Organic light-emitting compound and organic electroluminescent element 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 element comprising same, wherein the organic electroluminescent element may have a high current efficiency and a low driving voltage.

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2023-0169298, filed November 29, 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] Currently, NPB, BCP, Alq3, etc. are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as materials for light-emitting layers. In particular, among light-emitting layer materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of improving efficiency, are being used as phosphorescent dopant materials for blue, green, and red, and 4,4-dicarbazolybiphenyl (CBP) is being used as a phosphorescent host material.

[0011] 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.

[0012] Therefore, the development of high-performance organic layer materials is required.

[0013] Prior art literature

[0014] Republic of Korea Patent Publication No. 10-2018-0045116

[0015]

[0016] The present invention aims to provide a novel 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, an electron transport layer material and an electron transport auxiliary layer material, and its use.

[0017] In addition, the present invention aims to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel organic luminescent compound described above.

[0018] 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.

[0019]

[0020] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1 or chemical formula 2.

[0021] [Chemical Formula 1]

[0022]

[0023] [Chemical Formula 2]

[0024]

[0025] In each of the above chemical formulas 1 and 2,

[0026] X1 to X4 are each independently N or CR a and two or more of the above X1 to X4 are N,

[0027] Y is O or S,

[0028] Z is O, S or CR b R c and,

[0029] R aInland R c are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0030] L is represented by *-L1-L2-L3-*, wherein L1 to L3 are each independently a single bond, an arylene group having 2 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0031] R1 and R2 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or a alkyl group having 6 to 60 arylamine groups, each of which may be unsubstituted or substituted,

[0032] R3 and R4 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, 60 is an arylamine group or a cyano group, and at least one of R3 and R4 is a cyano group, and when R3 and R4 each have a ring structure, they can form a condensed ring with the ring on which R3 and R4 are substituted, and each of them can be unsubstituted or substituted,

[0033] a and b are each independently integers from 0 to 4, and a+b≥1,

[0034] c and d are each independently integers from 0 to 4.

[0035] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0036] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0037]

[0038] The organic light-emitting compound according to the present invention has a structure in which a condensed pyrimidine group and a xanthine group substituted with a cyano group are connected by an arylene linker, and due to the excellent dipole effect provided by the xanthine group substituted with the cyano group, charge injection and transport are fast, and a large amount of electrons can be transferred to the light-emitting layer, and since more electrons are distributed through the condensed pyrimidine group, the charge transport amount is excellent, and by separating them with an arylene linker, the band gap is improved, and an appropriate LUMO value can be obtained.

[0039] In addition, when the organic light-emitting compound according to the present invention is used in an electron transport layer or an electron transport auxiliary layer, the organic electroluminescent device can achieve a low driving voltage and greatly improve luminous performance, lifespan, and efficiency, and thus can be more effectively applied to full-color display panels, etc.

[0040] 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.

[0041]

[0042] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various different forms. These embodiments are provided solely to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the present invention, and the present invention is defined solely by the scope of the claims.

[0043] The terminology used herein is for the purpose of describing embodiments and is not intended to limit the present invention. In this specification, singular forms also include plural forms, unless specifically stated otherwise. As used herein, the terms "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0044] 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.

[0045] Hereinafter, embodiments of the present invention will be described in detail.

[0046] 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.

[0047] 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. In addition, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon, which is a structure having one more substituent in addition to the "aryl group." The arylene group may refer to, for example, a phenylene group, a naphthylene group, an anthracenylene group, a biphenylene group, etc., but is not limited thereto.

[0048] In the present invention, the term "heteroaryl group" may mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a 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, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group, acridinyl group, phenanthridinyl group, carbazolyl group,Nitrogen-containing heteroaryl groups including a phenanthrolinyl group, 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 thereof include oxygen-containing heteroaryl groups, such as a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, and a benzonaphthofuranyl group. In addition, the term "heteroarylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon containing at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom. In the heteroaryl group and heteroarylene group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms refers to the total number of atoms as the sum of the number of carbon and non-carbon atoms forming the ring, and may refer to the number of atoms including at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) in addition to carbon (C) atoms. For example, the heteroaryl group may have a nuclear number of 5 to 60, 5 to 30, or 5 to 20, and the heteroarylene group may have a nuclear number of 5 to 20.

[0049] 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.

[0050] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon having a ring structure. The cycloalkyl group may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclononyl group, and an adamantyl group, but is not limited thereto.

[0051] In the present invention, the term “alkenyl group” may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds in the middle or terminal of an alkyl group.

[0052] In the present invention, the term “alkynyl group” may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon triple bonds in the middle or terminal of an alkyl group.

[0053] In the present invention, the term "heterocycloalkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon having a ring structure, and the heterocycloalkyl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. In the heterocycloalkyl group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may mean the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heterocycloalkyl group may have 5 to 60, 5 to 30, or 5 to 20 nuclear atoms.

[0054] In the present invention, the terms “alkyloxy group” and “aryloxy group” may each mean a monovalent functional group derived from a compound in which oxygen is further contained at the linking site of the aforementioned alkyl group and aryl group.

[0055] In the present invention, the terms “alkylsilyl group” and “arylsilyl group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with the aforementioned alkyl group and aryl group, respectively.

[0056] In the present invention, the terms “alkylboron group” and “arylboron group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of borane is substituted with the aforementioned alkyl group and aryl group, respectively.

[0057] In the present invention, the terms “arylphosphine group” and “arylphosphine oxide group” may mean a monovalent functional group derived from a compound in which the above-described aryl group is substituted on an oxide and a phosphine oxide, respectively.

[0058] In the present invention, the term "arylamine group" may mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of ammonia is substituted with the aforementioned aryl group.

[0059] In the present invention, the term "substitution" independently means deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, It means being substituted with one or more substituents selected from the group consisting of an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, and a cyano group, and when substituted with multiple substituents, they may be the same or different from each other.

[0060]

[0061] Organic luminescent compounds

[0062] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1 or chemical formula 2.

[0063] [Chemical Formula 1]

[0064]

[0065] [Chemical Formula 2]

[0066]

[0067] In each of the above chemical formulas 1 and 2,

[0068] X1 to X4 are each independently N or CR a and two or more of the above X1 to X4 are N,

[0069] Y is O or S,

[0070] Z is O, S or CR b R c and,

[0071] R a Inland R c are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0072] L is represented by *-L1-L2-L3-*, wherein L1 to L3 are each independently a single bond, an arylene group having 2 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0073] R1 and R2 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heterocycloalkyl group having 5 to 40 nuclear atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylborone group having 6 to 60 carbon atoms, An arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or an arylamine group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0074] R3 and R4 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heteroaryl group having 5 to 40 nuclear atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, a 6 an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, an arylamine group or a cyano group having 6 to 60 carbon atoms, and at least one of R3 and R4 is a cyano group, and when R3 and R4 each have a ring structure, they can form a condensed ring with the ring on which R3 and R4 are substituted, and each of them can be unsubstituted or substituted,

[0075] a and b are each independently integers from 0 to 4, and a+b≥1,

[0076] c and d are each independently integers from 0 to 4.

[0077] Specifically, the above R a Inland R c , At least one group among the hydrogen atoms, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, alkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, arylphosphine groups, arylphosphine oxide groups and arylamine groups that can be on R1 to R4 and L is independently unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, It means being substituted with at least one substituent selected from the group consisting of a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylborone group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0078] The compound according to the present invention has a strong electron acceptor, such as a benzofuranopyrimidine group or a benzothienopyrimidine group, in its molecular structure, thereby exhibiting advantageous properties in electron injection and transfer. It exhibits excellent effects in improving the operating voltage of the device by enhancing the electron transfer ability to the light-emitting layer.

[0079] Furthermore, since it utilizes aromatic hydrocarbon groups and condensed structures rather than simple aliphatic ring groups, high thermal stability can be expected from the material. Furthermore, the absence of a crystallization temperature (Tc) for the material effectively improves device processability and lifespan.

[0080] Additionally, the bipolarity can be enhanced by substituting a cyano group for the xanthine or thioxanthine group. This enhances interaction with the cathode, enhancing electron generation within the device and effectively improving the initial operating voltage.

[0081] In one embodiment, in each of the chemical formulas 1 and 2,

[0082] X1 to X4 are each independently N or CR a and two or more of the above X1 to X4 are N,

[0083] Y is O or S,

[0084] Z is O, S or CR b R c and,

[0085] R a Inland R c are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, each of which may be unsubstituted or substituted,

[0086] L is represented by *-L1-L2-L3-*, wherein L1 to L3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, each of which may be unsubstituted or substituted,

[0087] R1 and R2 are each independently hydrogen, deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylborone group having 6 to 30 carbon atoms, An arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, each of which may be unsubstituted or substituted,

[0088] R3 and R4 are each independently hydrogen, deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylborone group having 6 to 30 carbon atoms, An arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an arylamine group or a cyano group having 6 to 30 carbon atoms, and at least one of R3 and R4 is a cyano group, and when R3 and R4 each have a ring structure, they can form a condensed ring with the ring on which R3 and R4 are substituted, and each of them can be unsubstituted or substituted,

[0089] a and b are each independently integers from 0 to 2, and a+b≥1,

[0090] c and d can each independently be an integer from 0 to 2.

[0091] In one embodiment, in each of the chemical formulas 1 and 2,

[0092] X1 to X4 are each independently N or CH, and at least two of the above X1 to X4 are N,

[0093] Y and Z are each independently O or S,

[0094] L is represented as *-L1-L2-L3-*, and L1 to L3 are each independently a single bond or an arylene group having 6 to 30 carbon atoms,

[0095] R1 and R2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms,

[0096] R3 and R4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, or a cyano group, and at least one of R3 and R4 is a cyano group, and when R3 and R4 each have a ring structure, they can form a condensed ring with the ring on which R3 and R4 are substituted.

[0097] a and b are each independently integers from 0 to 2, and a+b≥1,

[0098] c and d are each independently integers from 0 to 2.

[0099] In one embodiment, L may be represented by any one of the following chemical formulas L-1 to L-9.

[0100] [Chemical formula L-1]

[0101]

[0102] [Chemical formula L-2]

[0103]

[0104] [Chemical formula L-3]

[0105]

[0106] [Chemical formula L-4]

[0107]

[0108] [Chemical formula L-5]

[0109]

[0110] [Chemical formula L-6]

[0111]

[0112] [Chemical formula L-7]

[0113]

[0114] [Chemical formula L-8]

[0115]

[0116] [Chemical formula L-9]

[0117]

[0118] In each of the above chemical formulas L-1 to L-9, * represents a site bonded to the above chemical formula 1.

[0119] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 3 to 14.

[0120] [Chemical Formula 3]

[0121]

[0122] [Chemical Formula 4]

[0123]

[0124] [Chemical Formula 5]

[0125]

[0126] [Chemical Formula 6]

[0127]

[0128] [Chemical Formula 7]

[0129]

[0130] [Chemical Formula 8]

[0131]

[0132] [Chemical Formula 9]

[0133]

[0134] [Chemical Formula 10]

[0135]

[0136] [Chemical Formula 11]

[0137]

[0138] [Chemical Formula 12]

[0139]

[0140] [Chemical Formula 13]

[0141]

[0142] [Chemical Formula 14]

[0143]

[0144] In each of the above chemical formulas 3 to 14,

[0145] Z is O or S,

[0146] L is any one of the following chemical formulas L-1, L-3, L-4, L-7, and L-9,

[0147] R1 and R2 are each independently hydrogen, a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group or a fluorenyl group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group or a pyridinyl group,

[0148] One of R3 and R4 is a cyano group, and the other is hydrogen or a phenyl group, and when R3 and R4 are each a phenyl group, they can form a condensed ring with the ring on which R3 and R4 are substituted,

[0149] a and b are each independently integers from 0 to 2, and a+b≥1,

[0150] c and d can each independently be an integer from 0 to 2.

[0151] [Chemical formula L-1]

[0152]

[0153] [Chemical formula L-3]

[0154]

[0155] [Chemical formula L-4]

[0156]

[0157] [Chemical formula L-7]

[0158]

[0159] [Chemical formula L-9]

[0160]

[0161] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 4, 5, 7, 8, 10, and 13.

[0162] [Chemical Formula 4]

[0163]

[0164] [Chemical Formula 5]

[0165]

[0166] [Chemical Formula 7]

[0167]

[0168] [Chemical Formula 8]

[0169]

[0170] [Chemical Formula 10]

[0171]

[0172] [Chemical Formula 13]

[0173]

[0174] In each of the above chemical formulas 4, 5, 7, 8, 10 and 13,

[0175] Z is O or S,

[0176] L is any one of the following chemical formulas L-1, L-3, and L-4,

[0177] R1 and R2 are each independently hydrogen, a phenyl group, a biphenyl group or a dibenzothiophenyl group, and each of them may be unsubstituted or substituted with a pyridinyl group,

[0178] One of R3 and R4 is a cyano group, and the other is hydrogen or a phenyl group, and when R3 and R4 are each a phenyl group, they can form a condensed ring with the ring on which R3 and R4 are substituted,

[0179] a is 1, b is 0,

[0180] c is 0, and d can be 1 or 2.

[0181] [Chemical formula L-1]

[0182]

[0183] [Chemical formula L-3]

[0184]

[0185] [Chemical formula L-4]

[0186]

[0187] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one of compounds 1-1 to 1-180, compounds 2-1 to 2-180, and compounds 3-1 to 3-30.

[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] As a specific example, the compound represented by the above chemical formula 1 may be compound 1-1, 1-2, 1-7, 1-17, 1-28, 1-32, 1-45, 1-61, 1-72, 1-80, 1-84, 1-91, 1-95, 1-126, 1-128, 1-161, 2-1, 2-6, 2-16, 2-38, 2-63, 2-77, 2-98, 2-126, 2-134 or 2-161.

[0228] The novel organic light-emitting compound of the present invention has a structure in which a condensed pyrimidine group and a xanthine group substituted with a cyano group are connected by an arylene linker, and due to the excellent dipole effect provided by the xanthine group substituted with the cyano group, charge injection and transport are fast, and a large amount of electrons can be transferred to the light-emitting layer, and since more electrons are distributed through the condensed pyrimidine group, the charge transport amount is excellent, and by separating them with an arylene linker, the band gap is improved, and an appropriate LUMO (the lowest unoccupied molecular orbital) value can be obtained.

[0229] In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be achieved.

[0230]

[0231] Organic electroluminescent devices

[0232] 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.

[0233] 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.

[0234] anode

[0235] 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.

[0236] 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.

[0237] 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.

[0238] cathode

[0239] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0240] 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.

[0241] luminescent layer

[0242] 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.

[0243] 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.

[0244] 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.

[0245] electron transport region

[0246] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0247] 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.

[0248] 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.

[0249] 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 structure in which a condensed pyrimidine group and a xanthine group substituted with a cyano group are connected by an arylene linker, and due to the excellent dipole effect provided by the cyano group substituted xanthine group, charge injection and transport are fast, and a large amount of electrons can be transferred to the light-emitting layer, and since more electrons are distributed through the condensed pyrimidine group, the charge transport amount is excellent, and by separating them with the arylene linker, the band gap is improved, and an appropriate LUMO (the lowest unoccupied molecular orbital) value can be obtained. In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0250] 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.

[0251] 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).

[0252] electron transport auxiliary layer

[0253] 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.

[0254] 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 structure in which a condensed pyrimidine group and a xanthine group substituted with a cyano group are connected by an arylene linker, and due to the excellent dipole effect provided by the cyano group substituted xanthine group, charge injection and transport are fast, and a large amount of electrons can be transferred to the light-emitting layer, and since more electrons are distributed through the condensed pyrimidine group, the charge transport amount is excellent, and by separating them with the arylene linker, the band gap is improved, so that an appropriate LUMO (the lowest unoccupied molecular orbital) value can be obtained. In addition, by using the novel organic light-emitting compound according to the present invention as a material for the electron transport auxiliary layer, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0255] 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.

[0256] hole transport region

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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

[0261] 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.

[0262] 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).

[0263] hole transport auxiliary layer

[0264] The organic electroluminescent device of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region and the light-emitting layer. The light-emitting auxiliary layer serves to transport holes moving from the hole transport region to the light-emitting layer, while also serving to control the thickness of the organic layer. The light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer, and has a high triplet (T1) energy to prevent excitons in the light-emitting layer from diffusing to the hole transport layer.

[0265] These light-emitting auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the light-emitting auxiliary layers of the red, green, and blue organic light-emitting devices may be made of the same material.

[0266] The above-mentioned light-emitting auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives can be used. In addition, the light-emitting auxiliary layer may optionally include a p-type dopant in addition to the above-mentioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field can be used.

[0267] capping layer

[0268] 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.

[0269] 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).

[0270] 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.

[0271] 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.

[0272]

[0273] 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.

[0274] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0275] 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.

[0276] 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.

[0277]

[0278] 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.

[0279]

[0280] [Synthesis example]

[0281] [Synthesis Example 1]: Synthesis of Compound 1-1

[0282]

[0283] (Step 1) Synthesis of compound 1-1-i

[0284] Compound 1-1-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine 25 g (89.1 mmol, 1 eq), (2-chlorophenyl)boronic acid 16.7 g (106.9 mmol, 1.2 eq), Pd(PPh3) 44.1 g (3.6 mmol, 0.04 eq) and K2CO3 24.6 g (178.1 mmol, 2 eq) were added to a mixed solvent of THF 375 ml and H2O 125 ml and reacted while heating and refluxing for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography to obtain the compound 1-1-i(2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine)(25.4 g, yield 80%) was obtained.

[0285] Mass: [(M+H) + ] : 356.81

[0286] NMR( 1 H): σ= 7.84(2H, d) 7.70-7.53(7H, m), 7.38-7.36(3H, m), 7.22(1H, t)

[0287] (Step 2) Synthesis of compound 1-1

[0288] The obtained compound 1-1-i(2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 25.4 g(71.2 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 37.9 g(78.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.4 g(7.1 mmol, 0.1 eq) and K2CO3 21.7 g(156.7 mmol, 2 eq) were added to a mixed solvent of toluene 380 ml, EtOH 100 ml and H2O 100 ml and heated under reflux stirring for 8 hours. The reaction was carried out. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-1 (7-(2-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (42.5 g, yield 88%).

[0289] Mass: [(M+H) + ] : 677.76

[0290]

[0291] [Synthesis Example 2]: Synthesis of Compound 1-2

[0292]

[0293] (Step 1) Synthesis of compound 1-2-i

[0294] 25 g (89.1 mmol, 1 eq) of compound 1-2-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-2-i (2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (25.4 g, yield 80%).

[0295] Mass: [(M+H) + ] : 356.81

[0296] NMR( 1 H): σ= 7.84(2H, d) 7.70-7.53(7H, m), 7.38-7.36(3H, m), 7.22(1H, t)

[0297] (Step 2) Synthesis of compound 1-2

[0298] The obtained compound 1-2-i(2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 25.4 g(71.2 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-6-carbonitrile 37.9 g(78.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.4 g(7.1 mmol, 0.1 eq) and K2CO3 21.7 g(156.7 mmol, 2 eq) were added to a mixed solvent of toluene 380 ml, EtOH 100 ml and H2O 100 ml and heated under reflux stirring for 8 hours. The reaction was carried out. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-2(2-(2-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-6-carbonitrile)(42.0 g, yield 87%).

[0299] Mass: [(M+H) + ] : 677.76

[0300]

[0301] [Synthesis Example 3]: Synthesis of Compound 1-7

[0302]

[0303] (Step 1) Synthesis of compound 1-7-i

[0304] 25 g (89.1 mmol, 1 eq) of compound 1-7-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-7-i (2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (25.4 g, yield 80%).

[0305] Mass: [(M+H) + ] : 356.81

[0306] NMR( 1 H): σ= 7.84(2H, d) 7.70-7.53(7H, m), 7.38-7.36(3H, m), 7.22(1H, t)

[0307] (Step 2) Synthesis of compounds 1-7

[0308] The obtained compound 1-7-i(2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 25.4 g(71.2 mmol, 1 eq), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile 37.9 g(78.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.4 g(7.1 mmol, 0.1 eq) and K2CO3 21.7 g(156.7 mmol, 2 eq) were added to a mixed solvent of toluene 380 ml, EtOH 100 ml and H2O 100 ml and heated under reflux stirring for 8 hours. The reaction was carried out. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-7 (3'-(2-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile) (40.1 g, yield 83%).

[0309] Mass: [(M+H) + ] : 677.76

[0310]

[0311] [Synthesis Example 4]: Synthesis of Compound 1-17

[0312]

[0313] (Step 1) Synthesis of compound 1-17-i

[0314] 25 g (89.1 mmol, 1 eq) of compound 1-17-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (3-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-17-i (2-(3-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (26.4 g, yield 83%).

[0315] Mass: [(M+H) + ] : 356.81

[0316] NMR( 1 H): σ= 8.16(1H, d), 7.97(1H, s), 7.84(2H, d), 7.70-7.68(2H, m), 7.53-7.48(5H, m), 7.36(1H, t), 7.22(1H, t)

[0317] (Step 2) Synthesis of compound 1-17

[0318] The obtained compound 1-17-i(2-(3-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 26.4 g(73.9 mmol, 1 eq), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile 39.3 g(81.3 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.2 mmol, 0.03 eq), Xphos 3.5 g(7.4 mmol, 0.1 eq) and K2CO3 22.5 g(162.6 mmol, 2 eq) were added to a mixed solvent of toluene 400 ml, EtOH 105 ml and H2O 105 ml and heated under reflux for 8 hours. The reaction was performed while stirring. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-17 (3'-(3-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile) (41.6 g, yield 85%).

[0319] Mass: [(M+H) + ] : 677.76

[0320]

[0321] [Synthesis Example 5]: Synthesis of Compound 1-28

[0322]

[0323] (Step 1) Synthesis of compound 1-28-i

[0324] 25 g (89.1 mmol, 1 eq) of compound 1-28-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (4-chlorophenyl)boronic acid, 4.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3)4, and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-28-i (2-(4-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (27.6 g, yield 87%).

[0325] Mass: [(M+H) + ] : 356.81

[0326] NMR( 1 H): σ= 8.25(2H, d), 7.84(2H, d), 7.70(1H, d), 7.65(1H, d), 7.53-7.49(5H, m), 7.36(1H, t), 7.22(1H, t)

[0327] (Step 2) Synthesis of compound 1-28

[0328] The obtained compound 1-28-i(2-(4-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 27.6 g(77.5 mmol, 1 eq), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-4-carbonitrile 41.2 g(85.2 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.3 mmol, 0.03 eq), Xphos 3.7 g(7.7 mmol, 0.1 eq) and K2CO3 23.6 g(170.5 mmol, 2 eq) were added to a mixed solvent of toluene 400 ml, EtOH 105 ml and H2O 105 ml and heated under reflux for 8 hours. The reaction was performed while stirring. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-28 (4'-(4-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-4-carbonitrile) (44.1 g, yield 84%).

[0329] Mass: [(M+H) + ] : 677.76

[0330]

[0331] [Synthesis Example 6] Synthesis of Compound 1-32

[0332]

[0333] (Step 1) Synthesis of compound 1-32-i

[0334] 25 g (70.1 mmol, 1 eq) of compound 1-232-ii (4-([1,1'-biphenyl]-4-yl)-2-chlorobenzofuro[3,2-d]pyrimidine), 13.1 g (84.1 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 43.2 g (2.8 mmol, 0.04 eq) of Pd(PPh3), and 19.4 g (140.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-32-i (4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)benzofuro[3,2-d]pyrimidine) (26.4 g, yield 87%).

[0335] Mass: [(M+H) + ] : 432.91

[0336] NMR( 1 H): σ= 8.30(2H, d), 7.85(2H, d), 7.75-7.61(6H, m), 7.49-7.36(6H, m), 7.22(1H, t)

[0337] (Step 2) Synthesis of compound 1-32

[0338] The obtained compound 1-32-i(4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)benzofuro[3,2-d]pyrimidine) 26.4 g(61.0 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-6-carbonitrile 32.4 g(67.1 mmol, 1.1 eq), Pd(OAc) 20.4 g(1.8 mmol, 0.03 eq), Xphos 2.9 g(6.1 mmol, 0.1 eq) and K2CO3 18.5 g(134.1 mmol, 2 eq) were dissolved in 380 ml of toluene, 100 ml of EtOH and 100 ml of H2O. It was added to a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-32(2-(2-(4-([1,1'-biphenyl]-4-yl)benzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-6-carbonitrile)(36.8 g, yield 80%).

[0339] Mass: [(M+H) + ] : 753.86

[0340]

[0341] [Synthesis Example 7] Synthesis of Compound 1-45

[0342]

[0343] (Step 1) Synthesis of compound 1-45-i

[0344] 25 g (64.6 mmol, 1 eq) of compound 1-45-ii (2-chloro-4-(dibenzo[b,d]thiophen-4-yl)benzofuro[3,2-d]pyrimidine), 12.1 g (77.5 mmol, 1.2 eq) of (3-chlorophenyl)boronic acid, 43.0 g (2.6 mmol, 0.04 eq) of Pd(PPh3), and 17.9 g (129.2 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-45-i(2-(3-chlorophenyl)-4-(dibenzo[b,d]thiophen-4-yl)benzofuro[3,2-d]pyrimidine)(24.5 g, yield 82%).

[0345] Mass: [(M+H) + ] : 432.91

[0346] NMR( 1 H): σ= 88.55(1H, d), 8.45(1H, d), 8.16(1H, d), 6.97-7.93(3H, m), 7.70-7.65(3H, m), 7.56-.49(4H, m), 7.36(1H, t), 7.22(1H, t)

[0347] (Step 2) Synthesis of compound 1-45

[0348] The obtained compound 1-45-i(2-(3-chlorophenyl)-4-(dibenzo[b,d]thiophen-4-yl)benzofuro[3,2-d]pyrimidine) 24.5 g (53.0 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-5-carbonitrile 28.2 g (58.3 mmol, 1.1 eq), Pd(OAc) 20.4 g (1.6 mmol, 0.03 eq), Xphos 2.5 g (5.3 g) mmol, 0.1 eq) and 16.1 g of K2CO3 (116.6 mmol, 2 eq) in 400 ml of Toluene, 105 ml of EtOH and 105 ml of H2O. ml was added to a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-45(2-(3-(4-(dibenzo[b,d]thiophen-4-yl)benzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-5-carbonitrile)(33.6 g, yield 81%).

[0349] Mass: [(M+H) + ] : 783.91

[0350]

[0351] [Synthesis Example 8] Synthesis of Compound 1-61

[0352]

[0353] (Step 1) Synthesis of compound 1-61-i

[0354] 25 g (89.1 mmol, 1 eq) of compound 1-61-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 24.8 g (106.9 mmol, 1.2 eq) of (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-61-i (2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) (32.8 g, yield 85%).

[0355] Mass: [(M+H) + ] : 432.91

[0356] NMR( 1 H): σ= 8.38(1H, d), 7.97(2H, d), 7.84(2H, d), 7.73-7.61(4H, m), 7.53-7.39(8H, m), 7.22(1H, t)

[0357] (Step 2) Synthesis of compound 1-61

[0358] The obtained compound 1-61-i(2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) 32.8 g(75.7 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 40.3 g(83.3 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.3 mmol, 0.03 eq), Xphos 3.6 g(7.6 mmol, 0.1 eq), K2CO3 23.0 g(166.5 mmol, 2 eq) were mixed in 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O. It was placed in a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-61 (7-(3'-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)-[1,1'-biphenyl]-3-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (46.2 g, yield 81%).

[0359] Mass: [(M+H) + ] : 753.86

[0360]

[0361] [Synthesis Example 9] Synthesis of Compound 1-72

[0362]

[0363] (Step 1) Synthesis of compound 1-72-i

[0364] 25 g (89.1 mmol, 1 eq) of compound 1-72-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 24.8 g (106.9 mmol, 1.2 eq) of (3'-chloro-[1,1'-biphenyl]-4-yl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-72-i (2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) (30.8 g, yield 80%).

[0365] Mass: [(M+H) + ] : 432.91

[0366] NMR( 1 H): σ= 7.97(3H, d), 7.84(2H, d), 7.70(1H,md), 7.65(1H, d), 7.53-7.39(6H, m), 7.28-7.25(3H, m)

[0367] (Step 2) Synthesis of compound 1-72

[0368] The obtained compound 1-72-i(2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) 30.8 g(71.2 mmol, 1 eq), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 37.9 g(78.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.4 g(7.1 mmol, 0.1 eq) and K2CO3 21.7 g(156.7 mmol, 2 eq) were dissolved in 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O. It was added to a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-72(3'-(4'-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)-[1,1'-biphenyl]-3-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile)(41.9 g, yield 78%).

[0369] Mass: [(M+H) + ] : 753.86

[0370]

[0371] [Synthesis Example 10] Synthesis of Compound 1-80

[0372]

[0373] (Step 1) Synthesis of compound 1-80-i

[0374] 25 g (89.1 mmol, 1 eq) of compound 1-80-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 24.8 g (106.9 mmol, 1.2 eq) of (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-80-i (2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) (30.1 g, yield 78%).

[0375] Mass: [(M+H) + ] : 432.91

[0376] NMR( 1 H): σ= 8.38(1H, d), 7.95(2H, d), 7.84(2H, d), 7.73-7.36(11H, m), 7.22(1H, t)

[0377] (Step 2) Synthesis of compound 1-80

[0378] The obtained compound 1-80-i(2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) 30.1 g(69.5 mmol, 1 eq), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile 36.9 g(76.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.3 g(6.9 mmol, 0.1 eq) and K2CO3 21.1 g(152.8 mmol, 2 eq) were dissolved in 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O. It was added to a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-80(2'-(3'-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)-[1,1'-biphenyl]-3-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile)(39.3 g, yield 75%).

[0379] Mass: [(M+H) + ] : 753.86

[0380]

[0381] [Synthesis Example 11] Synthesis of Compound 1-84

[0382]

[0383] (Step 1) Synthesis of compound 1-84-i

[0384] 25 g (89.1 mmol, 1 eq) of compound 1-84-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 33.0 g (106.9 mmol, 1.2 eq) of (4''-chloro-[1,1':3',1''-terphenyl]-3-yl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-84-i (2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) (35.8 g, yield 78%).

[0385] Mass: [(M+H) + ] : 509.01

[0386] NMR( 1 H): σ= 8.38(1H, d), 8.10(2H, d), 7.94(2H, s), 7.84(2H, d), 7.73-7.49(12H, m), 7.36(1H, t), 7.22(1H, t)

[0387] (Step 2) Synthesis of compound 1-84

[0388] The obtained compound 1-84-i(2-(4''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4-phenylbenzofuro[3,2-d]pyrimidine) 35.8 g(70.4 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 37.4 g(77.4 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.1 mmol, 0.03 eq), Xphos 3.4 g(7.0 mmol, 0.1 eq) and K2CO3 21.4 g(154.8 mmol, 2 eq) were dissolved in 400 ml of Toluene, 100 ml of EtOH and Added to a mixed solvent containing 100 ml of H2O and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 1-84 (7-(3''-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)-[1,1':3',1''-terphenyl]-4-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (43.8 g, yield 75%).

[0389] Mass: [(M+H) + ] : 829.96

[0390]

[0391] [Synthesis Example 12] Synthesis of Compound 1-91

[0392]

[0393] (Step 1) Synthesis of compound 1-91-i

[0394] 25 g (89.1 mmol, 1 eq) of compound 1-91-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-91-i (2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (27.0 g, yield 85%).

[0395] Mass: [(M+H) + ] : 356.81

[0396] NMR( 1 H): σ= 7.84(2H, d) 7.70-7.53(7H,m), 7.38-7.36(3H, m), 7.22(1H, t)

[0397] (Step 2) Synthesis of compound 1-91

[0398] The obtained compound 1-91-i(2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 27.0 g(75.7 mmol, 1 eq), 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[benzo[c]fluorene-7,9'-xanthene]-5-carbonitrile 44.4 g(83.3 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.2 mmol, 0.03 eq), Xphos 3.6 g(7.6 mmol, 0.1 eq) and K2CO3 23.0 g(166.5 mmol, 2 eq) were added to a mixed solvent of 380 ml of toluene, 100 ml of EtOH and 100 ml of H2O and stirred for 8 hours. The reaction was carried out while stirring and heating under reflux. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-91 (9-(2-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[benzo[c]fluorene-7,9'-xanthene]-5-carbonitrile) (46.3 g, yield 84%).

[0399] Mass: [(M+H) + ] : 727.82

[0400]

[0401] [Synthesis Example 13] Synthesis of Compound 1-95

[0402]

[0403] (Step 1) Synthesis of compound 1-95-i

[0404] 25 g (89.1 mmol, 1 eq) of compound 1-95-ii (2-chloro-4-phenylbenzofuro[3,2-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (3-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-95-i (2-(2-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) (26.7 g, yield 84%).

[0405] Mass: [(M+H) + ] : 356.81

[0406] NMR( 1 H): σ= 8.16(1H, d), 7.97(1H, s), 7.84(2H, d), 7.70-7.68(2H, m), 7.53-7.48(5H, m), 7.36(1H, t), 7.22(1H, t)

[0407] (Step 2) Synthesis of compound 1-95

[0408] The obtained compound compound 1-95-i(2-(3-chlorophenyl)-4-phenylbenzofuro[3,2-d]pyrimidine) 26.7 g(74.8 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[benzo[c]fluorene-7,9'-xanthene]-9-carbonitrile 43.9 g(82.3 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.2 mmol, 0.03 eq), Xphos 3.6 g(7.5 mmol, 0.1 eq) and K2CO3 22.7 g(164.6 mmol, 2 eq) were added to a mixed solvent of 380 ml of toluene, 100 ml of EtOH and 100 ml of H2O and stirred for 8 hours. The reaction was carried out while stirring and heating under reflux. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-95 (5-(3-(4-phenylbenzofuro[3,2-d]pyrimidin-2-yl)phenyl)spiro[benzo[c]fluorene-7,9'-xanthene]-9-carbonitrile) (47.4 g, yield 87%).

[0409] Mass: [(M+H) + ] : 727.82

[0410]

[0411] [Synthesis Example 14] Synthesis of Compound 1-126

[0412]

[0413] (Step 1) Synthesis of compound 1-126-ii

[0414] Compound 1-126-iii (2,4-dichlorobenzofuro[3,2-d]pyrimidine) 30 g (125.5 mmol, 1 eq), (2-chlorophenyl)boronic acid 23.5 g (150.6 mmol, 1.2 eq), Pd(PPh3) 45.8 g (5.0 mmol, 0.04 eq), and K2CO3 34.7 g (251.0 mmol, 2 eq) were added to a mixed solvent of 450 ml of THF and 150 ml of H2O and reacted while stirring and heating under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-126-ii (2-chloro-4-(2-chlorophenyl)benzofuro[3,2-d]pyrimidine) (34.4 g, yield 87%).

[0415] Mass: [(M+H) + ] : 315.15

[0416] NMR( 1 H): σ= 7.71-7.65(4H, m), 7.38(2H, m), 7.22(1H, t)

[0417] (Step 2) Synthesis of compound 1-126-i

[0418] The obtained compound 1-126-ii (chloro-4-(2-chlorophenyl)benzofuro[3,2-d]pyrimidine) 34.4 g (109.2 mmol, 1 eq), phenylboronic acid 16.0 g (131.0 mmol, 1.2 eq), Pd(PPh3) 45.0 g (4.4 mmol, 0.04 eq), and K2CO3 30.2 g (218.4 mmol, 2 eq) were added to a mixed solvent of 500 ml of THF and 200 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 1-126-i (4-(2-chlorophenyl)-2-phenylbenzofuro[3,2-d]pyrimidine) (29.6 g, yield 76%).

[0419] Mass: [(M+H) + ] : 356.81

[0420] NMR( 1 H): σ= 8.35(2H, d), 7.71-7.61(4H, m), 7.50-7.36(6H, m), 7.22(1H, t)

[0421] (Step 3) Synthesis of compound 1-126

[0422] The obtained compound 1-126-i(4-(2-chlorophenyl)-2-phenylbenzofuro[3,2-d]pyrimidine) 29.6 g(83.0 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 44.1 g(91.3 mmol, 1.1 eq), Pd(OAc) 20.6 g(2.5 mmol, 0.03 eq), Xphos 4.0 g(8.3 mmol, 0.1 eq) and K2CO3 25.2 g(182.5 mmol, 2 eq) were added to a mixed solvent of toluene 450 ml, EtOH 120 ml and H2O 120 ml and heated under reflux for 8 hours. The reaction was performed while stirring. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-126 (7-(2-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (45.0 g, yield 80%).

[0423] Mass: [(M+H) + ] : 677.76

[0424]

[0425] [Synthesis Example 15] Synthesis of Compound 1-128

[0426]

[0427] (Step 1) Synthesis of compound 1-128-ii

[0428] Compound 1-128-iii (2,4-dichlorobenzofuro[3,2-d]pyrimidine) 30 g (125.5 mmol, 1 eq), (3-chlorophenyl)boronic acid 23.5 g (150.6 mmol, 1.2 eq), Pd(PPh3) 45.8 g (5.0 mmol, 0.04 eq), and K2CO3 34.7 g (251.0 mmol, 2 eq) were added to a mixed solvent of 450 ml of THF and 150 ml of H2O and reacted while stirring and heating under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-128-ii (2-chloro-4-(3-chlorophenyl)benzofuro[3,2-d]pyrimidine) (33.6 g, yield 85%).

[0429] Mass: [(M+H) + ] : 315.15

[0430] NMR( 1 H): σ= 7.97(1H, s), 7.72-7.65(3H, m), 7.48(2H, d), 7.36(1H, t), 7.22(1H, t)

[0431] (Step 2) Synthesis of compound 1-128-i

[0432] The obtained compound 1-128-ii (2-chloro-4-(3-chlorophenyl)benzofuro[3,2-d]pyrimidine) 33.6 g (106.7 mmol, 1 eq), phenylboronic acid 15.6 g (128.0 mmol, 1.2 eq), Pd(PPh3) 44.9 g (4.3 mmol, 0.04 eq), and K2CO3 29.5 g (213.3 mmol, 2 eq) were added to a mixed solvent of 500 ml of THF and 200 ml of H2O and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 1-128-i (4-(3-chlorophenyl)-2-phenylbenzofuro[3,2-d]pyrimidine) (30.4 g, yield 80%).

[0433] Mass: [(M+H) + ] : 356.81

[0434] NMR( 1 H): σ= 8.35(2H, d), 7.97(1H, s), 7.72-7.65(3H, m), 7.50-7.48(5H, m), 7.36(1H, t), 7.22(1H, t)

[0435] (Step 3) Synthesis of compound 1-128

[0436] The obtained compound 1-128-i(4-(3-chlorophenyl)-2-phenylbenzofuro[3,2-d]pyrimidine) 30.4 g(85.3 mmol, 1 eq), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile 45.4 g(93.9 mmol, 1.1 eq), Pd(OAc) 20.6 g(2.6 mmol, 0.03 eq), Xphos 4.1 g(8.5 mmol, 0.1 eq) and K2CO3 25.9 g(187.7 mmol, 2 eq) were added to a mixed solvent of toluene 450 ml, EtOH 120 ml and H2O 120 ml and heated under reflux for 8 hours. The reaction was performed while stirring. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-128 (3'-(3-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile) (47.4 g, yield 82%).

[0437] Mass: [(M+H) + ] : 677.76

[0438]

[0439] [Synthesis Example 16] Synthesis of Compound 1-161

[0440]

[0441] (Step 1) Synthesis of compound 1-161-i

[0442] 25 g (89.1 mmol, 1 eq) of compound 1-161-ii (2-chloro-4-phenylbenzofuro[2,3-d]pyrimidine), 16.7 g (106.9 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 44.1 g (3.6 mmol, 0.04 eq) of Pd(PPh3), and 24.6 g (178.1 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 1-161-i (2-(2-chlorophenyl)-4-phenylbenzofuro[2,3-d]pyrimidine) (26.7 g, yield 84%).

[0443] Mass: [(M+H) + ] : 356.81

[0444] NMR( 1 H): σ= 8.08(1H, d), 7.80(2H, d), 7.71-7.59(5H, m), 7.49-7.31(5H, m)

[0445] (Step 2) Synthesis of compound 1-161

[0446] The obtained compound 1-161-i(2-(2-chlorophenyl)-4-phenylbenzofuro[2,3-d]pyrimidine) 26.7 g(74.8 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 39.8 g(82.3 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.2 mmol, 0.03 eq), Xphos 3.6 g(7.5 mmol, 0.1 eq) and K2CO3 22.7 g(164.6 mmol, 2 eq) were added to a mixed solvent of toluene 400 ml, EtOH 100 ml and H2O 100 ml and heated under reflux for 8 hours. The reaction was performed while stirring. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC 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 that, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 1-161 (7-(2-(4-phenylbenzofuro[2,3-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (40.1 g, yield 79%).

[0447] Mass: [(M+H) + ] : 677.76

[0448]

[0449] [Synthesis Example 17] Synthesis of Compound 2-1

[0450]

[0451] (Step 1) Synthesis of compound 2-1-i

[0452] 25 g (84.2 mmol, 1 eq) of compound 2-1-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 15.8 g (101.1 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-1-i (2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (26.7 g, yield 85%).

[0453] Mass: [(M+H) + ] : 372.87

[0454] NMR( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.71(1H, d), 7.61(1H, d), 7.53-7.38(7H, m)

[0455] (Step 2) Synthesis of compound 2-1

[0456] The obtained compound 2-1-i (2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 26.7 g (71.6 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 38.1 g (78.8 mmol, 1.1 eq), Pd(OAc)20. 5 g (2.1 mmol, 0.03 eq), 3.4 g (7.2 mmol, 0.1 eq) of Xphos, and 21.8 g (157.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the product was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-1 (7-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (40.6 g, yield 82%).

[0457] Mass: [(M+H) + ] : 693.82

[0458]

[0459] [Synthesis Example 18] Synthesis of Compound 2-6

[0460]

[0461] (Step 1) Synthesis of compound 2-6-i

[0462] 25 g (84.2 mmol, 1 eq) of compound 2-6-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 15.8 g (101.1 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O, and the mixture was stirred under reflux and heated for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-6-i (2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (27.3 g, yield 87%).

[0463] Mass: [(M+H) + ] : 372.87

[0464] NMR( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.71(1H, d), 7.61(1H, d), 7.53-7.38(7H, m)

[0465] (Step 2) Synthesis of compound 2-6

[0466] The obtained compound 2-6-i(2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 27.3 g(73.3 mmol, 1 eq), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 39.0 g(80.6 mmol, 1.1 eq), Pd(OAc) 20.5 g(2.2 mmol, 0.03 eq), Xphos 3.5 g(7.3 mmol, 0.1 eq) and K2CO3 22.3 g(161.2 mmol, 2 eq) were added to a mixed solvent of toluene 400 ml, EtOH 100 ml and H2O 100 ml and stirred for 6 hours. The reaction was carried out while stirring and heating under reflux. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-6 (2'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile (40.7 g, yield 80%).

[0467] Mass: [(M+H) + ] : 693.82

[0468]

[0469] [Synthesis Example 19] Synthesis of Compound 2-16

[0470]

[0471] (Step 1) Synthesis of compound 2-16-i

[0472] 25 g (84.2 mmol, 1 eq) of compound 2-16-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 15.8 g (101.1 mmol, 1.2 eq) of (3-chlorophenyl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-16-i (2-(3-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (27.3 g, yield 87%).

[0473] Mass: [(M+H) + ] : 372.87

[0474] NMR( 1 H): σ= 8.16(1H, d), 8.05(1H, d), 7.97-7.93(2H, m), 7.84(2H, d), 7.53-7.42(7H, m)

[0475] (Step 2) Synthesis of compound 2-16

[0476] The obtained compound 2-16-i (2-(3-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 27.3 g (73.3 mmol, 1 eq), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 39.0 g (80.6 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.2 mmol, 0.03 eq), Xphos 3.5 g (7.3 mmol, 0.1 eq) and K2CO3 22.3 g (161.2 mmol, 2 eq) were added to a mixed solvent of 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O and stirred for 6 The reaction was carried out while stirring and heating under reflux for an hour. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-16 (2'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (42.7 g, yield 84%).

[0477] Mass: [(M+H) + ] : 693.82

[0478]

[0479] [Synthesis Example 20] Synthesis of Compound 2-38

[0480]

[0481] (Step 1) Synthesis of compound 2-38-i

[0482] 25 g (66.9 mmol, 1 eq) of compound 2-38-ii (2-chloro-4-(4-(pyridin-3-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine), 12.5 g (80.2 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 43.1 g (2.7 mmol, 0.04 eq) of Pd(PPh3), and 18.5 g (133.7 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 7 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-38-i (2-(2-chlorophenyl)-4-(4-(pyridin-3-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine) (23.5 g, yield 78%).

[0483] Mass: [(M+H) + ] : 449.96

[0484] NMR( 1 H): σ= 9.24(1H, s), 8.70(1H, d), 8.42(1H, d), 8.30(2H, d), 8.05(1H, d), 7.93(1H. d), 7.71(1H, d), 7.61-7.38(6H, m), 7.25(2H, d)

[0485] (Step 2) Synthesis of compound 2-38

[0486] The obtained compound 2-38-i(2-(2-chlorophenyl)-4-(4-(pyridin-3-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine) 23.5 g(52.2 mmol, 1 eq), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-4-carbonitrile 27.7 g(57.4 mmol, 1.1 eq), Pd(OAc) 20.4 g(1.6 mmol, 0.03 eq), Xphos 2.5 g(5.2 mmol, 0.1 eq) and K2CO3 15.9 g(114.7 mmol, 2 eq) were dissolved in 360 ml of toluene, 90 ml of EtOH and H2O 90 ml of mixed solvent was added and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 2-38(2'-(2-(4-(4-(pyridin-3-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-4-carbonitrile)(32.2 g, yield 80%).

[0487] Mass: [(M+H) + ] : 770.91

[0488]

[0489] [Synthesis Example 21] Synthesis of Compound 2-63

[0490]

[0491] (Step 1) Synthesis of compound 2-63-i

[0492] 25 g (84.2 mmol, 1 eq) of compound 2-63-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 23.5 g (101.1 mmol, 1.2 eq) of (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-63-i (2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (31.1 g, yield 82%).

[0493] Mass: [(M+H) + ] : 448.97

[0494] NMR( 1 H): σ= 8.38(1H, d), 8.10-8.05(3H, m), 7.94(2H, d), 7.84(2H, d), 7.73(1H, d), 7.73-7.42(8H, m)

[0495] (Step 2) Synthesis of compound 2-63

[0496] The obtained compound 2-63-i (2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 31.1 g (69.1 mmol, 1 eq), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile 36.7 g (76.0 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.1 mmol, 0.03 eq), Xphos 3.3 g (6.9 mmol, 0. 1 eq) and K2CO3 21.0 g (152.0 mmol, 2 eq) were dissolved in 450 ml of toluene, 120 ml of EtOH and H2O 120 ml of mixed solvent was added and reacted while heating and refluxing for 6 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 2-61 (6-(3'-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)-[1,1'-biphenyl]-4-yl)spiro[fluorene-9,9'-xanthene]-3-carbonitrile) (44.7 g, yield 84%).

[0497] Mass: [(M+H) + ] : 769.92

[0498]

[0499] [Synthesis Example 22] Synthesis of Compound 2-77

[0500]

[0501] (Step 1) Synthesis of compound 2-77-i

[0502] 25 g (84.2 mmol, 1 eq) of compound 2-77-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 23.5 g (101.1 mmol, 1.2 eq) of (3'-chloro-[1,1'-biphenyl]-4-yl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-77-i (2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (32.1 g, yield 85%).

[0503] Mass: [(M+H) + ] : 448.97

[0504] NMR( 1 H): σ= 8.05(1H, d), 7.97-7.93(4H, m), 7.84(2H, d), 7.5-7.42(8H, m), 7.25(2H, d)

[0505] (Step 2) Synthesis of compound 2-77

[0506] The obtained compound 2-77-i (2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 32.1 g (71.6 mmol, 1 eq), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 38.1 g (78.8 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.1 mmol, 0.03 eq), Xphos 3.4 g (7.2 mmol, 0.1 eq) and K2CO3 21.8 g (157.5 mmol, 2 eq) were dissolved in 450 ml of toluene, 120 ml of EtOH and H2O 120 ml of mixed solvent was added and reacted while heating and refluxing for 6 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 2-77 (2'-(4'-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)-[1,1'-biphenyl]-3-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (46.8 g, yield 85%).

[0507] Mass: [(M+H) + ] : 769.92

[0508]

[0509] [Synthesis Example 23] Synthesis of Compound 2-98

[0510]

[0511] (Step 1) Synthesis of compound 2-98-i

[0512] 25 g (84.2 mmol, 1 eq) of compound 2-98-ii (2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine), 15.8 g (101.1 mmol, 1.2 eq) of (3-chlorophenyl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-98-i (2-(3-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (27.3 g, yield 87%).

[0513] Mass: [(M+H) + ] : 372.87

[0514] NMR( 1 H): σ= 8.16(1H, d), 8.05(1H, d), 7.97-7.93(2H, m), 7.84(2H, d), 7.53-7.42(7H, m)

[0515] (Step 2) Synthesis of compound 2-98

[0516] The obtained compound 2-98-i (2-(3-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 27.3 g (73.3 mmol, 1 eq), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[benzo[c]fluorene-7,9'-xanthene]-10-carbonitrile 43.0 g (80.6 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.2 mmol, 0.03 eq), Xphos 3.5 g (7.3 mmol, 0.1 eq) and K2CO3 22.3 g (161.2 mmol, 2 eq) were mixed in 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O. It was placed in a mixed solvent and reacted while heating and refluxing for 8 hours. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After that, it was dissolved in toluene, and hexane was added dropwise, and the white crystals produced were filtered to obtain compound 2-98 (3'-(3-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[benzo[c]fluorene-7,9'-xanthene]-10-carbonitrile) (44.7 g, yield 82%).

[0517] Mass: [(M+H) + ] : 743.88

[0518]

[0519] [Synthesis Example 24] Synthesis of Compound 2-126

[0520]

[0521] (Step 1) Synthesis of compound 2-126-ii

[0522] Compound 2-126-iii (2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine) 30 g (117.6 mmol, 1 eq), (2-chlorophenyl)boronic acid 22.1 g (141.1 mmol, 1.2 eq), Pd(PPh3) 45.4 g (4.7 mmol, 0.04 eq), and K2CO3 32.5 g (235.2 mmol, 2 eq) were added to a mixed solvent of 450 ml of THF and 150 ml of H2O and reacted while stirring and heating under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-126-ii (2-chloro-4-(2-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine) (32.4 g, yield 83%).

[0523] Mass: [(M+H) + ] : 332.21

[0524] NMR( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.71(1H, d), 7.61(1H, d), 7.49-7.38(4H, m)

[0525] (Step 2) Synthesis of compound 2-126-i

[0526] The obtained compound 2-126-ii (2-chloro-4-(2-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine) 32.4 g (97.6 mmol, 1 eq), phenylboronic acid 14.3 g (117.1 mmol, 1.2 eq), Pd(PPh3) 44.5 g (3.9 mmol, 0.04 eq), and K2CO3 27.0 g (195.2 mmol, 2 eq) were added to a mixed solvent of 500 ml of THF and 200 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 2-126-i (4-(2-chlorophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (29.5 g, yield 81%).

[0527] Mass: [(M+H) + ] : 372.87

[0528] NMR( 1 H): σ= 8.35(2H, d), 8.05(1H, d), 7.93(1H, d), 7.71(1H, d), 7.61(1H, d), 7.50-7.38(7H, m)

[0529] (Step 3) Synthesis of compound 2-126

[0530] The obtained compound 2-126-i (4-(2-chlorophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 29.5 g (79.1 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 42.0 g (87.0 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.4 mmol, 0.03 eq), Xphos 3.8 g (7.9 mmol, 0.1 eq) and K2CO3 24.0 g (173.9 mmol, 2 eq) were added to a mixed solvent of 450 ml of toluene, 120 ml of EtOH and 120 ml of H2O, and 8 The reaction was carried out while stirring and heating under reflux for an hour. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-126 (7-(2-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (45.0 g, yield 82%).

[0531] Mass: [(M+H) + ] : 693.82

[0532]

[0533] [Synthesis Example 25] Synthesis of Compound 2-134

[0534]

[0535] (Step 1) Synthesis of compound 2-134-ii

[0536] Compound 2-134-iii (2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine) 30 g (117.6 mmol, 1 eq), (4-chlorophenyl)boronic acid 22.1 g (141.1 mmol, 1.2 eq), Pd(PPh3) 45.4 g (4.7 mmol, 0.04 eq), and K2CO3 32.5 g (235.2 mmol, 2 eq) were added to a mixed solvent of 450 ml of THF and 150 ml of H2O and reacted while stirring and heating under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-134-ii (2-chloro-4-(4-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine) (32.9 g, yield 84%).

[0537] Mass: [(M+H) + ] : 332.21

[0538] NMR( 1 H): σ= 8.05(1H, d), 7.98-7.93(3H, m), 7.52-7.42(4H, m)

[0539] (Step 2) Synthesis of compound 2-134-i

[0540] The obtained compound 2-134-ii (2-chloro-4-(4-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine) 32.9 g (98.8 mmol, 1 eq), phenylboronic acid 14.5 g (118.5 mmol, 1.2 eq), Pd(PPh3) 44.6 g (4.0 mmol, 0.04 eq), and K2CO3 27.3 g (197.6 mmol, 2 eq) were added to a mixed solvent of 500 ml of THF and 200 ml of H2O and reacted while stirring and heating under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 2-134-i (4-(4-chlorophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) (30.9 g, yield 84%).

[0541] Mass: [(M+H) + ] : 372.87

[0542] NMR( 1 H): σ= 8.35(2H, d), 8.05(1H, d), 7.98-7.93(3H, m), 7.52-7.42(7H, m)

[0543] (Step 3) Synthesis of compound 2-134

[0544] The obtained compound 2-134-i (4-(4-chlorophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine) 30.2 g (83.0 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 48.1 g (99.6 mmol, 1.1 eq), Pd(OAc) 20.6 g (2.5 mmol, 0.03 eq), Xphos 4.0 g (8.3 mmol, 0.1 eq) and K2CO3 27.5 g (199.1 mmol, 2 eq) were added to a mixed solvent of 450 ml of toluene, 120 ml of EtOH and 120 ml of H2O, and 8 The reaction was carried out while stirring and heating under reflux for an hour. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-134 (7-(4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (46.1 g, yield 80%).

[0545] Mass: [(M+H) + ] : 693.82

[0546]

[0547] [Synthesis Example 26] Synthesis of Compound 2-161

[0548]

[0549] (Step 1) Synthesis of compound 2-161-i

[0550] 25 g (84.2 mmol, 1 eq) of compound 2-161-ii (2-chloro-4-phenylbenzo[4,5]thieno[2,3-d]pyrimidine), 15.8 g (101.1 mmol, 1.2 eq) of (2-chlorophenyl)boronic acid, 43.9 g (3.4 mmol, 0.04 eq) of Pd(PPh3), and 23.3 g (168.5 mmol, 2 eq) of K2CO3 were added to a mixed solvent of 375 ml of THF and 125 ml of H2O and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and methylene chloride (MC) 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 to obtain compound 2-161-i (2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[2,3-d]pyrimidine) (26.7 g, yield 85%).

[0551] Mass: [(M+H) + ] : 372.87

[0552] NMR( 1 H): σ= 8.45(1H, d), 7.93(1H, d), 7.80(2H, d), 7.71-7.49(7H, m), 7.38(2H, d)

[0553] (Step 2) Synthesis of compound 2-161

[0554] The obtained compound 2-161-i (2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[2,3-d]pyrimidine) 27.3 g (71.6 mmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile 38.1 g (78.8 mmol, 1.1 eq), Pd(OAc) 20.5 g (2.1 mmol, 0.03 eq), Xphos 3.4 g (7.2 mmol, 0.1 eq) and K2CO3 21.8 g (157.5 mmol, 2 eq) were added to a mixed solvent of 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O, and 8 The reaction was carried out while stirring and heating under reflux for an hour. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Afterwards, the mixture was dissolved in toluene, and hexane was added dropwise. The resulting white crystals were filtered to obtain compound 2-161 (7-(2-(4-phenylbenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)phenyl)spiro[fluorene-9,9'-xanthene]-2-carbonitrile) (41.7 g, yield 84%).

[0555] Mass: [(M+H) + ] : 693.82

[0556]

[0557] [Examples and Comparative Examples]

[0558] [Examples 1 to 26 and Comparative Examples 1 to 6]: Fabrication of blue organic electroluminescent devices

[0559] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0560] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0561] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 on the light-emitting auxiliary layer to a thickness of 20 nm, the electron transport layer was formed by co-depositing an electron transport layer material and Liq in a weight ratio of 1:1 on the light-emitting layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structures of HI, HAT-CN6, EB, BH, BD and Liq are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0562] HI HAT-CN6 EB BH BD Liq

[0563] Electron transport layer material Example 1 Compound 1-1 Example 2 Compound 1-2 Example 3 Compound 1-7 Example 4 Compound 1-17 Example 5 Compound 1-28 Example 6 Compound 1-32 Example 7 Compound 1-45 Example 8 Compound 1-61 Example 9 Compound 1-72 Example 10 Compound 1-80 Example 11 Compound 1-84 Example 12 Compound 1-91 Example 13 Compound 1-95 Example 14 Compound 1-126 Example 15 Compound 1-128 Example 16 Compound 1-161 Example 17 Compound 2-1 Example 18 Compound 2-6 Example 19 Compound 2-16 Example 20 Compound 2-38 Example 21 Compound 2-63 Example 22 Compound 2-77 Example 23 Compound 2-98 Example 24 Compound 2-126 Example 25 Compound 2-134 Example 26 Compound 2-161 Comparative Example 1 Alq3 Comparative Example 2E-1 Comparative Example 3E-2 Comparative Example 4E-3 Comparative Example 5E-4 Comparative Example 6E-5

[0564]

[0565] [Examples 27 to 52 and Comparative Examples 7 to 12]: Fabrication of blue organic electroluminescent devices

[0566] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0567] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0568] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 to a thickness of 20 nm on the light-emitting auxiliary layer, the electron transport auxiliary layer was formed by depositing an electron transport auxiliary layer material in a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by co-depositing ET and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structure of the above ET is shown in Table 3 below, and the electron transport auxiliary layer material is as shown in Table 4 below.

[0569] ET

[0570] Electron transport auxiliary layer material Example 27 Compound 1-1 Example 28 Compound 1-2 Example 29 Compound 1-7 Example 30 Compound 1-17 Example 31 Compound 1-28 Example 32 Compound 1-32 Example 33 Compound 1-45 Example 34 Compound 1-61 Example 35 Compound 1-72 Example 36 Compound 1-80 Example 37 Compound 1-84 Example 38 Compound 1-91 Example 39 Compound 1-95 Example 40 Compound 1-126 Example 41 Compound 1-128 Example 42 Compound 1-161 Example 43 Compound 2-1 Example 44 Compound 2-6 Example 45 Compound 2-16 Example 46 Compound 2-38 Example 47 Compound 2-63 Example 48 Compound 2-77 Example 49 Compound 2-98 Example 50 Compound 2-126 Example 51 Compound 2-134 Example 52 Compound 2-161 Comparative Example 7 No formation of electron transport auxiliary layer Comparative Example 8 E-1 Comparative Example 9E-2 Comparative Example 10E-3 Comparative Example 11E-4 Comparative Example 12E-5

[0571]

[0572] [Experimental Example]

[0573] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 26 and Comparative Examples 1 to 6

[0574] For the organic electroluminescent devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 6, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 5 below.

[0575] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 13.44527.9 Example 23.44547.8 Example 33.44517.9 Example 43.44528.0 Example 53.34547.8 Example 63.44528.1 Example 73.54568.2 Example 83.44548.0 Example 93.44558.1 Example 103.54578.0 Example 113.44527.7 Example 123.54528.2 Example 133.44528.0 Example 143.44507.8 Example 153.44557.8 Example 163.34567.7 Example 173.54588.1 Example 183.54598.2 Example 193.54608.2 Example 203.64608.3 Example 213.44578.0 Example 223.44568.1 Example 233.64578.2 Example 243.54588.0 Example 253.44557.9 Example 263.54568.0 Comparative Example 14.64575.6 Comparative Example 24.44626.4 Comparative Example 34.34676.5 Comparative Example 45.14624.5 Comparative Example 54.14556.9 Comparative Example 64.04566.5

[0576] Referring to Table 5 above, the organic electroluminescent devices manufactured in Examples 1 to 26 showed generally superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 1 to 6.

[0577]

[0578] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 27 to 52 and Comparative Examples 7 to 12

[0579] For the organic electroluminescent devices manufactured in Examples 27 to 52 and Comparative Examples 7 to 12, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 6 below.

[0580] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 273.34527.7 Example 283.34547.7 Example 293.44517.8 Example 303.34527.7 Example 313.24547.6 Example 323.44528.0 Example 333.44568.1 Example 343.44547.8 Example 353.34558.0 Example 363.54577.8 Example 373.44527.6 Example 383.54528.0 Example 393.34527.9 Example 403.44507.7 Example 413.34557.6 Example 423.34567.5 Example 433.44588.0 Example 443.44598.0 Example 453.54608.0 Example 463.54608.1 Example 473.44577.7 Example 483.44567.9 Example 493.54578.0 Example 503.44587.8 Example 513.44557.7 Example 523.44567.8 Comparative Example 74.94575.3 Comparative Example 84.34626.1 Comparative Example 94.34676.2 Comparative Example 105.14624.4 Comparative Example 113.94557.2 Comparative example 123.84566.4

[0581] Referring to Table 6 above, the organic electroluminescent devices manufactured in Examples 27 to 52 showed generally superior results in the evaluation of driving voltage, luminescence peak, and current efficiency compared to the organic electroluminescent devices manufactured in Comparative Examples 7 to 12. Specifically, referring to Tables 5 and 6 above, when comparing the organic electroluminescent compound of the invention with E-1 and E-2, it can be confirmed that the condensed pyrimidine group of the organic electroluminescent compound of the invention shows better efficiency than the monocyclic azine group or quinoline group. In particular, the improvement in driving voltage was excellent, and this is because the benzofuranopyrimidine group or benzothienopyrimidine group of the organic electroluminescent compound of the present invention has a wide conjugation area, so that more electrons are distributed, resulting in excellent initial driving voltage and total charge transport capacity.

[0582] In addition, when comparing the organic light-emitting compound of the present invention with E-3, when an azine group (nitrogen-containing) is substituted rather than a general dibenzofuran group, it has more electrons and can thus perform the role of an EWG (electron withdrawing group), thereby improving the operating voltage as well as the current efficiency of the device.

[0583] In addition, when comparing the organic light-emitting compound of the present invention with E-4, when a nitrile group (cyano group) is substituted, the interface characteristics with an adjacent cathode are made better, which is advantageous for electron injection and initial charge generation, and as a result, a larger amount of electrons can be obtained from the cathode and transported to the light-emitting layer, thereby improving the initial driving voltage of the device and the light-emitting efficiency, and by making the dipole moment higher, the stacking between the electrode and the organic material during deposition is improved, thereby minimizing defects within the device.

[0584] In addition, when comparing the organic light-emitting compound of the present invention with E-5, the organic light-emitting compound of the present invention has the effect of separating the LUMO - HOMO orbitals by adding an arylene linker to the center and appropriately dividing the xanthine group as a donating group and the benzofuranopyrimidine group and benzothienopyrimidine group as a withdrawing group, thereby improving the bandgap to have an appropriate LUMO value.

[0585] In addition, when comparing the present invention with Comparative Example 7, which did not form an electron transport auxiliary layer, it can be seen that it helps to improve efficiency to a certain level by separating excitons within the light-emitting layer, and it can be seen that the electron transfer ability from the electron transport layer to the light-emitting layer is excellent, which is also advantageous in terms of driving voltage.

[0586] Referring to Tables 5 and 6 above, it can be seen that the xanthene group substituted with a cyano group exhibits superior performance when used as an electron transport layer rather than as an electron transport auxiliary layer due to the rapid charge generation and injection performance. This can be attributed to the advantageous properties for rapid electron injection and transport due to the excellent dipole effect obtained by the cyano group substitution of the xanthene group, which allows for superior performance in transferring a large amount of electrons to the light-emitting layer.

[0587]

[0588] While the embodiments of the present invention have been described above, those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical concept or essential features thereof. Therefore, the embodiments described above should be understood to be illustrative in all respects, not restrictive.

Claims

1. An organic luminescent compound represented by the following chemical formula 1 or chemical formula 2: [Chemical Formula 1] [Chemical formula 2] In each of the chemical formulas 1 and 2 above, X 1 Inland X 4 are each independently N or CR a And, the above X 1 Inland X 4 Two or more of them are N, Y is O or S, Z is O, S or CR b R c And, R a Inland R c are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted, L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inland L 3 are each independently a single bond, an arylene group having 2 to 60 carbon atoms or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, R 1 and R 2 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or a are arylamine groups, each of which may be unsubstituted or substituted, R 3 and R 4 are each independently hydrogen, deuterium, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, An arylamine group or a cyano group, and the above R 3 and R 4 At least one of the R is a cyano group, 3 and R 4 In the case of each ring structure, R 3 and R 4 can form substituted rings and condensed rings, each of which can be unsubstituted or substituted, a and b are each independently an integer from 0 to 4, and a+b≥1, c and d are each independently an integer from 0 to 4.

2. In paragraph 1, Above X 1 Inland X 4 are each independently N or CR a And, the above X 1 Inland X 4 Two or more of them are N, The above Y is O or S, The above Z is O, S or CR b R c And, Above R a Inland R c are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, each of which may be unsubstituted or substituted, The above L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inland L 3 are each independently a single bond, an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms, each of which may be unsubstituted or substituted, Above R 1 and R 2 are each independently hydrogen, deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyloxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or a are arylamine groups, each of which may be unsubstituted or substituted, Above R 3 and R 4 are each independently hydrogen, deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, An arylamine group or a cyano group, and the above R 3 and R 4 At least one of the R is a cyano group, 3 and R 4 In the case of each ring structure, the R 3 and R 4 can form substituted rings and condensed rings, each of which can be unsubstituted or substituted, wherein a and b are each independently an integer from 0 to 2, and a+b≥1, An organic luminescent compound wherein c and d are each independently an integer from 0 to 2.

3. In paragraph 1, Above X 1 Inland X 4 are each independently N or CH, and the X 1 Inland X 4 Two or more of them are N, The above Y and Z are each independently O or S, The above L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inland L 3 are each independently a single bond or an arylene group having 6 to 30 carbon atoms, Above R 1 and R 2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, each of which may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, Above R 3 and R 4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, or a cyano group, and R 3 and R 4 At least one of the R is a cyano group, 3 and R 4 In the case of each ring structure, the R 3 and R 4 It can form a substituted ring and a condensed ring, wherein a and b are each independently an integer from 0 to 2, and a+b≥1, An organic luminescent compound wherein c and d are each independently an integer from 0 to 2.

4. In paragraph 1, The above L is an organic light-emitting compound represented by any one of the following chemical formulas L-1 to L-9: [Chemical formula L-1] [Chemical formula L-2] [Chemical formula L-3] [Chemical formula L-4] [Chemical formula L-5] [Chemical formula L-6] [Chemical formula L-7] [Chemical formula L-8] [Chemical formula L-9] In each of the above chemical formulas L-1 to L-9, * represents a site bonded to the above chemical formula 1.

5. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound represented by any one of the following chemical formulas 3 to 14: [Chemical Formula 3] [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] In each of the chemical formulas 3 to 14 above, Z is O or S, L is any one of the following chemical formulas L-1, L-3, L-4, L-7, and L-9, R 1 and R 2 are each independently hydrogen, a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group or a fluorenyl group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group or a pyridinyl group, R 3 and R 4 One of them is a cyano group, the other is a hydrogen or phenyl group, and the R 3 and R 4 In the case where each is a phenyl group, the above R 3 and R 4 It can form a substituted ring and a condensed ring, a and b are each independently an integer from 0 to 2, and a+b≥1, c and d are each independently an integer from 0 to 2. [Chemical formula L-1] [Chemical formula L-3] [Chemical formula L-4] [Chemical formula L-7] [Chemical formula L-9] 6. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound represented by any one of the following chemical formulas 4, 5, 7, 8, 10 and 13: [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 7] [Chemical formula 8] [Chemical Formula 10] [Chemical Formula 13] In each of the above chemical formulas 4, 5, 7, 8, 10 and 13, Z is O or S, L is any one of the following chemical formulas L-1, L-3, and L-4, R 1 and R 2 are each independently hydrogen, a phenyl group, a biphenyl group or a dibenzothiophenyl group, each of which may be unsubstituted or substituted with a pyridinyl group, R 3 and R 4 One of them is a cyano group, the other is a hydrogen or phenyl group, and the R 3 and R 4 In the case where each is a phenyl group, the above R 3 and R 4 It can form a substituted ring and a condensed ring, a is 1, b is 0, c is 0 and d is 1 or 2. [Chemical formula L-1] [Chemical formula L-3] [Chemical formula L-4] 7. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound which is any one of the following compounds 1-1 to 1-180, compounds 2-1 to 2-180, and compounds 3-1 to 3-30.

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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