-23.8951564.1388 Example 3A-33.9851866.4380 Example 4A-43.7151862.1384 Example 5A-53.7551563.4381 Example 6A-63.6551864.3381 Example 7B-13.5251768.8395 Example 8B-23.5651568.8391 Example 9B-33.5151868.9390 Example 10B-43.5551868.4393 Example 11B-53.5651868.2393 Example 12B-63.5451562.4395 Example 13C-13.7151865.5393 Example 14C-23.7551867.2391 Example 15C-33.6551868.1401 Example 16C-43.7451766.4400 Example 17C-53.6651564.1403 Example 18C-63.6151566.4391 Example 19D-13.6451862.1390 ​​Example 20D-23.8451863.4393 Example 21D-33.6751564.3381 Example 22D-43.6851867.8384 Example 23D-53.7151865.1381 Example 24D-63.6651563.4388 Example 25E-13.5551869.1392 Example 26E-23.5651869.6396 Example 27E-33.5151869.4399 Example 28E-43.5651768.9392 Example 29E-53.5451568.7391 Example 30E-63.5251569.1395 Example 31F-13.6651861.9381 Example 32F-23.8951862.7384 Example 33F-33.9851765.3384 Example 34F-43.6651562.4381 Example 35F-53.8951863.4371 Example 36F-63.9851564.2379 Example 37G-13.7151464.3381 Example 38G-23.6751563.2388 Example 39G-33.6851866.3391 Example 40G-43.7151964.2392 Example 41G-53.6651163.4391 Example 42G-63.9151561.2390 Example 43H-13.9251565.5393 Example 44H-23.9151867.2392 Example 45H-33.8251168.1392 Example 46H-43.6651466.4385 Example 47H-53.6151564.1380 Example 48H-63.8451566.4384 Example 49I-13.5851362.1399 Example 50I-23.5451863.4393 Example 51I-33.5351568.6391 Example 52I-43.5851868.1401 Example 53I-53.5951868.4400 Example 54I-63.5251768.8403 Example 55J-13.5551568.9391 Example 56J-23.5151568.1390 ​​Example 57J-33.6651866.3393 Example 58J-43.8951863.1392 Example 59J-53.9851161.9384 Example 60J-63.6651462.7399 Example 61K-13.8951565.3393 Example 62K-23.9851562.4391 Example 63K-33.7151863.4401 Example 64K-43.7551164.2400 Example 65K-53.5151464.3403 Example 66K-63.5251563.2391 Example 67L-13.5551566.3390 Example 68L-23.5351868.7390 Example 69L-33.5251368.3393 Example 70L-43.5151868.2392 Example 71L-53.5751568.1392 Example 72L-63.5851868.2390 Example 73M-13.7151765.1384 Example 74M-23.6651763.4381 Example 75M-33.9151564.4375 Example 76M-43.6751862.2379 Example 77M-53.6851762.8381 Example 78M-63.7151865.3374 Example 79N-13.6651766.3385 Example 80N-23.9151563.1380 Example 81N-33.9251361.9384 Example 82N-43.9151462.7382 Example 83N-53.8251865.3385 Example 84N-63.8851162.4377 Example 85O-13.6551469.1425 Example 86O-23.7451570.3435 Example 87O-33.7451569.3422 Example 88O-43.6551869.9415 Example 89O-53.7551368.4463 Example 90O-63.5651868.6422 Example 91P-13.7751568.7421 Example 92P-23.7151868.2468 Example 93P-33.6651767.9430 Example 94P-43.5651768.9441 Example 95P-53.6451569.9455 Example 96P-63.6451869.4425 Example 97Q-13.6851869.6451 Example 98Q-23.6651769.5442 Example 99Q-33.6751567.8443 Example 100Q-43.6551569.1446 Example 101Q-53.7151869.8449 Example 102Q-63.7551170.5441 Example 103R-13.6551470.6452 Example 104R-23.7451570.4462 Example 105R-33.6651570.1451 Example 106R-43.6151869.9474 Example 107R-53.6251369.9470 Example 108R-63.6551868.9460 Example 109S-13.7451568.8462 Example 110S-23.6551870.2463 Example 111S-33.7551770.6422 Example 112S-43.5451770.4423 Example 113S-53.5451569.4463 Example 114S-63.7151869.3422 Example 115T-13.7551769.6421 Example 116T-23.6551870.2436 Example 117T-33.7451770.3435 Example 118T-43.6551569.9415 Example 119T-53.7451368.8432 Example 120T-63.6551470.3444 Example 121U-13.5451465.4391 Example 122U-23.5651665.9401 Example 123U-33.6151465.8395 Example 124U-43.7251366.2388 Example 125U-53.4851567.1387 Example 126U-63.4951766.6379 Example 127V-13.5251665.3391 Example 128V-23.5551564.8411 Example 129V-33.6451464.3401 Example 130V-43.5151664.7399 Example 131V-53.5251665.7395 Example 132V-63.5351465.6392 Example 133W-13.3851765.6386 Example 134W-23.6351668.2405 Example 135W-33.7051567.0395 Example 136W-43.5151463.9382 Example 137W-53.5651663.5374 Example 138W-63.5651563.7371 Example 139X-13.4751463.4370 Example 140X-23.5251763.3386Example 141X-33.8151664.7391Example 142X-43.8251465.4395Example 143X-53.8051565.5376Example 144X-63.7551568.2404Example 145Y-13.6451772.1389Example 146Y-23.6351670.4394Example 147Z-13.6651672.3420Example 148Z-23.6551570.6431Comparative Example 1ET-15.0151444.3301Comparative Example 2ET-24.9851542.1298Comparative example 3ET-34.8151543.4299Comparative example 4ET-45.2351539.4287Comparative example 5ET-54.8951241.2322Comparative example 6ET-65.0151540.4315Comparative example 7ET-75.0251446.2280Comparative example 8ET-84.7251644.4311.

[1510] As shown in Table 1 above, when the compounds (A-1 to Z-2) according to the present invention were used as a light-emitting layer of a green organic EL device (Example 1-148), ET-1 in which R1 of the compound 1 is hydrogen; ET-2 and ET-4 in which a single bond exists between the first dibenzo moiety and the second dibenzo moiety without a linker; ET-3 in which a linker exists between the triazine and the second dibenzo moiety; ET-5 in which an aryl group is substituted on the inside of the dibenzo moiety; ET-7 in which a dimethylfluorene group is applied instead of a dibenzo (or dibenzothiophene) group; ET-8 in which no aryl group is separately substituted; Compared to the green organic EL devices (Comparative Examples 1 to 8) using , it can be seen that they exhibit superior performance in terms of luminous efficiency, driving voltage, and lifespan characteristics.

[1511] This is because, when dibenzofuran (or dibenzothiophene) containing Y1 in Chemical Formula 1, R1 with aryl or heteroaryl introduced, and L1 with arylene or heteroarylene introduced are deposited as materials, an appropriate level of intermolecular steric effect is provided to prevent stacking between the deposited materials. In view of the above, it was confirmed that R1 and L1 with aryl or heteroaryl introduced can increase stability against injected electrons by being included in the compound of the present invention, and are more advantageous to the overall characteristics of the device.

[1512] From the above description, those skilled in the art will understand that the present invention can be implemented in other specific forms without altering its technical spirit or essential characteristics. In this regard, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. The scope of the present invention should be interpreted as encompassing all changes or modifications derived from the meaning and scope of the following claims and their equivalent concepts, rather than the detailed description above.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 Inland X 3 are identical or different from each other, and each is independently N or CR, but X 1 Inland X 3 At least one of them is N, Y 1 and Y 2 are identical or different from each other, and are each independently O, S, Se, N(Ar 3 ), C(Ar 4 )(Ar 5 ) and Si(Ar 6 )(Ar 7 ) is selected from the group consisting of, L 1 and L 2 are identical or different from each other, and each is independently C 6 ~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, Ar 1 Inland Ar 7 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 6 ~C 40 Aryl group of, heteroaryl group having 5 to 40 nuclear atoms, C 6 ~C 40 Aryloxy group of C 1 ~C 40 Alkyloxy group of C 6 ~C 40 Arylamine group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 1 ~C 40 Alkylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 40 Aryl boron group, C 6 ~C 40 Arylphosphine group of C 6 ~C 40 Arylphosphine oxide group and C 6 ~C 40 is selected from the group consisting of arylsilyl groups, or these can combine with any adjacent groups to form a condensed ring, m is an integer from 1 to 3, o is an integer from 0 to 2, Dn is an integer greater than or equal to 0, which represents the number of deuterium atoms. R 1 Silver halogen group, cyano group, nitro group, amino group, hydroxyl group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 6 ~C 60 Arylphosphine group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 can be selected from the group consisting of arylamine groups, Above Ar 1 Inland Ar 7 ; and R 1 The alkyl group, alkenyl group, alkynyl group and aryl group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 Cycloalkyl group of and C 6 ~C 60 It may be substituted with one or more substituents selected from the group consisting of aryl groups, and when there are multiple substituents, they may be the same or different from each other.

2. In paragraph 1, Above R 1 Silver C 6 ~C 60 A compound which is an aryl group or a heteroaryl group having 5 to 60 nuclear atoms.

3. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 5: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the chemical formulas 2 to 5 above, X 1 , X 2 , X 3 , Y 1 , Y 2 , L 1 , L 2 , Ar 1 , Ar 2 , m, o, Dn, R 1 are as defined in Article 1, respectively.

4. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 6 to 9: [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] In the chemical formulas 6 to 9 above, X 1 , X 2 , X 3 , Y 1 , Y 2 , L 1 , L 2 , Ar 1 , Ar 2 , m, o, Dn, R 1 are as defined in Article 1, respectively.

5. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 10 to 13: [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] In the above chemical formulas 10 to 13, X 1 , X 2 , X 3 , Y 1 , Y 2 , L 1 , L 2 , Ar 1 , Ar 2 , m, o, Dn, R 1 are as defined in Article 1, respectively.

6. In paragraph 1, Above X 1 Inland X 3 The compound is one of the following structural formulas: In the above formula, * is (L) of the chemical formula 1 above 2 ) o It means the part that is connected to, Ar 1 , Ar 2 are as defined in Article 1, respectively.

7. In paragraph 1, L 1 and / or L 2 is a compound which is a linker selected from the structural formulas below:

8. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of the following chemical formulas A-1 to Z-2.

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound that is a host material of a light-emitting layer.

10. Containing an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, An organic electroluminescent device, wherein at least one of the organic layers of the above one or more layers comprises a compound represented by the chemical formula 1 as described in any one of claims 1 to 9.

11. In paragraph 10, The organic layer of the above one or more layers includes at least one selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer. An organic electroluminescent device, wherein the light-emitting layer comprises a compound represented by the chemical formula 1 as a host.

12. In paragraph 11, An organic electroluminescent device, wherein the light-emitting layer further comprises at least one selected from the group consisting of a P-type host material, an N-type host material, a fluorescent light-emitting dopant, and a phosphorescent light-emitting dopant.

Images