Organic light-emitting compounds and organic electroluminescent devices comprising organic light-emitting compounds

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 including the same, which can have high current efficiency and low driving voltage.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2023-0180717, filed with the Korean Intellectual Property Office on December 13, 2023, the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] The embodiments disclosed herein relate to novel organic light-emitting compounds and organic electroluminescent devices comprising the novel organic light-emitting compounds. Background Technology

[0004] Since Bernanose first discovered the luminescence of organic films in the 1950s, research was conducted in 1965 on organic electroluminescent (EL) devices based on blue electroluminescence using anthracene single crystals. In 1987, Tang proposed an organic electroluminescent device with a stacked structure, which was divided into functional layers including a hole layer and a light-emitting layer. Since then, in order to endow devices with high efficiency and long lifetime, organic electroluminescent devices containing organic layers with their own characteristics, as well as specific materials for the devices, have been developed.

[0005] When a voltage is applied between the two electrodes in an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes combine with the electrons, excitons are formed. When the excitons return to the ground state, they emit light. In this case, the materials used for the organic material layer can be classified according to their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0006] Light-emitting materials used in organic electroluminescent devices can be classified into blue, green, and red light-emitting materials based on the color of the light emitted. Additionally, yellow and orange light-emitting materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as light-emitting materials to improve color purity and luminous efficiency through energy transfer.

[0007] Dopant materials can be classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms (such as Ir and Pt). Because such phosphorescent materials can theoretically increase luminescence efficiency to four times that of fluorescent materials, extensive research is being conducted on both phosphorescent host materials and phosphorescent dopant materials.

[0008] Anthracene derivatives such as NPB, BCP, and Alq3 are widely considered as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as luminescent layer materials. In particular, among luminescent layer materials, Ir-containing metal complexes (such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2) offer advantages in improving efficiency and are used as blue, green, and red phosphorescent dopants, while 4,4-dicarbazolium biphenyl (CBP) is used as the host phosphorescent material.

[0009] Therefore, conventional organic layer materials are advantageous in terms of light-emitting properties, but they are not satisfactory in terms of improving the lifetime of organic electroluminescent devices due to their low glass transition temperature and therefore very poor thermal stability.

[0010] Therefore, there is a need to develop organic layer materials with excellent performance.

[0011] Existing technical documents

[0012] Korean Patent Publication No. 10-2019-0111824 Summary of the Invention

[0013] Technical issues

[0014] The embodiments disclosed herein provide novel compounds with improved electron transport capabilities and their uses, which can be used as materials for organic layers in organic electroluminescent devices, particularly as materials for electron transport layers and electron transport auxiliary layers.

[0015] The embodiments disclosed herein provide organic electroluminescent devices comprising novel organic light-emitting compounds that have significantly improved luminescent performance, driving voltage, lifetime, and efficiency.

[0016] It should be noted that the purpose of this disclosure is not limited to the purposes mentioned above, and other purposes not mentioned in this disclosure will be clearly understood by those skilled in the art from the following description.

[0017] Technical solution

[0018] Embodiments of this disclosure provide organic light-emitting compounds represented by Formula 1:

[0019] Organic light-emitting compounds represented by Equation 1:

[0020] [Formula 1]

[0021]

[0022] In Equation 1,

[0023] A is a heteroarylene group containing 2 to 60 carbon atoms and having at least two nitrogen atoms, which may be unsubstituted or substituted.

[0024] R is hydrogen, an alkyl group containing 1 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a haloalkyl group containing 1 to 40 carbon atoms, a heterocycloalkyl group containing 2 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylamine group containing 1 to 40 carbon atoms, an arylamine group containing 6 to 60 carbon atoms, an arylphosphin group containing 6 to 60 carbon atoms, an alkylphosphine oxide group containing 1 to 40 carbon atoms, an arylphosphine oxide group containing 6 to 60 carbon atoms, a carbonyl group, a cyano group, or a halogen group, each of which may be unsubstituted or substituted.

[0025] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the above groups is independently a single bond, an alkylene group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, or a heteroaryl group containing 2 to 60 carbon atoms, and each of these groups is either unsubstituted or substituted.

[0026] Ar1 to Ar3 are each independently an aryl group containing 6 to 60 carbon atoms, or a heteroaryl group containing 2 to 60 carbon atoms, wherein each of the above groups is unsubstituted or substituted, and

[0027] n is an integer from 0 to 5, where when n is from 2 to 5, each of the multiple L5 and R is independently the same or different from each other.

[0028] The embodiments disclosed herein provide an organic electroluminescent device comprising an organic light-emitting compound.

[0029] The embodiments disclosed herein provide the use of organic light-emitting compounds in organic electroluminescent devices.

[0030] Beneficial effects

[0031] The organic light-emitting compound disclosed herein has a double EWG-type structure, wherein an aromatic group is bonded to the 2-, 4-, 5-, and 6-carbon positions of a pyrimidine as an electron-withdrawing group (EWG), and an additional EWG capable of increasing electron density is further bonded to an aromatic group bonded to the 4-carbon position. Such a structure induces horizontal orientation to increase rigidity and improve efficiency, thereby providing an organic layer material with improved performance.

[0032] Furthermore, organic electroluminescent devices containing organic light-emitting compounds according to this disclosure can achieve low driving voltage and greatly improve luminous performance, lifetime and efficiency, thus enabling more effective application in full-color display panels and the like.

[0033] The effects of this disclosure are not limited to those described above, and other unmentioned technical effects will become apparent to those skilled in the art from the following description. Detailed Implementation

[0034] The advantages and features of this disclosure, as well as methods for implementing them, will become clear from the embodiments described in the following detailed description. However, this disclosure is not limited to these embodiments and may be embodied in different forms. These embodiments are presented merely to provide a full and complete understanding of this disclosure and to fully inform those skilled in the art of the technical concepts of this disclosure, which is limited only by the scope of the claims.

[0035] The terminology used herein is provided merely to illustrate exemplary embodiments and should not be construed as limiting the scope of this disclosure. Unless the context clearly indicates otherwise, the singular form is intended to include the plural form as well. It will be further understood that the terms “comprises” and / or “comprising” as used herein do not exclude the presence or addition of one or more other components besides those mentioned.

[0036] Unless otherwise defined, all terms used herein (including technical or scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Furthermore, terms identical to those defined in a general dictionary should be interpreted as having the same meaning as in the context of the relevant art, and should not be interpreted as having an ideal or overly formal meaning unless expressly defined in this disclosure.

[0037] The embodiments of this disclosure will be described in detail below.

[0038] Before proceeding, the meanings of the terms used herein will be briefly described. However, the explanations of the terms are provided to facilitate a better understanding of this disclosure, and unless the context clearly indicates that these terms are used to limit the scope of this disclosure, they should not be construed as limiting the technical ideas of this disclosure.

[0039] As used herein, the term "aryl" refers to a monovalent functional group derived from aromatic hydrocarbons. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, anthraceneyl, tetraphenyl, pyrene, tolyl, biphenyl, terphenyl, triphenylenyl, chrysenyl (or trefoil), spirodifluorenyl, fluorenyl, perylene, indole, azulel, hepta-enyl, phenalenyl, and phenanthrenyl groups. Furthermore, the term "arylene" refers to a divalent functional group derived from aromatic hydrocarbons.

[0040] As used herein, the term "heteroaryl" can refer to a monovalent functional group derived from an aromatic heterocycle having a monocyclic or fused-ring structure, and a heteroaryl can include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), or silicon (Si) as a heteroatom, in addition to a carbon atom. Specific examples of heteroaryl include nitrogen-containing heteroaryl groups, including pyrrole, pyridinyl, pyridazinyl, triazinyl, pyrimidinyl, pyrazinyl, naphthidyl, acenaphthenic, triazolyl, tetrazolyl, benzotriazolyl, pyrazolyl, imidazole, benzimidazole, indolyl, isoyindolyl, and indolizinyl. Groups, also known as indene, purine, indazole, quinolinyl, benzoquinolinyl, isoquinolinyl, quinazinyl, phthalazinyl, naphthidyl, quinoxolinyl, quinazolinyl, terazinyl, pteridinyl, imidazotriazinyl, acridineyl, phenanthridineyl, carbazole, phenanthridineyl, phenazinyl, imidazopyridyl, imidazopyrimidyl, pyrazolidineyl, heptaazaphenafenenyl, etc.; sulfur-containing heteroaryl groups, including thienyl, benzothienyl, dibenzothienyl, benzonaphthothienyl, etc.; oxygen-containing heteroaryl groups, including furanyl, pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, oxanthrenyl (or oxanthrenyl group), xanthenyl (xanthenyl) Groups, benzoxanthryl, etc.; heteroaryl groups containing combinations of oxygen and sulfur, including thiadiazolyl, oxadiazolyl, phenoxthial, benzothiophenepyrimidinyl, benzofuranopyridinyl, etc. Furthermore, the term "heteroaryl" refers to a divalent functional group derived from an aromatic heterocycle having a monocyclic or fused-ring structure, and heteroaryl groups may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), or silicon (Si) as a heteroatom, in addition to a carbon atom. Heteroaryl and heteroaryl groups can be defined by the number of nuclear atoms rather than the number of carbon atoms. Here, the number of nuclear atoms can refer to the number of one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si), as well as carbon (C) atoms. For example, the number of nuclear atoms in heteroaryl and heteroaryl groups can be 5 to 60, 5 to 30, or 5 to 20.

[0041] As used herein, the term "alkyl" refers to a monovalent functional group derived from a saturated hydrocarbon having a straight-chain or branched structure. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl, n-hexyl, 1-methyl-2-ethylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl, 1-propylpropyl, 1-methylbutyl, 2-methylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 2-methylpentyl, 3-methylpentyl, etc. In addition, the term "alkylene" refers to a divalent functional group derived from a saturated hydrocarbon having a straight-chain or branched structure.

[0042] As used herein, the term "cycloalkyl" refers to a monovalent functional group derived from a saturated hydrocarbon having a cyclic structure. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclononyl, adamantyl, etc.

[0043] As used herein, the term "heterocyclic alkyl" can refer to a monovalent functional group derived from a saturated hydrocarbon having a cyclic structure, and a heterocyclic alkyl can include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), or silicon (Si) as a heteroatom in addition to a carbon atom. A heterocyclic alkyl can be defined by the number of nuclear atoms rather than the number of carbon atoms. Here, the number of nuclear atoms can refer to the number of atoms including one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si), as well as a carbon (C) atom. For example, the number of nuclear atoms in a heterocyclic alkyl can be 5 to 60, 5 to 30, or 5 to 20.

[0044] As used herein, the term "haloalkyl" can refer to a monovalent functional group derived from an alkyl group in which at least one hydrogen atom is replaced by a halogen atom. The halogen atom can be at least one selected from F, Cl, Br, and I.

[0045] As used herein, the terms “alkylsilyl” and “arylsilyl” refer to the monovalent functional group of a compound in which at least one hydrogen atom of a silane is replaced by the aforementioned alkyl or aryl group.

[0046] As used herein, the terms “alkylamino” and “arylamino” refer to monovalent functional groups derived from compounds in which at least one hydrogen atom of an amine is replaced by the aforementioned alkyl or aryl groups.

[0047] As used herein, the term "arylphosphine" refers to a monovalent functional group derived from compounds in which the phosphine is replaced by the aforementioned aryl group.

[0048] As used herein, the terms “alkylphosphine oxide” and “arylphosphine oxide” refer to the monovalent functional groups derived from compounds in which the aforementioned alkyl or aryl groups are respectively substituted on phosphine oxide.

[0049] As used herein, the term "substitution" means substitution by at least one substituent selected from the group consisting of deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, 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 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 arylphosphin 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 carbonyl group, a cyano group, and a halogen group. When substituted by multiple substituents, the substituents may be the same as or different from each other.

[0050] <Organic luminescent compounds>

[0051] This disclosure provides a novel organic light-emitting compound. The organic light-emitting compound is represented by the following formula 1.

[0052] [Formula 1]

[0053]

[0054] In Equation 1,

[0055] A is a heteroarylene containing 2 to 60 carbon atoms and having at least two nitrogen atoms, or a heteroarylene containing 5 to 60 nuclear atoms and having at least two nitrogen atoms, wherein each of the above groups is unsubstituted or substituted.

[0056] R is hydrogen, an alkyl group containing 1 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a haloalkyl group containing 1 to 40 carbon atoms, a heterocycloalkyl group containing 2 to 40 carbon atoms, a heterocycloalkyl group containing 3 to 40 nuclear atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, a heteroaryl group containing 5 to 60 nuclear atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylamine group containing 1 to 40 carbon atoms, an arylamine group containing 6 to 60 carbon atoms, an arylphosphin group containing 6 to 60 carbon atoms, an alkylphosphine oxide group containing 1 to 40 carbon atoms, an arylphosphine oxide group containing 6 to 60 carbon atoms, a carbonyl group, a cyano group, or a halogen group, each of which is unsubstituted or substituted.

[0057] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the following groups is independently a single bond, an alkylene group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, or a heteroaryl group containing 5 to 60 nuclear atoms, wherein each of the above groups is unsubstituted or substituted.

[0058] Ar1 to Ar3 are each independently an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, or a heteroaryl group containing 5 to 60 nuclear atoms, wherein each of the above groups is unsubstituted or substituted, and

[0059] n is an integer from 0 to 5, where when n is from 2 to 5, each of the multiple L5 and R is independently the same or different from each other.

[0060] Specifically, it can be used as A, R, L a To L dAt least one of the hydrogen, alkyl, cycloalkyl, haloalkyl, heterocycloalkyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylamino, arylamino, arylphosphinyl, alkylphosphine oxide, or arylphosphine oxide groups present with Ar1 to Ar3 is independently unsubstituted or substituted with at least one substituent selected from the group consisting of: deuterium, alkyl containing 1 to 20 carbon atoms, cycloalkyl containing 3 to 20 carbon atoms, haloalkyl containing 1 to 20 carbon atoms, heterocycloalkyl containing 2 to 20 carbon atoms, or containing 3 to 20 nuclear atoms. Heterocyclic alkyl groups, aryl groups containing 6 to 30 carbon atoms, heteroaryl groups containing 2 to 30 carbon atoms, heteroaryl groups containing 5 to 30 nuclear atoms, alkylsilyl groups containing 1 to 20 carbon atoms, alkylsulfonyl groups containing 1 to 20 carbon atoms, arylsilyl groups containing 6 to 30 carbon atoms, alkylamine groups having 1 to 20 carbon atoms, arylamine groups having 6 to 30 carbon atoms, arylphosphin groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, carbonyl groups, cyano groups, or halogen groups. When substituted by multiple substituents, the substituents may be the same as or different from each other.

[0061] In one implementation scheme, in Equation 1,

[0062] A is a heteroaryl group containing 2 to 30 carbon atoms and having at least two nitrogen atoms, or a heteroaryl group containing 5 to 30 nuclear atoms and having at least two nitrogen atoms, wherein each of the above groups is unsubstituted or substituted by the following groups: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, heterocycloalkyl group containing 2 to 20 carbon atoms, heterocycloalkyl group containing 3 to 20 nuclear atoms, aryl group containing 6 to 30 carbon atoms, and aryl group containing 2 to 30 carbon atoms. Heteroaryl groups having 1 to 30 carbon atoms, heteroaryl groups having 5 to 30 nuclear atoms, alkylsilyl groups having 1 to 20 carbon atoms, alkylsulfonyl groups having 1 to 20 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, alkylamino groups having 1 to 20 carbon atoms, arylamino groups having 6 to 30 carbon atoms, arylphosphin groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, carbonyl, cyano, or halogen groups.

[0063] R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, a heterocycloalkyl group containing 3 to 20 nuclear atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, an alkylsilyl group containing 1 to 20 carbon atoms, an arylsilyl group containing 6 to 30 carbon atoms, an alkylamino group containing 1 to 20 carbon atoms, an arylamino group containing 6 to 30 carbon atoms, an arylphosphinyl group containing 6 to 30 carbon atoms, an alkylphosphine oxide group containing 1 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a carbonyl group, a cyano group, or a halogen group, each of which is unsubstituted or modified by the following groups. Group substitution: deuterium, alkyl groups containing 1 to 20 carbon atoms, cycloalkyl groups containing 3 to 20 carbon atoms, haloalkyl groups containing 1 to 20 carbon atoms, heterocycloalkyl groups containing 2 to 20 carbon atoms, heterocycloalkyl groups containing 3 to 20 nuclear atoms, aryl groups containing 6 to 30 carbon atoms, heteroaryl groups containing 2 to 30 carbon atoms, heteroaryl groups containing 5 to 30 nuclear atoms, alkylsilyl groups containing 1 to 20 carbon atoms, alkylsulfonyl groups containing 1 to 20 carbon atoms, arylsilyl groups containing 6 to 30 carbon atoms, alkylamino groups having 1 to 20 carbon atoms, arylamino groups having 6 to 30 carbon atoms, arylphosphin groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, carbonyl, cyano, or halogen groups.

[0064] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L dEach of the following groups is independently a single bond: an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, wherein each of the above groups is unsubstituted or substituted by: deuterium, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, a heterocycloalkyl group containing 3 to 20 nuclear atoms, an aryl group containing 6 to 30 carbon atoms, or a group containing 2... Heteroaryl groups having 1 to 30 carbon atoms, heteroaryl groups having 5 to 30 nuclear atoms, alkylsilyl groups having 1 to 20 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, alkylsulfonyl groups having 1 to 20 carbon atoms, alkylamino groups having 1 to 20 carbon atoms, arylamino groups having 6 to 30 carbon atoms, arylphosphin groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, carbonyl, cyano, or halogen groups.

[0065] Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, wherein each of the above groups is unsubstituted or substituted with the following groups: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, heterocycloalkyl group containing 2 to 20 carbon atoms, heterocycloalkyl group containing 3 to 20 nuclear atoms, aryl group containing 6 to 30 carbon atoms, and aryl group containing 2 to 30 nuclear atoms. Heteroaryl groups having 1 to 30 carbon atoms, heteroaryl groups having 5 to 30 nuclear atoms, alkylsilyl groups having 1 to 20 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, alkylsulfonyl groups having 1 to 20 carbon atoms, alkylamino groups having 1 to 20 carbon atoms, arylamino groups having 6 to 30 carbon atoms, arylphosphin groups having 6 to 30 carbon atoms, alkylphosphine oxide groups having 1 to 20 carbon atoms, arylphosphine oxide groups having 6 to 30 carbon atoms, carbonyl, cyano, or halogen groups, and

[0066] n is an integer from 0 to 5, where when n is from 2 to 5, each of the multiple L5 and R is independently the same or different from each other.

[0067] In the implementation scheme, when n is 0, it can refer to the unsubstituted hydrogen present in A by *-L5-R.

[0068] In the implementation plan, in Equation 1,

[0069] A is a heteroaryl group containing 2 to 30 carbon atoms and having at least two nitrogen atoms, or a heteroaryl group containing 5 to 30 nuclear atoms and having at least two nitrogen atoms.

[0070] R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, a cyano group, or a halogen group, each of which is unsubstituted or substituted with deuterium, an alkyl group containing 1 to 20 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, a cyano group, or a halogen group.

[0071] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the above groups is independently a single bond, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, wherein each of the above groups is unsubstituted or substituted with deuterium, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, or a carbonyl group.

[0072] Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, each of which is unsubstituted or substituted by the following groups: deuterium, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, an alkylsilyl group containing 1 to 20 carbon atoms, an arylsilyl group containing 6 to 30 carbon atoms, an alkylsulfonyl group containing 1 to 20 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, a carbonyl group, a cyano group, or a halogen group.

[0073] n is an integer from 1 to 3, where when n is 2 or 3, each of the multiple L5 and R is independently the same or different from each other.

[0074] In one implementation, A can be represented by any of the following formulas A-1 to A-15.

[0075] [Formula A-1]

[0076]

[0077] [Formula A-2]

[0078]

[0079] [Formula A-3]

[0080]

[0081] [Formula A-4]

[0082]

[0083] [Formula A-5]

[0084]

[0085] [Formula A-6]

[0086]

[0087] [Formula A-7]

[0088]

[0089] [Formula A-8]

[0090]

[0091] [Formula A-9]

[0092]

[0093] [Formula A-10]

[0094]

[0095] [Formula A-11]

[0096]

[0097] [Formula A-12]

[0098]

[0099] [Formula A-13]

[0100]

[0101] [Formula A-14]

[0102]

[0103] [Formula A-15]

[0104]

[0105] In each of Equations A-1 to A-15, * denotes the site that is bonded to L4 in Equation 1.

[0106] In one implementation scheme, in Equation 1,

[0107] A is a heteroaryl group containing 2 to 30 carbon atoms and having at least two nitrogen atoms, or a heteroaryl group containing 5 to 30 nuclear atoms and having at least two nitrogen atoms.

[0108] R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, a cyano group, or a halogen group, each of which is unsubstituted or substituted with deuterium, an alkyl group containing 1 to 20 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, a cyano group, or a halogen group.

[0109] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the following groups is independently a single bond, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, wherein each of the above groups is unsubstituted or substituted with deuterium, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, or a carbonyl group.

[0110] Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms, each of which is unsubstituted or substituted by the following groups: deuterium, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nuclear atoms, an alkylsilyl group containing 1 to 20 carbon atoms, an arylsilyl group containing 6 to 30 carbon atoms, an alkylsulfonyl group containing 1 to 20 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, a carbonyl group, a cyano group, or a halogen group.

[0111] n is an integer from 0 to 3, where when n is 2 or 3, each of the multiple L5 and R is independently the same or different from each other.

[0112] In one implementation scheme, in Equation 1,

[0113] A is any one of formulas A-1 to A-15.

[0114] R is hydrogen, methyl, phenyl, biphenyl, naphthyl, benzophenanthryl, pyridyl, phenanthryl, phenanthrolyl, fluorenyl, dibenzothiophene, carbazole, phenoxathio, cyano, or fluorine, and each of the above groups is unsubstituted or substituted with deuterium, methyl, phenyl, pyridyl, or cyano.

[0115] L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of these groups can be independently a single bond, phenylene, biphenylene, terphenylene, naphthylene, pyridylene, pyridazinylene, dibenzofuranylene, or benzoquinolineylene, and each of these groups can be unsubstituted or substituted with deuterium, naphthyl, dibenzofuranyl, or carbonyl.

[0116] Ar1 to Ar3 are each independently phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, carbazole, fluorenyl, thiadiazolyl, oxadiazolyl, spirodifluorenyl, benzonaphthofuranyl, benzothiophene-pyrimidinyl, benzofuran-pyridinyl, dibenzofuranyl, naphthidyl, pyrimidinyl, phenanthrene, phenanthrene-pyrinyl, oxanthraceneyl, anthraceneyl, benzoxanthyl, triphenylsilyl, heptaazaphenarenyl, or acenaphthopyridinyl, each of the above groups being unsubstituted or substituted by the following groups: deuterium, methyl, butyl, phenyl, biphenyl, fluorenyl, pyridinyl, cyclohexyl, cyclopentyl, trimethylsilyl, carbonyl, methanesulfonyl, dimethylphosphine oxide, trifluoromethyl, cyano, or chlorine.

[0117] n is an integer from 0 to 3, where when n is 2 or 3, each of the multiple L5 and R is independently the same or different from each other.

[0118] [Formula A-1]

[0119]

[0120] [Formula A-2]

[0121]

[0122] [Formula A-3]

[0123]

[0124] [Formula A-4]

[0125]

[0126] [Formula A-5]

[0127]

[0128] [Formula A-6]

[0129]

[0130] [Formula A-7]

[0131]

[0132] [Formula A-8]

[0133]

[0134] [Formula A-9]

[0135]

[0136] [Formula A-10]

[0137]

[0138] [Formula A-11]

[0139]

[0140] [Formula A-12]

[0141]

[0142] [Formula A-13]

[0143]

[0144] [Formula A-14]

[0145]

[0146] [Formula A-15]

[0147]

[0148] In each of Equations A-1 to A-15, * denotes the site that is bonded to L4 in Equation 1.

[0149] In one embodiment, the organic light-emitting compound represented by Formula 1 may be selected from any one of the following compounds 001 to 162:

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190] .

[0191] As a specific example, the compound represented by Formula 1 can be any one of compounds 1 to 20.

[0192] The novel organic light-emitting compound disclosed herein has a double EWG-type structure, wherein an aromatic group is bonded to the 2-, 4-, 5-, and 6-carbon positions of a pyrimidine as an electron-withdrawing group (EWG), and an additional EWG capable of increasing electron density is further bonded to an aromatic group bonded to the 4-carbon position. Such a structure induces horizontal orientation to increase rigidity and improve efficiency, thereby providing an organic layer material with improved performance.

[0193] Furthermore, by using the organic light-emitting compound according to this disclosure as a material for the electron transport layer, excellent performance can be obtained in terms of driving voltage, EL peak and current efficiency.

[0194] Organic electroluminescent devices

[0195] This disclosure provides an organic electroluminescent device comprising the novel organic light-emitting compound described above. The organic light-emitting compound according to this disclosure can be incorporated into at least one organic material layer disposed between the cathode and anode of the organic electroluminescent device.

[0196] In one embodiment, the organic electroluminescent device includes 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 contains an organic light-emitting compound according to the present disclosure.

[0197] anode

[0198] The organic electroluminescent device disclosed herein includes an anode. The anode is used to inject holes into an organic layer. Here, the organic layer may refer to at least one layer formed between the anode and the cathode.

[0199] There are no particular limitations on the type of anode material, and the anode can be prepared according to conventional methods known in the art. Anode materials may include, for example: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); metal and oxide complexes, such as ZnO:Al and SnO2:Sb; conductive polymers, such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; or carbon black. Each of these compounds may be used alone or in combination of two or more thereof.

[0200] There are no particular limitations on the methods used to prepare the anode, and it can be prepared according to conventional methods known in the art. For example, the anode can be formed by coating a substrate (such as a silicon wafer, quartz, glass plate, metal plate or plastic film) with an anode material.

[0201] cathode

[0202] The organic electroluminescent device disclosed herein includes a cathode. The cathode is used to inject electrons into the organic layer.

[0203] There are no particular limitations on the type of cathode material constituting the cathode, and it can be prepared according to conventional methods known in the art. Cathode materials include, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead, or alloys thereof; or multilayer materials such as LiF / Al or LiO2 / Al.

[0204] Emissive layer

[0205] The organic electroluminescent device disclosed herein includes a light-emitting layer disposed between a cathode and an anode. The light-emitting layer is a layer in which holes and electrons combine to form excitons, and the color of the light emitted by the organic electroluminescent device can vary depending on the material constituting the light-emitting layer.

[0206] Depending on the desired wavelength of light emission, the luminescent material constituting the luminescent layer can be selected from a variety of commercially available materials without particular limitation.

[0207] In one implementation, the luminescent material can be classified into blue, green, and red luminescent materials, etc., based on the color of the emitted light. The luminescent layer can be formed using a combination of a host material and a dopant as the luminescent material to prevent problems such as color purity degradation or device efficiency reduction due to luminescence decay. The luminous efficiency of organic electroluminescent devices can be improved by using a host material as the main material constituting the luminescent layer and a small amount of dopant, which has a smaller band gap than the host material.

[0208] Electronic transmission area

[0209] The organic electroluminescent device disclosed herein includes an electron transport region disposed between the light-emitting layer and the cathode.

[0210] An electron transport region is used to move electrons injected from the cathode to the light-emitting layer. Such an electron transport region may include at least one selected from the group consisting of an electron injection layer or an electron transport layer. In this case, considering the characteristics of organic electroluminescent devices, the organic electroluminescent device preferably includes both the electron transport layer and the electron injection layer described above.

[0211] In the electron transport region, the electron injection layer can be formed of any electron injection material that facilitates the injection of electrons from the cathode and has high electron mobility. Non-limiting examples of useful electron injection materials include the aforementioned amphiphilic compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As specific examples, electron injection materials include at least one selected from the group consisting of: LiF, Li₂O, BaO, NaCl, CsF; lanthanides such as Yb; and metal halides such as RbCl and RbI.

[0212] The electron transport layer may comprise the organic light-emitting compound according to the present disclosure described above. The organic light-emitting compound according to the present disclosure has a double EWG-type structure, wherein an aromatic group is bonded to the 2-, 4-, 5-, and 6-carbon positions of a pyrimidine as an electron-withdrawing group (EWG), and an additional EWG capable of increasing electron density is further bonded to an aromatic group bonded to the 4-carbon position. This structure induces horizontal orientation to increase rigidity and improve efficiency, thereby providing an organic layer material with improved performance. Furthermore, by using the novel organic light-emitting compound according to the present disclosure as an electron transport layer material, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0213] The electron transport layer can be formed by mixing an organic light-emitting compound according to the present disclosure with lithium hydroxyquinoline (Liq). Liq has a conduction band of 5.58 eV and a valence band of 3.153 eV, which helps to lower the potential barrier.

[0214] The electron transport region can be prepared using conventional methods known in the art. Methods for forming the electron transport region may include, for example, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser-induced thermal imaging (LITI), but are not limited thereto.

[0215] Electron transport auxiliary layer

[0216] The organic electroluminescent device disclosed herein 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.

[0217] The electron transport auxiliary layer may comprise the organic light-emitting compound according to the present disclosure as described above. The organic light-emitting compound according to the present disclosure has a double EWG-type structure, wherein an aromatic group is bonded to the 2-, 4-, 5-, and 6-carbon positions of a pyrimidine as an electron-withdrawing group (EWG), and an additional EWG capable of increasing electron density is further bonded to an aromatic group bonded to the 4-carbon position. This structure induces horizontal orientation to increase rigidity and improve efficiency, thereby providing an organic layer material with improved performance.

[0218] Furthermore, by using the novel organic light-emitting compound according to this disclosure as a material for the electron transport auxiliary layer, excellent performance can be achieved in terms of driving voltage, EL peak and current efficiency.

[0219] The electron transport auxiliary layer can be formed according to conventional methods known in the art, such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser-induced thermal imaging (LITI), but is not limited thereto.

[0220] Hole transport region

[0221] The organic electroluminescent device disclosed herein includes a hole transport region disposed between an anode and an emissive layer. The hole transport region is used to move holes injected from the anode to the emissive layer.

[0222] The hole transport region may include at least one selected from the group consisting of a hole injection layer or a hole transport layer. In this case, considering the characteristics of organic electroluminescent devices, the organic electroluminescent device preferably includes both the hole transport layer and the hole injection layer described above.

[0223] Any material can be used for both the hole injection layer and the hole transport layer without particular limitation, as long as it has a low hole injection barrier and a high hole mobility, and can be selected from hole injection and hole transport materials used in the art without limitation. The materials constituting the hole injection layer and the materials constituting the hole transport layer can be the same as or different from each other.

[0224] Hole injection materials can be selected from those known in the art without limitation. Non-limiting examples of useful hole injection materials include: phthalocyanine compounds, such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), TDATA (4,4'4"-tris(N,N-diphenylamino)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 / camphorsulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrenesulfonate)), etc. Each of these compounds can be used alone or in combination of two or more thereof.

[0225] Furthermore, hole transport materials can be selected from those known in the art without limitation. Non-limiting examples of useful hole transport materials include: carbazole derivatives, such as phenylcarbazole and polyvinylcarbazole; fluorene-based derivatives; triphenylamine derivatives, such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine); NPB (N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]), etc. Each of these compounds can be used alone or in combination of two or more of them.

[0226] Hole transport layers can be formed using conventional methods known in the art, such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser-induced thermal imaging (LITI), but are not limited thereto.

[0227] Light-emitting auxiliary layer

[0228] The organic electroluminescent device according to this disclosure may further include a light-emitting auxiliary layer disposed between the hole transport region and the light-emitting layer. The light-emitting auxiliary layer is used to control the thickness of the organic layer while transporting holes from the hole transport region to the light-emitting layer. The light-emitting auxiliary layer prevents electrons from moving to the hole transport layer based on its high LUMO and prevents excitons from moving from the light-emitting layer to the hole transport layer based on its high triplet (T1) energy level.

[0229] The light-emitting auxiliary layer may include a hole transport material and may be formed of the same material as that in the hole transport region. Furthermore, the light-emitting auxiliary layers of red, green, and blue organic electroluminescent devices may be formed of the same material as each other.

[0230] There are no particular limitations on the materials used for the luminescent auxiliary layer, and they can be, for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives. Furthermore, in addition to the materials mentioned above, the luminescent auxiliary layer may optionally contain a p-type dopant. The p-type dopant can be any p-type dopant used in the art.

[0231] Cover layer

[0232] The organic electroluminescent device disclosed herein may further include a capping layer disposed on the cathode. The capping layer serves to protect the electroluminescent device and promote the efficient emission of light generated in the organic layer to the outside.

[0233] The covering material constituting the covering layer may include, for example, at least one selected from the group consisting of aluminum tri-8-hydroxyquinoline (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylthiophene, 4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), and 1,1'-bis(di-4-tolylaminophenyl)cyclohexane (TAPC), but is not limited thereto.

[0234] The capping layer can be a single layer or can include two or more layers with different refractive indices to gradually change the refractive index of light passing through the two or more layers.

[0235] The capping layer can be formed according to conventional methods known in the art, and the method can be selected from a variety of methods, such as vacuum deposition, spin coating, casting and LB (Langmuir-Blodgett).

[0236] This disclosure provides the use of the organic light-emitting compounds described above in organic electroluminescent devices. The organic light-emitting compounds impart significantly improved luminescent performance, driving voltage, lifetime, and efficiency to organic electroluminescent devices.

[0237] In one embodiment, the organic light-emitting compound can be used as an electron transport material in an organic electroluminescent device.

[0238] In one implementation, when the organic light-emitting compound is used as an electron transport material in an organic electroluminescent device, it can be used as a material for the electron transport region.

[0239] In one embodiment, the organic light-emitting compound can be used as a material for an electron transport layer and / or an electron transport auxiliary layer in an organic electroluminescent device.

[0240] In the following description, specific examples will be used to illustrate this disclosure. However, the examples provided are merely for the purpose of illustrating this disclosure in detail and should not be construed as limiting the scope of this disclosure.

[0241] [Preparation Example]

[0242] [Preparation Example 1]: Synthesis of Compound J-1

[0243] (Step 1) Synthesis of compound J-1-1

[0244]

[0245] 1,2-Diphenylethane-1-one (1.96 g, 10 mmol) and 4-bromobenzaldehyde (1.85 g, 10 mmol) were added to 50 mL of toluene and reacted at 120 °C with stirring for 48 h. After the reaction was complete, the mixture was extracted with ethyl acetate, the organic layer was washed with an aqueous solution of NaHCO3, and then distilled under reduced pressure. Compound J-1-1 (1.48 g, 41% yield) was obtained from the resulting reaction mixture by column chromatography.

[0246] (Step 2) Synthesis of compound J-1

[0247]

[0248] The obtained compound J-1-1 (3.63 g, 10 mmol), benzimamide hydrochloride (1.56 g, 10 mmol), and NaOH (1.2 g, 30 mmol) were added to 100 mL of ethanol and reacted under reflux with stirring for 3 days. After the reaction was complete, the mixture was cooled to room temperature and water was added with stirring. The solid was filtered, washed with water and ethanol, and dried. Compound J-1 (1.43 g, 31% yield) was obtained from the resulting reaction mixture by column chromatography.

[0249] [Preparation Example 2]: Synthesis of Compound J-2

[0250]

[0251] 4,6-Dichloro-2,5-diphenylpyrimidine (6.02 g, 20 mmol), phenylboronic acid (1.21 g, 10 mmol), PdCl₂(PPh₃)₂ (0.14 g, 0.2 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL dioxane and 25 mL H₂O, and the mixture was reacted at 70 °C with stirring for 5 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO₄ was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound J-2 (1.43 g, 42% yield) was obtained by column chromatography.

[0252] [Preparation Example 3]: Synthesis of Compound J-3

[0253] (Step 1) Synthesis of compound J-3-1

[0254]

[0255] Perchloropyrimidine (6.53 g, 30 mmol), phenylboronic acid (1.21 g, 10 mmol), PdCl₂(PPh₃)₂ (0.14 g, 0.2 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL dioxane and 25 mL H₂O, and the mixture was reacted at 60 °C with stirring for 2 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO₄ was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound J-3-1 (0.85 g, 33% yield) was obtained by column chromatography.

[0256] (Step 2) Synthesis of compound J-3-2

[0257]

[0258] The obtained compound J-3-1 (7.78 g, 30 mmol), (4-chlorophenyl-2,3,5,6-d4)boric acid (1.60 g, 10 mmol), PdCl2(PPh3)2 (0.14 g, 0.2 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL dioxane and 25 mL H2O, and the mixture was reacted at 70 °C with stirring for 5 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound J-3-2 (1.12 g, 33% yield) was obtained by column chromatography.

[0259] (Step 3) Synthesis of compound J-3

[0260]

[0261] The obtained J-3-2 (6.79 g, 20 mmol), (phenyl-4-d)boric acid (1.22 g, 10 mmol), PdCl2(PPh3)2 (0.14 g, 0.2 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL dioxane and 25 mL H2O, and the mixture was reacted at 80 °C with stirring for 6 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound J-3 (1.64 g, yield 43%) was obtained by column chromatography.

[0262] [Synthesis example]

[0263] [Synthetic Example 1]: Synthesis of Compound 1

[0264]

[0265] Compound J-1 (4.63 g, 10 mmol), synthesized by the method of Preparation Example 1, along with (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (3.53 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol), were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O. The mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 1 (2.83 g, 41% yield) was obtained by column chromatography.

[0266] Mass spectrometry: [(M+H)] + ]:691

[0267] [Synthetic Example 2]: Synthesis of Compound 2

[0268]

[0269] Compound J-2 (3.42 g, 10 mmol), synthesized by the method of Preparation Example 2, along with (4-(4,6-bis([1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)phenyl)boronic acid (5.05 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol), were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O. The mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 2 (3.22 g, 42% yield) was obtained by column chromatography.

[0270] Mass spectrometry: [(M+H)] + ]:767

[0271] [Synthetic Example 3]: Synthesis of Compound 3

[0272]

[0273] 4-(5-bromopyridin-2-yl)-2,5,6-triphenylpyrimidine (4.64 g, 10 mmol), (3-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine-4-yl)phenyl)boronic acid (4.28 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 3 (3.30 g, 43% yield) was obtained by column chromatography.

[0274] Mass spectrometry: [(M+H)] + ]:767

[0275] [Synthetic Example 4]: Synthesis of Compound 4

[0276]

[0277] 4-(4-bromophenyl)-2,5-diphenyl-6-(pyridin-2-yl)pyrimidine (4.64 g, 10 mmol), (2-(4,6-diphenylpyrimidin-2-yl)phenyl)boronic acid (3.52 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 4 (3.04 g, 44% yield) was obtained by column chromatography.

[0278] Mass spectrometry: [(M+H)] + ]:691

[0279] [Synthetic Example 5]: Synthesis of Compound 5

[0280]

[0281] 4-(4-bromophenyl)-2,6-diphenyl-5-(pyridin-3-yl)pyrimidine (4.64 g, 10 mmol), (3-(2-phenyl-6-(pyridin-2-yl)pyrimidin-4-yl)phenyl)boronic acid (3.53 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 5 (3.11 g, 45% yield) was obtained by column chromatography.

[0282] Mass spectrometry: [(M+H)] + ]:692

[0283] [Synthetic Example 6]: Synthesis of Compound 6

[0284]

[0285] 4-(4-bromophenyl)-5,6-diphenyl-2-(pyridin-4-yl)pyrimidine (4.64 g, 10 mmol), (6-(2-phenyl-6-(4-(pyridin-2-yl)phenyl)pyrimidine-4-yl)pyridin-2-yl)boronic acid (4.30 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 6 (3.54 g, 46% yield) was obtained by column chromatography.

[0286] Mass spectrometry: [(M+H)] + ]:769

[0287] [Synthetic Example 7]: Synthesis of Compound 7

[0288] (Step 1) Synthesis of Compound 7-1

[0289]

[0290] Compound J-3 (3.82 g, 10 mmol), synthesized by the method of Preparation Example 3, (9-phenyl-9H-carbazole-3-yl)boronic acid (2.87 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 7-1 (2.76 g, 47% yield) was obtained by column chromatography.

[0291] Mass spectrometry: [(M+H)] + ]:589

[0292] (Step 2) Synthesis of Compound 7

[0293]

[0294] Compound 7-1 (5.89 g, 10 mmol), (3-(9-phenyl-1,10-phenanthroline-2-yl)phenyl)boronic acid (3.76 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs2CO3 (6.51 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 7 (4.15 g, 47% yield) was obtained by column chromatography.

[0295] Mass spectrometry: [(M+H)] + ]:885

[0296] [Synthetic Example 8]: Synthesis of Compound 8

[0297] (Step 1) 4-(4'-(2-(4-chlorophenyl)-5,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-2- Synthesis of phenylbenzofurano[3,2-d]pyrimidine

[0298]

[0299] 4-(4-bromophenyl)-2-(4-chlorophenyl)-5,6-diphenylpyrimidine (4.97 g, 10 mmol), (3-(2-phenylbenzofurano[3,2-d]pyrimidin-4-yl)phenyl)boronic acid (3.66 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4-(4'-(2-(4-chlorophenyl)-5,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-2-phenylbenzofurano[3,2-d]pyrimidine (3.54 g, 48% yield) was obtained by column chromatography.

[0300] Mass spectrometry: [(M+H)] + ]:739

[0301] (Step 2) Synthesis of Compound 8

[0302]

[0303] The obtained 4-(4'-(2-(4-chlorophenyl)-5,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-2-phenylbenzofuran[3,2-d]pyrimidine (7.39 g, 10 mmol), naphtho[2,1-b]benzofuran-10-ylboronic acid (2.62 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs2CO3 (6.51 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 8 (4.42 g, yield 48%) was obtained by column chromatography.

[0304] Mass spectrometry: [(M+H)] + ]:921

[0305] [Synthetic Example 9]: Synthesis of Compound 9

[0306] (Step 1) Synthesis of 4-(4-chlorophenyl)-2,5-diphenyl-6-(4-(2-phenylpyrimidin-5-yl)phenyl)pyrimidine

[0307]

[0308] 4-(4-bromophenyl)-6-(4-chlorophenyl)-2,5-diphenylpyrimidine (4.97 g, 10 mmol), (2-phenylpyrimidin-5-yl)boronic acid (2.00 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4-(4-chlorophenyl)-2,5-diphenyl-6-(4-(2-phenylpyrimidin-5-yl)phenyl)pyrimidine (2.80 g, yield 49%) was obtained by column chromatography.

[0309] Mass spectrometry: [(M+H)] + ]:573

[0310] (Step 2) Synthesis of Compound 9

[0311]

[0312] The obtained 4-(4-chlorophenyl)-2,5-diphenyl-6-(4-(2-phenylpyrimidin-5-yl)phenyl)pyrimidine (5.73 g, 10 mmol), (4-(tert-butyl)phenyl)boronic acid (1.78 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs2CO3 (6.51 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 ml of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 9 (3.28 g, 49% yield) was obtained by column chromatography.

[0313] Mass spectrometry: [(M+H)] + ]:670

[0314] [Synthetic Example 10]: Synthesis of Compound 10

[0315]

[0316] 4,6-Dichloro-2,5-diphenylpyrimidine (3.01 g, 10 mmol), (4-(2-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)boronic acid (3.82 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 10 (4.52 g, 50% yield) was obtained by column chromatography.

[0317] Mass spectrometry: [(M+H)] + ]:905

[0318] [Synthetic Example 11]: Synthesis of Compound 11

[0319] (Step 1) Synthesis of 4-(6-(4-chlorophenyl)-2,5-diphenylpyrimidin-4-yl)-1,8-naphthidine

[0320]

[0321] 4-Chloro-6-(4-chlorophenyl)-2,5-diphenylpyrimidine (3.77 g, 10 mmol), (1,8-naphthid-4-yl)boronic acid (1.73 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4-(6-(4-chlorophenyl)-2,5-diphenylpyrimthid-4-yl)-1,8-naphthidine (3.86 g, 41% yield) was obtained by column chromatography.

[0322] Mass spectrometry: [(M+H)] + ]:470

[0323] (Step 2) Synthesis of Compound 11

[0324]

[0325] 4-(6-(4-chlorophenyl)-2,5-diphenylpyrimidin-4-yl)-1,8-naphthidine (4.70 g, 10 mmol), (4-(4-phenylquinazoline-2-yl)phenyl)boronic acid (3.26 g, 10 mmol), Pd(OAc)₂ (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and Cs₂CO₃ (6.51 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H₂O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO₄ was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 11 (2.93 g, 41% yield) was obtained by column chromatography.

[0326] Mass spectrometry: [(M+H)] + ]:716

[0327] [Synthetic Example 12]: Synthesis of Compound 12

[0328]

[0329] 4-Chloro-5-phenyl-2,6-bis(pyridin-4-yl)pyrimidine (3.44 g, 10 mmol), (2-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)boronic acid (4.29 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 12 (2.91 g, 42% yield) was obtained by column chromatography.

[0330] Mass spectrometry: [(M+H)] + ]:693

[0331] [Synthetic Example 13]: Synthesis of Compound 13

[0332]

[0333] 4-(1-bromodibenzo[b,d]furan-4-yl)-2,5,6-triphenylpyrimidine (5.53 g, 10 mmol), (4-(dibenzo[f,h]quinazolin-2-yl)phenyl)boronic acid (3.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 13 (3.34 g, 43% yield) was obtained by column chromatography.

[0334] Mass spectrometry: [(M+H)] + ]:778

[0335] [Synthetic Example 14]: Synthesis of Compound 14

[0336]

[0337] 2-([1,1':3',1''-terphenyl]-5'-yl)-4,6-dichloro-5-phenylpyrimidine (4.53 g, 10 mmol), (5,5-dimethyl-5H-cyclopentadieno[2,1-c:3,4-c']dipyridin-3-yl)boronic acid (4.80 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 ml of 1,4-dioxane and 25 ml of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 14 (3.40 g, 44% yield) was obtained by column chromatography.

[0338] Mass spectrometry: [(M+H)] + ]:772

[0339] [Synthetic Example 15]: Synthesis of Compound 15

[0340] (Step 1) 2,5-Di([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(4,5,6-triphenylpyrimidin-2-yl)benzene Synthesis of pyrimidine

[0341]

[0342] 2,5-bis([1,1'-biphenyl]-4-yl)-4,6-dichloropyrimidine (4.53 g, 10 mmol), (3-(4,5,6-triphenylpyrimidin-2-yl)phenyl)boronic acid (4.28 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 2,5-bis([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(4,5,6-triphenylpyrimidin-2-yl)phenyl)pyrimidine (3.60 g, 45% yield) was obtained by column chromatography.

[0343] Mass spectrometry: [(M+H)] + ]:801

[0344] (Step 2) Synthesis of Compound 15

[0345]

[0346] The obtained 2,5-bis([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(4,5,6-triphenylpyrimidin-2-yl)phenyl)pyrimidine (8.01 g, 10 mmol), (2-(3-(phenyl-d5)quinoxalin-2-yl)phenyl)boronic acid (3.31 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 15 (4.73 g, 45% yield) was obtained by column chromatography.

[0347] Mass spectrometry: [(M+H)] + ]:1052

[0348] [Synthetic Example 16]: Synthesis of Compound 16

[0349] (Step 1) Synthesis of 4-(2-(4,6-dichloro-5-phenylpyrimidin-2-yl)phenyl)benzofurano[3,2-b]pyridine become

[0350]

[0351] 2-(2-bromophenyl)-4,6-dichloro-5-phenylpyrimidine (3.80 g, 10 mmol), benzofurano[3,2-b]pyridin-4-ylboronic acid (2.13 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4-(2-(4,6-dichloro-5-phenylpyrimidine-2-yl)phenyl)benzofurano[3,2-b]pyrimidine (2.15 g, 46% yield) was obtained by column chromatography.

[0352] Mass spectrometry: [(M+H)] + ]:468

[0353] (Step 2) Synthesis of Compound 16

[0354]

[0355] The obtained 4-(2-(4,6-dichloro-5-phenylpyrimidin-2-yl)phenyl)benzofuran[3,2-b]pyridine (4.68 g, 10 mmol), (2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (8.58 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 16 (5.36 g, 46% yield) was obtained by column chromatography.

[0356] Mass spectrometry: [(M+H)] + ]:1166

[0357] [Synthetic Example 17]: Synthesis of Compound 17

[0358] (Step 1) Synthesis of 4-(3-(4,6-dichloro-2-phenylpyrimidin-5-yl)phenyl)pyridine-2,6-dicarboxynitrile

[0359]

[0360] 5-(3-bromophenyl)-4,6-dichloro-2-phenylpyrimidine (3.80 g, 10 mmol), (2,6-dicyanopyridin-4-yl)boronic acid (1.72 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4-(3-(4,6-dichloro-2-phenylpyrimidine-5-yl)phenyl)pyridin-2,6-dicarboxynitrile (2.01 g, 47% yield) was obtained by column chromatography.

[0361] Mass spectrometry: [(M+H)] + ]:428

[0362] (Step 2) Synthesis of Compound 17

[0363]

[0364] The obtained 4-(3-(4,6-dichloro-2-phenylpyrimidin-5-yl)phenyl)pyridine-2,6-dicarboxynitrile (4.28 g, 10 mmol), (5-phenylpyrimidin-2-yl)boronic acid (4.00 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 17 (3.13 g, 47% yield) was obtained by column chromatography.

[0365] Mass spectrometry: [(M+H)] + ]:667

[0366] [Synthetic Example 18]: Synthesis of Compound 18

[0367] (Step 1) Synthesis of 4,6-dichloro-2-(4-(2,6-dimethylpyridin-3-yl)phenyl)-5-phenylpyrimidine

[0368]

[0369] 2-(4-bromophenyl)-4,6-dichloro-5-phenylpyrimidine (3.80 g, 10 mmol), (2,6-dimethylpyridin-3-yl)boronic acid (1.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 4,6-dichloro-2-(4-(2,6-dimethylpyridin-3-yl)phenyl)-5-phenylpyrimidine (1.95 g, 48% yield) was obtained by column chromatography.

[0370] Mass spectrometry: [(M+H)] + ]:406

[0371] (Step 2) Synthesis of Compound 18

[0372]

[0373] The obtained 4,6-dichloro-2-(4-(2,6-dimethylpyridin-3-yl)phenyl)-5-phenylpyrimidine (4.60 g, 10 mmol), (3-(5,6-diphenylpyrazin-2-yl)phenyl)boronic acid (7.04 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 18 (4.56 g, 48% yield) was obtained by column chromatography.

[0374] Mass spectrometry: [(M+H)] + ]:950

[0375] [Synthetic Example 19]: Synthesis of Compound 19

[0376] (Step 1) Synthesis of 6-(4-chloro-2,6-diphenylpyrimidin-5-yl)phenanthridine

[0377]

[0378] 5-Bromo-4-chloro-2,6-diphenylpyrimidine (3.45 g, 10 mmol), phenanthridine-6-ylboronic acid (2.23 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 6-(4-chloro-2,6-diphenylpyrimidine-5-yl)phenanthridine (2.17 g, yield 49%) was obtained by column chromatography.

[0379] Mass spectrometry: [(M+H)] + ]:443

[0380] (Step 2) Synthesis of Compound 19

[0381]

[0382] The obtained 6-(4-chloro-2,6-diphenylpyrimidin-5-yl)phenanthridine (8.87 g, 10 mmol), (pyridazine-3,6-diylbis(2,1-phenylene))diboronic acid (3.19 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 19 (5.13 g, 49% yield) was obtained by column chromatography.

[0383] Mass spectrometry: [(M+H)] + ]:1047

[0384] [Synthetic Example 20]: Synthesis of Compound 20

[0385] (Step 1) Synthesis of 2-(4-chloro-6-phenyl-2-(p-tolyl)pyrimidin-5-yl)-9-phenyl-1,10-phenanthroline

[0386]

[0387] 5-Bromo-4-chloro-6-phenyl-2-(p-Tolyl)pyrimidine (3.59 g, 10 mmol), (9-phenyl-1,10-phenanthroline-2-yl)boronic acid (3.00 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL of 1,4-dioxane and 25 mL of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and the compound 2-(4-chloro-6-phenyl-2-(p-Tolyl)pyrimidine-5-yl)-9-phenyl-1,10-phenanthroline (2.67 g, 50% yield) was obtained by column chromatography.

[0388] Mass spectrometry: [(M+H)] + ]:535

[0389] (Step 2) Synthesis of Compound 20

[0390]

[0391] The obtained 2-(4-chloro-6-phenyl-2-(p-tolyl)pyrimidin-5-yl)-9-phenyl-1,10-phenanthroline (5.35 g, 10 mmol), (5-cyanopyrimidin-2-yl)boronic acid (1.48 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 1,4-dioxane and 25 ml of H2O, and the mixture was reacted at 100 °C with stirring for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The solvent was removed from the filtered organic layer, and compound 20 (3.01 g, 50% yield) was obtained by column chromatography.

[0392] Mass spectrometry: [(M+H)] + ]:603

[0393] [Examples and Comparative Examples]

[0394] [Examples 1 to 20 and Comparative Examples 1 to 3]: Fabrication of Blue Organic Electroluminescent Devices

[0395] The compound synthesized in the synthesis example was purified to high purity by sublimation using a known method, and then a blue organic electroluminescent device was manufactured according to the following method.

[0396] First, a glass substrate coated with 1200 Å of indium tin oxide (ITO) is ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate is ultrasonically cleaned with a solvent (such as isopropanol, acetone, or methanol), then dried and cleaned with UV ozone for 5 minutes using a Power sonic 405 (Hwashin Tech) to create a substrate with ITO transparent electrodes. The manufactured substrate is then transferred to a vacuum evaporation machine.

[0397] Hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport auxiliary layer, electron transport layer, electron injection layer and cathode are sequentially laminated onto the ITO transparent electrode (anode) of the substrate prepared as described above to manufacture an organic electroluminescent device. Specifically, a hole injection layer is formed by co-depositing HI and HAT-CN6 to a thickness of 10 nm on the anode at a weight ratio of 98:2; a hole transport layer is formed by depositing HI to a thickness of 140 nm on the hole injection layer; a light-emitting auxiliary layer is formed by depositing EB to a thickness of 5 nm on the hole transport layer; a light-emitting layer is formed by co-depositing BH and BD to a thickness of 20 nm on the light-emitting auxiliary layer at a weight ratio of 98:2; an electron transport auxiliary layer is formed by depositing a material for an electron transport auxiliary layer to a thickness of 5 nm on the light-emitting layer; an electron transport layer is formed by co-depositing ET and Liq to a thickness of 30 nm on the electron transport auxiliary layer at a weight ratio of 1:1; an electron injection layer is formed by depositing LiF to a thickness of 1 nm on the electron transport layer; and a cathode is formed by depositing Al to a thickness of 100 nm on the electron injection layer. The structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq are shown in Table 1 below, and the materials used for the electron transport auxiliary layer are shown in Table 2 below.

[0398] [Table 1]

[0399]

[0400]

[0401] [Table 2]

[0402]

[0403]

[0404] [Examples 21 to 40 and Comparative Examples 4 to 6]: Fabrication of Blue Organic Electroluminescent Devices

[0405] The compound synthesized in the synthesis example was purified to high purity by sublimation using a known method, and then a blue organic electroluminescent device was manufactured according to the following method.

[0406] First, a glass substrate coated with 1200 Å of indium tin oxide (ITO) is ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate is ultrasonically cleaned with a solvent (such as isopropanol, acetone, or methanol), then dried and cleaned with UV ozone for 5 minutes using a Power sonic 405 (Hwashin Tech) to create a substrate with ITO transparent electrodes. The manufactured substrate is then transferred to a vacuum evaporation machine.

[0407] Hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport auxiliary layer, electron transport layer, electron injection layer and cathode are sequentially laminated onto the ITO transparent electrode (anode) of the substrate prepared as described above to manufacture an organic electroluminescent device. Specifically, a hole injection layer is formed by co-depositing HI and HAT-CN6 to a thickness of 10 nm on the anode at a weight ratio of 98:2; a hole transport layer is formed by depositing HI to a thickness of 140 nm on the hole injection layer; a light-emitting auxiliary layer is formed by depositing EB to a thickness of 5 nm on the hole transport layer; a light-emitting layer is formed by co-depositing BH and BD to a thickness of 20 nm on the light-emitting auxiliary layer at a weight ratio of 98:2; an electron transport auxiliary layer is formed by depositing HB to a thickness of 5 nm on the light-emitting layer; an electron transport layer is formed by co-depositing a material for the electron transport layer and Liq to a thickness of 30 nm at a weight ratio of 1:1 on the electron transport auxiliary layer; an electron injection layer is formed by depositing LiF to a thickness of 1 nm on the electron transport layer; and a cathode is formed by depositing Al to a thickness of 100 nm on the electron injection layer. The structures of HI, HAT-CN6, EB, BH, BD, and Liq are shown in Table 1 above; the material of HB is shown in Table 3 below; and the material used for the electron transport layer is shown in Table 4 below.

[0408] [Table 3]

[0409]

[0410] [Table 4]

[0411]

[0412]

[0413] [Experimental Example]

[0414] [Experimental Example 1]: Evaluation of the performance of blue organic electroluminescent devices of Examples 1 to 20 and Comparative Examples 1 to 3

[0415] At 10 mA / cm 2 The driving voltage, EL peak value, and current efficiency of the organic electroluminescent devices fabricated in Examples 1 to 20 and Comparative Examples 1 to 3 were measured at a current density, and the results are shown in Table 5 below.

[0416] [Table 5]

[0417]

[0418]

[0419] As can be seen from Table 5, compared with the organic electroluminescent devices fabricated in Comparative Examples 1 to 3, the organic electroluminescent devices fabricated in Examples 1 to 20 exhibit superior driving voltage, EL peak value, and current efficiency.

[0420] [Experimental Example 2]: Performance evaluation of the blue organic electroluminescent devices of Examples 21 to 40 and Comparative Examples 4 to 6

[0421] At 10 mA / cm 2 The driving voltage, EL peak value, and current efficiency of the organic electroluminescent devices fabricated in Examples 21 to 40 and Comparative Examples 4 to 6 were measured at a current density, and the results are shown in Table 6 below.

[0422] [Table 6]

[0423]

[0424] As can be seen from Table 6, compared with the organic electroluminescent devices fabricated in Comparative Examples 4 to 6, the organic electroluminescent devices fabricated in Examples 21 to 40 exhibit superior driving voltage, EL peak value, and current efficiency.

[0425] Although embodiments of this disclosure have been disclosed, those skilled in the art will understand that various modifications, additions, and substitutions can be made without departing from the scope and spirit of this disclosure. Therefore, it is apparent that the exemplary embodiments described above are illustrative in all respects and do not limit this disclosure.

Claims

1. An organic light-emitting compound represented by Formula 1: [Formula 1] In Equation 1, A is a heteroarylene group containing 2 to 60 carbon atoms and having at least two nitrogen atoms, which may be unsubstituted or substituted. R is hydrogen, an alkyl group containing 1 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a haloalkyl group containing 1 to 40 carbon atoms, a heterocycloalkyl group containing 2 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylamine group containing 1 to 40 carbon atoms, an arylamine group containing 6 to 60 carbon atoms, an arylphosphin group containing 6 to 60 carbon atoms, an alkylphosphine oxide group containing 1 to 40 carbon atoms, an arylphosphine oxide group containing 6 to 60 carbon atoms, a carbonyl group, a cyano group, or a halogen group, each of which may be unsubstituted or substituted. L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the above groups is independently a single bond, an alkylene group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, or a heteroaryl group containing 2 to 60 carbon atoms, and each of these groups is either unsubstituted or substituted. Ar1 to Ar3 are each independently an aryl group containing 6 to 60 carbon atoms, or a heteroaryl group containing 2 to 60 carbon atoms, wherein each of the above groups is unsubstituted or substituted, and n is an integer from 0 to 5, where when n is from 2 to 5, each of the multiple L5 and R is independently the same or different from each other.

2. The organic light-emitting compound according to claim 1, wherein... A is a heteroarylene group containing 2 to 30 carbon atoms and having at least two nitrogen atoms, which is unsubstituted or substituted with the following groups: deuterium, alkyl containing 1 to 20 carbon atoms, cycloalkyl containing 3 to 20 carbon atoms, haloalkyl containing 1 to 20 carbon atoms, heterocycloalkyl containing 2 to 20 carbon atoms, aryl containing 6 to 30 carbon atoms, heteroaryl containing 2 to 30 carbon atoms, alkylsilyl containing 1 to 20 carbon atoms, alkylsulfonyl containing 1 to 20 carbon atoms, arylsilyl containing 6 to 30 carbon atoms, alkylamino containing 1 to 20 carbon atoms, arylamino containing 6 to 30 carbon atoms, arylphosphinyl containing 6 to 30 carbon atoms, alkylphosphine oxide containing 1 to 20 carbon atoms, arylphosphine oxide containing 6 to 30 carbon atoms, carbonyl, cyano, or halogen group. R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, an alkylsilyl group containing 1 to 20 carbon atoms, an arylsilyl group containing 6 to 30 carbon atoms, an alkylamino group containing 1 to 20 carbon atoms, an arylamino group containing 6 to 30 carbon atoms, an arylphosphinyl group containing 6 to 30 carbon atoms, an alkylphosphine oxide group containing 1 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a carbonyl group, a cyano group, or a halogen group, each of which is unsubstituted or modified by the following groups. Group substitution: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, heterocycloalkyl group containing 2 to 20 carbon atoms, aryl group containing 6 to 30 carbon atoms, heteroaryl group containing 2 to 30 carbon atoms, alkylsilyl group containing 1 to 20 carbon atoms, alkylsulfonyl group containing 1 to 20 carbon atoms, arylsilyl group containing 6 to 30 carbon atoms, alkylamino group having 1 to 20 carbon atoms, arylamino group having 6 to 30 carbon atoms, arylphosphinyl group having 6 to 30 carbon atoms, alkylphosphine oxide group having 1 to 20 carbon atoms, arylphosphine oxide group having 6 to 30 carbon atoms, carbonyl, cyano, or halogen group. L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each group is independently a single bond, an aryl group containing 6 to 30 carbon atoms, or a heteroaryl group containing 2 to 30 carbon atoms, wherein each of the above groups is unsubstituted or substituted by: deuterium, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a haloalkyl group containing 1 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, or an aryl group containing 2 to 30 carbon atoms. Heteroaryl, alkylsilyl group having 1 to 20 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkylsulfonyl group having 1 to 20 carbon atoms, alkylamino group having 1 to 20 carbon atoms, arylamino group having 6 to 30 carbon atoms, arylphosphinyl group having 6 to 30 carbon atoms, alkylphosphine oxide group having 1 to 20 carbon atoms, arylphosphine oxide group having 6 to 30 carbon atoms, carbonyl, cyano, or halogen group. Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms or a heteroaryl group containing 2 to 30 carbon atoms, each of which is unsubstituted or substituted with the following groups: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, heterocycloalkyl group containing 2 to 20 carbon atoms, aryl group containing 6 to 30 carbon atoms, and aryl group containing 2 to 30 carbon atoms. Heteroaryl, alkylsilyl group having 1 to 20 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkylsulfonyl group having 1 to 20 carbon atoms, alkylamino group having 1 to 20 carbon atoms, arylamino group having 6 to 30 carbon atoms, arylphosphinyl group having 6 to 30 carbon atoms, alkylphosphine oxide group having 1 to 20 carbon atoms, arylphosphine oxide group having 6 to 30 carbon atoms, carbonyl, cyano, or halogen group, and n is an integer from 0 to 5, where when n is from 2 to 5, each of the multiple L5 and R is independently the same or different from each other.

3. The organic light-emitting compound according to claim 1, wherein... A is a heteroarylene containing 2 to 30 carbon atoms and having at least two nitrogen atoms. R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a cyano group, or a halogen group, wherein each of the above groups is unsubstituted or substituted with a deuterium group, an alkyl group containing 1 to 20 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a cyano group, or a halogen group. L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the above groups is independently a single bond, an aryl group containing 6 to 30 carbon atoms, or a heteroaryl group containing 2 to 30 carbon atoms, wherein each of the above groups is unsubstituted or substituted with deuterium, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a carbonyl group. Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms or a heteroaryl group containing 2 to 30 carbon atoms, each of which is unsubstituted or substituted with the following groups: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, aryl group containing 6 to 30 carbon atoms, heteroaryl group containing 2 to 30 carbon atoms, alkylsilyl group containing 1 to 20 carbon atoms, arylsilyl group containing 6 to 30 carbon atoms, alkylsulfonyl group containing 1 to 20 carbon atoms, alkylphosphine oxide group having 1 to 20 carbon atoms, carbonyl group, cyano group or halogen group, and n is an integer from 1 to 3, where when n is 2 or 3, each of the multiple L5 and R is independently the same or different from each other.

4. The organic light-emitting compound according to claim 1, wherein... A is represented by any of the following formulas A-1 to A-15: [Formula A-1] [Formula A-2] [Formula A-3] [Formula A-4] [Formula A-5] [Formula A-6] [Formula A-7] [Formula A-8] [Formula A-9] [Formula A-10] [Formula A-11] [Formula A-12] [Formula A-13] [Formula A-14] [Formula A-15] In each of equations A-1 to A-15 * indicates the site that is bonded to L4 in Equation 1.

5. The organic light-emitting compound according to claim 1, wherein... A is a heteroarylene containing 2 to 30 carbon atoms and having at least two nitrogen atoms. R is hydrogen, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a cyano group, or a halogen group, wherein each of the above groups is unsubstituted or substituted with a deuterium group, an alkyl group containing 1 to 20 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a cyano group, or a halogen group. L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of the above groups is independently a single bond, an aryl group containing 6 to 30 carbon atoms, or a heteroaryl group containing 2 to 30 carbon atoms, wherein each of the above groups is unsubstituted or substituted with deuterium, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a carbonyl group. Ar1 to Ar3 are each independently an aryl group containing 6 to 30 carbon atoms or a heteroaryl group containing 2 to 30 carbon atoms, each of which is unsubstituted or substituted with the following groups: deuterium, alkyl group containing 1 to 20 carbon atoms, cycloalkyl group containing 3 to 20 carbon atoms, haloalkyl group containing 1 to 20 carbon atoms, aryl group containing 6 to 30 carbon atoms, heteroaryl group containing 2 to 30 carbon atoms, alkylsilyl group containing 1 to 20 carbon atoms, arylsilyl group containing 6 to 30 carbon atoms, alkylsulfonyl group containing 1 to 20 carbon atoms, alkylphosphine oxide group having 1 to 20 carbon atoms, carbonyl group, cyano group or halogen group, and n is an integer from 0 to 3, where when n is 2 or 3, each of the multiple L5 and R is independently the same or different from each other.

6. The organic light-emitting compound according to claim 1, wherein... A is any one of formulas A-1 to A-15. R is hydrogen, methyl, phenyl, biphenyl, naphthyl, benzophenanthryl, pyridyl, phenanthryl, phenanthrolyl, fluorenyl, dibenzothiophene, carbazole, phenoxathio, cyano, or fluorine, and each of the above groups is unsubstituted or substituted with deuterium, methyl, phenyl, pyridyl, or cyano. L1 to L5 are each independently generated by *–L a –L b –L c –L d -* indicates that L a To L d Each of these groups can be independently a single bond, phenylene, biphenylene, terphenylene, naphthylene, pyridylene, pyridazinylene, dibenzofuranylene, or benzoquinolineylene, and each of these groups can be unsubstituted or substituted with deuterium, naphthyl, dibenzofuranyl, or carbonyl. Ar1 to Ar3 are each independently phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, carbazole, fluorenyl, thiadiazolyl, oxadiazolyl, spirodifluorenyl, benzonaphthofuranyl, benzothiophene-pyrimidinyl, benzofuran-pyridinyl, dibenzofuranyl, naphthidyl, pyrimidinyl, phenanthrene, phenanthrene-pyrinyl, oxanthraceneyl, anthraceneyl, benzoxanthyl, triphenylsilyl, heptaazaphenarenyl, or acenaphthopyridinyl, each of the above groups being unsubstituted or substituted by the following groups: deuterium, methyl, butyl, phenyl, biphenyl, fluorenyl, pyridinyl, cyclohexyl, cyclopentyl, trimethylsilyl, carbonyl, methanesulfonyl, dimethylphosphine oxide, trifluoromethyl, cyano, or chlorine. n is an integer from 0 to 3, where when n is 2 or 3, each of the multiple L5s and Rs is independently the same or different from each other: [Formula A-1] [Formula A-2] [Formula A-3] [Formula A-4] [Formula A-5] [Formula A-6] [Formula A-7] [Formula A-8] [Formula A-9] [Formula A-10] [Formula A-11] [Formula A-12] [Formula A-13] [Formula A-14] [Formula A-15] In each of equations A-1 to A-15 * indicates the site that is bonded to L4 in Equation 1.

7. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound represented by formula 1 is selected from any one of compounds 1 to 162: 。 8. An organic electroluminescent device comprising an organic light-emitting compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, comprising: anode; cathode; A light-emitting layer disposed between the cathode and the anode; and An electron transport region is disposed between the cathode and the light-emitting layer. The electron transport region contains the organic light-emitting compound.

10. The organic electroluminescent device according to claim 9, wherein the electron transport region comprises at least one of an electron transport layer and an electron transport auxiliary layer, and The organic electroluminescent compound is contained in at least one of the electron transport layer and the electron transport auxiliary layer.

11. Use of the organic light-emitting compound according to any one of claims 1 to 7 in an organic electroluminescent device.

12. The use according to claim 11, wherein the organic light-emitting compound is used as an electron transport material for the organic electroluminescent device.

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