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

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2023-0171095, filed November 30, 2023, the entire contents of which are incorporated herein by reference.

[0003] Technology field

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

[0005]

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

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

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

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

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

[0011]

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

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

[0014] Prior art literature

[0015] Republic of Korea Patent Publication No. 10-2017-0118675

[0016]

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

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

[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] Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and at least two of Z1 to Z3 are N, each of which may be unsubstituted or substituted,

[0026] Ar1 and Ar2 are each independently an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or a are arylamine groups, each of which may be unsubstituted or substituted,

[0027] R1 to R3 are each independently an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted, wherein two adjacent groups selected from R1 to R3 may combine to form a condensed ring structure,

[0028] L is represented by *-L1-L2-L3-*, wherein L1 to L3 are each independently an arylene group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted,

[0029] The above L1 and L3 are not bonded to each other in an ortho position to the above L2.

[0030] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

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

[0032]

[0033] The organic light-emitting compound according to the present invention can induce delocalization of the lowest unoccupied molecular orbital (LUMO) orbital by separating the heteroaromatic moiety and the dibenzo moiety utilizing silane into a terphenyl moiety, and can induce maximization of steric hindrance according to the ortho bonding position of the terphenyl moiety, thereby increasing the middle point energy and gathering excitons toward the host side, thereby increasing the efficiency and lifespan of the organic electroluminescent device through the exciton block, and can improve the stability of the molecule by increasing the electron donating property compared to the heteroaromatic moiety composed of general carbon through the dibenzo moiety utilizing silane.

[0034] 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.

[0035] 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.

[0036]

[0037] 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.

[0038] 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.

[0039] 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.

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

[0041] 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.

[0042] 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.

[0043] 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 furyl group, pyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, and benzonaphthofuranyl group. In the above heteroaryl 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 may have a nuclear number of 5 to 60, 5 to 30, or 5 to 20.

[0044] 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.

[0045] 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.

[0046] In the present invention, the term “alkenyl group” may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds in the middle or terminal of an alkyl group.

[0047] In the present invention, the term “alkynyl group” may mean a monovalent functional group derived from a hydrocarbon containing one or more carbon triple bonds in the middle or terminal of an alkyl group.

[0048] 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.

[0049] In the present invention, the terms “alkyloxy group” and “aryloxy group” may each mean a monovalent functional group derived from a compound in which oxygen is further contained at the linking site of the aforementioned alkyl group and aryl group.

[0050] In the present invention, the terms “alkylsilyl group” and “arylsilyl group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with the aforementioned alkyl group and aryl group, respectively.

[0051] In the present invention, the terms “alkylboron group” and “arylboron group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of borane is substituted with the aforementioned alkyl group and aryl group, respectively.

[0052] 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.

[0053] In the present invention, the term "arylamine group" may mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of ammonia is substituted with the aforementioned aryl group.

[0054] In the present invention, the term "substitution" independently means deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, It means being substituted with at least one substituent selected from the group consisting of an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0055]

[0056] Organic luminescent compounds

[0057] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0058] [Chemical Formula 1]

[0059]

[0060] In the above chemical formula 1,

[0061] Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and at least two of Z1 to Z3 are N, each of which may be unsubstituted or substituted,

[0062] Ar1 and Ar2 are each independently an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heterocycloalkyl group having 5 to 40 nuclear atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, An arylphosphine group, an arylphosphine oxide group having 6 to 60 carbon atoms, or an arylamine group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0063] R1 to R3 are each independently an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted, wherein two adjacent groups selected from R1 to R3 may combine to form a condensed ring structure,

[0064] L is represented by *-L1-L2-L3-*, wherein L1 to L3 are each independently an arylene group having 6 to 30 carbon atoms, and each of them may be unsubstituted or substituted,

[0065] The above L1 and L3 are not bonded to each other in an ortho position to the above L2.

[0066] Specifically, in the above, the substitution is, one or more groups of a hydrogen atom, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group which may be present in the R, Ar1, Ar2, R1 to R3 and L are each independently unsubstituted or substituted with deuterium, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a carbon atom It means being substituted with one or more substituents selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0067] In one embodiment, in the chemical formula 1,

[0068] Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, and at least two of Z1 to Z3 are N,

[0069] Ar1 and Ar2 are each independently an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, An arylphosphine group, an arylphosphine oxide group having 6 to 30 carbon atoms, or an arylamine group having 6 to 30 carbon atoms,

[0070] R1 to R3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, wherein two adjacent groups selected from R1 to R3 can combine to form a condensed ring structure (for example, in the case of an aryl group, a condensed ring structure can be formed with an adjacent aryl group).

[0071] L is represented as *-L1-L2-L3-*, and L1 to L3 are each independently an arylene group having 6 to 20 carbon atoms,

[0072] At least one of the binding site (-*) adjacent to L1 and the binding site (-*) adjacent to L3 is bound in an ortho position, and L1 and L3 may not be bound to each other in an ortho position to L2.

[0073] In one embodiment, in the chemical formula 1,

[0074] Z1 to Z3 are each independently N or CH, and at least two of the above Z1 to Z3 are N,

[0075] Ar1 and Ar2 are each independently 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,

[0076] R1 to R3 are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, and at least one of R1 and R3 is an aryl group having 2 to 20 carbon atoms, wherein two adjacent groups selected from R1 to R3 can combine to form a condensed ring structure (for example, in the case of the aryl group, a condensed ring structure can be formed with an adjacent aryl group).

[0077] L is represented as *-L1-L2-L3-*, and L1 to L3 are each independently an arylene group having 6 to 20 carbon atoms,

[0078] At least one of the binding site (-*) adjacent to L1 and the binding site (-*) adjacent to L3 is bound in an ortho position, and L1 and L3 may not be bound to each other in an ortho position to L2.

[0079] In one embodiment, in the chemical formula 1,

[0080] Z1 to Z3 are each independently N or CH, and at least two of the above Z1 to Z3 are N,

[0081] Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group or a dibenzo moiety,

[0082] R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group or a naphthyl group, wherein two adjacent groups selected from R1 to R3 can combine to form a condensed ring structure (for example, the phenyl group, biphenyl group and naphthyl group can each form a condensed ring structure with an adjacent phenyl group, biphenyl group or naphthyl group),

[0083] L is represented as *-L1-L2-L3-*, and L1 to L3 are each independently a phenylene group, a biphenylene group, or a naphthylene group,

[0084] At least one of the binding site (-*) adjacent to L1 and the binding site (-*) adjacent to L3 is bound in an ortho position, and L1 and L3 may not be bound to each other in an ortho position to L2.

[0085] In one embodiment, L may be represented by any one of the following chemical formulas L-1 to L-7.

[0086] [Chemical formula L-1]

[0087]

[0088] [Chemical formula L-2]

[0089]

[0090] [Chemical formula L-3]

[0091]

[0092] [Chemical formula L-4]

[0093]

[0094] [Chemical formula L-5]

[0095]

[0096] [Chemical formula L-6]

[0097]

[0098] [Chemical formula L-7]

[0099]

[0100] In each of the above chemical formulas L-1 to L-7, * represents a site bonded to the above chemical formula 1.

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

[0102] Z1 to Z3 are each independently N or CH, and at least two of the above Z1 to Z3 are N,

[0103] Ar1 and Ar2 are each independently a phenyl group, a biphenyl group or a naphthyl group,

[0104] R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group or a naphthyl group, wherein two adjacent groups selected from R1 to R3 can combine to form a condensed ring structure (for example, the phenyl group, biphenyl group and naphthyl group can each form a condensed ring structure with an adjacent phenyl group, biphenyl group or naphthyl group).

[0105] L can be represented by the following chemical formulas L-1, L-2, L-6 or L-7.

[0106] [Chemical formula L-1]

[0107]

[0108] [Chemical formula L-2]

[0109]

[0110] [Chemical formula L-6]

[0111]

[0112] [Chemical formula L-7]

[0113]

[0114] In each of the above chemical formulas L-1, L-2, L-6 or L-7, * represents a site bonded to the above chemical formula 1.

[0115]

[0116] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 2 to 5.

[0117] [Chemical Formula 2]

[0118]

[0119] [Chemical Formula 3]

[0120]

[0121] [Chemical Formula 4]

[0122]

[0123] [Chemical Formula 5]

[0124]

[0125] In each of the above chemical formulas 2 to 5,

[0126] Ar1 and Ar2 are each independently a phenyl group or a biphenyl group,

[0127] R1 to R3 are each independently a methyl group, a phenyl group, or a biphenyl group, wherein two adjacent groups selected from R1 to R3 can combine to form a condensed ring structure. (For example, the phenyl group and the biphenyl group can each form a condensed ring structure with the adjacent phenyl group or biphenyl group.)

[0128] 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 180.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] As a specific example, the compound represented by the above chemical formula 1 may be any one or more of the above compounds 1, 21, 27, 43, 46, 61, 81, 87, 103, 106, 121, 141, 147, 163 and 166.

[0153] The novel organic light-emitting compound of the present invention can induce delocalization of the lowest unoccupied molecular orbital (LUMO) orbital by separating the heteroaromatic moiety and the dibenzo moiety utilizing silane into a terphenyl moiety. In addition, the organic light-emitting compound can induce maximization of steric hindrance according to the ortho bonding position of the terphenyl moiety, thereby increasing the middle point energy and gathering excitons toward the host side, thereby improving the efficiency and lifespan of the organic electroluminescent device through the exciton block. In addition, the organic light-emitting compound can have a high electron donating property and improve the stability of the molecule through the dibenzo moiety utilizing silane compared to the heteroaromatic moiety composed of general carbon.

[0154] 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.

[0155]

[0156] Organic electroluminescent devices

[0157] 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.

[0158] 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.

[0159] anode

[0160] 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.

[0161] 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.

[0162] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. The anode can be formed, for example, by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0163] cathode

[0164] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0165] 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.

[0166] luminescent layer

[0167] 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.

[0168] 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.

[0169] 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.

[0170] electron transport region

[0171] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0172] 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.

[0173] 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.

[0174] 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 induce delocalization of the lowest unoccupied molecular orbital (LUMO) orbital by separating the heteroaromatic moiety and the dibenzo moiety utilizing silane into a terphenyl moiety, and can induce maximization of steric hindrance according to the ortho bonding position of the terphenyl moiety, thereby increasing the middle point energy and gathering excitons toward the host, thereby increasing the efficiency and lifespan of the organic electroluminescent device through the exciton block, and can improve the electron donating property and molecular stability compared to the heteroaromatic moiety composed of general carbon through the dibenzo moiety utilizing silane. In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0175] 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.

[0176] 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).

[0177] electron transport auxiliary layer

[0178] 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.

[0179] 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 induce delocalization of the lowest unoccupied molecular orbital (LUMO) orbital by separating the heteroaromatic moiety and the dibenzo moiety utilizing silane into a terphenyl moiety, and can induce maximization of steric hindrance according to the ortho bonding position of the terphenyl moiety, thereby increasing the middle point energy and gathering excitons toward the host, thereby increasing the efficiency and lifespan of the organic electroluminescent device through the exciton block, and can improve the electron donating property and molecular stability compared to the heteroaromatic moiety composed of general carbon through the dibenzo moiety utilizing silane. In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport auxiliary layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0180] 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.

[0181] hole transport region

[0182] 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.

[0183] 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.

[0184] 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.

[0185] The hole-injecting material may be any hole-injecting material known in the art without limitation. Non-limiting examples of usable hole-injecting materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,Ndiphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), etc. Can be used alone or in combination of two or more

[0186] 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.

[0187] 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).

[0188] hole transport auxiliary layer

[0189] 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.

[0190] 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.

[0191] 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.

[0192] capping layer

[0193] 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.

[0194] 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).

[0195] 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.

[0196] 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.

[0197] 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.

[0198] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0199] 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.

[0200] 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.

[0201]

[0202] 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.

[0203]

[0204] [Preparation]

[0205] [Preparation Example 1]: Synthesis of SC-1

[0206]

[0207] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to a mixed solvent of 160 ml of dioxane and 40 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-1 (9.2 g, yield 60%).

[0208] 1H-NMR: δ 8.36(d, 4H), 7.96(d, 2H), 7.71(d, 1H), 7.61~7.60(m, 3H), 7.50(t, 6H), 7.38(t, 2H), 7.25(d, 4H)

[0209] Mass: [(M+H) + ] : 497

[0210]

[0211] [Preparation Example 2]: Synthesis of SC-2

[0212]

[0213] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to a mixed solvent of 160 ml of dioxane and 40 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-2 (8.9 g, yield 58%).

[0214] 1H-NMR: δ 8.36(d, 4H), 8.10(d, 2H), 7.96~7.94(m, 3H), 7.73(t, 1H), 7.62~7.50(m, 12H)

[0215] Mass: [(M+H) + ] : 497

[0216]

[0217] [Preparation Example 3]: Synthesis of SC-3

[0218]

[0219] 2-([1,1'-biphenyl]-3-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to a mixed solvent of 160 ml of dioxane and 40 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-3 (8.7 g, yield 59%).

[0220] 1H-NMR: δ 8.38 (d, 1H), 8.36 (d, 2H), 8.10 (d, 2H), 7.96 - 7.94 (m, 4H), 7.75 - 7.73 (m, 4H), 7.62 - 7.60 (m, 7H), 7.50 - 7.41 (m, 6H)

[0221] Mass: [(M+H) + ] : 573

[0222]

[0223] [Example 4]: Synthesis of SC-4

[0224]

[0225] 2-(5-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine(12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid(6.0 g, 25.9 mmol), Pd(PPh3)4(0.9 g, 0.8 mmol), and K2CO3(7.1 g, 51.7 mmol) were added to a mixed solvent of 160 ml of dioxane and 40 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-4 (8.2 g, yield 55%).

[0226] 1H-NMR: δ 8.36(d, 4H), 8.04(s, 1H), 7.75~7.71(m, 3H), 7.61(d, 1H), 7.50~7.38(m, 11H), 7.25(d,4H)

[0227] Mass: [(M+H) + ] : 573

[0228]

[0229] [Preparation Example 5]: Synthesis of SC-5

[0230]

[0231] 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenylpyrimidine(12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-3-yl)boronic acid(6.0 g, 25.9 mmol), Pd(PPh3)4(0.9 g, 0.8 mmol), and K2CO3(7.1 g, 51.7 mmol) were added to a mixed solvent of 160 ml of dioxane and 40 ml of H2O and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-5 (8.3 g, yield 56%).

[0232] 1H-NMR: δ 8.23(s, 1H), 7.96~7.94(m, 7H), 7,75~7.71(m, 5H), 7.61~7.38(m, 12H), 7.25(2, 2H)

[0233] Mass: [(M+H) + ] : 572

[0234]

[0235] [Synthesis example]

[0236] [Synthesis Example 1]: Synthesis of Compound 1

[0237]

[0238] Compound SC-1 (5.0 g, 10.1 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) synthesized by the method of Preparation Example 1 were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O, and reacted while stirring and heating under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (3.1 g, yield 38%).

[0239] Mass: [(M+H) + ] : 797

[0240]

[0241] [Synthesis Example 2]: Synthesis of Compound 21

[0242]

[0243] SC-2 (5.0 g, 10.1 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), synthesized by the method of Preparation Example 2, were added to a mixed solvent of 80 ml of dioxane and 20 ml of H2O, and reacted while heating and stirring under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 21 (3.1 g, yield 39%).

[0244] Mass: [(M+H) + ] : 797

[0245]

[0246] [Synthesis Example 3]: Synthesis of Compound 27

[0247]

[0248] Compound SC-3 (5.0 g, 8.7 mmol), (3-([1,1'-biphenyl]-3-yldiphenylsilyl)phenyl)boronic acid (4.0 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 3 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 27 (3.4 g, yield 41%).

[0249] Mass: [(M+H) + ] : 949

[0250]

[0251] [Synthesis Example 4]: Synthesis of Compound 43

[0252]

[0253] Compound SC-4 (5.0 g, 8.7 mmol), (4-(triphenylsilyl)phenyl)boronic acid (3.3 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 4 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 43 (3.1 g, yield 40%).

[0254] Mass: [(M+H) + ] : 873

[0255]

[0256] [Synthesis Example 5]: Synthesis of Compound 46

[0257]

[0258] Compound SC-5 (5.0 g, 8.8 mmol), (4-(triphenylsilyl)phenyl)boronic acid (3.3 g, 8.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 5 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 46 (3.0 g, yield 39%).

[0259] Mass: [(M+H) + ] : 872

[0260]

[0261] [Synthesis Example 6]: Synthesis of Compound 61

[0262]

[0263] Compound SC-1 (5.0 g, 10.1 mmol), (3-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) synthesized by the method of Preparation Example 1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 61 (2.6 g, yield 38%).

[0264] Mass: [(M+H) + ] : 673

[0265]

[0266] [Synthesis Example 7]: Synthesis of Compound 81

[0267]

[0268] Compound SC-2 (5.0 g, 10.1 mmol), (3-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) synthesized by the method of Preparation Example 2 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 81 (2.8 g, yield 41%).

[0269] Mass: [(M+H) + ] : 673

[0270]

[0271] [Synthesis Example 8]: Synthesis of Compound 87

[0272]

[0273] Compound SC-3 (5.0 g, 10.1 mmol), (3-([1,1'-biphenyl]-3-yldimethylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 3 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 87 (2.9 g, yield 40%).

[0274] Mass: [(M+H) + ] : 825

[0275]

[0276] [Synthesis Example 9]: Synthesis of Compound 103

[0277]

[0278] Compound SC-4 (5.0 g, 10.1 mmol), (4-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 4 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 103 (2.5 g, yield 38%).

[0279] Mass: [(M+H) + ] : 749

[0280]

[0281] [Synthesis Example 10]: Synthesis of Compound 106

[0282]

[0283] Compound SC-5 (5.0 g, 10.1 mmol), (4-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 5 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 106 (2.8 g, yield 42%).

[0284] Mass: [(M+H) + ] : 748

[0285]

[0286] [Synthesis Example 11]: Synthesis of Compound 121

[0287]

[0288] Compound SC-1 (5.0 g, 10.1 mmol), (5,5-diphenyl-5H-dibenzo[b,d]silol-1-yl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) synthesized by the method of Preparation Example 1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 121 (3.2 g, yield 40%).

[0289] Mass: [(M+H) + ] : 795

[0290]

[0291] [Synthesis Example 12]: Synthesis of Compound 141

[0292]

[0293] Compound SC-2 (5.0 g, 10.1 mmol), (5,5-diphenyl-5H-dibenzo[b,d]silol-3-yl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) synthesized by the method of Preparation Example 2 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 141 (3.1 g, yield 39%).

[0294] Mass: [(M+H) + ] : 795

[0295]

[0296] [Synthesis Example 13]: Synthesis of Compound 147

[0297]

[0298] Compound SC-3 (5.0 g, 10.1 mmol), (3-(5-phenyl-5H-dibenzo[b,d]silol-5-yl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 3 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 147 (3.1 g, yield 41%).

[0299] Mass: [(M+H) + ] : 871

[0300]

[0301] [Synthesis Example 14]: Synthesis of Compound 163

[0302]

[0303] Compound SC-4 (5.0 g, 8.7 mmol), (5,5-diphenyl-5H-dibenzo[b,d]silol-2-yl)boronic acid (3.8 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 4 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 163 (3.1 g, yield 41%).

[0304] Mass: [(M+H) + ] : 871

[0305]

[0306] [Synthesis Example 15]: Synthesis of Compound 166

[0307]

[0308] Compound SC-5 (5.0 g, 8.8 mmol), 5,5'-spirobi[dibenzo[b,d]silol]-2-ylboronic acid (3.3 g, 8.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized by the method of Preparation Example 5 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 166 (2.9 g, yield 38%).

[0309] Mass: [(M+H) + ] : 868

[0310]

[0311] [Examples and Comparative Examples]

[0312] [Examples 1 to 15 and Comparative Examples 1 to 7]: Fabrication of blue organic electroluminescent devices

[0313] 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.

[0314] 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.

[0315] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 on the light-emitting auxiliary layer to a thickness of 20 nm, the electron transport layer was formed by co-depositing an electron transport layer material and Liq in a weight ratio of 1:1 on the light-emitting layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structures of HI, HAT-CN6, EB, BH, BD and Liq are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0316] HI HAT-CN6 EB BH BD Liq

[0317] Electron transport layer material Example 1 Compound 1 Example 2 Compound 21 Example 3 Compound 27 Example 4 Compound 43 Example 5 Compound 46 Example 6 Compound 61 Example 7 Compound 81 Example 8 Compound 87 Example 9 Compound 103 Example 10 Compound 106 Example 11 Compound 121 Example 12 Compound 141 Example 13 Compound 147 Example 14 Compound 163 Example 15 Compound 166 Comparative Example 1 Alq3 Comparative Example 2SP-1 Comparative Example 3SP-2 Comparative Example 4SP-3 Comparative Example 5SP-4 Comparative Example 6SP-5 Comparative Example 7SP-6

[0318]

[0319] [Examples 16 to 30 and Comparative Examples 8 to 14]: Fabrication of blue organic electroluminescent devices

[0320] 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.

[0321] 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.

[0322] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HI and HAT-CN6 in a weight ratio of 98:2 on the anode to a thickness of 10 nm, the hole transport layer was formed by depositing HI in a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB in a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by co-depositing BH and BD in a weight ratio of 98:2 to a thickness of 20 nm on the light-emitting auxiliary layer, the electron transport auxiliary layer was formed by depositing an electron transport auxiliary layer material in a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by co-depositing ET and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 30 nm, the electron injection layer was formed by depositing LiF in a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 100 nm on the electron injection layer. Here, the structure of the above ET is shown in Table 3 below, and the electron transport auxiliary layer material is as shown in Table 4 below.

[0323] ET

[0324] Electron transport auxiliary layer material Example 16 Compound 1 Example 17 Compound 21 Example 18 Compound 27 Example 19 Compound 43 Example 20 Compound 46 Example 21 Compound 61 Example 22 Compound 81 Example 23 Compound 87 Example 24 Compound 103 Example 25 Compound 106 Example 26 Compound 121 Example 27 Compound 141 Example 28 Compound 147 Example 29 Compound 163 Example 30 Compound 166 Comparative Example 8 No electron transport auxiliary layer formed Comparative Example 9 SP-1 Comparative Example 10SP-2 Comparative Example 11SP-3 Comparative Example 12SP-4 Comparative Example 13SP-5 Comparative Example 14SP-6

[0325]

[0326] [Experimental Example]

[0327] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 15 and Comparative Examples 1 to 7

[0328] For the organic electroluminescent devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 7, 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.

[0329] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 13.44547.0 Example 23.34557.1 Example 33.24537.0 Example 43.44547.1 Example 53.24546.9 Example 63.34536.8 Example 73.44557.0 Example 83.54557.0 Example 93.34547.1 Example 103.24547.0 Example 113.24557.0 Example 123.34536.9 Example 133.24547.1 Example 143.54557.0 Example 153.34547.1 Comparative example 14.84574.6Comparative example 24.24565.1Comparative example 34.34575.3Comparative example 44.24565.2Comparative example 54.04575.7Comparative example 64.14565.7Comparative example 74.04565.6

[0330] Referring to Table 5 above, the organic electroluminescent devices manufactured in Examples 1 to 15 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 7.

[0331]

[0332] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 16 to 30 and Comparative Examples 8 to 14

[0333] For the organic electroluminescent devices manufactured in Examples 16 to 30 and Comparative Examples 8 to 14, 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.

[0334] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 163.14547.4 Example 173.24547.4 Example 183.24557.3 Example 193.34557.2 Example 203.14547.2 Example 213.24557.3 Example 223.34547.3 Example 233.24547.3 Example 243.14557.4 Example 253.24557.3 Example 263.24547.3 Example 273.14557.4 Example 283.14547.4 Example 293.34547.3 Example 303.24557.3Comparative example 84.64565.3Comparative example 94.24555.8Comparative example 104.14565.8Comparative example 114.34565.5Comparative example 123.84556.2Comparative example 134.14566.1Comparative example 144.04566.0

[0335] Referring to Table 6 above, the organic electroluminescent devices manufactured in Examples 16 to 30 showed generally superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 8 to 14.

[0336] In particular, referring to Tables 5 and 6 above, compared to the comparative examples using SP-3 to SP-6, which are compounds having different ortho bonding positions of L in the structure of the organic light-emitting compound according to the present invention, overall excellent results were shown in the evaluation of driving voltage, luminescence peak, and current efficiency.

[0337] 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, Z 1 Inland Z 3 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and the Z 1 Inland Z 3 At least two of them are N, each of which may be unsubstituted or substituted, Ar 1 and Ar 2 are each independently an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkyloxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, or an arylamine group having 6 to 60 carbon atoms, each of which is may be unsubstituted or substituted, R 1 Inland R 3 are each independently an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted, Here R 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure, L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inside L 3 are each independently an arylene group having 6 to 30 carbon atoms, each of which may be unsubstituted or substituted, Above L 1 and L 3 are mutually reminding L 2 It is not combined in the ortho position.

2. In paragraph 1, The above Z 1 Inland Z 3 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the Z 1 Inland Z 3 Two or more of them are N, Above Ar 1 and Ar 2 are each independently an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyloxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, or an arylamine group having 6 to 30 carbon atoms, Above R 1 Inland R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, wherein R 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure, The above L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inside L 3 are each independently an arylene group having 6 to 20 carbon atoms, Above L 1 The binding site adjacent to (-*) and L 3 At least one of the binding sites (-*) adjacent to L is bound in an ortho position, and 1 and L 3 are each other L 2 An organic luminescent compound that is not bonded in the ortho position.

3. In paragraph 1, The above Z 1 Inland Z 3 are each independently N or CH, and the Z 1 Inland Z 3 Two or more of them are N, Above Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, Above R 1 Inland R 3 are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, and R 1 and R 3 At least one of R is an aryl group having 2 to 20 carbon atoms, wherein 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure, The above L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inside L 3 are each independently an arylene group having 6 to 20 carbon atoms, Above L 1 The binding site adjacent to (-*) and L 3 At least one of the binding sites (-*) adjacent to L is bound in an ortho position, and 1 and L 3 are each other L 2 An organic luminescent compound that is not bonded in the ortho position.

4. In paragraph 1, The above Z 1 Inland Z 3 are each independently N or CH, and the Z 1 Inland Z 3 Two or more of them are N, Above Ar 1 and Ar 2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group or a dibenzo moiety, Above R 1 Inland R 3 are each independently a methyl group, a phenyl group, a biphenyl group or a naphthyl group, wherein R 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure, The above L is *-L 1 -L 2 -L 3 -* is indicated, and the above L 1 Inside L 3 are each independently a phenylene group, a biphenylene group or a naphthylene group, Above L 1 The binding site adjacent to (-*) and L 3 At least one of the binding sites (-*) adjacent to L is bound in an ortho position, and 1 and L 3 are each other L 2 An organic luminescent compound that is not bonded in the ortho position.

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

6. In paragraph 1, The above Z 1 Inland Z 3 are each independently N or CH, and the Z 1 Inland Z 3 Two or more of them are N, Above Ar 1 and Ar 2 are each independently a phenyl group, a biphenyl group or a naphthyl group, Above R 1 Inland R 3 are each independently a methyl group, a phenyl group, a biphenyl group or a naphthyl group, wherein R 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure, wherein L is an organic luminescent compound represented by the following chemical formula L-1, L-2, L-6 or L-7: [Chemical formula L-1] [Chemical formula L-2] [Chemical formula L-6] [Chemical formula L-7] In each of the above chemical formulas L-1, L-2, L-6 or L-7, * represents a site bonded to the above chemical formula 1.

7. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound represented by any one of the following chemical formulas 2 to 5: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In each of the chemical formulas 2 to 5 above, Ar 1 and Ar 2 are each independently a phenyl group or a biphenyl group, R 1 Inland R 3 are each independently a methyl group, a phenyl group or a biphenyl group, wherein R 1 Inland R 3 Two adjacent groups selected from can combine to form a condensed ring structure.

8. 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 180.

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

10. In paragraph 9, 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.

11. In paragraph 10, 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.

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

13. In paragraph 12, 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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