Organic light-emitting compounds and organic electroluminescent devices containing the same

Abstract

The present invention relates to a novel organic light-emitting compound represented by chemical formula 1 and an organic electroluminescent device containing the same, which can have high current efficiency and a low driving voltage. [Chemical formula 1] [Formula 1] TIFF2026510145000270.tif34170

Description

[Technical Field]

[0001] [Cross-citation with related applications]

[0002] This application claims priority based on Korean Patent Application No. 10-2023-0186800 dated December 20, 2023, and all content disclosed in the said Korean Patent Application is incorporated herein by reference.

[0003] [Technical field]

[0004] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device containing the same. [Background technology]

[0005] Beginning with Bernanos' observations of organic thin-film luminescence in the 1950s, research on organic electroluminescent (EL) devices based on blue electroluminescence using anthracene single crystals continued in 1965. In 1987, Tang presented an organic electroluminescent device with a multilayer structure divided into a hole layer and a luminescent layer. Subsequently, in order to create highly efficient and long-lived organic electroluminescent devices, the technology evolved to incorporate characteristic organic layers within the device, leading to the development of specialized materials used in this process.

[0006] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the positive electrode and electrons are injected into the organic layer at the negative electrode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton falls back to the ground state. The materials used in the organic layer can be classified according to their function into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0007] The light-emitting materials for organic electroluminescent devices can be classified into blue, green, and red light-emitting materials according to their emission color. In addition, yellow and orange light-emitting materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as light-emitting materials to increase color purity and luminescence efficiency through energy transfer.

[0008] Dopant materials can be divided into fluorescent dopants, which use organic materials, and phosphorescent dopants, which use metal complex compounds containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, so research is progressing not only on phosphorescent dopants but also on phosphorescent host materials.

[0009] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as materials for light-emitting layers. In particular, among light-emitting layer materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0010] Thus, while conventional organic layer materials are advantageous in terms of luminescence properties, their low glass transition temperature and poor thermal stability mean they do not meet the requirements for satisfactory lifespan in organic electroluminescent devices.

[0011] Therefore, there is a need for the development of high-performance organic layer materials. [Prior art documents] [Patent Documents]

[0012] [Patent Document 1] Korean Published Patent Publication No. 10-2015-0069346 [Overview of the project] [Problems that the invention aims to solve]

[0013] The present invention aims to provide novel compounds and their applications that can be used as organic layer materials for organic electroluminescent devices, specifically electron transport layer materials and electron transport auxiliary layer materials, exhibiting excellent thermal stability, electron injection and transfer capabilities, and luminescence.

[0014] Furthermore, the present invention aims to provide an organic electroluminescent device that includes the novel organic light-emitting compound described above and exhibits significant improvements in terms of light-emitting performance, driving voltage, lifespan, and efficiency.

[0015] The problems that this invention aims to solve are not limited to those mentioned above, and other problems not mentioned can be clearly understood by an ordinary person from the following description. [Means for solving the problem]

[0016] To solve the above-mentioned problems, the present invention provides an organic luminescent compound represented by the following chemical formula 1.

[0017] Organic luminescent compounds represented by the following chemical formula 1:

[0018] [Chemical formula 1] [ka]

[0019] In the aforementioned chemical formula 1,

[0020] One of X1 through X4 is C-(L2) c-R2, the remainder are independently N or CR, two or more of X1 to X4 are N, and R is hydrogen, a C1 to C40 alkyl group, a C6 to C60 aryl group, or a C2 to C60 heteroaryl group, each of which is unsubstituted or substituted.

[0021] R1 and R2 are independently hydrogen, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C3-C40 cycloalkyl group, a C1-C40 heterocycloalkyl group, a C1-C40 alkyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a C1-C40 alkylsilyl group, a C6-C60 arylsilyl group, a C1-C40 alkylboron group, a C6-C60 arylboron group, a C6-C60 arylphosphine group, a C1-C40 alkylphosphine oxide group, a C6-C60 arylphosphine oxide group, a C1-C40 alkylamine group, or a C6-C60 arylamine group, and each of these may be unsubstituted or substituted.

[0022] L1 to L3 are each independently single bonds, arylene groups having 6 to 60 carbon atoms, or heteroarylene groups having 2 to 60 carbon atoms, and each of these may be unsubstituted or substituted.

[0023] R3 and R4 are, independently, an aryl group having 6 to 60 carbon atoms substituted with a cyano group, an aryl group having 6 to 60 carbon atoms substituted with a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, deuterium, or a cyano group, each of which may be unsubstituted or substituted.

[0024] a through c are each independent integers from 0 to 5.

[0025] d is an integer between 0 and 3, and e is an integer between 0 and 4, where d + e ≥ 1.

[0026] Furthermore, the present invention provides an organic electroluminescent element containing the organic light-emitting compound.

[0027] Furthermore, the present invention provides applications for the above-mentioned organic light-emitting compounds in organic electroluminescent devices. [Effects of the Invention]

[0028] The organic light-emitting compound according to the present invention contains an azine group, which is a strong electron acceptor in its molecular structure, and has excellent electron injection and transfer capabilities. By improving the electron transfer capability to the light-emitting layer, the driving voltage of the device can be improved.

[0029] Furthermore, the organic light-emitting compound according to the present invention contains aromatic hydrocarbon groups and condensed structures, rather than simple aliphatic ring groups, and exhibits excellent thermal stability. Since there is no crystallization temperature (Tc), it is effective in improving not only the processability of the device but also its lifespan.

[0030] Furthermore, the organic light-emitting compound according to the present invention has a structure in which a cyclohexylfluorene group substituted with a cyano group or a pyridine group and an azine moiety are linked at the ortho position via a linker. This improves stability and simultaneously increases the dipole moment, thereby enhancing the interaction with the cathode and improving electron generation within the device, thus effectively improving the drive voltage characteristics.

[0031] Furthermore, the organic electroluminescent element containing the organic light-emitting compound according to the present invention can achieve a low driving voltage and significantly improve light-emitting performance, lifespan, and efficiency, thereby enabling more effective application in full-color display panels and the like.

[0032] The effects of the present invention are not limited to those mentioned above, and other effects not mentioned can be clearly understood by an ordinary person of the art from the following description. [Modes for carrying out the invention]

[0033] The advantages and features of the present invention, and the methods for achieving them, will become clear by referring to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below, but can be embodied in a variety of different forms, provided that these embodiments are provided to complete the disclosure of the present invention and to fully inform a person ordinary in the art to which the present invention pertains, and the present invention is defined only by the scope of the claims.

[0034] The terms used herein are for illustrative purposes only and are not intended to limit the invention. In this specification, singular forms include plural forms unless otherwise specified. The terms “comprises” and / or “comprising” as used in this specification do not preclude the presence or addition of one or more other components beyond those mentioned.

[0035] Unless otherwise defined, all terms used herein (including technical and scientific terms) may be used in a sense that is commonly understood by an ordinary person skilled in the art to which the present invention pertains. Furthermore, each commonly used predefined term should not be interpreted ideally or excessively unless explicitly defined otherwise.

[0036] Embodiments of the present invention will be described in detail below.

[0037] Before proceeding, the meanings of the terms used herein will be briefly explained. However, it should be noted that these explanations are for the purpose of facilitating understanding of this specification and are not used to limit the technical ideas of the invention unless explicitly stated as limiting features.

[0038] In the present invention, the term "aryl group" may mean a monovalent functional group derived from an aromatic hydrocarbon. The aforementioned aryl groups include, for example, phenyl group, naphthyl group, anthracenyl group, naphthacenyl group, pyrenyl group, tolyl group, biphenyl group, terphenyl group, triphenylenyl group, chrysenyl group, spirobifluorenyl group, fluoranthenyl group, fluorenyl group, perylenyl group, indenyl group, azulenyl group, heptalenyl group, and phenalenyl group, and phenanthrenyl group. The term "arylene group" can mean, but is not limited to, a group of, or other similar terms. Furthermore, the term "arylene group" can refer to a divalent functional group derived from aromatic hydrocarbons.

[0039] In the present invention, the term "heteroaryl group" can mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or fused ring structure, and the heteroaryl group may contain, in addition to carbon atoms, at least one heteroatom from among nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). Specific examples of the aforementioned heteroaryl groups include pyrrolyl group, pyridyl group, pyridazinyl group, triazinyl group, pyrimidinyl group, pyrazinyl group, naphthyridyl group, acenaphthopyridyl group, triazolyl group, tetrazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indolyl group, isoindolyl group, and indolizinyl group. group), purinyl group, indazolyl group, quinolyl group, benzoquinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl groupNitrogen-containing heteroaryl groups including acridinyl group, phenanthridyl group, carbazolyl group, phenanthrolinyl group, phenazinyl group, imidazopyridyl group, imidazopyrimidinyl group, pyrazolopyridyl group, heptaazaphenalenyl group, etc.; sulfur-containing heteroaryl groups including thienyl group, benzothiophenyl group, dibenzothiophenyl group, benzonaphthothiophenyl group, etc.; furyl group, pyranyl group Oxygen-containing heteroaryl groups including benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzonaphthofuranyl group, oxanthrenyl group, xanthenyl group, benzoxanthenyl group, etc.; thiadiazolyl group, oxadiazolyl group, phenoxathiinyl group, benzothienopyrimidinyl group, benzofuropyridyl groupExamples include heteroaryl groups containing oxygen and sulfur complexes (group 5, 6, 7, 8, 9

[0040] In the present invention, the term "alkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon having a linear or branched structure.The alkyl groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, 2-ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group, and 1,1,2-trimethylpropyl group. This may mean, but is not limited to, groups such as 1-propylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group, and 3-methylpentyl group.

[0041] In the present invention, the term "cycloalkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon with a cyclic structure. The cycloalkyl group may be, but is not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclononyl group, or an adamantyl group.

[0042] In the present invention, the term "heterocycloalkyl group" can mean a monovalent functional group derived from a saturated hydrocarbon with a cyclic structure, and the heterocycloalkyl group may contain, in addition to carbon atoms, at least one heteroatom from nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). The heterocycloalkyl group may be defined using the number of nuclear atoms instead of the number of carbon atoms, where the number of nuclear atoms may mean the number of atoms containing, together with carbon (C) atoms, one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heterocycloalkyl group may have a number of nuclear atoms of 5 to 60, 5 to 30, or 5 to 20.

[0043] In the present invention, the term "alkenyl group" may mean a monovalent functional group derived from hydrocarbons containing one or more carbon double bonds in the middle or terminal of an alkyl group.

[0044] In the present invention, the term "alkynyl group" may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon triple bonds in the middle or terminal of an alkyl group.

[0045] In the present invention, the terms "alkylsilyl group" and "arylsilyl group" may mean a monovalent functional group derived from a compound in which one or more hydrogen atoms of a silane are substituted with the alkyl or aryl groups described above, respectively.

[0046] In the present invention, "alkylamine group" and "arylamine group" may mean a monovalent functional group derived from a compound in which one or more hydrogen atoms of an amine are substituted with the aforementioned alkyl or aryl group, respectively.

[0047] In the present invention, the terms "alkylboron group" and "arylboron group" may mean a monovalent functional group derived from a compound in which one or more hydrogen atoms of a borane are substituted with the aforementioned alkyl or aryl groups, respectively.

[0048] In the present invention, "arylphosphine group" may mean a monovalent functional group derived from a compound in which the aryl group described above is substituted for the phosphine.

[0049] In the present invention, the terms "alkylphosphine oxide group" and "arylphosphine oxide group" may mean a monovalent functional group derived from a compound in which the phosphine oxide is substituted with the alkyl group or aryl group described above, respectively.

[0050] In the present invention, the term "substitution" independently refers to deuterium, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C3 to C20 cycloalkyl group, a C1 to C20 heterocycloalkyl group, a C3 to C20 heterocycloalkyl group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C5 to C30 heteroaryl group, a C1 to C20 alkylsilyl group, and a C6 to C30 group. This means that the substituents are substituted with one or more substituents selected from the group consisting of arylsilyl groups, alkylboron groups having 1 to 20 carbon atoms, arylboron groups having 6 to 30 carbon atoms, arylphosphine groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, alkylamine groups having 1 to 20 carbon atoms, and arylamine groups having 6 to 30 carbon atoms. When substituted with multiple substituents, these substituents may be the same or different from each other.

[0051] <Organoluminescent Compounds>

[0052] The present invention provides a novel organic luminescent compound. The organic luminescent compound of the present invention is represented by the following chemical formula 1.

[0053] [Chemical formula 1] [ka]

[0054] In the aforementioned chemical formula 1,

[0055] One of X1 through X4 is C-(L2) c -R2, the remainder are independently N or CR, two or more of X1 to X4 are N, and R is hydrogen, a C1 to C40 alkyl group, a C6 to C60 aryl group, a C2 to C60 heteroaryl group, or a C5 to C60 heteroaryl group, each of which is unsubstituted or substituted.

[0056] R1 and R2 are independently hydrogen, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C3-C40 cycloalkyl group, a C1-C40 heterocycloalkyl group, a C3-C40 heterocycloalkyl group, a C1-C40 alkyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a C5-C60 heteroaryl group, a C1-C40 alkylsilyl group, a C6-C60 arylsilyl group, a C1-C40 alkylboron group, a C6-C60 arylboron group, a C6-C60 arylphosphine group, a C1-C40 alkylphosphine oxide group, a C6-C60 arylphosphine oxide group, a C1-C40 alkylamine group, or a C6-C60 arylamine group, and each of these may be unsubstituted or substituted.

[0057] L1 to L3 are each independently a single bond, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, or a heteroarylene group having 5 to 60 nuclear atoms, and each of these is either unsubstituted or substituted.

[0058] R3 and R4 are, independently, an aryl group having 6 to 60 carbon atoms substituted with a cyano group, an aryl group having 6 to 60 carbon atoms substituted with a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms substituted with a nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms, a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nitrogen-containing nuclear atoms, deuterium, or a cyano group, each of which may be unsubstituted or substituted.

[0059] a through c are each independent integers from 0 to 5.

[0060] d is an integer between 0 and 3, and e is an integer between 0 and 4, where d + e ≥ 1.

[0061] If a, b, or c is 0, it means that there is a single bond.

[0062] If d is 0, it means that R4 has not substituted on any hydrogen atoms in the benzene ring that could be substituted with R4. If e is 0, it means that R3 has not substituted on any hydrogen atoms in the benzene ring that could be substituted with R3.

[0063] Specifically, one or more of the following groups that may exist as R, R1 to R4 and L1 to L3 are independently unsubstituted, or deuterium, C2 to C20 alkenyl groups, C2 to C20 alkynyl groups, C3 to C20 cycloalkyl groups, C1 to C20 heterocycloalkyl groups, and C3 to C20 heterocycloalkyl groups. This means that the group is substituted with one or more substituents selected from the group consisting of a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C5-C30 heteroaryl group, a C1-C20 alkylsilyl group, a C6-C30 arylsilyl group, a C1-C20 alkylboron group, a C6-C30 arylboron group, a C6-C30 arylphosphine group, a C1-C20 alkylphosphine oxide group, a C6-C30 arylphosphine oxide group, a C1-C20 alkylamine group, and a C6-C30 arylamine group. If substituted with multiple substituents, these substituents may be identical or different from each other.

[0064] In one example, in the chemical formula 1,

[0065] One of X1 through X4 is C-(L2) c-R2, the remainder are independently N or CR, two or more of the above X1 to X4 are N, and the above R is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms.

[0066] R1 and R2 are each independently an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 1 to 20 carbon atoms, an arylamine group having 1 to 20 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, and these Each of these can be either unsubstituted or substituted with deuterium, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C3-C20 cycloalkyl group, a C1-C20 heterocycloalkyl group, a C3-C20 heterocycloalkyl group, a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C5-C30 heteroaryl group, a C1-C20 alkylsilyl group, a C6-C30 arylsilyl group, a C1-C20 alkylboron group, a C6-C30 arylboron group, a C6-C30 arylphosphine group, a C1-C20 alkylphosphine oxide group, a C6-C30 arylphosphine oxide group, a C1-C20 alkylamine group, or a C6-C30 arylamine group.

[0067] L1 to L3 are each independently single-bonded, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 2 to 30 carbon atoms, or heteroarylene groups with 5 to 30 nuclear atoms.

[0068] R3 and R4 are, independently, an aryl group having 6 to 30 carbon atoms substituted with a cyano group, an aryl group having 6 to 30 carbon atoms substituted with a nitrogen-containing heteroaryl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms substituted with a nitrogen-containing heteroaryl group having 5 to 30 nuclear atoms, a nitrogen-containing heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nitrogen-containing nuclear atoms, deuterium, or a cyano group, and each of these may be unsubstituted or substituted.

[0069] a through c are each independent integers from 0 to 2.

[0070] d is an integer between 0 and 2, and e is an integer between 0 and 2, where d + e ≥ 1.

[0071] If a, b, or c is 0, it means that there is a single bond.

[0072] If d is 0, it means that R4 has not substituted on any hydrogen atoms in the benzene ring that could be substituted with R4. If e is 0, it means that R3 has not substituted on any hydrogen atoms in the benzene ring that could be substituted with R3.

[0073] In one example, in the chemical formula 1,

[0074] One of X1 through X4 is C-(L2) c -R2 is N, and the rest are independently N or CH, with two or more of the above X1 to X4 being N.

[0075] R1 and R2 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, and each of these can be either unsubstituted or substituted with a cycloalkyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms.

[0076] L1 to L3 are each independently single-bonded, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 2 to 30 carbon atoms, or heteroarylene groups with 5 to 30 nuclear atoms.

[0077] R3 and R4 are, independently, aryl groups having 6 to 30 carbon atoms substituted with a cyano group, nitrogen-containing heteroaryl groups having 2 to 30 carbon atoms, nitrogen-containing heteroaryl groups having 5 to 30 nuclear atoms, or cyano groups.

[0078] a through c are each independent integers from 0 to 2.

[0079] d is an integer between 0 and 2, and e is an integer between 0 and 2, where d + e ≥ 1.

[0080] In one example, in the chemical formula 1, a and b may be 0 or 1, c may be 0, d may be 1, and e may be 0.

[0081] In one example, in the chemical formula 1, a and b may be 0 or 1, c may be 0, d may be 0, and e may be 1.

[0082] If a, b, or c is 0, it means that there is a single bond.

[0083] If d is 0, it means that R4 has not substituted on any hydrogen atoms in the benzene ring that can be substituted with R4, and if e is 0, it means that R3 has not substituted on any hydrogen atoms in the benzene ring that can be substituted with R3.

[0084] In one example, the aforementioned chemical formula 1 may be represented by any one selected from the following chemical formulas 2 to 9.

[0085] [Chemical formula 2] [ka]

[0086] [Chemical formula 3] [ka]

[0087] [Chemical formula 4] [ka]

[0088] [Chemical formula 5] [ka]

[0089] [Chemical formula 6] [ka]

[0090] [Chemical formula 7] [ka]

[0091] [Chemical formula 8] [ka]

[0092] [Chemical formula 9] [ka]

[0093] In each of the above chemical formulas 2 to 9,

[0094] R1 and R2 are each independently hydrogen, a carbon-6 to carbon-30 aryl group, a carbon-2 to carbon-30 heteroaryl group, or a carbon-5 to carbon-30 heteroaryl group, each of which is either unsubstituted or substituted with a carbon-3 to carbon-20 cycloalkyl group, a carbon-1 to carbon-20 alkyl group, a carbon-6 to carbon-30 aryl group, a carbon-2 to carbon-30 heteroaryl group, a carbon-5 to carbon-30 heteroaryl group, a carbon-1 to carbon-20 alkylsilyl group, a carbon-6 to carbon-30 arylsilyl group, a carbon-1 to carbon-20 alkylphosphine oxide group, or a carbon-6 to carbon-30 arylphosphine oxide group.

[0095] L1 to L3 are each independently single-bonded, arylene groups with 6 to 30 carbon atoms, heteroarylene groups with 2 to 30 carbon atoms, or heteroarylene groups with 5 to 30 nuclear atoms.

[0096] R3 and R4 are, independently, aryl groups having 6 to 30 carbon atoms substituted with a cyano group, nitrogen-containing heteroaryl groups having 2 to 30 carbon atoms, nitrogen-containing heteroaryl groups having 5 to 30 nuclear atoms, or cyano groups.

[0097] a through c are each independent integers from 0 to 2.

[0098] If a, b, or c is 0, it means that there is a single bond.

[0099] In one embodiment, the aforementioned chemical formula 1 may be represented by any one selected from the following chemical formulas 2 to 7.

[0100] [Chemical formula 2] [ka]

[0101] [Chemical formula 3] [ka]

[0102] [Chemical formula 4] [ka]

[0103] [Chemical formula 5] [ka]

[0104] [Chemical formula 6] [ka]

[0105] [Chemical formula 7] [ka]

[0106] In each of the above chemical formulas 2 to 7,

[0107] R1 and R2 are independently hydrogen, a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorenyl group, a pyridyl group, a carbazolyl group, a dibenzothiophenyl group, or a dibenzofuranyl group, each of which is either unsubstituted or substituted with a methyl group, a phenyl group, a cyclohexyl group, an adamantyl group, a pyridyl group, a carbazolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a trimethylsilyl group, a triphenylsilyl group, a dimethylphosphine oxide group, or a diphenylphosphine oxide group.

[0108] L1 to L3 are each independently a single bond, a phenylene group, a biphenylene group, a naphthylene group, a terphenylene group, a dibenzofuranylene group, or a dibenzothiophenylene group.

[0109] R3 and R4 are each independently substituted with a cyano group, a phenyl group, a pyridyl group, or a cyano group.

[0110] a through c can each be an independent integer between 0 and 2.

[0111] If a, b, or c is 0, it means that there is a single bond.

[0112] In one embodiment, the organic luminescent compound represented by chemical formula 1 may be any one selected from the following compounds 001 to 774.

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] [ka]

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[0127]

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[0129]

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[0130]

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[0131]

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[0132]

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[0133]

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[0134]

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[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140]

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[0141]

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[0142]

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[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] As a specific example, the compounds represented by chemical formula 1 are compounds 006, 010, 014, 022, 026, 030, 038, 042, 046, 054, 058, 062, 070, 074, 078, 086, 090, 094, 102, 106, 110, 118, 122, 126, 134, 138, 142, 150, 154, 158, 166, 170, 174, 182, 186, 190, 198, 202, 206, 214, 218, 222, 230, 234, 238, 246, 250, 254, 262, 266, It may be any one selected from 270, 278, 282, 286, 294, 298, 302, 310, 314, 318, 326, 330, 334, 342, 346, 350, 358, 362, 366, 374, 378, 382, ​​390, 394, 398, 406, 410, 414, 422, 426, 430, 438, 442, 446, 454, 458, 462, 470, 474, 478, 486, 502, 518, 534, 550, 561, 570, 624, 635, 646, 714, 761, and 763.

[0155] The organic light-emitting compound according to the present invention contains an azine group, which is a strong electron acceptor in its molecular structure, and has excellent electron injection and transfer capabilities. Therefore, by improving the electron transfer capability to the light-emitting layer, the driving voltage of the device can be improved.

[0156] In addition, the organic light-emitting compound according to the present invention includes an aromatic hydrocarbon group that is not a simple aliphatic ring group and a structure in a condensed form, has excellent thermal stability, and has no crystallization temperature (Tc). Therefore, it is effective not only for the processability of the device but also for improving the lifetime.

[0157] In addition, the organic light-emitting compound according to the present invention has a structure in which a cyclohexylfluorene group substituted with a cyano group or a pyridine group and an azine moiety are linked at the ortho position via a linker. By this, the stability is improved, and at the same time, the dipole moment can be increased. Through this, the interaction with the cathode can be enhanced, and the electron generation in the device can be improved. Therefore, the driving voltage characteristics can be effectively improved.

[0158] In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0159] <Organic electroluminescent device>

[0160] The present invention provides an organic electroluminescent device including the novel organic light-emitting compound described above. The organic light-emitting compound according to the present invention may be included in any one or more of the organic layers disposed between the negative electrode and the positive electrode of the organic electroluminescent device.

[0161] In one embodiment, the organic electroluminescent device includes a positive electrode; a negative electrode; a light-emitting layer disposed between the negative electrode and the positive electrode; and an electron transport region disposed between the negative electrode and the light-emitting layer. The electron transport region includes the organic light-emitting compound according to the present invention.

[0162] [Positive electrode]

[0163] The organic electroluminescent device of the present invention includes a positive electrode. The positive electrode serves to inject holes into the organic layer. Here, the organic layer may mean one or more of the layers formed between the positive electrode and the negative electrode.

[0164] The cathode material can be any type and may be manufactured by conventional methods known in the art. Examples of cathode materials include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); metal-oxide composites such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, which may be used individually or in combination of two or more.

[0165] The positive electrode can be manufactured by any conventional method known in the art, without any particular limitations on its manufacturing method. For example, the positive electrode can be formed by coating a positive electrode material onto a substrate such as a silicon wafer, quartz, glass plate, metal plate, or plastic film.

[0166] [Negative electrode]

[0167] The organic electroluminescent element of the present invention includes a negative electrode. The negative electrode plays a role in injecting electrons into the organic material layer.

[0168] The negative electrode material forming the negative electrode can be manufactured by conventional methods known in the art, without any particular limitations on its type. Examples of negative electrode materials include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0169] [Luminous layer]

[0170] The organic electroluminescent element of the present invention includes a light-emitting layer disposed between the negative electrode and the positive electrode. The light-emitting layer is a layer in which holes and electrons meet and excitons are formed, and the color of the light emitted by the organic electroluminescent element can change depending on the material that makes up the light-emitting layer.

[0171] As the light-emitting material forming the light-emitting layer, a wide variety of commercially available materials can be used without any special restrictions, depending on the wavelength of the desired emitted light.

[0172] In one embodiment, the light-emitting material can be classified into blue, green, and red light-emitting materials depending on the emitted light. To prevent problems such as a decrease in color purity or a reduction in the efficiency of the device due to a light-reducing effect, a light-emitting layer can be formed by mixing a host material and a dopant material. The light-emitting efficiency of the light-emitting element can be improved by using a host material, which is the main material for forming the light-emitting layer, and a small amount of dopant with a smaller energy band gap compared to the host material.

[0173] [Electron transport area]

[0174] The organic electroluminescent element of the present invention includes an electron transport region disposed between the light-emitting layer and the negative electrode.

[0175] The electron transport region plays the role of moving electrons injected from the negative electrode to the light-emitting layer. Such an electron transport region may include one or more selected from the group consisting of electron injection layers and electron transport layers. In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include all of the above-mentioned electron transport layers and electron injection layers.

[0176] In the electron transport domain, the electron injection layer can use any electron injection material that readily receives electrons from the negative electrode and has high electron mobility without restriction. Non-restrictive examples of usable electron injection materials include positive polar compounds, anthracene derivatives, heteroaromatic compounds, and alkali metal complexes. Specifically, the electron injection material may include one or more selected from the group consisting of LiF, Li2O, BaO, NaCl, CsF; lanthanum group metals such as Yb; and metal halides such as RbCl and RbI.

[0177] The electron transport layer may include the organic light-emitting compound according to the present invention as described above. Furthermore, by using the novel organic light-emitting compound according to the present invention as the electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be achieved.

[0178] The electron transport layer can be formed by mixing the organic light-emitting compound according to the present invention with Liq (Lithium quinolate). Since the conduction band of Liq is 5.58 eV and the valance band is 3.153 eV, it has the effect of lowering the potential barrier.

[0179] Electron transport regions can be manufactured by conventional methods known in the art. These methods include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0180] [Electron transport auxiliary layer]

[0181] The organic electroluminescent element of the present invention may include an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region. The electron transport auxiliary layer can prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport region.

[0182] The electron transport auxiliary layer may include the organic light-emitting compound according to the present invention as described above. Furthermore, by using the novel organic light-emitting compound according to the present invention as the electron transport auxiliary layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be achieved.

[0183] As is known in the art, the electron transport auxiliary layer can be formed by, but is not limited to, vacuum evaporation, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, laser thermal transfer method (Laser Induced Thermal Imaging, LITI), etc.

[0184] [Hole transport region]

[0185] The organic electroluminescent device of the present invention can further include a hole transport region disposed between the anode and the light emitting layer. The hole transport region serves to move the holes injected from the anode to the light emitting layer.

[0186] The hole transport region can include one or more of a hole injection layer and a hole transport layer. At this time, considering the characteristics of the organic electroluminescent device, it is preferable to include all of the above-described hole injection layer and hole transport layer.

[0187] The materials forming the hole injection layer and the hole transport layer are not particularly limited as long as they have a low hole injection barrier and a high hole mobility, and the hole injection materials and hole transport materials used in the industry can be used without limitation. The materials forming the hole injection layer and the hole transport layer can be the same or different from each other.

[0188] Any hole-injection material known in this field can be used without restriction as the hole-injection material. Non-restrictive examples of usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4”-tris(3-methylphenylphenylamino)triphenylamine), TDATA (4,4',4”-Tris(N,N-diphenylamino)triphenylamine), 2TNATA (4,4',4”-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic Examples include ((Polyaniline) / Poly(4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonic acid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), which can be used individually or in combination of two or more.

[0189] Furthermore, any hole transporter known in this field can be used without restriction. Unrestricted examples of usable hole transporters include carbazole derivatives such as phenylcarbazole and polyvinylcarbazole; fluorene derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4”-tris(Ncarbazolyl)triphenylamine); and NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine) and TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]). These can be used individually or in combination of two or more.

[0190] Hole transport regions can be manufactured by conventional methods known in the art. For example, methods for manufacturing hole transport regions include, but are not limited to, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0191] [Hole transport auxiliary layer]

[0192] The organic electroluminescent device of the present invention may further include a hole transport auxiliary layer disposed between the hole transport region and the light-emitting layer. The hole transport auxiliary layer plays a role in transporting holes moving from the hole transport region to the light-emitting layer while also adjusting the thickness of the organic layer. Such a hole transport auxiliary layer prevents electrons from moving to the hole transport layer based on its high LUMO value and has a high triplet (T1) energy, thereby preventing excitons from the light-emitting layer from diffusing into the hole transport layer.

[0193] Such hole transport auxiliary layers may contain hole transport material and may be made of the same material as the hole transport region. Furthermore, the hole transport auxiliary layers of red, green, and blue organic light-emitting elements may be made of the same material as each other.

[0194] The hole transport auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives can be used. In addition, the hole transport auxiliary layer may selectively contain p-type dopants other than those mentioned above. Known p-type dopants used in the art may be used as the p-type dopant.

[0195] [Capping layer]

[0196] The organic electroluminescent element of the present invention may further include a capping layer disposed on the negative electrode. The capping layer protects the organic electroluminescent element while helping the light generated in the organic layer to be efficiently emitted to the outside.

[0197] The capping material forming the capping layer may include, but is not limited to, one or more substances selected from the group consisting of, for example, tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), and 1,1'-bis(di-4-tolylaminophenyl)cyclohexane (TAPC).

[0198] The capping layer may be a single layer, but it may also include two or more layers with different refractive indices, allowing the refractive index to be gradually changed as the material passes through these two or more layers.

[0199] The capping layer can be manufactured by conventional methods known in the art. For example, various methods such as vacuum deposition, spin coating, casting, or the LB (Langmuir-Blodgett) method can be used to manufacture the capping layer.

[0200] The present invention provides applications for the above-mentioned organic light-emitting compounds in organic electroluminescent devices. Through this, it provides organic electroluminescent devices with significantly improved light-emitting performance, driving voltage, lifespan, and efficiency.

[0201] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0202] In one embodiment, the organic light-emitting compound can be used as an electron transport material in the organic electroluminescent device.

[0203] In one embodiment, the organic light-emitting compound can be used as a material for the electron transport layer and / or electron transport auxiliary layer in the organic electroluminescent device.

[0204] The present invention will be described in detail below through examples, but the following examples are merely illustrative and the present invention is not limited to the following examples. [Examples]

[0205] [Example of preparation]

[0206] [Preparation Example 1]: Synthesis of Compound S01

[0207] [ka]

[0208] 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile (25.0 g, 64.9 mmol), 1-bromo-2-chlorobenzene (12.4 g, 64.9 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (26.9 g, 194.6 mmol) were placed in a mixed solvent consisting of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S01 (2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (20.4 g, 55.2 mmol, yield 85%).

[0209] Mass:[(M+H)] + ]:371

[0210] [Preparation Example 2]: Synthesis of Compound S02

[0211] [ka]

[0212] 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile (25.0 g, 64.9 mmol), 1-bromo-2-chlorobenzene (12.4 g, 64.9 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (26.9 g, 194.6 mmol) were placed in a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S02 (2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (20.6 g, 55.8 mmol, yield 86%).

[0213] Mass:[(M+H)] + ]:371

[0214] [Preparation Example 3]: Synthesis of Compound S03

[0215] [ka]

[0216] 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile (25.0 g, 64.9 mmol), 1-bromo-2-chlorobenzene (12.4 g, 64.9 mmol), Pd(PPh3)4 (2.2 g, 1.9 mmol), and K2CO3 (26.9 g, 194.6 mmol) were placed in a mixed solvent consisting of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S03 (5'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (20.9 g, 56.4 mmol, yield 87%).

[0217] Mass:[(M+H)] + ]:371

[0218] [Preparation Example 4]: Synthesis of Compound S04

[0219] [ka]

[0220] 3-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine (25.0 g, 57.2 mmol), 1-bromo-2-chlorobenzene (10.9 g, 57.2 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), and K2CO3 (23.7 g, 171.5 mmol) were placed in a mixed solvent consisting of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S04 (3-(2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine) (21.0 g, 49.7 mmol, yield 87%).

[0221] Mass:[(M+H)] + ]:423

[0222] [Preparation Example 5]: Synthesis of Compound S05

[0223] [ka]

[0224] 3-(3’-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9’-fluorene]-7’-yl)pyridine (25.0 g, 57.2 mmol), 1-bromo-2-chlorobenzene (10.9 g, 57.2 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol) and K2CO3 (23.7 g, 171.5 mmol) were placed in a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol and 37.5 ml of water, and reacted with heating under reflux and stirring for 2 hours. After completion of the reaction, extraction was carried out with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfate and purified by column chromatography to obtain compound S05 (3-(3’-(2-chlorophenyl)spiro[cyclohexane-1,9’-fluorene]-7’-yl)pyridine) (20.7 g, 49.2 mmol, yield 86%).

[0225] Mass:[(M+H) + :423

[0226] [Preparation Example 6]: Synthesis of Compound S06

[0227]

Chemical Structure

[0228] 3-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine (25.0 g, 57.2 mmol), 1-bromo-2-chlorobenzene (10.9 g, 57.2 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), and K2CO3 (23.7 g, 171.5 mmol) were placed in a mixed solvent consisting of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S06 (3-(3'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine) (20.5 g, 48.6 mmol, yield 85%).

[0229] Mass:[(M+H)] + ]:423

[0230] [Preparation Example 7]: Synthesis of Compound S07

[0231] [ka]

[0232] 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzonitrile (25.0 g, 54.2 mmol), 1-bromo-2-chlorobenzene (10.4 g, 54.2 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.5 g, 162.5 mmol) were placed in a mixed solvent consisting of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted over 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound S07 (4-(2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzonitrile) (20.5 g, 46.1 mmol, yield 85%).

[0233] Mass:[(M+H)] + ]:447

[0234] [Preparation Example 8]: Synthesis of Compound A01

[0235] [ka]

[0236] Compound S01 (20.0 g, 54.1 mmol), bis(pinacolate)diborone (17.8 g, 70.3 mmol), Pd(dppf)Cl2 (1.2 g, 1.6 mmol), X-Phos (1.5 g, 3.2 mmol), and KOAc (10.6 g, 108.1 mmol), synthesized by the method of Preparation Example 1, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A01 (7'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (20.5 g, 44.3 mmol, yield 82%) was obtained by column chromatography.

[0237] Mass:[(M+H)] + ]:462

[0238] [Preparation Example 9]: Synthesis of Compound A02

[0239] [ka]

[0240] Compound S02 (20.0 g, 54.1 mmol), bis(pinacolate)diborone (17.8 g, 70.3 mmol), Pd(dppf)Cl2 (1.2 g, 1.6 mmol), X-Phos (1.5 g, 3.2 mmol), and KOAc (10.6 g, 108.1 mmol), synthesized by the method of Preparation Example 2, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A02 (6'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (20.7 g, 44.9 mmol, yield 83%) was obtained by column chromatography.

[0241] Mass:[(M+H)]+ ]:462

[0242] [Preparation Example 10]: Synthesis of Compound A03

[0243] [ka]

[0244] Compound S03 (20.0 g, 54.1 mmol), bis(pinacolate)diborone (17.8 g, 70.3 mmol), Pd(dppf)Cl2 (1.2 g, 1.6 mmol), X-Phos (1.5 g, 3.2 mmol), and KOAc (10.6 g, 108.1 mmol), synthesized by the method of Preparation Example 3, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A03 (5'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (20.5 g, 44.3 mmol, yield 82%) was obtained by column chromatography.

[0245] Mass:[(M+H)] + ]:462

[0246] [Preparation Example 11]: Synthesis of Compound A04

[0247] [ka]

[0248] Compound S04 (20.0 g, 47.4 mmol), bis(pinacolate)diborone (15.6 g, 61.6 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (0.3 g, 0.7 mmol), and KOAc (2.1 g, 21.9 mmol), synthesized by the method of Preparation Example 4, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A04 (3-(2'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine) (18.4 g, 39.8 mmol, yield 84%).

[0249] Mass:[(M+H)] + ]:462

[0250] [Preparation Example 12]: Synthesis of Compound A05

[0251] [ka]

[0252] Compound S05 (20.0 g, 47.4 mmol), bis(pinacolate)diborone (15.6 g, 61.6 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (0.3 g, 0.7 mmol), and KOAc (2.1 g, 21.9 mmol), synthesized by the method of Preparation Example 5, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A05 (3-(3'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine) (17.9 g, 38.9 mmol, yield 82%).

[0253] Mass:[(M+H)] + ]:462

[0254] [Preparation Example 13]: Synthesis of Compound A06

[0255] [ka]

[0256] Compound S06 (20.0 g, 47.4 mmol), bis(pinacolate)diborone (15.6 g, 61.6 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (0.3 g, 0.7 mmol), and KOAc (2.1 g, 21.9 mmol), synthesized by the method of Preparation Example 6, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A06 (3-(4'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)pyridine) (18.2 g, 39.3 mmol, yield 83%).

[0257] Mass:[(M+H)] + ]:462

[0258] [Preparation Example 14]: Synthesis of Compound A07

[0259] [ka]

[0260] S07 (20.0 g, 44.8 mmol), bis(pinacolate)diborone (14.8 g, 58.3 mmol), Pd(dppf)Cl2 (1.0 g, 1.3 mmol), X-Phos (0.3 g, 0.7 mmol), and KOAc (2.1 g, 21.9 mmol), synthesized by the method of Preparation Example 7, were added to 200 ml of 1,4-dioxane and reacted under heating, reflux, and stirring for 6 hours. After the reaction was terminated, the solvent was removed by filtration and concentration, and the compound A07 (4-(2'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzonitrile) (20.0 g, 37.2 mmol, yield 83%).

[0261] Mass:[(M+H)] + ]:539

[0262] [Preparation Example 15]: Synthesis of Compound B01

[0263] [ka]

[0264] 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (24.2 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B01 (2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine) (15.5 g, 45.0 mmol, yield 84%).

[0265] Mass:[(M+H)] + ]:345

[0266] [Preparation Example 16]: Synthesis of Compound B02

[0267] [ka]

[0268] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (24.2 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B02 (2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine) (15.3 g, 44.4 mmol, yield 83%).

[0269] Mass:[(M+H)] + ]:345

[0270] [Preparation Example 17]: Synthesis of Compound B03

[0271] [ka]

[0272] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (24.2 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B03 (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine) (15.1 g, 43.9 mmol, yield 82%).

[0273] Mass:[(M+H)] + ]:345

[0274] [Preparation Example 18]: Synthesis of Compound B04

[0275] [ka]

[0276] 4,4,5,5-tetramethyl-2-(naphthalene-1-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (26.7 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B04 (2-chloro-4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine) (15.9 g, 50.2 mmol, yield 85%).

[0277] Mass:[(M+H)] + ]:319

[0278] [Preparation Example 19]: Synthesis of Compound B05

[0279] [ka]

[0280] 4,4,5,5-tetramethyl-2-(naphthalene-2-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (26.7 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B05 (2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine) (15.8 g, 49.6 mmol, yield 84%).

[0281] Mass:[(M+H)] + ]:319

[0282] [Preparation Example 20]: Synthesis of Compound B06

[0283] [ka]

[0284] 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B06 (4-([1,1'-biphenyl]-2-yl)-2-chloro-6-phenylpyrimidine) (15.2 g, 44.4 mmol, yield 83%).

[0285] Mass:[(M+H)] + ]:344

[0286] [Preparation Example 21]: Synthesis of Compound B07

[0287] [ka]

[0288] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B07 (4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine) (15.4 g, 45.0 mmol, yield 84%).

[0289] Mass:[(M+H)] + ]:344

[0290] [Preparation Example 22]: Synthesis of Compound B08

[0291] [ka]

[0292] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 2,4-dichloro-6-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B08 (4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine) (15.2 g, 44.4 mmol, yield 83%).

[0293] Mass:[(M+H)] + ]:344

[0294] [Preparation Example 23]: Synthesis of Compound B09

[0295] [ka]

[0296] 4,4,5,5-tetramethyl-2-(naphthalene-1-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 2,4-dichloro-6-phenylpyrimidine (26.6 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B09 (2-chloro-4-(naphthalene-1-yl)-6-phenylpyrimidine) (15.7 g, 49.6 mmol, yield 84%).

[0297] Mass:[(M+H)] + ]:318

[0298] [Preparation Example 24]: Synthesis of Compound B10

[0299] [ka]

[0300] 4,4,5,5-tetramethyl-2-(naphthalene-2-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 2,4-dichloro-6-phenylpyrimidine (26.6 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B10 (2-chloro-4-(naphthalene-2-yl)-6-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0301] Mass:[(M+H)] + ]:318

[0302] [Preparation Example 25]: Synthesis of Compound B11

[0303] [ka]

[0304] 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 4,6-dichloro-2-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted over 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B11 (4-([1,1'-biphenyl]-2-yl)-2-chloro-6-phenylpyrimidine) (15.6 g, 45.5 mmol, yield 85%).

[0305] Mass:[(M+H)] + ]:344

[0306] [Preparation Example 26]: Synthesis of Compound B12

[0307] [ka]

[0308] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 4,6-dichloro-2-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B12 (4-([1,1'-biphenyl]-3-yl)-2-chloro-6-phenylpyrimidine) (15.6 g, 45.5 mmol, yield 85%).

[0309] Mass:[(M+H)] + ]:344

[0310] [Preparation Example 27]: Synthesis of Compound B13

[0311] [ka]

[0312] 2-([1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 53.5 mmol), 4,6-dichloro-2-phenylpyrimidine (24.1 g, 107.1 mmol), Pd(PPh3)4 (1.9 g, 1.6 mmol), and K2CO3 (22.2 g, 160.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B13 (4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine) (15.4 g, 45.0 mmol, yield 84%).

[0313] Mass:[(M+H)] + ]:344

[0314] [Preparation Example 28]: Synthesis of Compound B14

[0315] [ka]

[0316] 4,4,5,5-tetramethyl-2-(naphthalene-1-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 4,6-dichloro-2-phenylpyrimidine (26.6 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B14 (4-chloro-6-(naphthalene-1-yl)-2-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0317] Mass:[(M+H)] + ]:318

[0318] [Preparation Example 29]: Synthesis of Compound B15

[0319] [ka]

[0320] 4,4,5,5-tetramethyl-2-(naphthalene-2-yl)-1,3,2-dioxaborolane (15.0 g, 59.0 mmol), 4,6-dichloro-2-phenylpyrimidine (26.6 g, 118.0 mmol), Pd(PPh3)4 (2.0 g, 1.8 mmol), and K2CO3 (24.5 g, 177.1 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B15 (4-chloro-6-(naphthalene-2-yl)-2-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0321] Mass:[(M+H)] + ]:318

[0322] [Preparation Example 30]: Synthesis of Compound B16

[0323] [ka]

[0324] 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (15.0 g, 73.5 mmol), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloropyrimidine (44.3 g, 147.0 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol), and K2CO3 (30.5 g, 220.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B16 (2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenylpyrimidine) (21.4 g, 62.5 mmol, yield 85%).

[0325] Mass:[(M+H)] + ]:344

[0326] [Preparation Example 31]: Synthesis of Compound B17

[0327] [ka]

[0328] 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (15.0 g, 73.5 mmol), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloropyrimidine (44.3 g, 147.0 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol), and K2CO3 (30.5 g, 220.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B17 (2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenylpyrimidine) (21.2 g, 61.7 mmol, yield 84%).

[0329] Mass:[(M+H)] + ]:344

[0330] [Preparation Example 32]: Synthesis of Compound B18

[0331] [ka]

[0332] 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (15.0 g, 73.5 mmol), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloropyrimidine (44.3 g, 147.0 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol), and K2CO3 (30.5 g, 220.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B18 (2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine) (20.9 g, 61.0 mmol, yield 83%).

[0333] Mass:[(M+H)] + ]:344

[0334] [Preparation Example 33]: Synthesis of Compound B19

[0335] [ka]

[0336] 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (15.0 g, 73.5 mmol), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloropyrimidine (44.3 g, 147.0 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol), and K2CO3 (30.5 g, 220.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B19 (4-chloro-2-(naphthalene-1-yl)-6-phenylpyrimidine) (19.1 g, 60.3 mmol, yield 82%).

[0337] Mass:[(M+H)] + ]:318

[0338] [Preparation Example 34]: Synthesis of Compound B20

[0339] [ka]

[0340] 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (15.0 g, 73.5 mmol), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloropyrimidine (44.3 g, 147.0 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol), and K2CO3 (30.5 g, 220.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B20 (4-chloro-2-(naphthalene-2-yl)-6-phenylpyrimidine) (19.3 g, 61.0 mmol, yield 83%).

[0341] Mass:[(M+H)] + ]:318

[0342] [Preparation Example 35]: Synthesis of Compound B21

[0343] [ka]

[0344] 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 51.0 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (23.1 g, 102.0 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.1 g, 153.0 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B21 (2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine) (15.3 g, 42.8 mmol, yield 84%).

[0345] Mass:[(M+H)] + ]:339

[0346] [Preparation Example 36]: Synthesis of Compound B22

[0347] [ka]

[0348] 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 48.4 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (21.9 g, 96.7 mmol), Pd(PPh3)4 (1.7 g, 1.5 mmol), and K2CO3 (20.0 g, 145.1 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B22 (2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine) (15.2 g, 40.6 mmol, yield 84%).

[0349] Mass:[(M+H)] + ]:375

[0350] [Preparation Example 37]: Synthesis of Compound B23

[0351] [ka]

[0352] 2-(9,9-dimethyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 46.8 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (21.2 g, 93.7 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (19.4 g, 140.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B23 (2-chloro-4-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine) (15.1 g, 39.3 mmol, yield 84%).

[0353] Mass:[(M+H)] + ]:385

[0354] [Preparation Example 38]: Synthesis of Compound B24

[0355] [ka]

[0356] 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (15.0 g, 40.6 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (18.4 g, 81.2 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.8 g, 121.9 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B24 (3-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9-phenyl-9H-carbazole) (14.8 g, 34.1 mmol, yield 84%).

[0357] Mass:[(M+H)] + ]:434

[0358] [Preparation Example 39]: Synthesis of Compound B25

[0359] [ka]

[0360] 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (15.0 g, 40.6 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (18.4 g, 81.2 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (16.8 g, 121.9 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B25 (9-(3-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)phenyl)-9H-carbazole) (14.8 g, 34.1 mmol, yield 84%).

[0361] Mass:[(M+H)] + ]:434

[0362] [Preparation Example 40]: Synthesis of Compound B26

[0363] [ka]

[0364] 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 51.0 mmol), 2,4-dichloro-6-phenylpyrimidine (23.0 g, 102.0 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.1 g, 153.0 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B26 (2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenylpyrimidine) (15.8 g, 42.3 mmol, yield 83%).

[0365] Mass:[(M+H)] + ]:374

[0366] [Preparation Example 41]: Synthesis of Compound B27

[0367] [ka]

[0368] 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.0 g, 48.4 mmol), 4,6-dichloro-2-phenylpyrimidine (21.8 g, 96.7 mmol), Pd(PPh3)4 (1.7 g, 1.5 mmol), and K2CO3 (20.0 g, 145.1 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted over 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B27 (4-chloro-6-(dibenzo[b,d]thiophen-2-yl)-2-phenylpyrimidine) (15.1 g, 40.6 mmol, yield 84%).

[0369] Mass:[(M+H)] + ]:374

[0370] [Preparation Example 42]: Synthesis of Compound B28

[0371] [ka]

[0372] 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (25.0 g, 57.4 mmol), 1-bromo-2-chlorobenzene (11.0 g, 57.4 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), and K2CO3 (23.8 g, 172.3 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B28 (2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine) (20.5 g, 48.8 mmol, yield 85%).

[0373] Mass:[(M+H)] + ]:421

[0374] [Preparation Example 43]: Synthesis of Compound B29

[0375] [ka]

[0376] 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (25.0 g, 57.6 mmol), 3-bromo-1-chlorodibenzo[b,d]thiophene (17.1 g, 57.6 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), and K2CO3 (23.9 g, 172.7 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B29 (4-(2-(1-chlorodibenzo[b,d]thiophen-3-yl)phenyl)-2,6-diphenylpyrimidine) (20.6 g, 48.9 mmol, yield 85%).

[0377] Mass:[(M+H)] + ]:423

[0378] [Preparation Example 44]: Synthesis of Compound B30

[0379] [ka]

[0380] 2,3-diphenyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine (25.0 g, 57.6 mmol), 3-bromo-1-chlorodibenzo[b,d]thiophene (17.1 g, 57.6 mmol), Pd(PPh3)4 (2.0 g, 1.7 mmol), and K2CO3 (23.9 g, 172.7 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound B30 (5-(2-(1-chlorodibenzo[b,d]thiophen-3-yl)phenyl)-2,3-diphenylpyrazine) (25.7 g, 48.9 mmol, yield 85%).

[0381] Mass:[(M+H)] + ]:526

[0382] [Example of combination]

[0383] [Synthesis Example 1]: Synthesis of Compound 006

[0384] [ka]

[0385] Compound A01 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 8, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 006 (7'-(2-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.3 g, 23.4 mmol, yield 72%).

[0386] Mass:[(M+H)] + ]:568

[0387] [Synthesis Example 2]: Synthesis of Compound 010

[0388] [ka]

[0389] Compound A02 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 9, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 010 (6'-(2-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.8 g, 24.4 mmol, yield 75%).

[0390] Mass:[(M+H)] + ]:568

[0391] [Synthesis Example 3]: Synthesis of Compound 014

[0392] [ka]

[0393] Compound A03 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 10, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 014 (5'-(2-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0394] Mass:[(M+H)] + ]:568

[0395] [Synthesis Example 4]: Synthesis of Compound 022

[0396] [ka]

[0397] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B01 (11.2 g, 32.5 mmol) synthesized by the method of Preparation Example 15, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 022 (2'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.7 g, 23.7 mmol, yield 75%).

[0398] Mass:[(M+H)] + ]:644

[0399] [Synthesis Example 5]: Synthesis of Compound 026

[0400] [ka]

[0401] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B01 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 15 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 026 (6'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.5 g, 24.7 mmol, yield 74%).

[0402] Mass:[(M+H)] + ]:644

[0403] [Synthesis Example 6]: Synthesis of Compound 030

[0404] [ka]

[0405] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B01 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 15 were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 030 (5'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0406] Mass:[(M+H)] + ]:644

[0407] [Synthesis Example 7]: Synthesis of Compound 038

[0408] [ka]

[0409] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B02 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 16 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 038 (2'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0410] Mass:[(M+H)] + ]:644

[0411] [Synthesis Example 8]: Synthesis of Compound 042

[0412] [ka]

[0413] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B02 (11.2 g, 32.5 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 042 (6'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.7 g, 24.1 mmol, yield 74%).

[0414] Mass:[(M+H)] + ]:644

[0415] [Synthesis Example 9]: Synthesis of Compound 046

[0416] [ka]

[0417] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B02 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 16 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 046 (5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0418] Mass:[(M+H)] + ]:644

[0419] [Synthesis Example 10]: Synthesis of Compound 054

[0420] [ka]

[0421] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B03 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 17 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 054 (2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0422] Mass:[(M+H)] + ]:644

[0423] [Synthesis Example 11]: Synthesis of Compound 058

[0424] [ka]

[0425] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B03 (11.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 17 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 058 (6'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.7 g, 23.1 mmol, yield 74%).

[0426] Mass:[(M+H)] + ]:644

[0427] [Synthesis Example 12]: Synthesis of Compound 062

[0428] [ka]

[0429] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B03 (11.2 g, 32.5 mmol) synthesized by the method of Preparation Example 17, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 062 (5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (17.1 g, 24.7 mmol, yield 76%).

[0430] Mass:[(M+H)] + ]:644

[0431] [Synthesis Example 13]: Synthesis of Compound 070

[0432] [ka]

[0433] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B02 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 16 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 070 (7'-(2-(4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.9 g, 24.4 mmol, yield 75%).

[0434] Mass:[(M+H)] + ]:618

[0435] [Synthesis Example 14]: Synthesis of Compound 074

[0436] [ka]

[0437] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B04 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 18 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 074 (6'-(2-(4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (17.3 g, 25.0 mmol, yield 77%).

[0438] Mass:[(M+H)] + ]:618

[0439] [Synthesis Example 15]: Synthesis of Compound 078

[0440] [ka]

[0441] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B04 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 18 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 078 (5'-(2-(4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.7 g, 24.1 mmol, yield 74%).

[0442] Mass:[(M+H)] + ]:618

[0443] [Synthesis Example 16]: Synthesis of Compound 086

[0444] [ka]

[0445] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B05 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 19 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 086(7'-(2-(4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0446] Mass:[(M+H)] + ]:618

[0447] [Synthesis Example 17]: Synthesis of Compound 090

[0448] [ka]

[0449] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B05 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 19 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 090 (6'-(2-(4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0450] Mass:[(M+H)] + ]:618

[0451] [Synthesis Example 18]: Synthesis of Compound 094

[0452] [ka]

[0453] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B05 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 19 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 094 (5'-(2-(4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0454] Mass:[(M+H)] + ]:618

[0455] [Synthesis Example 19]: Synthesis of Compound 102

[0456] [ka]

[0457] Compound A01 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenylpyrimidine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 8, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 102 (7'-(2-(4,6-diphenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0458] Mass:[(M+H)] + ]:567

[0459] [Synthesis Example 20]: Synthesis of Compound 106

[0460] [ka]

[0461] Compound A02 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenylpyrimidine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 9, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 106 (6'-(2-(4,6-diphenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0462] Mass:[(M+H)] + ]:567

[0463] [Synthesis Example 21]: Synthesis of Compound 110

[0464] [ka]

[0465] Compound A03 (15.0 g, 32.5 mmol), 2-chloro-4,6-diphenylpyrimidine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 10, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 110 (5'-(2-(4,6-diphenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.7 g, 24.1 mmol, yield 74%).

[0466] Mass:[(M+H)] + ]:567

[0467] [Synthesis Example 22]: Synthesis of Compound 118

[0468] [ka]

[0469] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B06 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 20, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 118 (2'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0470] Mass:[(M+H)] + ]:643

[0471] [Synthesis Example 23]: Synthesis of Compound 122

[0472] [ka]

[0473] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B06 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 20, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 122 (6'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.9 g, 24.4 mmol, yield 75%).

[0474] Mass:[(M+H)] + ]:643

[0475] [Synthesis Example 24]: Synthesis of Compound 126

[0476] [ka]

[0477] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B06 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 20, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 126 (5'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0478] Mass:[(M+H)] + ]:643

[0479] [Synthesis Example 25]: Synthesis of Compound 134

[0480] [ka]

[0481] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B07 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 21, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 134 (2'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0482] Mass:[(M+H)] + ]:643

[0483] [Synthesis Example 26]: Synthesis of Compound 138

[0484] [ka]

[0485] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B07 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 21, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 138 (6'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0486] Mass:[(M+H)] + ]:643

[0487] [Synthesis Example 27]: Synthesis of Compound 142

[0488] [ka]

[0489] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B07 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 21, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 142 (5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0490] Mass:[(M+H)] + ]:643

[0491] [Synthesis Example 28]: Synthesis of Compound 150

[0492] [ka]

[0493] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B08 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 22, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 150 (2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (16.2 g, 23.4 mmol, yield 72%).

[0494] Mass:[(M+H)] + ]:643

[0495] [Synthesis Example 29]: Synthesis of Compound 154

[0496] [ka]

[0497] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B08 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 22, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 154 (6'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.9 g, 24.4 mmol, yield 75%).

[0498] Mass:[(M+H)] + ]:643

[0499] [Synthesis Example 30]: Synthesis of Compound 158

[0500] [ka]

[0501] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B08 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 22, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 158 (5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0502] Mass:[(M+H)] + ]:643

[0503] [Synthesis Example 31]: Synthesis of Compound 166

[0504] [ka]

[0505] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B09 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 23, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 166 (7'-(2-(4-(naphthalene-1-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0506] Mass:[(M+H)] + ]:617

[0507] [Synthesis Example 32]: Synthesis of Compound 170

[0508] [ka]

[0509] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B09 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 23, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 170 (6'-(2-(4-(naphthalene-1-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 24.4 mmol, yield 75%).

[0510] Mass:[(M+H)] + ]:617

[0511] [Synthesis Example 33]: Synthesis of Compound 174

[0512] [ka]

[0513] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B09 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 23, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 174 (5'-(2-(4-(naphthalene-1-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0514] Mass:[(M+H)] + ]:617

[0515] [Synthesis Example 34]: Synthesis of Compound 182

[0516] [ka]

[0517] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B10 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 24, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 182 (7'-(2-(4-(naphthalene-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 24.4 mmol, yield 75%).

[0518] Mass:[(M+H)] + ]:617

[0519] [Synthesis Example 35]: Synthesis of Compound 186

[0520] [ka]

[0521] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B10 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 24, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 186 (6'-(2-(4-(naphthalene-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.8 g, 24.1 mmol, yield 74%).

[0522] Mass:[(M+H)] + ]:617

[0523] [Synthesis Example 36]: Synthesis of Compound 190

[0524] [ka]

[0525] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B10 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 24, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 190 (5'-(2-(4-(naphthalene-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0526] Mass:[(M+H)] + ]:617

[0527] [Synthesis Example 37]: Synthesis of Compound 198

[0528] [ka]

[0529] Compound A01 (15.0 g, 32.5 mmol), 4-chloro-2,6-diphenylpyrimidine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 8, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 198 (7'-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0530] Mass:[(M+H)] + ]:567

[0531] [Synthesis Example 38]: Synthesis of Compound 202

[0532] [ka]

[0533] Compound A02 (15.0 g, 32.5 mmol), 4-chloro-2,6-diphenylpyrimidine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 9, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 202 (6'-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.6 g, 24.1 mmol, yield 74%).

[0534] Mass:[(M+H)] + ]:567

[0535] [Synthesis Example 39]: Synthesis of Compound 206

[0536] [ka]

[0537] Compound A03 (15.0 g, 32.5 mmol), 4-chloro-2,6-diphenylpyrimidine (8.7 g, 32.5 mmol) (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 102, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 206 (5'-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0538] Mass:[(M+H)] + ]:567

[0539] [Synthesis Example 40]: Synthesis of Compound 214

[0540] [ka]

[0541] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B11 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 25, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 214 (2'-(2-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0542] Mass:[(M+H)] + ]:643

[0543] [Synthesis Example 41]: Synthesis of Compound 218

[0544] [ka]

[0545] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B11 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 25 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 218 (6'-(2-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.4 g, 24.1 mmol, yield 74%).

[0546] Mass:[(M+H)] + ]:643

[0547] [Synthesis Example 42]: Synthesis of Compound 222

[0548] [ka]

[0549] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B11 (11.1 g, 32.5 mmol) (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 25, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol and 22.5 ml of water, and reacted with heating under reflux and stirring for 2 hours. After completion of the reaction, extraction was carried out with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfate and purified by column chromatography to obtain compound 222 (5'-(2-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.9 g, 24.7 mmol, yield 76%).

[0550] Mass:[(M+H) + :643

[0551] [Synthesis Example 43]: Synthesis of Compound 230

[0552]

Chemical Structure

[0553] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B12 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 262 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 230 (2'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.6 g, 24.4 mmol, yield 75%).

[0554] Mass:[(M+H)] + ]:643

[0555] [Synthesis Example 44]: Synthesis of Compound 234

[0556] [ka]

[0557] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B12 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 26 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 234 (6'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.1 g, 25.0 mmol, yield 77%).

[0558] Mass:[(M+H)] + ]:643

[0559] [Synthesis Example 45]: Synthesis of Compound 238

[0560] [ka]

[0561] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B12 (11.1 g, 32.5 mmol) (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 26 were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 238 (5'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.4 g, 24.1 mmol, yield 74%).

[0562] Mass:[(M+H)] + ]:643

[0563] [Synthesis Example 46]: Synthesis of Compound 246

[0564] [ka]

[0565] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B13 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 27, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 246 (2'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0566] Mass:[(M+H)] + ]:643

[0567] [Synthesis Example 47]: Synthesis of Compound 250

[0568] [ka]

[0569] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B11 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 25 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 250 (6'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0570] Mass:[(M+H)] + ]:643

[0571] [Synthesis Example 48]: Synthesis of Compound 254

[0572] [ka]

[0573] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B13 (11.1 g, 32.5 mmol) (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 27 were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 254 (5'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0574] Mass:[(M+H)] + ]:643

[0575] [Synthesis Example 49]: Synthesis of Compound 262

[0576] [ka]

[0577] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B14 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 28, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol and 22.5 ml of water, and reacted with heating under reflux and stirring for 2 hours. After completion of the reaction, extraction was carried out with methylene chloride. The extracted organic layer was concentrated after removing moisture with magnesium sulfate, and purified by column chromatography to obtain compound 262 (7'-(2-(6-(naphthalen-1-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0578] Mass:[(M+H) + :617

[0579] [Synthesis Example 50]: Synthesis of Compound 266

[0580]

Chemical Structure

[0581] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B14 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 28 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 266 (6'-(2-(6-(naphthalene-1-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 24.4 mmol, yield 75%).

[0582] Mass:[(M+H)] + ]:617

[0583] [Synthesis Example 51]: Synthesis of Compound 270

[0584] [ka]

[0585] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B14 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 28 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 270 (5'-(2-(6-(naphthalene-1-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.8 g, 24.1 mmol, yield 74%).

[0586] Mass:[(M+H)] + ]:617

[0587] [Synthesis Example 52]: Synthesis of Compound 278

[0588] [ka]

[0589] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B15 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 29, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 278 (7'-(2-(6-(naphthalene-2-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0590] Mass:[(M+H)] + ]:617

[0591] [Synthesis Example 53]: Synthesis of Compound 282

[0592] [ka]

[0593] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B15 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 29 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 282 (6'-(2-(6-(naphthalene-2-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 24.4 mmol, yield 75%).

[0594] Mass:[(M+H)] + ]:617

[0595] [Synthesis Example 54]: Synthesis of Compound 286

[0596] [ka]

[0597] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B15 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 29, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 286 (5'-(2-(6-(naphthalene-1-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0598] Mass:[(M+H)] + ]:617

[0599] [Synthesis Example 55]: Synthesis of Compound 294

[0600] [ka]

[0601] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B16 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 30, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 294 (2'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0602] Mass:[(M+H)] + ]:643

[0603] [Synthesis Example 56]: Synthesis of Compound 298

[0604] [ka]

[0605] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B16 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 30 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 298 (6'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.6 g, 24.4 mmol, yield 75%).

[0606] Mass:[(M+H)] + ]:643

[0607] [Synthesis Example 57]: Synthesis of Compound 302

[0608] [ka]

[0609] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B16 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 30 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 302 (5'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.2 g, 23.7 mmol, yield 73%).

[0610] Mass:[(M+H)] + ]:643

[0611] [Synthesis Example 58]: Synthesis of Compound 310

[0612] [ka]

[0613] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B17 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 31 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 310 (2'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0614] Mass:[(M+H)] + ]:643

[0615] [Synthesis Example 59]: Synthesis of Compound 314

[0616] [ka]

[0617] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B17 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 31 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 314 (6'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.6 g, 24.4 mmol, yield 75%).

[0618] Mass:[(M+H)] + ]:643

[0619] [Synthesis Example 60]: Synthesis of Compound 318

[0620] [ka]

[0621] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B17 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 31 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 318 (5'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.2 g, 23.7 mmol, yield 73%).

[0622] Mass:[(M+H)] + ]:643

[0623] [Synthesis Example 61]: Synthesis of Compound 326

[0624] [ka]

[0625] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B18 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 32 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 326 (2'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (15.6 g, 24.4 mmol, yield 75%).

[0626] Mass:[(M+H)] + ]:643

[0627] [Synthesis Example 62]: Synthesis of Compound 330

[0628] [ka]

[0629] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B18 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 32 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 330 (6'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.4 g, 24.1 mmol, yield 74%).

[0630] Mass:[(M+H)] + ]:643

[0631] [Synthesis Example 63]: Synthesis of Compound 334

[0632] [ka]

[0633] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B18 (11.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 32 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 334 (5'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 23.4 mmol, yield 72%).

[0634] Mass:[(M+H)] + ]:643

[0635] [Synthesis Example 64]: Synthesis of Compound 342

[0636] [ka]

[0637] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B19 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 33 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 342 (7'-(2-(2-(naphthalene-1-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0638] Mass:[(M+H)] + ]:617

[0639] [Synthesis Example 65]: Synthesis of Compound 346

[0640] [ka]

[0641] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B19 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 33 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 346 (6'-(2-(2-(naphthalene-1-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0642] Mass:[(M+H)] + ]:617

[0643] [Synthesis Example 66]: Synthesis of Compound 350

[0644] [ka]

[0645] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B19 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 33 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 350 (5'-(2-(2-(naphthalene-1-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0646] Mass:[(M+H)] + ]:617

[0647] [Synthesis Example 67]: Synthesis of Compound 358

[0648] [ka]

[0649] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B20 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 34 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 358 (7'-(2-(2-(naphthalene-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0650] Mass:[(M+H)] + ]:617

[0651] [Synthesis Example 68]: Synthesis of Compound 362

[0652] [ka]

[0653] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B20 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 34 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 362 (6'-(2-(2-(naphthalene-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.8 g, 24.1 mmol, yield 74%).

[0654] Mass:[(M+H)] + ]:617

[0655] [Synthesis Example 69]: Synthesis of Compound 366

[0656] [ka]

[0657] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B20 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 34 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 366 (5'-(2-(2-(naphthalene-2-yl)-6-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.2 g, 24.7 mmol, yield 76%).

[0658] Mass:[(M+H)] + ]:617

[0659] [Synthesis Example 70]: Synthesis of Compound 374

[0660] [ka]

[0661] Compound A01 (15.0 g, 32.5 mmol), 2-chloro-3,5-diphenylpyrazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 8, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 374 (7'-(2-(3,5-diphenylpyrazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0662] Mass:[(M+H)] + ]:567

[0663] [Synthesis Example 71]: Synthesis of Compound 378

[0664] [ka]

[0665] Compound A02 (15.0 g, 32.5 mmol), 2-chloro-3,5-diphenylpyrazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 9, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 378 (6'-(2-(3,5-diphenylpyrazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.2 g, 23.4 mmol, yield 72%).

[0666] Mass:[(M+H)] + ]:567

[0667] [Synthesis Example 72]: Synthesis of Compound 382

[0668] [ka]

[0669] Compound A03 (15.0 g, 32.5 mmol), 2-chloro-3,5-diphenylpyrazine (8.7 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol), synthesized by the method of Preparation Example 10, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 382 (5'-(2-(3,5-diphenylpyrazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0670] Mass:[(M+H)] + ]:567

[0671] [Synthesis Example 73]: Synthesis of Compound 390

[0672] [ka]

[0673] A04 (15.0 g, 29.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.2 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol), synthesized by the method of Preparation Example 11, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 390 (2,4-diphenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (13.6 g, 21.9 mmol, yield 75%).

[0674] Mass:[(M+H)] + ]:620

[0675] [Synthesis Example 74]: Synthesis of Compound 394

[0676] [ka]

[0677] A05 (15.0 g, 29.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.2 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol), synthesized by the method of Preparation Example 12, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 394 (2,4-diphenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (13.9 g, 22.5 mmol, yield 77%).

[0678] Mass:[(M+H)] + ]:620

[0679] [Synthesis Example 75]: Synthesis of Compound 398

[0680] [ka]

[0681] A06 (15.0 g, 29.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.2 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol), synthesized by the method of Preparation Example 13, were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 398 (2,4-diphenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (13.4 g, 21.6 mmol, yield 74%).

[0682] Mass:[(M+H)] + ]:620

[0683] [Synthesis Example 76]: Synthesis of Compound 406

[0684] [ka]

[0685] A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, B01 (10.0 g, 29.2 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) synthesized by the method of Preparation Example 15 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 406 (2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (14.6 g, 21.0 mmol, yield 72%).

[0686] Mass:[(M+H)] + ]:696

[0687] [Synthesis Example 77]: Synthesis of Compound 410

[0688] [ka]

[0689] Compound A05 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 12, compound B01 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 15, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 410(2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (14.6 g, 21.0 mmol, yield 72%).

[0690] Mass:[(M+H)] + ]:696

[0691] [Synthesis Example 78]: Synthesis of Compound 414

[0692] [ka]

[0693] Compound A06 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 13, compound B01 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 15, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 414(2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (14.6 g, 21.0 mmol, yield 72%).

[0694] Mass:[(M+H)] + ]:696

[0695] [Synthesis Example 79]: Synthesis of Compound 422

[0696] [ka]

[0697] Compound A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, compound B02 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 422(2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (14.8 g, 21.3 mmol, yield 73%).

[0698] Mass:[(M+H)] + ]:696

[0699] [Synthesis Example 80]: Synthesis of Compound 426

[0700] [ka]

[0701] Compound A05 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 12, compound B02 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 426(2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (15.2 g, 21.9 mmol, yield 75%).

[0702] Mass:[(M+H)] + ]:696

[0703] [Synthesis Example 81]: Synthesis of Compound 430

[0704] [ka]

[0705] Compound A06 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 13, compound B02 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 430 (2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (15.0 g, 21.6 mmol, yield 74%).

[0706] Mass:[(M+H)] + ]:696

[0707] [Synthesis Example 82]: Synthesis of Compound 438

[0708] [ka]

[0709] Compound A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, compound B03 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 17, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 438(2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (14.6 g, 21.0 mmol, yield 72%).

[0710] Mass:[(M+H)] + ]:696

[0711] [Synthesis Example 83]: Synthesis of Compound 442

[0712] [ka]

[0713] Compound A05 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 12, compound B03 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 17, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted over 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 442(2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (15.2 g, 21.9 mmol, yield 75%).

[0714] Mass:[(M+H)] + ]:696

[0715] [Synthesis Example 84]: Synthesis of Compound 446

[0716] [ka]

[0717] Compound A06 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 13, compound B03 (10.0 g, 29.2 mmol) synthesized by the method of Preparation Example 17, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 446(2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (14.6 g, 21.0 mmol, yield 72%).

[0718] Mass:[(M+H)] + ]:696

[0719] [Synthesis Example 85]: Synthesis of Compound 454

[0720] [ka]

[0721] Compound A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, compound B04 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 454(2-(naphthalene-1-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (14.3 g, 21.3 mmol, yield 73%).

[0722] Mass:[(M+H)] + ]:670

[0723] [Synthesis Example 86]: Synthesis of Compound 458

[0724] [ka]

[0725] Compound A05 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 12, compound B04 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 458 (2-(naphthalene-1-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (14.1 g, 21.0 mmol, yield 72%).

[0726] Mass:[(M+H)] + ]:670

[0727] [Synthesis Example 87]: Synthesis of Compound 462

[0728] [ka]

[0729] Compound A06 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 13, compound B04 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 462(2-(naphthalene-1-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (14.3 g, 21.3 mmol, yield 73%).

[0730] Mass:[(M+H)] + ]:670

[0731] [Synthesis Example 88]: Synthesis of Compound 470

[0732] [ka]

[0733] Compound A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, compound B05 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 470(2-(naphthalene-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)phenyl)-1,3,5-triazine) (14.1 g, 21.0 mmol, yield 72%).

[0734] Mass:[(M+H)] + ]:670

[0735] [Synthesis Example 89]: Synthesis of Compound 474

[0736] [ka]

[0737] Compound A05 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 12, compound B05 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 474(2-(naphthalene-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-6'-yl)phenyl)-1,3,5-triazine) (14.7 g, 21.9 mmol, yield 75%).

[0738] Mass:[(M+H)] + ]:670

[0739] [Synthesis Example 90]: Synthesis of Compound 478

[0740] [ka]

[0741] Compound A06 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 13, compound B05 (9.3 g, 29.2 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.6 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 478(2-(naphthalene-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (14.3 g, 21.3 mmol, yield 73%).

[0742] Mass:[(M+H)] + ]:670

[0743] [Synthesis Example 91]: Synthesis of Compound 486

[0744] [ka]

[0745] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B21 (11.6 g, 32.5 mmol) synthesized by the method of Preparation Example 35, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 486(2-(naphthalene-2-yl)-4-phenyl-6-(2-(2'-(pyridine-3-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)phenyl)-1,3,5-triazine) (16.0 g, 24.4 mmol, yield 75%).

[0746] Mass:[(M+H)] + ]:658

[0747] [Synthesis Example 92]: Synthesis of Compound 502

[0748] [ka]

[0749] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B22 (12.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 36 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 502 (7'-(2-(4-(2-(dibenzo[b,d]thiophen-3-yl)phenyl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (18.3 g, 24.4 mmol, yield 75%).

[0750] Mass:[(M+H)] + ]:750

[0751] [Synthesis Example 93]: Synthesis of Compound 518

[0752] [ka]

[0753] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B23 (12.2 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 37 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 518 (7'-(2-(4-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-2'-carbonitrile) (16.6 g, 24.4 mmol, yield 75%).

[0754] Mass:[(M+H)] + ]:684

[0755] [Synthesis Example 94]: Synthesis of Compound 534

[0756] [ka]

[0757] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B24 (14.1 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) synthesized by the method of Preparation Example 38 were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 534 (7'-(2-(4-phenyl-6-(2-(9-phenyl-9H-carbazole-2-yl)phenyl)-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (19.7 g, 24.4 mmol, yield 75%).

[0758] Mass:[(M+H)] + ]:809

[0759] [Synthesis Example 95]: Synthesis of Compound 550

[0760] [ka]

[0761] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B25 (14.1 g, 32.5 mmol) synthesized by the method of Preparation Example 39, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 550 (1'-(2-(4-(3-(9H-carbazole-9-yl)phenyl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (17.8 g, 24.4 mmol, yield 75%).

[0762] Mass:[(M+H)] + ]:733

[0763] [Synthesis Example 96]: Synthesis of Compound 561

[0764] [ka]

[0765] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B26 (12.1 g, 32.5 mmol) synthesized by the method of Preparation Example 40, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 561 (7'-(2-(4-(dibenzo[b,d]furan-2-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (17.8 g, 24.4 mmol, yield 75%).

[0766] Mass:[(M+H)] + ]:733

[0767] [Synthesis Example 97]: Synthesis of Compound 570

[0768] [ka]

[0769] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B27 (12.1 g, 32.5 mmol) synthesized by the method of Preparation Example 41, Pd(PPh3)4 (1.1 g, 1.0 mmol), and K2CO3 (13.5 g, 97.5 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 570 (7'-(2-(6-(dibenzo[b,d]thiophen-3-yl)-2-phenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 24.4 mmol, yield 75%).

[0770] Mass:[(M+H)] + ]:733

[0771] [Synthesis Example 98]: Synthesis of Compound 624

[0772] [ka]

[0773] Compound A07 (15.0 g, 27.9 mmol), 2-chloro-4,6-diphenylpyrimidine (7.4 g, 27.9 mmol), Pd(PPh3)4 (1.0 g, 0.8 mmol), and K2CO3 (11.6 g, 83.7 mmol), synthesized by the method of Preparation Example 14, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 624 (4-(4'-(2-(4,6-diphenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzonitrile) (13.4 g, 20.9 mmol, yield 75%).

[0774] Mass:[(M+H)] + ]:643

[0775] [Synthesis Example 99]: Synthesis of Compound 635

[0776] [ka]

[0777] Compound A07 (15.0 g, 27.9 mmol), 4-chloro-2,6-diphenylpyrimidine (7.4 g, 27.9 mmol), Pd(PPh3)4 (1.0 g, 0.8 mmol), and K2CO3 (11.6 g, 83.7 mmol), synthesized by the method of Preparation Example 14, were placed in a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted for 2 hours under heating, reflux, and stirring. After the reaction was completed, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 635 (4-(4'-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzonitrile) (13.4 g, 20.9 mmol, yield 75%).

[0778] Mass:[(M+H)] + ]:643

[0779] [Synthesis Example 100]: Synthesis of Compound 646

[0780] [ka]

[0781] 8'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile (15.0 g, 31.6 mmol), compound B28 synthesized by the method of Preparation Example 42 (13.3 g, 31.6 mmol), Pd(OAc)2 (0.2 g, 0.9 mmol), Xphos (0.9 g, 1.9 mmol), and Cs2CO3 (20.6 g, 63.2 mmol) were placed in a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted with heating and stirring for 4 hours. After the reaction was complete, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 646 (8'-(2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-2-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile) (21.0 g, 25.6 mmol, yield 81%).

[0782] Mass:[(M+H)] + ]:643

[0783] [Synthesis Example 101]: Synthesis of Compound 714

[0784] [ka]

[0785] 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile (15.0 g, 31.6 mmol), compound B29 synthesized by the method of Preparation Example 43 (16.6 g, 31.6 mmol), Pd(OAc)2 (0.2 g, 0.9 mmol), Xphos (0.9 g, 1.9 mmol), and Cs2CO3 (20.6 g, 63.2 mmol) were placed in a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted with heating and stirring for 4 hours. After the reaction was complete, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 714 (7'-(3-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)dibenzo[b,d]thiophen-1-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile) (21.1 g, 25.6 mmol, yield 81%).

[0786] Mass:[(M+H)] + ]:749

[0787] [Synthesis Example 102]: Synthesis of Compound 761

[0788] [ka]

[0789] 4-(1'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-5'-yl)pyridine (15.0 g, 31.6 mmol), compound B30 synthesized by the method of Preparation Example 44 (16.6 g, 31.6 mmol), Pd(OAc)2 (0.2 g, 0.9 mmol), Xphos (0.9 g, 1.9 mmol), and Cs2CO3 (20.6 g, 63.2 mmol) were placed in a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted with heating and stirring for 4 hours. After the reaction was complete, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 761 (2,3-diphenyl-5-(2-(1-(4'-(pyridine-4-yl)spiro[cyclohexane-1,9'-fluorene]-8'-yl)dibenzo[b,d]thiophen-3-yl)phenyl)pyrazine) (21.1 g, 25.6 mmol, yield 81%).

[0790] Mass:[(M+H)] + ]:801

[0791] [Synthesis Example 103]: Synthesis of Compound 763

[0792] [ka]

[0793] 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluorene]-4'-carbonitrile (15.0 g, 38.9 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (15.1 g, 38.9 mmol), Pd(PPh3)4 (1.3 g, 1.2 mmol), and K2CO3 (16.1 g, 116.8 mmol) were placed in a mixed solvent consisting of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted under heating, reflux, and stirring for 2 hours. After the reaction was terminated, the mixture was extracted with methylene chloride, and the extracted organic layer was concentrated after removing water with magnesium sulfate and purified by column chromatography to obtain compound 763 (2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile) (17.4 g, 30.8 mmol, yield 79%).

[0794] Mass:[(M+H)] + ]:568

[0795] [Examples and Comparative Examples]-1

[0796] [Examples 1 to 103 and Comparative Examples 1 to 7]: Fabrication of a blue organic electroluminescent device

[0797] After performing high-purity sublimation and purification of each compound synthesized in the above synthesis example using commonly known methods, a blue organic electroluminescent element was fabricated by the following process.

[0798] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. Finally, the substrate was cleaned with UV light for 5 minutes using a UV OZONE cleaning machine (Power sonic 405, Hwashin Tech) to produce a substrate with a transparent ITO electrode formed on it. The produced substrate was then transferred to a vacuum deposition machine.

[0799] An organic electroluminescent device was fabricated by sequentially stacking a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a negative electrode on the ITO transparent electrode (positive electrode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing compound A and compound B in a weight ratio of 98:2 to a thickness of 100 Å on the positive electrode; the hole transport layer was formed by depositing compound A on the hole injection layer to a thickness of 1400 Å; the hole transport auxiliary layer was formed by depositing compound C on the hole transport layer to a thickness of 50 Å; the light-emitting layer was formed by co-depositing compound D and compound E in a weight ratio of 98:2 to a thickness of 200 Å on the hole transport auxiliary layer; the electron transport auxiliary layer was formed by depositing compound F on the light-emitting layer to a thickness of 50 Å; the electron transport layer was formed by co-depositing electron transport layer material and compound H in a weight ratio of 1:1 to a thickness of 300 Å on the electron transport auxiliary layer; the electron injection layer was formed by depositing LiF on the electron transport layer to a thickness of 10 Å; and the negative electrode was formed by depositing Al on the electron injection layer to a thickness of 1000 Å. The structures of compounds A through H are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0800] [Table 1] [Table 1]

[0801] [Table 2] [Table 2-1]

[0802] [Table 2-2]

[0803] [Table 2-3]

[0804] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 103 and Comparative Examples 1 to 7.

[0805] For the organic electroluminescent elements manufactured in Examples 1 to 103 and Comparative Examples 1 to 7, a 10 mA / cm² test was applied to each of them. 2 The drive voltage, luminescence (EL) peak, and current efficiency were measured at the specified current density, and the results are shown in Table 3 below.

[0806] [Table 3] [Table 3-1]

[0807] [Table 3-2]

[0808] [Table 3-3]

[0809] Referring to Table 3, the blue organic electroluminescent devices produced in Examples 1 to 103 using the compounds according to the present invention as electron transport layer materials showed generally superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices produced in Comparative Examples 1 to 7 using compounds I to O as electron transport layer materials.

[0810] Specifically, the organic light-emitting compounds according to the present invention used in the blue organic electroluminescent devices of Examples 1 to 103 have a structure in which an azine moiety with excellent electron transport ability and stability is linked to a cyclohexylfluorene group to which a cyano group or pyridine group that increases the dipole moment is bonded. This allows for the use of compounds such as Compound I and Compound O, where the azine moiety and cyclohexylfluorene group are bonded and no cyano group or pyridine group is not included in the blue organic electroluminescent devices of Comparative Examples 1 and 7, where the azine moiety and cyclohexylfluorene group are bonded and no cyano group or pyridine group is not included in the electron transport layer material; and compounds such as Compound J, where the cyclohexylfluorene group is bonded to a cyano group and no azine moiety is not included in the electron transport layer material; and compounds such as Compound K and Compound L. When comparing the blue organic electroluminescent devices of Comparative Examples 3 and 4, which used compounds in which a cyclohexyl fluorene group is bonded to a cyano group and contains an azine moiety, but the cyclohexyl fluorene group is not bonded to the azine moiety in the ortho position, with the blue organic electroluminescent devices of Comparative Examples 5 and 6, which used compounds in which a cyclohexyl fluorene group is bonded to a cyano group or a pyridine group and contains an azine moiety, but the cyclohexyl fluorene group is directly bonded to the azine moiety without a linker, such as compound M and compound N, the blue organic electroluminescent devices of Comparative Examples 3 and 4, which used compounds in which a cyclohexyl fluorene group is bonded to a cyano group or a pyridine group and contains an azine moiety, but the cyclohexyl fluorene group is directly bonded to the azine moiety without a linker, it was found that they exhibit superior performance in terms of driving voltage and current efficiency.

[0811] [Examples and Comparative Examples]-2

[0812] [Examples 104 to 108 and Comparative Example 8]: Fabrication of a blue organic electroluminescent device

[0813] After performing high-purity sublimation and purification of each compound synthesized in the above synthesis example using commonly known methods, a blue organic electroluminescent element was fabricated by the following process.

[0814] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. Finally, the substrate was cleaned with UV light for 5 minutes using a UV OZONE cleaning machine (Power sonic 405, Hwashin Tech) to produce a substrate with a transparent ITO electrode formed on it. The produced substrate was then transferred to a vacuum deposition machine.

[0815] An organic electroluminescent device was fabricated by sequentially stacking a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a negative electrode on the ITO transparent electrode (positive electrode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing compound A and compound B in a weight ratio of 98:2 to a thickness of 100 Å on the positive electrode; the hole transport layer was formed by depositing compound A on the hole injection layer to a thickness of 1400 Å; the hole transport auxiliary layer was formed by depositing compound C on the hole transport layer to a thickness of 50 Å; the light-emitting layer was formed by co-depositing compound D and compound E in a weight ratio of 98:2 to a thickness of 200 Å on the hole transport auxiliary layer; the electron transport auxiliary layer was formed by depositing electron transport auxiliary layer material on the light-emitting layer to a thickness of 50 Å; the electron transport layer was formed by co-depositing compound G and compound H in a weight ratio of 1:1 to a thickness of 300 Å on the electron transport auxiliary layer; the electron injection layer was formed by depositing LiF on the electron transport layer to a thickness of 10 Å; and the negative electrode was formed by depositing Al on the electron injection layer to a thickness of 1000 Å. Compounds A to H are as shown in Table 1, and the electron transport auxiliary layer material is shown in Table 4 below.

[0816] [Table 4] [Table 4]

[0817] [Experimental Example 2] Performance evaluation of blue organic electroluminescent devices of Examples 104 to 108 and Comparative Example 8

[0818] For the organic electroluminescent elements produced in Examples 104 to 108 and Comparative Example 8, a current of 10 mA / cm² was applied to each of the organic electroluminescent elements produced in Examples 104 to 108 and Comparative Example 8. 2 The drive voltage, light emission peak, and current efficiency were measured at the specified current density, and the results are shown in Table 5 below.

[0819] [Table 5] [Table 5]

[0820] Referring to Table 5, the blue organic electroluminescent devices produced in Examples 104 to 108, which used the compound according to the present invention as the electron transport layer material, showed generally superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device produced in Comparative Example 8, which used compound F as the electron transport auxiliary layer material.

[0821] While embodiments of the present invention have been described above, a person of ordinary skill in the art to which the present invention pertains will understand that the present invention can be implemented in other specific forms without altering its technical idea or essential features. Therefore, it should be understood that each embodiment described above is illustrative in all respects and not restrictive.

Claims

1. Organic luminescent compounds represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 In the aforementioned chemical formula 1, X １ ~X ４ One of the following is C-(L ２ ) ｃ -R ２ The remaining ones are N or CR, respectively, and X １ ~X ４ Two or more of these are N, and R is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, and each of these is unsubstituted or substituted. R １ and R ２ are each independently hydrogen, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 1 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 1 to 40 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms or an arylamine group having 6 to 60 carbon atoms, and each of these may be unsubstituted or substitutable. L １ ~L ３ Each of these is independently a single bond, an arylene group having 6 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, and each of these is either unsubstituted or substituted. R ３ and R ４ These are, independently, an aryl group having 6 to 60 carbon atoms substituted with a cyano group, an aryl group having 6 to 60 carbon atoms substituted with a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, deuterium, or a cyano group, each of which is unsubstituted or substituted. a through c are each independent integers from 0 to 5. d is an integer between 0 and 3, and e is an integer between 0 and 4, where d + e ≥ 1.

2. X １ ~X ４ One of the following is C-(L ２ ) ｃ -R ２ The remaining ones are N or CR, respectively, and X １ ~X ４ Two or more of these are N, and R is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms. The aforementioned R １ and R ２ Each of these is independently hydrogen, a C2 to C40 alkenyl group, a C2 to C20 alkynyl group, a C3 to C20 cycloalkyl group, a C1 to C20 heterocycloalkyl group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkylsilyl group, a C6 to C30 arylsilyl group, a C1 to C20 alkylboron group, a C6 to C30 arylboron group, a C6 to C30 arylphosphine group, a C1 to C20 arylphosphine oxide group, a C6 to C30 arylphosphine oxide group, a C1 to C20 alkylamine group, or a C6 to C30 arylamine group, and these These may be unsubstituted or substituted with deuterium, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C3-C20 cycloalkyl group, a C1-C20 heterocycloalkyl group, a C1-C20 alkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkylsilyl group, a C6-C30 arylsilyl group, a C1-C20 alkylboron group, a C6-C30 arylboron group, a C6-C30 arylphosphine group, a C1-C20 alkylphosphine oxide group, a C6-C30 arylphosphine oxide group, a C1-C20 alkylamine group, or a C6-C30 arylamine group. Said L １ ~L ３ Each is independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms. The aforementioned R ３ and R ４ These are, independently, an aryl group having 6 to 30 carbon atoms substituted with a cyano group, an aryl group having 6 to 30 carbon atoms substituted with a nitrogen-containing heteroaryl group having 2 to 30 carbon atoms, a nitrogen-containing heteroaryl group having 2 to 30 carbon atoms, deuterium, or a cyano group. Each of the above a to c is an independent integer from 0 to 2, The organic luminescent compound according to claim 1, wherein d is an integer from 0 to 2, and e is an integer from 0 to 2, where d + e ≥ 1.

3. The aforementioned X １ ~X ４ One of the following is C-(L ２ ) ｃ -R ２ The remaining ones are N or CH, respectively, and X １ ~X ４ Two or more of them are N, The aforementioned R １ and R ２ Each of these is independently hydrogen, a carbon-6 to carbon-30 aryl group, or a carbon-2 to carbon-30 heteroaryl group, each of which is either unsubstituted or substituted with a carbon-3 to carbon-20 cycloalkyl group, a carbon-1 to carbon-20 alkyl group, a carbon-6 to carbon-30 aryl group, a carbon-2 to carbon-30 heteroaryl group, a carbon-1 to carbon-20 alkylsilyl group, a carbon-6 to carbon-30 arylsilyl group, a carbon-1 to carbon-20 alkylphosphine oxide group, or a carbon-6 to carbon-30 arylphosphine oxide group. Said L １ ~L ３ Each is independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms. The aforementioned R ３ and R ４ These are, independently, aryl groups having 6 to 30 carbon atoms substituted with a cyano group, nitrogen-containing heteroaryl groups having 2 to 30 carbon atoms, or cyano groups, Each of the above a to c is an independent integer from 0 to 2, The organic luminescent compound according to claim 1, wherein d is an integer from 0 to 2, and e is an integer from 0 to 2, where d + e ≥ 1.

4. The organic luminescent compound according to claim 1, wherein the chemical formula 1 is represented by any one selected from the following chemical formulas 2 to 9: [Chemical formula 2] 【Chemistry 2】 [Chemical formula 3] 【Transformation 3】 [Chemical formula 4] 【Chemistry 4】 [Chemical formula 5] 【Transformation 5】 [Chemical formula 6] 【Transformation 6】 [Chemical formula 7] 【Transformation 7】 [Chemical formula 8] 【Transformation 8】 [Chemical formula 9] 【Chemistry 9】 In each of the above chemical formulas 2 to 9, R １ and R ２ Each of these is independently hydrogen, a carbon-6 to carbon-30 aryl group, or a carbon-2 to carbon-30 heteroaryl group, each of which is either unsubstituted or substituted with a carbon-3 to carbon-20 cycloalkyl group, a carbon-1 to carbon-20 alkyl group, a carbon-6 to carbon-30 aryl group, a carbon-2 to carbon-30 heteroaryl group, a carbon-1 to carbon-20 alkylsilyl group, a carbon-6 to carbon-30 arylsilyl group, a carbon-1 to carbon-20 alkylphosphine oxide group, or a carbon-6 to carbon-30 arylphosphine oxide group. L １ ~L ３ Each is independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms. R ３ and R ４ These are, independently, aryl groups having 6 to 30 carbon atoms substituted with a cyano group, nitrogen-containing heteroaryl groups having 2 to 30 carbon atoms, or cyano groups, a through c are each independent integers from 0 to 2.

5. The organic luminescent compound according to claim 4, wherein the chemical formula 1 is represented by any one selected from the following chemical formulas 2 to 7: [Chemical formula 2] 【Chemistry 10】 [Chemical formula 3] 【Chemistry 11】 [Chemical formula 4] 【Chemistry 12】 [Chemical formula 5] 【Chemistry 13】 [Chemical formula 6] 【Chemistry 14】 [Chemical formula 7] 【Chemistry 15】 In each of the above chemical formulas 2 to 7, R １ and R ２ Each of these is independently a hydrogen, phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorenyl group, pyridyl group, carbazolyl group, dibenzothiophenyl group, or dibenzofuranyl group, each of which is either unsubstituted or substituted with a methyl group, phenyl group, cyclohexyl group, adamantyl group, pyridyl group, carbazolyl group, dibenzothiophenyl group, dibenzofuranyl group, trimethylsilyl group, triphenylsilyl group, dimethylphosphine oxide group, or diphenylphosphine oxide group. L １ ~L ３ Each of these is independently a single bond, a phenylene group, a biphenylene group, a naphthylene group, a terphenylene group, a dibenzofuranylene group, or a dibenzothiophenylene group, R ３ and R ４ These are, independently, phenyl groups, pyridyl groups, or cyano groups substituted with cyano groups, a through c are each independent integers from 0 to 2.

6. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound represented by chemical formula 1 is one selected from the following compounds 001 to 774. 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】

7. An organic electroluminescent device comprising an organic light-emitting compound according to any one of claims 1 to 6.

8. The organic electroluminescent element includes a positive electrode; a negative electrode; a light-emitting layer disposed between the negative electrode and the positive electrode; and an electron transport region disposed between the negative electrode and the light-emitting layer. The organic field light-emitting device according to claim 7, wherein the electron transport region includes the organic light-emitting compound.

9. The electron transport region includes one or more of the electron transport layer and the electron transport auxiliary layer. The organic electroluminescent element according to claim 8, wherein the organic light-emitting compound is included in one or more of the electron transport layer and the electron transport auxiliary layer.

10. Applications of organic light-emitting compounds in organic electroluminescent devices according to any one of claims 1 to 6.

11. The application according to claim 10, characterized in that the organic light-emitting compound is used as an electron transport material in the organic electroluminescent device.

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