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. The present invention can achieve excellent performance with low driving voltage, high luminous efficiency, and improved lifetime.

Description

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

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0182589 filed on December 10, 2024, and all contents disclosed in the document of said Korean Patent Application are incorporated herein as part of this specification.

[0003] Technology field

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

[0005] Research on organic electroluminescent (EL) devices has continued since Bernanose’s observation of organic thin-film luminescence in the 1950s, leading to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic electroluminescent device with a stacked structure divided into a hole layer and a functional layer for the emissive layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has progressed by introducing distinct organic layers within the device, leading to the development of specialized materials used for this purpose.

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

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

[0008] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since the development of these phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, a lot of research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

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

[0010] As such, while conventional organic layer materials have advantages in terms of luminescence characteristics, they do not meet satisfactory standards in terms of the lifespan of organic electroluminescent devices because their low glass transition temperature results in very poor thermal stability.

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

[0012]

[0013] Prior art literature

[0014] Korean Published Patent Application No. 10-2020-0019938

[0015]

[0016] The present invention aims to provide a novel compound and its uses that can be used as an organic layer material for an organic electroluminescent device, specifically as an electron transport layer material and an electron transport auxiliary layer material, which has excellent thermal stability, electron injection and transfer capabilities, and luminescence ability.

[0017] In addition, the present invention aims to provide an organic electroluminescent device that includes the novel organic light-emitting compound described above, with significantly improved luminescence performance, driving voltage, lifespan, and efficiency.

[0018] The problems that the present invention aims to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by a person skilled in the art from the description below.

[0019]

[0020] To solve the above-mentioned problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0021] Organic luminescent compound represented by the following chemical formula 1:

[0022] [Chemical Formula 1]

[0023]

[0024] In the above chemical formula 1,

[0025] X1 to X3 are each independently N or CR1, and at least two of X1 to X3 are N, and

[0026] X4 to X6 are each independently N or CR2, and at least two of X4 to X6 are N, and

[0027] Ar1 to Ar4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and

[0028] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0029] R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, It is selected from alkylamine groups having 1 to 20 carbon atoms or arylamine groups having 6 to 30 carbon atoms, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 5 to 20 nuclei.

[0030] In addition, the present invention provides an organic electroluminescent device comprising the above organic light-emitting compound.

[0031] In addition, the present invention provides the use of the above-described organic light-emitting compound in an organic electroluminescent device.

[0032]

[0033] The organic light-emitting compound according to the present invention has dual EWG moiety connected through a biphenyl linker, and an EWG moiety is connected in an ortho orientation on one side of the biphenyl linker to utilize a steric effect, while an EWG moiety is connected in a para orientation on the other side of the biphenyl linker to set an appropriate LUMO level. In addition, the organic light-emitting compound according to the present invention has an asymmetric EWG moiety introduction structure, thereby securing an expanded LUMO distribution, which can improve electron injection and transfer characteristics.

[0034] In addition, an organic electroluminescent device comprising an organic light-emitting compound according to the present invention can have significantly improved performance in terms of driving voltage, emission peak, and current efficiency.

[0035] The effects of the present invention are not limited to those mentioned above, and other unmentioned effects will be clearly understood by a person skilled in the art from the description below.

[0036]

[0037] The advantages and features of the present invention and the methods for achieving them will become clear by referring to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below but can be implemented in various different forms. These embodiments are provided merely 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 only by the scope of the claims.

[0038] The terms used herein are for describing the embodiments and are not intended to limit the invention. In this specification, the singular form includes the plural form unless specifically stated otherwise in the text. As used herein, "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0039] Unless otherwise defined, all terms used herein (including technical and scientific terms) may be used in a meaning commonly understood by those skilled in the art to which the present invention pertains. Additionally, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0040] Hereinafter, embodiments of the present invention will be described in detail.

[0041] Prior to the explanation, the meanings of the terms used in this specification are briefly explained. However, since the explanation of terms is intended to aid in understanding this specification, it should be noted that they are not used to limit the technical scope of the invention unless explicitly stated to be a limiting factor.

[0042] In the present invention, the term "aryl group" may refer to a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may mean, for example, a phenyl group, a naphthyl group, 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, a phenanthrenyl group, and the like, but is not limited thereto.

[0043] In the present invention, the term "arylene group" refers to a structure having one additional substituent to the "aryl group," and may mean a divalent functional group derived from an aromatic hydrocarbon. The arylene group may refer to, for example, a phenylene group, a naphthylene group, anthracenylene group, a biphenylene group, etc., but is not limited thereto.

[0044] In the present invention, the term "heteroaryl group" may refer to a monovalent functional group derived from an aromatic heterocyclic ring of a single ring 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 heteroatoms in addition to carbon atoms. Specific examples of the above heteroaryl groups include: pyrrolyl group, pyridyl group, pyridazinyl group, triazinyl group, pyrimidinyl group, pyrazinyl group, naphthyridyl group, acenaphthopyridyl group, triazolyl group, tetrazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indolyl group, isoindolyl group, indolizinyl group, and purinyl group. 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,A nitrogen-containing heteroaryl group 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.; a sulfur-containing heteroaryl group including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples include oxygen-containing heteroaryl groups including furyl groups, pyranyl groups, benzofuranyl groups, isobenzofuranyl groups, dibenzofuranyl groups, benzonaphthofuranyl groups, oxanthrenyl groups, xanthenyl groups, benzoxanthenyl groups, etc.; oxygen and sulfur complex-containing heteroaryl groups including thiadiazolyl groups, oxadiazolyl groups, phenoxathiinyl groups, benzothienopyrimidinyl groups, and benzofuropyridyl groups. In addition, the term "heteroarylene group" refers to nitrogen (N), sulfur (S), oxygen (O), phosphorus (P) as heteroatoms,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 nuclei may be defined instead of the number of carbon atoms. Here, the number of nuclei may refer to the number of atoms including one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si), in addition to carbon (C) atoms. For example, the heteroaryl group and heteroarylene group may each have a number of nuclei of 5 to 60, 5 to 30, or 5 to 20.

[0045] In the present invention, the term "alkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of a linear or branched structure.The above alkyl group is, 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, 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group, and 3-methylpentyl group.

[0046] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of 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.

[0047] In the present invention, the term "heterocycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of 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. The heterocycloalkyl group may be defined by the number of nuclei instead of the number of carbon atoms. Here, the number of nuclei may refer to the number of atoms including one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) in addition to the carbon (C) atom. For example, the heterocycloalkyl group may have a number of nuclei of 3 to 60, 3 to 30, or 3 to 20.

[0048] In the present invention, the term "alkenyl group" may refer to a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds at the middle or end of an alkyl group.

[0049] In the present invention, the term "alkynyl group" may refer to a monovalent functional group derived from a hydrocarbon containing one or more carbon triple bonds at the middle or end of an alkyl group.

[0050] In the present invention, the term "haloalkyl group" may refer to a monovalent functional group derived from a compound in which a halogen atom is substituted on one or more of the hydrogens of the aforementioned alkyl group. Here, the halogen atom may be one or more of F, Cl, Br, and I.

[0051] In the present invention, the terms "alkylsilyl group" and "arylsilyl group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of a silane are substituted with the aforementioned alkyl group or aryl group.

[0052] In the present invention, the terms "alkylamine group" and "arylamine group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of an amine are substituted with the aforementioned alkyl group or aryl group.

[0053] In the present invention, the terms "alkylboron group" and "arylboron group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of the boran are substituted with the aforementioned alkyl group or aryl group.

[0054] In the present invention, the term "arylphosphine group" may refer to a monovalent functional group derived from a compound in which the aforementioned aryl group is substituted on phosphine.

[0055] In the present invention, the terms "alkylphosphine oxide group" and "arylphosphine oxide group" may each refer to a monovalent functional group derived from a compound in which the aforementioned alkyl group or aryl group is substituted on phosphine oxide.

[0056] In the present invention, the term "substitution" each independently refers to a deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, and a carbon atom having 6 to 30 carbon atoms. It means being substituted with one or more substituents R' selected from the group consisting of an arylphosphine oxide group, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0057]

[0058] Organic light-emitting compounds

[0059] The present invention provides a novel organic light-emitting compound. The organic light-emitting compound is represented by the following chemical formula 1.

[0060] [Chemical Formula 1]

[0061]

[0062] In the above chemical formula 1,

[0063] X1 to X3 are each independently N or CR1, and at least two of X1 to X3 are N, and

[0064] X4 to X6 are each independently N or CR2, and at least two of X4 to X6 are N, and

[0065] Ar1 to Ar4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and

[0066] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0067] R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, It is selected from alkylamine groups having 1 to 20 carbon atoms or arylamine groups having 6 to 30 carbon atoms, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 5 to 20 nuclei.

[0068]

[0069] In one embodiment, in the above formula 1,

[0070] X1 to X3 are each independently N or CR1, and at least two of X1 to X3 are N, and

[0071] X4 to X6 are each independently N or CR2, and at least two of X4 to X6 are N, and

[0072] Ar1 to Ar4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and

[0073] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0074] R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, It is selected from alkylamine groups having 1 to 20 carbon atoms or arylamine groups having 6 to 30 carbon atoms, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 5 to 20 nuclei.

[0075]

[0076] In one embodiment, in the above formula 1,

[0077] X1 to X6 are N, and

[0078] Ar1 to Ar4 are each independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and

[0079] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0080] R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylboron group having 1 to 10 carbon atoms, an arylboron group having 6 to 20 carbon atoms, an arylphosphine group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 1 to 10 carbon atoms, an arylphosphine oxide group having 6 to 20 carbon atoms, It is selected from alkylamine groups having 1 to 10 carbon atoms or arylamine groups having 6 to 20 carbon atoms, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and aryl groups having 6 to 10 carbon atoms.

[0081]

[0082] In one embodiment, in the above formula 1,

[0083] X1 to X6 are N, and

[0084] Ar1 to Ar4 are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, and each may be unsubstituted or substituted with one or more Rs, and

[0085] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0086] R is independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a phenyl group, and a naphthyl group.

[0087]

[0088] In one embodiment, in the above formula 1,

[0089] X1 to X6 are N, and

[0090] Ar1 to Ar4 are each independently selected from a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a carbazolyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a quinolyl group, a quinazolinyl group, a spiro[9H-anthracene-10,9'-fluorene]yl group, a 9,9'-spirobifluorenyl group, a spiro[fluorene-9,9'-xanthen]yl group, or a spiro[benzo][b][1,4]benzoxasiline-10,5'-benzo[b][1]benzosilole]yl group, each of which may be unsubstituted or substituted with one or more Rs, and

[0091] Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different,

[0092] R is independently selected from deuterium, an alkyl group having 1 to 5 carbon atoms, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, or a quinoxazolinyl group, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, a phenyl group, and a naphthyl group.

[0093]

[0094] In one embodiment, in the above formula 1,

[0095] Ar1 to Ar4 are each independently any one of the following chemical formulas 2-1 to 2-14, and each may be unsubstituted or substituted with one or more R, wherein R is as described above.

[0096]

[0097] Y1 and Y2 are each independently O, S, CR3R4 or NR5, and

[0098] Y3 is independently C or Si, and

[0099] R3 to R5 can each be independently selected from hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei.

[0100]

[0101] In one embodiment, in the above formula 1,

[0102] R is each independently any one of the following chemical formulas 3-1 to 3-5, and each may be unsubstituted or substituted with one or more R', and R' is as described above.

[0103]

[0104]

[0105] In one embodiment, the organic light-emitting compound represented by the above formula 1 may be any one selected from the following compounds 1 to 112.

[0106]

[0107]

[0108] As a specific example, the compound represented by the above chemical formula 1 may be any one selected from the compounds 001, 005, 016, 021, 022, 023, 026, 071, 075, 085, 090, 094, 095, 097, 102, 105, 106, 108, and 112.

[0109] The organic light-emitting compound according to the present invention has dual EWG moiety connected through a biphenyl linker, and an EWG moiety is connected in an ortho orientation on one side of the biphenyl linker to utilize a steric effect, while an EWG moiety is connected in a para orientation on the other side of the biphenyl linker to set an appropriate LUMO level. In addition, the organic light-emitting compound according to the present invention has an asymmetric EWG moiety introduction structure, thereby securing an expanded LUMO distribution, which can improve electron injection and transfer characteristics.

[0110] In addition, an organic electroluminescent device comprising an organic light-emitting compound according to the present invention can have significantly improved performance in terms of driving voltage, emission peak, and current efficiency.

[0111]

[0112] Organic Electroluminescent Device

[0113] The present invention provides an organic electroluminescent device comprising the novel organic light-emitting compound described above. The organic light-emitting compound according to the present invention may be included in one or more of the organic layers disposed between the cathode and the anode of the organic electroluminescent device.

[0114] 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.

[0115] anode

[0116] 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.

[0117] The type of the anode material is not specifically limited and can be manufactured according to conventional methods known in the industry. The anode material may be, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); composites of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, etc., and each of these may be used alone or in combination of two or more types.

[0118] The method of manufacturing the above anode is not particularly limited and can be manufactured according to conventional methods known in the industry. The above anode can be formed by coating an anode material on a substrate, such as, for example, a silicon wafer, quartz, a glass plate, a metal plate, and a plastic film.

[0119] cathode

[0120] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into an organic layer.

[0121] The type of cathode material forming the above cathode is not specifically limited and can be manufactured according to conventional methods known in the industry. 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 multilayer structural materials such as LiF / Al or LiO2 / Al.

[0122] light-emitting layer

[0123] 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.

[0124] The light-emitting material forming the above-mentioned light-emitting layer may use various commercially available materials without special restrictions, depending on the desired wavelength of emitted light.

[0125] In one embodiment, the light-emitting material can be classified into blue, green, red, etc., depending on the light emission color. To prevent problems such as reduced color purity or decreased efficiency of the device due to light emission attenuation effects, the light-emitting material can form a light-emitting layer by mixing a host material and a dopant material. The light-emitting efficiency of the light-emitting device can be improved by using a host material, which is the main material forming the light-emitting layer, and a small amount of dopant having a smaller energy band gap compared to the host material.

[0126] Electronic transport area

[0127] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0128] The above electron transport region serves to move electrons injected from the cathode to the light-emitting layer. This electron transport region may include one or more types 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 aforementioned electron transport layer and electron injection layer.

[0129] In the electron transport region above, the electron injection layer can use an electron injection material that facilitates electron injection from the cathode and has high electron mobility without limitation. Non-limiting examples of usable electron injection materials include the above-mentioned anode compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As a specific example, the electron injection material may include one or more selected from the group consisting of lanthanide metals such as LiF, Li2O, BaO, NaCl, CsF; Yb, etc.; and halogenated metals such as RbCl, RbI, etc.

[0130] The electron transport layer described above may include the organic light-emitting compound according to the present invention. In addition, by using the novel organic light-emitting compound according to the present invention as the electron transport layer material, excellent performance can be achieved in terms of driving voltage, emission peak, current efficiency, and lifespan.

[0131] The electron transport layer above can be formed by mixing the organic light-emitting compound according to the present invention with Liq (Lithium quinolate). The conduction band of Liq is 5.58 eV and the valence band is 3.153 eV, which has the effect of lowering the potential barrier.

[0132] The electron transport region can be manufactured using conventional methods known in the relevant technical field. Examples of electron transport regions include, but are not limited to, vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0133] Electron transport auxiliary layer

[0134] 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.

[0135] The electron transport auxiliary layer described above may include the organic light-emitting compound according to the present invention. In addition, by using the novel organic light-emitting compound according to the present invention as the electron transport auxiliary layer material, excellent performance can be achieved in terms of driving voltage, emission peak, and current efficiency.

[0136] As is known in the art, the above electron transport assist layer can be formed by vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., but is not limited thereto.

[0137] Precision transport area

[0138] 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.

[0139] The hole transport region described above may include one or more 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 aforementioned hole injection layer and the hole transport layer.

[0140] The materials forming the hole injection layer and the hole transport layer are not particularly limited as long as they are materials with a low hole injection barrier and high hole mobility, and hole injection materials and hole transport materials used in the industry can be used without limitation. The materials forming the hole injection layer and the hole transport layer may be the same or different from each other.

[0141] The hole injection material mentioned above may be any hole injection material known in the art without limitation. Non-limiting examples of usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,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)). These can be used alone, Or, two or more types can be mixed.

[0142] In addition, the hole transport material mentioned above may be any hole transport material known in the art without limitation. Non-limiting examples of usable hole transport materials include carbazole derivatives such as phenylcarbazole and polyvinylcarbazole; fluorene derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(Ncarbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine) and TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), and these may be used alone or in combination of two or more types.

[0143] The hole transport region described above can be manufactured through conventional methods known in the art. Examples include, but are not limited to, vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0144] Precision transport auxiliary layer

[0145] 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 to control the thickness of the organic layer. This hole transport auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer and has a high triplet (T1) energy to prevent excitons of the light-emitting layer from diffusing into the hole transport layer.

[0146] These hole transport auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the hole transport auxiliary layers of red, green, and blue organic light-emitting diodes may be made of the same material.

[0147] The hole transport assisting 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 assisting layer may optionally include a p-type dopant in addition to the aforementioned materials. As the p-type dopant, known p-type dopants used in the relevant art field may be used.

[0148] capping layer

[0149] The organic electroluminescent device of the present invention may further include a capping layer disposed on the cathode. The capping layer protects the organic light-emitting device while facilitating the efficient emission of light generated from the organic layer to the outside.

[0150] The capping material forming the capping layer may include, for example, one or more 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), and 1,1'-bis(di-4-tolylaminophenyl) cyclohexane (TAPC), but is not limited thereto.

[0151] The capping layer may be a single layer, but may include two or more layers having different refractive indices, so that the refractive index changes gradually as it passes through the two or more layers.

[0152] The above capping layer can be manufactured through conventional methods known in the art, and various methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method can be used.

[0153]

[0154] The present invention provides an application of the above-described organic light-emitting compound in an organic electroluminescent device. Through this, it provides an organic electroluminescent device with significantly improved luminescence performance, driving voltage, lifespan, and efficiency.

[0155] In one embodiment, the organic light-emitting compound may be used as an electron transport material in the organic electroluminescent device.

[0156] 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 for the electron transport region.

[0157] In one embodiment, the organic light-emitting compound may be used as a material for an electron transport region and / or an electron transport auxiliary layer in the organic electroluminescent device.

[0158]

[0159] The present invention will be described in detail below through examples, but the following examples are merely illustrative of the invention and the invention is not limited by the following examples.

[0160]

[0161] [Preparation Example]

[0162]

[0163] [Preparation Example 1] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (A01)

[0164]

[0165] 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 43.6mmol), 2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.4g, 43.6mmol), Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 130.9mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (13.2 g, 31.4 mmol, yield 72%).

[0166] Mass : [(M+H) + ] :421

[0167]

[0168] [Preparation Example 2] Synthesis of 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (A02)

[0169]

[0170] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (15.0g, 47.2mmol), 2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.3g, 47.2mmol), Pd(PPh3)4 (1.6g, 1.4mmol), and K2CO3 (19.6g, 141.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (13.9 g, 35.4 mmol, yield 75%).

[0171] Mass : [(M+H) + ] :395

[0172]

[0173] [Preparation Example 3] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (A03)

[0174]

[0175] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 43.6mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (6.8g, 43.6mmol), Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 130.9mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (14.7 g, 34.9 mmol, yield 80%).

[0176] Mass : [(M+H) + ] :421

[0177]

[0178] [Preparation Example 4] Synthesis of 2-(4-chlorophenyl)-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (A04)

[0179]

[0180] 2-chloro-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (15.0g, 38.1mmol), 2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.1g, 38.1mmol), Pd(PPh3)4 (1.3g, 1.1mmol), and K2CO3 (15.8g, 114.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (13.4 g, 28.6 mmol, yield 75%).

[0181] Mass : [(M+H) + ] :471

[0182]

[0183] [Preparation Example 5] Synthesis of 2-([1,1':3',1''-terphenyl]-5'-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (A05)

[0184]

[0185] 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 35.7mmol), 2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.5g, 35.7mmol), Pd(PPh3)4 (1.2g, 1.1mmol), and K2CO3 (14.8g, 107.2mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1':3',1''-terphenyl]-5'-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (13.5 g, 27.1 mmol, yield 76%).

[0186] Mass : [(M+H) + ] :497

[0187]

[0188] [Preparation Example 6] Synthesis of 2,4-diphenyl-6-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (B01)

[0189]

[0190] 2-(2'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (20.0g, 47.6mmol), bis(pinacolato)diboron (15.7g, 61.9mmol), Pd(dppf)Cl2 (1.0g, 1.4mmol), X-Phos (1.4g, 2.9mmol), and KOAc (9.3g, 95.3mmol) were added to 200ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the solution was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2,4-diphenyl-6-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (18.3g, 35.7mmol, yield 75%).

[0191] Mass : [(M+H) + ] :512

[0192]

[0193] [Preparation Example 7] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (B02)

[0194]

[0195] A03 (20.0g, 47.6mmol) synthesized by the method of Preparation Example 3, bis(pinacolato)diboron (15.7g, 61.9mmol), Pd(dppf)Cl2 (1.0g, 1.4mmol), X-Phos (1.4g, 2.9mmol), and KOAc (9.3g, 95.3mmol) were added to 200ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, the solution was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (18.3g, 35.7mmol, yield 75%).

[0196] Mass : [(M+H) + ] :512

[0197]

[0198] [Preparation Example 8] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (B03)

[0199]

[0200] 2-([1,1'-biphenyl]-2-yl)-4-(2'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (20.0g, 40.3mmol) and bis(pinacolato)diboron (13.3g, 52.4mmol), Pd(dppf)Cl2 (0.9g, 1.2mmol), X-Phos (1.2g, 2.4mmol), and KOAc (7.9g, 80.6mmol) were added to 200ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the solution was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (17.8 g, 30.2 mmol, yield 75%).

[0201] Mass : [(M+H) + ] :589

[0202]

[0203] [Synthetic Example]

[0204]

[0205] [Synthesization Example 1] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (Compound 001)

[0206]

[0207] A01 (15.0g, 35.7mmol) synthesized by the method of Preparation Example 1, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (15.6g, 35.7mmol), Pd(OAc)2 (0.2g, 1.1mmol), Xphos (1.0g, 2.1mmol), and Cs2CO3 (23.3g, 71.4mmol) were added to 180ml of toluene, 30ml of EtOH, and 30ml of water, and heated and stirred for 4 hours. After the reaction was finished, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was then dehydrated with magnesium sulfate and concentrated to obtain 2-([1,1'-biphenyl]-2-yl)-4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (18.6 g, 26.8 mmol, yield 75%) by column chromatography.

[0208] Mass : [(M+H) + ] : 694

[0209]

[0210] [Synthesization Example 2] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (Compound 005)

[0211]

[0212] A02 (15.0g, 38.1mmol) synthesized by the method of Preparation Example 2, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.7g, 38.1mmol), Pd(OAc)2 (0.3g, 1.1mmol), Xphos (1.1g, 2.3mmol), and Cs2CO3 (24.8g, 76.2mmol) were added to 240ml of toluene, 40ml of EtOH, and 40ml of water, and heated and stirred for 4 hours. After the reaction was finished, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was then dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (19.6 g, 29.3 mmol, yield 77%).

[0213] Mass : [(M+H) + ] : 668

[0214]

[0215] [Synthesization Example 3] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (Compound 016)

[0216]

[0217] A04 (15.0g, 31.9mmol) synthesized by the method of Preparation Example 4, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (13.9g, 31.9mmol), Pd(OAc)2 (0.2g, 1.0mmol), Xphos (0.9g, 1.9mmol), and Cs2CO3 (20.8g, 63.8mmol) were added to 240ml of toluene, 40ml of EtOH, and 40ml of water, and heated and stirred for 4 hours. After the reaction was finished, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was then dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(2-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazine (18.5g, 24.9mmol, yield 78%).

[0218] Mass : [(M+H) + ] : 744

[0219]

[0220] [Synthesization Example 4] Synthesis of 2-([1,1':3',1''-terphenyl]-5'-yl)-4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (Compound 021)

[0221]

[0222] A05 (15.0g, 30.2mmol) synthesized by the method of Preparation Example 5, 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (13.2g, 30.2mmol), Pd(OAc)2 (0.2g, 0.9mmol), Xphos (0.9g, 1.8mmol), and Cs2CO3 (19.7g, 60.5mmol) were added to 240ml of toluene, 40ml of EtOH, and 40ml of water, and heated and stirred for 4 hours. After the reaction was finished, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was then dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1':3',1''-terphenyl]-5'-yl)-4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (17.9 g, 23.3 mmol, yield 77%).

[0223] Mass : [(M+H) + ] : 770

[0224]

[0225] [Synthesization Example 5] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 022)

[0226]

[0227] 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 43.6mmol), B01 (22.3g, 43.6mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 130.9mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (25.2 g, 37.8 mmol, yield 80%).

[0228] Mass : [(M+H) + ] :668

[0229]

[0230] [Synthesization Example 6] Synthesis of 2-([1,1'-biphenyl]-3-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 023)

[0231]

[0232] 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 43.6mmol), B01 (22.3g, 43.6mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 130.9mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (23.9 g, 34.5 mmol, yield 79%).

[0233] Mass : [(M+H) + ] :694

[0234]

[0235] [Synthesization Example 7] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 026)

[0236]

[0237] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (15.0g, 47.2mmol), B01 (24.1g, 47.2mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.6g, 1.4mmol), and K2CO3 (19.6g, 141.6mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (25.2 g, 37.8 mmol, yield 80%).

[0238] Mass : [(M+H) + ] :668

[0239]

[0240] [Synthesization Example 8] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (Compound 071)

[0241]

[0242] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (15.0g, 27.5mmol), B01 (14.0g, 27.5mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.0g, 0.8mmol), and K2CO3 (11.4g, 82.4mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (19.4 g, 21.7 mmol, yield 79%).

[0243] Mass : [(M+H) + ] :896

[0244]

[0245] [Synthesization Example 9] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (Compound 075)

[0246]

[0247] A01 (15.0g, 35.7mmol) synthesized by the method of Preparation Example 1, B02 (18.3g, 35.7mmol) synthesized by the method of Preparation Example 5, Pd(OAc)2 (0.2g, 1.1mmol), Xphos (1.0g, 2.1mmol), and Cs2CO3 (23.3g, 71.4mmol) were added to 240ml of Toluene, 40ml of EtOH, and 40ml of Water, and heated and stirred for 4 hours. After the reaction was finished, the temperature was lowered to room temperature and extracted with methylene chloride. The extracted organic layer was then dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (21.1g, 27.5mmol, yield 77%).

[0248] Mass : [(M+H) + ] : 770

[0249]

[0250] [Synthesization Example 10] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(2'-(4-(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (Compound 085)

[0251]

[0252] 2-([1,1':3',1''-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 35.7mmol), B03 (21.0g, 35.7mmol) synthesized by the method of Preparation Example 8, Pd(PPh3)4 (1.2g, 1.1mmol), and K2CO3 (14.8g, 107.2mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(2'-(4-([1,1':3',1''-terphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (23.8 g, 28.2 mmol, yield 79%).

[0253] Mass : [(M+H) + ] :846

[0254]

[0255] [Synthesization Example 11] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(2'-(4-(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (Compound 090)

[0256]

[0257] 2-chloro-4-(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine (15.0g, 31.9mmol), B03 (18.8g, 31.9mmol) synthesized by the method of Preparation Example 8, Pd(PPh3)4 (1.1g, 1.0mmol), and K2CO3 (13.2g, 95.8mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(2'-(4-(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine (22.9 g, 25.5 mmol, yield 80%).

[0258] Mass : [(M+H) + ] :896

[0259]

[0260] [Synthesization Example 12] Synthesis of 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 094)

[0261]

[0262] 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (15.0g, 41.9mmol), B01 (21.4g, 41.9mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (17.4g, 125.8mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (23.7 g, 33.5 mmol, yield 80%).

[0263] Mass : [(M+H) + ] :708

[0264]

[0265] [Synthesization Example 13] Synthesis of 2-(dibenzo[b,d]thiophen-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 095)

[0266]

[0267] 2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (15.0g, 40.1mmol), B01 (20.5g, 40.1mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.4g, 1.2mmol), and K2CO3 (16.6g, 120.4mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(dibenzo[b,d]thiophen-2-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (23.2 g, 32.1 mmol, yield 80%).

[0268] Mass : [(M+H) + ] :724

[0269]

[0270] [Synthesization Example 14] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(6-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (Compound 097)

[0271]

[0272] 2-chloro-4-phenyl-6-(6-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (15.0g, 34.6mmol), B01 (17.7g, 34.6mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.2g, 1.0mmol), and K2CO3 (14.3g, 103.7mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(6-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (22.2 g, 28.3 mmol, yield 82%).

[0273] Mass : [(M+H) + ] :784

[0274]

[0275] [Synthesization Example 15] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-(9,9-diphenyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine (Compound 102)

[0276]

[0277] 2-chloro-4-(9,9-diphenyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine (15.0g, 29.5mmol), B01 (15.1g, 29.5mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.0g, 0.9mmol), and K2CO3 (12.2g, 88.6mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and refluxed for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-(9,9-diphenyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine (19.7 g, 23.0 mmol, yield 78%).

[0278] Mass : [(M+H) + ] :858

[0279]

[0280] [Synthesization Example 16] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(spiro[fluorene-9,9'-xanthen]-3-yl)-1,3,5-triazine (Compound 105)

[0281]

[0282] 2-chloro-4-phenyl-6-(spiro[fluorene-9,9'-xanthen]-3-yl)-1,3,5-triazine (15.0g, 28.7mmol), B01 (14.7g, 28.7mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.0g, 0.9mmol), and K2CO3 (11.9g, 86.2mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(spiro[fluorene-9,9'-xanthen]-3-yl)-1,3,5-triazine (19.8 g, 22.7 mmol, yield 79%).

[0283] Mass : [(M+H) + ] :872

[0284]

[0285] [Synthesization Example 17] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,3,5-triazine (Compound 106)

[0286]

[0287] 2-chloro-4-phenyl-6-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,3,5-triazine (15.0g, 28.7mmol), B01 (14.7g, 28.7mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.0g, 0.9mmol), and K2CO3 (11.9g, 86.2mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,3,5-triazine (19.5g, 22.7mmol, yield 79%).

[0288] Mass : [(M+H) + ] :859

[0289]

[0290] [Synthesization Example 18] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(pyridin-4-yl)-1,3,5-triazine (Compound 108)

[0291]

[0292] 2-chloro-4-phenyl-6-(pyridin-4-yl)-1,3,5-triazine (15.0g, 55.8mmol), B01 (28.6g, 55.8mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.9g, 1.7mmol), and K2CO3 (23.1g, 167.5mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and refluxed for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenyl-6-(pyridin-4-yl)-1,3,5-triazine (25.9 g, 41.9 mmol, yield 75%).

[0293] Mass : [(M+H) + ] :619

[0294]

[0295] [Synthesization Example 19] Synthesis of 2-(4-(4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-4-phenylquinazoline (Compound 112)

[0296]

[0297] 2-(4-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-4-phenylquinazoline (15.0g, 31.8mmol), B01 (16.3g, 31.8mmol) synthesized by the method of Preparation Example 6, Pd(PPh3)4 (1.1g, 1.0mmol), and K2CO3 (13.2g, 95.3mmol) were added to 200ml of toluene, 30.0ml of ethanol, and 30.0ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4-(4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-4-phenylquinazoline (19.3g, 23.5mmol, yield 74%).

[0298] Mass : [(M+H) + ] :822

[0299]

[0300] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0301] Compound 001 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0302] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0303] On the ITO transparent electrode prepared as described above, compound A and compound B were co-deposited in a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, compound C was deposited on top of the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and compound D and compound E were co-deposited in a weight ratio of 98:2 to form a emitting layer with a thickness of 200 Å. Subsequently, compound F was deposited on top of the emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, and then compound 001 and compound H were co-deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0304] The structures of compounds A to H used at this time are as follows.

[0305]

[0306]

[0307]

[0308] [Examples 2 to 19] Fabrication of Blue Organic Electroluminescent Devices

[0309] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 001, which was used as the electron transport layer material in Example 1.

[0310]

[0311] [Comparative Examples 1 to 4] Fabrication of Blue Organic Electroluminescent Devices

[0312] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that compounds I to K were used instead of compound 001 as the electron transport layer material. At this time, the structures of compounds I to K are as follows.

[0313]

[0314]

[0315] [Evaluation Example 1]

[0316] For the blue organic electroluminescent devices fabricated in Examples 1 to 19 and Comparative Examples 1 to 3, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0317] Sample Electron Transport Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 0013.44538.9 Example 2 Compound 0053.64528.6 Example 3 Compound 0163.54548.9 Example 4 Compound 0213.64548.7 Example 5 Compound 0223.54538.7 Example 6 Compound 0233.64548.8 Example 7 Compound 0263.64528.7 Example 8 Compound 0713.74538.6 Example 9 Compound 0753.54528.8 Example 10 Compound 0853.64538.7 Example 11 Compound 0903.54548.6 Example 12 Compound 0943.64548.7 Example 13 Compound 0953.64538.7 Example 14 Compound 0973.54548.8 Example 15 Compound 1023.64538.9 Example 16 Compound 1053.74528.6 Example 17 Compound 1063.64548.7 Example 18 Compound 1083.44538.8 Example 19 Compound 1123.54538.7 Comparative Example 1 Compound I 3.94557.9 Comparative Example 2 Compound J 4.14547.8 Comparative Example 3 Compound K 3.94557.7

[0318]

[0319] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 19, which used the compounds of the present invention in the electron transport layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 3, which used compounds I to K in the electron transport layer.

[0320] In addition, it was found that the blue organic electroluminescent devices of Examples 1 to 19 exhibited superior performance in terms of driving voltage and current efficiency compared to the blue organic electroluminescent device of Comparative Example 1, which used a compound (e.g., Compound I) in which a pyrimidine was bonded to one of the dual argins in the electron transport layer, and the blue organic electroluminescent devices of Comparative Examples 2 and 3, which used a compound (e.g., Compounds J, K) in the electron transport layer, which had a dual triazine moiety with an aryl group extended to the biphenyl linker.

[0321]

[0322] [Example 20] Fabrication of a Blue Organic Electroluminescent Device

[0323] Compound 005 synthesized in Synthesis Example 2 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0324] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0325] On the ITO transparent electrode prepared as described above, compound A and compound B were co-deposited in a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, compound C was deposited to a thickness of 50 Å on top of the hole transport layer to form a hole transport auxiliary layer, and compound D and compound E were co-deposited in a weight ratio of 98:2 to form an emissive layer with a thickness of 200 Å. Subsequently, compound 005 was deposited on top of the emissive layer to form an electron transport auxiliary layer with a thickness of 50 Å, and then compound G and compound H were co-deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0326] The structures of compounds A to H used at this time are as follows.

[0327]

[0328]

[0329]

[0330] [Examples 21 to 22] Fabrication of a Blue Organic Electroluminescent Device

[0331] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 20, except that the compounds listed in Table 2 below were used instead of Compound 005, which was used as the electron transport auxiliary layer material in Example 20.

[0332]

[0333] [Comparative Example 4] Fabrication of a blue organic electroluminescent device

[0334] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 20, except that compound F was used instead of compound 005 as the electron transport auxiliary layer material.

[0335]

[0336] [Evaluation Example 2]

[0337] For the blue organic electroluminescent devices fabricated in Examples 20 to 22 and Comparative Example 4, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0338] Sample Electron Transport Assisted Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 20 Compound 0053.84537.7 Example 21 Compound 0943.74557.8 Example 22 Compound 0953.74547.9 Comparative Example 4 Compound F4.44557.0

[0339]

[0340] As shown in Table 2 above, it was found that the blue organic electroluminescent device of Examples 20 to 22, which used the compound of the present invention in the electron transport assist layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 4, which used compound F in the electron transport assist layer.

[0341]

[0342] Although embodiments of the present invention have been described above, those skilled in the art will understand that the present invention may be implemented in other specific forms without altering its technical concept or essential features. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. 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 CR1, and at least two of X1 to X3 are N, and X4 to X6 are each independently N or CR2, and at least two of X4 to X6 are N, and Ar1 to Ar4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different, R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, It is selected from alkylamine groups having 1 to 20 carbon atoms or arylamine groups having 6 to 30 carbon atoms, and each of these may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 5 to 20 nuclei.

2. In Paragraph 1, X1 to X3 are each independently N or CR1, and at least two of X1 to X3 are N, and X4 to X6 are each independently N or CR2, and at least two of X4 to X6 are N, and Ar1 to Ar4 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different, R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, 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 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, An organic light-emitting compound selected from an alkylamine group having 1 to 20 carbon atoms or an arylamine group having 6 to 30 carbon atoms, each of which can be unsubstituted or substituted with one or more substituents R' selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 5 to 20 nuclei.

3. In Paragraph 1, X1 to X6 are N, and Ar1 to Ar4 are each independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, each of which may be unsubstituted or substituted with one or more Rs, and Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different, R is each independently deuterium, a halogen group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylboron group having 1 to 10 carbon atoms, an arylboron group having 6 to 20 carbon atoms, an arylphosphine group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 1 to 10 carbon atoms, an arylphosphine oxide group having 6 to 20 carbon atoms, An organic light-emitting compound selected from an alkylamine group having 1 to 10 carbon atoms or an arylamine group having 6 to 20 carbon atoms, each of which may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 10 carbon atoms.

4. In Paragraph 1, X1 to X6 are N, and Ar1 to Ar4 are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, and each may be unsubstituted or substituted with one or more Rs, and Ar1 and Ar2 are different, or Ar3 and Ar4 are different, or Ar1 and Ar2 are different and Ar3 and Ar4 are different, An organic light-emitting compound, wherein R is independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, each of which may be unsubstituted or substituted with one or more substituents R' selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a phenyl group, and a naphthyl group.

5. In Paragraph 1, Ar1 to Ar4 are each independently any one of the following chemical formulas 2-1 to 2-14, and each may be unsubstituted or substituted with one or more R, said R as defined in claim 1, and Y1 and Y2 are each independently O, S, CR3R4 or NR5, and Y3 is independently C or Si, and R3 to R5 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, an organic light-emitting compound.

6. In Paragraph 1, R is each independently any one of the following chemical formulas 3-1 to 3-5, each of which may be unsubstituted or substituted with one or more R', said R' is an organic light-emitting compound as defined in claim 1.

7. In Paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound selected from any one of the following compounds 1 to 112.

8. An organic electroluminescent device comprising an organic light-emitting compound according to claim 1.

9. In Paragraph 8, The above-described 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 above organic light-emitting compound.

10. In Paragraph 8, The above-described organic electroluminescent device comprises: an anode; a cathode; a light-emitting layer disposed between the cathode and the anode; and an electron transport region and an electron transport auxiliary layer disposed between the cathode and the light-emitting layer. The above electron transport region and / or electron transport auxiliary layer is an organic electroluminescent device comprising the above organic light-emitting compound.

11. Use of the organic light-emitting compound according to paragraph 1 in an organic electroluminescent device.

12. In Paragraph 11, An application characterized by the above organic light-emitting compound being used as an electron transport material in the above organic electroluminescent device.

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