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

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0171096, filed November 30, 2023, and Korean Patent Application No. 10-2024-0147485, filed October 25, 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. 10-2021-0030417

[0016]

[0017] The purpose of the present invention is to provide a novel organic light-emitting compound having excellent thermal stability, hole-electron binding force, efficiency, etc., and its use.

[0018] In addition, the present invention aims to provide an organic electroluminescent device having a low driving voltage, high current efficiency, and improved light-emitting performance and lifespan, including the novel organic light-emitting 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] X1 to X3 and each independently N or CR1, and at least one of the X1 to X3 is N,

[0026] Y1 to Y3 are each independently N or CR2, and at least one of Y1 to Y3 is N,

[0027] Except for the case where all of the above X1 to X3 and Y1 to Y3 are N,

[0028] R1 and R2 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, a silyl group having 1 to 60 carbon atoms, a phosphine oxide group having 1 to 60 carbon atoms, or a nitrile group, each of which may be unsubstituted or substituted.

[0029] Ar1 to Ar4 are each independently an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a silyl group having 4 to 60 carbon atoms, a phosphine oxide group having 3 to 60 carbon atoms, or a nitrile group, each of which may be unsubstituted or substituted.

[0030] The present invention also 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 has excellent thermal stability due to a high glass transition temperature (Tg), thus providing a long lifespan, and at the same time, has improved electron transport ability, luminescence ability, etc., and can be used as an organic layer material for an excellent organic electroluminescent device.

[0034] In addition, an organic electroluminescent device including an organic light-emitting compound according to the present invention can have significantly improved luminous performance, driving voltage, lifespan, efficiency, etc., and can thus 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.

[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 including a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzonaphthofuranyl group, etc. For example, the heteroaryl group may have 5 to 60, 5 to 30, or 5 to 20 nuclear atoms.

[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, and a cyclooctyl group, but is not limited thereto.

[0046] 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.

[0047] In the present invention, the term "silyl group" may 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 / or aryl group.

[0048] In the present invention, the term "phosphine oxide group" may mean a monovalent functional group derived from a compound in which a phosphine oxide is substituted with the aforementioned alkyl group and / or allyl group.

[0049] In the present invention, the term "substitution" means substitution with one or more substituents independently selected from the group consisting of deuterium, halogen, cyano group, nitrile group, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, cycloalkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 20 carbon atoms, and heteroaryl group having 5 to 20 nuclear atoms, and when substituting with multiple substituents, they may be the same as or different from each other. Furthermore, the substituent may be in the form of a deuterium (D) substance bonded thereto.

[0050]

[0051] Organic luminescent compounds

[0052] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0053] [Chemical Formula 1]

[0054]

[0055] In the above chemical formula 1,

[0056] X1 to X3 and each independently N or CR1, and at least one of the X1 to X3 is N,

[0057] Y1 to Y3 are each independently N or CR2, and at least one of Y1 to Y3 is N,

[0058] Except for the case where all of the above X1 to X3 and Y1 to Y3 are N,

[0059] R1 and R2 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, a heteroaryl group having 5 to 50 nuclear atoms, a silyl group having 1 to 60 carbon atoms, a phosphine oxide group having 1 to 60 carbon atoms, or a nitrile group, each of which may be unsubstituted or substituted.

[0060] Ar1 to Ar4 are each independently an alkyl group having 1 to 30 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, a silyl group having 4 to 60 carbon atoms, a phosphine oxide group or a nitrile group having 3 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0061] Specifically, at least one group among the hydrogen atom, alkyl group, aryl group, heteroaryl group, silyl group, phosphine oxide and nitrile group which may each be present in R1, R2 and Ar1 to Ar4 may be independently unsubstituted or substituted with at least one substituent selected from the group consisting of deuterium, halogen, cyano group, nitrile group, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, cycloalkyl group having 1 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 20 carbon atoms and heteroaryl group having 5 to 20 nuclear atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0062] In one embodiment, the chemical formula 1 is

[0063] X1 to X3 and each independently N or CR1, and at least one of the X1 to X3 is N,

[0064] Y1 to Y3 are each independently N or CR2, and at least one of Y1 to Y3 is N,

[0065] Except for the case where all of the above X1 to X3 and Y1 to Y3 are N,

[0066] The above R1 and R2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,

[0067] The above Ar1 to Ar4 are each independently 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 silyl group having 1 to 30 carbon atoms, or a phosphine oxide group having 1 to 30 carbon atoms, and each of these may be unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 5 to 20 nuclear atoms, a halogen group, a nitrile group, or a hydroxy group.

[0068] In one embodiment, the chemical formula 1 is

[0069] X1 to X3 and each independently N or CR1, and at least one of the X1 to X3 is N,

[0070] Y1 to Y3 are each independently N or CR2, and at least one of Y1 to Y3 is N,

[0071] Except for the case where all of the above X1 to X3 and Y1 to Y3 are N,

[0072] The above R1 and R2 are each independently hydrogen,

[0073] The above Ar1 to Ar4 are each independently one of the following chemical formulae 1-1 to 1-17, and each of them may be unsubstituted or substituted with deuterium, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, a heteroaryl group having 5 to 10 nuclear atoms, a halogen group, a nitrile group, or a hydroxyl group.

[0074] [Chemical Formula 1-1]

[0075]

[0076] [Chemical Formula 1-2]

[0077]

[0078] [Chemical Formula 1-3]

[0079]

[0080] [Chemical Formula 1-4]

[0081]

[0082] [Chemical Formula 1-5]

[0083]

[0084] [Chemical Formula 1-6]

[0085]

[0086] [Chemical Formula 1-7]

[0087]

[0088] [Chemical Formula 1-8]

[0089]

[0090] [Chemical Formula 1-9]

[0091]

[0092] [Chemical Formula 1-10]

[0093]

[0094] [Chemical Formula 1-11]

[0095]

[0096] [Chemical Formula 1-12]

[0097]

[0098] [Chemical Formula 1-13]

[0099]

[0100] [Chemical Formula 1-14]

[0101]

[0102] [Chemical Formula 1-15]

[0103]

[0104] [Chemical Formula 1-16]

[0105]

[0106] [Chemical Formula 1-17]

[0107]

[0108] In the above chemical formulas 1-1 to 1-17, * represents a site that is bonded to the above chemical formula 1,

[0109] R4 and R5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R4 and R5 may be connected to each other to form a ring.

[0110] The ring formed by the above R4 and R5 connecting to each other means that R4 and R5 are connected by a single bond to have a ring structure. For example, when R4 is an alkyl group having 5 carbon atoms and R5 is an alkyl group having 4 carbon atoms, R4 and R5 can be connected to each other to form a ring having up to 9 carbon atoms, but the connection position of the single bond connecting R4 and R5 is not limited to the terminal of R4 and R5, and can also be formed at the middle position of R4 and R5. The ring formed by the above R4 and R5 connecting to each other can be, for example, cyclopentane, cyclohexane, cycloheptane, chlorocyclopentane, chlorocyclohexane, etc., but is not limited thereto.

[0111] In one embodiment, the chemical formula 1 is

[0112] One of the above X1 to X3 is N and one of the above Y1 to Y3 is N, or one of the above X1 to X3 is N and two of the above Y1 to Y3 are N, or two of the above X1 to X3 are N and two of the above Y1 to Y3 are N, or both of the above X1 to X3 are N and one of the above Y1 to Y3 is N, or both of the above X1 to X3 are N and two of the above Y1 to Y3 are N;

[0113] The above R1 and R2 are each independently hydrogen;

[0114] The above Ar1 and Ar2 are each independently one of the following chemical formulas 1-1 to 1-3; and

[0115] The above Ar3 and Ar4 are each independently any one of the following chemical formulae 1-1 to 1-3, 1-7 to 1-9 and 1-12 to 1-17, and each of them may be unsubstituted or substituted with deuterium, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group or a nitrile group.

[0116] [Chemical Formula 1-1]

[0117]

[0118] [Chemical Formula 1-2]

[0119]

[0120] [Chemical Formula 1-3]

[0121]

[0122] [Chemical Formula 1-7]

[0123]

[0124] [Chemical Formula 1-8]

[0125]

[0126] [Chemical Formula 1-9]

[0127]

[0128] [Chemical Formula 1-12]

[0129]

[0130] [Chemical Formula 1-13]

[0131]

[0132] [Chemical Formula 1-14]

[0133]

[0134] [Chemical Formula 1-15]

[0135]

[0136] [Chemical Formula 1-16]

[0137]

[0138] [Chemical Formula 1-17]

[0139]

[0140] In the above chemical formulas 1-1 to 1-3, 1-7 to 1-9 and 1-12 to 1-17, * represents a site bonded to the above chemical formula 1,

[0141] R4 and R5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R4 and R5 may be connected to each other to form a ring.

[0142] In one embodiment, the chemical formula 1 is

[0143] Two of the above X1 to X3 are N and all of the above Y1 to Y3 are N, or all of the above X1 to X3 are N and two of the above Y1 to Y3 are N, or two of the above X1 to X3 are N and two of the above Y1 to Y3 are N;

[0144] The above R1 and R2 are each independently hydrogen;

[0145] The above Ar1 and Ar2 are represented by the following chemical formula 1-1, and

[0146] The above Ar3 and Ar4 are each independently any one of the following chemical formulas 1-1, 1-2, 1-7, 1-8, 1-14 and 1-15, each of which may be unsubstituted or substituted with a halogen group.

[0147] [Chemical Formula 1-1]

[0148]

[0149] [Chemical Formula 1-2]

[0150]

[0151] [Chemical Formula 1-7]

[0152]

[0153] [Chemical Formula 1-8]

[0154]

[0155] [Chemical Formula 1-14]

[0156]

[0157] [Chemical Formula 1-15]

[0158]

[0159] In the above chemical formulas 1-1, 1-2, 1-7, 1-8, 1-14 and 1-15, * represents a site that is bonded to the above chemical formula 1,

[0160] R4 and R5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R4 and R5 may be connected to each other to form a ring.

[0161] 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 701.

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] In one embodiment, the chemical formula 1 may be any one of the following chemical formulas 2 to 6.

[0232] [Chemical Formula 2]

[0233]

[0234] [Chemical Formula 3]

[0235]

[0236] [Chemical Formula 4]

[0237]

[0238] [Chemical Formula 5]

[0239]

[0240] [Chemical Formula 6]

[0241]

[0242] In each of the above chemical formulas 2 to 6,

[0243] The above Ar1 and Ar2 are phenyl groups,

[0244] The above Ar3 and Ar4 are each independently a phenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrimidinyl group, or a fluorophenyl group.

[0245] As a specific example, the compound represented by the above chemical formula 1 may be any one of the above compounds 1, 17, 27, 39, 58, 61, 96, 111, 271, 287, 297, 309, 328, 361, 411, 441, 449, 471, 468, 506 and 521.

[0246] The novel organic light-emitting compound of the present invention has two strong electron-withdrawing triazine groups and pyrimidine groups in its molecular structure, and thus has advantageous properties in electron injection and transfer, and thus has excellent electron transfer ability to the light-emitting layer. Therefore, when it is used in an organic electroluminescent device, it can be excellent in improving the initial driving voltage of the device.

[0247] In addition, the novel organic light-emitting compound of the present invention has a structure in which a triazine group and a pyrimidine group are bonded to both sides of the biphenyl group, one of which is bonded at the ortho position and the other at the meta position, thereby improving the lowest unoccupied molecular orbital (LUMO) energy level to be shallow and improving the fairness.

[0248] In addition, the novel organic light-emitting compound of the present invention has a structure of an aromatic hydrocarbon group rather than a simple aliphatic ring group, so that high thermal stability can be expected, and in addition, since there is no crystallization temperature (Tc) of the material, it is effective in improving the processability of the device as well as its lifespan.

[0249]

[0250] Organic electroluminescent devices

[0251] 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.

[0252] 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.

[0253] anode

[0254] 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.

[0255] 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.

[0256] 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.

[0257] cathode

[0258] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0259] 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.

[0260] luminescent layer

[0261] 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.

[0262] 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.

[0263] 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.

[0264] electron transport region

[0265] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0266] 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.

[0267] 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.

[0268] The above electron transport layer may include the organic light-emitting compound according to the present invention described above. Since the organic light-emitting compound according to the present invention has two strong electron withdrawers in its molecular structure and thus has advantageous properties in electron injection and transfer, by using it in the electron transport layer, the electron transfer ability to the light-emitting layer can be increased, thereby effectively improving the initial driving voltage of the organic electroluminescent device. In addition, the organic light-emitting compound according to the present invention has a structure in which a triazine group and a pyrimidine group are bonded to both sides of the biphenyl group, one of which is bonded at the ortho position and the other is bonded at the meta position, thereby improving the lowest unoccupied molecular orbital (LUMO) energy level to be shallow and improving processability. In addition, an organic electroluminescent device using the organic light-emitting compound according to the present invention in the electron transport layer can have a low refractive index, high efficiency, and a long lifespan.

[0269] 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.

[0270] 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).

[0271] electron transport auxiliary layer

[0272] 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.

[0273] The above-described electron transport auxiliary layer may include the organic light-emitting compound according to the present invention described above. Since the organic light-emitting compound according to the present invention has two strong electron withdrawers in its molecular structure and thus has advantageous properties in electron injection and transfer, by using it in the electron transport auxiliary layer, the electron transport ability to the light-emitting layer can be increased, thereby effectively improving the initial driving voltage of the organic electroluminescent device. In addition, the organic light-emitting compound according to the present invention has a structure in which a triazine group and a pyrimidine group are bonded to both sides of the biphenyl group, one of which is bonded at the ortho position and the other is bonded at the meta position, thereby improving the lowest unoccupied molecular orbital (LUMO) energy level to be shallow and improving processability. In addition, an organic electroluminescent device using the organic light-emitting compound according to the present invention in the electron transport auxiliary layer can have a low refractive index, high efficiency, and a long lifespan.

[0274] 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.

[0275] hole transport region

[0276] 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.

[0277] 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.

[0278] 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.

[0279] 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

[0280] 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.

[0281] 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).

[0282] luminescent auxiliary layer

[0283] 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.

[0284] 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.

[0285] 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.

[0286] capping layer

[0287] 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.

[0288] 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).

[0289] 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.

[0290] 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.

[0291] 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.

[0292] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0293] 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.

[0294] 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.

[0295]

[0296] 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.

[0297]

[0298] [Preparation]

[0299] [Preparation Example 1]: Synthesis of H-1

[0300]

[0301] 2-Chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 ℃ for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound H-1 (2.14 g, yield 80%) was obtained using column chromatography.

[0302]

[0303] [Preparation Example 2]: Synthesis of H-2

[0304]

[0305] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine(4.19 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)(2.5 g, 10 mmol), Pd(dppf)Cl2(0.2 g, 0.3 mmol), XPhos(0.3 g, 0.6 mmol), and KOAc(2.0 g, 19.9 mmol) were added to 100 ml of 1,4-Dioxane and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, and MgSO4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound H-2 (3.1 g, yield 75%) was obtained using column chromatography.

[0306]

[0307] [Example 3]: Synthesis of H-3

[0308]

[0309] 4-Chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 ℃ for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, the target compound H-3 (2.13 g, yield 80%) was obtained using column chromatography.

[0310]

[0311] [Example 4]: Synthesis of H-4

[0312]

[0313] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine(4.18 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)(2.5 g, 10 mmol), Pd(dppf)Cl2(0.2 g, 0.3 mmol), XPhos(0.3 g, 0.6 mmol), and KOAc(2.0 g, 19.9 mmol) were added to 100 ml of 1,4-Dioxane and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, and MgSO4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound H-4 (2.93 g, yield 70%) was obtained using column chromatography.

[0314]

[0315] [Example 5]: Synthesis of H-5

[0316]

[0317] 2-Chloro-4,6-diphenylpyrimidine (2.66 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.1 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 ℃ for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, the target compound H-5 (2.13 g, yield 80%) was obtained using column chromatography.

[0318]

[0319] [Example 6]: Synthesis of H-6

[0320]

[0321] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyridine(4.18 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)(2.5 g, 10 mmol), Pd(dppf)Cl2(0.2 g, 0.3 mmol), XPhos(0.3 g, 0.6 mmol), and KOAc(2.0 g, 19.9 mmol) were added to 100 ml of 1,4-Dioxane and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, and MgSO4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound H-6 (2.93 g, yield 70%) was obtained using column chromatography.

[0322]

[0323] [Synthesis example]

[0324] [Synthesis Example 1]: Synthesis of Compound 1

[0325]

[0326] H-2 (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and reacted at 100 °C for 8 hours with stirring. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 1 (3.58 g, yield 70%) was obtained using column chromatography.

[0327] Mass: [(M+H) + ] : 615

[0328]

[0329] [Synthesis Example 2]: Synthesis of Compound 17

[0330]

[0331] H-2 (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 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 stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 17 (3.83 g, yield 75%) was obtained using column chromatography.

[0332] Mass: [(M+H) + ] : 615

[0333]

[0334] [Synthesis Example 3]: Synthesis of Compound 27

[0335]

[0336] H-2 (5.11 g, 10 mmol), 4-chloro-2-(naphthalen-2-yl)-6-phenylpyrimidine (3.16 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 27 (4.5 g, yield 88%) was obtained using column chromatography.

[0337] Mass: [(M+H) + ] : 665

[0338]

[0339] [Synthesis Example 4]: Synthesis of Compound 39

[0340]

[0341] H-2 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine (3.56 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent in the filtered organic layer, compound 39 (4.60 g, yield 90%) was obtained using column chromatography.

[0342] Mass: [(M+H) + ] : 705

[0343]

[0344] [Synthesis Example 5]: Synthesis of Compound 58

[0345]

[0346] H-2 (5.11 g, 10 mmol), 4-chloro-2-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenylpyrimidine (3.82 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 toluene (100 ml), Et4-chloro-2-(dibenzo[b,d]thiophen-3-yl)-6-phenylpyrimidineOH (25 ml), and H2O (25 ml) and stirred at 100 ℃ for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound 58 (3.78 g, yield 74%) was obtained using column chromatography.

[0347] Mass: [(M+H) + ] : 731

[0348]

[0349] [Synthesis Example 6]: Synthesis of Compound 61

[0350]

[0351] H-2 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]thiophen-3-yl)-6-phenylpyrimidine (3.72 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 61 (3.89 g, yield 76%) was obtained using column chromatography.

[0352] Mass: [(M+H) +] : 772

[0353]

[0354] [Synthesis Example 7]: Synthesis of Compound 96

[0355]

[0356] H-2 (5.11 g, 10 mmol), 4-chloro-6-phenyl-2-(pyridin-3-yl)pyrimidine (2.67 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and reacted at 100 °C for 8 hours with stirring. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent in the filtered organic layer, compound 96 (3.94 g, yield 77%) was obtained using column chromatography.

[0357] Mass: [(M+H) + ] : 616

[0358]

[0359] [Synthesis Example 8]: Synthesis of Compound 111

[0360]

[0361] H-2 (5.11 g, 10 mmol), 4-chloro-2-(4-fluorophenyl)-6-phenylpyrimidine (2.84 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 111 (3.78 g, yield 74%) was obtained using column chromatography.

[0362] Mass: [(M+H) + ] : 633

[0363]

[0364] [Synthesis Example 9]: Synthesis of Compound 271

[0365]

[0366] H-4 (5.10 g, 10 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 271 (3.83 g, yield 75%) was obtained using column chromatography.

[0367] Mass: [(M+H) + ] : 615

[0368]

[0369] [Synthesis Example 10]: Synthesis of Compound 287

[0370]

[0371] H-6 (5.11 g, 10 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 287 (3.93 g, yield 77%) was obtained using column chromatography.

[0372] Mass: [(M+H) + ] : 615

[0373]

[0374] [Synthesis Example 11]: Synthesis of Compound 297

[0375]

[0376] H-6 (5.11 g, 10 mmol), 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (3.17 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent in the filtered organic layer, compound 297 (3.32 g, yield 65%) was obtained using column chromatography.

[0377] Mass: [(M+H) + ] : 665

[0378]

[0379] [Synthesis Example 12]: Synthesis of Compound 309

[0380]

[0381] H-4 (5.11 g, 10 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 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 using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound 309 (3.83 g, yield 75%) was obtained using column chromatography.

[0382] Mass: [(M+H) + ] : 705

[0383]

[0384] [Synthesis Example 13]: Synthesis of Compound 328

[0385]

[0386] H-4 (5.11 g, 10 mmol), 2-chloro-4-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenyl-1,3,5-triazine (3.83 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 using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound 328 (3.78 g, yield 74%) was obtained using column chromatography.

[0387] Mass: [(M+H)+ ] : 731

[0388]

[0389] [Synthesis Example 14]: Synthesis of Compound 361

[0390]

[0391] H-4 (5.11 g, 10 mmol), 2-chloro-4-(4-fluorophenyl)-6-phenyl-1,3,5-triazine (2.85 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 361 (4.08 g, yield 80%) was obtained using column chromatography.

[0392] Mass: [(M+H) + ] : 633

[0393]

[0394] [Synthesis Example 15]: Synthesis of Compound 411

[0395]

[0396] H-4 (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 411 (3.73 g, yield 73%) was obtained using column chromatography.

[0397] Mass: [(M+H) + ] : 614

[0398]

[0399] [Synthesis Example 16]: Synthesis of Compound 441

[0400]

[0401] H-4 (5.11 g, 10 mmol), 4-chloro-2-(naphthalen-1-yl)-6-phenylpyrimidine (3.16 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, compound 441 (3.93 g, yield 77%) was obtained using column chromatography.

[0402] Mass: [(M+H) + ] : 664

[0403]

[0404] [Synthesis Example 17]: Synthesis of Compound 449

[0405]

[0406] H-4 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine (3.56 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 using methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 449 (3.83 g, yield 75%) was obtained using column chromatography.

[0407] Mass: [(M+H) + ] : 704

[0408]

[0409] [Synthesis Example 18]: Synthesis of Compound 471

[0410]

[0411] H-4 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]thiophen-3-yl)-6-phenylpyrimidine (3.72 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and the mixture was stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent from the filtered organic layer, compound 471 (3.93 g, yield 77%) was obtained using column chromatography.

[0412] Mass: [(M+H) + ] : 720

[0413]

[0414] [Synthesis Example 19]: Synthesis of Compound 468

[0415]

[0416] H-4 (5.11 g, 10 mmol), 4-chloro-2-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenylpyrimidine (3.82 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and stirred at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent in the filtered organic layer, compound 468 (3.78 g, yield 74%) was obtained using column chromatography.

[0417] Mass: [(M+H) + ] : 730

[0418]

[0419] [Synthesis Example 20]: Synthesis of Compound 506

[0420]

[0421] H-4 (5.11 g, 10 mmol), 4-chloro-6-phenyl-2-(pyridin-3-yl)pyrimidine (2.67 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 H2O, and 25 ml of H2O, and reacted with stirring at 100 °C for 8 hours. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 506 (3.83 g, yield 75%) was obtained using column chromatography.

[0422] Mass: [(M+H) + ] : 615

[0423]

[0424] [Synthesis Example 21]: Synthesis of Compound 521

[0425]

[0426] H-4 (5.11 g, 10 mmol), 4-chloro-2-(4-fluorophenyl)-6-phenylpyrimidine (2.84 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 toluene (100 ml), EtOH (25 ml), and H2O (25 ml) and reacted at 100 °C for 8 hours with stirring. After completion of the reaction, extraction was performed using methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent in the filtered organic layer, compound 521 (3.68 g, yield 72%) was obtained using column chromatography.

[0427] Mass: [(M+H) + ] : 632

[0428]

[0429] [Examples and Comparative Examples]

[0430] [Examples 1 to 21 and Comparative Examples 1 to 3]: Fabrication of blue organic electroluminescent devices

[0431] 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.

[0432] 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 isopropyl alcohol and dried. Then, the substrate was cleaned with UV for 5 minutes using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) to produce a substrate on which an ITO transparent electrode was formed. The produced substrate was then transferred to a vacuum deposition machine.

[0433] 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 depositing 98 wt% HI and 2 wt% HAT-CN6 to a thickness of 10 nm on the anode, the hole transport layer was formed by depositing HI to a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB to a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by depositing 98 wt% BH and 2 wt% BD 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 to a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by depositing ET and Liq at a weight ratio of 1:1 to a thickness of 30 nm on the electron transport auxiliary layer, the electron injection layer was formed by depositing LiF to a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al to a thickness of 100 nm on the electron injection layer. Here, the structures of HI, HAT-CN6, EB, BH, BD, ET and Liq are shown in Table 1 below, and the electron transport auxiliary layer materials are as shown in Table 2 below.

[0434] HI HAT-CN6 EB BH BD ET Liq

[0435] Electron transport auxiliary layer material Example 1 Compound 1 Example 2 Compound 17 Example 3 Compound 27 Example 4 Compound 39 Example 5 Compound 58 Example 6 Compound 61 Example 7 Compound 96 Example 8 Compound 111 Example 9 Compound 271 Example 10 Compound 287 Example 11 Compound 297 Example 12 Compound 309 Example 13 Compound 328 Example 14 Compound 361 Example 15 Compound 411 Example 16 Compound 441 Example 17 Compound 449 Example 18 Compound 471 Example 19 Compound 468 Example Compound 506 Example 21 Compound 521 Comparative Example 1 HB1 Comparative Example 2HB2 Comparative Example 3HB3

[0436]

[0437] [Examples 22 to 42 and Comparative Examples 4 to 6]: Fabrication of blue organic electroluminescent devices

[0438] 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.

[0439] 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 isopropyl alcohol and dried. Then, the substrate was cleaned with UV for 5 minutes using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) to produce a substrate on which an ITO transparent electrode was formed. The produced substrate was then transferred to a vacuum deposition machine.

[0440] 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 depositing 98 wt% HI and 2 wt% HAT-CN6 to a thickness of 10 nm on the anode, the hole transport layer was formed by depositing HI to a thickness of 140 nm on the hole injection layer, the light-emitting auxiliary layer was formed by depositing EB to a thickness of 5 nm on the hole transport layer, the light-emitting layer was formed by depositing 98 wt% BH and 2 wt% BD to a thickness of 20 nm on the light-emitting auxiliary layer, the electron transport auxiliary layer was formed by depositing HB to a thickness of 5 nm on the light-emitting layer, the electron transport layer was formed by depositing 30 nm of an electron transport layer material and Liq at a weight ratio of 1:1 on the electron transport auxiliary layer, the electron injection layer was formed by depositing LiF to a thickness of 1 nm on the electron transport layer, and the cathode was formed by depositing Al to a thickness of 100 nm on the electron injection layer. Here, the structure of the HB is shown in Table 3 below, and the electron transport layer material is as shown in Table 4 below.

[0441] HB

[0442] Electron transport layer material Example 22 Compound 1 Example 23 Compound 17 Example 24 Compound 27 Example 25 Compound 39 Example 26 Compound 58 Example 27 Compound 61 Example 28 Compound 96 Example 29 Compound 111 Example 30 Compound 271 Example 31 Compound 287 Example 32 Compound 297 Example 33 Compound 309 Example 34 Compound 328 Example 35 Compound 361 Example 36 Compound 411 Example 37 Compound 441 Example 38 Compound 449 Example 39 Compound 471 Example 40 Compound 468 Example 41 Compound 506 Example 42 Compound 521 Comparative Example 4ET1 Comparative Example 5ET2 Comparative Example 6ET3

[0443]

[0444] [Experimental Example]

[0445] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 21 and Comparative Examples 1 to 3

[0446] For the organic electroluminescent devices manufactured in Examples 1 to 21 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.

[0447] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 14.24527.0 Example 24.34556.2 Example 34.24546.3 Example 44.94596.4 Example 54.24526.1 Example 64.24546.2 Example 74.94537.7 Example 85.04537.6 Example 95.14587.0 Example 104.34557.7 Example 115.14557.4 Example 125.04587.3 Example 134.94557.7 Example 145.04557.4 Example 155.14587.3 Example 164.94557.7 Example 175.24557.4 Example 185.04587.0 Example 195.14587.1 Example 204.24587.3 Example 215.14517.1 Comparative Example 15.64525.3 Comparative Example 25.94535.2 Comparative Example 35.84515.1

[0448] Referring to Table 5 above, the organic electroluminescent devices manufactured in Examples 1 to 21 showed generally superior results in driving voltage and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 1 to 3.

[0449]

[0450] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 22 to 42 and Comparative Examples 4 to 6

[0451] For the organic electroluminescent devices manufactured in Examples 22 to 42 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.

[0452] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 224.34527.2 Example 234.14546.1 Example 244.24536.3 Example 255.14596.4 Example 264.24526.5 Example 275.04516.2 Example 284.64537.6 Example 295.14537.6 Example 305.04527.4 Example 314.34557.7 Example 324.34527.5 Example 335.14567.6 Example 344.94557.7 Example 355.24557.4 Example 365.54547.5 Example 374.34547.7 Example 385.14557.3 Example 394.34587.0 Example 405.04587.1 Example 414.34567.4 Example 425.14517.1 Comparative Example 45.94525.5 Comparative Example 55.64545.2 Comparative Example 65.74525.6

[0453] Referring to Table 6 above, the organic electroluminescent devices manufactured in Examples 22 to 42 showed generally superior results in driving voltage and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 4 to 6.

[0454]

[0455] 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, X 1 Inland X 3 and each independently N or CR 1 And, the above X 1 Inland X 3 At least one of them is N, Y 1 Inland Y 3 are each independently N or CR 2 and the above Y 1 Inland Y 3 At least one of them is N, Above X 1 Inland X 3 and the above Y 1 Inland Y 3 Except for the case where everyone is N, R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 5 to 60 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, a silyl group having 1 to 60 carbon atoms, a phosphine oxide group or a nitrile group having 1 to 60 carbon atoms, each of which may be unsubstituted or substituted, Ar 1 Inland Ar 4 are each independently an alkyl group having 1 to 30 carbon atoms, an aryl group having 5 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a silyl group having 4 to 60 carbon atoms, a phosphine oxide group or a nitrile group having 3 to 60 carbon atoms, each of which may be unsubstituted or substituted.

2. In paragraph 1, X 1 Inland X 3 and each independently N or CR 1 And, the above X 1 Inland X 3 At least one of them is N, Y 1 Inland Y 3 are each independently N or CR 2 and the above Y 1 Inland Y 3 At least one of them is N, Above X 1 Inland X 3 and the above Y 1 Inland Y 3 Except for the case where everyone is N, Above R 1 and R 2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, Above Ar 1 Inland Ar 4 An organic light-emitting compound, wherein each independently represents an aryl group having 5 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, or a phosphine oxide group having 1 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a halogen group, a nitrile group, or a hydroxy group.

3. In paragraph 1, X 1 Inland X 3 and each independently N or CR 1 And, the above X 1 Inland X 3 At least one of them is N, Y 1 Inland Y 3 are each independently N or CR 2 and the above Y 1 Inland Y 3 At least one of them is N, Above X 1 Inland X 3 and the above Y 1 Inland Y 3 Except for the case where everyone is N, Above R 1 and R 2 are each independently hydrogen, Above Ar 1 Inland Ar 4 are each independently one of the following chemical formulas 1-1 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxyl group: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] In the above chemical formulas 1-1 to 1-17, * indicates a site that is bonded to the chemical formula 1 above, R 4 and R 5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R 4 and R 5 can be connected to each other to form a ring.

4. In paragraph 1, Above X 1 Inland X 3 One of them is N and the above Y 1 Inland Y 3 1 is N or the above X 1 Inland X 3 One of them is N and the above Y 1 Inland Y 3 2 are N or the above X 1 Inland X 3 One of them is N and the above Y 1 Inland Y 3 All are N or above X 1 Inland X 3 Two of them are N and the above Y 1 Inland Y 3 2 are N or the above X 1 Inland X 3 Two of them are N and the above Y 1 Inland Y 3 All are N or above X 1 Inland X 3 All are N and above Y 1 Inland Y 3 One of them is N, or X above 1 Inland X 3 All are N and above Y 1 Inland Y 3 Two of them are N; Above R 1 and R 2 are each independently hydrogen; Above Ar 1 and Ar 2 are each independently one of the following chemical formulas 1-1 to 1-3; and Above Ar 3 and Ar 4 are each independently one of the following chemical formulae 1-1 to 1-3, 1-7 to 1-9 and 1-12 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group or a nitrile group: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] In the chemical formulas 1-1 to 1-3, 1-7 to 1-9 and 1-12 to 1-17, * indicates a site that is bonded to the chemical formula 1 above, R 4 and R 5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R 4 and R 5 can be connected to each other to form a ring.

5. In paragraph 1, Above X 1 Inland X 3 Two of them are N and the above Y 1 Inland Y 3 All are N or above X 1 Inland X 3 All are N and above Y 1 Inland Y 3 Two of them are N, or X above 1 Inland X 3 Two of them are N and the above Y 1 Inland Y 3 Two of them are N; Above R 1 and R 2 are each independently hydrogen; Above Ar 1 and Ar 2 is the following chemical formula 1-1; and Above Ar 3 and Ar 4 are each independently one of the following chemical formulae 1-1, 1-2, 1-7, 1-8, 1-14 and 1-15, each of which is unsubstituted or substituted with a halogen group: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-14] [Chemical Formula 1-15] In the above chemical formulas 1-1, 1-2, 1-7, 1-8, 1-14 and 1-15, * indicates a site that is bonded to the chemical formula 1 above, R 4 and R 5 are each independently hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 10 carbon atoms, a halogen group, a nitrile group or a hydroxy group, and R 4 and R 5 can be connected to each other to form a ring.

6. 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 701.

7. In paragraph 1, The above chemical formula 1 is an organic light-emitting compound represented by any one of the following chemical formulas 2 to 6: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] In each of the above chemical formulas 2 to 6, Ar 1 and Ar 2 is a phenyl group, Ar 3 and Ar 4 are each independently a phenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrimidinyl group, or a fluorophenyl group.

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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