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

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2023-0185679, filed December 19, 2023, the entire contents of which are incorporated herein by reference.

[0003] Technology field

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

[0005]

[0006] Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices has continued, leading to blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic EL device with a laminated structure divided into functional layers of a hole layer and a light-emitting layer. Since then, in order to create high-efficiency, long-life organic EL devices, development has been made by introducing characteristic organic material layers within the device, which has led to the development of specialized materials used therefor.

[0007] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic material layer can be classified according to their function, such as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0008] The luminescent materials in organic electroluminescent devices can be categorized into blue, green, and red luminescent materials based on their emission color. Additionally, yellow and orange luminescent materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as luminescent materials to increase color purity and luminescence efficiency through energy transfer.

[0009] Dopant materials can be divided into fluorescent dopants, which utilize organic materials, and phosphorescent dopants, which utilize metal complexes containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescent materials. Therefore, extensive research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

[0010] Up to now, NPB, BCP, Alq3, etc., shown below, are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as materials for light-emitting layers. In particular, among light-emitting layer materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., shown below, which have advantages in terms of improving efficiency, are being used as phosphorescent dopant materials for blue, green, and red, and 4,4-dicarbazolybiphenyl (CBP), shown below, is being used as a phosphorescent host material.

[0011]

[0012] In this way, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not satisfactory in terms of the lifespan of organic electroluminescent devices.

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

[0014] Prior art literature

[0015] Republic of Korea Patent Publication No. 10-2480942

[0016]

[0017] The present invention aims to provide a novel compound that can be used as an organic layer material of an organic electroluminescent device having excellent electron injection / transport capability, electrochemical stability, and thermal stability, specifically, an electron transport layer material and an electron transport auxiliary layer material, and a use thereof.

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

[0019] 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.

[0020]

[0021] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0022] An organic light-emitting compound represented by the following chemical formula 1:

[0023] [Chemical Formula 1]

[0024]

[0025] In the above chemical formula 1,

[0026] X1 to X3 are each independently N or CR, and at least one of X1 to X3 is N,

[0027] X4 to X6 are each independently N or CR, and at least one of X4 to X6 is N,

[0028] R is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0029] Ar1 to Ar4 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0030] L1 and L2 are each independently a single bond, an arylene group having 6 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0031] m and n are each independently integers from 0 to 2, provided that m+n ≥ 2,

[0032] l is an integer from 1 to 3.

[0033] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0034] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0035]

[0036] The organic light-emitting compound according to the present invention has excellent electron injection and transfer capabilities due to its molecular structure, which includes an azine group, which is a strong electron acceptor, and thus the driving voltage of the device can be improved by improving the electron transfer capability to the light-emitting layer.

[0037] In addition, the organic light-emitting compound according to the present invention has a structure in which a biphenyl group to which a cyano group that increases a dipole moment is bonded is located at the center of the structure, and an azine moiety having excellent electron transport ability and stability is connected to both sides of the biphenyl group by a phenyl linker, thereby having excellent electron injection / transport ability, electrochemical stability, and thermal stability.

[0038] In addition, an organic electroluminescent device including an organic light-emitting compound according to the present invention can achieve a low driving voltage and can have significantly improved light-emitting performance, lifespan, and efficiency, and thus can be more effectively applied to full-color display panels, etc.

[0039] 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.

[0040]

[0041] 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.

[0042] 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.

[0043] 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.

[0044] Hereinafter, embodiments of the present invention will be described in detail.

[0045] 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.

[0046] In the present invention, the term “aryl group” may mean a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may refer to, for example, a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a 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. Additionally, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon.

[0047] In the present invention, the term "heteroaryl group" may mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a naphthyridyl group, an acenaphthopyridyl group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, purinyl group, indazolyl group, quinolyl group, benzoquinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group,Nitrogen-containing heteroaryl groups including an acridinyl group, a phenanthridyl group, a carbazolyl group, a phenanthrolinyl group, a phenazinyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a pyrazolopyridyl group, a heptaazaphenalenyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples thereof include oxygen-containing heteroaryl groups such as a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzonaphthofuranyl group, an oxanthrenyl group, a xanthenyl group, and a benzoxanthenyl group; oxygen and sulfur-containing complex heteroaryl groups such as a thiadiazolyl group, an oxadiazolyl group, a phenoxathiinyl group, a benzothienopyrimidinyl group, and a benzofuropyridyl group. Also, the term "heteroarylene group" refers to heteroatoms such as nitrogen (N), sulfur (S), oxygen (O), phosphorus (P),It may refer to a divalent functional group derived from an aromatic hydrocarbon containing at least one of selenium (Se) and silicon (Si). In the heteroaryl group and heteroarylene group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may refer to the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heteroaryl group and heteroarylene group may have a number of nuclear atoms of 5 to 60, 5 to 30, or 5 to 20, respectively.

[0048] 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.

[0049] 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.

[0050] 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.

[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 "haloalkyl group" may mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of the aforementioned alkyl group is substituted with a halogen atom. Here, the halogen atom may be at least one of F, Cl, Br, and I.

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

[0055] In the present invention, the terms “alkylamine group” and “arylamine group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of an amine is substituted with the aforementioned alkyl group or aryl group.

[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 or aryl group.

[0057] In the present invention, the term “arylphosphine group” may mean a monovalent functional group derived from a compound in which the aforementioned aryl group is substituted on phosphine.

[0058] In the present invention, the terms “alkylphosphine oxide group” and “arylphosphine oxide group” may each mean a monovalent functional group derived from a compound in which the aforementioned alkyl group or aryl group is substituted on a phosphine oxide.

[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 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclear atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, It means being substituted with one or more substituents selected from the group consisting of an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a halogen group, a cyano group, and a hydroxy 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.

[0063] [Chemical Formula 1]

[0064]

[0065] In the above chemical formula 1,

[0066] X1 to X3 are each independently N or CR, and at least one of X1 to X3 is N,

[0067] X4 to X6 are each independently N or CR, and at least one of X4 to X6 is N,

[0068] R is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0069] Ar1 to Ar4 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted.

[0070] L1 and L2 are each independently a single bond, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, or a heteroarylene group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0071] m and n are each independently integers from 0 to 2, provided that m+n ≥ 2,

[0072] l is an integer from 1 to 3.

[0073] In one embodiment, m is 0 and n is 2.

[0074] In one embodiment, m is 2 and n is 0.

[0075] In one embodiment, m is 1 and n is 1.

[0076] In one embodiment, m is 1 and n is 2.

[0077] In one embodiment, m is 2 and n is 1.

[0078] In one embodiment, m is 2 and n is 2.

[0079] In one implementation, if m is 0, L1 does not exist, It may mean that a biphenyl group substituted with a moiety and a cyano group (CN) is single bonded.

[0080] In one implementation, when n is 0, L2 does not exist, It may mean that a biphenyl group substituted with a moiety and a cyano group (CN) is single bonded.

[0081] Specifically, one or more groups of hydrogen atoms, alkyl groups, aryl groups, arylene groups, heteroaryl groups and heteroarylene groups that may be present in R, Ar1 to Ar4, L1 and L2 are each independently unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclear atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, or a It means being substituted with one or more substituents selected from the group consisting of an arylsilyl group, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a halogen group, a cyano group, and a hydroxy group, and when substituted with multiple substituents, they may be the same or different from each other.

[0082]

[0083] In one embodiment, in the chemical formula 1,

[0084] X1 to X3 are each independently N or CR, and at least one of X1 to X3 is N,

[0085] X4 to X6 are each independently N or CR, and at least one of X4 to X6 is N,

[0086] R is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms,

[0087] Ar1 to Ar4 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which is unsubstituted or deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclear atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, a heteroaryl group having 1 to 20 carbon atoms, It may be substituted with an alkylsilyl group, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a halogen group, a cyano group or a hydroxy group,

[0088] L1 and L2 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, or a heteroarylene group having 5 to 30 nuclear atoms,

[0089] m and n are each independently integers from 0 to 2, provided that m+n ≥ 2,

[0090] l can be an integer from 1 to 3.

[0091]

[0092] In one embodiment, in the chemical formula 1,

[0093] X1 to X3 are each independently N or CH, and two or more of the above X1 to X3 are N,

[0094] X4 to X6 are each independently N or CH, and two or more of the above X4 to X6 are N,

[0095] Ar1 to Ar4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which may be unsubstituted or substituted with a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a halogen group, a cyano group, or a hydroxy group.

[0096] L1 and L2 are each independently an arylene group having 6 to 30 carbon atoms,

[0097] m and n are each independently integers from 0 to 2, provided that m+n ≥ 2,

[0098] l can be an integer between 1 and 2.

[0099]

[0100] In one embodiment, the chemical formula 1 may be represented by any one selected from the following chemical formulas 2 to 4.

[0101] [Chemical Formula 2]

[0102]

[0103] [Chemical Formula 3]

[0104]

[0105] [Chemical Formula 4]

[0106]

[0107] In each of the above chemical formulas 2 to 4,

[0108] X1 to X3 are each independently N or CH, and two or more of the above X1 to X3 are N,

[0109] X4 to X6 are each independently N or CH, and two or more of the above X4 to X6 are N,

[0110] Ar1 to Ar4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which may be unsubstituted or substituted with a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a halogen group, a cyano group, or a hydroxy group.

[0111]

[0112] In one embodiment, each of Ar1 to Ar4 in the above chemical formula 1 may be any one selected from the following chemical formulas Ar-1 to Ar-23.

[0113] [Chemical formula Ar-1]

[0114]

[0115] [Chemical formula Ar-2]

[0116]

[0117] [Chemical formula Ar-3]

[0118]

[0119] [Chemical formula Ar-4]

[0120]

[0121] [Chemical formula Ar-5]

[0122]

[0123] [Chemical formula Ar-6]

[0124]

[0125] [Chemical formula Ar-7]

[0126]

[0127] [Chemical formula Ar-8]

[0128]

[0129] [Chemical formula Ar-9]

[0130]

[0131] [Chemical formula Ar-10]

[0132]

[0133] [Chemical formula Ar-11]

[0134]

[0135] [Chemical formula Ar-12]

[0136]

[0137] [Chemical formula Ar-13]

[0138]

[0139] [Chemical formula Ar-14]

[0140]

[0141] [Chemical formula Ar-15]

[0142]

[0143] [Chemical formula Ar-16]

[0144]

[0145] [Chemical formula Ar-17]

[0146]

[0147] [Chemical formula Ar-18]

[0148]

[0149] [Chemical formula Ar-19]

[0150]

[0151] [Chemical formula Ar-20]

[0152]

[0153] [Chemical formula Ar-21]

[0154]

[0155] [Chemical formula Ar-22]

[0156]

[0157] [Chemical formula Ar-23]

[0158]

[0159] In each of the above chemical formulas Ar-1 to Ar-23, * represents a site bonded to the above chemical formula 1.

[0160] In one embodiment, each of Ar1 to Ar4 in the above chemical formula 1 may be any one selected from the following chemical formulas Ar-1 to Ar-4.

[0161]

[0162] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one selected from compounds 001 to 242 below.

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] As a specific example, the compound represented by the above chemical formula 1 may be any one selected from the above compounds 005, 013, 021, 049, 053, 065, 093, 099, 157, 163, 206, 214, 222 and 230.

[0225] The organic light-emitting compound according to the present invention has a structure in which a biphenyl group having a cyano group that increases a dipole moment is bonded to the center of the structure, and an azine moiety having excellent electron transport ability and stability is connected to both sides of the biphenyl group by a phenyl linker, thereby having excellent electron injection / transport ability, electrochemical stability, and thermal stability.

[0226] In addition, by using the novel organic light-emitting compound according to the present invention as an organic layer material such as an electron transport layer and an electron transport auxiliary layer, it is possible to realize excellent performance in terms of driving voltage, emission peak, and current efficiency of an organic electroluminescent device.

[0227]

[0228] Organic electroluminescent devices

[0229] 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.

[0230] 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.

[0231] anode

[0232] 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.

[0233] 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.

[0234] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. The anode can be formed, for example, by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0235] cathode

[0236] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0237] 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.

[0238] luminescent layer

[0239] 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.

[0240] 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.

[0241] 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.

[0242] electron transport region

[0243] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0244] 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.

[0245] 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.

[0246] The electron transport layer may include the organic luminescent compound according to the present invention described above. In addition, by using the novel organic luminescent compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be realized.

[0247] 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.

[0248] 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).

[0249] electron transport auxiliary layer

[0250] 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.

[0251] The above electron transport auxiliary layer may include the organic luminescent compound according to the present invention described above. In addition, by using the novel organic luminescent compound according to the present invention as an electron transport auxiliary layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be realized.

[0252] 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.

[0253] hole transport region

[0254] 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.

[0255] 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.

[0256] 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.

[0257] The above hole-injecting material may be any hole-injecting material known in the art without limitation. Non-limiting examples of usable hole-injecting materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,Ndiphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), etc. It can be used alone or in combination of two or more types.

[0258] 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.

[0259] 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).

[0260] hole transport auxiliary layer

[0261] The organic electroluminescent device of the present invention may further include a hole transport auxiliary layer disposed between the hole transport region and the light-emitting layer. The hole transport auxiliary layer serves to transport holes moving from the hole transport region to the light-emitting layer, and also serves to control the thickness of the organic layer. The hole transport auxiliary layer has a high LUMO value, which prevents electrons from moving to the hole transport layer, and has a high triplet (T1) energy, which prevents excitons of the light-emitting layer from diffusing to the hole transport layer.

[0262] Such a hole transport auxiliary layer may include a hole transport material and may be made of the same material as the hole transport region. Furthermore, the hole transport auxiliary layers of red, green, and blue organic light-emitting devices may be made of the same material.

[0263] The hole transport auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives may be used. In addition, the hole transport auxiliary layer may optionally include a p-type dopant in addition to the aforementioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field may be used.

[0264] capping layer

[0265] 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.

[0266] 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).

[0267] 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.

[0268] 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.

[0269]

[0270] 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.

[0271] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0272] 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.

[0273] 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.

[0274]

[0275] 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.

[0276]

[0277] [Preparation]

[0278] [Preparation Example 1]: Synthesis of compound K01

[0279]

[0280] 1-bromo-2-chloro-4-iodobenzene (30.0 g, 94.5 mmol), (4-cyanophenyl)boronic acid (13.9 g, 94.5 mmol), Pd(PPh3)4 (3.3 g, 2.8 mmol), and K2CO3 (39.2 g, 283.6 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound K01 (4'-bromo-3'-chloro-[1,1'-biphenyl]-4-carbonitrile) (22.7 g, 77.5 mmol, yield 82%).

[0281] Mass: [(M+H) + ] :294

[0282]

[0283] [Preparation Example 2]: Synthesis of compound S01

[0284]

[0285] 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine(30.0 g, 68.9 mmol), 1-bromo-4-chlorobenzene(13.2 g, 68.9 mmol), Pd(PPh3)4(2.4 g, 2.1 mmol), and K2CO3(28.6 g, 206.7 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfate, and purified by column chromatography to obtain compound S01 (2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine) (24.6 g, 58.6 mmol, yield 85%).

[0286] Mass: [(M+H) + ] :421

[0287]

[0288] [Preparation Example 3]: Synthesis of compound S02

[0289]

[0290] 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine(30.0 g, 68.9 mmol), 1-bromo-2-chlorobenzene(13.2 g, 68.9 mmol), Pd(PPh3)4(2.4 g, 2.1 mmol), and K2CO3(28.6 g, 206.7 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S02 (2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine) (24.0 g, 57.2 mmol, yield 83%).

[0291] Mass: [(M+H) + ] :421

[0292]

[0293] [Preparation Example 4]: Synthesis of compound S03

[0294]

[0295] 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine(30.0 g, 68.9 mmol), 1-bromo-2-chlorobenzene(13.2 g, 68.9 mmol), Pd(PPh3)4(2.4 g, 2.1 mmol), and K2CO3(28.6 g, 206.7 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S03 (2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine) (24.3 g, 57.9 mmol, yield 84%).

[0296] Mass: [(M+H) + ] :421

[0297]

[0298] [Preparation Example 5]: Synthesis of compound S04

[0299]

[0300] 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (30.0 g, 99.3 mmol), dibenzo[b,d]furan-2-ylboronic acid (21.0 g, 99.3 mmol), Pd(PPh3)4 (3.4 g, 3.0 mmol), and K2CO3 (41.2 g, 297.9 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S04 (2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine) (36.2 g, 83.4 mmol, yield 84%).

[0301] Mass: [(M+H) + ] :435

[0302]

[0303] [Preparation Example 6]: Synthesis of compound S05

[0304]

[0305] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (30.0 g, 94.4 mmol), (2-chlorophenyl)boronic acid (14.8 g, 94.4 mmol), Pd(PPh3)4 (3.3 g, 2.8 mmol), and K2CO3 (39.1 g, 283.2 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfate, and purified by column chromatography to obtain compound S05 (2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine) (30.5 g, 77.4 mmol, yield 82%).

[0306] Mass: [(M+H) + ] :395

[0307]

[0308] [Preparation Example 7]: Synthesis of compound S06

[0309]

[0310] 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (30.0 g, 87.3 mmol), (2-chlorophenyl)boronic acid (13.6 g, 87.3 mmol), Pd(PPh3)4 (3.0 g, 2.6 mmol), and K2CO3 (36.2 g, 261.8 mmol) were added to a mixed solvent of 300 ml of toluene, 45.0 ml of ethanol, and 45.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound S06 (2-([1,1'-biphenyl]-3-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine) (30.4 g, 72.4 mmol, yield 83%).

[0311] Mass: [(M+H) + ] :421

[0312]

[0313] [Preparation Example 8]: Synthesis of Compound A01

[0314]

[0315] Compound S01 (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) synthesized by the method of Preparation Example 2 were added to 200 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A01 (2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine)(20.0 g, 39.1 mmol, yield 82%).

[0316] Mass: [(M+H) + ] :512

[0317]

[0318] [Preparation Example 9]: Synthesis of Compound A02

[0319]

[0320] Compound S02 (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) synthesized by the method of Preparation Example 3 were added to 200 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A02 (2,4-diphenyl-6-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine)(20.2 g, 39.1 mmol, yield 83%).

[0321] Mass: [(M+H) + ] :512

[0322]

[0323] [Preparation Example 10]: Synthesis of Compound A03

[0324]

[0325] Compound S03 (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) synthesized by the method of Preparation Example 4 were added to 200 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A03 (2,4-diphenyl-6-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine)(20.0 g, 39.1 mmol, yield 82%).

[0326] Mass: [(M+H) + ] :512

[0327]

[0328] [Preparation Example 11]: Synthesis of Compound A04

[0329]

[0330] Compound S04 (20.0 g, 46.1 mmol), bis(pinacolato)diboron (15.2 g, 59.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.3 g, 2.8 mmol), and KOAc (9.0 g, 92.2 mmol) synthesized by the method of Preparation Example 5 were added to 200 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A04 (2-(dibenzo[b,d]furan-2-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine) (20.1 g, 38.3 mmol, yield 83%).

[0331] Mass: [(M+H) + ] :526

[0332]

[0333] [Preparation Example 12]: Synthesis of Compound A05

[0334]

[0335] Compound S05 (20.0 g, 50.8 mmol), bis(pinacolato)diboron (16.8 g, 66.0 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), X-Phos (1.5 g, 3.0 mmol), and KOAc (10.0 g, 101.6 mmol) synthesized by the method of Preparation Example 6 were added to 200 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A05 (2-(naphthalen-2-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine) (20.2 g, 41.6 mmol, yield 82%).

[0336] Mass: [(M+H) + ] :486

[0337]

[0338] [Preparation Example 13]: Synthesis of Compound A06

[0339]

[0340] Compound S06 (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) synthesized by the method of Preparation Example 7 were added to 200 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound A06 (2-([1,1'-biphenyl]-3-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine) (20.5 g, 40.0 mmol, yield 84%).

[0341] Mass: [(M+H) + ] :512

[0342]

[0343] [Preparation Example 14]: Synthesis of Compound B01

[0344]

[0345] Compound K01 (20.0 g, 68.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (29.8 g, 68.4 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B01 (3'-chloro-3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile) (30.3 g, 58.1 mmol, yield 85%).

[0346] Mass: [(M+H) + ] :522

[0347]

[0348] [Preparation Example 15]: Synthesis of Compound B02

[0349]

[0350] Compound K01 (20.0 g, 68.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (29.8 g, 68.4 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B02 (3'-chloro-2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile) (30.3 g, 58.1 mmol, yield 85%).

[0351] Mass: [(M+H) + ] :522

[0352]

[0353] [Preparation Example 16]: Synthesis of Compound B03

[0354]

[0355] Compound K01 (20.0 g, 68.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (29.8 g, 68.4 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B03 (3'-chloro-4''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile) (30.3 g, 58.1 mmol, yield 85%).

[0356] Mass: [(M+H) + ] :522

[0357]

[0358] [Preparation Example 17]: Synthesis of Compound B04

[0359]

[0360] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A01 (35.0 g, 68.4 mmol) synthesized by the method of Preparation Example 8, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B04 (3'-chloro-3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1'':4'',1'''-quaterphenyl]-4-carbonitrile) (34.3 g, 57.4 mmol, yield 84%).

[0361] Mass: [(M+H) + ] :598

[0362]

[0363] [Preparation Example 18]: Synthesis of Compound B05

[0364]

[0365] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A02 (35.0 g, 68.4 mmol) synthesized by the method of Preparation Example 9, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B05 (2''-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile) (34.3 g, 57.4 mmol, yield 84%).

[0366] Mass: [(M+H) + ] :598

[0367]

[0368] [Preparation Example 19]: Synthesis of Compound B06

[0369]

[0370] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A03 (35.0 g, 68.4 mmol) synthesized by the method of Preparation Example 10, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B06 (2''-chloro-3-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile) (33.9 g, 56.7 mmol, yield 83%).

[0371] Mass: [(M+H) + ] :598

[0372]

[0373] [Preparation Example 20]: Synthesis of Compound B07

[0374]

[0375] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A04 (35.9 g, 68.4 mmol) synthesized by the method of Preparation Example 11, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B07 (3'-chloro-2''-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile) (34.7 g, 56.7 mmol, yield 83%).

[0376] Mass: [(M+H) + ] :612

[0377]

[0378] [Preparation Example 21]: Synthesis of Compound B08

[0379]

[0380] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A05 (33.2 g, 68.4 mmol) synthesized by the method of Preparation Example 12, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B08 (3'-chloro-2''-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile)(33.2 g, 58.1 mmol, yield 85%).

[0381] Mass: [(M+H) + ] :572

[0382]

[0383] [Preparation Example 22]: Synthesis of Compound B09

[0384]

[0385] Compound K01 (20.0 g, 68.4 mmol) synthesized by the method of Preparation Example 1, compound A06 (35.0 g, 68.4 mmol) synthesized by the method of Preparation Example 13, Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.3 g, 205.1 mmol) were added to a mixed solvent of 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound B09 (2''-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-3'-chloro-[1,1':4',1''-terphenyl]-4-carbonitrile) (34.3 g, 57.4 mmol, yield 84%).

[0386] Mass: [(M+H) + ] :598

[0387]

[0388] [Preparation Example 23]: Synthesis of compound C01

[0389]

[0390] Compound B04 (25.0 g, 41.4 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) synthesized by the method of Preparation Example 17 were added to 250 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C01 (3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1'':4'',1'''-quaterphenyl]-4-carbonitrile) (23.6 g, 34.3 mmol, yield 82%).

[0391] Mass: [(M+H) + ] :690

[0392]

[0393] [Preparation Example 24]: Synthesis of compound C02

[0394]

[0395] Compound B05 (25.0 g, 41.9 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) synthesized by the method of Preparation Example 18 were added to 250 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C02 (2-(4,6-diphenyl-1,3,5-triazin-2-yl)-2''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile) (23.9 g, 34.8 mmol, yield 83%).

[0396] Mass: [(M+H) + ] :690

[0397]

[0398] [Preparation Example 25]: Synthesis of compound C03

[0399]

[0400] Compound B06 (25.0 g, 41.9 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) synthesized by the method of Preparation Example 19 were added to 250 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C03 (3-(4,6-diphenyl-1,3,5-triazin-2-yl)-2''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile) (23.6 g, 34.3 mmol, yield 82%).

[0401] Mass: [(M+H) + ] :690

[0402]

[0403] [Preparation Example 26]: Synthesis of compound C04

[0404]

[0405] Compound B07 (25.0 g, 40.9 mmol), bis(pinacolato)diboron (13.5 g, 53.2 mmol), Pd(dppf)Cl2 (0.9 g, 1.2 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.0 g, 81.8 mmol) synthesized by the method of Preparation Example 20 were added to 250 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C04(2''-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile)(28.7 g, 40.9 mmol, yield 83%).

[0406] Mass: [(M+H) + ] :704

[0407]

[0408] [Preparation Example 27]: Synthesis of compound C05

[0409]

[0410] Compound B08 (25.0 g, 43.8 mmol), bis(pinacolato)diboron (14.5 g, 56.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.3 mmol), X-Phos (1.3 g, 2.6 mmol), and KOAc (8.6 g, 87.6 mmol) synthesized by the method of Preparation Example 21 were added to 250 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C05(2''-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile)(23.8 g, 35.9 mmol, yield 82%).

[0411] Mass: [(M+H) + ] :664

[0412]

[0413] [Preparation Example 28]: Synthesis of compound C06

[0414]

[0415] Compound B09 (25.0 g, 41.9 mmol), bis(pinacolato)diboron (13.8 g, 54.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.5 mmol), and KOAc (8.2 g, 83.7 mmol) synthesized by the method of Preparation Example 22 were added to 250 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain compound C06(2''-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile)(24.2 g, 35.2 mmol, yield 84%).

[0416] Mass: [(M+H) + ] :690

[0417]

[0418] [Synthesis example]

[0419] [Synthesis Example 1]: Synthesis of Compound 005

[0420]

[0421] Compound B01 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 14, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 005 (3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile) (24.7 g, 31.1 mmol, yield 81%).

[0422] Mass: [(M+H) + ] : 795

[0423]

[0424] [Synthesis Example 2]: Synthesis of Compound 013

[0425]

[0426] Compound B02 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 15, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 013(2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(24.7 g, 31.1 mmol, yield 81%).

[0427] Mass: [(M+H) + ] : 795

[0428]

[0429] [Synthesis Example 3]: Synthesis of Compound 021

[0430]

[0431] Compound B03 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 16, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 021(4''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(25.0 g, 31.5 mmol, yield 82%).

[0432] Mass: [(M+H) + ] : 795

[0433]

[0434] [Synthesis Example 4]: Synthesis of Compound 049

[0435]

[0436] Compound B02 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 15, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 049(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile(25.3 g, 31.9 mmol, yield 83%).

[0437] Mass: [(M+H) + ] : 795

[0438]

[0439] [Synthesis Example 5]: Synthesis of Compound 053

[0440]

[0441] Compound B03 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 16, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 053(2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(24.4 g, 30.7 mmol, yield 80%).

[0442] Mass: [(M+H) + ] : 795

[0443]

[0444] [Synthesis Example 6]: Synthesis of Compound 065

[0445]

[0446] Compound C01 (20.0 g, 29.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.0 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.0 g, 87.1 mmol), synthesized by the method of Preparation Example 23, were added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 065 (3',3'''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1'':4'',1'''-quaterphenyl]-4-carbonitrile) (18.2 g, 22.9 mmol, yield 79%).

[0447] Mass: [(M+H) + ] :795

[0448]

[0449] [Synthesis Example 7]: Synthesis of Compound 093

[0450]

[0451] Compound C02 (20.0 g, 29.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.0 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol) and K2CO synthesized by the method of Preparation Example 24 3(12.0 g, 87.1 mmol) was added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and refluxing for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 093 (2,2''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile)(18.7 g, 23.5 mmol, yield 81%).

[0452] Mass: [(M+H) + ] :795

[0453]

[0454] [Synthesis Example 8]: Synthesis of Compound 099

[0455]

[0456] Compound C03 (20.0 g, 29.0 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.3 g, 29.0 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.0 g, 87.1 mmol), synthesized by the method of Preparation Example 25, were added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 099 (3-(4,6-diphenyl-1,3,5-triazin-2-yl)-2''-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile) (20.7 g, 23.8 mmol, yield 82%).

[0457] Mass: [(M+H) + ] :871

[0458]

[0459] [Synthesis Example 9]: Synthesis of Compound 157

[0460]

[0461] Compound B02 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 15, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 157 (4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3''-(2,6-diphenylpyrimidin-4-yl)-[1,1':3',1''-terphenyl]-4-carbonitrile) (24.4 g, 30.7 mmol, yield 80%).

[0462] Mass: [(M+H) + ] : 794

[0463]

[0464] [Synthesis Example 10]: Synthesis of Compound 163

[0465]

[0466] Compound B01 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 14, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 163 (2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile) (24.0 g, 30.3 mmol, yield 79%).

[0467] Mass: [(M+H) + ] : 794

[0468]

[0469] [Synthesis Example 11]: Synthesis of Compound 206

[0470]

[0471] Compound B02 (20.0 g, 38.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (16.7 g, 38.4 mmol), Pd(OAc)2 (0.3 g, 1.2 mmol), Xphos (1.1 g, 2.3 mmol), and Cs2CO3 (25.0 g, 76.8 mmol), synthesized by the method of Preparation Example 15, were added to a mixed solvent of 240 ml of toluene, 40 ml of EtOH, and 40 ml of water, and reacted while heating and stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 206 (3''-(2,6-diphenylpyrimidin-4-yl)-4'-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile) (24.3 g, 30.7 mmol, yield 80%).

[0472] Mass: [(M+H) + ] : 793

[0473]

[0474] [Synthesis Example 12]: Synthesis of Compound 214

[0475]

[0476] Compound C04 (20.0 g, 28.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.1 g, 28.5 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (11.8 g, 85.4 mmol), synthesized by the method of Preparation Example 26, were added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 214(4'-(2-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(19.6 g, 22.2 mmol, yield 78%).

[0477] Mass: [(M+H) + ] :885

[0478]

[0479] [Synthesis Example 13]: Synthesis of Compound 222

[0480]

[0481] Compound C05 (20.0 g, 30.2 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.7 g, 30.2 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.5 g, 90.6 mmol), synthesized by the method of Preparation Example 27, were added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 222 (3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(19.6 g, 23.2 mmol, yield 77%).

[0482] Mass: [(M+H) + ] :845

[0483]

[0484] [Synthesis Example 14]: Synthesis of Compound 230

[0485]

[0486] Compound C06 (20.0 g, 29.0 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.3 g, 29.0 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.0 g, 87.1 mmol), synthesized by the method of Preparation Example 28, were added to a mixed solvent of 200 ml of toluene, 30.0 ml of ethanol, and 30.0 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound 230(4'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-4-carbonitrile)(19.2 g, 22.1 mmol, yield 76%).

[0487] Mass: [(M+H) + ] :871

[0488]

[0489] [Examples and Comparative Examples] - 1

[0490] [Examples 1 to 14 and Comparative Examples 1 to 4]: Fabrication of blue organic electroluminescent devices

[0491] 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.

[0492] 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.

[0493] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing Compound A and Compound B in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing Compound D and Compound E in a weight ratio of 98:2 on the hole transport auxiliary layer to a thickness of 200 Å, the electron transport auxiliary layer was formed by depositing Compound F in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing an electron transport layer material and Compound H in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. The structures of compounds A to H are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0494] Compound A Compound B Compound C Compound D Compound E Compound F Compound G Compound H

[0495] Electron transport layer material Example 1 Compound 005 Example 2 Compound 013 Example 3 Compound 021 Example 4 Compound 049 Example 5 Compound 053 Example 6 Compound 065 Example 7 Compound 093 Example 8 Compound 099 Example 9 Compound 157 Example 10 Compound 163 Example 11 Compound 206 Example 12 Compound 214 Example 13 Compound 222 Example 14 Compound 230 Comparative Example 1 Compound I Comparative Example 2 Compound J Comparative Example 3 Compound K Comparative Example 4 Compound L

[0496]

[0497] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 14 and Comparative Examples 1 to 4

[0498] For the organic electroluminescent devices manufactured in Examples 1 to 14 and Comparative Examples 1 to 4, the driving voltage, luminescence (EL) peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 3 below.

[0499] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 13.44538.8 Example 23.64548.6 Example 33.44538.5 Example 43.44528.9 Example 53.54518.5 Example 63.64548.5 Example 73.74538.6 Example 83.54558.7 Example 93.74528.7 Example 103.74538.7 Example 113.84568.6 Example 123.54538.9 Example 133.74538.8 Example 143.64558.6 Comparative Example 14.54557.5 Comparative Example 24.24547.9 Comparative Example 34.44557.3 Comparative Example 44.34557.4

[0500] Referring to Table 3 above, the blue organic electroluminescent devices manufactured in Examples 1 to 14 using the compounds according to the present invention as electron transport layer materials showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices manufactured in Comparative Examples 1 to 4 using compounds I to L as electron transport layer materials.

[0501] Specifically, the organic light-emitting compound according to the present invention used in the blue organic electroluminescent device of Examples 1 to 14 has a structure in which a biphenyl group having a cyano group bonded to increase a dipole moment and an azine moiety having excellent electron transport ability and stability are connected by a phenyl linker, so that the blue organic electroluminescent device of Comparative Example 1, in which a compound having dual azine moieties and biphenyl groups bonded and not including a cyano group is used in the electron transport layer, like Compound I, or the blue organic electroluminescent device of Comparative Example 2, in which a compound having an azine moiety bonded adjacent to a cyano group and another azine moiety and a biphenyl group bonded, like Compound J, is used in the electron transport layer, or the blue organic electroluminescent device of Comparative Example 3, in which a compound including a cyano group connected by a dual azine moiety and a phenyl linker, like Compound K, is used in the electron transport layer, or the blue organic electroluminescent device of Comparative Example 4, in which a compound having dual azine moieties connected by a phenyl linker and not including a cyano group, like Compound L, is used in the electron transport layer. It was found that it exhibited superior performance in terms of driving voltage and current efficiency compared to light-emitting elements.

[0502]

[0503] [Examples and Comparative Examples] - 2

[0504] [Examples 15 to 17 and Comparative Example 5]: Fabrication of a blue organic electroluminescent device

[0505] 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.

[0506] 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.

[0507] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing Compound A and Compound B in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing Compound D and Compound E in a weight ratio of 98:2 to a thickness of 200 Å on the hole transport auxiliary layer, the electron transport auxiliary layer was formed by depositing an electron transport auxiliary layer material in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing Compound G and Compound H in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. Compounds A to H are as shown in Table 1 above, and the electron transport auxiliary layer materials are shown in Table 4 below.

[0508] Electron transport auxiliary layer material Example 15 Compound 099 Example 16 Compound 214 Example 17 Compound 230 Comparative Example 5 Compound F

[0509]

[0510] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 15 to 17 and Comparative Example 5

[0511] For the organic electroluminescent devices manufactured in Examples 15 to 17 and Comparative Example 5, 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.

[0512] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 153.94547.6 Example 163.84567.9 Example 173.84557.8 Comparative example 54.54567.0

[0513] Referring to Table 5 above, the blue organic electroluminescent devices manufactured in Examples 15 to 17 using the compound according to the present invention as an electron transport layer material showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device manufactured in Comparative Example 5 using compound F as an electron transport auxiliary layer material.

[0514]

[0515] While the embodiments of the present invention have been described above, those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical concept or essential features thereof. Therefore, the embodiments described above should be understood to be illustrative in all respects, not restrictive.

Claims

1. An organic luminescent compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 to X3 are each independently N or CR, and at least one of X1 to X3 is N, X4 to X6 are each independently N or CR, and at least one of X4 to X6 is N, R is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, Ar1 to Ar4 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted. L1 and L2 are each independently a single bond, an arylene group having 6 to 60 carbon atoms or a heteroarylene group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, m and n are each independently an integer from 0 to 2, provided that m+n ≥ 2, l is an integer between 1 and 3.

2. In paragraph 1, The above X1 to X3 are each independently N or CR, and at least one of the above X1 to X3 is N, The above X4 to X6 are each independently N or CR, and at least one of the above X4 to X6 is N, The above R is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, The above Ar1 to Ar4 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, It may be substituted with an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a halogen group, a cyano group or a hydroxy group, The above L1 and L2 are each independently a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, The above m and n are each independently an integer from 0 to 2, provided that m+n ≥ 2, An organic luminescent compound wherein l is an integer from 1 to 3.

3. In paragraph 1, The above X1 to X3 are each independently N or CH, and at least two of the above X1 to X3 are N, The above X4 to X6 are each independently N or CH, and at least two of the above X4 to X6 are N, The above Ar1 to Ar4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a halogen group, a cyano group or a hydroxy group. The above L1 and L2 are each independently an arylene group having 6 to 30 carbon atoms, The above m and n are each independently an integer from 0 to 2, provided that m+n ≥ 2, An organic luminescent compound wherein l is an integer from 1 to 2.

4. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by any one selected from the following chemical formulas 2 to 4: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] In each of the above chemical formulas 2 to 4, X1 to X3 are each independently N or CH, and at least two of X1 to X3 are N, X4 to X6 are each independently N or CH, and at least two of said X4 to X6 are N, Ar1 to Ar4 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, each of which may be unsubstituted or substituted with a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a halogen group, a cyano group, or a hydroxy group.

5. In paragraph 1, Each of the above Ar1 to Ar4 is an organic light-emitting compound selected from the following chemical formulas Ar-1 to Ar-23: [Chemical formula Ar-1] [Chemical formula Ar-2] [Chemical formula Ar-3] [Chemical formula Ar-4] [Chemical formula Ar-5] [Chemical formula Ar-6] [Chemical formula Ar-7] [Chemical formula Ar-8] [Chemical formula Ar-9] [Chemical formula Ar-10] [Chemical formula Ar-11] [Chemical formula Ar-12] [Chemical formula Ar-13] [Chemical formula Ar-14] [Chemical formula Ar-15] [Chemical formula Ar-16] [Chemical formula Ar-17] [Chemical formula Ar-18] [Chemical formula Ar-19] [Chemical formula Ar-20] [Chemical formula Ar-21] [Chemical formula Ar-22] [Chemical formula Ar-23] In each of the chemical formulas Ar-1 to Ar-23, * represents a site bonded to the chemical formula 1.

6. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound selected from compounds 001 to 242 below.

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

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

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

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

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

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