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, wherein the organic electroluminescent device may have a high current efficiency and a low driving voltage.

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0179250, filed December 12, 2023, and Korean Patent Application No. 10-2024-0170443, filed November 26, 2024, 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. 10-2017-0094770

[0016]

[0017] The present invention aims to provide a novel compound and its use, which can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer material and an electron transport auxiliary layer material, due to the characteristics of excellent heat resistance, thermal stability, and long lifespan, and at the same time, improved electron transport ability and luminescence ability.

[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] [Chemical Formula 1]

[0023]

[0024] In the above chemical formula 1,

[0025] R1 is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms,

[0026] X1 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or the following chemical formula 2,

[0027] Here, at least one group composed of two or more adjacent groups selected from X1 to X8 is formed by combining the two or more adjacent groups to form at least one condensed ring structure, and at least one of X1 to X8 that does not form the condensed ring structure is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or the following chemical formula 2,

[0028] [Chemical Formula 2]

[0029]

[0030] In the above chemical formula 2,

[0031] * indicates a site that is bonded to the above chemical formula 1,

[0032] A is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or an arylamine group having 6 to 30 carbon atoms,

[0033] Ar1 is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms, or an arylamine group having 6 to 60 carbon atoms,

[0034] L1 is a single bond, an arylene group having 6 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms,

[0035] n and m are each independently integers from 0 to 3,

[0036] The hydrogen atoms, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, arylphosphine groups, arylphosphine oxide groups and arylamine groups that may be present in the above X1 to X8, R1, R2, A and Ar1, and the arylene groups and heteroarylene groups that may be present in L1 are each independently unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, It may be substituted with one or more substituents selected from the group consisting of an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group.

[0037] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0038] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0039]

[0040] The organic light-emitting compound according to the present invention can provide an organic layer material with improved performance by adding an electron withdrawing group (EWG) or electron donating group (EDG) structure that can increase electron density by using an aromatic linker to a condensed phosphine oxide moiety that strongly interacts with a metal within the structure, thereby inducing a stronger interaction.

[0041] 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.

[0042] 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.

[0043]

[0044] 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.

[0045] 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.

[0046] 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.

[0047] Hereinafter, embodiments of the present invention will be described in detail.

[0048] 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.

[0049] In the present invention, the term “aryl group” may mean a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may refer to, for example, a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a chrysenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, etc., but is not limited thereto. Additionally, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon.

[0050] In the present invention, the term "heteroaryl group" may mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a purinyl group, an indazolyl group, a quinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group, acridinyl group, phenanthridinyl group, carbazolyl group,Nitrogen-containing heteroaryl groups including a phenanthrolinyl group, a phenazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples thereof include oxygen-containing heteroaryl groups such as a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, and a benzonaphthofuranyl group. In addition, the term "heteroarylene group" may refer to a divalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroarylene 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 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 nuclear number of 5 to 60, 5 to 30, or 5 to 20.

[0051] 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.

[0052] 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.

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

[0054] In the present invention, the 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.

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

[0056] In the present invention, the terms “arylphosphine group” and “arylphosphine oxide group” may mean a monovalent functional group derived from a compound in which the above-described aryl group is substituted on an oxide and a phosphine oxide, respectively.

[0057] 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 and aryl group, respectively.

[0058] In the present invention, the term "substitution" is independently selected from the group consisting of deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group. It means being substituted with one or more substituents, and when substituted with multiple substituents, they may be the same or different.

[0059]

[0060] Organic luminescent compounds

[0061] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0062] [Chemical Formula 1]

[0063]

[0064] In the above chemical formula 1,

[0065] R1 is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 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,

[0066] X1 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heterocycloalkyl group having 5 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or the following chemical formula 2,

[0067] Here, at least one group composed of two or more adjacent groups selected from X1 to X8 is formed by combining the two or more adjacent groups to form at least one condensed ring structure, and at least one of X1 to X8 that does not form the condensed ring structure is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heterocycloalkyl group having 5 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or the following chemical formula 2,

[0068] [Chemical Formula 2]

[0069]

[0070] In the above chemical formula 2,

[0071] * indicates a site that is bonded to the above chemical formula 1,

[0072] A is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, or an arylamine group having 6 to 30 carbon atoms,

[0073] Ar1 is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkylamine group having 1 to 40 carbon atoms, or an arylamine group having 6 to 60 carbon atoms,

[0074] L1 is 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,

[0075] n and m are each independently integers from 0 to 3,

[0076] The hydrogen atoms, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, arylphosphine groups, arylphosphine oxide groups and arylamine groups that may be present in the above X1 to X8, R1, R2, A and Ar1, and the arylene groups and heteroarylene groups that may be present in L1 are each independently unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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 carbon atom of 1 to It may be substituted with one or more substituents selected from the group consisting of an alkylsilyl group having 20 carbon atoms, an arylsilyl 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, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group.

[0077] For example, if n is 0, it may mean that L1 does not exist and A of the chemical formulas 1 and 2 is single bonded, and if m is 0, it may mean that hydrogen present in A is not substituted with Ar1.

[0078] In one embodiment, in the chemical formula 1,

[0079] R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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, It may be substituted with an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group,

[0080] X1 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an 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 arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or the following chemical formula 2, each of which may be unsubstituted or substituted,

[0081] Here, at least one group composed of two or more adjacent groups selected from X1 to X8 is formed by combining two or more adjacent groups to form one or more condensed ring structures, and at least one of X1 to X8 that does not form the condensed ring structure is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an 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 arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or the following chemical formula 2, each of which is unsubstituted or It may be substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, or a halogen group,

[0082] [Chemical Formula 2]

[0083]

[0084] In the above chemical formula 2,

[0085] A is 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, or an arylamine group having 6 to 30 carbon atoms, which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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 alkylamine group having 1 to 20 carbon atoms, It may be substituted with an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group,

[0086] Ar1 is 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 alkylamine group having 1 to 20 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear 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, It may be substituted with an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group,

[0087] L1 is 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,

[0088] n and m are each independently integers from 0 to 3.

[0089] In one embodiment, the chemical formula 2 may be represented by any one of the following chemical formulas 2A to 2E.

[0090] [Chemical Formula 2A]

[0091]

[0092] [Chemical Formula 2B]

[0093]

[0094] [Chemical Formula 2C]

[0095]

[0096] [Chemical Formula 2D]

[0097]

[0098] [Chemical Formula 2E]

[0099]

[0100] In each of the above chemical formulas 2A to 2E,

[0101] Z1 to Z3 are each independently N or CR3, wherein R3 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, and at least one of Z1 to Z3 is N.

[0102] Z4 to Z7 are each independently N or CR3, wherein R3 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, and at least one of Z4 to Z7 is N.

[0103] Z8 is O, S or CR4R5, wherein R4 and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms,

[0104] Z9 is N or CR6, wherein R6 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms,

[0105] Ar2 to Ar8 are each independently hydrogen, 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, or a cyano group, each of which may be unsubstituted or substituted.

[0106] L2 to L6 are each independently 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,

[0107] n is an integer from 0 to 3.

[0108] In one embodiment, in the chemical formula 1,

[0109] R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 may be unsubstituted or substituted with a cyano group or a halogen group,

[0110] X1 to X4 are each independently CR2, wherein R2 is deuterium, hydrogen or an aryl group having 6 to 30 carbon atoms, and wherein at least one group consisting of two or more adjacent groups selected from X1 to X4, wherein the two or more adjacent groups combine with each other to form at least one condensed ring structure,

[0111] X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, and at least one of X5 to X8 is an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, each of which may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl 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 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an arylamine group having 6 to 30 carbon atoms, a cyano group or a halogen group,

[0112] [Chemical Formula 2A]

[0113]

[0114] [Chemical Formula 2B]

[0115]

[0116] [Chemical Formula 2C]

[0117]

[0118] In each of the above chemical formulas 2A to 2C,

[0119] Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N,

[0120] Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N,

[0121] Z8 is O, S or CR4R5, wherein R4 and R5 are each independently an alkyl group having 1 to 20 carbon atoms,

[0122] Ar2 to Ar6 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a cycloalkyl group or cyano group having 3 to 20 carbon atoms,

[0123] L2 to L4 are each independently an arylene group having 6 to 30 carbon atoms,

[0124] n is 1.

[0125] In one embodiment, the chemical formula 1 may be represented by the following chemical formula 1A or the following chemical formula 1B.

[0126] [Chemical Formula 1A]

[0127]

[0128] [Chemical Formula 1B]

[0129]

[0130] In each of the above chemical formulas 1A and 1B,

[0131] R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 may be unsubstituted or substituted with a cyano group or a halogen group,

[0132] X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, and at least one of X5 to X8 is an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, each of which may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl 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 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an arylamine group having 6 to 30 carbon atoms, a cyano group or a halogen group,

[0133] [Chemical Formula 2A]

[0134]

[0135] [Chemical Formula 2B]

[0136]

[0137] [Chemical Formula 2C]

[0138]

[0139] In each of the above chemical formulas 2A to 2C,

[0140] Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N,

[0141] Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N,

[0142] Z8 is O, S or CR4R5, wherein R4 and R5 are each independently an alkyl group having 1 to 20 carbon atoms,

[0143] Ar2 to Ar6 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a cycloalkyl group or cyano group having 3 to 20 carbon atoms,

[0144] L2 to L4 are each independently an arylene group having 6 to 30 carbon atoms,

[0145] n is 1.

[0146] In one embodiment, the chemical formula 1 may be represented by the following chemical formula 1A or the following chemical formula 1B.

[0147] [Chemical Formula 1A]

[0148]

[0149] [Chemical Formula 1B]

[0150]

[0151] In each of the above chemical formulas 1A and 1B,

[0152] R1 is a methyl group, an ethyl group, a butyl group, a phenyl group, a tolyl group, a cyclohexyl group or a pyridinyl group, each of which may be unsubstituted or substituted with a cyano group or a halogen group,

[0153] X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a diphenylanthracenyl group, the following formula 2A, the following formula 2B, or the following formula 2C, and at least one of X5 to X8 is a phenyl group, a biphenyl group, a terphenyl group, a diphenylanthracenyl group, the following formula 2A, the following formula 2B, or the following formula 2C, and each of these may be unsubstituted or substituted with a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyrimidinyl group, a quinolinyl group, a diphenylamine group, a naphthyl group, a trifluoromethyl group, or fluorine,

[0154] [Chemical Formula 2A]

[0155]

[0156] [Chemical Formula 2B]

[0157]

[0158] [Chemical Formula 2C]

[0159]

[0160] In each of the above chemical formulas 2A to 2C,

[0161] Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N,

[0162] Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N,

[0163] Z8 is O, S or CR4R5, where R4 and R5 are each independently a methyl group,

[0164] Ar2 to Ar6 are each independently hydrogen, a phenyl group or a biphenyl group, and each of them may be unsubstituted or substituted with a cyclohexyl group or a cyano group,

[0165] L2 to L4 are each independently a phenylene group,

[0166] n is 1.

[0167] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one of the following compounds 1 to 222.

[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] As a specific example, the compound represented by the above chemical formula 1 may be any one of the above compounds 1, 2, 3, 21, 22, 41, 42, 61, 62, 81, 82, 101, 102, 121, 122, 151, 152, 171, 172 and 201.

[0214] The novel organic light-emitting compound of the present invention can realize improved performance by adding an electron withdrawing group (EWG) or electron donating group (EDG) structure that can increase electron density using an aromatic linker to a condensed phosphine oxide moiety that strongly interacts with a metal within the structure, thereby inducing a stronger interaction.

[0215] In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be achieved.

[0216]

[0217] Organic electroluminescent devices

[0218] 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.

[0219] 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.

[0220] anode

[0221] 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.

[0222] 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.

[0223] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. For example, the anode can be formed by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0224] cathode

[0225] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0226] 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.

[0227] luminescent layer

[0228] 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.

[0229] 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.

[0230] 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.

[0231] electron transport region

[0232] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0233] 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.

[0234] 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.

[0235] The above electron transport layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention can achieve improved performance by inducing a stronger interaction by adding an electron withdrawing group (EWG) or electron donating group (EDG) structure that can increase electron density using an aromatic linker to a condensed phosphine oxide moiety that strongly interacts with a metal within the structure. In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be achieved.

[0236] 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.

[0237] 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).

[0238] electron transport auxiliary layer

[0239] 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.

[0240] The above electron transport auxiliary layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention can achieve improved performance by inducing a stronger interaction by adding an electron withdrawing group (EWG) or electron donating group (EDG) structure that can increase electron density using an aromatic linker to a condensed phosphine oxide moiety that strongly interacts with a metal in the structure. In addition, by using the novel organic light-emitting compound according to the present invention as a material for the electron transport auxiliary layer, excellent performance in terms of driving voltage, emission peak, and current efficiency can be achieved.

[0241] 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.

[0242] hole transport region

[0243] 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.

[0244] 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.

[0245] 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.

[0246] 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. Can be used alone or in combination of two or more

[0247] 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.

[0248] 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).

[0249] luminescent auxiliary layer

[0250] The organic electroluminescent device of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region and the light-emitting layer. The light-emitting auxiliary layer serves to transport holes moving from the hole transport region to the light-emitting layer, while also serving to control the thickness of the organic layer. The light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer, and has a high triplet (T1) energy to prevent excitons in the light-emitting layer from diffusing to the hole transport layer.

[0251] These light-emitting auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the light-emitting auxiliary layers of the red, green, and blue organic light-emitting devices may be made of the same material.

[0252] The above-mentioned light-emitting auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives can be used. In addition, the light-emitting auxiliary layer may optionally include a p-type dopant in addition to the above-mentioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field can be used.

[0253] capping layer

[0254] 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.

[0255] 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).

[0256] 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.

[0257] 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.

[0258]

[0259] 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.

[0260] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0261] 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.

[0262] 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.

[0263]

[0264] 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.

[0265]

[0266] [Preparation]

[0267] [Preparation Example 1]: Synthesis of H-1

[0268]

[0269] (1-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and dichloro(methyl)phosphane (1.1 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (1-(4-bromophenyl)naphthalen-2-yl)(methyl)phosphine oxide (1.9 g, yield 50%).

[0270]

[0271] The above-obtained (1-(4-bromophenyl)naphthalen-2-yl)(methyl)phosphine oxide (3.45 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-1 (1.72 g, yield 50%) was obtained using column chromatography.

[0272]

[0273] [Preparation Example 2]: Synthesis of H-2

[0274]

[0275] ((3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and dichloro(methyl)phosphane (1.9 g, 10 mmol) were added to 20 ml of THF, stirred at 80 °C for 3 hours, and then cooled to 0 °C. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 °C, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, column chromatography was used to obtain the target compound (3-(4-bromophenyl)naphthalen-2-yl)(methyl)phosphine oxide (1.89 g, yield 49%).

[0276]

[0277] The above-obtained (3-(4-bromophenyl)naphthalen-2-yl)(methyl)phosphine oxide (3.45 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-2 (1.69 g, yield 49%) was obtained using column chromatography.

[0278]

[0279] [Example 3]: Synthesis of H-3

[0280]

[0281] (1-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and dichloro(phenyl)phosphane (1.7 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (1-(4-bromophenyl)naphthalen-2-yl)(phenyl)phosphine oxide (1.85 g, yield 48%).

[0282]

[0283] The above-obtained (1-(4-bromophenyl)naphthalen-2-yl)(phenyl)phosphine oxide (4.07 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-3 (1.79 g, yield 44%) was obtained using column chromatography.

[0284]

[0285] [Example 4]: Synthesis of H-4

[0286]

[0287] (3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and dichloro(phenyl)phosphane (1.7 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (3-(4-bromophenyl)naphthalen-2-yl)(phenyl)phosphine oxide (1.81 g, yield 47%).

[0288]

[0289] The above-obtained (3-(4-bromophenyl)naphthalen-2-yl)(phenyl)phosphine oxide (4.07 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-4 (1.66 g, yield 41%) was obtained using column chromatography.

[0290]

[0291] [Example 5]: Synthesis of H-5

[0292]

[0293] (1-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and 2-(dichlorophosphaneyl)pyridine (1.8 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (1-(4-bromophenyl)naphthalen-2-yl)(pyridin-2-yl)phosphine oxide (1.73 g, yield 45%).

[0294]

[0295] The above-obtained (1-(4-bromophenyl)naphthalen-2-yl)(pyridin-2-yl)phosphine oxide (4.08 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-5 (1.83 g, yield 45%) was obtained using column chromatography.

[0296]

[0297] [Example 6]: Synthesis of H-6

[0298]

[0299] (3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and 2-(dichlorophosphaneyl)pyridine (1.8 g, 10 mmol) were added to 20 ml of THF, stirred at 80 °C for 3 hours, and then cooled to 0 °C. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 °C, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (3-(4-bromophenyl)naphthalen-2-yl)(pyridin-2-yl)phosphine oxide (1.81 g, yield 47%).

[0300]

[0301] The above-obtained (3-(4-bromophenyl)naphthalen-2-yl)(pyridin-2-yl)phosphine oxide (4.08 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-6 (1.93 g, yield 50%) was obtained using column chromatography.

[0302]

[0303] [Example 7]: Synthesis of H-7

[0304]

[0305] (1-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and 4-(dichlorophosphaneyl)benzonitrile (2.0 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and the target compound 4-((1-(4-bromophenyl)naphthalen-2-yl)hydrophosphoryl)benzonitrile (1.93 g, yield 50%) was obtained using column chromatography.

[0306]

[0307] The above-obtained 4-((1-(4-bromophenyl)naphthalen-2-yl)hydrophosphoryl)benzonitrile (4.32 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-7 (1.90 g, yield 44%) was obtained using column chromatography.

[0308]

[0309] [Example 8]: Synthesis of H-8

[0310]

[0311] (3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and 4-(dichlorophosphaneyl)benzonitrile (2.0 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and reacted while stirring for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and the target compound 4-((3-(4-bromophenyl)naphthalen-2-yl)hydrophosphoryl)benzonitrile (1.93 g, yield 50%) was obtained using column chromatography.

[0312]

[0313] The above-obtained 4-((3-(4-bromophenyl)naphthalen-2-yl)hydrophosphoryl)benzonitrile (4.32 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound H-8 (1.77 g, yield 41%) was obtained using column chromatography.

[0314]

[0315] [Example 9]: Synthesis of H-9

[0316]

[0317] (3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and dichloro(p-tolyl)phosphane (1.9 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (3-(4-bromophenyl)naphthalen-2-yl)(p-tolyl)phosphine oxide (1.85 g, yield 48%).

[0318]

[0319] The above-obtained (3-(4-bromophenyl)naphthalen-2-yl)(p-tolyl)phosphine oxide (4.21 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-9 (1.77 g, yield 44%) was obtained using column chromatography.

[0320]

[0321] [Example 10]: Synthesis of H-10

[0322]

[0323] (3-(4-bromophenyl)naphthalen-2-yl)magnesium bromide (3.8 g, 10 mmol) and tert-butyldichlorophosphane (1.58 g, 10 mmol) were added to 20 ml of THF, stirred at 80 ℃ for 3 hours, and then cooled to 0 ℃. 2 ml of water was added to the reaction mixture, stirred for 10 minutes, cooled to 0 ℃, and then 4 ml of triethylamine was added and stirred for 10 minutes. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and column chromatography was used to obtain the target compound (3-(4-bromophenyl)naphthalen-2-yl)(4-(tert-butyl)phenyl)phosphine oxide (1.63 g, yield 43%).

[0324]

[0325] The above-obtained (3-(4-bromophenyl)naphthalen-2-yl)(4-(tert-butyl)phenyl)phosphine oxide (4.21 g, 10 mmol) and silver nitrate (0.16 g, 1 mmol) were added to 100 ml of THF, stirred at 50 °C for 1 hour, and then cooled to 25 °C. 20 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound H-10 (1.97 g, yield 47%) was obtained using column chromatography.

[0326]

[0327] [Synthesis example]

[0328] [Synthesis Example 1]: Synthesis of Compound 1

[0329]

[0330] H-1 (3.43 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 1 (2.40 g, yield 70%) was obtained using column chromatography.

[0331] Mass: [(M+H) + ] : 571

[0332]

[0333] [Synthesis Example 2]: Synthesis of Compound 2

[0334]

[0335] H-1 (3.43 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 2 (2.07 g, yield 60%) was obtained using column chromatography.

[0336] Mass: [(M+H)+ ] : 570

[0337]

[0338] [Synthesis Example 3]: Synthesis of Compound 3

[0339]

[0340] Compound H-1 (3.43 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 3 (1.7 g, yield 50%) was obtained using column chromatography.

[0341] Mass: [(M+H) + ] : 570

[0342]

[0343] [Synthesis Example 4]: Synthesis of Compound 21

[0344]

[0345] Compound H-2 (3.43 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 2 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 21 (2.51. g, yield 73%) was obtained using column chromatography.

[0346] Mass: [(M+H) + ] : 571

[0347]

[0348] [Synthesis Example 5]: Synthesis of Compound 22

[0349]

[0350] Compound H-2 (3.43 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 2 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 22 (1.7 g, yield 50%) was obtained using column chromatography.

[0351] Mass: [(M+H) + ] : 570

[0352]

[0353] [Synthesis Example 6]: Synthesis of Compound 41

[0354]

[0355] Compound H-3 (4.05 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 3 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 41 (2.91 g, yield 72%) was obtained using column chromatography.

[0356] Mass: [(M+H) + ] : 633

[0357]

[0358] [Synthesis Example 7]: Synthesis of Compound 42

[0359]

[0360] Compound H-3 (4.05 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 3 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 42 (1.78 g, yield 44%) was obtained using column chromatography.

[0361] Mass: [(M+H) + ] : 632

[0362]

[0363] [Synthesis Example 8]: Synthesis of Compound 61

[0364]

[0365] Compound H-4 (4.05 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 4 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 61 (3.12. g, yield 77%) was obtained using column chromatography.

[0366] Mass: [(M+H) + ] : 633

[0367]

[0368] [Synthesis Example 9]: Synthesis of Compound 62

[0369]

[0370] Compound H-4 (4.05 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 4 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 62 (3.72 g, yield 92%) was obtained using column chromatography.

[0371] Mass: [(M+H) + ] : 632

[0372]

[0373] [Synthesis Example 10]: Synthesis of Compound 81

[0374]

[0375] Compound H-5 (4.06 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 5 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 81 (2.88 g, yield 71%) was obtained using column chromatography.

[0376] Mass: [(M+H) + ] : 634

[0377]

[0378] [Synthesis Example 11]: Synthesis of Compound 82

[0379]

[0380] Compound H-5 (4.06 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 5 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 82 (3.72 g, yield 92%) was obtained using column chromatography.

[0381] Mass: [(M+H) + ] : 633

[0382]

[0383] [Synthesis Example 12]: Synthesis of Compound 101

[0384]

[0385] Compound H-6 (4.06 g, 10 mmol) synthesized by the method of Preparation Example 6, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound 101 (3.53 g, yield 87%) was obtained using column chromatography.

[0386] Mass: [(M+H) + ] : 634

[0387]

[0388] [Synthesis Example 13]: Synthesis of Compound 102

[0389]

[0390] Compound H-6 (4.06 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 6 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 102 (2.88 g, yield 71%) was obtained using column chromatography.

[0391] Mass: [(M+H) + ] : 633

[0392]

[0393] [Synthesis Example 14]: Synthesis of Compound 121

[0394]

[0395] Compound H-7 (4.30 g, 10 mmol) synthesized by the method of Preparation Example 7, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol) and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH and 25 ml of H2O and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, compound 121 (3.18 g, yield 74%) was obtained using column chromatography.

[0396] Mass: [(M+H) + ] : 658

[0397]

[0398] [Synthesis Example 15]: Synthesis of Compound 122

[0399]

[0400] Compound H-7 (4.30 g, 10 mmol) synthesized by the method of Preparation Example 7, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 122 (3.69 g, yield 86%) was obtained using column chromatography.

[0401] Mass: [(M+H) + ] : 657

[0402]

[0403] [Synthesis Example 16]: Synthesis of Compound 151

[0404]

[0405] Compound H-8 (4.30 g, 10 mmol) synthesized by the method of Preparation Example 8, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol) and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH and 25 ml of H2O and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, compound 151 (3.05 g, yield 71%) was obtained using column chromatography.

[0406] Mass: [(M+H) + ] : 658

[0407]

[0408] [Synthesis Example 17]: Synthesis of Compound 152

[0409]

[0410] Compound H-8 (4.30 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) synthesized by the method of Preparation Example 8 were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 152 (3.61 g, yield 84%) was obtained using column chromatography.

[0411] Mass: [(M+H) + ] : 657

[0412]

[0413] [Synthesis Example 18]: Synthesis of Compound 171

[0414]

[0415] Compound H-9 (4.19 g, 10 mmol) synthesized by the method of Preparation Example 9, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol) and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH and 25 ml of H2O and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, compound 171 (2.97 g, yield 71%) was obtained using column chromatography.

[0416] Mass: [(M+H) + ] : 647

[0417]

[0418] [Synthesis Example 19]: Synthesis of Compound 172

[0419]

[0420] Compound H-9 (4.19 g, 10 mmol) synthesized by the method of Preparation Example 9, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.34 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol) and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH and 25 ml of H2O and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, compound 172 (3.64 g, yield 87%) was obtained using column chromatography.

[0421] Mass: [(M+H) + ] : 646

[0422]

[0423] [Synthesis Example 20]: Synthesis of Compound 201

[0424]

[0425] Compound H-10 (3.85 g, 10 mmol) synthesized by the method of Preparation Example 10, 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (4.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol) and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of toluene, 25 ml of EtOH and 25 ml of H2O and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, compound 201 (3.64 g, yield 59%) was obtained using column chromatography.

[0426] Mass: [(M+H) + ] : 613

[0427]

[0428] [Examples and Comparative Examples]

[0429] [Examples 1 to 20 and Comparative Examples 1 to 3]: Fabrication of blue organic electroluminescent devices

[0430] 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.

[0431] 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.

[0432] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 on the light-emitting auxiliary layer to a thickness of 20 nm, the electron transport auxiliary layer was formed by depositing HB in a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by co-depositing an electron transport layer material and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structures of HI, HAT-CN6, EB, BH, BD, BH and Liq are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0433] HI HAT-CN6 EB BH BD HB Liq

[0434] Electron transport layer material Example 1 Compound 1 Example 2 Compound 2 Example 3 Compound 3 Example 4 Compound 21 Example 5 Compound 22 Example 6 Compound 41 Example 7 Compound 42 Example 8 Compound 61 Example 9 Compound 62 Example 10 Compound 81 Example 11 Compound 82 Example 12 Compound 101 Example 13 Compound 102 Example 14 Compound 121 Example 15 Compound 122 Example 16 Compound 151 Example 17 Compound 152 Example 18 Compound 171 Example 19 Compound 172 Example 20 Compound 201 Comparative Example 1ET1 Comparative Example 2ET2 Comparative Example 3ET3

[0435]

[0436] [Examples 21 to 40 and Comparative Examples 4 to 6]: Fabrication of blue organic electroluminescent devices

[0437] 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.

[0438] 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.

[0439] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 to a thickness of 20 nm on the light-emitting auxiliary layer, the electron transport auxiliary layer was formed by depositing an electron transport auxiliary layer material in a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by co-depositing ET and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structures of HI, HAT-CN6, EB, BH, BD and Liq are as shown in Table 1 above, the structure of ET is shown in Table 3 below, and the electron transport auxiliary layer materials are as shown in Table 4 below.

[0440] ET

[0441] Electron transport auxiliary layer material Example 21 Compound 1 Example 22 Compound 2 Example 23 Compound 3 Example 24 Compound 21 Example 25 Compound 22 Example 26 Compound 41 Example 27 Compound 42 Example 28 Compound 61 Example 29 Compound 62 Example 30 Compound 81 Example 31 Compound 82 Example 32 Compound 101 Example 33 Compound 102 Example 34 Compound 121 Example 35 Compound 122 Example 36 Compound 151 Example 37 Compound 152 Example 38 Compound 171 Example 39 Compound 172 Example Compound 201 Comparative Example 4HB1 Comparative Example 5HB2 Comparative example 6HB3

[0442]

[0443] [Experimental Example]

[0444] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 20 and Comparative Examples 1 to 3

[0445] For the organic electroluminescent devices manufactured in Examples 1 to 20 and Comparative Examples 1 to 3, 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.

[0446] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 14.34527.3 Example 24.14526.1 Example 34.34516.5 Example 44.24596.1 Example 54.24526.2 Example 64.14516.1 Example 74.64537.6 Example 84.54527.7 Example 94.24507.5 Example 104.34527.3 Example 114.14526.1 Example 124.34516.5 Example 134.24596.1 Example 144.24526.2 Example 154.14516.1 Example 164.64537.6 Example 174.54527.7 Example 184.34507.2 Example 194.24517.1 Example 204.54537.1 Comparative Example 15.64515.3 Comparative Example 25.24515.3 Comparative Example 35.14525.4

[0447] Referring to Table 5 above, the organic electroluminescent devices manufactured in Examples 1 to 20 showed generally superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 1 to 3.

[0448]

[0449] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 21 to 40 and Comparative Examples 4 to 6

[0450] For the organic electroluminescent devices manufactured in Examples 21 to 40 and Comparative Examples 4 to 6, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 6 below.

[0451] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 214.14527.1 Example 224.24556.3 Example 234.34516.5 Example 244.24596.4 Example 254.24546.2 Example 264.14516.6 Example 274.64537.6 Example 284.54537.7 Example 294.24507.5 Example 304.64527.3 Example 314.64516.6 Example 324.34516.5 Example 334.24596.1 Example 344.44506.1 Example 354.14516.1 Example 364.14537.6 Example 374.54537.2 Example 384.24507.2 Example 394.24517.1 Example 404.54537.3 Comparative Example 45.74515.2 Comparative Example 55.94545.3 Comparative Example 65.64535.1

[0452] Referring to Table 6 above, the organic electroluminescent devices manufactured in Examples 21 to 40 showed generally superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 4 to 6.

[0453]

[0454] 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, R1 is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, X1 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or the following chemical formula 2, wherein at least one group composed of two or more adjacent groups selected from X1 to X8, wherein the two or more adjacent groups are bonded to each other to form at least one condensed ring structure, and at least one of X1 to X8 that does not form the condensed ring structure is an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or a group represented by the following chemical formula 2, [Chemical formula 2] In the above chemical formula 2, * indicates a site that is bonded to the chemical formula 1 above, A is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, Ar1 is an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms, or an arylamine group having 6 to 60 carbon atoms, L1 is a single bond, an arylene group having 6 to 60 carbon atoms, or a heteroarylene group having 2 to 60 carbon atoms, n and m are each independently an integer from 0 to 3, The hydrogen atoms, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, arylphosphine groups, arylphosphine oxide groups and arylamine groups which may be present in X1 to X8, R1, R2, A and Ar1, and the arylene groups and heteroarylene groups which may be present in L1 are each independently unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, It may be substituted with one or more substituents selected from the group consisting of an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group.

2. In paragraph 1, The above R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, It may be substituted with an arylphosphine oxide group, a cyano group or a halogen group, The above X1 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or the following chemical formula 2, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, or a arylphosphine oxide group having 6 to 30 carbon atoms. which may be substituted with an aryl group, 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group, wherein at least one group composed of two or more adjacent groups selected from X1 to X8, wherein the two or more adjacent groups are bonded to each other to form at least one condensed ring structure, and at least one of X1 to X8 that does not form the condensed ring structure is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or the following chemical formula 2, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a condensed ring structure having 1 to It may be substituted with a haloalkyl group having 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group, [Chemical formula 2] In the above chemical formula 2, A is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, which may be unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, or a halogen group. There is, Ar1 is an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 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 alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, It may be substituted with an arylphosphine oxide group, a cyano group or a halogen group, L1 is a single bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms, An organic luminescent compound wherein n and m are each independently an integer from 0 to 3.

3. In paragraph 1, The above chemical formula 2 is an organic light-emitting compound represented by any one of the following chemical formulas 2A to 2E: [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] [Chemical Formula 2D] [Chemical Formula 2E] In each of the above chemical formulas 2A to 2E, Z1 to Z3 are each independently N or CR3, wherein R3 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, and at least one of said Z1 to Z3 is N, Z4 to Z7 are each independently N or CR3, wherein R3 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, and at least one of Z4 to Z7 is N, Z8 is O, S or CR4R5, wherein R4 and R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, Z9 is N or CR6, wherein R6 is hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 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 arylphosphine group having 6 to 30 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, Ar2 to Ar8 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, or a cyano group, each of which may be unsubstituted or substituted, L2 to L6 are each independently an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms, n is an integer from 0 to 3.

4. In paragraph 1, The above R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 may be unsubstituted or substituted with a cyano group or a halogen group, The above X1 to X4 are each independently CR2, wherein R2 is deuterium, hydrogen or an aryl group having 6 to 30 carbon atoms, and wherein at least one group consisting of two or more adjacent groups selected from X1 to X4 is such that the two or more adjacent groups combine with each other to form at least one condensed ring structure, The above X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, and at least one of the above X5 to X8 is an aryl group having 6 to 30 carbon atoms, the following chemical formula 2A, the following chemical formula 2B or the following chemical formula 2C, and each of them may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl 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 2 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a cyano group or a halogen group, [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] In each of the above chemical formulas 2A to 2C, Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N, Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N, Z8 is O, S or CR4R5, where R4 and R5 are each independently an alkyl group having 1 to 20 carbon atoms, Ar2 to Ar6 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a cycloalkyl group or a cyano group having 3 to 20 carbon atoms. L2 to L4 are each independently an arylene group having 6 to 30 carbon atoms, An organic luminescent compound in which n is 1.

5. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by the following chemical formula 1A or the following chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In each of the above chemical formulas 1A and 1B, R1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 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 may be unsubstituted or substituted with a cyano group or a halogen group, X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, an aryl group having 6 to 30 carbon atoms, the following formula 2A, the following formula 2B, or the following formula 2C, and at least one of said X5 to X8 is an aryl group having 6 to 30 carbon atoms, the following formula 2A, the following formula 2B, or the following formula 2C, and each of them may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl 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 2 to 30 carbon atoms, an arylamine group having 6 to 30 carbon atoms, a cyano group, or a halogen group, [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] In each of the above chemical formulas 2A to 2C, Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N, Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N, Z8 is O, S or CR4R5, where R4 and R5 are each independently an alkyl group having 1 to 20 carbon atoms, Ar2 to Ar6 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a cycloalkyl group or a cyano group having 3 to 20 carbon atoms. L2 to L4 are each independently an arylene group having 6 to 30 carbon atoms, n is 1.

6. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by the following chemical formula 1A or the following chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In each of the above chemical formulas 1A and 1B, R1 is a methyl group, an ethyl group, a butyl group, a phenyl group, a tolyl group, a cyclohexyl group or a pyridinyl group, each of which may be unsubstituted or substituted with a cyano group or a halogen group, X5 to X8 are each independently CR2, wherein R2 is deuterium, hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a diphenylanthracenyl group, the following formula 2A, the following formula 2B, or the following formula 2C, and at least one of said X5 to X8 is a phenyl group, a biphenyl group, a terphenyl group, a diphenylanthracenyl group, the following formula 2A, the following formula 2B, or the following formula 2C, and each of them may be unsubstituted or substituted with a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyrimidinyl group, a quinolinyl group, a diphenylamine group, a naphthyl group, a trifluoromethyl group, or fluorine, [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] In each of the above chemical formulas 2A to 2C, Z1 to Z3 are each independently N or CH, and at least one of Z1 to Z3 is N, Z4 to Z7 are each independently N or CH, and at least one of Z4 to Z7 is N, Z8 is O, S or CR4R5, where R4 and R5 are each independently a methyl group, Ar2 to Ar6 are each independently hydrogen, a phenyl group or a biphenyl group, each of which may be unsubstituted or substituted with a cyclohexyl group or a cyano group, L2 to L4 are each independently a phenylene group, n is 1.

7. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound which is any one of the following compounds 1 to 222.

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

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

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

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

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

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