Organic light-emitting compound, and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic light-emitting compound represented by chemical formula 1 (see the specification) and an organic electroluminescent device comprising same, which can have a high current efficiency and a low driving voltage.

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2023-0186800, filed December 20, 2023, the entire contents of which are incorporated herein by reference.

[0003] Technology field

[0004] The present invention relates to a novel organic luminescent compound and an organic electroluminescent device comprising the same.

[0005] Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices has continued, leading to blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic EL device with a laminated structure divided into functional layers of a hole layer and a light-emitting layer. Since then, in order to create high-efficiency, long-life organic EL devices, development has been made by introducing characteristic organic material layers within the device, which has led to the development of specialized materials used therefor.

[0006] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic material layer can be classified according to their function, such as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0007] The luminescent materials in organic electroluminescent devices can be categorized into blue, green, and red luminescent materials based on their emission color. Additionally, yellow and orange luminescent materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as luminescent materials to increase color purity and luminescence efficiency through energy transfer.

[0008] Dopant materials can be divided into fluorescent dopants, which utilize organic materials, and phosphorescent dopants, which utilize metal complexes containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescent materials. Therefore, extensive research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

[0009] Currently, NPB, BCP, Alq3, etc. are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and 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 improving efficiency, are being used as phosphorescent dopant materials for blue, green, and red, and 4,4-dicarbazolybiphenyl (CBP) is being used as a phosphorescent host material.

[0010] In this way, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not satisfactory in terms of the lifespan of organic electroluminescent devices.

[0011] Therefore, the development of high-performance organic layer materials is required.

[0012] Prior art literature

[0013] Republic of Korea Patent Publication No. 10-2015-0069346

[0014] The present invention aims to provide a novel compound and its use that can be used as an organic layer material of an organic electroluminescent device having excellent thermal stability, electron injection and transfer ability, and luminescence ability, specifically, an electron transport layer material and an electron transport auxiliary layer material.

[0015] In addition, the present invention aims to provide an organic electroluminescent device having significantly improved luminescence performance, driving voltage, lifespan, and efficiency by including the novel organic luminescent compound described above.

[0016] The problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0017] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0018] An organic light-emitting compound represented by the following chemical formula 1:

[0019] [Chemical Formula 1]

[0020]

[0021] In the above chemical formula 1,

[0022] Either X1 or X4 is C-(L2) c -R2, and the rest are each independently N or CR, and two or more of the X1 to X4 are N, and the 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, each of which may be unsubstituted or substituted,

[0023] R1 and R2 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 a Arylamine groups, each of which may be unsubstituted or substituted,

[0024] L1 to L3 are each independently a single bond, an arylene group having 6 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0025] R3 and R4 are each 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,

[0026] a to c are each independently integers from 0 to 5,

[0027] d is an integer from 0 to 3, and e is an integer from 0 to 4, where d+e ≥ 1.

[0028] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0029] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0030] The organic light-emitting compound according to the present invention has excellent electron injection and transfer capabilities due to its molecular structure, which includes an azine group, which is a strong electron acceptor, and thus the driving voltage of the device can be improved by improving the electron transfer capability to the light-emitting layer.

[0031] In addition, the organic light-emitting compound according to the present invention has excellent thermal stability by including an aromatic hydrocarbon group and a condensed structure rather than a simple aliphatic ring group, and is effective in improving the processability of the device as well as the lifespan because it has no crystallization temperature (Tc).

[0032] 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 connected in an ortho position via a linker, thereby improving stability and increasing a dipole moment, thereby increasing interaction with a cathode and improving electron generation within the device, thereby effectively improving driving voltage characteristics.

[0033] In addition, an organic electroluminescent device including an organic light-emitting compound according to the present invention can achieve a low driving voltage and can have significantly improved light-emitting performance, lifespan, and efficiency, and thus can be more effectively applied to full-color display panels, etc.

[0034] The effects of the present invention are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

[0035] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various different forms. These embodiments are provided solely to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the present invention, and the present invention is defined solely by the scope of the claims.

[0036] The terminology used herein is for the purpose of describing embodiments and is not intended to limit the present invention. In this specification, singular forms also include plural forms, unless specifically stated otherwise. As used herein, the terms "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0037] Unless otherwise defined, all terms (including technical and scientific terms) used herein may be used in their common sense to those skilled in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0038] Hereinafter, embodiments of the present invention will be described in detail.

[0039] Before proceeding, the meanings of terms used in this specification will be briefly explained. However, please note that the explanation of terms is intended to aid understanding of this specification and, unless explicitly stated to limit the invention, they are not intended to limit the technical spirit of the invention.

[0040] In the present invention, the term “aryl group” may mean a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may refer to, for example, a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a chrycenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, etc., but is not limited thereto. Additionally, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon.

[0041] In the present invention, the term "heteroaryl group" may mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a naphthyridyl group, an acenaphthopyridyl group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl 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 group,Nitrogen-containing heteroaryl groups including an acridinyl group, a phenanthridyl group, a carbazolyl group, a phenanthrolinyl group, a phenazinyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a pyrazolopyridyl group, a heptaazaphenalenyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples thereof include oxygen-containing heteroaryl groups such as a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzonaphthofuranyl group, an oxanthrenyl group, a xanthenyl group, and a benzoxanthenyl group; oxygen and sulfur-containing complex heteroaryl groups such as a thiadiazolyl group, an oxadiazolyl group, a phenoxathiinyl group, a benzothienopyrimidinyl group, and a benzofuropyridyl group. Also, the term "heteroarylene group" refers to heteroatoms such as nitrogen (N), sulfur (S), oxygen (O), phosphorus (P),It may refer to a divalent functional group derived from an aromatic hydrocarbon containing at least one of selenium (Se) and silicon (Si). In the heteroaryl group and heteroarylene group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may refer to the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heteroaryl group and heteroarylene group may each have a nuclear number of 5 to 60, 5 to 30, or 5 to 20.

[0042] 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 group may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1-ethylpropyl group, a 2-ethylpropyl group, an n-hexyl group, a 1-methyl-2-ethylpropyl group, a 1-ethyl-2-methylpropyl group, It may mean, but is not limited to, a 1,1,2-trimethylpropyl group, a 1-propylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a 2-methylpentyl group, and a 3-methylpentyl group.

[0043] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon having a ring structure. The cycloalkyl group may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclononyl group, and an adamantly group, but is not limited thereto.

[0044] In the present invention, the term "heterocycloalkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon having a ring structure, and the heterocycloalkyl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. In the heterocycloalkyl group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may mean the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom 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 5 to 60, 5 to 30, or 5 to 20 nuclear atoms.

[0045] In the present invention, the term “alkenyl group” may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds in the middle or terminal of an alkyl group.

[0046] 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.

[0047] In the present invention, the terms “alkylsilyl group” and “arylsilyl group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with the aforementioned alkyl group or aryl group.

[0048] In the present invention, the terms “alkylamine group” and “arylamine group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of an amine is substituted with the aforementioned alkyl group or aryl group.

[0049] In the present invention, the terms “alkylboron group” and “arylboron group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of borane is substituted with the aforementioned alkyl group or aryl group.

[0050] In the present invention, the term “arylphosphine group” may mean a monovalent functional group derived from a compound in which the aforementioned aryl group is substituted on phosphine.

[0051] In the present invention, the terms “alkylphosphine oxide group” and “arylphosphine oxide group” may each mean a monovalent functional group derived from a compound in which the aforementioned alkyl group or aryl group is substituted on a phosphine oxide.

[0052] In the present invention, the term "substitution" is independently selected from the group consisting of deuterium, an alkenyl group having 2 to 20 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, and a It means being substituted with one or more substituents selected from the group consisting of an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0053]

[0054] Organic luminescent compounds

[0055] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0056] [Chemical Formula 1]

[0057]

[0058] In the above chemical formula 1,

[0059] Either X1 or X4 is C-(L2) c -R2, and the rest are each independently N or CR, and two or more of the X1 to X4 are N, and the R is hydrogen, 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, or a heteroaryl group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0060] R1 and R2 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, a heterocycloalkyl group having 3 to 40 nuclear 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, a heteroaryl group having 5 to 60 nuclear 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, each of which may be unsubstituted or substituted,

[0061] 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, each of which may be unsubstituted or substituted.

[0062] R3 and R4 are each 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 nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms, deuterium or a cyano group, each of which may be unsubstituted or substituted,

[0063] a to c are each independently integers from 0 to 5,

[0064] d is an integer from 0 to 3, and e is an integer from 0 to 4, where d+e ≥ 1.

[0065] In the above, if a, b or c is each 0, it means that each is a single bond.

[0066] In the above, when d is 0, it means that R4 is not substituted with a hydrogen atom present in the benzene ring on which R4 can be substituted, and when e is 0, it means that R3 is not substituted with a hydrogen atom present in the benzene ring on which R3 can be substituted.

[0067] Specifically, one or more groups of hydrogen atoms, alkenyl groups, alkynyl groups, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylborone groups, alkylamine groups, arylamine groups, arylphosphine groups, alkylphosphine oxide groups and arylphosphine oxide groups that can be present in the R, R1 to R4 and L1 to L3 are each independently unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 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 aryl group having 2 to It means being substituted with one or more substituents selected from the group consisting of a heteroaryl group having 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 alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0068] In one embodiment, in the chemical formula 1,

[0069] Either X1 or X4 is C-(L2) c-R2, and the rest are each independently N or CR, and two or more of the X1 to X4 are N, and the 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,

[0070] 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, 30 arylphosphine oxide group, an alkylamine group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 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, and a It may be substituted with an arylboron group, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, or an arylamine group having 6 to 30 carbon atoms,

[0071] L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, or a heteroarylene group having 5 to 30 nuclear atoms,

[0072] R3 and R4 are each 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 nitrogen-containing heteroaryl group having 5 to 30 nuclear atoms, deuterium or a cyano group, each of which may be unsubstituted or substituted,

[0073] a to c are each independently integers from 0 to 2,

[0074] d is an integer from 0 to 2, and e is an integer from 0 to 2, where d+e ≥ 1.

[0075] In the above, if a, b or c is each 0, it means that each is a single bond.

[0076] In the above, when d is 0, it means that R4 is not substituted with a hydrogen atom present in the benzene ring on which R4 can be substituted, and when e is 0, it means that R3 is not substituted with a hydrogen atom present in the benzene ring on which R3 can be substituted.

[0077] In one embodiment, in the chemical formula 1,

[0078] Either X1 or X4 is C-(L2) c -R2, and the rest are each independently N or CH, and two or more of the above X1 to X4 are N,

[0079] 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, each of which may be 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,

[0080] L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, or a heteroarylene group having 5 to 30 nuclear atoms,

[0081] R3 and R4 are each independently an aryl group having 6 to 30 carbon atoms substituted with a cyano group, a heteroaryl group containing 2 to 30 nitrogen atoms, a heteroaryl group containing 5 to 30 nitrogen atoms, or a cyano group,

[0082] a to c are each independently integers from 0 to 2,

[0083] d is an integer from 0 to 2, and e is an integer from 0 to 2, where d+e ≥ 1.

[0084] In one embodiment, 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.

[0085] In one embodiment, 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.

[0086] In the above, if a, b or c is each 0, it means that each is a single bond.

[0087] In the above, when d is 0, it means that R4 is not substituted with a hydrogen atom present in the benzene ring on which R4 can be substituted, and when e is 0, it means that R3 is not substituted with a hydrogen atom present in the benzene ring on which R3 can be substituted.

[0088] In one embodiment, the chemical formula 1 may be represented by any one selected from the following chemical formulas 2 to 9.

[0089] [Chemical Formula 2]

[0090]

[0091] [Chemical Formula 3]

[0092]

[0093] [Chemical Formula 4]

[0094]

[0095] [Chemical Formula 5]

[0096]

[0097] [Chemical Formula 6]

[0098]

[0099] [Chemical Formula 7]

[0100]

[0101] [Chemical Formula 8]

[0102]

[0103] [Chemical Formula 9]

[0104]

[0105] In each of the above chemical formulas 2 to 9,

[0106] R1 and R2 are each independently hydrogen, 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, each of which may be 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,

[0107] L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, or a heteroarylene group having 5 to 30 nuclear atoms,

[0108] R3 and R4 are each independently an aryl group having 6 to 30 carbon atoms substituted with a cyano group, a heteroaryl group containing 2 to 30 nitrogen atoms, a heteroaryl group containing 5 to 30 nitrogen atoms, or a cyano group,

[0109] a to c are each independently integers from 0 to 2.

[0110] In the above, if a, b or c is each 0, it means that each is a single bond.

[0111] In one embodiment, the chemical formula 1 may be represented by any one selected from the following chemical formulas 2 to 7.

[0112] [Chemical Formula 2]

[0113]

[0114] [Chemical Formula 3]

[0115]

[0116] [Chemical Formula 4]

[0117]

[0118] [Chemical Formula 5]

[0119]

[0120] [Chemical Formula 6]

[0121]

[0122] [Chemical Formula 7]

[0123]

[0124] In each of the above chemical formulas 2 to 7,

[0125] R1 and R2 are each 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, and each of these may be 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,

[0126] 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,

[0127] R3 and R4 are each independently a phenyl group, a pyridyl group or a cyano group substituted with a cyano group,

[0128] a to c can each independently be an integer from 0 to 2.

[0129] In the above, if a, b, or c are each 0, it means that each is a single bond.

[0130] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one selected from compounds 001 to 774 below.

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] As a specific example, the compound represented by the above chemical formula 1 is the compound 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, 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, It may be any one selected from 550, 561, 570, 624, 635, 646, 714, 761, and 763.

[0173] The organic light-emitting compound according to the present invention has excellent electron injection and transfer capabilities due to its molecular structure, which includes an azine group, which is a strong electron acceptor, and thus the driving voltage of the device can be improved by improving the electron transfer capability to the light-emitting layer.

[0174] In addition, the organic light-emitting compound according to the present invention has excellent thermal stability by including an aromatic hydrocarbon group and a condensed structure rather than a simple aliphatic ring group, and is effective in improving the processability of the device as well as the lifespan because it has no crystallization temperature (Tc).

[0175] 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 connected in an ortho position via a linker, thereby improving stability and increasing a dipole moment, thereby increasing interaction with a cathode and improving electron generation within the device, thereby effectively improving driving voltage characteristics.

[0176] 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, luminescence peak, and current efficiency can be achieved.

[0177]

[0178] Organic electroluminescent devices

[0179] The present invention provides an organic electroluminescent device comprising the novel organic luminescent compound described above. The organic luminescent compound according to the present invention may be included in at least one of the organic layers disposed between the cathode and the anode of the organic electroluminescent device.

[0180] In one embodiment, the organic electroluminescent device comprises an anode; a cathode; a light-emitting layer disposed between the cathode and the anode; and an electron transport region disposed between the cathode and the light-emitting layer, wherein the electron transport region comprises an organic light-emitting compound according to the present invention.

[0181] anode

[0182] The organic electroluminescent device of the present invention includes an anode. The anode serves to inject holes into an organic layer. Here, the organic layer may refer to one or more layers formed between the anode and the cathode.

[0183] The type of the above-mentioned positive electrode material is not particularly limited and can be manufactured according to a conventional method known in the art. The above-mentioned positive electrode material may be, for example, a metal such as vanadium, chromium, copper, zinc and gold or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); a complex of a metal and an oxide such as ZnO:Al and SnO2:Sb; a conductive polymer such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole and polyaniline; and carbon black, etc., and each of these may be used alone or two or more types may be used in combination.

[0184] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. For example, the anode can be formed by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0185] cathode

[0186] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0187] The type of cathode material forming the above cathode is not particularly limited and can be manufactured according to a conventional method known in the art. The cathode material may be, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0188] luminescent layer

[0189] The organic electroluminescent device of the present invention includes a light-emitting layer disposed between the cathode and the anode. The light-emitting layer is a layer in which holes and electrons meet to form excitons, and the color of light emitted by the organic electroluminescent device may vary depending on the material forming the light-emitting layer.

[0190] The light-emitting material forming the above light-emitting layer can be any of a variety of commercially available materials without any particular limitation, depending on the wavelength of the desired emitted light.

[0191] In one embodiment, the light-emitting material can be classified into blue, green, red light-emitting materials, etc. according to the light-emitting color, and the light-emitting material can form a light-emitting layer by mixing a host material and a dopant material to prevent problems such as a decrease in color purity or a decrease in the efficiency of the device due to a light-emitting attenuation effect. The light-emitting efficiency of the light-emitting device can be improved by using the host material, which is the main material forming the light-emitting layer, and a small amount of dopant having a smaller energy band gap than the host material.

[0192] electron transport region

[0193] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0194] The electron transport region serves to transport electrons injected from the cathode to the light-emitting layer. This electron transport region may include at least one selected from the group consisting of an electron injection layer and an electron transport layer. In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include both the electron transport layer and the electron injection layer described above.

[0195] In the electron transport region, the electron injection layer can use an electron injection material that is easy to inject electrons from the cathode and has high electron mobility without limitation. Non-limiting examples of usable electron injection materials include the above-described bipolar compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As a specific example, the electron injection material may include at least one selected from the group consisting of LiF, Li2O, BaO, NaCl, CsF; lanthanide metals such as Yb; and halogenated metals such as RbCl, RbI.

[0196] The electron transport layer may include the organic luminescent compound according to the present invention described above. In addition, by using the novel organic luminescent compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be realized.

[0197] The above electron transport layer can be formed by mixing the organic light-emitting compound according to the present invention and Liq (lithium quinolate). Liq has a conduction band of 5.58 eV and a valence band of 3.153 eV, thereby having the effect of lowering the potential barrier.

[0198] The electron transport region can be manufactured using a conventional method known in the art. Examples of the electron transport region include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0199] electron transport auxiliary layer

[0200] The organic electroluminescent device 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.

[0201] The above electron transport auxiliary layer may include the organic luminescent compound according to the present invention described above. In addition, by using the novel organic luminescent compound according to the present invention as an electron transport auxiliary layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be realized.

[0202] The above electron transport auxiliary layer may be formed by, but is not limited to, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett method, an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, etc., as is known in the art.

[0203] hole transport region

[0204] The organic electroluminescent device of the present invention may further include a hole transport region disposed between the anode and the light-emitting layer. The hole transport region serves to move holes injected from the anode to the light-emitting layer.

[0205] The above-mentioned hole transport region may include at least one of a hole injection layer and a hole transport layer. In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include both the hole injection layer and the hole transport layer described above.

[0206] 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 high hole mobility, and any hole injection material and hole transport material used in the art can be used without limitation. The materials forming the hole injection layer and the hole transport layer may be the same or different from each other.

[0207] The hole-injecting material may be any hole-injecting material known in the art without limitation. Non-limiting examples of usable hole-injecting 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,Ndiphenylamino)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 acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), etc. It can be used alone or in combination of two or more types.

[0208] In addition, the hole transport material may be any hole transport material known in the art without limitation. Non-limiting examples of hole transport materials that can be used 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), TCTA (4,4',4"-tris(Ncarbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), etc., and these may be used alone or in combination of two or more.

[0209] The above hole transport region can be manufactured by a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0210] hole transport auxiliary layer

[0211] 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 serves to transport holes moving from the hole transport region to the light-emitting layer, and also serves to control the thickness of the organic layer. The hole transport auxiliary layer has a high LUMO value, which prevents electrons from moving to the hole transport layer, and has a high triplet (T1) energy, which prevents excitons of the light-emitting layer from diffusing to the hole transport layer.

[0212] Such a hole transport auxiliary layer may include a 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 devices may be made of the same material.

[0213] The hole transport auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives may be used. In addition, the hole transport auxiliary layer may optionally include a p-type dopant in addition to the aforementioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field may be used.

[0214] capping layer

[0215] The organic electroluminescent device of the present invention may further include a capping layer disposed on the cathode. The capping layer serves to protect the organic light-emitting device while helping light generated from the organic layer to be efficiently emitted to the outside.

[0216] The capping material forming the capping layer may include, but is not limited to, at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4'-bis[N-(1-napthyl)-N-phenyl-amion] biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 1,1'-bis(di-4-tolylaminophenyl) cyclohexane (TAPC).

[0217] The capping layer may be a single layer, but may include two or more layers having different refractive indices, so that the refractive index gradually changes as it passes through the two or more layers.

[0218] The above capping layer can be manufactured by a conventional method known in the art, and various methods such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett) method can be used, for example.

[0219]

[0220] The present invention provides a use of the organic light-emitting compound described above in an organic electroluminescent device. This provides an organic electroluminescent device with significantly improved luminescence performance, driving voltage, lifespan, and efficiency.

[0221] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0222] In one embodiment, when the organic light-emitting compound is used as an electron transport material in the organic electroluminescent device, it can be used as a material of an electron transport region.

[0223] In one embodiment, the organic light-emitting compound can be used as a material of an electron transport layer and / or an electron transport auxiliary layer in the organic electroluminescent device.

[0224]

[0225] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0226]

[0227] [Preparation]

[0228] [Preparation Example 1]: Synthesis of compound S01

[0229]

[0230] 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 added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, 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%).

[0231] Mass: [(M+H) + ] :371

[0232]

[0233] [Preparation Example 2]: Synthesis of compound S02

[0234]

[0235] 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 KCO 3(26.9 g, 194.6 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0236] Mass: [(M+H) + ] :371

[0237]

[0238] [Preparation Example 3]: Synthesis of compound S03

[0239]

[0240] 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 KCO 3( 26.9 g, 194.6 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0241] Mass: [(M+H) + ] :371

[0242]

[0243] [Preparation Example 4]: Synthesis of compound S04

[0244]

[0245] 3-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluoren]-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 K2CO 3( 23.7 g, 171.5 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S04 (3-(2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine) (21.0 g, 49.7 mmol, yield 87%).

[0246] Mass: [(M+H) + ] :423

[0247]

[0248] [Preparation Example 5]: Synthesis of compound S05

[0249]

[0250] 3-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluoren]-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 K2CO 3( 23.7 g, 171.5 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S05 (3-(3'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine) (20.7 g, 49.2 mmol, yield 86%).

[0251] Mass: [(M+H) + ] :423

[0252]

[0253] [Preparation Example 6]: Synthesis of compound S06

[0254]

[0255] 3-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluoren]-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 K2CO 3(23.7 g, 171.5 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S06 (3-(3'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine) (20.5 g, 48.6 mmol, yield 85%).

[0256] Mass: [(M+H) + ] :423

[0257]

[0258] [Preparation Example 7]: Synthesis of compound S07

[0259]

[0260] 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluoren]-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 KCO 3( 22.5 g, 162.5 mmol) was added to a mixed solvent of 250 ml of toluene, 37.5 ml of ethanol, and 37.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S07 (4-(2'-(2-chlorophenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)benzonitrile) (20.5 g, 46.1 mmol, yield 85%).

[0261] Mass: [(M+H) + ] :447

[0262]

[0263] [Preparation Example 8]: Synthesis of Compound A01

[0264]

[0265] Compound S01 (20.0 g, 54.1 mmol), bis(pinacolato)diboron (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 while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 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%).

[0266] Mass: [(M+H) + ] :462

[0267]

[0268] [Preparation Example 9]: Synthesis of Compound A02

[0269]

[0270] Compound S02 (20.0 g, 54.1 mmol), bis(pinacolato)diboron (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 while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 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%).

[0271] Mass: [(M+H) + ] :462

[0272]

[0273] [Preparation Example 10]: Synthesis of Compound A03

[0274]

[0275] Compound S03 (20.0 g, 54.1 mmol), bis(pinacolato)diboron (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 while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 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%).

[0276] Mass: [(M+H) + ] :462

[0277]

[0278] [Preparation Example 11]: Synthesis of Compound A04

[0279]

[0280] Compound S04 (20.0 g, 47.4 mmol), bis(pinacolato)diboron (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 while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A04 (3-(2'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine) (18.4 g, 39.8 mmol, yield 84%).

[0281] Mass: [(M+H) + ] :462

[0282]

[0283] [Preparation Example 12]: Synthesis of Compound A05

[0284]

[0285] Compound S05 (20.0 g, 47.4 mmol), bis(pinacolato)diboron (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 while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A05 (3-(3'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine)(17.9 g, 38.9 mmol, yield 82%).

[0286] Mass: [(M+H) + ] :462

[0287]

[0288] [Preparation Example 13]: Synthesis of Compound A06

[0289]

[0290] Compound S06 (20.0 g, 47.4 mmol), bis(pinacolato)diboron (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 while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A06 (3-(4'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)pyridine) (18.2 g, 39.3 mmol, yield 83%).

[0291] Mass: [(M+H) + ] :462

[0292]

[0293] [Preparation Example 14]: Synthesis of Compound A07

[0294]

[0295] S07 (20.0 g, 44.8 mmol), bis(pinacolato)diboron (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 while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A07 (4-(2'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)benzonitrile) (20.0 g, 37.2 mmol, yield 83%).

[0296] Mass: [(M+H) + ] :539

[0297]

[0298] [Preparation Example 15]: Synthesis of Compound B01

[0299]

[0300] 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 KCO 3(22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0301] Mass: [(M+H) + ] :345

[0302]

[0303] [Preparation Example 16]: Synthesis of Compound B02

[0304]

[0305] 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 KCO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0306] Mass: [(M+H)+ ] :345

[0307]

[0308] [Preparation Example 17]: Synthesis of Compound B03

[0309]

[0310] 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 KCO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0311] Mass: [(M+H) + ] :345

[0312]

[0313] [Preparation Example 18]: Synthesis of Compound B04

[0314]

[0315] 4,4,5,5-tetramethyl-2-(naphthalen-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) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B04 (2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine) (15.9 g, 50.2 mmol, yield 85%).

[0316] Mass: [(M+H) + ] :319

[0317]

[0318] [Preparation Example 19]: Synthesis of Compound B05

[0319]

[0320] 4,4,5,5-tetramethyl-2-(naphthalen-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 K2CO 3( 24.5 g, 177.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B05 (2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine) (15.8 g, 49.6 mmol, yield 84%).

[0321] Mass: [(M+H)+ ] :319

[0322]

[0323] [Preparation Example 20]: Synthesis of Compound B06

[0324]

[0325] 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 K2CO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0326] Mass: [(M+H) + ] :344

[0327]

[0328] [Preparation Example 21]: Synthesis of Compound B07

[0329]

[0330] 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 K2CO 3(22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0331] Mass: [(M+H) + ] :344

[0332]

[0333] [Preparation Example 22]: Synthesis of Compound B08

[0334]

[0335] 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 K2CO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0336] Mass: [(M+H) + ] :344

[0337]

[0338] [Preparation Example 23]: Synthesis of Compound B09

[0339]

[0340] 4,4,5,5-tetramethyl-2-(naphthalen-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 K2CO 3( 24.5 g, 177.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B09 (2-chloro-4-(naphthalen-1-yl)-6-phenylpyrimidine) (15.7 g, 49.6 mmol, yield 84%).

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

[0342]

[0343] [Preparation Example 24]: Synthesis of Compound B10

[0344]

[0345] 4,4,5,5-tetramethyl-2-(naphthalen-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 K2CO 3(24.5 g, 177.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B10 (2-chloro-4-(naphthalen-2-yl)-6-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0346] Mass: [(M+H) + ] :318

[0347]

[0348] [Preparation Example 25]: Synthesis of Compound B11

[0349]

[0350] 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 K2CO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0351] Mass: [(M+H) + ] :344

[0352]

[0353] [Preparation Example 26]: Synthesis of Compound B12

[0354]

[0355] 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 K2CO 3( 22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0356] Mass: [(M+H) + ] :344

[0357]

[0358] [Preparation Example 27]: Synthesis of Compound B13

[0359]

[0360] 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 K2CO 3(22.2 g, 160.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0361] Mass: [(M+H) + ] :344

[0362]

[0363] [Preparation Example 28]: Synthesis of Compound B14

[0364]

[0365] 4,4,5,5-tetramethyl-2-(naphthalen-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 K2CO 3( 24.5 g, 177.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B14 (4-chloro-6-(naphthalen-1-yl)-2-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0366] Mass: [(M+H) + ] :318

[0367]

[0368] [Preparation Example 29]: Synthesis of Compound B15

[0369]

[0370] 4,4,5,5-tetramethyl-2-(naphthalen-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 K2CO 3( 24.5 g, 177.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B15 (4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine) (15.5 g, 49.0 mmol, yield 83%).

[0371] Mass: [(M+H) + ] :318

[0372]

[0373] [Preparation Example 30]: Synthesis of Compound B16

[0374]

[0375] 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 K2CO 3(30.5 g, 220.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0376] Mass: [(M+H) + ] :344

[0377]

[0378] [Preparation Example 31]: Synthesis of Compound B17

[0379]

[0380] 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 K2CO 3( 30.5 g, 220.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0381] Mass: [(M+H) + ] :344

[0382]

[0383] [Preparation Example 32]: Synthesis of Compound B18

[0384]

[0385] 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 K2CO 3( 30.5 g, 220.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0386] Mass: [(M+H) + ] :344

[0387]

[0388] [Preparation Example 33]: Synthesis of Compound B19

[0389]

[0390] 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 K2CO 3(30.5 g, 220.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B19 (4-chloro-2-(naphthalen-1-yl)-6-phenylpyrimidine) (19.1 g, 60.3 mmol, yield 82%).

[0391] Mass: [(M+H) + ] :318

[0392]

[0393] [Preparation Example 34]: Synthesis of Compound B20

[0394]

[0395] 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 K2CO 3( 30.5 g, 220.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B20 (4-chloro-2-(naphthalen-2-yl)-6-phenylpyrimidine) (19.3 g, 61.0 mmol, yield 83%).

[0396] Mass: [(M+H) + ] :318

[0397]

[0398] [Preparation Example 35]: Synthesis of Compound B21

[0399]

[0400] 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 g) mmol) and KCO 3( 21.1 g, 153.0 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0401] Mass: [(M+H) + ] :339

[0402]

[0403] [Preparation Example 36]: Synthesis of Compound B22

[0404]

[0405] 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) mmol) and KCO 3(20.0 g, 145.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0406] Mass: [(M+H) + ] :375

[0407]

[0408] [Preparation Example 37]: Synthesis of Compound B23

[0409]

[0410] 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 KCO 3( 19.4 g, 140.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0411] Mass: [(M+H) + ] :385

[0412]

[0413] [Preparation Example 38]: Synthesis of Compound B24

[0414]

[0415] 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 KCO 3( 16.8 g, 121.9 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B24 (3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole) (14.8 g, 34.1 mmol, yield 84%).

[0416] Mass: [(M+H) + ] :434

[0417]

[0418] [Preparation Example 39]: Synthesis of Compound B25

[0419]

[0420] 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 KCO 3( 16.8 g, 121.9 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B25 (9-(3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole) (14.8 g, 34.1 mmol, yield 84%).

[0421] Mass: [(M+H) + ] :434

[0422]

[0423] [Preparation Example 40]: Synthesis of Compound B26

[0424]

[0425] 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 K2CO 3(21.1 g, 153.0 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0426] Mass: [(M+H) + ] :374

[0427]

[0428] [Preparation Example 41]: Synthesis of Compound B27

[0429]

[0430] 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 KCO 3( 20.0 g, 145.1 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0431] Mass: [(M+H)+ ] :374

[0432]

[0433] [Preparation Example 42]: Synthesis of Compound B28

[0434]

[0435] 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 KCO 3( 23.8 g, 172.3 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0436] Mass: [(M+H) + ] :421

[0437]

[0438] [Preparation Example 43]: Synthesis of Compound B29

[0439]

[0440] 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 KCO 3( 23.9 g, 172.7 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0441] Mass: [(M+H) + ] :423

[0442]

[0443] [Preparation Example 44]: Synthesis of Compound B30

[0444]

[0445] 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 KCO 3(23.9 g, 172.7 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0446] Mass: [(M+H) + ] :526

[0447]

[0448] [Synthesis example]

[0449] [Synthesis Example 1]: Synthesis of Compound 006

[0450]

[0451] 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 K2CO synthesized by the method of Preparation Example 8 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 006(7'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(13.3 g, 23.4 mmol, yield 72%).

[0452] Mass: [(M+H) + ] :568

[0453]

[0454] [Synthesis Example 2]: Synthesis of Compound 010

[0455]

[0456] 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 K2CO synthesized by the method of Preparation Example 9 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 010(6'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(13.8 g, 24.4 mmol, yield 75%).

[0457] Mass: [(M+H) + ] :568

[0458]

[0459] [Synthesis Example 3]: Synthesis of Compound 014

[0460]

[0461] 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 K2CO synthesized by the method of Preparation Example 10 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 014(5'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(13.4 g, 23.7 mmol, yield 73%).

[0462] Mass: [(M+H) + ] :568

[0463]

[0464] [Synthesis Example 4]: Synthesis of Compound 022

[0465]

[0466] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 022(2'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.7 g, 23.7 mmol, yield 75%).

[0467] Mass: [(M+H) + ] :644

[0468]

[0469] [Synthesis Example 5]: Synthesis of Compound 026

[0470]

[0471] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 026(6'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.5 g, 24.7 mmol, yield 74%).

[0472] Mass: [(M+H) + ] :644

[0473]

[0474] [Synthesis Example 6]: Synthesis of Compound 030

[0475]

[0476] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 030(5'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0477] Mass: [(M+H) + ] :644

[0478]

[0479] [Synthesis Example 7]: Synthesis of Compound 038

[0480]

[0481] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 038(2'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(16.4 g, 23.7 mmol, yield 73%).

[0482] Mass: [(M+H) + ] :644

[0483]

[0484] [Synthesis Example 8]: Synthesis of Compound 042

[0485]

[0486] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 042(6'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.7 g, 24.1 mmol, yield 74%).

[0487] Mass: [(M+H) + ] :644

[0488]

[0489] [Synthesis Example 9]: Synthesis of Compound 046

[0490]

[0491] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 046(5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.4 g, 23.7 mmol, yield 73%).

[0492] Mass: [(M+H) + ] :644

[0493]

[0494] [Synthesis Example 10]: Synthesis of Compound 054

[0495]

[0496] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 054(2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0497] Mass: [(M+H) + ] :644

[0498]

[0499] [Synthesis Example 11]: Synthesis of Compound 058

[0500]

[0501] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 058(6'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.7 g, 23.1 mmol, yield 74%).

[0502] Mass: [(M+H) + ] :644

[0503]

[0504] [Synthesis Example 12]: Synthesis of Compound 062

[0505]

[0506] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 062(5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(17.1 g, 24.7 mmol, yield 76%).

[0507] Mass: [(M+H) + ] :644

[0508]

[0509] [Synthesis Example 13]: Synthesis of Compound 070

[0510]

[0511] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B02 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 070(7'-(2-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.9 g, 24.4 mmol, yield 75%).

[0512] Mass: [(M+H) + ] :618

[0513]

[0514] [Synthesis Example 14]: Synthesis of Compound 074

[0515]

[0516] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B04 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 074(6'-(2-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(17.3 g, 25.0 mmol, yield 77%).

[0517] Mass: [(M+H) + ] :618

[0518]

[0519] [Synthesis Example 15]: Synthesis of Compound 078

[0520]

[0521] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B04 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 078(5'-(2-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.7 g, 24.1 mmol, yield 74%).

[0522] Mass: [(M+H) + ] :618

[0523]

[0524] [Synthesis Example 16]: Synthesis of Compound 086

[0525]

[0526] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B05 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 086(7'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0527] Mass: [(M+H) + ] :618

[0528]

[0529] [Synthesis Example 17]: Synthesis of Compound 090

[0530]

[0531] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B05 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 090(6'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0532] Mass: [(M+H) + ] :618

[0533]

[0534] [Synthesis Example 18]: Synthesis of Compound 094

[0535]

[0536] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B05 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 19, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 094(5'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0537] Mass: [(M+H) + ] :618

[0538]

[0539] [Synthesis Example 19]: Synthesis of Compound 102

[0540]

[0541] 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 K2CO synthesized by the method of Preparation Example 8 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 102 (7'-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0542] Mass: [(M+H) + ] :567

[0543]

[0544] [Synthesis Example 20]: Synthesis of Compound 106

[0545]

[0546] 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 K2CO synthesized by the method of Preparation Example 9 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 106 (6'-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.4 g, 23.7 mmol, yield 73%).

[0547] Mass: [(M+H) + ] :567

[0548]

[0549] [Synthesis Example 21]: Synthesis of Compound 110

[0550]

[0551] 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 K2CO synthesized by the method of Preparation Example 10 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 110 (5'-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (16.7 g, 24.1 mmol, yield 74%).

[0552] Mass: [(M+H) + ] :567

[0553]

[0554] [Synthesis Example 22]: Synthesis of Compound 118

[0555]

[0556] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 118(2'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0557] Mass: [(M+H) + ] :643

[0558]

[0559] [Synthesis Example 23]: Synthesis of Compound 122

[0560]

[0561] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 122(6'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.9 g, 24.4 mmol, yield 75%).

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

[0563]

[0564] [Synthesis Example 24]: Synthesis of Compound 126

[0565]

[0566] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 126(5'-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0567] Mass: [(M+H) + ] :643

[0568]

[0569] [Synthesis Example 25]: Synthesis of Compound 134

[0570]

[0571] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 134(2'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(16.4 g, 23.7 mmol, yield 73%).

[0572] Mass: [(M+H) + ] :643

[0573]

[0574] [Synthesis Example 26]: Synthesis of Compound 138

[0575]

[0576] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 138(6'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0577] Mass: [(M+H) + ] :643

[0578]

[0579] [Synthesis Example 27]: Synthesis of Compound 142

[0580]

[0581] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 142(5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.4 g, 23.7 mmol, yield 73%).

[0582] Mass: [(M+H) + ] :643

[0583]

[0584] [Synthesis Example 28]: Synthesis of Compound 150

[0585]

[0586] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 150(2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(16.2 g, 23.4 mmol, yield 72%).

[0587] Mass: [(M+H) + ] :643

[0588]

[0589] [Synthesis Example 29]: Synthesis of Compound 154

[0590]

[0591] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 154(6'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.9 g, 24.4 mmol, yield 75%).

[0592] Mass: [(M+H) + ] :643

[0593]

[0594] [Synthesis Example 30]: Synthesis of Compound 158

[0595]

[0596] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 158 (5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.4 g, 23.7 mmol, yield 73%).

[0597] Mass: [(M+H) + ] :643

[0598]

[0599] [Synthesis Example 31]: Synthesis of Compound 166

[0600]

[0601] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 166(7'-(2-(4-(naphthalen-1-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.4 g, 23.4 mmol, yield 72%).

[0602] Mass: [(M+H) + ] :617

[0603]

[0604] [Synthesis Example 32]: Synthesis of Compound 170

[0605]

[0606] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 170(6'-(2-(4-(naphthalen-1-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 24.4 mmol, yield 75%).

[0607] Mass: [(M+H) + ] :617

[0608]

[0609] [Synthesis Example 33]: Synthesis of Compound 174

[0610]

[0611] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 174 (5'-(2-(4-(naphthalen-1-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.6 g, 23.7 mmol, yield 73%).

[0612] Mass: [(M+H) + ] :617

[0613]

[0614] [Synthesis Example 34]: Synthesis of Compound 182

[0615]

[0616] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 182 (7'-(2-(4-(naphthalen-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.0 g, 24.4 mmol, yield 75%).

[0617] Mass: [(M+H) + ] :617

[0618]

[0619] [Synthesis Example 35]: Synthesis of Compound 186

[0620]

[0621] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 186(6'-(2-(4-(naphthalen-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.8 g, 24.1 mmol, yield 74%).

[0622] Mass: [(M+H) + ] :617

[0623]

[0624] [Synthesis Example 36]: Synthesis of Compound 190

[0625]

[0626] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 190 (5'-(2-(4-(naphthalen-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.4 g, 23.4 mmol, yield 72%).

[0627] Mass: [(M+H) + ] :617

[0628]

[0629] [Synthesis Example 37]: Synthesis of Compound 198

[0630]

[0631] 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 K2CO synthesized by the method of Preparation Example 8 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 198 (7'-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(13.4 g, 23.7 mmol, yield 73%).

[0632] Mass: [(M+H) + ] :567

[0633]

[0634] [Synthesis Example 38]: Synthesis of Compound 202

[0635]

[0636] 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 K2CO synthesized by the method of Preparation Example 9 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 202 (6'-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.6 g, 24.1 mmol, yield 74%).

[0637] Mass: [(M+H) + ] :567

[0638]

[0639] [Synthesis Example 39]: Synthesis of Compound 206

[0640]

[0641] Compound A03 (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 K2CO synthesized by the method of Preparation Example 102 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 206 (5'-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0642] Mass: [(M+H) + ] :567

[0643]

[0644] [Synthesis Example 40]: Synthesis of Compound 214

[0645]

[0646] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 214(2'-(2-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0647] Mass: [(M+H) + ] :643

[0648]

[0649] [Synthesis Example 41]: Synthesis of Compound 218

[0650]

[0651] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 218(6'-(2-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.4 g, 24.1 mmol, yield 74%).

[0652] Mass: [(M+H) + ] :643

[0653]

[0654] [Synthesis Example 42]: Synthesis of Compound 222

[0655]

[0656] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B11 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 25 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0657] Mass: [(M+H) + ] :643

[0658]

[0659] [Synthesis Example 43]: Synthesis of Compound 230

[0660]

[0661] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, compound B12 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 262, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 230 (2'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.6 g, 24.4 mmol, yield 75%).

[0662] Mass: [(M+H) + ] :643

[0663]

[0664] [Synthesis Example 44]: Synthesis of Compound 234

[0665]

[0666] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B12 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 26, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 234(6'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.1 g, 25.0 mmol, yield 77%).

[0667] Mass: [(M+H) + ] :643

[0668]

[0669] [Synthesis Example 45]: Synthesis of Compound 238

[0670]

[0671] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, Compound B12 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 26 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 238 (5'-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.4 g, 24.1 mmol, yield 74%).

[0672] Mass: [(M+H) + ] :643

[0673]

[0674] [Synthesis Example 46]: Synthesis of Compound 246

[0675]

[0676] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 246(2'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0677] Mass: [(M+H) + ] :643

[0678]

[0679] [Synthesis Example 47]: Synthesis of Compound 250

[0680]

[0681] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 250(6'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0682] Mass: [(M+H) + ] :643

[0683]

[0684] [Synthesis Example 48]: Synthesis of Compound 254

[0685]

[0686] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B13 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 27 (10.3 g, 32.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 254(5'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0687] Mass: [(M+H) + ] :643

[0688]

[0689] [Synthesis Example 49]: Synthesis of Compound 262

[0690]

[0691] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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%).

[0692] Mass: [(M+H) + ] :617

[0693]

[0694] [Synthesis Example 50]: Synthesis of Compound 266

[0695]

[0696] Compound A02 (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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 266(6'-(2-(6-(naphthalen-1-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 24.4 mmol, yield 75%).

[0697] Mass: [(M+H) + ] :617

[0698]

[0699] [Synthesis Example 51]: Synthesis of Compound 270

[0700]

[0701] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 270 (5'-(2-(6-(naphthalen-1-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.8 g, 24.1 mmol, yield 74%).

[0702] Mass: [(M+H) + ] :617

[0703]

[0704] [Synthesis Example 52]: Synthesis of Compound 278

[0705]

[0706] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 278 (7'-(2-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.4 g, 23.4 mmol, yield 72%).

[0707] Mass: [(M+H) + ] :617

[0708]

[0709] [Synthesis Example 53]: Synthesis of Compound 282

[0710]

[0711] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 282(6'-(2-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 24.4 mmol, yield 75%).

[0712] Mass: [(M+H) + ] :617

[0713]

[0714] [Synthesis Example 54]: Synthesis of Compound 286

[0715]

[0716] 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 K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 286 (5'-(2-(6-(naphthalen-1-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (14.4 g, 23.4 mmol, yield 72%).

[0717] Mass: [(M+H) + ] :617

[0718]

[0719] [Synthesis Example 55]: Synthesis of Compound 294

[0720]

[0721] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 294(2'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0722] Mass: [(M+H) + ] :643

[0723]

[0724] [Synthesis Example 56]: Synthesis of Compound 298

[0725]

[0726] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 298 (6'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.6 g, 24.4 mmol, yield 75%).

[0727] Mass: [(M+H) + ] :643

[0728]

[0729] [Synthesis Example 57]: Synthesis of Compound 302

[0730]

[0731] Compound A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 302(5'-(2-(2-([1,1'-biphenyl]-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.2 g, 23.7 mmol, yield 73%).

[0732] Mass: [(M+H) + ] :643

[0733]

[0734] [Synthesis Example 58]: Synthesis of Compound 310

[0735]

[0736] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B17 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 31, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 310(2'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0737] Mass: [(M+H) + ] : 643

[0738]

[0739] [Synthesis Example 59]: Synthesis of Compound 314

[0740]

[0741] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B17 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 31, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 314(6'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.6 g, 24.4 mmol, yield 75%).

[0742] Mass: [(M+H) + ] : 643

[0743]

[0744] [Synthesis Example 60]: Synthesis of Compound 318

[0745]

[0746] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, compound B17 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 31, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 318 (5'-(2-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.2 g, 23.7 mmol, yield 73%).

[0747] Mass: [(M+H) + ] : 643

[0748]

[0749] [Synthesis Example 61]: Synthesis of Compound 326

[0750]

[0751] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B18 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 32, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 326(2'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(15.6 g, 24.4 mmol, yield 75%).

[0752] Mass: [(M+H) + ] : 643

[0753]

[0754] [Synthesis Example 62]: Synthesis of Compound 330

[0755]

[0756] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B18 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 32, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 330(6'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.4 g, 24.1 mmol, yield 74%).

[0757] Mass: [(M+H) + ] : 643

[0758]

[0759] [Synthesis Example 63]: Synthesis of Compound 334

[0760]

[0761] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B18 (11.1 g, 32.5 mmol) synthesized by the method of Preparation Example 32, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 334(5'-(2-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(15.0 g, 23.4 mmol, yield 72%).

[0762] Mass: [(M+H) + ] : 643

[0763]

[0764] [Synthesis Example 64]: Synthesis of Compound 342

[0765]

[0766] A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B19 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 33, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 342(7'-(2-(2-(naphthalen-1-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.6 g, 23.7 mmol, yield 73%).

[0767] Mass: [(M+H) + ] : 617

[0768]

[0769] [Synthesis Example 65]: Synthesis of Compound 346

[0770]

[0771] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B19 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 33, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 346(6'-(2-(2-(naphthalen-1-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.6 g, 23.7 mmol, yield 73%).

[0772] Mass: [(M+H) + ] : 617

[0773]

[0774] [Synthesis Example 66]: Synthesis of Compound 350

[0775]

[0776] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B19 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 33, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 350(5'-(2-(2-(naphthalen-1-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.6 g, 23.7 mmol, yield 73%).

[0777] Mass: [(M+H) + ] : 617

[0778]

[0779] [Synthesis Example 67]: Synthesis of Compound 358

[0780]

[0781] Compound A01 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 8, B20 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 34, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 358 (7'-(2-(2-(naphthalen-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.4 g, 23.4 mmol, yield 72%).

[0782] Mass: [(M+H) + ] : 617

[0783]

[0784] [Synthesis Example 68]: Synthesis of Compound 362

[0785]

[0786] A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, B20 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 34, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 362(6'-(2-(2-(naphthalen-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(14.8 g, 24.1 mmol, yield 74%).

[0787] Mass: [(M+H) + ] : 617

[0788]

[0789] [Synthesis Example 69]: Synthesis of Compound 366

[0790]

[0791] A03 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 10, B20 (10.3 g, 32.5 mmol) synthesized by the method of Preparation Example 34, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 366 (5'-(2-(2-(naphthalen-2-yl)-6-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (15.2 g, 24.7 mmol, yield 76%).

[0792] Mass: [(M+H) + ] : 617

[0793]

[0794] [Synthesis Example 70]: Synthesis of Compound 374

[0795]

[0796] 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 K2CO synthesized by the method of Preparation Example 8 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 374 (7'-(2-(3,5-diphenylpyrazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0797] Mass: [(M+H) + ] :567

[0798]

[0799] [Synthesis Example 71]: Synthesis of Compound 378

[0800]

[0801] 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 K2CO synthesized by the method of Preparation Example 9 3( 13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 378 (6'-(2-(3,5-diphenylpyrazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.2 g, 23.4 mmol, yield 72%).

[0802] Mass: [(M+H) + ] :567

[0803]

[0804] [Synthesis Example 72]: Synthesis of Compound 382

[0805]

[0806] 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 K2CO synthesized by the method of Preparation Example 10 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 382 (5'-(2-(3,5-diphenylpyrazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile) (13.4 g, 23.7 mmol, yield 73%).

[0807] Mass: [(M+H) + ] :567

[0808]

[0809] [Synthesis Example 73]: Synthesis of Compound 390

[0810]

[0811] 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 K2CO synthesized by the method of Preparation Example 11 3( 12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 390 (2,4-diphenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(13.6 g, 21.9 mmol, yield 75%).

[0812] Mass: [(M+H) + ] : 620

[0813]

[0814] [Synthesis Example 74]: Synthesis of Compound 394

[0815]

[0816] 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 K2CO synthesized by the method of Preparation Example 12 3( 12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 394 (2,4-diphenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(13.9 g, 22.5 mmol, yield 77%).

[0817] Mass: [(M+H) + ] : 620

[0818]

[0819] [Synthesis Example 75]: Synthesis of Compound 398

[0820]

[0821] 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 K2CO synthesized by the method of Preparation Example 13 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 398 (2,4-diphenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(13.4 g, 21.6 mmol, yield 74%).

[0822] Mass: [(M+H) + ] : 620

[0823]

[0824] [Synthesis Example 76]: Synthesis of Compound 406

[0825]

[0826] A04 (15.0 g, 29.2 mmol) synthesized by the method of Preparation Example 11, 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 K2CO 3( 12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 406 (2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(14.6 g, 21.0 mmol, yield 72%).

[0827] Mass: [(M+H) + ] : 696

[0828]

[0829] [Synthesis Example 77]: Synthesis of Compound 410

[0830]

[0831] 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 K2CO 3( 12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 410 (2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(14.6 g, 21.0 mmol, yield 72%).

[0832] Mass: [(M+H) + ] : 696

[0833]

[0834] [Synthesis Example 78]: Synthesis of Compound 414

[0835]

[0836] 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) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 414 (2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(14.6 g, 21.0 mmol, yield 72%).

[0837] Mass: [(M+H) + ] : 696

[0838]

[0839] [Synthesis Example 79]: Synthesis of Compound 422

[0840]

[0841] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 422 (2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(14.8 g, 21.3 mmol, yield 73%).

[0842] Mass: [(M+H) + ] : 696

[0843]

[0844] [Synthesis Example 80]: Synthesis of Compound 426

[0845]

[0846] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 426 (2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(15.2 g, 21.9 mmol, yield 75%).

[0847] Mass: [(M+H) + ] : 696

[0848]

[0849] [Synthesis Example 81]: Synthesis of Compound 430

[0850]

[0851] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 430 (2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(15.0 g, 21.6 mmol, yield 74%).

[0852] Mass: [(M+H) + ] : 696

[0853]

[0854] [Synthesis Example 82]: Synthesis of Compound 438

[0855]

[0856] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 438 (2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(14.6 g, 21.0 mmol, yield 72%).

[0857] Mass: [(M+H) + ] : 696

[0858]

[0859] [Synthesis Example 83]: Synthesis of Compound 442

[0860]

[0861] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 442 (2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(15.2 g, 21.9 mmol, yield 75%).

[0862] Mass: [(M+H) + ] : 696

[0863]

[0864] [Synthesis Example 84]: Synthesis of Compound 446

[0865]

[0866] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 446 (2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(14.6 g, 21.0 mmol, yield 72%).

[0867] Mass: [(M+H) + ] : 696

[0868]

[0869] [Synthesis Example 85]: Synthesis of Compound 454

[0870]

[0871] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 454 (2-(naphthalen-1-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(14.3 g, 21.3 mmol, yield 73%).

[0872] Mass: [(M+H) + ] : 670

[0873]

[0874] [Synthesis Example 86]: Synthesis of Compound 458

[0875]

[0876] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 458 (2-(naphthalen-1-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(14.1 g, 21.0 mmol, yield 72%).

[0877] Mass: [(M+H) + ] : 670

[0878]

[0879] [Synthesis Example 87]: Synthesis of Compound 462

[0880]

[0881] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 462 (2-(naphthalen-1-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(14.3 g, 21.3 mmol, yield 73%).

[0882] Mass: [(M+H) + ] : 670

[0883]

[0884] [Synthesis Example 88]: Synthesis of Compound 470

[0885]

[0886] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 470 (2-(naphthalen-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine)(14.1 g, 21.0 mmol, yield 72%).

[0887] Mass: [(M+H) + ] : 670

[0888]

[0889] [Synthesis Example 89]: Synthesis of Compound 474

[0890]

[0891] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 474 (2-(naphthalen-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-6'-yl)phenyl)-1,3,5-triazine)(14.7 g, 21.9 mmol, yield 75%).

[0892] Mass: [(M+H) + ] : 670

[0893]

[0894] [Synthesis Example 90]: Synthesis of Compound 478

[0895]

[0896] 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 K2CO 3(12.1 g, 87.6 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 478 (2-(naphthalen-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(14.3 g, 21.3 mmol, yield 73%).

[0897] Mass: [(M+H) + ] : 670

[0898]

[0899] [Synthesis Example 91]: Synthesis of Compound 486

[0900]

[0901] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 486 (2-(naphthalen-2-yl)-4-phenyl-6-(2-(2'-(pyridin-3-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)phenyl)-1,3,5-triazine)(16.0 g, 24.4 mmol, yield 75%).

[0902] Mass: [(M+H) + ] : 658

[0903]

[0904] [Synthesis Example 92]: Synthesis of Compound 502

[0905]

[0906] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B22 (12.2 g, 32.5 mmol) synthesized by the method of Preparation Example 36, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, 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-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(18.3 g, 24.4 mmol, yield 75%).

[0907] Mass: [(M+H) + ] : 750

[0908]

[0909] [Synthesis Example 93]: Synthesis of Compound 518

[0910]

[0911] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B23 (12.2 g, 32.5 mmol) synthesized by the method of Preparation Example 37, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 518(7'-(2-(4-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.6 g, 24.4 mmol, yield 75%).

[0912] Mass: [(M+H) + ] : 684

[0913]

[0914] [Synthesis Example 94]: Synthesis of Compound 534

[0915]

[0916] Compound A02 (15.0 g, 32.5 mmol) synthesized by the method of Preparation Example 9, compound B24 (14.1 g, 32.5 mmol) synthesized by the method of Preparation Example 38, Pd(PPh3)4 (1.1 g, 1.0 mmol) and K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 534(7'-(2-(4-phenyl-6-(2-(9-phenyl-9H-carbazol-2-yl)phenyl)-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(19.7 g, 24.4 mmol, yield 75%).

[0917] Mass: [(M+H) + ] : 809

[0918]

[0919] [Synthesis Example 95]: Synthesis of Compound 550

[0920]

[0921] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 550(1'-(2-(4-(3-(9H-carbazol-9-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(17.8 g, 24.4 mmol, yield 75%).

[0922] Mass: [(M+H) + ] : 733

[0923]

[0924] [Synthesis Example 96]: Synthesis of Compound 561

[0925]

[0926] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 561(7'-(2-(4-(dibenzo[b,d]furan-2-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(17.8 g, 24.4 mmol, yield 75%).

[0927] Mass: [(M+H) + ] : 733

[0928]

[0929] [Synthesis Example 97]: Synthesis of Compound 570

[0930]

[0931] 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 K2CO 3(13.5 g, 97.5 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 570(7'-(2-(6-(dibenzo[b,d]thiophen-3-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carbonitrile)(16.4 g, 24.4 mmol, yield 75%).

[0932] Mass: [(M+H) + ] : 733

[0933]

[0934] [Synthesis Example 98]: Synthesis of Compound 624

[0935]

[0936] 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 K2CO synthesized by the method of Preparation Example 14 3(11.6 g, 83.7 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 624 (4-(4'-(2-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)benzonitrile)(13.4 g, 20.9 mmol, yield 75%).

[0937] Mass: [(M+H) + ] : 643

[0938]

[0939] [Synthesis Example 99]: Synthesis of Compound 635

[0940]

[0941] 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 K2CO synthesized by the method of Preparation Example 14 3( 11.6 g, 83.7 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 635 (4-(4'-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluoren]-7'-yl)benzonitrile)(13.4 g, 20.9 mmol, yield 75%).

[0942] Mass: [(M+H) + ] : 643

[0943]

[0944] [Synthesis Example 100]: Synthesis of Compound 646

[0945]

[0946] 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) and compound B28 (13.3 g, 31.6 mmol) synthesized by the method of Preparation Example 42, 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 added to 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 completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 646 (8'-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile) (21.0 g, 25.6 mmol, yield 81%).

[0947] Mass: [(M+H) + ] : 643

[0948]

[0949] [Synthesis Example 101]: Synthesis of Compound 714

[0950]

[0951] 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) and compound B29 (16.6 g, 31.6 mmol) synthesized by the method of Preparation Example 43, 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 added to 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 completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 714 (7'-(3-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)dibenzo[b,d]thiophen-1-yl)spiro[cyclohexane-1,9'-fluorene]-1'-carbonitrile) (21.1 g, 25.6 mmol, yield 81%).

[0952] Mass: [(M+H) + ] : 749

[0953]

[0954] [Synthesis Example 102]: Synthesis of Compound 761

[0955]

[0956] 4-(1'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclohexane-1,9'-fluoren]-5'-yl)pyridine (15.0 g, 31.6 mmol) and compound B30 (16.6 g, 31.6 mmol) synthesized by the method of Preparation Example 44, 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 added to 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 completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 761 (2,3-diphenyl-5-(2-(1-(4'-(pyridin-4-yl)spiro[cyclohexane-1,9'-fluoren]-8'-yl)dibenzo[b,d]thiophen-3-yl)phenyl)pyrazine)(21.1 g, 25.6 mmol, yield 81%).

[0957] Mass: [(M+H) + ] : 801

[0958]

[0959] [Synthesis Example 103]: Synthesis of Compound 763

[0960]

[0961] 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) and 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (15.1 g, 38.9 mmol) mmol), and Pd(PPh3)4 (1.3 g, 1.2 mmol) and K2CO 3(16.1 g, 116.8 mmol) was added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 763(2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-carbonitrile)(17.4 g, 30.8 mmol, yield 79%).

[0962] Mass: [(M+H) + ] :568

[0963]

[0964] [Examples and Comparative Examples] - 1

[0965] [Examples 1 to 103 and Comparative Examples 1 to 7]: Fabrication of blue organic electroluminescent devices

[0966] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0967] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0968] An organic electroluminescent device was manufactured 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 cathode on the ITO transparent electrode (anode) 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 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing Compound D and Compound E in a weight ratio of 98:2 on the hole transport auxiliary layer to a thickness of 200 Å, the electron transport auxiliary layer was formed by depositing Compound F in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing an electron transport auxiliary layer material and Compound H in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. The structures of compounds A to H are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0969] Compound A Compound B Compound C Compound D Compound E Compound F Compound G Compound H

[0970] [Correction pursuant to Rule 91 dated 24.01.2025]

[0971] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 103 and Comparative Examples 1 to 7

[0972] For the organic electroluminescent devices manufactured in Examples 1 to 103 and Comparative Examples 1 to 7, the driving voltage, luminescence (EL) peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 3 below.

[0973] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 13.54538.7 Example 23.64548.5 Example 33.64538.6 Example 43.54528.8 Example 53.64518.6 Example 63.74548.4 Example 73.44538.7 Example 83.54558.4 Example 93.64528.5 Example 103.54538.8 Example 113.54568.6 Example 123.64538.5 Example 133.64538.8 Example 143.74558.6 Example 153.64548.6 Example 163.44538.7 Example 173.54558.5 Example 183.54528.5 Example 193.64538.8 Example 203.64568.5 Example 213.74538.4 Example 223.74538.7 Example 233.84538.6 Example 243.84538.6 Example 253.54538.8 Example 263.64538.5 Example 273.64538.5 Example 283.54538.7 Example 293.54538.5 Example 303.64548.4 Example 313.44538.8 Example 323.74548.4 Example 333.64558.3 ​​Example 343.54548.7 Example 353.54568.7 Example 363.64558.6 Example 373.64558.7 Example 383.74548.3 Example 393.64568.2 Example 403.74558.6 Example 413.74568.6 Example 423.64538.5 Example 433.64548.8 Example 443.64568.5 Example 453.74558.6 Example 463.64578.6 Example 473.84568.6 Example 483.64558.5 Example 493.74548.8 Example 503.84548.4 Example 513.74558.4 Example 523.64538.7 Example 533.64568.6 Example 543.84558.5 Example 553.64558.6 Example 563.64548.6 Example 573.74558.8 Example 583.54548.5 Example 593.64538.5 Example 603.64558.4 Example 613.54558.7 Example 623.74548.5 Example 633.64558.6 Example 643.54548.7 Example 653.74558.6 Example 663.74568.7 Embodiment 673.64558.8 Embodiment 683.84558.6 Embodiment 693.74548.5 Embodiment 703.64568.7 Embodiment 713.64558.6 Embodiment 723.74558.6 Embodiment 733.54548.7 Embodiment 743.74528.5 Embodiment 753.64558.4 Embodiment 763.34538.6 Embodiment 773.84558.5 Embodiment 783.74548.5 Embodiment 793.64548.7 Embodiment 803.74538.6 Embodiment 813.64558.6 Embodiment 823.84568.5 Example 833.84558.4 Example 843.84538.4 Example 853.54568.7 Example 863.64558.7 Example 873.64528.6 Example 883.64558.6 Example 893.64548.4 Example 903.74568.4 Example 913.44558.8 Example 923.54558.3 ​​Example 933.74568.4 Example 943.54548.2 Example 953.64558.2 Example 963.44568.3 Example 973.54568.4 Example 983.84558.3 ​​Example 993.84568.4 Example 1003.54558.7 Example 1013.64568.7 Example 1023.54558.2 Example 1033.54558.6 Comparative Example 14.24557.7 Comparative Example 24.44547.5 Comparative Example 34.44557.3 Comparative Example 44.24557.4 Comparative Example 54.34577.4 Comparative Example 64.44567.4 Comparative Example 74.14567.6.

[0974] Referring to Table 3 above, the blue organic electroluminescent devices manufactured in Examples 1 to 103 using the compounds according to the present invention as electron transport layer materials showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices manufactured in Comparative Examples 1 to 7 using compounds I to O as electron transport layer materials.

[0975] Specifically, the organic light-emitting compound according to the present invention used in the blue organic electroluminescent device of Examples 1 to 103 has a structure in which an azine moiety having excellent electron transport ability and stability is connected to a cyclohexylfluorene group to which a cyano group or a pyridine group is bonded to increase a dipole moment, so that the blue organic electroluminescent device of Comparative Example 1 and Comparative Example 7, which use a compound in which an azine moiety and a cyclohexylfluorene group are bonded and do not contain a cyano group or a pyridine group as an electron transport layer material, such as Compound I or Compound O, the blue organic electroluminescent device of Comparative Example 2, which use a compound in which a cyclohexylfluorene group is bonded to a cyano group and do not contain an azine moiety as an electron transport layer material, such as Compound J, the blue organic electroluminescent device of Comparative Example 2, which use a compound in which a cyclohexylfluorene group is bonded to a cyano group and contains an azine moiety, but the cyclohexylfluorene group is not bonded in an ortho position to the azine moiety, such as Compound K or Compound L, is used as an electron transport layer material. It was found that the blue organic electroluminescent devices of Comparative Examples 3 and 4, which were used as materials, and the blue organic electroluminescent devices of Comparative Examples 5 and 6, which used a compound in which a cyclohexylfluorene group is bonded to a cyano group or a pyridine group and an azine moiety, such as Compound M or Compound N, but the cyclohexylfluorene group is directly bonded to the azine moiety without a linker, in the electron transport layer, exhibited superior performance in terms of driving voltage and current efficiency.

[0976]

[0977] [Examples and Comparative Examples] - 2

[0978] [Examples 104 to 108 and Comparative Example 8]: Fabrication of a blue organic electroluminescent device

[0979] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0980] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0981] An organic electroluminescent device was manufactured 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 cathode on the ITO transparent electrode (anode) 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 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, 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 an electron transport auxiliary layer material in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing Compound G and Compound H in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. Compounds A to H are as shown in Table 1 above, and the electron transport auxiliary layer materials are shown in Table 4 below.

[0982] Electron transport auxiliary layer material Example 104 Compound 518 Example 105 Compound 635 Example 106 Compound 646 Example 107 Compound 714 Example 108 Compound 761 Comparative Example 8 Compound F

[0983] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 104 to 108 and Comparative Example 8

[0984] For the organic electroluminescent devices manufactured in Examples 104 to 108 and Comparative Example 8, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 5 below.

[0985] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 1044.04537.5 Example 1053.94557.7 Example 1063.84567.8 Example 1074.14537.6 Example 1084.04547.7 Comparative example 84.54567.0

[0986] Referring to Table 5 above, the blue organic electroluminescent devices manufactured in Examples 104 to 108 using the compound according to the present invention as an electron transport layer material showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device manufactured in Comparative Example 8 using compound F as an electron transport auxiliary layer material.

[0987]

[0988] While the embodiments of the present invention have been described above, those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical concept or essential features thereof. Therefore, the embodiments described above should be understood to be illustrative in all respects, not restrictive.

Claims

1. An organic luminescent compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, Either X1 or X4 is C-(L2) c -R2, and the rest are each independently N or CR, and at least two of X1 to X4 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, each of which may be unsubstituted or substituted, R1 and R2 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 a are arylamine groups, each of which may be unsubstituted or substituted, L1 to L3 are each independently a single bond, an arylene group having 6 to 60 carbon atoms or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, R3 and R4 are each 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, a to c are each independently integers from 0 to 5, d is an integer from 0 to 3, and e is an integer from 0 to 4, where d+e ≥ 1.

2. In paragraph 1, Either X1 or X4 is C-(L2) c -R2, and the rest are each independently N or CR, and at least two of X1 to X4 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 above R1 and R2 are each independently hydrogen, 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, 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, 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 arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms or a alkyl group having 6 to 30 carbon atoms. 30 arylamine groups, each of which is unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 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, 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, 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 alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms or a carbon atom It can be substituted with 6 to 30 arylamine groups, The above L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, The above R3 and R4 are each 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, The above a to c are each independently an integer from 0 to 2, The above d is an integer from 0 to 2, and e is an integer from 0 to 2, where d+e ≥ 1.

3. In paragraph 1, Among the above X1 to X4, one is C-(L2) c -R2, and the rest are each independently N or CH, and at least two of the above X1 to X4 are N, The above R1 and R2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, and each of them may be 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, 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, The above L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, The above R3 and R4 are each independently an aryl group having 6 to 30 carbon atoms substituted with a cyano group, a heteroaryl group containing nitrogen and having 2 to 30 carbon atoms, or a cyano group, The above a to c are each independently an integer from 0 to 2, An organic luminescent compound wherein d is an integer from 0 to 2, e is an integer from 0 to 2, and wherein d+e ≥ 1.

4. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by one selected from the following chemical formulas 2 to 9: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] In each of the chemical formulas 2 to 9 above, R1 and R2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, each of which may be 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, 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, L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, R3 and R4 are each independently an aryl group having 6 to 30 carbon atoms substituted with a cyano group, a heteroaryl group containing nitrogen and having 2 to 30 carbon atoms, or a cyano group, a to c are each independently integers from 0 to 2.

5. In paragraph 4, The above chemical formula 1 is an organic light-emitting compound represented by any one selected from the following chemical formulas 2 to 7: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] In each of the chemical formulas 2 to 7 above, R1 and R2 are each 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 may be 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, 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, R3 and R4 are each independently a phenyl group, a pyridyl group or a cyano group substituted with a cyano group, a to c are each independently integers from 0 to 2.

6. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound selected from compounds 001 to 774 below.

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

8. In paragraph 7, The above organic electroluminescent device comprises: an anode; a cathode; a light-emitting layer disposed between the cathode and the anode; and an electron transport region disposed between the cathode and the light-emitting layer. The above electron transport region is an organic electroluminescent device comprising the organic light emitting compound.

9. In paragraph 8, The above electron transport region includes at least one of an electron transport layer and an electron transport auxiliary layer, An organic electroluminescent device, wherein the organic light-emitting compound is included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

10. Use of an organic light-emitting compound according to any one of claims 1 to 6 in an organic electroluminescent device.

11. In paragraph 10, A use characterized in that the organic light-emitting compound is used as an electron transport material in the organic electroluminescent device.

Images