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.

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. 10-2023-0181557, filed December 14, 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]

[0006] 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.

[0007] 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.

[0008] 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.

[0009] 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.

[0010] Up to now, NPB, BCP, Alq3, etc., shown below, 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, (acac)Ir(btp)2, etc., shown below, 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), shown below, is being used as a phosphorescent host material.

[0011]

[0012] 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.

[0013] Therefore, the development of high-performance organic layer materials is required.

[0014] Prior art literature

[0015] Republic of Korea Patent Publication No. 10-2019-0093314

[0016]

[0017] The present invention aims to provide a novel organic luminescent compound having excellent heat resistance, carrier transport ability, luminescence ability, etc., which can be used as an organic layer material of an organic electroluminescent device, specifically, a luminescent layer material, a life-span improving layer material, a hole transport auxiliary layer material, or an electron transport layer material, and a use thereof.

[0018] In addition, the present invention aims to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan by including the novel organic luminescent compound described above.

[0019]

[0020] 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.

[0021]

[0022] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0023] [Chemical Formula 1]

[0024]

[0025] In the above chemical formula 1,

[0026] X1 to X3 are identical or different from each other, and are each independently N or CR, provided that at least two of X1 to X3 are N,

[0027] R ,Ar1 and Ar2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, arylboron group having 6 to 60 carbon atoms, arylphosphinyl group having 6 to 60 carbon atoms, An arylamine group, an arylheteroarylamine group having 5 to 60 carbon atoms, or a heteroarylamine group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0028] L1 and L2 are each independently a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 2 to 18 carbon atoms, each of which may be unsubstituted or substituted,

[0029] Dn means that n hydrogens are replaced by deuterium, where n is an integer greater than or equal to 0,

[0030] a to c are each independently integers from 0 to 2.

[0031] In addition, the present invention provides an organic electroluminescent device comprising the above-described organic luminescent compound.

[0032] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0033]

[0034] The organic light-emitting compound according to the present invention has excellent carrier transport ability, luminescence ability, and thermal stability, and thus has the advantage of being useful as a material for a high-efficiency, long-life electron transport layer and a hole transport auxiliary layer.

[0035] In addition, the organic electroluminescent device according to the present invention has the advantages of low driving voltage, high luminous efficiency, and high lifespan.

[0036]

[0037] 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.

[0038]

[0039] 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 together with the accompanying drawings. 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.

[0040] The terminology used herein is for the purpose of describing embodiments only and is not intended to limit the present invention. In this specification, the singular also includes the plural 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 mentioned components. Like reference numerals refer to like components throughout the specification, and "and / or" includes each and any combination of one or more of the mentioned components. Although "first", "second", etc. are used to describe various components, these components are not limited by these terms. These terms are only used to distinguish one component from another. Therefore, it should be understood that a first component mentioned below may also be a second component within the technical spirit of the present invention.

[0041] 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.

[0042] Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings.

[0043] 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.

[0044]

[0045] 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.

[0046] In the present invention, the term “alkenyl group” may mean an alkyl group containing one or two or more double bonds.

[0047] In the present invention, the term “alkynyl group” may mean an alkyl group containing one or two or more triple bonds.

[0048] 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, and a cyclooctyl group, but is not limited thereto.

[0049] In the present invention, the term "heterocycloalkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon having a ring structure containing at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom.

[0050] 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 chrysenyl 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.

[0051] 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 pyrimidinyl group, a pyrazinyl 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, a purinyl group, an indazolyl group, a quinolyl group, an isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group, acridinyl group, phenanthridinyl group, carbazolyl group, phenanthrolinyl group,Nitrogen-containing heteroaryl groups including a phenazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples include oxygen-containing heteroaryl groups including furyl group, pyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, and benzonaphthofuranyl group.

[0052] In the above heterocycloalkyl group and heteroaryl group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms refers to the total number of atoms as the sum of the numbers of carbon and non-carbon atoms forming the ring, and 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 heterocycloalkyl group and heteroaryl group may each have the number of nuclear atoms of 5 to 60, 5 to 30, or 5 to 20.

[0053] In the present invention, the term “alkyloxy group” may mean an alkyl group to which an oxygen radical is attached, and the term “aryloxy group” may mean an aryl group to which an oxygen radical is attached.

[0054] In the present invention, the term “alkylsilyl group” may mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with alkyl, and the term “arylsilyl group” may mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with aryl.

[0055] In the present invention, the term “alkylboron group” may mean a boron group substituted with alkyl, and the term “arylboron group” may mean a boron group substituted with aryl.

[0056] In the present invention, the term “arylphosphinyl group” may mean a phosphine group substituted with aryl, and includes not only mono- but also di-arylphosphinyl groups.

[0057] In the present invention, the term “arylamine group” may mean an amine group substituted with aryl, and includes not only mono- but also di-arylamine groups.

[0058] In the present invention, the term “arylheteroarylamine group” may mean an amine group in which an aryl group and a heteroaryl group are substituted on the N of the amine group.

[0059] In the present invention, the term "amine group" may be selected from the group consisting of -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, an N-biphenylfluorenylamine group, and the like.

[0060] In the present invention, the term “heteroarylamine group” may mean an amine group in which a heteroaryl group is substituted on the N of the amine group.

[0061] In the present invention, the term "arylene group" may be applied to the description of an aryl group, except that it is divalent.

[0062] In the present invention, the term "heteroarylene group" may be applied to the description of the heteroaryl group described above, except that it is divalent.

[0063] In the present invention, the term "substitution" may mean substitution with one or more substituents independently selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, and a cyano group, and when substitution is with multiple substituents, they may be the same or different from each other.

[0064]

[0065] Organic electroluminescent compounds

[0066] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0067] [Chemical Formula 1]

[0068]

[0069] In the above chemical formula 1,

[0070] X1 to X3 are identical or different from each other, and are each independently N or CR, provided that at least two of X1 to X3 are N,

[0071] R , Ar1 and Ar2 are hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, An arylboron group having 60 carbon atoms, an arylphosphinyl group having 6 to 60 carbon atoms, an arylamine group having 6 to 60 carbon atoms, an arylheteroarylamine group having 5 to 60 carbon atoms, a heteroarylamine group having 2 to 60 carbon atoms, or a heteroarylamine group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0072] L1 and L2 are each independently a single bond, an arylene group having 6 to 18 carbon atoms, a heteroarylene group having 2 to 18 carbon atoms, or a heteroarylene group having 5 to 18 nuclear atoms, each of which may be unsubstituted or substituted,

[0073] Dn means that n hydrogens are replaced by deuterium, where n is an integer greater than or equal to 0,

[0074] a to c are each independently integers from 0 to 2.

[0075] In one embodiment, when a is 0, L1 is not present and the cyclopentylfluorene group is It can mean that it is singly bonded to a moiety.

[0076] In one embodiment, when b is 0, L2 is not present and the cyclopentylfluorene group It can mean that it is singly bonded to a moiety.

[0077] In one embodiment, when c is 0, the cyclopentyl fluorene group or (L2) b This may mean that the cyano group (CN) is not substituted for the hydrogen present in .

[0078]

[0079] Specifically, R , At least one group among hydrogen atoms, halogen, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphinyl group, arylamine group, arylheteroarylamine group and heteroarylamine group which may be present in each of Ar1, Ar2, L1 and L2 may be independently unsubstituted or substituted with at least one substituent selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 5 to 20 nuclear atoms and a cyano group, and plural When substituted with a dog's substituents, they may be the same or different.

[0080] In one embodiment, all of X1 to X3 are N.

[0081] In one embodiment, two of X1 to X3 are N, one is CR, and R is hydrogen.

[0082] In one embodiment, L1 and L2 are each independently a direct bond, 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.

[0083] In one embodiment, L1 and L2 are each independently a direct bond, a phenylene group or a naphthylenyl group.

[0084] In one embodiment, Ar1 and Ar2 are each independently 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.

[0085] In one embodiment, Ar1 and Ar2 are each independently 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 with deuterium, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, or a nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms.

[0086] In one embodiment, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, or a dibenzofuranyl group, each of which may be unsubstituted or substituted with a deuterium group, a cyano group, a cyclopentyl group, a pyridyl group, or a pyrimidyl group.

[0087] In one implementation, a is 1, b is 1, and c is 0.

[0088] In one implementation, a is 1, b is 0, and c is 1.

[0089] In one implementation, a is 1, b is 0, and c is 2.

[0090] In one implementation, a is 0, b is 0, and c is 1.

[0091] In one implementation, a is 0, b is 1, and c is 0.

[0092] In one implementation, a is 0, b is 0, and c is 0.

[0093]

[0094] In one embodiment, the chemical formula 1 may be represented by any one of the following chemical formulas 2 and 3.

[0095] [Chemical Formula 2]

[0096]

[0097] [Chemical Formula 3]

[0098]

[0099] In the above chemical formulas 2 and 3,

[0100] Ar1 and Ar2 are as defined in chemical formula 1,

[0101] Ar3 is hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, An arylborone group, an arylphosphinyl group having 6 to 60 carbon atoms, an arylamine group having 6 to 60 carbon atoms, an arylheteroarylamine group having 5 to 60 carbon atoms, a heteroarylamine group having 2 to 60 carbon atoms, or a heteroarylamine group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0102] X1 to X3, and D n is as defined in chemical formula 1,

[0103] b and c are as defined in chemical formula 1,

[0104] d is an integer from 0 to 4,

[0105] e is an integer from 0 to 6.

[0106] Specifically, the above substitution may be performed by one or more groups selected from the group consisting of hydrogen atoms, halogens, cyano groups, nitro groups, alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, arylphosphinyl groups, arylamine groups, arylheteroarylamine groups and heteroarylamine groups that may be present in Ar3, which may be independently unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 5 to 20 nuclear atoms and a cyano group, and substituted with multiple substituents. In some cases, they may be identical or different.

[0107]

[0108] In one embodiment, Ar1 to Ar3 are each independently hydrogen, 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.

[0109] In one embodiment, Ar1 to Ar3 are each independently hydrogen, 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 with deuterium, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a nitrogen-containing heteroaryl group having 2 to 60 carbon atoms, or a nitrogen-containing heteroaryl group having 5 to 60 nuclear atoms.

[0110] In one embodiment, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, or a dibenzofuranyl group, each of which may be unsubstituted or substituted with a deuterium group, a cyano group, a cyclopentyl group, a pyridyl group, or a pyrimidyl group.

[0111]

[0112] In one embodiment, Ar3 is each independently hydrogen or an aryl group having 6 to 60 carbon atoms.

[0113] In one embodiment, Ar3 is each independently hydrogen or a phenyl group.

[0114] In one implementation, d is 0 or 1.

[0115] In one implementation, e is 0 or 1.

[0116]

[0117] In one embodiment, the chemical formula 1 may be represented by any one of the following chemical formulas 4 to 17.

[0118] [Chemical Formula 4]

[0119]

[0120] [Chemical Formula 5]

[0121]

[0122] [Chemical Formula 6]

[0123]

[0124] [Chemical Formula 7]

[0125]

[0126] [Chemical Formula 8]

[0127]

[0128] [Chemical Formula 9]

[0129]

[0130] [Chemical Formula 10]

[0131]

[0132] [Chemical Formula 11]

[0133]

[0134] [Chemical Formula 12]

[0135]

[0136] [Chemical Formula 13]

[0137]

[0138] [Chemical Formula 14]

[0139]

[0140] [Chemical Formula 15]

[0141]

[0142] [Chemical Formula 16]

[0143]

[0144] [Chemical Formula 17]

[0145]

[0146] In each of the above chemical formulas 4 to 17,

[0147] Ar1 to Ar 3, X1 to X3, Dn, d and e are as defined in the above chemical formula 2 or 3.

[0148] Therefore, Ar1 and Ar2 are each as defined in chemical formula 1,

[0149] Ar3 is each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, arylboron group having 6 to 60 carbon atoms, arylphosphinyl group having 6 to 60 carbon atoms, arylamine group having 6 to 60 carbon atoms, An arylheteroarylamine group having 5 to 60 carbon atoms or a heteroarylamine group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0150] X1 to X3, and D n is as defined in chemical formula 1,

[0151] d is an integer from 0 to 4,

[0152] e is an integer from 0 to 6.

[0153]

[0154] In one embodiment, Ar1, Ar2 and Ar3 may each independently be hydrogen and any one of the following formulae A-1 to A-12.

[0155] [Chemical Formula A-1]

[0156]

[0157] [Chemical Formula A-2]

[0158]

[0159] [Chemical Formula A-3]

[0160]

[0161] [Chemical Formula A-4]

[0162]

[0163] [Chemical Formula A-5]

[0164]

[0165] [Chemical Formula A-6]

[0166]

[0167] [Chemical Formula A-7]

[0168]

[0169] [Chemical Formula A-8]

[0170]

[0171] [Chemical Formula A-9]

[0172]

[0173] [Chemical Formula A-10]

[0174]

[0175] [Chemical Formula A-11]

[0176]

[0177] [Chemical Formula A-12]

[0178]

[0179] In the above chemical formulas A-1 to A-12,

[0180] * indicates a site that is bonded to the above chemical formula 1.

[0181]

[0182] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one selected from the following compounds.

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252] As a specific example, the compound represented by the above chemical formula 1 is the compound 1-1, 1-2, 1-3, 1-8, 1-13, 1-14, 1-15, 1-17, 1-25, 1-26, 1-27, 1-73, 1-74, 1-75, 1-99, 1-105, 1-109, 1-110, 1-127, 1-128, 1-129, 1-130, 2-1, 2-2, 2-3, 2-8, 2-13, 2-14, 2-15, 2-25, 2-26, 2-27, 2-37, 2-38, 2-39, 2-49, 2-61, 2-75, It can be any of 2-81, 2-95, 2-98, 2-101, 2-102, 2-103, 2-104, 2-108, and 2-112.

[0253] The novel organic light-emitting compound of the present invention forms a basic skeleton by additionally bonding one or more electron-withdrawing groups (EWGs) having excellent electron transport ability, nitrogen-containing heterocycles, such as azines such as triazine and pyrimidine, and sometimes a cyano group (-CN) to a core having an aliphatic ring group, for example, a cyclopentyl group in a pentagonal ring form, at the 9th position of fluorene.

[0254] These cyclopentyl fluorene cores can be substituted with chemically and physically stable cycloalkyl groups, thereby enhancing the stability of their molecular structures and contributing to high efficiency and long life. Accordingly, compared to structures in which alkyl or aryl groups are substituted at the 9-position of conventional fluorene, these cores exhibit superior structural and thermal stability, resulting in superior glass transition temperature (Tg).

[0255] In addition, it has a smaller molecular weight than cyclohexyl fluorene cores with similar structural stability, thus providing better processability.

[0256] In addition, the organic light-emitting compound according to the present invention has a triazine or pyrimidine group, which is a strong electron withdrawer, and thus has advantageous properties in electron injection and transfer, thereby increasing the electron transfer ability to the light-emitting layer and showing an excellent effect in improving the initial driving voltage of the device.

[0257] In addition, since the organic light-emitting compound according to the present invention has a high triplet energy (T1), it can suppress the diffusion (movement) of excitons generated in the light-emitting layer.

[0258] Accordingly, the number of excitons contributing to light emission within the light-emitting layer increases, thereby improving the light emission efficiency of the device, and enhancing the durability and stability of the device, thereby efficiently increasing the lifespan of the device. In addition, when the organic light-emitting compound according to the present invention is used, the device exhibits physical characteristics that enable low-voltage operation, thereby improving the lifespan.

[0259]

[0260] Organic electroluminescent devices

[0261] 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.

[0262] 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.

[0263]

[0264] anode

[0265] 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.

[0266] 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.

[0267] 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.

[0268]

[0269] cathode

[0270] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0271] 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.

[0272]

[0273] luminescent layer

[0274] 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.

[0275] 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.

[0276] 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.

[0277]

[0278] electron transport region

[0279] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0280] 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.

[0281] In one embodiment, the electron transport region includes at least one of an electron transport layer and an electron transport auxiliary layer, and the organic light-emitting compound may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0282] 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.

[0283]

[0284] electron transport layer

[0285] The above electron transport layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention has a basic skeleton in which a core having an aliphatic ring group, for example, a cyclopentyl group in the form of a pentagonal ring, is bonded to one or more electron-withdrawing groups (EWGs) having excellent electron transport ability, such as nitrogen-containing heterocycles, at the 9th position of fluorene, and in some cases, a cyano group is additionally bonded to further improve the electron transport ability, thereby effectively improving the initial driving voltage of the organic electroluminescent device and providing excellent thermal stability. In addition, an organic electroluminescent device using the organic light-emitting compound according to the present invention in the electron transport layer may have a low refractive index, high efficiency, and a long lifespan.

[0286] 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.

[0287] The electron transport region can be manufactured using conventional methods 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).

[0288]

[0289] electron transport auxiliary layer

[0290] 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.

[0291] The above electron transport auxiliary layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention has a basic skeleton in which a core adopting an aliphatic ring group, for example, a cyclopentyl group in the form of a pentagonal ring, at the 9th position of fluorene is bonded to one or more electron withdrawing groups (EWGs) having excellent electron transport ability, such as nitrogen-containing heterocycles, and in some cases, a cyano group is additionally bonded to further improve the electron transport ability, thereby effectively improving the initial driving voltage of the organic electroluminescent device and providing excellent thermal stability. In addition, an organic electroluminescent device using the organic light-emitting compound according to the present invention in the electron transport auxiliary layer may have a low refractive index, high efficiency, and a long lifespan.

[0292] 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.

[0293]

[0294] hole transport region

[0295] 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.

[0296] 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.

[0297] 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.

[0298] 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. Can be used alone or in combination of two or more

[0299] 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.

[0300] 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).

[0301]

[0302] hole transport auxiliary layer

[0303] 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.

[0304] 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.

[0305] 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.

[0306]

[0307] capping layer

[0308] 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.

[0309] 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-naphthyl)-N-phenyl-amino] 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).

[0310] 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.

[0311] 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.

[0312]

[0313] 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.

[0314] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0315] 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.

[0316] 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.

[0317]

[0318] 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.

[0319]

[0320] [Preparation]

[0321] [Preparation Example 1] Synthesis of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine

[0322]

[0323] 2-chloro-4,6-diphenyl-1,3,5-triazine (21.4 g, 80.0 mmol), (2-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and heated and stirred under reflux for 7 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and dichloromethane (DCM) was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (21.5 g, 62.4 mmol, yield 78%).

[0324] 1 H NMR: δ 8.75 (dd, 4H), 8.18-8.14 (m, 1H), 7.65-7.54 (m, 7H), 7.51-7.41 (m, 2H)

[0325] Mass [(M+H) + ]: 344.12

[0326]

[0327] [Preparation Example 2] Synthesis of 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine

[0328]

[0329] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (25.4 g, 80.0 mmol), (2-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and the mixture was heated and stirred under reflux for 8 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain the compound 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (22.9 g, 58.2 mmol, yield 73%).

[0330] 1 H NMR: δ 9.29 (s, 1H), 8.81-8.75 (m, 3H), 8.22-8.15 (m, 1H), 8.10-8.04 (m, 1H), 7.99 (d, 1H), 7.91 (d, 1H), 7.65-7.52 (m, 6H), 7.52-7.44 (m, 2H)

[0331] Mass [(M+H) + ]: 394.02

[0332]

[0333] [Preparation Example 3] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine

[0334]

[0335] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (27.5 g, 80.0 mmol), (2-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and the mixture was heated and stirred under reflux for 7 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (24.7 g, 58.8 mmol, yield 74%).

[0336] 1 H NMR: δ 8.82 (d, 2H), 8.76 (dd, 2H), 8.19-8.16 (m, 1H), 7.82-7.77 (m, 2H), 7.73-7.68 (m, 2H), 7.65-7.55 (m, 4H), 7.53-7.44 (m, 4H), 7.44-7.39 (m, 1H)

[0337] Mass: [(M+H) + ]: 420.14

[0338]

[0339] [Preparation Example 4] Synthesis of 2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine

[0340]

[0341] 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (60.0 g, 167.7 mmol), (2-chlorophenyl)boronic acid (31.5 g, 201.2 mmol), Pd(PPh3)4 (5.8 g, 5.0 mmol), and K2CO3 (46.4 g, 335.4 mmol) were added to 670 mL of 1,4-dioxane and 170 mL of H2O, and the mixture was heated and stirred under reflux for 3 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain the compound 2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (32.8 g, 75.6 mmol, yield 45%).

[0342] 1 H NMR: δ 8.85 (d, 2H), 8.75 (d, 1H), 8.31-8.25 (m, 1H), 8.18 (d, 1H), 8.01 (d, 1H), 7.76 (d, 1H), 7.67-7.56 (m, 4H), 7.56-7.45 (m, 4H), 7.40 (t, 1H)

[0343] Mass [(M+H) + ]: 434.12

[0344]

[0345] [Preparation Example 5] Synthesis of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine

[0346]

[0347] 2-chloro-4,6-diphenyl-1,3,5-triazine (26.8 g, 100.0 mmol), (3-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (25.9 g, 75.2 mmol, yield 75%).

[0348] 1 H NMR: δ 8.78-8.74 (m, 5H), 8.66 (d, 1H), 7.65-7.47 (m, 8H)

[0349] Mass [(M+H) + ] : 344.08

[0350]

[0351] [Preparation Example 6] Synthesis of 2-(3-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine

[0352]

[0353] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (31.8 g, 100.0 mmol), (3-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and the mixture was heated and stirred under reflux for 8 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain the compound 2-(3-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (26.7 g, 67.9 mmol, yield 68%).

[0354] 1 H NMR: δ 9.26 (s, 1H), 8.78-8.65 (m, 4H), 8.22-8.15 (m, 1H), 8.10-8.04 (m, 1H), 7.99 (d, 1H), 7.91 (d, 1H), 7.64-7.52 (m, 5H), 7.51-7.44 (m, 2H)

[0355] Mass [(M+H) + ]: 394.10

[0356]

[0357] [Preparation Example 7] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine

[0358]

[0359] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (27.5 g, 80.0 mmol), (3-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and the mixture was heated and stirred under reflux for 7 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (25.6 g, 61.0 mmol, yield 76%).

[0360] 1 H NMR: δ 8.88-8.64 (m, 6H), 7.85-7.67 (m, 4H), 7.67-7.38 (m, 8H)

[0361] Mass [(M+H) + ] : 420.12

[0362]

[0363]

[0364] [Preparation Example 8] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine

[0365]

[0366] 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (27.5 g, 80.0 mmol), (3-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and the mixture was heated and stirred under reflux for 8 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (25.3 g, 60.2 mmol, yield 75%).

[0367] 1 H NMR: δ 8.40-8.34 (m, 3H), 8.22-8.15 (m, 2H), 7.65-7.45 (m, 7H), 7.40-7.28 (m, 6H)

[0368] Mass [(M+H) + ] : 420.11

[0369]

[0370] [Preparation Example 9] Synthesis of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine

[0371]

[0372] 2-chloro-4,6-diphenyl-1,3,5-triazine (21.4 g, 80.0 mmol), (4-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and heated and stirred under reflux for 5 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (21.6 g, 62.7 mmol, yield 78%).

[0373] 1 H NMR: δ 8.75-8.63 (m, 6H), 7.58-7.49 (m, 8H)

[0374] Mass [(M+H) + ] : 344.09

[0375]

[0376] [Preparation Example 10] Synthesis of 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine

[0377]

[0378] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (25.4 g, 80.0 mmol), (4-chlorophenyl)boronic acid (15.0 g, 96.0 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol), and K2CO3 (22.1 g, 160.0 mmol) were added to 320 mL of 1,4-dioxane and 80 mL of H2O, and the mixture was heated and stirred under reflux for 7 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain the compound 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.7 g, 60.1 mmol, yield 75%).

[0379] 1 H NMR: δ 9.28 (s, 1H), 8.79-8.63 (m, 5H), 8.11-8.05 (m, 1H), 8.00 (d, 1H), 7.93 (d, 1H), 7.65-7.47 (m, 7H)

[0380] Mass [(M+H) + ] : 394.12

[0381]

[0382] [Preparation Example 11] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine

[0383]

[0384] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (30.9 g, 90.0 mmol), (4-chlorophenyl)boronic acid (16.9 g, 108.0 mmol), Pd(PPh3)4 (3.1 g, 2.7 mmol), and K2CO3 (24.9 g, 180.0 mmol) were added to 360 mL of 1,4-dioxane and 90 mL of H2O, and the mixture was heated and stirred under reflux for 7 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (28.3 g, 67.3 mmol, yield 75%).

[0385] 1 H NMR: δ 8.89-8.63 (m, 6H), 7,87-7.66 (m, 4H), 7.66-7.39 (m, 8H)

[0386] Mass [(M+H) + ] : 420.14

[0387]

[0388] [Preparation Example 12] Synthesis of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine

[0389]

[0390] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (34.3 g, 100.0 mmol), (2-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (29.0 g, 69.2 mmol, yield 69%).

[0391] 1 H NMR: δ 8.69 (d, 2H), 8.36 (d, 2H), 8.05 (s, 1H), 7.89-7.81 (m, 1H), 7.78 (d, 2H), 7.68 (d, 2H), 7.58-7.34 (m, 9H).

[0392] Mass [(M+H) + ] : 419.12

[0393]

[0394] [Preparation Example 13] Synthesis of 4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine

[0395]

[0396] 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (34.3 g, 100.0 mmol), (2-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine (30.7 g, 73.4 mmol, yield 73%).

[0397] 1 H NMR: δ 8.28-8.24 (m, 4H), 8.07 (s, 1H), 8.05-8.00 (m, 1H), 7.61-7.49 (m, 8H), 7.48-7.38 (m, 5H)

[0398] Mass [(M+H) + ] : 419.11

[0399]

[0400] [Preparation Example 14] Synthesis of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine

[0401]

[0402] 2-chloro-4,6-diphenylpyrimidine (26.7 g, 100.0 mmol), (3-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (25.4 g, 74.2 mmol, yield 74%).

[0403] 1 H NMR: δ 8.70 (d, 1H), 8.65-8.61 (m, 1H), 8.32-8.27 (m, 4H), 8.05 (s, 1H), 7.61-7.54 (m, 6H), 7.51-7.46 (m, 2H)

[0404] Mass [(M+H) + ] : 343.10

[0405]

[0406] [Preparation Example 15] Synthesis of 2-(4-chlorophenyl)-4,6-diphenylpyrimidine

[0407]

[0408] 2-chloro-4,6-diphenylpyrimidine (26.7 g, 100.0 mmol), (4-chlorophenyl)boronic acid (18.8 g, 120.0 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (27.6 g, 200.0 mmol) were added to 400 mL of 1,4-dioxane and 100 mL of H2O, and the mixture was heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(4-chlorophenyl)-4,6-diphenylpyrimidine (24.1 g, 70.2 mmol, yield 70%).

[0409] 1 H NMR: δ 8.68 (d, 2H), 8.32-8.24 (m, 4H), 8.02 (s, 1H), 7.60-7.54 (m, 6H), 7.51 (d, 2H)

[0410] Mass [(M+H) + ] : 343.10

[0411]

[0412] [Preparation Example 16] Synthesis of 2-(3-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine

[0413]

[0414] 2-chloro-4,6-diphenyl-1,3,5-triazine (40.2 g, 150.0 mmol), (3-chloro-[1,1'-biphenyl]-2-yl)boronic acid (41.8 g, 180.0 mmol), Pd(PPh3)4 (5.2 g, 4.5 mmol), and K2CO3 (41.5 g, 300.0 mmol) were added to 600 mL of 1,4-dioxane and 150 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(3-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (27.6 g, 65.7 mmol, yield 44%).

[0415] 1 H NMR: δ 8.31 (d, 4H), 7.57-7.51 (m, 3H), 7.47-7.41 (m, 3H), 7.33-7.32 (m, 3H), 7.28-7.22 (m, 5H)

[0416] Mass [(M+H) + ] : 420.10

[0417]

[0418] [Preparation Example 17] Synthesis of 2-(4-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine

[0419]

[0420] 2-chloro-4,6-diphenyl-1,3,5-triazine (40.2 g, 150.0 mmol), (4-chloro-[1,1'-biphenyl]-2-yl)boronic acid (41.8 g, 180.0 mmol), Pd(PPh3)4 (5.2 g, 4.5 mmol), and K2CO3 (41.5 g, 300.0 mmol) were added to 600 mL of 1,4-dioxane and 150 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated and purified by column chromatography to obtain compound 2-(4-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (31.9 g, 75.9 mmol, yield 51%).

[0421] 1 H NMR: δ 8.31 (d, 4H), 8.08-8.05 (m, 1H), 7.58-7.53 (m, 3H), 7.46-7.32 (m, 6H), 7.28-7.22 (m, 4H)

[0422] Mass [(M+H) + ] : 420.08

[0423]

[0424] [Synthesis example]

[0425] [Synthesis Example 1] Synthesis of Compound 1-1

[0426]

[0427] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 58.2 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 69.8 mmol), Pd(OAc)2 (653 mg, 2.9 mmol), XPhos (2.8 g, 5.8 mmol), and K2CO3 (16.1 g, 116.4 mmol) were added to 180 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 7'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (23.7 g, 43.0 mmol, yield 74%).

[0428] Mass [(M+H) + ] : 553.24

[0429]

[0430] [Synthesis Example 2] Synthesis of Compound 1-2

[0431]

[0432] 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (22.9 g, 58.2 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 69.8 mmol), Pd(OAc)2 (653 mg, 2.9 mmol), XPhos (2.8 g, 5.8 mmol), and K2CO3 (16.1 g, 116.4 mmol) were added to 180 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 7'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (28.6 g, 47.5 mmol, yield 82%).

[0433] Mass [(M+H) + ] : 603.25

[0434]

[0435] [Synthesis Example 3] Synthesis of Compound 1-3

[0436]

[0437] 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (18.5 g, 44.1 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (19.6 g, 52.9 mmol), Pd(OAc)2 (495 mg, 2.2 mmol), XPhos (2.1 g, 4.4 mmol), and K2CO3 (12.2 g, 88.2 mmol) were added to 140 mL of toluene, 40 mL of EtOH, and 40 mL of H2O, and heated and stirred under reflux for 14 h. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (18.4 g, 29.2 mmol, yield 66%).

[0438] Mass [(M+H) + ] : 629.28

[0439]

[0440] [Synthesis Example 4] Synthesis of Compound 1-8

[0441]

[0442] 2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (26.0 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (26.7 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 7'-(2-(4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (29.2 g, 45.5 mmol, yield 76%).

[0443] Mass [(M+H) + ] : 643.24

[0444]

[0445] [Synthesis Example 5] Synthesis of Compound 1-13

[0446]

[0447] 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (26.7 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 7'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.2 g, 45.5 mmol, yield 76%).

[0448] Mass [(M+H) + ] : 553.24

[0449]

[0450] [Synthesis Example 6] Synthesis of Compound 1-14

[0451]

[0452] 2-(3-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 7'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (26.3 g, 43.7 mmol, yield 73%).

[0453] Mass [(M+H) + ] : 603.28

[0454]

[0455] [Synthesis Example 7] Synthesis of Compound 1-15

[0456]

[0457] 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2'-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (26.2 g, 41.6 mmol, yield 69%).

[0458] Mass [(M+H) + ] : 629.28

[0459]

[0460] [Synthesis Example 8] Synthesis of Compound 1-17

[0461]

[0462] 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2'-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (25.0 g, 39.7 mmol, yield 66%).

[0463] Mass [(M+H) + ] : 629.26

[0464]

[0465] [Synthesis Example 9] Synthesis of Compound 1-25

[0466]

[0467] 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 7'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (23.7 g, 42.9 mmol, yield 72%).

[0468] Mass [(M+H) + ] : 553.25

[0469]

[0470] [Synthesis Example 10] Synthesis of Compound 1-26

[0471]

[0472] 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 7'-(4-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (28.0 g, 46.4 mmol, yield 77%).

[0473] Mass [(M+H) + ] : 603.25

[0474]

[0475] [Synthesis Example 11] Synthesis of Compound 1-27

[0476]

[0477] 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 2'-(4-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (25.6 g, 40.7 mmol, yield 68%).

[0478] Mass [(M+H) + ] : 629.30

[0479]

[0480] [Synthesis Example 12] Synthesis of Compound 1-73

[0481]

[0482] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (26.7 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 2'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (25.5 g, 46.1 mmol, yield 77%).

[0483] Mass [(M+H) + ] : 553.33

[0484]

[0485] [Synthesis Example 13] Synthesis of Compound 1-74

[0486]

[0487] 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (26.7 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (29.9 g, 49.6 mmol, yield 83%).

[0488] Mass [(M+H) + ] : 603.28

[0489]

[0490] [Synthesis Example 14] Synthesis of Compound 1-75

[0491]

[0492] 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (26.7 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-6'-carbonitrile (27.2 g, 43.3 mmol, yield 72%).

[0493] Mass [(M+H) + ] : 629.25

[0494]

[0495] [Synthesis Example 15] Synthesis of Compound 1-99

[0496]

[0497] 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (25.1 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2'-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (27.8 g, 44.3 mmol, yield 74%).

[0498] Mass [(M+H) + ] : 628.30

[0499]

[0500] [Synthesis Example 16] Synthesis of Compound 1-105

[0501]

[0502] 4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine (25.1 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-7'-carbonitrile (26.5 g, 42.2 mmol, yield 70%).

[0503] Mass [(M+H) + ] : 628.26

[0504]

[0505] [Synthesis Example 17] Synthesis of Compound 1-109

[0506]

[0507] 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (20.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 7'-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (21.6 g, 39.1 mmol, yield 65%).

[0508] Mass [(M+H) + ] : 552.24

[0509]

[0510] [Synthesis Example 18] Synthesis of Compound 1-110

[0511]

[0512] 2-(4-chlorophenyl)-4,6-diphenylpyrimidine (20.6 g, 60.0 mmol) and 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (25.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 7'-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-carbonitrile (24.4 g, 44.2 mmol, yield 74%).

[0513] Mass [(M+H) + ] : 552.25

[0514]

[0515] [Synthesis Example 19] Synthesis of Compound 1-127

[0516]

[0517] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluoren]-8'-yl)benzonitrile (32.2 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 4-(2'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluoren]-8'-yl)benzonitrile (27.7 g, 44.0 mmol, yield 73%).

[0518] Mass [(M+H) + ] : 629.26

[0519]

[0520] [Synthesis Example 20] Synthesis of Compound 1-128

[0521]

[0522] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluoren]-7'-yl)benzonitrile (32.2 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 4-(2'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluoren]-7'-yl)benzonitrile (28.5 g, 45.4 mmol, yield 76%).

[0523] Mass [(M+H) + ] : 629.28

[0524]

[0525] [Synthesis Example 21] Synthesis of Compound 1-129

[0526]

[0527] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluoren]-6'-yl)benzonitrile (32.2 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 4-(2'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluoren]-6'-yl)benzonitrile (27.1 g, 43.1 mmol, yield 72%).

[0528] Mass [(M+H) + ] : 629.27

[0529]

[0530] [Synthesis Example 22] Synthesis of Compound 1-130

[0531]

[0532] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluoren]-5'-yl)benzonitrile (32.2 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 4-(2'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)spiro[cyclopentane-1,9'-fluoren]-5'-yl)benzonitrile (25.2 g, 40.1 mmol, yield 67%).

[0533] Mass [(M+H) + ] : 629.24

[0534]

[0535] [Synthesis Example 23] Synthesis of Compound 2-1

[0536]

[0537] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (23.0 g, 43.7 mmol, yield 73%).

[0538] Mass [(M+H) + ] : 528.20

[0539]

[0540] [Synthesis Example 24] Synthesis of Compound 2-2

[0541]

[0542] 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2-(naphthalen-2-yl)-4-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (26.9 g, 46.6 mmol, yield 78%).

[0543] Mass [(M+H) + ] : 578.26

[0544]

[0545] [Synthesis Example 25] Synthesis of Compound 2-3

[0546]

[0547] 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (25.4 g, 42.1 mmol, yield 70%).

[0548] Mass [(M+H) + ] : 604.29

[0549]

[0550] [Synthesis Example 26] Synthesis of Compound 2-8

[0551]

[0552] 2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (26.0 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2-(dibenzo[b,d]furan-4-yl)-4-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (26.6 g, 43.1 mmol, yield 72%).

[0553] Mass [(M+H) + ] : 618.25

[0554]

[0555] [Synthesis Example 27] Synthesis of Compound 2-13

[0556]

[0557] 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(3-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (24.2 g, 45.9 mmol, yield 77%).

[0558] Mass [(M+H) + ] : 528.24

[0559]

[0560] [Synthesis Example 28] Synthesis of Compound 2-14

[0561]

[0562] 2-(3-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2-(naphthalen-2-yl)-4-phenyl-6-(3-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (25.9 g, 44.8 mmol, yield 75%).

[0563] Mass [(M+H) + ] : 578.25

[0564]

[0565] [Synthesis Example 29] Synthesis of Compound 2-15

[0566]

[0567] 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (26.2 g, 43.4 mmol, yield 72%).

[0568] Mass [(M+H) + ] : 604.26

[0569]

[0570] [Synthesis Example 30] Synthesis of Compound 2-25

[0571]

[0572] 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(4-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (22.3 g, 42.3 mmol, yield 71%).

[0573] Mass [(M+H) + ] : 528.25

[0574]

[0575] [Synthesis Example 31] Synthesis of Compound 2-26

[0576]

[0577] 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2-(naphthalen-2-yl)-4-phenyl-6-(4-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (27.1 g, 47.0 mmol, yield 78%).

[0578] Mass [(M+H) + ] : 578.25

[0579]

[0580] [Synthesis Example 32] Synthesis of Compound 2-27

[0581]

[0582] 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(4-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)-1,3,5-triazine (24.9 g, 41.3 mmol, yield 69%).

[0583] Mass [(M+H) + ] : 604.27

[0584]

[0585] [Synthesis Example 33] Synthesis of Compound 2-37

[0586]

[0587] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)phenyl)-1,3,5-triazine (24.6 g, 46.7 mmol, yield 78%).

[0588] Mass [(M+H) + ] : 528.24

[0589]

[0590] [Synthesis Example 34] Synthesis of Compound 2-38

[0591]

[0592] 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (23.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2-(naphthalen-2-yl)-4-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)phenyl)-1,3,5-triazine (26.6 g, 46.0 mmol, yield 77%).

[0593] Mass [(M+H) + ] : 578.25

[0594]

[0595] [Synthesis Example 35] Synthesis of Compound 2-39

[0596]

[0597] 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain compound 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)phenyl)-1,3,5-triazine (26.5 g, 43.9 mmol, yield 73%).

[0598] Mass [(M+H) + ] : 604.28

[0599]

[0600] [Synthesis Example 36] Synthesis of Compound 2-49

[0601]

[0602] 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(3-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)phenyl)-1,3,5-triazine (23.6 g, 44.7 mmol, yield 75%).

[0603] Mass [(M+H) + ] : 528.24

[0604]

[0605] [Synthesis Example 37] Synthesis of Compound 2-61

[0606]

[0607] 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(4-(spiro[cyclopentane-1,9'-fluoren]-3'-yl)phenyl)-1,3,5-triazine (23.0 g, 43.5 mmol, yield 73%).

[0608] Mass [(M+H) + ] : 528.24

[0609]

[0610] [Synthesis Example 38] Synthesis of Compound 2-75

[0611]

[0612] 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (25.1 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)pyrimidine (26.5 g, 44.0 mmol, yield 73%).

[0613] Mass [(M+H) + ] : 602.37

[0614]

[0615] [Synthesis Example 39] Synthesis of Compound 2-81

[0616]

[0617] 4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine (25.1 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 4-([1,1'-biphenyl]-4-yl)-6-phenyl-2-(2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)phenyl)pyrimidine (26.2 g, 43.4 mmol, yield 72%).

[0618] Mass [(M+H) + ] : 602.36

[0619]

[0620] [Synthesis Example 40] Synthesis of Compound 2-95

[0621]

[0622] 2-(3-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain the compound 2,4-diphenyl-6-(3-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (23.9 g, 39.7 mmol, yield 66%).

[0623] Mass [(M+H) + ] : 604.27

[0624]

[0625] [Synthesis Example 41] Synthesis of Compound 2-98

[0626]

[0627] 2-(4-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (25.2 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-1,3,2-dioxaborolane (24.9 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain the compound 2,4-diphenyl-6-(4-(spiro[cyclopentane-1,9'-fluoren]-2'-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (26.7 g, 44.2 mmol, yield 74%).

[0628] Mass [(M+H) + ] : 604.27

[0629]

[0630] [Synthesis Example 42] Synthesis of Compound 2-101

[0631]

[0632] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(1'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(1'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (27.4 g, 45.3 mmol, yield 76%).

[0633] Mass [(M+H) + ] : 604.26

[0634]

[0635] [Synthesis Example 43] Synthesis of Compound 2-102

[0636]

[0637] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(2'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(2'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (25.1 g, 41.5 mmol, yield 69%).

[0638] Mass [(M+H) + ] : 604.28

[0639]

[0640] [Synthesis Example 44] Synthesis of Compound 2-103

[0641]

[0642] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(3'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(3'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (27.1 g, 44.9 mmol, yield 75%).

[0643] Mass [(M+H) + ] : 604.27

[0644]

[0645] [Synthesis Example 45] Synthesis of Compound 2-104

[0646]

[0647] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(2-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (26.6 g, 44.0 mmol, yield 73%).

[0648] Mass [(M+H) + ] : 604.27

[0649]

[0650] [Synthesis Example 46] Synthesis of Compound 2-108

[0651]

[0652] 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(3-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (25.5 g, 42.3 mmol, yield 71%).

[0653] Mass [(M+H) + ] : 604.30

[0654]

[0655] [Synthesis Example 47] Synthesis of Compound 2-112

[0656]

[0657] 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.6 g, 60.0 mmol) and 4,4,5,5-tetramethyl-2-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)-1,3,2-dioxaborolane (30.4 g, 72.0 mmol), Pd(OAc)2 (674 mg, 3.0 mmol), XPhos (2.9 g, 6.0 mmol), and K2CO3 (16.6 g, 120.0 mmol) were added to 190 mL of toluene, 55 mL of EtOH, and 55 mL of H2O, and heated and stirred under reflux for 15 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and DCM was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,4-diphenyl-6-(4-(4'-phenylspiro[cyclopentane-1,9'-fluoren]-7'-yl)phenyl)-1,3,5-triazine (27.2 g, 45.1 mmol, yield 75%).

[0658] Mass [(M+H) + ] : 604.28

[0659]

[0660] [Examples and Comparative Examples]

[0661] Examples 1 to 26 and Comparative Examples 1 to 6: Fabrication of blue organic electroluminescent devices (electron transport layer)

[0662] After the compound synthesized according to the synthesis example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0663] 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 transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0664] On the ITO transparent electrode (anode) prepared as above, an organic electroluminescent device was manufactured by stacking a hole injection layer (HI + 2% HAT-CN6 (10 nm)) / hole transport layer (HI (140 nm)) / hole transport auxiliary layer (EB (5 nm)) / emission layer (BH + 2% BD (20 nm)) / electron transport auxiliary layer (ET-2 (5 nm)) / electron transport layer (electron transport layer material of Table 2 + Liq (1:1) (30 nm)) / electron injection layer (LiF (1 nm)) / cathode (Al (100 nm)) in that order.

[0665] Specifically, the hole injection layer was formed by depositing 98 wt% HI and 2 wt% HAT-CN6 to a thickness of 10 nm on the anode, the hole transport layer was formed by depositing HI to a thickness of 140 nm on the hole injection layer, the hole transport auxiliary layer was formed by depositing EB to a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by depositing 98 wt% BH and 2 wt% BD to a thickness of 20 nm on the hole transport auxiliary layer, the electron transport auxiliary layer was formed by depositing ET-2 to a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by depositing 30 nm of the electron transport layer materials and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer, the electron injection layer was formed by depositing LiF to a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al to a thickness of 100 nm on the electron injection layer. Here, the structures of the compounds HI, HAT-CN6, EB, BH, BD, ET-2, and Liq are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0666] Compound HI Compound HAT-CN6 Compound EB Compound BH Compound BD Compound Liq Compound ET-2

[0667] Sample electron transport layer material Example 1 Compound 1-1 Example 2 Compound 1-2 Example 3 Compound 1-3 Example 4 Compound 1-8 Example 5 Compound 1-13 Example 6 Compound 1-14 Example 7 Compound 1-15 Example 8 Compound 1-17 Example 9 Compound 1-25 Example 10 Compound 1-26 Example 11 Compound 1-27 Example 12 Compound 1-73 Example 13 Compound 1-74 Example 14 Compound 1-75 Example 15 Compound 1-99 Example 16 Compound 1-105 Example 17 Compound 1-109 Example 18 Compound 1-110 Example 19 Compound 1-127 Example 20 Compound 1-128 Example 21 Compound 1-129 Example 22 Compound 1-130 Example 23 Compound 2-1 Example 24 Compound 2-2 Example 25 Compound 2-3 Example 26 Compound 2-8 Comparative Example 1Alq3 Comparative Example 2E-1 Comparative Example 3E-2 Comparative Example 4E-3 Comparative Example 5E-4 Comparative Example 6E-5

[0668]

[0669] Evaluation Example 1

[0670] For the organic electroluminescent devices manufactured in Examples 1 to 26 and Comparative Examples 1 to 6, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 3 below.

[0671] Sample Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 13.24558.0 Example 23.24548.1 Example 33.04548.4 Example 43.34558.3 ​​Example 53.54537.9 Example 63.44558.0 Example 73.24538.1 Example 83.14548.5 Example 93.44557.9 Example 103.34548.1 Example 113.24548.2 Example 123.34557.9 Example 133.34558.0 Example 143.24548.2 Example 153.44558.0 Example 163.34558.0 Example 173.54567.9 Example 183.44548.0 Example 193.44558.0 Example 203.34558.1 Example 213.54557.9 Example 223.34557.9 Example 233.54557.7 Example 243.44557.7 Example 253.44547.9 Example 263.54557.9 Comparative Example 14.64575.6 Comparative Example 24.84596.6 Comparative Example 34.54567.0 Comparative Example 43.94557.5 Comparative Example 53.64547.4 Comparative Example 63.64557.3

[0672] From Table 3 above, it can be confirmed that the organic light-emitting devices manufactured in Examples 1 to 26 are superior to the driving voltage, light emission peak, and current efficiency of the organic light-emitting devices manufactured in Comparative Examples 1 to 6, respectively.

[0673]

[0674] Examples 27 to 55 and Comparative Examples 7 to 12: Fabrication of blue organic electroluminescent devices (electron transport auxiliary layer)

[0675] After the compound synthesized in the above synthesis example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0676] 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 transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0677] On the ITO transparent electrode (anode) prepared as described above, an organic electroluminescent device was manufactured by stacking a hole injection layer (HI + 2% HAT-CN6 (10 nm)) / hole transport layer (HI (140 nm)) / hole transport auxiliary layer (EB (5 nm)) / emission layer (BH + 2% BD (20 nm)) / electron transport auxiliary layer (electron transport auxiliary layer material of Table 5 (5 nm)) / electron transport layer (ET-1 + Liq (1:1) (30 nm)) / electron injection layer (LiF (1 nm)) / cathode (Al (100 nm)) in that order.

[0678] Specifically, the hole injection layer was formed by depositing 98 wt% HI and 2 wt% HAT-CN6 to a thickness of 10 nm on the anode, the hole transport layer was formed by depositing HI to a thickness of 140 nm on the hole injection layer, the hole transport auxiliary layer was formed by depositing EB to a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by depositing 98 wt% BH and 2 wt% BD to a thickness of 20 nm on the hole transport auxiliary layer, the electron transport auxiliary layer was formed by depositing the electron transport auxiliary layer material of Table 5 to a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by depositing ET-1 and Liq at a weight ratio of 1:1 to a thickness of 30 nm on the electron transport auxiliary layer, the electron injection layer was formed by depositing LiF to a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al to a thickness of 100 nm on the electron injection layer. However, Comparative Example 7 did not form an electron transport auxiliary layer. Here, the structures of the compounds HI, HAT-CN6, EB, BH, BD, and Liq are as shown in Table 1 above, ET-1 is shown in Table 4 below, and the electron transport auxiliary layer materials are as shown in Table 5 below.

[0679] Compound ET-1

[0680] Sample electron transport auxiliary layer material Example 27 Compound 1-1 Example 28 Compound 1-2 Example 29 Compound 1-3 Example 30 Compound 1-8 Example 31 Compound 2-1 Example 32 Compound 2-2 Example 33 Compound 2-3 Example 34 Compound 2-8 Example 35 Compound 2-13 Example 36 Compound 2-14 Example 37 Compound 2-15 Example 38 Compound 2-25 Example 39 Compound 2-26 Example 40 Compound 2-27 Example 41 Compound 2-37 Example 42 Compound 2-38 Example 43 Compound 2-39 Example 44 Compound 2-49 Example 45 Compound 2-61 Example 46 Compound 2-75 Example 47 Compound 2-81 Example 48 Compound 2-95 Example 49 Compound 2-98 Example 50 Compound 2-101 Example 51 Compound 2-102 Example 52 Compound 2-103 Example 53 Compound 2-104 Example 54 Compound 2-108 Example 55 Compound 2-112 Comparative Example 7--Comparative Example 8E-1 Comparative Example 9E-2 Comparative Example 10E-3 Comparative Example 11E-4 Comparative Example 12E-5

[0681]

[0682] Evaluation Example 2

[0683] For the organic electroluminescent devices manufactured in Examples 27 to 55 and Comparative Examples 7 to 12, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 6 below.

[0684]

[0685] Sample driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 273.54557.7 Example 283.54547.9 Example 293.44557.9 Example 303.64537.7 Example 313.44558.1 Example 323.34548.0 Example 333.34558.2 Example 343.34538.0 Example 353.54548.0 Example 363.44548.0 Example 373.34558.1 Example 383.14558.3 ​​Example 393.24558.2 Example 403.24558.4 Example 413.34558.2 Example 423.34538.2 Example 433.24548.3 Example 443.44557.9Embodiment 453.24558.1Embodiment 463.24558.1Embodiment 473.24558.0Embodiment 483.54558.0Embodiment 493.44558.2Embodiment 503.34558.0Embodiment 513.44558.0Embodiment 523.44558.2Embodiment 533.24558.3Embodiment 543.24548.4Embodiment 553.14558.3Comparative Example 74.94575.3Comparative example 84.54577.0Comparative example 94.74607.2Comparative example 104.34597.5Comparative example 113.94557.3Comparative example 123.84557.2

[0686] From Table 6 above, it can be confirmed that the organic light-emitting devices manufactured in Examples 27 to 55 are superior to the driving voltage, light emission peak, and current efficiency of the organic light-emitting devices manufactured in Comparative Examples 7 to 12, respectively.

[0687]

[0688] When comparing the organic light-emitting compounds according to the present invention with E-1 to E-5 used as comparative examples, it can be confirmed that the electrical properties are superior when a cyclopentyl fluorene core is bonded to an azine group. In particular, when compared with Comparative Examples 2 to 5 or 8 to 11, it can be seen that the fluorene core substituted with an aliphatic ring group such as a cyclopentyl group contributes to the formation of a uniform morphology, and thus the device properties are superior. In addition, it has a smaller molecular weight than Comparative Example 6 having a cyclohexyl fluorene core, and thus is superior in terms of processability.

[0689]

[0690] In the results in Tables 1 and 2 above, compounds 1-1 to 1-130 having a cyano group showed excellent results when used as an electron transport layer material, and compounds 2-1 to 2-112 showed excellent results when used as an electron transport auxiliary layer material.

[0691]

[0692] While the embodiments of the present invention have been described above with reference to the attached drawings, 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 and not restrictive.

Claims

1. An organic luminescent compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 to X3 are identical or different from each other, and are each independently N or CR, provided that at least two of X1 to X3 are N, R , Ar1 and Ar2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, arylboron group having 6 to 60 carbon atoms, arylphosphinyl group having 6 to 60 carbon atoms, An arylamine group, an arylheteroarylamine group having 5 to 60 carbon atoms, or a heteroarylamine group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, L1 and L2 are each independently a single bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 2 to 18 carbon atoms, each of which may be unsubstituted or substituted, Dn means that n hydrogens are replaced by deuterium, and n is an integer greater than or equal to 0. a to c are each independently integers from 0 to 2.

2. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by one of the following chemical formulas 2 and 3: [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, Ar1 and Ar2 are each as defined in chemical formula 1, Ar3 is each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, arylboron group having 6 to 60 carbon atoms, arylphosphinyl group having 6 to 60 carbon atoms, arylamine group having 6 to 60 carbon atoms, An aryl heteroarylamine group having 5 to 60 carbon atoms or a heteroarylamine group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, X1 to X3, and D n are each as defined in chemical formula 1, b and c are as defined in chemical formula 1, respectively. d is an integer from 0 to 4, e is an integer from 0 to 6.

3. In paragraph 2, The above chemical formula 1 is an organic light-emitting compound represented by any one of the following chemical formulas 4 to 17: [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] In each of the chemical formulas 4 to 17 above, Ar1 and Ar2 are each as defined in chemical formula 1, Ar3 is each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 40 carbon atoms, alkenyl group having 2 to 40 carbon atoms, alkynyl group having 2 to 40 carbon atoms, cycloalkyl group having 3 to 40 carbon atoms, heterocycloalkyl group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, aryloxy group having 6 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, alkylboron group having 1 to 40 carbon atoms, arylboron group having 6 to 60 carbon atoms, arylphosphinyl group having 6 to 60 carbon atoms, arylamine group having 6 to 60 carbon atoms, An aryl heteroarylamine group having 5 to 60 carbon atoms or a heteroarylamine group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, X1 to X3, and D nare each as defined in chemical formula 1, d is an integer from 0 to 4, e is an integer from 0 to 6.

4. In paragraph 2, An organic light-emitting compound wherein the above Ar1 to Ar3 are each independently hydrogen, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, and each of them may be unsubstituted or substituted.

5. In paragraph 2, An organic light-emitting compound wherein the above Ar1 to Ar3 are each independently hydrogen, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, and each of them may be unsubstituted or substituted with a deuterium group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, or a heteroaryl group containing nitrogen and having 2 to 60 carbon atoms.

6. In paragraph 2, The organic light-emitting compound wherein Ar1, Ar2 and Ar3 are each independently hydrogen and one of the following chemical formulas A-1 to A-12: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] [Chemical Formula A-6] [Chemical Formula A-7] [Chemical Formula A-8] [Chemical Formula A-9] [Chemical Formula A-10] [Chemical Formula A-11] [Chemical Formula A-12] In the above chemical formulas A-1 to A-12, * indicates a site that is bonded to the chemical formula 1 above.

7. In paragraph 1, An organic luminescent compound represented by the above chemical formula 1, wherein the organic luminescent compound is any one of the following compounds.

8. An organic electroluminescent device comprising an organic luminescent compound according to paragraph 1.

9. In paragraph 8, 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.

10. In paragraph 9, 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.

11. Use of the organic luminescent compound according to paragraph 1 in an organic electroluminescent device.

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

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