Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to: a novel compound exhibiting excellent carrier transport ability, light-emitting ability, and thermal stability; and an organic electroluminescent device comprising same in one or more organic layers, thereby having improved properties of luminous efficiency, driving voltage, lifespan and the like.

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 a novel compound having excellent carrier transport ability, luminescence ability, and heat resistance, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices led to the blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic electroluminescent device with a layered structure divided into functional layers, a hole layer and an emission layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has been made by introducing characteristic organic layers within the device, which has led to the development of specialized materials used for this.

[0004] 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.

[0005] 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. Among the phosphorescent 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, especially those with significant advantages in terms of efficiency enhancement among luminescent materials. To date, CBP has demonstrated excellent properties as a phosphorescent host material.

[0006] However, while conventional luminescent materials offer advantages in terms of luminescence properties, their low glass transition temperatures and poor thermal stability make them unsatisfactory in terms of lifespan in organic electroluminescent devices. Therefore, the development of luminescent materials with superior performance is urgently needed.

[0007] Meanwhile, deuterium naturally occurs at approximately 0.015% abundance. Deuterated compounds rich in deuterium are well known. Deuterated aromatic compounds have been used to study chemical reactions and metabolic pathways, and have also been used as raw materials for pharmaceuticals, agricultural chemicals, functional materials, and analytical tracers. Some deuterated electroluminescent materials have been reported to exhibit improved performance (efficiency, lifetime) compared to non-deuterated isomers (see, e.g., Tong, et al. J. Phys. Chem. C2007, 111, 3490–4). Current methods for synthesizing deuterated compounds may require autolysis to achieve high levels of deuteration. These methods are expensive or time-consuming, making them unsuitable from a cost- and efficiency-related perspective. Therefore, there is a continuing need for improved methods for synthesizing deuterated aromatic compounds.

[0008]

[0009] The present invention has been devised to solve the above-mentioned problems, and more specifically, the technical task of the present invention is to provide a novel compound having excellent carrier transport ability, luminescence ability, heat resistance, etc., and which can be used as an organic layer material of an organic electroluminescent device, specifically, as a host material of a luminescent layer.

[0010] 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.

[0011] Other objects and advantages of the present invention can be more clearly explained by the detailed description of the invention and the claims below.

[0012]

[0013] To achieve the above technical task, the present invention provides a compound represented by the following chemical formula 1.

[0014]

[0015] In the above chemical formula 1,

[0016] X1 to X3 are the same or different from each other, and are each independently CR4 or N, provided that at least one of X1 to X3 is N,

[0017] Y1 and Y2 are the same or different from each other, and are each independently O or S,

[0018] Ar1 to Ar3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 is selected from the group consisting of aryl groups, or these may combine with any adjacent group to form a condensed ring, except that the case where Ar1 is hydrogen is excluded,

[0019] R1 to R4 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 of, and C6~C 60 is selected from the group consisting of aryl groups, or these may combine with any adjacent groups to form a condensed ring,

[0020] o is an integer from 0 to 3,

[0021] p and q are each independently integers from 0 to 5,

[0022] The alkyl group, alkenyl group, alkynyl group, and aryl group of the above Ar1 to Ar3, R1 to R4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40Cycloalkyl 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.

[0023] 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.

[0024] 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 the compound of the above chemical formula 1 as a host, specifically, an N-type host.

[0025]

[0026] 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.

[0027] 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 high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventionally known host materials.

[0028] 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.

[0029] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0030]

[0031] Hereinafter, the present invention will be described in detail.

[0032] Organic compounds

[0033] 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), and to which at least one moiety (e.g., Ar1 to Ar3) that does not contain a heteroatom is introduced.

[0034] Specifically, the compound represented by Chemical Formula 1 according to the present invention is a novel N-type host that essentially includes 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.

[0035] 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.

[0036] Meanwhile, the present inventors have recognized that when a heteroatom (e.g., N, O, S)-containing moiety is introduced as Ar1, Ar2, and Ar3 introduced to a dibenzo moiety and an azine group, the unshared electron pair existing in the heteroatom is used as another migration path of holes that should be transferred through a host, for example, a phosphorescent green host (HPGH), and this causes a loss equivalent to the number of holes transferred through the other migration path when forming an exciton in the light-emitting layer, which inevitably causes a deterioration in the performance of the device. Accordingly, in the present invention, the molecular structure is designed so as not to include a separate heteroatom-containing moiety, except for the heteroatom included in two dibenzo moieties (e.g., Y1 and Y2-containing rings) and one azine group (e.g., X1 to X3-containing rings). Specifically, by introducing a heteroatom-free moiety, such as an aryl group, as Ar1, Ar2, and Ar3 introduced into the dibenzo moiety and the azine group, the stability to injected electrons can be increased, and thus a synergy effect of the overall characteristics of the organic electroluminescent device including the compound of the above chemical formula 1 can be realized (see Table 1 below).

[0037] 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 bond dissociation energy, which lowers 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). Accordingly, when the compound of chemical formula 1 of the present invention is substituted with at least one deuterium (D), the green color purity can be further maximized compared to a compound of the same structure without 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 life characteristics of the device.

[0038] 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.

[0039] 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), and to which at least one moiety (e.g., Ar1 to Ar3) that does not contain a heteroatom is introduced. Here, the compound includes at least three or more heteroatoms (e.g., N, O, S) derived from the two dibenzo moieties and the azine group, and specifically may include 3 to 5.

[0040] Y1 and Y2 included in the above two dibenzo moieties are the same or different, and are each independently O or S. Specifically, Y1 and Y2 may be the same. For example, when Y1 and Y2 are O, the compound of the above chemical formula 1 includes two dibenzofuran groups, and when Y1 and Y2 are S, it includes two dibenzothiophene groups.

[0041] 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). Here, the second dibenzo moiety (e.g., Y2-containing ring) may be positioned between the first dibenzo moiety (e.g., Y1-containing ring) and the azine group (e.g., X1 to X3-containing ring), and may serve as a linker (linker L) connecting them. In this way, when the second dibenzo moiety exists as a linker, it can expand the HOMO region, benefit the HOMO-LUMO distribution, and increase the charge transfer efficiency through appropriate HOMO-LUMO overlap. In addition, it can increase the stability of the molecule. At this time, although not shown in the aforementioned chemical formula 1, a compound in which one or both phenyl rings of the second dibenzo moiety (e.g., the Y2-containing ring) are substituted with at least one substituent known in the art (e.g., the same as the R1-R4 definition part) also falls within the scope of the present invention.

[0042] 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, Ar1 and R1, respectively. Ar1 may be deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 is selected from the group consisting of aryl groups, or these can combine with any adjacent groups to form a condensed ring, provided that the case where Ar1 is a moiety containing hydrogen and a heteroatom (e.g., N, O, S) is each excluded. Specifically, Ar1 is C6~C 40 is an aryl group, more specifically C6~C 20 is an aryl group of Ar1, and all or at least part of the hydrogen contained in the aryl group of Ar1 may be replaced with deuterium (D).

[0043] In addition, R1 can be substituted at least once, and even if multiple R1s are represented as the same, they can be the same or different from each other. For example, multiple R1s are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 are selected from the group consisting of aryl groups, or they can combine with any adjacent group to form a condensed ring. Specifically, multiple R1 are each independently hydrogen, deuterium (D), C1~C 40 alkyl group, and C6~C 40It can be selected from the group consisting of aryl groups. Here, multiple o are the same or different, and can each independently be an integer from 0 to 3. In this case, when o is 0, R1 is hydrogen, and when o is 1 to 3, R1 can have the above-mentioned substituents except hydrogen.

[0044] For example, Ar1 may be embodied by any one of the following structural formulas, but is not limited thereto.

[0045]

[0046] In the above formula,

[0047] * indicates a portion connected to the above chemical formula 1. In addition, although not indicated in the above structural formula, at least one deuterium (D) or a substituent known in the art (e.g., the same as the R1-R4 definition part) may be substituted.

[0048] In the chemical formula 1 according to the present invention, among the two dibenzo moieties (e.g., Y1 to Y2-containing rings), the second dibenzo moiety (e.g., Y2-containing ring) is included as a linker, and specifically, one phenyl ring of the second dibenzo moiety (e.g., Y2-containing ring) is connected to the first dibenzo moiety (e.g., Y1-containing ring), and the other phenyl ring is directly connected to a nitrogen-containing heteroaromatic ring (e.g., azine, X1 to X3-containing ring) having excellent electron transporting properties and EWG characteristics.

[0049] In these second dibenzo moieties (e.g., Y2-containing rings), R1 can be substituted with various substituents. In this case, R1 and o can be defined in the same way as in the first dibenzo moiety (e.g., Y1-containing ring) described above, and therefore, a separate description is omitted.

[0050] The above nitrogen-containing heterocyclic ring (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 C(R4) or N, provided that at least one of X1 to X3 contains N. Specifically, it contains 2 to 3 Ns. By including a heterocyclic ring containing 2 to 3 nitrogens in this way, it exhibits better electron absorption properties, which is advantageous for electron injection and transport.

[0051] Here, R4 is each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 aryl group, or these may be combined with any adjacent group to form a condensed ring, and in this case, when there are multiple R4s, the multiple R4s may be the same or different from each other. Specifically, R4 is hydrogen, deuterium (D), C1~C 40 alkyl group, and C6~C 40 It is preferable to select from the group consisting of aryl groups.

[0052] For example, the nitrogen-containing heterocycle (e.g., X1 to X3-containing ring) can be further specified as one selected from the structural formula below, but is not limited thereto.

[0053]

[0054] In the above formula,

[0055] * indicates a part connected to the above chemical formula 1,

[0056] Ar2, Ar3, R2, R3, p and q are each as defined in chemical formula 1.

[0057] In the above nitrogen-containing heterocycle (e.g., X1~X3-containing ring), Ar2 and Ar3 can be substituted with various substituents. Ar2 and Ar3 can be the same or different from each other, and each independently represent hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 or they can be combined with any adjacent group to form a condensed ring. However, when Ar2 and Ar3 are each a moiety containing a heteroatom (e.g., N, O, S), they are each excluded. Specifically, Ar2 and Ar3 are the same or different from each other, and each independently represent hydrogen, deuterium (D), or C6~C 60 is an aryl group, more specifically C6~C 40 is an aryl group, and all or at least part of the hydrogen contained in the aryl group of Ar2 and Ar3 may be replaced with deuterium (D).

[0058] For example, Ar2 and Ar3 may be the same or different from each other, and may be independently embodied as hydrogen, deuterium (D), or one selected from the following structural formulas. However, the present invention is not limited thereto.

[0059]

[0060] In the above formula,

[0061] * indicates a portion connected to the above chemical formula 1. In addition, although not indicated in the above structural formula, at least one deuterium (D) or a substituent known in the art (e.g., the same as the R1-R4 definition part) may be substituted.

[0062] In addition, the above nitrogen-containing heterocycle (e.g., X1 to X3-containing ring) may include at least one R2 and R3. When there are multiple R2 to R3, they are the same or different, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 alkynyl group of, and C6~C 60 are selected from the group consisting of aryl groups, or they can combine with any adjacent group to form a condensed ring. Specifically, R2 and R3 are each independently hydrogen, deuterium (D), C1~C 40 alkyl group, and C6~C 40 It can be selected from the group consisting of aryl groups. Here, p and q are the same or different, and each independently an integer from 0 to 5, specifically an integer from 0 to 4. In this case, when p is 0, R2 is hydrogen, and when p is 1 to 5, R2 may have the above-mentioned substituent except hydrogen. The same can be applied to q.

[0063] In the chemical formula 1 described above, the alkyl group, alkenyl group, alkynyl group, and aryl group of Ar1 to Ar3, R1 to R4 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to 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.

[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 2 to 5, depending on the type of atoms introduced into Y1 and Y2 among the two dibenzo moieties. However, the present invention is not limited thereto.

[0065] [Chemical Formula 2]

[0066]

[0067] [Chemical Formula 3]

[0068]

[0069] [Chemical Formula 4]

[0070]

[0071] [Chemical Formula 5]

[0072]

[0073] In the above formula,

[0074] X1 to X3, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0075] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 6 to 9, depending on the bonding position of the Y1-containing moiety (e.g., the first dibenzo moiety). However, the present invention is not limited thereto.

[0076] [Chemical Formula 6]

[0077]

[0078] [Chemical Formula 7]

[0079]

[0080] [Chemical Formula 8]

[0081]

[0082] [Chemical Formula 9]

[0083]

[0084] In the above formula,

[0085] X1 to X3, Y1, Y2, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0086] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 10 to 13, depending on the bonding position of the Y2-containing moiety (e.g., the second dibenzo moiety) connected to the Y1-containing moiety (e.g., the first dibenzo moiety). However, the present invention is not limited thereto.

[0087] [Chemical Formula 10]

[0088]

[0089] [Chemical Formula 11]

[0090]

[0091] [Chemical Formula 12]

[0092]

[0093] [Chemical Formula 13]

[0094]

[0095] In the above formula,

[0096] X1 to X3, Y1, Y2, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0097] According to another 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 14 to 17, depending on the bonding position of the Y2-containing moiety (e.g., the second dibenzo moiety) connected to the nitrogen-containing heterocycle (e.g., the X1 to X3-containing ring). However, the present invention is not limited thereto.

[0098] [Chemical Formula 14]

[0099]

[0100] [Chemical Formula 15]

[0101]

[0102] [Chemical Formula 16]

[0103]

[0104] [Chemical Formula 17]

[0105]

[0106] In the above formula,

[0107] X1 to X3, Y1, Y2, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0108] The compounds represented by the above-described chemical formulas 6 to 17 can be further specified by any one of the following chemical formulas 1-1-1 to 4-4-4, but are not limited thereto.

[0109] [Chemical Formula 1-1-1]

[0110]

[0111] [Chemical Formula 1-1-2]

[0112]

[0113] [Chemical Formula 1-1-3]

[0114]

[0115] [Chemical Formula 1-1-4]

[0116]

[0117] [Chemical Formula 2-1-1]

[0118]

[0119] [Chemical Formula 2-1-2]

[0120]

[0121] [Chemical Formula 2-1-3]

[0122]

[0123] [Chemical Formula 2-1-4]

[0124]

[0125] [Chemical Formula 3-1-1]

[0126]

[0127] [Chemical Formula 3-1-2]

[0128]

[0129] [Chemical Formula 3-1-3]

[0130]

[0131] [Chemical Formula 3-1-4]

[0132]

[0133] [Chemical Formula 4-1-1]

[0134]

[0135] [Chemical Formula 4-1-2]

[0136]

[0137] [Chemical Formula 4-1-3]

[0138]

[0139] [Chemical Formula 4-1-4]

[0140]

[0141] [Chemical Formula 1-2-1]

[0142]

[0143] [Chemical Formula 1-2-2]

[0144]

[0145] [Chemical Formula 1-2-3]

[0146]

[0147] [Chemical Formula 1-2-4]

[0148]

[0149] [Chemical Formula 2-2-1]

[0150]

[0151] [Chemical Formula 2-2-2]

[0152]

[0153] [Chemical Formula 2-2-3]

[0154]

[0155] [Chemical Formula 2-2-4]

[0156]

[0157] [Chemical Formula 3-2-1]

[0158]

[0159] [Chemical Formula 3-2-2]

[0160]

[0161] [Chemical Formula 3-2-3]

[0162]

[0163] [Chemical Formula 3-2-4]

[0164]

[0165] [Chemical Formula 4-2-1]

[0166]

[0167] [Chemical Formula 4-2-2]

[0168]

[0169] [Chemical Formula 4-2-3]

[0170]

[0171] [Chemical Formula 4-2-4]

[0172]

[0173] [Chemical Formula 1-3-1]

[0174]

[0175] [Chemical Formula 1-3-2]

[0176]

[0177] [Chemical Formula 1-3-3]

[0178]

[0179] [Chemical Formula 1-3-4]

[0180]

[0181] [Chemical Formula 2-3-1]

[0182]

[0183] [Chemical Formula 2-3-2]

[0184]

[0185] [Chemical Formula 2-3-3]

[0186]

[0187] [Chemical Formula 2-3-4]

[0188]

[0189] [Chemical Formula 3-3-1]

[0190]

[0191] [Chemical Formula 3-3-2]

[0192]

[0193] [Chemical Formula 3-3-3]

[0194]

[0195] [Chemical Formula 3-3-4]

[0196]

[0197] [Chemical Formula 4-3-1]

[0198]

[0199] [Chemical Formula 4-3-2]

[0200]

[0201] [Chemical Formula 4-3-3]

[0202]

[0203] [Chemical Formula 4-3-4]

[0204]

[0205] [Chemical Formula 1-4-1]

[0206]

[0207] [Chemical Formula 1-4-2]

[0208]

[0209] [Chemical Formula 1-4-3]

[0210]

[0211] [Chemical Formula 1-4-4]

[0212]

[0213] [Chemical Formula 2-4-1]

[0214]

[0215] [Chemical Formula 2-4-2]

[0216]

[0217] [Chemical Formula 2-4-3]

[0218]

[0219] [Chemical formula 2-4-4]

[0220]

[0221] [Chemical Formula 3-4-1]

[0222]

[0223] [Chemical Formula 3-4-2]

[0224]

[0225] [Chemical Formula 3-4-3]

[0226]

[0227] [Chemical Formula 3-4-4]

[0228]

[0229] [Chemical Formula 4-4-1]

[0230]

[0231] [Chemical Formula 4-4-2]

[0232]

[0233] [Chemical Formula 4-4-3]

[0234]

[0235] [Chemical formula 4-4-4]

[0236]

[0237] In the above formula,

[0238] X1 to X3, Y1, Y2, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0239] The compounds represented by the above chemical formulas 1-1-1 to 4-4-4 can exhibit an effect of improving the stability of injected electrons compared to conventional N-type host materials, and specifically, the structures represented by chemical formulas 3-3-1 and 4-3-1 may be more preferable. This may be because, as the chemical structure is tilted significantly, the triplet (T1) energy of the material increases, which can exhibit an effect of improving the efficiency characteristics of the material, and also, since the heteroatom is spatially located outside the azine group and does not directly affect the azine group, it is significantly advantageous in terms of the electron injection speed of the light-emitting layer (EML).

[0240] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 18 to 21, depending on the bonding position of Ar1 introduced to the Y1-containing moiety (e.g., the first dibenzo moiety). However, the present invention is not limited thereto.

[0241] [Chemical Formula 18]

[0242]

[0243] [Chemical Formula 19]

[0244]

[0245] [Chemical Formula 20]

[0246]

[0247] [Chemical Formula 21]

[0248]

[0249] In the above formula,

[0250] X1 to X3, Y1, Y2, Ar1 to Ar3, R1 to R3, o, p and q are each as defined in chemical formula 1.

[0251] 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 ZA-4 exemplified below. However, the compound represented by chemical formula 1 of the present invention is not limited to those exemplified below.

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] In the present invention, the “number of nuclear atoms” refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0261] In the present invention, "alkyl" means 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.

[0262] In the present invention, "alkenyl" means 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.

[0263] In the present invention, "alkynyl" means 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.

[0264] 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.

[0265] 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, preferably 1 to 3 carbons, in the ring 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.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] In the present 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 containing O.

[0273] In the present invention, “fused ring” means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0274] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms.

[0275] 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.

[0276]

[0277] Organic electroluminescent devices

[0278] The present invention provides an organic electroluminescent device comprising a compound represented by the above chemical formula 1.

[0279] 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.

[0280] 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.

[0281] 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.

[0282] 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 above 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.

[0283] 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.

[0284] 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.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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.

[0293]

[0294] [Preparation Example 1] Synthesis of DDB-1

[0295] <Step 1> Synthesis of 4,4,5,5-tetramethyl-2-(8-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane

[0296]

[0297] Under a nitrogen stream, 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (100.2 g, 394.6 mmol), Pd2(dba)3 (9.9 g, 10.8 mmol), X-Phos (23.9 g, 50.2 mmol), KOAc (67.6 g, 717.5 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0298] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(8-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (86.3 g, yield 65%).

[0299] Mass (theoretical: 370.26, measured: 370 g / mol)

[0300] <Step 2> Synthesis of 9'-chloro-8-phenyl-4,4'-bidibenzo[b,d]furan

[0301]

[0302] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(8-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (86.3 g, 233.2 mmol), 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol), Pd(PPh3)4 (13.5 g, 11.7 mmol), K2CO3 (80.6 g, 583.0 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0303] 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 = 9:1 (v / v)) to obtain 9'-chloro-8-phenyl-4,4'-bidibenzo[b,d]furan (73.7 g, yield 71%).

[0304] Mass (theoretical: 444.91, measured: 444 g / mol)

[0305] <Step 3> Synthesis of DDB-1

[0306]

[0307] Under a nitrogen stream, 9'-chloro-8-phenyl-4,4'-bidibenzo[b,d]furan (73.7 g, 165.6 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (46.2 g, 182.1 mmol), Pd2(dba)3 (4.5 g, 5.0 mmol), X-Phos (11.1 g, 23.2 mmol), KOAc (31.2 g, 331.1 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0308] After the reaction was completed, the product was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain DDB-1 (55.1 g, yield 62%).

[0309] Mass (theoretical: 536.43, measured: 536 g / mol)

[0310] [Preparation Example 2] Synthesis of DDB-2

[0311] <Step 1-3> Synthesis of DDB-2

[0312]

[0313] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 8-bromo-1-chlorodibenzo[b,d]furan (75.1 g, 266.9 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-2 (55.7 g, final yield 29.0%).

[0314] Mass (theoretical: 536.43, measured: 536 g / mol)

[0315] [Preparation Example 3] Synthesis of DDB-3

[0316] <Step 1-3> Synthesis of DDB-3

[0317]

[0318] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 7-bromo-1-chlorodibenzo[b,d]furan (77.6 g, 275.5 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-3 (58.6 g, final yield 30.4%).

[0319] Mass (theoretical: 536.43, measured: 536 g / mol)

[0320] [Preparation Example 4] Synthesis of DDB-4

[0321] <Step 1-3> Synthesis of DDB-4

[0322]

[0323] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 1-bromo-9-chlorodibenzo[b,d]furan (73.9 g, 262.6 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-4 (45.0 g, final yield 23.4%).

[0324] Mass (theoretical: 536.43, measured: 536 g / mol)

[0325] [Preparation Example 5] Synthesis of DDB-5

[0326] <Step 1> Synthesis of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane

[0327]

[0328] Under a nitrogen stream, 7-chloro-1-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (100.2 g, 394.6 mmol), Pd2(dba)3 (9.9 g, 10.8 mmol), X-Phos (23.9 g, 50.2 mmol), KOAc (67.6 g, 717.5 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0329] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (97.0 g, yield 73%).

[0330] Mass (theoretical: 370.26, measured: 370 g / mol)

[0331] <Step 2> Synthesis of 9'-chloro-9-phenyl-3,4'-bidibenzo[b,d]furan

[0332]

[0333] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (97.0 g, 261.9 mmol), 6-bromo-1-chlorodibenzo[b,d]furan (88.5 g, 314.3 mmol), Pd(PPh3)4 (15.1 g, 13.1 mmol), K2CO3 (90.5 g, 654.7 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0334] 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 = 9:1 (v / v)) to obtain 9'-chloro-9-phenyl-3,4'-bidibenzo[b,d]furan (72.2 g, yield 62%).

[0335] Mass (theoretical: 444.91, measured: 444 g / mol)

[0336] <Step 3> Synthesis of DDB-5

[0337]

[0338] Under a nitrogen stream, 9'-chloro-9-phenyl-3,4'-bidibenzo[b,d]furan (72.2 g, 162.4 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (45.4 g, 178.6 mmol), Pd2(dba)3 (4.5 g, 4.9 mmol), X-Phos (10.8 g, 22.7 mmol), KOAc (30.6 g, 324.7 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0339] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain DDB-5 (54.9 g, yield 63%).

[0340] Mass (theoretical: 536.43, measured: 536 g / mol)

[0341] [Preparation Example 6] Synthesis of DDB-6

[0342] <Step 1-3> Synthesis of DDB-6

[0343]

[0344] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 7-bromo-1-chlorodibenzo[b,d]furan (83.6 g, 297.1 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-6 (55.1 g, final yield 28.6%).

[0345] Mass (theoretical: 536.43, measured: 536 g / mol)

[0346] [Preparation Example 7] Synthesis of DDB-7

[0347] <Step 1-3> Synthesis of DDB-7

[0348]

[0349]

[0350] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 8-bromo-1-chlorodibenzo[b,d]furan (84.8 g, 301.3 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-7 (57.8 g, final yield 30.0%).

[0351] Mass (theoretical: 536.43, measured: 536 g / mol)

[0352] [Preparation Example 8] Synthesis of DDB-8

[0353] <Step 1-3> Synthesis of DDB-8

[0354]

[0355] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 1-bromo-9-chlorodibenzo[b,d]furan (81.2 g, 288.4 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-8 (48.0 g, final yield 24.9%).

[0356] Mass (theoretical: 536.43, measured: 536 g / mol)

[0357] [Example 9] Synthesis of DDB-9

[0358] <Step 1-3> Synthesis of DDB-9

[0359]

[0360] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 8-bromo-1-chlorodibenzo[b,d]furan (87.3 g, 310.0 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-9 (71.8 g, final yield 37.3%).

[0361] Mass (theoretical: 536.43, measured: 536 g / mol)

[0362] [Preparation Example 10] Synthesis of DDB-10

[0363] <Step 1-3> Synthesis of DDB-10

[0364]

[0365] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1'-biphenyl]-4-yl)-7-chlorodibenzo[b,d]furan (100.0 g, 282.4 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan (62.0 g, 220.3 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-10 (48.2 g, final yield 27.8%).

[0366] Mass (theoretical: 612.53, measured: 612 g / mol)

[0367] [Preparation Example 11] Synthesis of DDB-11

[0368] <Step 1> Synthesis of 4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane

[0369]

[0370] Under a nitrogen stream, 3-chloro-7-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (100.2 g, 394.6 mmol), Pd2(dba)3 (9.9 g, 10.8 mmol), X-Phos (23.9 g, 50.2 mmol), KOAc (67.6 g, 717.5 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0371] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain 4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (90.3 g, yield 68%).

[0372] Mass (theoretical: 370.26, measured: 370 g / mol)

[0373] <Step 2> Synthesis of 9'-chloro-7-phenyl-3,4'-bidibenzo[b,d]furan

[0374]

[0375] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane (90.3 g, 244.0 mmol), 6-bromo-1-chlorodibenzo[b,d]furan (82.4 g, 292.7 mmol), Pd(PPh3)4 (14.1 g, 12.2 mmol), K2CO3 (84.3 g, 609.9 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0376] 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 = 9:1 (v / v)) to obtain 9'-chloro-7-phenyl-3,4'-bidibenzo[b,d]furan (70.5 g, yield 65%).

[0377] Mass (theoretical: 444.91, measured: 444 g / mol)

[0378] <Step 3> Synthesis of DDB-11

[0379]

[0380] Under a nitrogen stream, 9'-chloro-7-phenyl-3,4'-bidibenzo[b,d]furan (73.7 g, 165.6 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (46.2 g, 182.1 mmol), Pd2(dba)3 (4.5 g, 5.0 mmol), X-Phos (11.1 g, 23.2 mmol), KOAc (31.2 g, 331.1 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 = 8:1 (v / v)) to obtain DDB-11 (54.4 g, yield 64%).

[0382] Mass (theoretical: 536.43, measured: 536 g / mol)

[0383] [Example 12] Synthesis of DDB-12

[0384] <Step 1-3> Synthesis of DDB-12

[0385]

[0386] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 7-bromo-1-chlorodibenzo[b,d]furan (80.0 g, 284.1 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-12 (58.7 g, final yield 30.5%).

[0387] Mass (theoretical: 536.43, measured: 536 g / mol)

[0388] [Preparation Example 13] Synthesis of DDB-13

[0389] <Step 1-3> Synthesis of DDB-13

[0390]

[0391] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 1-bromo-9-chlorodibenzo[b,d]furan (71.5 g, 254.0 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) to obtain the target compound DDB-13 (40.2 g, final yield 20.9%).

[0392] Mass (theoretical: 536.43, measured: 536 g / mol)

[0393] [Example 14] Synthesis of DDB-14

[0394] <Step 1-3> Synthesis of DDB-14

[0395]

[0396] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1'-biphenyl]-4-yl)-8-chlorodibenzo[b,d]furan (100.0 g, 282.4 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan (62.0 g, 220.3 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-14 (39.3 g, final yield 22.7%).

[0397] Mass (theoretical: 612.53, measured: 612 g / mol)

[0398] [Example 15] Synthesis of DDB-15

[0399] <Step 1-3> Synthesis of DDB-15

[0400]

[0401] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1'-biphenyl]-3-yl)-9-chlorodibenzo[b,d]furan (100.0 g, 282.4 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 7-bromo-1-chlorodibenzo[b,d]furan (60.1 g, 213.5 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-15 (41.7 g, final yield 24.1%).

[0402] Mass (theoretical: 612.53, measured: 612 g / mol)

[0403] [Preparation Example 16] Synthesis of DDB-16

[0404] <Step 1-3> Synthesis of DDB-16

[0405]

[0406] The same procedure as steps 1 to 3 of Preparation Example 1 was followed except that 1-([1,1':2',1''-terphenyl]-4'-yl)-9-chlorodibenzo[b,d]furan (100.0 g, 232.1 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in step 1 of Preparation Example 1, to obtain the target compound DDB-16 (25.6 g, final yield 16.0%).

[0407] Mass (theoretical: 688.63, measured: 688 g / mol)

[0408] [Preparation Example 17] Synthesis of DDB-17

[0409] <Step 1-3> Synthesis of DDB-17

[0410]

[0411] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1':3',1''-terphenyl]-5'-yl)-9-chlorodibenzo[b,d]furan (100.0 g, 232.1 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan (43.9 g, 155.9 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-17 (25.0 g, final yield 15.6%).

[0412] Mass (theoretical: 688.63, measured: 688 g / mol)

[0413] [Example 18] Synthesis of DDB-18

[0414] <Step 1-3> Synthesis of DDB-18

[0415]

[0416] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1':4',1''-terphenyl]-2'-yl)-9-chlorodibenzo[b,d]furan (100.0 g, 232.1 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 1-bromo-9-chlorodibenzo[b,d]furan (40.8 g, 144.8 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-18 (22.4 g, final yield 14.0%).

[0417] Mass (theoretical: 688.63, measured: 688 g / mol)

[0418] [Preparation Example 19] Synthesis of DDB-19

[0419] <Step 1-3> Synthesis of DDB-19

[0420]

[0421] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 7-chloro-1-(phenyl-d5)dibenzo[b,d]furan-2,3,4,6,8,9-d6 (100.0 g, 345.1 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan-2,3,4,6,7,9-d6 (71.4 g, 248.4 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-19 (37.5 g, final yield 19.7%).

[0422] Mass (theoretical: 553.54, measured: 553 g / mol)

[0423] [Preparation Example 20] Synthesis of DDB-20

[0424] <Step 1-3> Synthesis of DDB-20

[0425]

[0426] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 3-chloro-6-(phenyl-d5)dibenzo[b,d]furan-1,2,4,7,8,9-d6 (100.0 g, 345.1 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1, and 8-bromo-1-chlorodibenzo[b,d]furan-2,3,4,6,7,9-d6 (75.0 g, 260.9 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-20 (41.2 g, final yield 21.6%).

[0427] Mass (theoretical: 553.54, measured: 553 g / mol)

[0428] [Preparation Example 21] Synthesis of DDB-21

[0429] <Step 1-3> Synthesis of DDB-21

[0430]

[0431] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 1-bromo-8-chlorodibenzo[b,d]furan (83.6 g, 297.1 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-21 (58.7 g, final yield 30.5%).

[0432] Mass (theoretical: 536.43, measured: 536 g / mol)

[0433] [Example 22] Synthesis of DDB-22

[0434] <Step 1-3> Synthesis of DDB-22

[0435]

[0436] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 1-bromo-7-chlorodibenzo[b,d]furan (86.1 g, 305.7 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-22 (63.8 g, final yield 33.2%).

[0437] Mass (theoretical: 536.43, measured: 536 g / mol)

[0438] [Example 23] Synthesis of DDB-23

[0439] <Step 1-3> Synthesis of DDB-23

[0440]

[0441] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 3-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 4-bromo-6-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-23 (52.7 g, final yield 27.4%).

[0442] Mass (theoretical: 536.43, measured: 536 g / mol)

[0443] [Preparation Example 24] Synthesis of DDB-24

[0444] <Step 1-3> Synthesis of DDB-24

[0445]

[0446] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 4-chloro-6-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 4-bromo-6-chlorodibenzo[b,d]furan (87.3 g, 310.0 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-24 (55.9 g, final yield 29.0%).

[0447] Mass (theoretical: 536.43, measured: 536 g / mol)

[0448] [Preparation Example 25] Synthesis of DDB-25

[0449] <Step 1> Synthesis of 1-chloro-8-(6-phenyldibenzo[b,d]thiophen-3-yl)dibenzo[b,d]furan

[0450]

[0451]

[0452] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-3-yl)-1,3,2-dioxaborolane (100.0 g, 258.9 mmol), 8-bromo-1-chlorodibenzo[b,d]furan (87.5 g, 310.6 mmol), Pd(PPh3)4 (15.0 g, 12.9 mmol), K2CO3 (89.4 g, 647.1 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 hours.

[0453] 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 = 9:1 (v / v)) to obtain 1-chloro-8-(6-phenyldibenzo[b,d]thiophen-3-yl)dibenzo[b,d]furan (82.3 g, yield 69%).

[0454] Mass (theoretical: 460.98, measured: 460 g / mol)

[0455] <Step 2> Synthesis of DDB-25

[0456]

[0457] Under a nitrogen stream, 1-chloro-8-(6-phenyldibenzo[b,d]thiophen-3-yl)dibenzo[b,d]furan (82.3 g, 178.6 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (49.9 g, 196.5 mmol), Pd2(dba)3 (4.9 g, 5.4 mmol), X-Phos (11.9 g, 25.0 mmol), KOAc (33.6 g, 357.2 mmol) and 1,4-Dioxane (2000 ml) were mixed and stirred at 130°C for 12 h.

[0458] After the reaction was completed, the mixture was extracted with ethyl acetate, dried with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain DDB-25 (63.2 g, yield 64%).

[0459] Mass (theoretical: 552.49, measured: 552 g / mol)

[0460] [Preparation Example 26] Synthesis of DDB-26

[0461] <Step 1-2> Synthesis of DDB-26

[0462]

[0463] The same procedure as steps 1 to 2 of Preparation Example 24 was followed except that 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-4-yl)-1,3,2-dioxaborolane (100.0 g, 258.9 mmol) was used instead of 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]thiophen-3-yl)-1,3,2-dioxaborolane (100.0 g, 258.9 mmol) in step 1 of Preparation Example 24, to obtain the target compound DDB-26 (69.0 g, final yield 48.2%).

[0464] Mass (theoretical: 552.49, measured: 552 g / mol)

[0465] [Preparation Example 27] Synthesis of DDB-27

[0466] <Step 1-3> Synthesis of DDB-27

[0467]

[0468] The same procedure as in Steps 1 to 3 of Preparation Example 1 was followed, except that 1-([1,1'-biphenyl]-4-yl)-7-chlorodibenzo[b,d]furan (100.0 g, 310.7 mmol) was used instead of 6-chloro-2-phenyldibenzo[b,d]furan (100.0 g, 358.7 mmol) in Step 1 of Preparation Example 1 and 1-bromo-8-chlorodibenzo[b,d]furan (62.0 g, 220.3 mmol) was used instead of 6-bromo-1-chlorodibenzo[b,d]furan (78.8 g, 279.8 mmol) in Step 2 of Preparation Example 1, to obtain the target compound DDB-27 (50.5 g, final yield 29.2%).

[0469] Mass (theoretical: 612.53, measured: 612 g / mol)

[0470] [Synthesis Example 1] Synthesis of A-1

[0471]

[0472] Under a nitrogen atmosphere, DDB-1 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0473] 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 = 4:1 (v / v)) to obtain the target compound A-1 (9.0 g, yield 75%).

[0474] Mass (theoretical: 641.73, measured: 641 g / mol)

[0475] [Synthesis Example 2] Synthesis of A-2

[0476]

[0477] The same procedure as in Synthetic Example 1 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-2 (8.4 g, yield 69%).

[0478] Mass (theoretical: 651.79, measured: 651 g / mol)

[0479] [Synthesis Example 3] Synthesis of A-3

[0480]

[0481] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-3 (9.5 g, yield 71%).

[0482] Mass (theoretical: 717.83, measured: 717 g / mol)

[0483] [Synthesis Example 4] Synthesis of A-4

[0484]

[0485] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-4 (9.6 g, yield 72%).

[0486] Mass (theoretical: 717.83, measured: 717 g / mol)

[0487] [Synthesis Example 5] Synthesis of A-5

[0488]

[0489] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-5 (8.7 g, yield 65%).

[0490] Mass (theoretical: 717.83, measured: 717 g / mol)

[0491] [Synthesis Example 6] Synthesis of A-6

[0492]

[0493] The same procedure as in Synthetic Example 1 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-6 (11.0 g, yield 74%).

[0494] Mass (theoretical: 793.93, measured: 793 g / mol)

[0495] [Synthesis Example 7] Synthesis of A-7

[0496]

[0497] The same procedure as in Synthetic Example 1 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-7 (9.3 g, yield 63%).

[0498] Mass (theoretical: 793.93, measured: 793 g / mol)

[0499] [Synthesis Example 8] Synthesis of A-8

[0500]

[0501] The same procedure as in Synthesis Example 1 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound A-8 (9.2 g, yield 62%).

[0502] Mass (theoretical: 793.93, measured: 793 g / mol)

[0503] [Synthesis Example 9] Synthesis of B-1

[0504]

[0505] Under a nitrogen atmosphere, DDB-2 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0506] 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 = 4:1 (v / v)) to obtain the target compound B-1 (8.5 g, yield 71%).

[0507] Mass (theoretical: 641.73, measured: 641 g / mol)

[0508] [Synthesis Example 10] Synthesis of B-2

[0509]

[0510] The same procedure as in Synthetic Example 9 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-2 (7.7 g, yield 63%).

[0511] Mass (theoretical: 651.79, measured: 651 g / mol)

[0512] [Synthesis Example 11] Synthesis of B-3

[0513]

[0514] The same procedure as in Synthetic Example 9 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-3 (8.6 g, yield 64%).

[0515] Mass (theoretical: 717.83, measured: 717 g / mol)

[0516] [Synthesis Example 12] Synthesis of B-4

[0517]

[0518] The same procedure as in Synthetic Example 9 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-4 (8.2 g, yield 61%).

[0519] Mass (theoretical: 717.83, measured: 717 g / mol)

[0520] [Synthesis Example 13] Synthesis of B-5

[0521]

[0522] The same procedure as in Synthetic Example 9 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-5 (9.2 g, yield 69%).

[0523] Mass (theoretical: 717.83, measured: 717 g / mol)

[0524] [Synthesis Example 14] Synthesis of B-6

[0525]

[0526] The same procedure as in Synthetic Example 9 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-6 (10.4 g, yield 70%).

[0527] Mass (theoretical: 793.93, measured: 793 g / mol)

[0528] [Synthesis Example 15] Synthesis of B-7

[0529]

[0530] The same procedure as in Synthetic Example 9 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-7 (9.5 g, yield 64%).

[0531] Mass (theoretical: 793.93, measured: 793 g / mol)

[0532] [Synthesis Example 16] Synthesis of B-8

[0533]

[0534] The same procedure as in Synthetic Example 9 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound B-8 (9.0 g, yield 61%).

[0535] Mass (theoretical: 793.93, measured: 793 g / mol)

[0536] [Synthesis Example 17] Synthesis of C-1

[0537]

[0538] Under a nitrogen stream, DDB-3 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0539] 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 = 4:1 (v / v)) to obtain the target compound C-1 (8.1 g, yield 68%).

[0540] Mass (theoretical: 641.73, measured: 641 g / mol)

[0541] [Synthesis Example 18] Synthesis of C-2

[0542]

[0543] The same procedure as in Synthetic Example 17 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-2 (7.9 g, yield 65%).

[0544] Mass (theoretical: 651.79, measured: 651 g / mol)

[0545] [Synthesis Example 19] Synthesis of C-3

[0546]

[0547] The same procedure as in Synthetic Example 17 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-3 (9.0 g, yield 67%).

[0548] Mass (theoretical: 717.83, measured: 717 g / mol)

[0549] [Synthesis Example 20] Synthesis of C-4

[0550]

[0551] The same procedure as in Synthetic Example 17 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-4 (8.4 g, yield 63%).

[0552] Mass (theoretical: 717.83, measured: 717 g / mol)

[0553] [Synthesis Example 21] Synthesis of C-5

[0554]

[0555] The same procedure as in Synthetic Example 17 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-5 (9.4 g, yield 70%).

[0556] Mass (theoretical: 717.83, measured: 717 g / mol)

[0557] [Synthesis Example 22] Synthesis of C-6

[0558]

[0559] The same procedure as in Synthetic Example 17 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-6 (10.7 g, yield 72%).

[0560] Mass (theoretical: 793.93, measured: 793 g / mol)

[0561] [Synthesis Example 23] Synthesis of C-7

[0562]

[0563] The same procedure as in Synthetic Example 17 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-7 (10.1 g, yield 68%).

[0564] Mass (theoretical: 793.93, measured: 793 g / mol)

[0565] [Synthesis Example 24] Synthesis of C-8

[0566]

[0567] The same procedure as in Synthetic Example 17 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound C-8 (10.4 g, yield 70%).

[0568] Mass (theoretical: 793.93, measured: 793 g / mol)

[0569] [Synthesis Example 25] Synthesis of D-1

[0570]

[0571] Under a nitrogen stream, DDB-4 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0572] 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 = 4:1 (v / v)) to obtain the target compound D-1 (7.3 g, yield 61%).

[0573] Mass (theoretical: 641.73, measured: 641 g / mol)

[0574] [Synthesis Example 26] Synthesis of D-2

[0575]

[0576] The same procedure as in Synthetic Example 25 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 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 68%).

[0577] Mass (theoretical: 651.79, measured: 651 g / mol)

[0578] [Synthesis Example 27] Synthesis of D-3

[0579]

[0580] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-3 (8.3 g, yield 62%).

[0581] Mass (theoretical: 717.83, measured: 717 g / mol)

[0582] [Synthesis Example 28] Synthesis of D-4

[0583]

[0584] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-4 (9.4 g, yield 70%).

[0585] Mass (theoretical: 717.83, measured: 717 g / mol)

[0586] [Synthesis Example 29] Synthesis of D-5

[0587]

[0588] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-5 (8.6 g, yield 64%).

[0589] Mass (theoretical: 717.83, measured: 717 g / mol)

[0590] [Synthesis Example 30] Synthesis of D-6

[0591]

[0592] The same procedure as in Synthetic Example 25 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-6 (9.6 g, yield 65%).

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

[0594] [Synthesis Example 31] Synthesis of D-7

[0595]

[0596] The same procedure as in Synthetic Example 25 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-7 (10.5 g, yield 71%).

[0597] Mass (theoretical: 793.93, measured: 793 g / mol)

[0598] [Synthesis Example 32] Synthesis of D-8

[0599]

[0600] The same procedure as in Synthetic Example 25 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound D-8 (9.0 g, yield 61%).

[0601] Mass (theoretical: 793.93, measured: 793 g / mol)

[0602] [Synthesis Example 33] Synthesis of E-1

[0603]

[0604] Under a nitrogen atmosphere, DDB-5 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0605] 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 = 4:1 (v / v)) to obtain the target compound E-1 (8.4 g, yield 70%).

[0606] Mass (theoretical: 641.73, measured: 641 g / mol)

[0607] [Synthesis Example 34] Synthesis of E-2

[0608]

[0609] The same procedure as in Synthetic Example 33 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-2 (8.3 g, yield 68%).

[0610] Mass (theoretical: 651.79, measured: 651 g / mol)

[0611] [Synthesis Example 35] Synthesis of E-3

[0612]

[0613] The same procedure as in Synthesis Example 33 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-3 (9.8 g, yield 73%).

[0614] Mass (theoretical: 717.83, measured: 717 g / mol)

[0615] [Synthesis Example 36] Synthesis of E-4

[0616]

[0617] The same procedure as in Synthesis Example 33 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-4 (9.5 g, yield 71%).

[0618] Mass (theoretical: 717.83, measured: 717 g / mol)

[0619] [Synthesis Example 37] Synthesis of E-5

[0620]

[0621] The same procedure as in Synthesis Example 33 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-5 (9.2 g, yield 69%).

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

[0623] [Synthesis Example 38] Synthesis of E-6

[0624]

[0625] The same procedure as in Synthetic Example 33 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-6 (10.8 g, yield 73%).

[0626] Mass (theoretical: 793.93, measured: 793 g / mol)

[0627] [Synthesis Example 39] Synthesis of E-7

[0628]

[0629] The same procedure as in Synthesis Example 33 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-7 (10.1 g, yield 68%).

[0630] Mass (theoretical: 793.93, measured: 793 g / mol)

[0631] [Synthesis Example 40] Synthesis of E-8

[0632]

[0633] The same procedure as in Synthesis Example 33 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound E-8 (9.5 g, yield 64%).

[0634] Mass (theoretical: 793.93, measured: 793 g / mol)

[0635] [Synthesis Example 41] Synthesis of F-1

[0636]

[0637] Under a nitrogen stream, DDB-6 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0638] 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 = 4:1 (v / v)) to obtain the target compound F-1 (7.5 g, yield 63%).

[0639] Mass (theoretical: 641.73, measured: 641 g / mol)

[0640] [Synthesis Example 42] Synthesis of F-2

[0641]

[0642] The same procedure as in Synthesis Example 41 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-2 (8.1 g, yield 67%).

[0643] Mass (theoretical: 651.79, measured: 651 g / mol)

[0644] [Synthesis Example 43] Synthesis of F-3

[0645] The same procedure as in Synthesis Example 41 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-3 (8.7 g, yield 65%).

[0646] Mass (theoretical: 717.83, measured: 717 g / mol)

[0647] [Synthesis Example 44] Synthesis of F-4

[0648]

[0649] The same procedure as in Synthesis Example 41 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-4 (8.6 g, yield 64%).

[0650] Mass (theoretical: 717.83, measured: 717 g / mol)

[0651] [Synthesis Example 45] Synthesis of F-5

[0652]

[0653] The same procedure as in Synthetic Example 41 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-5 (8.4 g, yield 63%).

[0654] Mass (theoretical: 717.83, measured: 717 g / mol)

[0655] [Synthesis Example 46] Synthesis of F-6

[0656]

[0657] The same procedure as in Synthesis Example 41 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-6 (9.6 g, yield 65%).

[0658] Mass (theoretical: 793.93, measured: 793 g / mol)

[0659] [Synthesis Example 47] Synthesis of F-7

[0660]

[0661] The same procedure as in Synthetic Example 41 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-7 (9.2 g, yield 62%).

[0662] Mass (theoretical: 793.93, measured: 793 g / mol)

[0663] [Synthesis Example 48] Synthesis of F-8

[0664]

[0665] The same procedure as in Synthesis Example 41 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound F-8 (9.0 g, yield 61%).

[0666] Mass (theoretical: 793.93, measured: 793 g / mol)

[0667] [Synthesis Example 49] Synthesis of G-1

[0668]

[0669] Under a nitrogen atmosphere, DDB-7 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0670] 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 = 4:1 (v / v)) to obtain the target compound G-1 (7.8 g, yield 65%).

[0671] Mass (theoretical: 641.73, measured: 641 g / mol)

[0672] [Synthesis Example 50] Synthesis of G-2

[0673]

[0674] The same procedure as in Synthesis Example 49 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-2 (7.4 g, yield 61%).

[0675] Mass (theoretical: 651.79, measured: 651 g / mol)

[0676] [Synthesis Example 51] Synthesis of G-3

[0677]

[0678] The same procedure as in Synthetic Example 49 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-3 (8.6 g, yield 64%).

[0679] Mass (theoretical: 717.83, measured: 717 g / mol)

[0680] [Synthesis Example 52] Synthesis of G-4

[0681]

[0682] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-4 (9.1 g, yield 68%).

[0683] Mass (theoretical: 717.83, measured: 717 g / mol)

[0684] [Synthesis Example 53] Synthesis of G-5

[0685]

[0686] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-5 (8.3 g, yield 62%).

[0687] Mass (theoretical: 717.83, measured: 717 g / mol)

[0688] [Synthesis Example 54] Synthesis of G-6

[0689]

[0690] The same procedure as in Synthetic Example 49 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-6 (9.9 g, yield 67%).

[0691] Mass (theoretical: 793.93, measured: 793 g / mol)

[0692] [Synthesis Example 55] Synthesis of G-7

[0693]

[0694] The same procedure as in Synthesis Example 49 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-7 (8.9 g, yield 60%).

[0695] Mass (theoretical: 793.93, measured: 793 g / mol)

[0696] [Synthesis Example 56] Synthesis of G-8

[0697]

[0698] The same procedure as in Synthesis Example 49 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound G-8 (9.6 g, yield 65%).

[0699] Mass (theoretical: 793.93, measured: 793 g / mol)

[0700] [Synthesis Example 57] Synthesis of H-1

[0701]

[0702] Under a nitrogen stream, DDB-8 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0703] 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 = 4:1 (v / v)) to obtain the target compound H-1 (8.5 g, yield 71%).

[0704] Mass (theoretical: 641.73, measured: 641 g / mol)

[0705] [Synthesis Example 58] Synthesis of H-2

[0706]

[0707] The same procedure as in Synthesis Example 57 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-2 (8.3 g, yield 68%).

[0708] Mass (theoretical: 651.79, measured: 651 g / mol)

[0709] [Synthesis Example 59] Synthesis of H-3

[0710]

[0711] The same procedure as in Synthesis Example 57 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-3 (9.1 g, yield 68%).

[0712] Mass (theoretical: 717.83, measured: 717 g / mol)

[0713] [Synthesis Example 60] Synthesis of H-4

[0714]

[0715] The same procedure as in Synthesis Example 57 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-4 (9.4 g, yield 70%).

[0716] Mass (theoretical: 717.83, measured: 717 g / mol)

[0717] [Synthesis Example 61] Synthesis of H-5

[0718]

[0719] The same procedure as in Synthesis Example 57 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-5 (9.8 g, yield 73%).

[0720] Mass (theoretical: 717.83, measured: 717 g / mol)

[0721] [Synthesis Example 62] Synthesis of H-6

[0722]

[0723] The same procedure as in Synthesis Example 57 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-6 (10.5 g, yield 71%).

[0724] Mass (theoretical: 793.93, measured: 793 g / mol)

[0725] [Synthesis Example 63] Synthesis of H-7

[0726]

[0727] The same procedure as in Synthesis Example 57 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-7 (10.4 g, yield 70%).

[0728] Mass (theoretical: 793.93, measured: 793 g / mol)

[0729] [Synthesis Example 64] Synthesis of H-8

[0730]

[0731] The same procedure as in Synthesis Example 57 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound H-8 (10.2 g, yield 69%).

[0732] Mass (theoretical: 793.93, measured: 793 g / mol)

[0733] [Synthesis Example 65] Synthesis of I-1

[0734]

[0735] Under a nitrogen stream, DDB-9 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0736] 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 = 4:1 (v / v)) to obtain the target compound I-1 (7.8 g, yield 65%).

[0737] Mass (theoretical: 641.73, measured: 641 g / mol)

[0738] [Synthesis Example 66] Synthesis of I-2

[0739]

[0740] The same procedure as in Synthesis Example 65 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-2 (7.8 g, yield 64%).

[0741] Mass (theoretical: 651.79, measured: 651 g / mol)

[0742] [Synthesis Example 67] Synthesis of I-3

[0743]

[0744] The same procedure as in Synthesis Example 65 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-3 (8.8 g, yield 66%).

[0745] Mass (theoretical: 717.83, measured: 717 g / mol)

[0746] [Synthesis Example 68] Synthesis of I-4

[0747]

[0748] The same procedure as in Synthesis Example 65 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-4 (8.4 g, yield 63%).

[0749] Mass (theoretical: 717.83, measured: 717 g / mol)

[0750] [Synthesis Example 69] Synthesis of I-5

[0751]

[0752] The same procedure as in Synthesis Example 65 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-5 (8.6 g, yield 64%).

[0753] Mass (theoretical: 717.83, measured: 717 g / mol)

[0754] [Synthesis Example 70] Synthesis of I-6

[0755]

[0756] The same procedure as in Synthesis Example 65 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-6 (9.9 g, yield 67%).

[0757] Mass (theoretical: 793.93, measured: 793 g / mol)

[0758] [Synthesis Example 71] Synthesis of I-7

[0759]

[0760] The same procedure as in Synthesis Example 65 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-7 (9.2 g, yield 62%).

[0761] Mass (theoretical: 793.93, measured: 793 g / mol)

[0762] [Synthesis Example 72] Synthesis of I-8

[0763]

[0764] The same procedure as in Synthesis Example 65 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound I-8 (9.5 g, yield 64%).

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

[0766] [Synthesis Example 73] Synthesis of J-1

[0767]

[0768] Under a nitrogen atmosphere, DDB-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 h.

[0769] 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 = 4:1 (v / v)) to obtain the target compound J-1 (7.6 g, yield 65%).

[0770] Mass (theoretical: 717.83, measured: 717 g / mol)

[0771] [Synthesis Example 74] Synthesis of J-2

[0772]

[0773] The same procedure as in Synthesis Example 73 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 (7.8 g, yield 64%).

[0774] Mass (theoretical: 727.89, measured: 727 g / mol)

[0775] [Synthesis Example 75] Synthesis of J-3

[0776]

[0777] 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 (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-3 (8.0 g, yield 62%).

[0778] Mass (theoretical: 793.93, measured: 793 g / mol)

[0779] [Synthesis Example 76] Synthesis of J-4

[0780]

[0781] 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 (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-4 (8.7 g, yield 67%).

[0782] Mass (theoretical: 793.93, measured: 793 g / mol)

[0783] [Synthesis Example 77] Synthesis of J-5

[0784]

[0785] 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 (6.7 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-5 (7.9 g, yield 61%).

[0786] Mass (theoretical: 793.93, measured: 793 g / mol)

[0787] [Synthesis Example 78] Synthesis of J-6

[0788]

[0789] The same procedure as in Synthesis Example 73 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-6 (8.9 g, yield 63%).

[0790] Mass (theoretical: 870.02, measured: 870 g / mol)

[0791] [Synthesis Example 79] Synthesis of J-7

[0792]

[0793] The same procedure as in Synthesis Example 73 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-7 (9.4 g, yield 66%).

[0794] Mass (theoretical: 870.02, measured: 870 g / mol)

[0795] [Synthesis Example 80] Synthesis of J-8

[0796]

[0797] The same procedure as in Synthesis Example 73 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound J-8 (8.7 g, yield 61%).

[0798] Mass (theoretical: 870.02, measured: 870 g / mol)

[0799] [Synthesis Example 81] Synthesis of K-1

[0800]

[0801] Under a nitrogen stream, DDB-11 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0802] 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 = 4:1 (v / v)) to obtain the target compound K-1 (8.5 g, yield 71%).

[0803] Mass (theoretical: 641.73, measured: 641 g / mol)

[0804] [Synthesis Example 82] Synthesis of K-2

[0805]

[0806] The same procedure as in Synthesis Example 81 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-2 (8.3 g, yield 68%).

[0807] Mass (theoretical: 651.79, measured: 651 g / mol)

[0808] [Synthesis Example 83] Synthesis of K-3

[0809]

[0810] The same procedure as in Synthesis Example 81 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-3 (8.7 g, yield 65%).

[0811] Mass (theoretical: 717.83, measured: 717 g / mol)

[0812] [Synthesis Example 84] Synthesis of K-4

[0813]

[0814] The same procedure as in Synthesis Example 81 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-4 (9.1 g, yield 68%).

[0815] Mass (theoretical: 717.83, measured: 717 g / mol)

[0816] [Synthesis Example 85] Synthesis of K-5

[0817]

[0818] The same procedure as in Synthesis Example 81 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-5 (8.7 g, yield 65%).

[0819] Mass (theoretical: 717.83, measured: 717 g / mol)

[0820] [Synthesis Example 86] Synthesis of K-6

[0821]

[0822] The same procedure as in Synthesis Example 81 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-6 (9.5 g, yield 64%).

[0823] Mass (theoretical: 793.93, measured: 793 g / mol)

[0824] [Synthesis Example 87] Synthesis of K-7

[0825]

[0826] The same procedure as in Synthesis Example 81 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-7 (9.8 g, yield 66%).

[0827] Mass (theoretical: 793.93, measured: 793 g / mol)

[0828] [Synthesis Example 88] Synthesis of K-8

[0829]

[0830] The same procedure as in Synthesis Example 81 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound K-8 (9.9 g, yield 67%).

[0831] Mass (theoretical: 793.93, measured: 793 g / mol)

[0832] [Synthesis Example 89] Synthesis of L-1

[0833]

[0834] Under a nitrogen atmosphere, DDB-12 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0835] 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 = 4:1 (v / v)) to obtain the target compound L-1 (7.8 g, yield 65%).

[0836] Mass (theoretical: 641.73, measured: 641 g / mol)

[0837] [Synthesis Example 90] Synthesis of L-2

[0838]

[0839] The same procedure as in Synthesis Example 89 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-2 (7.7 g, yield 63%).

[0840] Mass (theoretical: 651.79, measured: 651 g / mol)

[0841] [Synthesis Example 91] Synthesis of L-3

[0842]

[0843] The same procedure as in Synthesis Example 89 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-3 (8.2 g, yield 61%).

[0844] Mass (theoretical: 717.83, measured: 717 g / mol)

[0845] [Synthesis Example 92] Synthesis of L-4

[0846]

[0847] The same procedure as in Synthesis Example 89 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-4 (8.4 g, yield 63%).

[0848] Mass (theoretical: 717.83, measured: 717 g / mol)

[0849] [Synthesis Example 93] Synthesis of L-5

[0850] The same procedure as in Synthesis Example 89 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-5 (8.7 g, yield 64%).

[0851] Mass (theoretical: 717.83, measured: 717 g / mol)

[0852] [Synthesis Example 94] Synthesis of L-6

[0853]

[0854] The same procedure as in Synthesis Example 89 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-6 (9.8 g, yield 66%).

[0855] Mass (theoretical: 793.93, measured: 793 g / mol)

[0856] [Synthesis Example 95] Synthesis of L-7

[0857]

[0858] The same procedure as in Synthesis Example 89 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-7 (10.1 g, yield 68%).

[0859] Mass (theoretical: 793.93, measured: 793 g / mol)

[0860] [Synthesis Example 96] Synthesis of L-8

[0861]

[0862] The same procedure as in Synthesis Example 89 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound L-8 (9.2 g, yield 62%).

[0863] Mass (theoretical: 793.93, measured: 793 g / mol)

[0864] [Synthesis Example 97] Synthesis of M-1

[0865]

[0866] Under a nitrogen stream, DDB-13 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0867] 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 = 4:1 (v / v)) to obtain the target compound M-1 (8.5 g, yield 71%).

[0868] Mass (theoretical: 641.73, measured: 641 g / mol)

[0869] [Synthesis Example 98] Synthesis of M-2

[0870]

[0871] The same procedure as in Synthesis Example 97 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.2 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-2 (8.3 g, yield 68%).

[0872] Mass (theoretical: 651.79, measured: 651 g / mol)

[0873] [Synthesis Example 99] Synthesis of M-3

[0874]

[0875] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-3 (9.0 g, yield 67%).

[0876] Mass (theoretical: 717.83, measured: 717 g / mol)

[0877] [Synthesis Example 100] Synthesis of M-4

[0878]

[0879] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-4 (9.0 g, yield 67%).

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

[0881] [Synthesis Example 101] Synthesis of M-5

[0882]

[0883] 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 (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-5 (8.8 g, yield 66%).

[0884] Mass (theoretical: 717.83, measured: 717 g / mol)

[0885] [Synthesis Example 102] Synthesis of M-6

[0886]

[0887] The same procedure as in Synthesis Example 97 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-6 (10.4 g, yield 70%).

[0888] Mass (theoretical: 793.93, measured: 793 g / mol)

[0889] [Synthesis Example 103] Synthesis of M-7

[0890]

[0891] The same procedure as in Synthesis Example 97 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-7 (10.8 g, yield 73%).

[0892] Mass (theoretical: 793.93, measured: 793 g / mol)

[0893] [Synthesis Example 104] Synthesis of M-8

[0894]

[0895] The same procedure as in Synthesis Example 97 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.4 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound M-8 (11.0 g, yield 74%).

[0896] Mass (theoretical: 793.93, measured: 793 g / mol)

[0897] [Synthesis Example 105] Synthesis of N-1

[0898]

[0899] Under a nitrogen stream, DDB-14 (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.

[0900] 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 = 4:1 (v / v)) to obtain the target compound N-1 (7.1 g, yield 61%).

[0901] Mass (theoretical: 717.83, measured: 717 g / mol)

[0902] [Synthesis Example 106] Synthesis of N-2

[0903]

[0904] The same procedure as in Synthesis Example 105 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 N-2 (7.4 g, yield 62%).

[0905] Mass (theoretical: 727.89, measured: 727 g / mol)

[0906] [Synthesis Example 107] Synthesis of N-3

[0907]

[0908] The same procedure as in Synthesis Example 105 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 N-3 (8.2 g, yield 63%).

[0909] Mass (theoretical: 793.93, measured: 793 g / mol)

[0910] [Synthesis Example 108] Synthesis of N-4

[0911]

[0912] The same procedure as in Synthesis Example 105 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 N-4 (7.9 g, yield 61%).

[0913] Mass (theoretical: 793.93, measured: 793 g / mol)

[0914] [Synthesis Example 109] Synthesis of N-5

[0915]

[0916] The same procedure as in Synthesis Example 105 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 N-5 (8.0 g, yield 62%).

[0917] Mass (theoretical: 793.93, measured: 793 g / mol)

[0918] [Synthesis Example 110] Synthesis of N-6

[0919]

[0920] The same procedure as in Synthesis Example 105 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-6 (9.1 g, yield 64%).

[0921] Mass (theoretical: 870.02, measured: 870 g / mol)

[0922] [Synthesis Example 111] Synthesis of N-7

[0923]

[0924] The same procedure as in Synthesis Example 105 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-7 (8.5 g, yield 60%).

[0925] Mass (theoretical: 870.02, measured: 870 g / mol)

[0926] [Synthesis Example 112] Synthesis of N-8

[0927]

[0928] The same procedure as in Synthesis Example 105 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound N-8 (8.8 g, yield 62%).

[0929] Mass (theoretical: 870.02, measured: 870 g / mol)

[0930] [Synthesis Example 113] Synthesis of O-1

[0931]

[0932] Under a nitrogen stream, DDB-15 (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.

[0933] 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 = 4:1 (v / v)) to obtain the target compound O-1 (7.5 g, yield 64%).

[0934] Mass (theoretical: 717.83, measured: 717 g / mol)

[0935] [Synthesis Example 114] Synthesis of O-2

[0936]

[0937] The same procedure as in Synthesis Example 113 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 O-2 (7.5 g, yield 63%).

[0938] Mass (theoretical: 727.89, measured: 727 g / mol)

[0939] [Synthesis Example 115] Synthesis of O-3

[0940]

[0941] The same procedure as in Synthesis Example 113 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 O-3 (8.6 g, yield 66%).

[0942] Mass (theoretical: 793.93, measured: 793 g / mol)

[0943] [Synthesis Example 116] Synthesis of O-4

[0944]

[0945] The same procedure as in Synthesis Example 113 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 O-4 (8.4 g, yield 65%).

[0946] Mass (theoretical: 793.93, measured: 793 g / mol)

[0947] [Synthesis Example 117] Synthesis of O-5

[0948]

[0949] The same procedure as in Synthesis Example 113 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 O-5 (8.0 g, yield 62%).

[0950] Mass (theoretical: 793.93, measured: 793 g / mol)

[0951] [Synthesis Example 118] Synthesis of O-6

[0952]

[0953] The same procedure as in Synthesis Example 113 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-6 (9.5 g, yield 67%).

[0954] Mass (theoretical: 870.02, measured: 870 g / mol)

[0955] [Synthesis Example 119] Synthesis of O-7

[0956]

[0957] The same procedure as in Synthesis Example 113 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-7 (8.7 g, yield 61%).

[0958] Mass (theoretical: 870.02, measured: 870 g / mol)

[0959] [Synthesis Example 120] Synthesis of O-8

[0960]

[0961] The same procedure as in Synthesis Example 113 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (8.2 g, 19.6 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound O-8 (8.9 g, yield 63%).

[0962] Mass (theoretical: 870.02, measured: 870 g / mol)

[0963] [Synthesis Example 121] Synthesis of P-1

[0964]

[0965] Under a nitrogen atmosphere, DDB-16 (10.0 g, 14.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.7 g, 17.4 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), K2CO3 (5.0 g, 36.3 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0966] 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 = 4:1 (v / v)) to obtain the target compound P-1 (6.7 g, yield 58%).

[0967] Mass (theoretical: 793.93, measured: 793 g / mol)

[0968] [Synthesis Example 122] Synthesis of P-2

[0969] The same procedure as in Synthesis Example 121 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (4.8 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-2 (6.9 g, yield 59%).

[0970] Mass (theoretical: 803.99, measured: 803 g / mol)

[0971] [Synthesis Example 123] Synthesis of P-3

[0972]

[0973] The same procedure as in Synthesis Example 121 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-3 (7.1 g, yield 56%).

[0974] Mass (theoretical: 870.02, measured: 870 g / mol)

[0975] [Synthesis Example 124] Synthesis of P-4

[0976]

[0977] The same procedure as in Synthesis Example 121 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-4 (6.8 g, yield 54%).

[0978] Mass (theoretical: 870.02, measured: 870 g / mol)

[0979] [Synthesis Example 125] Synthesis of P-5

[0980]

[0981] The same procedure as in Synthesis Example 121 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-5 (7.2 g, yield 57%).

[0982] Mass (theoretical: 870.02, measured: 870 g / mol)

[0983] [Synthesis Example 126] Synthesis of P-6

[0984]

[0985] The same procedure as in Synthesis Example 121 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-6 (7.3 g, yield 53%).

[0986] Mass (theoretical: 946.12, measured: 946 g / mol)

[0987] [Synthesis Example 127] Synthesis of P-7

[0988]

[0989] The same procedure as in Synthesis Example 121 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-7 (7.1 g, yield 52%).

[0990] Mass (theoretical: 946.12, measured: 946 g / mol)

[0991] [Synthesis Example 128] Synthesis of P-8

[0992]

[0993] The same procedure as in Synthesis Example 121 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound P-8 (7.0 g, yield 51%).

[0994] Mass (theoretical: 946.12, measured: 946 g / mol)

[0995] [Synthesis Example 129] Synthesis of Q-1

[0996]

[0997] Under a nitrogen stream, DDB-17 (10.0 g, 14.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.7 g, 17.4 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), K2CO3 (5.0 g, 36.3 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[0998] 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 = 4:1 (v / v)) to obtain the target compound Q-1 (5.9 g, yield 51%).

[0999] Mass (theoretical: 793.93, measured: 793 g / mol)

[1000] [Synthesis Example 130] Synthesis of Q-2

[1001]

[1002] The same procedure as in Synthesis Example 129 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (4.8 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-2 (6.2 g, yield 53%).

[1003] Mass (theoretical: 803.99, measured: 803 g / mol)

[1004] [Synthesis Example 131] Synthesis of Q-3

[1005]

[1006] The same procedure as in Synthesis Example 129 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-3 (6.8 g, yield 54%).

[1007] Mass (theoretical: 870.02, measured: 870 g / mol)

[1008] [Synthesis Example 132] Synthesis of Q-4

[1009]

[1010] The same procedure as in Synthesis Example 129 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-4 (6.6 g, yield 52%).

[1011] Mass (theoretical: 870.02, measured: 870 g / mol)

[1012] [Synthesis Example 133] Synthesis of Q-5

[1013]

[1014] The same procedure as in Synthesis Example 129 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-5 (6.6 g, yield 52%).

[1015] Mass (theoretical: 870.02, measured: 870 g / mol)

[1016] [Synthesis Example 134] Synthesis of Q-6

[1017]

[1018] The same procedure as in Synthesis Example 129 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-6 (7.3 g, yield 53%).

[1019] Mass (theoretical: 946.12, measured: 946 g / mol)

[1020] [Synthesis Example 135] Synthesis of Q-7

[1021]

[1022] The same procedure as in Synthesis Example 129 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-7 (7.0 g, yield 51%).

[1023] Mass (theoretical: 946.12, measured: 946 g / mol)

[1024] [Synthesis Example 136] Synthesis of Q-8

[1025]

[1026] The same procedure as in Synthesis Example 129 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Q-8 (6.9 g, yield 50%).

[1027] Mass (theoretical: 946.12, measured: 946 g / mol)

[1028] [Synthesis Example 137] Synthesis of R-1

[1029]

[1030] Under a nitrogen stream, DDB-18 (10.0 g, 14.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.7 g, 17.4 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), K2CO3 (5.0 g, 36.3 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1031] 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 = 4:1 (v / v)) to obtain the target compound R-1 (6.2 g, yield 54%).

[1032] Mass (theoretical: 793.93, measured: 793 g / mol)

[1033] [Synthesis Example 138] Synthesis of R-2

[1034]

[1035] The same procedure as in Synthesis Example 137 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (4.8 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-2 (6.1 g, yield 52%).

[1036] Mass (theoretical: 803.99, measured: 803 g / mol)

[1037] [Synthesis Example 139] Synthesis of R-3

[1038]

[1039] The same procedure as in Synthesis Example 137 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-3 (6.9 g, yield 55%).

[1040] Mass (theoretical: 870.02, measured: 870 g / mol)

[1041] [Synthesis Example 140] Synthesis of R-4

[1042]

[1043] The same procedure as in Synthesis Example 137 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-4 (6.7 g, yield 53%).

[1044] Mass (theoretical: 870.02, measured: 870 g / mol)

[1045] [Synthesis Example 141] Synthesis of R-5

[1046]

[1047] The same procedure as in Synthesis Example 137 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.0 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-5 (6.3 g, yield 50%).

[1048] Mass (theoretical: 870.02, measured: 870 g / mol)

[1049] [Synthesis Example 142] Synthesis of R-6

[1050]

[1051] The same procedure as in Synthesis Example 137 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-6 (7.1 g, yield 52%).

[1052] Mass (theoretical: 946.12, measured: 946 g / mol)

[1053] [Synthesis Example 143] Synthesis of R-7

[1054]

[1055] The same procedure as in Synthesis Example 137 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-7 (7.6 g, yield 55%).

[1056] Mass (theoretical: 946.12, measured: 946 g / mol)

[1057] [Synthesis Example 144] Synthesis of R-8

[1058] The same procedure as in Synthesis Example 137 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (7.3 g, 17.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound R-8 (7.1 g, yield 52%).

[1059] Mass (theoretical: 946.12, measured: 946 g / mol)

[1060] [Synthesis Example 145] Synthesis of S-1

[1061]

[1062] Under a nitrogen stream, DDB-19 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.2 g, 45.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1063] 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 = 4:1 (v / v)) to obtain the target compound S-1 (8.1 g, yield 68%).

[1064] Mass (theoretical: 658.83, measured: 658 g / mol)

[1065] [Synthesis Example 146] Synthesis of S-2

[1066]

[1067] The same procedure as in Synthesis Example 145 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-2 (8.1 g, yield 67%).

[1068] Mass (theoretical: 668.89, measured: 668 g / mol)

[1069] [Synthesis Example 147] Synthesis of S-3

[1070]

[1071] The same procedure as in Synthesis Example 145 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 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 65%).

[1072] Mass (theoretical: 734.93, measured: 734 g / mol)

[1073] [Synthesis Example 148] Synthesis of S-4

[1074]

[1075] The same procedure as in Synthesis Example 145 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-4 (9.3 g, yield 70%).

[1076] Mass (theoretical: 734.93, measured: 734 g / mol)

[1077] [Synthesis Example 149] Synthesis of S-5

[1078]

[1079] The same procedure as in Synthesis Example 145 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-5 (8.9 g, yield 67%).

[1080] Mass (theoretical: 734.93, measured: 734 g / mol)

[1081] [Synthesis Example 150] Synthesis of S-6

[1082]

[1083] The same procedure as in Synthesis Example 145 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-6 (9.5 g, yield 65%).

[1084] Mass (theoretical: 811.03, measured: 811 g / mol)

[1085] [Synthesis Example 151] Synthesis of S-7

[1086]

[1087] The same procedure as in Synthesis Example 145 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-7 (10.4 g, yield 71%).

[1088] Mass (theoretical: 811.03, measured: 811 g / mol)

[1089] [Synthesis Example 152] Synthesis of S-8

[1090]

[1091] The same procedure as in Synthesis Example 145 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound S-8 (10.7 g, yield 73%).

[1092] Mass (theoretical: 811.03, measured: 811 g / mol)

[1093] [Synthesis Example 153] Synthesis of T-1

[1094]

[1095] Under a nitrogen stream, DDB-20 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.2 g, 45.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1096] 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 = 4:1 (v / v)) to obtain the target compound T-1 (7.6 g, yield 64%).

[1097] Mass (theoretical: 658.83, measured: 658 g / mol)

[1098] [Synthesis Example 154] Synthesis of T-2

[1099]

[1100] The same procedure as in Synthesis Example 153 was followed except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (6.0 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-2 (8.0 g, yield 66%).

[1101] Mass (theoretical: 668.89, measured: 668 g / mol)

[1102] [Synthesis Example 155] Synthesis of T-3

[1103]

[1104] The same procedure as in Synthesis Example 153 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-3 (8.8 g, yield 66%).

[1105] Mass (theoretical: 734.93, measured: 734 g / mol)

[1106] [Synthesis Example 156] Synthesis of T-4

[1107]

[1108] The same procedure as in Synthesis Example 153 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-4 (8.6 g, yield 65%).

[1109] Mass (theoretical: 734.93, measured: 734 g / mol)

[1110] [Synthesis Example 157] Synthesis of T-5

[1111]

[1112] The same procedure as in Synthesis Example 153 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-5 (9.3 g, yield 70%).

[1113] Mass (theoretical: 734.93, measured: 734 g / mol)

[1114] [Synthesis Example 158] Synthesis of T-6

[1115]

[1116] The same procedure as in Synthesis Example 153 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-6 (10.7 g, yield 73%).

[1117] Mass (theoretical: 811.03, measured: 811 g / mol)

[1118] [Synthesis Example 159] Synthesis of T-7

[1119]

[1120] The same procedure as in Synthesis Example 153 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-7 (10.0 g, yield 68%).

[1121] Mass (theoretical: 811.03, measured: 811 g / mol)

[1122] [Synthesis Example 160] Synthesis of T-8

[1123]

[1124] The same procedure as in Synthesis Example 153 was followed except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (9.1 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound T-8 (10.4 g, yield 71%).

[1125] Mass (theoretical: 811.03, measured: 811 g / mol)

[1126] [Synthesis Example 161] Synthesis of U-1

[1127]

[1128] Under a nitrogen stream, DDB-21 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1129] 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 = 4:1 (v / v)) to obtain the target compound U-1 (8.1 g, yield 68%).

[1130] Mass (theoretical: 641.73, measured: 641 g / mol)

[1131] [Synthesis Example 162] Synthesis of U-2

[1132]

[1133] The same procedure as in Synthesis Example 161 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound U-2 (8.6 g, yield 64%).

[1134] Mass (theoretical: 717.83, measured: 717 g / mol)

[1135] [Synthesis Example 163] Synthesis of U-3

[1136]

[1137] The same procedure as in Synthesis Example 161 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound U-3 (8.8 g, yield 66%).

[1138] Mass (theoretical: 717.83, measured: 717 g / mol)

[1139] [Synthesis Example 164] Synthesis of U-4

[1140]

[1141] The same procedure as in Synthesis Example 161 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound U-4 (8.4 g, yield 63%).

[1142] Mass (theoretical: 717.83, measured: 717 g / mol)

[1143] [Synthesis Example 165] Synthesis of V-1

[1144]

[1145] Under a nitrogen stream, DDB-22 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1146] 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 = 4:1 (v / v)) to obtain the target compound V-1 (8.5 g, yield 71%).

[1147] Mass (theoretical: 641.73, measured: 641 g / mol)

[1148] [Synthesis Example 166] Synthesis of V-2

[1149]

[1150] The same procedure as in Synthesis Example 165 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound V-2 (9.6 g, yield 72%).

[1151] Mass (theoretical: 717.83, measured: 717 g / mol)

[1152] [Synthesis Example 167] Synthesis of V-3

[1153]

[1154] The same procedure as in Synthesis Example 165 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound V-3 (9.1 g, yield 68%).

[1155] Mass (theoretical: 717.83, measured: 717 g / mol)

[1156] [Synthesis Example 168] Synthesis of V-4

[1157]

[1158] The same procedure as in Synthesis Example 165 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound V-4 (8.7 g, yield 65%).

[1159] Mass (theoretical: 717.83, measured: 717 g / mol)

[1160] [Synthesis Example 169] Synthesis of W-1

[1161]

[1162] Under a nitrogen stream, DDB-23 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1163] 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 = 4:1 (v / v)) to obtain the target compound W-1 (7.4 g, yield 62%).

[1164] Mass (theoretical: 641.73, measured: 641 g / mol)

[1165] [Synthesis Example 170] Synthesis of W-2

[1166]

[1167] The same procedure as in Synthesis Example 169 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound W-2 (9.0 g, yield 67%).

[1168] Mass (theoretical: 717.83, measured: 717 g / mol)

[1169] [Synthesis Example 171] Synthesis of W-3

[1170]

[1171] The same procedure as in Synthesis Example 169 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound W-3 ​​(8.6 g, yield 64%).

[1172] Mass (theoretical: 717.83, measured: 717 g / mol)

[1173] [Synthesis Example 172] Synthesis of W-4

[1174]

[1175] The same procedure as in Synthesis Example 169 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound W-4 (8.8 g, yield 66%).

[1176] Mass (theoretical: 717.83, measured: 717 g / mol)

[1177] [Synthesis Example 173] Synthesis of X-1

[1178]

[1179] Under a nitrogen stream, DDB-24 (10.0 g, 18.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.4 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), K2CO3 (6.4 g, 46.6 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1180] 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:EA = 4:1 (v / v)) to obtain the target compound X-1 (8.6 g, yield 72%).

[1181] Mass (theoretical: 641.73, measured: 641 g / mol)

[1182] [Synthesis Example 174] Synthesis of X-2

[1183]

[1184] The same procedure as in Synthesis Example 173 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound X-2 (8.6 g, yield 64%).

[1185] Mass (theoretical: 717.83, measured: 717 g / mol)

[1186] [Synthesis Example 175] Synthesis of X-3

[1187]

[1188] The same procedure as in Synthesis Example 173 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound X-3 (8.0 g, yield 60%).

[1189] Mass (theoretical: 717.83, measured: 717 g / mol)

[1190] [Synthesis Example 176] Synthesis of X-4

[1191]

[1192] The same procedure as in Synthesis Example 173 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.7 g, 22.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound X-4 (9.4 g, yield 70%).

[1193] Mass (theoretical: 717.83, measured: 717 g / mol)

[1194] [Synthesis Example 177] Synthesis of Y-1

[1195]

[1196] Under a nitrogen stream, DDB-25 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.3 g, 45.3 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1197] 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 = 4:1 (v / v)) to obtain the target compound Y-1 (7.7 g, yield 65%).

[1198] Mass (theoretical: 657.79, measured: 657 g / mol)

[1199] [Synthesis Example 178] Synthesis of Y-2

[1200]

[1201] The same procedure as in Synthesis Example 177 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Y-2 (8.2 g, yield 62%).

[1202] Mass (theoretical: 733.89, measured: 733 g / mol)

[1203] [Synthesis Example 179] Synthesis of Y-3

[1204]

[1205] The same procedure as in Synthesis Example 177 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Y-3 (8.9 g, yield 67%).

[1206] Mass (theoretical: 733.89, measured: 733 g / mol)

[1207] [Synthesis Example 180] Synthesis of Y-4

[1208]

[1209] The same procedure as in Synthesis Example 177 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Y-4 (8.4 g, yield 63%).

[1210] Mass (theoretical: 733.89, measured: 733 g / mol)

[1211] [Synthesis Example 181] Synthesis of Z-1

[1212]

[1213] Under a nitrogen atmosphere, DDB-26 (10.0 g, 18.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8 g, 21.7 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), K2CO3 (6.3 g, 45.3 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120°C for 4 h.

[1214] 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 = 4:1 (v / v)) to obtain the target compound Z-1 (8.3 g, yield 70%).

[1215] Mass (theoretical: 657.79, measured: 657 g / mol)

[1216] [Synthesis Example 182] Synthesis of Z-2

[1217]

[1218] The same procedure as in Synthesis Example 181 was followed except that 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Z-2 (8.6 g, yield 65%).

[1219] Mass (theoretical: 733.89, measured: 733 g / mol)

[1220] [Synthesis Example 183] Synthesis of Z-3

[1221]

[1222] The same procedure as in Synthesis Example 181 was followed except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Z-3 (8.2 g, yield 62%).

[1223] Mass (theoretical: 733.89, measured: 733 g / mol)

[1224] [Synthesis Example 184] Synthesis of Z-4

[1225]

[1226] The same procedure as in Synthesis Example 181 was followed except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.5 g, 21.7 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to obtain the target compound Z-4 (8.5 g, yield 64%).

[1227] Mass (theoretical: 733.89, measured: 733 g / mol)

[1228] [Synthesis Example 185] Synthesis of ZA-1

[1229]

[1230] Under a nitrogen stream, DDB-27 (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.

[1231] 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 = 4:1 (v / v)) to obtain the target compound ZA-1 (8.3 g, yield 71%).

[1232] Mass (theoretical: 717.83, measured: 717 g / mol)

[1233] [Synthesis Example 186] Synthesis of ZA-2

[1234]

[1235] The same procedure as in Synthesis Example 185 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 ZA-2 (8.4 g, yield 65%).

[1236] Mass (theoretical: 793.93, measured: 793 g / mol)

[1237] [Synthesis Example 187] Synthesis of ZA-3

[1238]

[1239] The same procedure as in Synthesis Example 185 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 ZA-3 (8.2 g, yield 63%).

[1240] Mass (theoretical: 793.93, measured: 793 g / mol)

[1241] [Synthesis Example 188] Synthesis of ZA-4

[1242]

[1243] The same procedure as in Synthesis Example 185 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 ZA-4 (8.8 g, yield 68%).

[1244] Mass (theoretical: 793.93, measured: 793 g / mol)

[1245]

[1246] [Example 1] Fabrication of a green organic EL device

[1247] 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.

[1248] First, a glass substrate coated with a 1500 Å thick ITO (Indium Tin Oxide) film 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.

[1249] An organic EL device was fabricated by stacking HT + 2% PA (100 Å) / HT (1200 Å) / HA (300 Å) / 60% compound A-1 + 30% compound HPGH + 10% Ir(ppy)3(400 Å) / EA (50 Å) / ET + LiQ (300 Å_1:1) / LiF (10 Å) / Al (1000 Å) in that order on the prepared ITO transparent electrode.

[1250] At this time, the structures of the compounds HT, HA, PA, HPGH, Ir(ppy)3, EA, and ET used are as follows, respectively.

[1251]

[1252]

[1253] [Example 2] ~ [Example 188] Manufacturing of green organic EL device

[1254] A green organic EL device was manufactured in the same manner as in Example 1, except that Compounds A-2 to ZA-4 described in Table 1 were used instead of Compound A-1, which was used as the first host among the light-emitting host materials when forming the light-emitting layer in Example 1.

[1255]

[1256] [Comparative Example 1] ~ [Comparative Example 3] Fabrication of a green organic EL device

[1257] A green organic EL device was manufactured using the same process as Example 1, except that ET-1, ET-2, and ET-3 were used instead of Compound A-1 as the luminescent host material when forming the luminescent layer in Example 1.

[1258] The structures of compounds ET-1, ET-2, and ET-3 used in Comparative Examples 1 to 3 are as follows, respectively.

[1259]

[1260]

[1261] [Evaluation Example 1]

[1262] For the green organic EL devices manufactured in Examples 1 to 188 and Comparative Examples 1 to 3, the driving voltage, current efficiency, luminescence peak, and lifespan at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[1263] Sample 1 Host driving voltage EL peak current efficiency life (V) (nm) (cd / A) (hr, T 97) Example 1A-13.8451764.1380 Example 2A-23.6551865.3384 Example 3A-33.7451763.2382 Example 4A-43.6551566.3384 Example 5A-53.7551864.2375 Example 6A-63.8951863.4374 Example 7A-73.7751761.2371 Example 8A-83.7151560.4384 Example 9B-13.6851862.3382 Example 10B-23.6651866.5385 Example 11B-33.8951763.2377 Example 12B-43.9851562.4374 Example 13B-53.7151865.5372 Example 14B-63.7551867.2371 Example 15B-73.6551768.1379 Example 16B-83.7451566.4372 Example 17C-13.6651864.1373 Example 18C-23.6151866.4382 Example 19C-33.6451862.1389 Example 20C-43.8451763.4382 Example 21C-53.6751564.3381 Example 22C-63.6851867.8384 Example 23C-73.7151865.1381 Example 24C-83.6651563.4388 Example 25D-13.9151864.4380 Example 26D-23.9251862.2384 Example 27D-33.9151862.8381 Example 28D-43.8251765.3381 Example 29D-53.8851566.3384 Example 30D-63.8251563.1386 Example 31D-73.7451861.9381 Example 32D-83.7451862.7384 Example 33E-13.6551765.3384 Example 34E-23.7551562.4381 Example 35E-33.8951863.4371 Example 36E-43.7751564.2379 Example 37E-53.7151464.3378 Example 38E-63.6851563.2372 Example 39E-73.6651866.3373 Example 40E-83.8951964.2377 Example 41F-13.9851163.4376 Example 42F-23.7151561.2375 Example 43F-33.7552060.4379 Example 44F-43.6551162.3381 Example 45F-53.7451466.5374 Example 46F-63.6651563.2385 Example 47F-73.6151562.4380 Example 48F-83.8451865.5384 Example 49G-13.5851368.3399 Example 50G-23.5451868.2393 Example 51G-33.5351568.6391 Example 52G-43.5851868.1401 Example 53G-53.5951868.4400 Example 54G-63.5251768.8403 Example 55G-73.5551568.9392 Example 56G-83.5151568.1394 Example 57H-13.6651861.2373 Example 58H-23.8951860.4382 Example 59H-33.9851162.3389 Example 60H-43.6651466.5382 Example 61H-53.8951563.2381 Example 62H-63.9851562.4384 Example 63H-73.7151865.5381 Example 64H-83.7551167.2388 Example 65I-13.5151468.1391 Example 66I-23.5251568.3392 Example 67I-33.5551568.3391 Example 68I-43.5351868.7390 Example 69I-53.5251368.3393 Example 70I-63.5151868.2392 Example 71I-73.5751568.1392 Example 72I-83.5851868.2390 Example 73J-13.7151765.1384 Example 74J-23.6651763.4381 Example 75J-33.9151564.4371 Example 76J-43.6751862.2381 Example 77J-53.6851762.8384 Example 78J-63.7151865.3386 Example 79J-73.6651766.3381 Example 80J-83.9151563.1384 Example 81K-13.9251361.9384 Example 82K-23.9151462.7381 Example 83K-33.8251565.3371 Example 84K-43.8851662.4379 Example 85K-53.8251163.4378 Example 86K-63.7451564.2372 Example 87K-73.7452064.3373 Example 88K-83.6551163.2377 Example 89L-13.7551466.3376 Example 90L-23.8951564.2375 Example 91L-33.7751563.4379 Example 92L-43.7151861.2381 Example 93L-53.6851360.4374 Example 94L-63.8951862.3385 Example 95L-73.7751566.5380 Example 96L-83.7151863.2384 Example 97M-13.6851862.4382 Example 98M-23.6651765.5385 Example 99M-33.8951567.8377 Example 100M-43.9851565.1374 Example 101M-53.7151863.4372 Example 102M-63.7551164.4371 Example 103M-73.6551462.2379 Example 104M-83.7451562.8372 Example 105N-13.6651565.3373 Example 106N-23.6151866.3382 Example 107N-33.8451363.1389 Example 108N-43.6551861.9382 Example 109N-53.7451562.7381 Example 110N-63.6551865.3384 Example 111N-73.7551762.4381 Example 112N-83.8951763.4374 Example 113O-13.7751564.2372 Example 114O-23.7151864.3371 Example 115O-33.6851763.2379 Example 116O-43.6651866.3372 Example 117O-53.8951764.2373 Example 118O-63.6651563.4382 Example 119O-73.6151363.2389 Example 120O-83.8451462.4382 Example 121P-13.6551565.5381 Example 122P-23.7451667.2384 Example 123P-33.6551168.1381 Example 124P-43.7551566.4388 Example 125P-53.8952064.1380 Example 126P-63.7751163.2384 Example 127P-73.7151466.3381 Example 128P-83.6851564.2381 Example 129Q-13.6651563.4384 Example 130Q-23.8951861.2386 Example 131Q-33.9851360.4381 Example 132Q-43.6651862.3384 Example 133Q-53.8951566.5384 Example 134Q-63.9851863.2381 Example 135Q-73.7151862.4371 Example 136Q-83.7551765.5381 Example 137R-13.6551567.2384 Example 138R-23.7451568.1386 Example 139R-33.9851866.4381 Example 140R-43.7151164.1384 Example 141R-53.7551466.4384 Example 142R-63.6551562.1381 Example 143R-73.7451563.4389 Example 144R-83.9851864.3382 Example 145S-13.3551769.3450 Example 146S-23.3851769.2451 Example 147S-33.3851570.1463 Example 148S-43.3651870.2464 Example 149S-53.3451769.9461 Example 150S-63.4151869.8451 Example 151S-73.3151769.5451 Example 152S-83.3651569.6455 Example 153T-13.3951369.4444 Example 154T-23.3851470.1439 Example 155T-33.3751569.4438 Example 156T-43.3651669.3441 Example 157T-53.3651169.3433 Example 158T-63.3451569.1430 Example 159T-73.3252069.4441 Example 160T-83.3751169.2431 Example 161U-13.7551160.4375 Example 162U-23.8951462.3379 Example 163U-33.7751566.5381 Example 164U-43.7151563.2374 Example 165V-13.6851862.4385 Example 166V-23.6651365.5380 Example 167V-33.8951868.3384 Example 168V-43.9851568.2399 Example 169W-13.7151868.6393 Example 170W-23.7551868.1391 Example 171W-33.6551768.4401 Example 172W-43.7451568.8400 Example 173X-13.6651568.9403 Example 174X-23.6151868.1392 Example 175X-33.8451861.2394 Example 176X-43.5851160.4373 Example 177Y-13.5451862.3382 Example 178Y-23.5351866.5389 Example 179Y-33.5851863.2389 Example 180Y-43.5951562.4382 Example 181Z-13.5251865.5381 Example 182Z-23.5551767.2384 Example 183Z-33.5151768.1381 Example 184Z-43.6651568.3375 Example 185ZA-13.8951868.3379 Example 186ZA-23.9851768.7381 Example 187ZA-33.6651868.3374 Example 188ZA-43.8951768.2385 Comparative Example 1ET-15.0151444.3301 Comparative Example 2ET-24.9851542.1298 Comparative Example 3ET-34.8151543.4299.

[1264]

[1265] As shown in Table 1 above, the green organic EL devices of Examples 1 to 188 using the compounds (A-1 to ZA-4) according to the present invention as light-emitting layer materials of green organic EL devices were found to exhibit superior performance in terms of efficiency, driving voltage, and lifespan characteristics compared to the green organic EL devices of Comparative Examples 1 to 3 each including compounds ET-1, ET-2, and ET-3 containing heteroatom-containing moieties as Ar1, Ar2, and Ar3 of Chemical Formula 1 as light-emitting layer materials. It is presumed that when a heteroatom-containing moiety is introduced as Ar1, Ar2, and Ar3 of chemical formula 1, the unshared electron pair present in the heteroatom is used as another migration path for holes that should be transferred through the phosphorescent green host (HPGH), and this causes a loss equivalent to the number of holes transferred through another migration path when forming excitons in the light-emitting layer.

[1266] In view of the above, it was confirmed that the compound according to the present invention can increase stability against injected electrons by introducing a heteroatom-free moiety, specifically an aryl group, as Ar1, Ar2, and Ar3, and thus is more advantageous in terms of overall characteristics of the device.

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 CR 4 or N, and just 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 each is independently O or S, Ar 1 Inland Ar 3 are identical or different from each other, and each independently represents hydrogen, deuterium (D), and C. 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 alkynyl group of , and C 6 ~C 60 is selected from the group consisting of aryl groups, or they can be combined with any adjacent group to form a condensed ring, provided that Ar 1 This hydrogen case is excluded, R 1 Inland R 4 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 , and C 6 ~C 60 is selected from the group consisting of aryl groups, or these can combine with any adjacent groups to form a condensed ring, o is an integer from 0 to 3, p and q are each independently an integer from 0 to 5, Above Ar 1 Inland Ar 3 , R 1 Inland R 4 The alkyl group, alkenyl group, alkynyl group, and aryl group of each independently represent 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, The compound represented by the above chemical formula 1 contains at least three heteroatoms selected from the group consisting of N, O and S, Ar 1 Inland Ar 3 A compound which does not contain a heteroatom-containing moiety.

3. In paragraph 1, Above X 1 Inland X 3 The compound is one of the following structural formulas: In the above formula, * indicates a part connected to the chemical formula 1 above, Ar 2 , Ar 3 , R 2 , R 3 , p and q are as defined in Article 1, respectively.

4. In paragraph 1, Y 1 and Y 2 are compounds that are identical to each other.

5. In paragraph 1, Ar 1 Silver C 6 ~C 20 is the aryl group of Ar 2 and Ar 3 are identical or different from each other, and each independently represents hydrogen, deuterium (D), or C. 6 ~C 40 is the aryl group of Above Ar 1 Inland Ar 3 A compound in which each aryl group is independently substituted or unsubstituted with deuterium (D).

6. In paragraph 1, Ar 1 A compound selected from the following structural formulas: In the above formula, * indicates a part connected to the above chemical formula 1.

7. In paragraph 1, Ar 2 and Ar 3 are identical or different from each other, and each independently is a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the above chemical formula 1.

8. In paragraph 1, R 1 Inland R 4 are identical or different from each other, and each independently represents hydrogen, deuterium (D), and C. 1 ~C 40 alkyl group of, and C 6 ~C 40 A compound selected from the group consisting of aryl groups.

9. 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 above formula, X 1 Inland X 3 , Ar 1 Inland Ar 3 , R 1 , or R 3 , o, p and q are as defined in paragraph 1, respectively.

10. 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 above formula, X 1 Inland X 3 , Y 1 , Y 2 , Ar 1 Inland Ar 3 , R 1 , or R 3 , o, p and q are as defined in paragraph 1, respectively.

11. 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 formula, X 1 Inland X 3 , Y 1 , Y 2 , Ar 1 Inland Ar 3 , R 1 , or R 3 , o, p and q are as defined in paragraph 1, respectively.

12. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 14 to 17: [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] In the above formula, X 1 Inland X 3 , Y 1 , Y 2 , Ar 1 Inland Ar 3 , R 1 , or R 3 , o, p and q are as defined in paragraph 1, respectively.

13. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 18 to 21: [Chemical Formula 18] [Chemical Formula 19] [Chemical formula 20] [Chemical Formula 21] In the above formula, X 1 Inland X 3 , Y 1 , Y 2 , Ar 1 Inland Ar 3 , R 1 , or R 3 , o, p and q are as defined in paragraph 1, respectively.

14. 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.

15. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds A-1 to ZA-4 below.

16. 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 one or more layers comprises a compound according to any one of claims 1 to 15.

17. In paragraph 16, 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 of the chemical formula 1 as a host.

18. In paragraph 17, An organic electroluminescent device, wherein the light-emitting layer further comprises at least one of a P-type host material, an N-type host material, a fluorescent light-emitting dopant, and a phosphorescent light-emitting dopant.

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