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

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2024-0003278, filed January 9, 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] 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.

[0006] 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.

[0007] 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.

[0008] 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.

[0009] Currently, NPB, BCP, Alq3, etc. 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, and (acac)Ir(btp)2, 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) is being used as a phosphorescent host material.

[0010] 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.

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

[0012] Prior art literature

[0013] Republic of Korea Patent Publication No. 10-2022-0142989

[0014] The present invention aims to provide a novel compound that can be used as an organic layer material of an organic electroluminescent device having excellent thermal stability, carrier transport ability, and luminescence ability, specifically, an electron transport layer material and an electron transport auxiliary layer material, and a use thereof.

[0015] In addition, the present invention aims to provide an organic electroluminescent device having significantly improved luminescence performance, driving voltage, lifespan, and efficiency by including the novel organic luminescent compound described above.

[0016] 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.

[0017] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0018] An organic light-emitting compound represented by the following chemical formula 1:

[0019] [Chemical Formula 1]

[0020]

[0021] In the above chemical formula 1,

[0022] X is O or S,

[0023] Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, and at least two of Z1 to Z3 are N,

[0024] Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted,

[0025] R1 to R5 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms, an arylamine group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 1 to 40 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, a cyano group, or a halogen group, each of which may be unsubstituted or substituted,

[0026] At least one of the above R1 to R5 can independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure,

[0027] o, q and r are each independently integers from 0 to 5,

[0028] p and t are each independently integers from 0 to 7,

[0029] s is an integer from 0 to 4,

[0030] u, v and w are each independently integers from 0 to 5,

[0031] The sum of o, p, q, and r is greater than or equal to 4.

[0032] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0033] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0034] The organic light-emitting compound according to the present invention comprises a ring compound having an unshared electron pair with excellent conductivity, a plurality of aryl groups capable of controlling the stability of the molecule and the electron transport rate of the material, and an electron withdrawing group (EWG) with excellent electron transport ability, forming a basic skeleton, and is easy to design into a planar structure or a tilted structure depending on the bonding position of the dibenzo group such as dibenzofuran or dibenzothiophene, and can appropriately control the electron injection rate, and can provide an organic layer material with excellent structural stability and thermal stability with a continuous phenyl structure.

[0035] 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.

[0036] 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.

[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 triphenylenyl group, a chrysenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, etc., but is not limited thereto.

[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 naphthyridyl group, an acenaphthopyridyl group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, purinyl group, indazolyl group, quinolyl group, benzoquinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group,Nitrogen-containing heteroaryl groups including an acridinyl group, a phenanthridyl group, a carbazolyl group, a phenanthrolinyl group, a phenazinyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a pyrazolopyridyl group, a heptaazaphenalenyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples thereof include oxygen-containing heteroaryl groups such as a furyl group, a pyranyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzonaphthofuranyl group, an oxanthrenyl group, a xanthenyl group, and a benzoxanthenyl group; oxygen and sulfur-containing complex heteroaryl groups such as a thiadiazolyl group, an oxadiazolyl group, a phenoxathiinyl group, a benzothienopyrimidinyl group, and a benzofuropyridyl group. In the above heteroaryl group, the number of nuclear atoms can be defined instead of the number of carbon atoms. Here, the number of nuclear atoms includes, in addition to carbon (C) atoms, nitrogen (N), sulfur (S), oxygen (O),It may refer to the number of atoms including one or more heteroatoms selected from the group consisting of phosphorus (P), selenium (Se), and silicon (Si). 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, a cyclooctyl group, a bicyclononyl group, and an adamantyl group, but is not limited thereto.

[0046] 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.

[0047] 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.

[0048] In the present invention, the terms “alkylsilyl group” and “arylsilyl group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogens of silane is substituted with the aforementioned alkyl group or aryl group.

[0049] In the present invention, the terms “alkylamine group” and “arylamine group” may each mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of an amine is substituted with the aforementioned alkyl group or aryl group.

[0050] In the present invention, the term “arylphosphine group” may mean a monovalent functional group derived from a compound in which the aforementioned aryl group is substituted on phosphine.

[0051] In the present invention, the terms “alkylphosphine oxide group” and “arylphosphine oxide group” may each mean a monovalent functional group derived from a compound in which the aforementioned alkyl group or aryl group is substituted on a phosphine oxide.

[0052] In the present invention, the term "substitution" independently means a deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, and a It means being substituted with one or more substituents selected from the group consisting of an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group, and when substituted with multiple substituents, they may be the same or different from each other.

[0053]

[0054] Organic luminescent compounds

[0055] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0056] [Chemical Formula 1]

[0057]

[0058] In the above chemical formula 1,

[0059] X is O or S,

[0060] Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted, and at least two of the Z1 to Z3 are N,

[0061] Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclear atoms, each of which may be unsubstituted or substituted,

[0062] R1 to R5 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, a heterocycloalkyl group having 5 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms, an arylamine group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 1 to 40 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, A cyano group or a halogen group, each of which may be unsubstituted or substituted,

[0063] At least one of the above R1 to R5 can independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure,

[0064] o, q and r are each independently integers from 0 to 5,

[0065] p and t are each independently integers from 0 to 7,

[0066] s is an integer from 0 to 4,

[0067] u, v and w are each independently integers from 0 to 5,

[0068] The sum of o, p, q, and r is greater than or equal to 4.

[0069] In the above, if o is 0, it means that it is a single bond.

[0070] In the above, if p is 0, This means that the benzene ring defined by the number p in the moiety is not substituted, and if a benzene ring defined by the number q or a benzene ring defined by r is present, it means that it is a single bond.

[0071] In the above, if q is 0, It means that the benzene ring defined by the number of moieties or p is not substituted with the benzene ring defined by the number of q, and if the benzene ring defined by r is present, it means that it is a single bond.

[0072] In the above, if r is 0, A moiety means a benzene ring, the number of which is defined by p, or a benzene ring, the number of which is defined by q, on which a benzene ring, the number of which is defined by r, is not substituted.

[0073] In the above, when s, t, u, v or w is each 0, it means that each of R1 to R5 is not substituted with a hydrogen atom present in the benzene ring on which each of R1 to R5 can be substituted.

[0074] Specifically, one or more groups of hydrogen atoms, alkyl groups, cycloalkyl groups, haloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylamine groups, arylamine groups, arylphosphine groups, alkylphosphine oxide groups, arylphosphine oxide groups, cyano groups and halogen groups that may be present in the R', Ar1, Ar2 and R1 to R5 are each independently unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a cyano group having 5 to 30 nuclear atoms. It means being substituted with one or more substituents selected from the group consisting of a heteroaryl group, an alkylsilyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, and a halogen group, and when substituted with multiple substituents, they may be the same or different from each other.

[0075] In one embodiment, in the chemical formula 1,

[0076] X is O or S,

[0077] Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, and at least two of the Z1 to Z3 are N,

[0078] Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, a alkyl group having 1 to 20 carbon atoms, a cyclo ... It may be substituted with an alkylamine group of 20, an arylamine group of 6 to 30 carbon atoms, an arylphosphine group of 6 to 30 carbon atoms, an alkylphosphine oxide group of 1 to 20 carbon atoms, an arylphosphine oxide group of 6 to 30 carbon atoms, a cyano group or a halogen group,

[0079] R1 to R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, A cyano group or a halogen group, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkyl group having 5 to 20 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, It may be substituted with an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group, or a halogen group,

[0080] At least one of the above R1 to R5 can independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure,

[0081] o, q and r are each independently integers from 0 to 5,

[0082] p and t are each independently integers from 0 to 7,

[0083] s is an integer from 0 to 4,

[0084] u, v and w are each independently integers from 0 to 5,

[0085] The sum of o, p, q, and r is greater than or equal to 4.

[0086]

[0087] In the above, if o, p, q, r, s, t, u, v or w is 0, each is as described above.

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

[0089] X is O or S,

[0090] Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, and at least two of the Z1 to Z3 are N,

[0091] Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclear atoms, each of which may be unsubstituted or substituted with a cycloalkyl group having 3 to 20 carbon atoms,

[0092] R1 to R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, or a cyano group, each of which may be unsubstituted or substituted with an aryl group or cyano group having 6 to 30 carbon atoms,

[0093] At least one of the above R1 to R5 can independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure,

[0094] o, q and r are each independently integers from 0 to 5,

[0095] p and t are each independently integers from 0 to 7,

[0096] s is an integer from 0 to 4,

[0097] u, v and w are each independently integers from 0 to 5,

[0098] The sum of o, p, q, and r is greater than or equal to 4.

[0099] In the above, if o, p, q, r, s, t, u, v or w is 0, each is as described above.

[0100] In one embodiment, in the chemical formula 1,

[0101] X is O or S,

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

[0103] Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group or a dibenzothiophenyl group, each of which may be unsubstituted or substituted with a cyclohexyl group,

[0104] R1 to R5 are each independently hydrogen, a butyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a naphthyl group, a triazinyl group, a benzofuranyl group, a benzothiophenyl group or a cyano group, and each of these may be unsubstituted or substituted with a phenyl group or a cyano group.

[0105] At least one of the above R1 to R5 can independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure,

[0106] o, q and r are each independently integers from 0 to 5,

[0107] p and t are each independently integers from 0 to 7,

[0108] s is an integer from 0 to 4,

[0109] u, v and w are each independently integers from 0 to 5,

[0110] The sum of o, p, q and r can be between 4 and 7.

[0111] In the above, if o, p, q, r, s, t, u, v or w is 0, each is as described above.

[0112] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one selected from compounds 1 to 148 below.

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] As a specific example, the compound represented by the above chemical formula 1 may be any one selected from the above compounds 1, 7, 8, 20, 22, 24, 31, 41, 44, 63, 66, 69, 71, 81, 84, 90, 93, 95, 97, 103, 106, 107, 120, 137 and 138.

[0148] The novel organic light-emitting compound of the present invention has a dual EWG type structure in which aromatic groups are connected to carbon positions 2, 4, 5, and 6 of pyrimidine, which is an electron withdrawing group (EWG), and an EWG capable of increasing electron density is additionally combined with the aromatic group connected to carbon position 4, and the structure induces horizontal alignment, thereby increasing rigidity and improving efficiency, thereby enabling improved performance.

[0149] 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.

[0150]

[0151] Organic electroluminescent devices

[0152] 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.

[0153] 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.

[0154] anode

[0155] 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.

[0156] 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.

[0157] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. For example, the anode can be formed by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0158] cathode

[0159] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0160] 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.

[0161] luminescent layer

[0162] 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.

[0163] 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.

[0164] 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.

[0165] electron transport region

[0166] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0167] 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.

[0168] 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.

[0169] 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 forms a basic skeleton by combining an electron withdrawing group (EWG) with excellent electron transport ability with a ring compound having an excellent conductive unshared electron pair and a plurality of aryl groups capable of controlling the stability of the molecule and the electron transport rate of the material, and can be easily designed into a planar structure or a tilted structure depending on the bonding position of the dibenzo group such as dibenzofuran or dibenzothiophene, and can appropriately control the electron injection rate and can be excellent in terms of structural stability and thermal stability due to the continuous phenyl structure. In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0170] 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.

[0171] 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).

[0172] electron transport auxiliary layer

[0173] 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.

[0174] 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 forms a basic skeleton by combining an electron withdrawing group (EWG) with excellent electron transport ability with a ring compound having an excellent conductive unshared electron pair and a plurality of aryl groups capable of controlling the stability of the molecule and the electron transport rate of the material, and can be easily designed into a planar structure or a tilted structure depending on the bonding position of the dibenzo group such as dibenzofuran or dibenzothiophene, and can appropriately control the electron injection rate and can be excellent in terms of structural stability and thermal stability due to the continuous phenyl structure. 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.

[0175] 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.

[0176] hole transport region

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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. It can be used alone or in combination of two or more types.

[0181] 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.

[0182] 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).

[0183] luminescent auxiliary layer

[0184] 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.

[0185] 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.

[0186] 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.

[0187] capping layer

[0188] 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.

[0189] 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).

[0190] 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.

[0191] 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.

[0192]

[0193] 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.

[0194] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

[0195] 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.

[0196] 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.

[0197]

[0198] 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.

[0199]

[0200] [Preparation]

[0201] [Preparation Example 1]: Synthesis of Compound Core 1

[0202] <Step 1> Synthesis of 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-6-phenyldibenzo[b,d]furan

[0203]

[0204] 70 g (262 mmol) of 2-bromo-2'-chloro-1,1'-biphenyl, 79.1 g (275 mmol) of (6-phenyldibenzo-[b,d]furan-2-yl)boronic acid, 15.1 g (13.1 mmol) of Pd(PPh3), and 72.3 g (523.3 mmol) of K2CO3 were added to a mixed solvent of 420 ml of toluene, 210 ml of EtOH, and 210 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 91.5 g (yield 81.2%) of compound 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-6-phenyldibenzo[b,d]furan.

[0205] Mass: [(M+H) + ] : 430

[0206] <Step 2> Synthesis of compound Core 1

[0207]

[0208] 91.5 g (212 mmol) of 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-6-phenyldibenzo[b,d]furan obtained above, 64.7 g (255 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.8 g (11 mmol) of Pd(dppf)Cl2, 62.5 g (637 mmol) of KOAc, and 10.1 g (21 mmol) of Xphos were added to 915 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 81.4 g (yield 73.4%) of compound Core 1.

[0209] Mass: [(M+H) + ] : 522

[0210]

[0211] [Preparation Example 2]: Synthesis of Compound Core 2

[0212] <Step 1> Synthesis of 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-7-phenyldibenzo[b,d]furan

[0213]

[0214] 70 g (262 mmol) of 2-bromo-4'-chloro-1,1'-biphenyl, 79.1 g (275 mmol) of (7-phenyldibenzo[b,d]furan-2-yl)boronic acid, 15.1 g (13.1 mmol) of Pd(PPh3), and 72.3 g (523.3 mmol) of K2CO3 were added to a mixed solvent of 420 ml of toluene, 210 ml of EtOH, and 210 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 95.4 g (yield 84.6%) of the compound 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-7-phenyldibenzo[b,d]furan.

[0215] Mass: [(M+H) + ] : 430

[0216] <Step 2> Synthesis of compound Core 2

[0217]

[0218] The above-obtained compound 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-7-phenyldibenzo[b,d]furan 95.3 g (221 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 67.5 g (265 mmol), Pd(dppf)Cl2 8.1 g (11 mmol), KOAc 65.1 g (663 mmol), and Xphos 10.5 g (22 mmol) were added to 915 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 83.8 g (yield 72.5%) of compound Core 2.

[0219] Mass: [(M+H) + ] : 522

[0220]

[0221] [Preparation Example 3]: Synthesis of Compound Core 3

[0222] <Step 1> Synthesis of 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyldibenzo[b,d]furan

[0223]

[0224] 4-bromo-4'-chloro-1,1'-biphenyl 70 g (262 mmol), (7-phenyldibenzo[b,d]furan-2-yl)boronic acid 79.1 g (275 mmol), Pd(PPh3) 415.1 g (13.1 mmol), and K2CO3 72.3 g (523.3 mmol) were added to a mixed solvent of toluene 420 ml, EtOH 210 ml, and H2O 210 ml, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 89.7 g (yield 79.6%) of compound 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyldibenzo[b,d]furan.

[0225] Mass: [(M+H) + ] : 430

[0226] <Step 2> Synthesis of compound Core 3

[0227]

[0228] 89.7 g (208 mmol) of 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-6-phenyldibenzo[b,d]furan obtained above, 63.4 g (250 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.6 g (10 mmol) of Pd(dppf)Cl2, 61.3 g (624 mmol) of KOAc, and 9.9 g (21 mmol) of Xphos were added to 915 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 75.8 g (yield 69.7%) of compound Core 3.

[0229] Mass: [(M+H) + ] : 522

[0230]

[0231] [Preparation Example 4]: Synthesis of Compound Core 4

[0232] <Step 1> Synthesis of 6-([1,1'-biphenyl]-2-yl)-2-(3'-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan

[0233]

[0234] 60 g (224 mmol) of 3-bromo-3'-chloro-1,1'-biphenyl, 109.8 g (236 mmol) of 2-(6-([1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 133.0 g (11.2 mmol) of Pd(PPh3), and 62.0 g (449 mmol) of K2CO3 were added to a mixed solvent of 360 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 75.6 g (yield 66.5%) of compound 6-([1,1'-biphenyl]-2-yl)-2-(3'-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan.

[0235] Mass: [(M+H) + ] : 506

[0236] <Step 2> Synthesis of compound Core 4

[0237]

[0238] 75.6 g (149 mmol) of the above-obtained 6-([1,1'-biphenyl]-2-yl)-2-(3'-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan, 45.4 g (179 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 5.5 g (7 mmol) of Pd(dppf)Cl2, 43.9 g (447 mmol) of KOAc, and 7.1 g (15 mmol) of Xphos were added to 750 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 55.5 g (yield 62.2%) of compound Core 4.

[0239] Mass: [(M+H) + ] : 598

[0240]

[0241] [Preparation Example 5]: Synthesis of Compound Core 5

[0242] <Step 1> Synthesis of 4-([1,1':2',1''-terphenyl]-4'-yl)-1-chlorodibenzo[b,d]furan

[0243]

[0244] 4-bromo-1-chlorodibenzo[b,d]furan 80 g (284 mmol), 2-([1,1':2',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 106.3 g (298 mmol), Pd(PPh3) 416.4 g (14.2 mmol), and K2CO3 78.5 g (568 mmol) were added to a mixed solvent of toluene 480 ml, EtOH 240 ml, and H2O 240 ml, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added to remove moisture, and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 102.2 g (yield 83.5%) of compound 4-([1,1':2',1''-terphenyl]-4'-yl)-1-chlorodibenzo[b,d]furan.

[0245] Mass: [(M+H) + ] : 430

[0246] <Step 2> Synthesis of compound Core 5

[0247]

[0248] 102 g (237 mmol) of the above-obtained 4-([1,1':2',1''-terphenyl]-4'-yl)-1-chlorodibenzo[b,d]furan, 72.1 g (284 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 8.7 g (12 mmol) of Pd(dppf)Cl2, 69.7 g (710 mmol) of KOAc, and 11.3 g (24 mmol) of Xphos were added to 1000 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 88.2 g (yield 71.3%) of compound Core 5.

[0249] Mass: [(M+H) + ] : 522

[0250]

[0251] [Preparation Example 6]: Synthesis of Compound Core 6

[0252] <Step 1> Synthesis of 1-([1,1':2',1''-terphenyl]-2-yl)-8-chlorodibenzo[b,d]furan

[0253]

[0254] 80 g (284 mmol) of 1-bromo-8-chlorodibenzo[b,d]furan, 106.3 g (298 mmol) of 2-([1,1':2',1''-terphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 16.4 g (14.2 mmol) of Pd(PPh3), and 78.5 g (568 mmol) of K2CO3 were added to a mixed solvent of 480 ml of toluene, 240 ml of EtOH, and 240 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and then filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 94.5 g (yield 77.2%) of compound 1-([1,1':2',1''-terphenyl]-2-yl)-8-chlorodibenzo[b,d]furan.

[0255] Mass: [(M+H) + ] : 430

[0256]

[0257] <Step 2> Synthesis of compound Core 6

[0258]

[0259] 94.5 g (219 mmol) of 1-([1,1':2',1''-terphenyl]-2-yl)-8-chlorodibenzo[b,d]furan obtained above, 66.8 g (263 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 8.0 g (11 mmol) of Pd(dppf)Cl2, 64.6 g (658 mmol) of KOAc, and 10.5 g (22 mmol) of Xphos were added to 1000 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 81.7 g (yield 71.3%) of compound Core 6.

[0260] Mass: [(M+H) + ] : 522

[0261]

[0262] [Preparation Example 7]: Synthesis of Compound Core 7

[0263] <Step 1> Synthesis of 4-([1,1':2',1''-terphenyl]-4'-yl)-6-chlorodibenzo[b,d]furan

[0264]

[0265] 4-bromo-6-chlorodibenzo[b,d]furan 80 g (284 mmol), 2-([1,1':2',1''-terphenyl]-4'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 106.3 g (298 mmol), Pd(PPh3) 416.4 g (14.2 mmol), and K2CO3 78.5 g (568 mmol) were added to a mixed solvent of toluene 480 ml, EtOH 240 ml, and H2O 240 ml, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added to remove moisture, and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 92.9 g (yield 75.9%) of compound 4-([1,1':2',1''-terphenyl]-4'-yl)-6-chlorodibenzo[b,d]furan.

[0266] Mass: [(M+H) + ] : 430

[0267] <Step 2> Synthesis of compound Core 7

[0268]

[0269] 92.9 g (216 mmol) of 4-([1,1':2',1''-terphenyl]-4'-yl)-6-chlorodibenzo[b,d]furan obtained above, 65.7 g (259 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.9 g (11 mmol) of Pd(dppf)Cl2, 63.5 g (647 mmol) of KOAc, and 10.3 g (22 mmol) of Xphos were added to 900 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 74.0 g (yield 65.7%) of compound Core 7.

[0270] Mass: [(M+H) + ] : 522

[0271]

[0272] [Preparation Example 8]: Synthesis of Compound Core 8

[0273] <Step 1> Synthesis of 1-chloro-7-(3',5'-diphenyl-[1,1':2',1''-terphenyl]-3-yl)dibenzo[b,d]furan

[0274]

[0275] 7-(3-bromophenyl)-1-chlorodibenzo[b,d]furan (80 g(224 mmol), 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)-1,3,2-dioxaborolane (101.6 g(235 mmol), Pd(PPh3) (412.9 g(11.2 mmol), and K2CO3 (61.8 g(447 mmol)) were added to a mixed solvent of toluene (480 ml), EtOH (240 ml), and H2O (240 ml) and reacted under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added to remove moisture, and then filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 88.4 g (yield 67.8%) of the compound 1-chloro-7-(3',5'-diphenyl-[1,1':2',1''-terphenyl]-3-yl)dibenzo[b,d]furan.

[0276] Mass: [(M+H) + ] : 582

[0277] <Step 2> Synthesis of compound Core 8

[0278]

[0279] 88.4 g (152 mmol) of 1-chloro-7-(3',5'-diphenyl-[1,1':2',1''-terphenyl]-3-yl)dibenzo[b,d]furan, 46.2 g (182 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 5.5 g (8 mmol) of Pd(dppf)Cl2, 44.6 g (455 mmol) of KOAc, and 7.2 g (15 mmol) of Xphos were added to 900 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 65.7 g (yield 64.3%) of compound Core 8.

[0280] Mass: [(M+H) + ] : 674

[0281]

[0282] [Preparation Example 9]: Synthesis of Compound Core 9

[0283] <Step 1> Synthesis of 3-chloro-6-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)dibenzo-[b,d]furan

[0284]

[0285] 80 g (284 mmol) of 6-bromo-3-chlorodibenzo[b,d]furan, 129 g (298 mmol) of 4,4,5,5-tetramethyl-2-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane, 16.4 g (14.2 mmol) of Pd(PPh3), and 78.5 g (568 mmol) of K2CO3 were added to a mixed solvent of 480 ml of toluene, 240 ml of EtOH, and 240 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and then filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 104.6 g (yield 72.6%) of the compound 3-chloro-6-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)dibenzo[b,d]furan.

[0286] Mass: [(M+H) + ] : 506

[0287] <Step 2> Synthesis of compound Core 9

[0288]

[0289] 104.6 g (206 mmol) of 3-chloro-6-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)dibenzo[b,d]furan obtained above, 62.9 g (248 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.5 g (10 mmol) of Pd(dppf)Cl2, 60.7 g (619 mmol) of KOAc, and 9.8 g (21 mmol) of Xphos were added to 1000 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 90.3 g (yield 73.1%) of compound Core 9.

[0290] Mass: [(M+H) + ] : 598

[0291]

[0292] [Preparation Example 10]: Synthesis of Compound Core 10

[0293] <Step 1> Synthesis of 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)-7-chlorodibenzo[b,d]furan

[0294]

[0295] 80 g (284 mmol) of 2-bromo-7-chlorodibenzo[b,d]furan, 151.7 g (298 mmol) of 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 16.4 g (14.2 mmol) of Pd(PPh3), and 78.5 g (568 mmol) of K2CO3 were added to a mixed solvent of 480 ml of toluene, 240 ml of EtOH, and 240 ml of H2O, and reacted while heating and stirring under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, and MgSO4 was added to remove moisture and filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 123.9 g (yield 74.8%) of compound 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)-7-chlorodibenzo-[b,d]furan.

[0296] Mass: [(M+H) + ] : 582

[0297] <Step 2> Synthesis of compound Core 10

[0298]

[0299] 123.9 g (212 mmol) of 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)-7-chlorodibenzo[b,d]furan, 64.7 g (255 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.8 g (11 mmol) of Pd(dppf)Cl2, 62.6 g (637 mmol) of KOAc, and 10.1 g (21 mmol) of Xphos obtained above were added to 1,4-Dioxane 1200 ml and reacted while heating and stirring under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 104.8 g (yield 73.1%) of compound Core 10.

[0300] Mass: [(M+H) + ] : 674

[0301]

[0302] [Synthesis example]

[0303] [Synthesis Example 1]: Synthesis of Compound 1

[0304]

[0305] 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine 20.0 g(1 eq, 41 mmol), Core 1 27.4 g(1.10 eq, 52.0 mmol) of compound synthesized in Preparation Example 1, Pd(OAc) 20.3 g(0.03 eq, 1.4 mmol), Cs2CO3 31.0 g(2.0 eq, 95.3 mmol), and Xphos 1.4 g(0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 28.0 g (yield 75.4%) of compound 1.

[0306] Mass: [(M+H) + ] : 779

[0307]

[0308] [Synthesis Example 2]: Synthesis of Compound 7

[0309]

[0310] 20 g (1 eq, 47.7 mmol) of 4-(2'-chloro-[1,1'-biphenyl]-2-yl)-2,6-diphenylpyrimidine, 27.4 g (1.10 eq, 52.5 mmol) of Core 2 synthesized in Preparation Example 2, 20.3 g (0.03 eq, 1.4 mmol) of Pd(OAc), 31.1 g (2.0 eq, 95.5 mmol) of Cs2CO3, and 1.4 g (0.6 eq 2.9 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 26.7 g (yield 71.9%) of compound 7.

[0311] Mass: [(M+H) + ] : 778

[0312]

[0313] [Synthesis Example 3]: Synthesis of Compound 8

[0314]

[0315] 2-(2'-chloro-[1,1':4',1''-terphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine 20 g(1 eq, 40.3 mmol), Core 2 23.2 g(1.10 eq, 44.4 mmol) synthesized in Preparation Example 2, Pd(OAc) 20.3 g(0.03 eq, 1.2 mmol), Cs2CO3 26.3 g(2.0 eq, 80.6 mmol), and Xphos 1.2 g(0.6 eq 2.4 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 23.6 g (yield 68.3%) of compound 8.

[0316] Mass: [(M+H) + ] : 855

[0317]

[0318] [Synthesis Example 4]: Synthesis of Compound 20

[0319]

[0320] 20 g (1 eq, 30.7 mmol) of 6,6'-(5-chloro-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine), 17.7 g (1.10 eq, 33.8 mmol) of Core 3 synthesized in Preparation Example 3, 20.2 g (0.03 eq, 0.9 mmol) of Pd(OAc), 20.0 g (2.0 eq, 61.4 mmol) of Cs2CO3, and 0.9 g (0.6 eq 1.8 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 15.0 g (yield 48.3%) of compound 20.

[0321] Mass: [(M+H) + ] : 1010

[0322]

[0323] [Synthesis Example 5]: Synthesis of Compound 22

[0324]

[0325] 2-(2'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 47.6 mmol), Core 1 27.4 g (1.10 eq, 52.4 mmol) synthesized in Preparation Example 1, Pd(OAc) 20.3 g (0.03 eq, 1.4 mmol), Cs2CO3 31.0 g (2.0 eq, 95.3 mmol), and Xphos 1.4 g (0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 28.3 g (yield 76.3%) of compound 22.

[0326] Mass: [(M+H) + ] : 779

[0327]

[0328] [Synthesis Example 6]: Synthesis of Compound 24

[0329]

[0330] 20 g (1 eq, 45.1 mmol) of 6-chloro-4'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-carbonitrile, 25.9 g (1.10 eq, 49.6 mmol) of Core 1 synthesized in Preparation Example 1, 20.3 g (0.03 eq, 1.4 mmol) of Pd(OAc), 29.4 g (2.0 eq, 90.3 mmol) of Cs2CO3, and 1.3 g (0.6 eq 2.7 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 19.0 g of compound 24 (yield 52.3%).

[0331] Mass: [(M+H) + ] : 803

[0332]

[0333] [Synthesis Example 7]: Synthesis of Compound 31

[0334]

[0335] 20 g (1 eq, 58.3 mmol) of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, 33.5 g (1.10 eq, 64.2 mmol) of Core 3 synthesized in Preparation Example 3, 20.4 g (0.03 eq, 1.8 mmol) of Pd(OAc), 38.0 g (2.0 eq, 116.7 mmol) of Cs2CO3, and 1.7 g (0.6 eq 3.5 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 31.5 g of compound 31 (yield 76.8%).

[0336] Mass: [(M+H) + ] : 702

[0337]

[0338] [Synthesis Example 8]: Synthesis of Compound 41

[0339]

[0340] 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 58.2 mmol), Core 4 38.3 g (1.10 eq, 64.0 mmol) synthesized in Preparation Example 4, Pd(OAc) 20.4 g (0.03 eq, 1.7 mmol), Cs2CO3 37.9 g (2.0 eq, 116.3 mmol), and Xphos 1.7 g (0.6 eq 3.5 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 31.0 g (yield 68.5%) of compound 41.

[0341] Mass: [(M+H) + ] : 779

[0342]

[0343] [Synthesis Example 9]: Synthesis of Compound 44

[0344]

[0345] 20 g (1 eq, 58.3 mmol) of 4-(2-chlorophenyl)-2,6-diphenylpyrimidine, 38.4 g (1.10 eq, 64.2 mmol) of Core 4 synthesized in Preparation Example 4, 20.4 g (0.0 3 eq, 1.8 mmol) of Pd(OAc), 38.0 g (2.0 eq, 116.7 mmol) of Cs2CO3, and 1.7 g (0.6 eq 3.5 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under heating and reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 31.9 g of compound 44 (yield 70.3%).

[0346] Mass: [(M+H) + ] : 778

[0347]

[0348] [Synthesis Example 10]: Synthesis of Compound 63

[0349]

[0350] 20 g (1 eq, 47.7 mmol) of 4-(2'-chloro-[1,1'-biphenyl]-4-yl)-2,6-diphenylpyrimidine, 27.4 g (1.10 eq, 52.5 mmol) of Core 5 synthesized in Preparation Example 5, 20.3 g (0.03 eq, 1.4 mmol) of Pd(OAc), 31.1 g (2.0 eq, 95.5 mmol) of Cs2CO3, and 1.4 g (0.6 eq 2.9 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 25.1 g (yield 67.4%) of compound 63.

[0351] Mass: [(M+H) + ] : 778

[0352]

[0353] [Synthesis Example 11]: Synthesis of Compound 66

[0354]

[0355] 20 g (1 eq, 30.7 mmol) of 6,6'-(3'-chloro-[1,1'-biphenyl]-3,5-diyl)bis(2,4-diphenyl-1,3,5-triazine), 17.7 g (1.10 eq, 33.8 mmol) of Core 6 synthesized in Preparation Example 6, 20.2 g (0.03 eq, 0.9 mmol) of Pd(OAc), 20.0 g (2.0 eq, 61.4 mmol) of Cs2CO3, and 0.9 g (0.6 eq 1.8 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 16.4 g of compound 66 (yield 52.8%).

[0356] Mass: [(M+H) + ] : 1010

[0357]

[0358] [Synthesis Example 12]: Synthesis of Compound 69

[0359]

[0360] 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 47.6 mmol), Core 5 compound synthesized in Preparation Example 5 27.4 g (1.10 eq, 52.4 mmol), Pd(OAc) 20.3 g (0.03 eq, 1.4 mmol), Cs2CO3 31.0 g (2.0 eq, 95.4 mmol), and Xphos 1.4 g (0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 24.0 g (yield 64.7%) of compound 69.

[0361] Mass: [(M+H) + ] : 779

[0362]

[0363] [Synthesis Example 13]: Synthesis of Compound 71

[0364]

[0365] 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 47.6 mmol), Core 6 compound synthesized in Preparation Example 6 27.4 g (1.10 eq, 52.4 mmol), Pd(OAc) 20.3 g (0.03 eq, 1.4 mmol), Cs2CO3 31.0 g (2.0 eq, 95.3 mmol), and Xphos 1.4 g (0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 27.2 g of compound 71 (yield 73.3%).

[0366] Mass: [(M+H) + ] : 779

[0367]

[0368] [Synthesis Example 14]: Synthesis of Compound 81

[0369]

[0370] 20 g (1 eq, 47.7 mmol) of 4-(4'-chloro-[1,1'-biphenyl]-2-yl)-2,6-diphenylpyrimidine, 27.4 g (1.10 eq, 52.5 mmol) of Core 6 synthesized in Preparation Example 6, 20.3 g (0.03 eq, 1.4 mmol) of Pd(OAc), 31.1 g (2.0 eq, 95.5 mmol) of Cs2CO3, and 1.4 g (0.6 eq 2.9 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 25.5 g of compound 81 (yield 68.5%).

[0371] Mass: [(M+H) + ] : 778

[0372]

[0373] [Synthesis Example 15]: Synthesis of Compound 84

[0374]

[0375] 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine 20 g(1 eq, 47.6 mmol), compound Core 7 synthesized in Preparation Example 7 27.4 g(1.10 eq, 52.4 mmol), Pd(OAc) 20.3 g(0.03 eq, 1.4 mmol), Cs2CO3 31.0 g(2.0 eq, 95.3 mmol), and Xphos 1.4 g(0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 28.1 g (yield 75.6%) of compound 84.

[0376] Mass: [(M+H) + ] : 779

[0377]

[0378] [Synthesis Example 16]: Synthesis of Compound 90

[0379]

[0380] 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine 20 g(1 eq, 47.6 mmol), compound Core 7 synthesized in Preparation Example 7 27.4 g(1.10 eq, 52.4 mmol), Pd(OAc) 20.3 g(0.03 eq, 1.4 mmol), Cs2CO3 31.0 g(2.0 eq, 95.3 mmol), and Xphos 1.4 g(0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 26.6 g (yield 71.6%) of compound 90.

[0381] Mass: [(M+H) + ] : 779

[0382]

[0383] [Synthesis Example 17]: Synthesis of Compound 93

[0384]

[0385] 20 g (1 eq, 47.6 mmol) of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, 27.4 g (1.10 eq, 52.4 mmol) of Core 6 synthesized in Preparation Example 6, 20.3 g (0.03 eq, 1.4 mmol) of Pd(OAc), 31.0 g (2.0 eq, 95.3 mmol) of Cs2CO3, and 1.4 g (0.6 eq 2.9 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 26.2 g (yield 70.7%) of compound 93.

[0386] Mass: [(M+H) + ] : 779

[0387]

[0388] [Synthesis Example 18]: Synthesis of Compound 95

[0389]

[0390] 20 g (1 eq, 33.5 mmol) of 4''-chloro-5'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-phenyl-[1,1':2',1''-terphenyl]-4-carbonitrile, 19.2 g (1.10 eq, 36.8 mmol) of Core 7, synthesized in Preparation Example 7, 20.2 g (0.03 eq, 1.0 mmol) of Pd(OAc), 21.8 g (2.0 eq, 67.0 mmol) of Cs2CO3, and 1.0 g (0.6 eq 2.0 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and reacted while heating and stirring under reflux for 4 hours. After the reaction was completed, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 17.2 g (yield 53.7%) of compound 95.

[0391] Mass: [(M+H) + ] : 956

[0392]

[0393] [Synthesis Example 19]: Synthesis of Compound 97

[0394]

[0395] 20 g (1 eq, 58.3 mmol) of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, 43.3 g (1.10 eq, 64.2 mmol) of Core 8 synthesized in Preparation Example 8, 20.4 g (0.03 eq, 1.8 mmol) of Pd(OAc), 38.0 g (2.0 eq, 116.7 mmol) of Cs2CO3, and 1.7 g (0.6 eq 3.5 mmol) of Xphos were added to a mixed solvent of 120 ml of toluene, 60 ml of EtOH, and 60 ml of H2O, and the mixture was stirred under reflux and heated for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 27.8 g (yield 55.8%) of compound 97.

[0396] Mass: [(M+H) + ] : 854

[0397]

[0398] [Synthesis Example 20]: Synthesis of Compound 103

[0399]

[0400] 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 58.2 mmol), Core 9 compound synthesized in Preparation Example 9 38.3 g (1.10 eq, 64.0 mmol), Pd(OAc) 20.4 g (0.03 eq, 1.7 mmol), Cs2CO3 37.9 g (2.0 eq, 116.3 mmol), and Xphos 1.7 g (0.6 eq 3.5 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 28.9 g (yield 63.8%) of compound 103.

[0401] Mass: [(M+H) + ] : 779

[0402]

[0403] [Synthesis Example 21]: Synthesis of Compound 106

[0404]

[0405] 2-(3-chloro-5-(2,6-diphenylpyrimidin-4-yl)phenyl)-4,6-diphenyl-1,3,5-triazine 20 g(1 eq, 34.8 mmol), Core 8 compound synthesized in Preparation Example 8 25.9 g(1.10 eq, 38.3 mmol), Pd(OAc) 20.2 g(0.03 eq, 1.0 mmol), Cs2CO3 22.7 g(2.0 eq, 69.7 mmol), and Xphos 1.0 g(0.6 eq, 2.1 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 16.5 g (yield 43.6%) of compound 106.

[0406] Mass: [(M+H) + ] : 1085

[0407]

[0408] [Synthesis Example 22]: Synthesis of Compound 107

[0409]

[0410] 2-(5-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 47.6 mmol), compound Core 9 synthesized in Preparation Example 9 31.4 g (1.10 eq, 52.4 mmol), Pd(OAc) 20.3 g (0.03 eq, 1.4 mmol), Cs2CO3 31.0 g (2.0 eq, 95.3 mmol), and Xphos 1.4 g (0.6 eq 2.9 mmol) were added to a mixed solvent of toluene 120 ml, EtOH 60 ml, and H2O 60 ml, and reacted while stirring and heating under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 23.8 g (yield 58.3%) of compound 107.

[0411] Mass: [(M+H) + ] : 855

[0412]

[0413] [Synthesis Example 23]: Synthesis of Compound 120

[0414]

[0415] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine 20 g (1 eq, 58.2 mmol), compound Core 8 41.2 g (1.05 eq, 61.1 mmol) synthesized in Preparation Example 8, Pd(PPh3) 43.4 g (2.9 mmol) and K2CO3 16.1 g (116.3 mmol) were added to a mixed solvent of toluene 120 ml and H2O 60 ml and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain compound 120 31.0 g (yield 62.3%).

[0416] Mass: [(M+H) + ] : 855

[0417]

[0418] [Synthesis Example 24]: Synthesis of Compound 137

[0419]

[0420] 2-chloro-4,6-di(naphthalen-1-yl)-1,3,5-triazine 20 g (1 eq, 54.4 mmol), compound Core 10 synthesized in Preparation Example 10 38.5 g (1.05 eq, 57.1 mmol), Pd(PPh3) 43.1 g (2.7 mmol), and K2CO3 15.0 g (108.7 mmol) were added to a mixed solvent of toluene 120 ml and H2O 60 ml and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain compound 137 29.0 g (yield 60.7%).

[0421] Mass: [(M+H) + ] : 879

[0422]

[0423] [Synthesis Example 25]: Synthesis of Compound 138

[0424]

[0425] 2-chloro-4,6-diphenyl-1,3,5-triazine 20 g (1 eq, 74.7 mmol), compound Core 10 52.9 g (1.05 eq, 78.4 mmol) synthesized in Preparation Example 10, Pd(PPh3) 44.3 g (3.7 mmol) and K2CO3 20.6 g (149.4 mmol) were added to a mixed solvent of T toluene 120 ml and H2O 60 ml and reacted while heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, MgSO4 was added and filtered. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain compound 138 42.7 g (yield 73.2%).

[0426] Mass: [(M+H) + ] : 779

[0427]

[0428] [Examples and Comparative Examples] - 1

[0429] [Examples 1 to 5 and Comparative Example 1]: Fabrication of a blue organic electroluminescent device

[0430] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0431] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0432] An organic electroluminescent device was manufactured by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing HT-1 and HAT-CN in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing HT-1 in a thickness of 1400 Å on the hole injection layer, the light-emitting auxiliary layer was formed by depositing HT-2 in a thickness of 50 Å 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 200 Å, the electron transport auxiliary layer was formed by depositing ET-2 in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing an electron transport layer material and LiQ in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. It was formed by depositing with a thickness of Å. Here, the structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2, and LiQ are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0433] HT-1 HAT-CN HT-2 BH BD ET-2 LiQ

[0434] Electron transport layer material Example 1 Compound 20 Example 2 Compound 24 Example 3 Compound 66 Example 4 Compound 95 Example 5 Compound 106 Comparative Example 1 ET-1

[0435]

[0436] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 5 and Comparative Example 1

[0437] For the organic electroluminescent devices manufactured in Examples 1 to 5 and Comparative Example 1, the driving voltage, luminescence (EL) peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 3 below.

[0438] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 14.5 46 0 6.7 Example 24.4 46 16.6 Example 34.3 46 0 6.5 Example 44.2 45 9 6.6 Example 54.1 46 16.4 Comparative example 14.8 46 0 5.9

[0439] Referring to Table 3 above, the blue organic electroluminescent devices manufactured in Examples 1 to 5 using the compound according to the present invention as an electron transport layer material showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device manufactured in Comparative Example 1 using ET-1, a conventional electron transport layer material.

[0440]

[0441] [Examples and Comparative Examples] - 2

[0442] [Examples 6 to 25 and Comparative Examples 2 to 4]: Fabrication of blue organic electroluminescent devices

[0443] 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.

[0444] 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.

[0445] 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 HT-1 and HAT-CN in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing HT-1 in a thickness of 1400 Å on the hole injection layer, the light-emitting auxiliary layer was formed by depositing HT-2 in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing 98:2 BH and BD in a weight ratio of 200 Å 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 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing ET-1 and LiQ in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. It was formed by depositing with a thickness of Å. Here, the structures of HT-1, HAT-CN, HT-2, BH, BD, and LiQ are as shown in Table 1 above, the structure of ET-1 is as shown in Table 2 above, and the electron transport auxiliary layer materials are shown in Table 4 below.

[0446] Electron transport auxiliary layer material Example 6 Compound 1 Example 7 Compound 7 Example 8 Compound 8 Example 9 Compound 22 Example 10 Compound 31 Example 11 Compound 41 Example 12 Compound 44 Example 13 Compound 63 Example 14 Compound 69 Example 15 Compound 71 Example 16 Compound 81 Example 17 Compound 84 Example 18 Compound 90 Example 19 Compound 93 Example 20 Compound 97 Example 21 Compound 103 Example 22 Compound 107 Example 23 Compound 120 Example 24 Compound 137 Example 25 Compound 138 Comparative Example 2ET-3 Comparative Example 3ET-4 Comparative Example 4ET-5

[0447]

[0448] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 6 to 25 and Comparative Examples 2 to 4

[0449] For the organic electroluminescent devices manufactured in Examples 6 to 25 and Comparative Examples 2 to 4, 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.

[0450] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 64.44616.4 Example 74.44606.5 Example 84.04616.4 Example 94.44626.9 Example 104.34597.0 Example 114.34586.6 Example 124.24626.8 Example 134.34636.3 Example 144.44586.3 Example 154.34606.4 Example 164.44606.6 Example 174.14597.0 Example 184.44606.5 Example 193.94606.0 Example 204.34626.5 Example 214.14606.7 Example 224.24617.1 Example 234.44626.9 Example 244.24616.5 Example 254.44606.8 Comparative Example 24.64606.0 Comparative Example 34.74616.1 Comparative Example 44.64605.7

[0451] Referring to Table 5 above, the blue organic electroluminescent devices manufactured in Examples 6 to 25 using the compound according to the present invention as an electron transport layer material showed overall superior results in the evaluation of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices manufactured in Comparative Examples 2 to 4.

[0452]

[0453] 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 is O or S, Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, and at least two of said Z1 to Z3 are N, Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms, each of which may be unsubstituted or substituted, R1 to R5 are each independently hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a heterocycloalkyl group having 2 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylamine group having 1 to 40 carbon atoms, an arylamine group having 6 to 60 carbon atoms, an arylphosphine group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 1 to 40 carbon atoms, an arylphosphine oxide group having 6 to 60 carbon atoms, a cyano group or a halogen group, each of which may be unsubstituted or substituted, At least one of the above R1 to R5 may independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure, o, q and r are each independently an integer from 0 to 5, p and t are each independently an integer from 0 to 7, s is an integer from 0 to 4, u, v and w are each independently integers from 0 to 5, The sum of o, p, q, and r is greater than or equal to 4.

2. In paragraph 1, The above X is O or S, The above Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, and at least two of the above Z1 to Z3 are N, The above Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, and each of them is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, or a It may be substituted with an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group, The above R1 to R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group, each of which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a carbon atom, a hydrogen atom, or a halogen group. which may be substituted with a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, an arylamine group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a cyano group or a halogen group, At least one of the above R1 to R5 may independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure, The above o, q and r are each independently an integer from 0 to 5, The above p and t are each independently an integer from 0 to 7, The above s is an integer from 0 to 4, The above u, v and w are each independently integers from 0 to 5, An organic luminescent compound wherein the sum of o, p, q and r is 4 or more.

3. In paragraph 1, The above X is O or S, The above Z1 to Z3 are each independently N or CR', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, and at least two of the above Z1 to Z3 are N, The above Ar1 and Ar2 are each independently hydrogen, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms, and each of them may be unsubstituted or substituted with a cycloalkyl group having 3 to 20 carbon atoms. The above R1 to R5 are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms or a cyano group, and each of them may be unsubstituted or substituted with an aryl group or cyano group having 6 to 30 carbon atoms. At least one of the above R1 to R5 may independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure, The above o, q and r are each independently an integer from 0 to 5, The above p and t are each independently an integer from 0 to 7, The above s is an integer from 0 to 4, The above u, v and w are each independently integers from 0 to 5, An organic luminescent compound wherein the sum of o, p, q and r is 4 or more.

4. In paragraph 1, The above X is O or S, The above Z1 to Z3 are each independently N or CH, and at least two of the above Z1 to Z3 are N, The above Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group or a dibenzothiophenyl group, and each of them may be unsubstituted or substituted with a cyclohexyl group, The above R1 to R5 are each independently hydrogen, a butyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a naphthyl group, a triazinyl group, a benzofuranyl group, a benzothiophenyl group or a cyano group, and each of them may be unsubstituted or substituted with a phenyl group or a cyano group. At least one of the above R1 to R5 may independently combine with at least one group bonded to an adjacent carbon atom to form a condensed ring structure, The above o, q and r are each independently an integer from 0 to 5, The above p and t are each independently an integer from 0 to 7, The above s is an integer from 0 to 4, The above u, v and w are each independently integers from 0 to 5, An organic luminescent compound wherein the sum of o, p, q and r is 4 to 7.

5. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound selected from compounds 1 to 148 below.

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

7. In paragraph 6, 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.

8. In paragraph 7, 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.

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

10. In paragraph 9, 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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