Organic light-emitting compound and organic electroluminescent device comprising same

Abstract

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

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2023-0166706, filed with the Korean Intellectual Property Office on November 27, 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] As shown below, NPB, BCP, Alq3, etc., are widely considered to be 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) have the advantage of improving efficiency and are used as blue, green, and red phosphorescent dopants, while 4,4-dicarbazolium biphenyl (CBP) is used as a phosphorescent host material.

[0009]

[0010] 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.

[0011] Therefore, there is a need to develop organic layer materials with excellent performance.

[0012] Existing technical documents

[0013] Korean Patent Publication No. 10-2019-0131391 Summary of the Invention

[0014] Technical issues

[0015] The embodiments disclosed herein provide novel compounds and their uses, which can be used as materials for organic layers in organic electroluminescent devices having excellent heat resistance and carrier transport capabilities, and particularly as materials for electron transport layers.

[0016] Furthermore, embodiments of this disclosure provide an organic light-emitting compound that exhibits high electron mobility by extending the LUMO (lowest unoccupied molecular orbital) region, and simultaneously has LUMO energy levels suitable for use as an organic layer for organic electroluminescent devices, particularly as a material for an electron transport layer.

[0017] The embodiments disclosed herein provide organic electroluminescent devices comprising novel organic light-emitting compounds that have low driving voltage, high luminous efficiency, and improved lifetime.

[0018] 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.

[0019] Technical solution

[0020] An embodiment of this disclosure provides an organic light-emitting compound represented by formula 1:

[0021] [Formula 1]

[0022]

[0023] In Equation 1,

[0024] X1 and X2 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N.

[0025] Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 carbon atoms, a cycloalkyl group containing 3 to 60 carbon atoms, a heterocycloalkyl group containing 2 to 60 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 alkylphosphine oxide group containing 2 to 40 carbon atoms, or an arylphosphine oxide group containing 6 to 60 carbon atoms, wherein each of the above groups is unsubstituted or substituted, and

[0026] L is an arylene containing 6 to 60 carbon atoms, each of which is either unsubstituted or substituted.

[0027] The embodiments disclosed herein provide an organic electroluminescent device containing an organic light-emitting compound.

[0028] The embodiments disclosed herein provide the use of organic light-emitting compounds in organic electroluminescent devices.

[0029] Beneficial effects

[0030] The organic light-emitting compounds according to this disclosure have LUMO (lowest unoccupied molecular orbital) regions widely distributed throughout the molecular region, thereby exhibiting high electron mobility, and can also have LUMO energy levels suitable for use as electron transport layers for organic electroluminescent devices.

[0031] Furthermore, organic electroluminescent devices containing organic light-emitting compounds according to this disclosure can greatly improve light-emitting performance, driving voltage, lifetime, efficiency, etc., thereby making them more effective for use in full-color display panels, etc.

[0032] 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

[0033] 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.

[0034] 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.

[0035] 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.

[0036] The embodiments of this disclosure will be described in detail below.

[0037] 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.

[0038] As used herein, the term "aryl" can refer to a monovalent functional group derived from an aromatic hydrocarbon. Aryl groups can include, for example, phenyl, naphthyl group, anthraceneyl group, tetraphenyl, pyrene, tolyl, biphenyl, terphenyl, chrysenyl group (or trefyl), spirodifluorenyl, fluorenyl group, perylene, indole, azulel, hepta-enyl, phenalenyl group (or benzo[a]- ...

[0039] 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, triazolyl, tetrazolyl, benzotriazolyl, pyrazolyl, imidazole, benzimidazole, indolyl, isoyindolyl, and indolizinyl. Groups, also known as nitrogen-containing indenyl groups, include purine, indazole, quinolinyl, isoquinolinyl, quinazinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cenolinyl, pteridinyl, imidazotriazinyl, acridineyl, phenanthridineyl, carbazoleyl, phenanthrolinyl, phenazinyl, imidazopyridyl, imidazopyrimidyl, pyrazolyl, etc.; sulfur-containing heteroaryl groups include thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzonaphthothiopheneyl, etc.; oxygen-containing heteroaryl groups include furanyl, pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, etc. 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 the number of carbon (C) atoms. For example, the number of nuclear atoms in each of the heteroaryls can be 5 to 60, 5 to 30, or 5 to 20.

[0040] As used herein, the term "alkyl" can refer to a monovalent functional group derived from a saturated hydrocarbon having a straight-chain or branched structure. Alkyl groups can include, for example, 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., but are not limited thereto.

[0041] As used herein, the term "cycloalkyl" can refer to a monovalent functional group derived from a saturated hydrocarbon having a cyclic structure. Cycloalkyl groups can include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclononyl, adamantyl, etc.

[0042] 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 heteroaryl group 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 group 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 a carbon (C) atom. For example, the number of nuclear atoms in a heterocyclic alkyl group can be 5 to 60, 5 to 30, or 5 to 20.

[0043] As used herein, the terms "alkylsilyl" and "arylsilyl" can refer, respectively, to a monovalent functional group derived from a compound in which at least one hydrogen atom of a silane is substituted by the aforementioned alkyl and aryl groups. Arylsilyl can be, for example, triphenylsilyl, but is not limited thereto.

[0044] As used herein, the terms "alkylphosphine oxide" and "arylphosphine oxide" can each refer to a monovalent functional group derived from a compound in which the aforementioned alkyl or aryl groups are respectively substituted on a phosphine oxide. Alkylphosphine oxide can be, for example, dimethylphosphine oxide, and arylphosphine oxide can be, for example, a triphenylphosphine oxide group, but are not limited thereto.

[0045] As used herein, the term "substitution" can refer to substitution by at least one substituent selected from the group consisting of deuterium, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 carbon atoms, a heterocycloalkyl group containing 5 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group. When substituted by multiple substituents, the substituents can be the same as or different from each other.

[0046] <Organic luminescent compounds>

[0047] This disclosure provides a novel organic light-emitting compound. The organic light-emitting compound is represented by the following formula 1.

[0048] [Formula 1]

[0049]

[0050] In Equation 1,

[0051] X1 and X2 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N.

[0052] Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 carbon atoms, a cycloalkyl group containing 3 to 60 carbon atoms, a heterocycloalkyl group containing 2 to 60 carbon atoms, a heterocycloalkyl group containing 5 to 60 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 alkylphosphine oxide group containing 2 to 40 carbon atoms, or an arylphosphine oxide group containing 6 to 60 carbon atoms, wherein each of the above groups is unsubstituted or substituted, and

[0053] L is an arylene containing 6 to 60 carbon atoms, each of which is either unsubstituted or substituted.

[0054] Specifically, at least one of the following groups, which may be present as Ar1 to Ar4 and L: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylphosphine oxide, or arylphosphine oxide, is independently unsubstituted or substituted by at least one group selected from the following groups: deuterium, alkyl containing 1 to 20 carbon atoms, cycloalkyl containing 3 to 30 carbon atoms, heterocycloalkyl containing 2 to 30 carbon atoms, heterocycloalkyl containing 5 to 30 nuclear atoms, aryl containing 6 to 30 carbon atoms, heteroaryl containing 2 to 30 carbon atoms, heteroaryl containing 5 to 30 nuclear atoms, alkylsilyl containing 1 to 20 carbon atoms, arylsilyl containing 6 to 30 carbon atoms, alkylphosphine oxide containing 2 to 20 carbon atoms, arylphosphine oxide containing 6 to 30 carbon atoms, nitrile, or halogen group. When substituted by multiple substituents, the substituents may be the same as or different from each other.

[0055] In one implementation scheme, in Equation 1,

[0056] X1 and X2 are each independently either N or CH, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N.

[0057] Ar1 to Ar4 are each independently an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 carbon atoms, a heterocycloalkyl group containing 5 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, or an arylphosphine oxide group containing 6 to 30 carbon atoms. One is unsubstituted or substituted with an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 carbon atoms, a heterocycloalkyl group containing 5 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group, and

[0058] L is an arylene containing 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 carbon atoms, a heterocycloalkyl group containing 5 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group.

[0059] In one implementation scheme, in Equation 1,

[0060] X1 and X2 are each independently either N or CH, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N.

[0061] Ar1 to Ar4 are each independently composed of an aryl group containing 6 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, a heteroaryl group containing 5 to 20 nuclear atoms, an alkylsilyl group containing 1 to 10 carbon atoms, an arylsilyl group containing 6 to 20 carbon atoms, an alkylphosphine oxide group containing 2 to 10 carbon atoms, or an arylphosphine oxide group containing 6 to 20 carbon atoms, wherein each of the above groups is unsubstituted or substituted with an alkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, an aryl group containing 6 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, a heteroaryl group containing 5 to 20 nuclear atoms, an alkylsilyl group containing 1 to 10 carbon atoms, an arylsilyl group containing 6 to 20 carbon atoms, an alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group.

[0062] L is an arylene containing 6 to 20 carbon atoms, each of which is either unsubstituted or substituted with a nitrile group.

[0063] In one implementation scheme, in Equation 1,

[0064] X1 and X2 are each independently either N or CH, provided that only one of X1 and X2 is N.

[0065] Ar1 to Ar4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthrene, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoleyl, or triphenylphosphine oxide, each of which is unsubstituted or substituted with methyl, phenyl, pyridyl, carbazoleyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphine oxide, triphenylsilyl, nitrile, or fluorine, or each of which can form a fused ring structure.

[0066] L is phenylene or naphthylene, each of which is unsubstituted or substituted with a nitrile group.

[0067] Organic light-emitting compounds represented by Formula 1 can be represented by Formula 2 or Formula 3.

[0068] [Equation 2]

[0069]

[0070] [Formula 3]

[0071]

[0072] In equations 2 and 3,

[0073] Ar1 to Ar4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthrene, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoleyl, or triphenylphosphine oxide, each of which is unsubstituted or substituted with methyl, phenyl, pyridyl, carbazoleyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphine oxide, triphenylsilyl, nitrile, or fluorine, or each of which can form a fused ring structure.

[0074] L can be any one of the groups consisting of free formulas L-1 to L-15.

[0075] [Equation L-1] [Equation L-2]

[0076]

[0077] [Equation L-3] [Equation L-4]

[0078]

[0079] [Equation L-5] [Equation L-6]

[0080]

[0081] [Formula L-7] [Formula L-8]

[0082]

[0083] [Formula L-9] [Formula L-10]

[0084]

[0085] [Formula L-11] [Formula L-12]

[0086]

[0087] [Equation L-13] [Equation L-14]

[0088]

[0089] [Formula L-15]

[0090]

[0091] In each of formulas L-1 to L-15, * denotes the binding site with formula 1.

[0092] In one implementation, in formula 2 or formula 3,

[0093] Ar1 through Ar4 are each independently phenyl, biphenyl, tolyl, naphthyl, fluorenyl, dibenzofuranyl, or carbazoleyl, and each of these groups is either unsubstituted or substituted with methyl, phenyl, or carbazoleyl.

[0094] L can be any one of the groups consisting of free formulas L-1 to L-3 and L-5.

[0095] [Equation L-1] [Equation L-2]

[0096]

[0097] [Formula L-3] [Formula L-5]

[0098]

[0099] In each of formulas L-1 to L-3 and L-5, * denotes the binding site with formula 1.

[0100] In one embodiment, the organic light-emitting compound represented by Formula 1 may be any one of the compounds selected from 001 to 336.

[0101]

[0102]

[0103]

[0104]

[0105]

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[0183]

[0184]

[0185] As a specific example, the compound represented by Formula 1 can be selected from any one of compounds 004, 009, 015, 019, 044, 060, 067, 075, 082, 100, 116, 121, 127, 131, 156, 281, 284, 305, 312, 319, 326 and 331.

[0186] The novel organic light-emitting compounds according to this disclosure have a structure in which an additional pyrimidine is attached to the 4-position of the pyrimidine via a phenylene or naphthylene group, thereby exhibiting rapid electron transport properties and a LUMO energy level suitable for use as an electron transport layer material, and thus providing excellent electron transfer capability to adjacent layers.

[0187] 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.

[0188] Organic electroluminescent devices

[0189] 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.

[0190] 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.

[0191] anode

[0192] 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.

[0193] There are no particular limitations on the type of anode material, and it 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. Such compounds can be used alone or in combination of two or more of them.

[0194] 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.

[0195] cathode

[0196] The organic electroluminescent device disclosed herein includes a cathode. The cathode is used to inject electrons into the organic layer.

[0197] 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.

[0198] Emissive layer

[0199] 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.

[0200] 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.

[0201] 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.

[0202] Electronic transmission area

[0203] The organic electroluminescent device disclosed herein includes an electron transport region disposed between the light-emitting layer and the cathode.

[0204] 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.

[0205] 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: lanthanides, such as LiF, Li₂O, BaO, NaCl, CsF, and Yb; and metal halides, such as RbCl and RbI.

[0206] 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 structure in which an additional pyrimidine is attached to the 4-position of the pyrimidine via a phenylene or naphthylene group, thereby exhibiting rapid electron transport characteristics and a LUMO energy level suitable for use as an electron transport layer material, and thus providing excellent electron transfer capability to adjacent layers. Therefore, when the novel organic light-emitting compound according to the present disclosure is used as an electron transport layer material, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0207] 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.

[0208] 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.

[0209] Electron transport auxiliary layer

[0210] 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.

[0211] The electron transport auxiliary 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 structure in which an additional pyrimidine is attached to the 4-position of the pyrimidine via a phenylene or naphthylene group, thereby exhibiting rapid electron transport characteristics and a LUMO energy level suitable for use as an electron transport layer material, and thus providing excellent electron transfer capability to adjacent layers. Therefore, when the novel organic light-emitting compound according to the present disclosure is used as an electron transport auxiliary layer material, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0212] 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.

[0213] Hole transport region

[0214] 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.

[0215] 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.

[0216] 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.

[0217] 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. These compounds can be used alone or in combination of two or more of them.

[0218] Furthermore, the hole transport material can be selected from hole transport materials 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'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline]), etc. Such compounds can be used alone or in combination of two or more of them.

[0219] 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.

[0220] Hole transport auxiliary layer

[0221] 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.

[0222] 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.

[0223] 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.

[0224] Cover layer

[0225] 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.

[0226] 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.

[0227] 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.

[0228] 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).

[0229] 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.

[0230] In one embodiment, the organic light-emitting compound can be used as an electron transport material in an organic electroluminescent device.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] [Preparation Example]

[0235] [Preparation Example 1]: Synthesis of P2-1

[0236]

[0237] 4-Chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), [1,1'-biphenyl]-4-ylboronic acid (19.7 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-1 (4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine) (33.4 g, 79.7 mmol, 80% yield).

[0238] Mass spectrometry: [(M+H)] + ]:420

[0239] [Preparation Example 2]: Synthesis of P2-2

[0240]

[0241] 4-Chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid (27.3 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 hours in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane. The extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-2 (4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine) (40.4 g, 81.7 mmol, yield 82%).

[0242] Mass spectrometry: [(M+H)] + ]:496

[0243] [Preparation Example 3]: Synthesis of P2-3

[0244]

[0245] 4-Chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (9-phenyl-9H-carbazole-2-yl)boronic acid (28.6 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with a mixture of toluene (360 ml), EtOH (60 ml), and water (60 ml) under heat and reflux with stirring for 2 hours. After the reaction was complete, the product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-3 (2-(6-(3-chlorophenyl)-2-phenylpyrimidine-4-yl)-9-phenyl-9H-carbazole) (38.5 g, 75.7 mmol, yield 76%).

[0246] Mass spectrometry: [(M+H)] + ]:509

[0247] [Preparation Example 4]: Synthesis of P2-4

[0248]

[0249] 4-Chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazole-9-yl)phenyl)boronic acid (287.13 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 hours in the presence of a mixed solvent of toluene (360 ml), EtOH (60 ml), and water (60 ml). After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-4 (9-(3-(6-(3-chlorophenyl)-2-phenylpyrimidine-4-yl)phenyl)-9H-carbazole (43.0 g, 84.7 mmol, yield 85%).

[0250] Mass spectrometry: [(M+H)] + ]:509

[0251] [Preparation Example 5]: Synthesis of P2-5

[0252]

[0253] 4-Chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), naphth-2-ylboronic acid (17.1 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of toluene (360 ml), EtOH (60 ml), and water (60 ml). After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-5 (4-(3-chlorophenyl)-6-(naphth-2-yl)-2-phenylpyrimidine) (32.5 g, 88.7 mmol, yield 89%).

[0254] Mass spectrometry: [(M+H)] + ]:368

[0255] [Preparation Example 6]: Synthesis of P2-6

[0256]

[0257] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), [1,1'-biphenyl]-4-ylboronic acid (19.7 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-6 (2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine) (31.3 g, 74.7 mmol, yield 75%).

[0258] Mass spectrometry: [(M+H)] + ]:420

[0259] [Preparation Example 7]: Synthesis of P2-7

[0260]

[0261] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), dibenzo[b,d]furan-3-ylboronic acid (21.1 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-7 (4-(3-chlorophenyl)-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine) (36.2 g, 83.7 mmol, yield 84%).

[0262] Mass spectrometry: [(M+H)] + ]:434

[0263] [Preparation Example 8]: Synthesis of P2-8

[0264]

[0265] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazole-9-yl)phenyl)boronic acid (28.6 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 hours in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-8 (9-(3-(4-(3-chlorophenyl)-6-phenylpyrimidine-2-yl)phenyl)-9H-carbazole) (42.0 g, 82.7 mmol, yield 83%).

[0266] Mass spectrometry: [(M+H)] + ]:509

[0267] [Preparation Example 9]: Synthesis of P2-9

[0268]

[0269] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), (9,9-dimethyl-9H-fluorene-2-yl)boronic acid (23.7 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 hours in the presence of a mixed solvent of toluene (360 ml), EtOH (60 ml), and water (60 ml). After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-9 (4-(3-chlorophenyl)-2-(9,9-dimethyl-9H-fluorene-2-yl)-6-phenylpyrimidine) (37.5 g, 81.7 mmol, yield 82%).

[0270] Mass spectrometry: [(M+H)] + ]:460

[0271] [Preparation Example 10]: Synthesis of P2-10

[0272]

[0273] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), naphth-2-ylboronic acid (17.1 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with a mixture of toluene (360 ml), EtOH (60 ml), and water (60 ml) under heat and reflux with stirring for 2 hours. After the reaction was complete, the product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-10 (4-(3-chlorophenyl)-2-(naphth-2-yl)-6-phenylpyrimidine) (32.1 g, 81.7 mmol, yield 82%).

[0274] Mass spectrometry: [(M+H)] + ]:394

[0275] [Preparation Example 11]: Synthesis of P2-11

[0276]

[0277] 4-Chloro-6-(2-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), [1,1'-biphenyl]-4-ylboronic acid (19.7 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-11 (4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine) (33.4 g, 79.7 mmol, 80% yield).

[0278] Mass spectrometry: [(M+H)] + ]:420

[0279] [Preparation Example 12]: Synthesis of P2-12

[0280]

[0281] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (30.0 g, 87.5 mmol), (3-chloronaphth-1-yl)boronic acid (18.1 g, 87.5 mmol), Pd(PPh3)4 (3.0 g, 2.6 mmol), and K2CO3 (36.3 g, 262.5 mmol) were reacted with stirring under heating and reflux for 2 h in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-12 (4-([1,1'-biphenyl]-4-yl)-6-(3-chloronaphth-1-yl)-2-phenylpyrimidine) (32.8 g, 70.0 mmol, 80% yield).

[0282] Mass spectrometry: [(M+H)] + ]:470

[0283] [Preparation Example 13]: Synthesis of P2-13

[0284]

[0285] 2,4-Dichloro-6-(3-chlorophenyl)pyrimidine (30.0 g, 115.6 mmol), [1,1'-biphenyl]-4-ylboronic acid (45.8 g, 231.2 mmol), Pd(PPh3)4 (4.0 g, 3.5 mmol), and K2CO3 (47.9 g, 346.8 mmol) were reacted with a mixture of 360 ml toluene, 60 ml EtOH, and 60 ml water under stirring and heating under reflux for 2 hours. After the reaction was complete, the product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-13 (2,4-di([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)pyrimidine) (45.8 g, 92.5 mmol, 80% yield).

[0286] Mass spectrometry: [(M+H)] + ]:496

[0287] [Preparation Example 14]: Synthesis of P2-14

[0288]

[0289] 4,6-Dichloro-2-(3-chlorophenyl)pyrimidine (30.0 g, 115.6 mmol), [1,1'-biphenyl]-4-ylboronic acid (45.8 g, 231.2 mmol), Pd(PPh3)4 (4.0 g, 3.5 mmol), and K2CO3 (47.9 g, 346.8 mmol) were reacted with a mixture of 360 ml toluene, 60 ml EtOH, and 60 ml water under stirring and heating under reflux for 2 hours. After the reaction was complete, the product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-14 (4,6-di([1,1'-biphenyl]-4-yl)-2-(3-chlorophenyl)pyrimidine) (45.2 g, 91.3 mmol, yield 79%).

[0290] Mass spectrometry: [(M+H)] + ]:496

[0291] [Preparation Example 15]: Synthesis of P2-15

[0292]

[0293] 4-Chloro-6-(2-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), dibenzo[b,d]furan-3-ylboronic acid (21.1 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with stirring under heating and reflux for 2 hours in the presence of a mixed solvent of 360 ml toluene, 60 ml EtOH, and 60 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-15 (4-(2-chlorophenyl)-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine) (30.7 g, 83.7 mmol, yield 84%).

[0294] Mass spectrometry: [(M+H)] + ]:368

[0295] [Preparation Example 16]: Synthesis of P2-16

[0296]

[0297] 4-Chloro-6-(4-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazole-9-yl)phenyl)boronic acid (28.6 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), and K2CO3 (41.3 g, 298.8 mmol) were reacted with a mixture of toluene (360 ml), EtOH (60 ml), and water (60 ml) under heat and reflux with stirring for 2 hours. After the reaction was complete, the product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound P2-16 (9-(3-(6-(4-chlorophenyl)-2-phenylpyrimidine-4-yl)phenyl)-9H-carbazole (43.0 g, 84.7 mmol, yield 85%).

[0298] Mass spectrometry: [(M+H)] + ]:509

[0299] [Preparation Example 17]: Synthesis of P1-1

[0300]

[0301] Compound P2-1 (30 g, 71.6 mmol), bis(pinacol)diboron (23.6 g, 93.1 mmol), Pd(dppf)Cl2 (1.6 g, 2.1 mmol), X-Phos (2.0 g, 4.3 mmol), and KOAc (14.1 g, 143.2 mmol), synthesized in Preparation Example 1, was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-1 (4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (29.2 g, 57.3 mmol, yield 80%).

[0302] Mass spectrometry: [(M+H)] + ]:511

[0303] [Preparation Example 18]: Synthesis of P1-2

[0304]

[0305] Compounds P2-2 (30 g, 60.6 mmol), bis(pinacol)diboron (20.0 g, 78.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.6 mmol), and KOAc (11.9 g, 121.2 mmol), synthesized in Preparation Example 2, were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-2 (4-([1,1':3',1''-terphenyl]-5'-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (30.2 g, 51.5 mmol, yield 85%).

[0306] Mass spectrometry: [(M+H)] + ]:588

[0307] [Preparation Example 19]: Synthesis of P1-3

[0308]

[0309] Compound P2-3 (30 g, 59.1 mmol), synthesized in Preparation Example 3, along with bis(pinacol)diboron (19.5 g, 76.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.5 mmol), and KOAc (11.6 g, 118.1 mmol), was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-3 (9-phenyl-2-(2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidin-4-yl)-9H-carbazole) (30.1 g, 50.2 mmol, yield 85%).

[0310] Mass spectrometry: [(M+H)] + ]:601

[0311] [Preparation Example 20]: Synthesis of P1-4

[0312]

[0313] Compounds P2-4 (30 g, 59.1 mmol), bis(pinacol)diboron (19.5 g, 76.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.5 mmol), and KOAc (11.6 g, 118.1 mmol), synthesized in Preparation Example 4, were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-4 (9-(3-(2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidin-4-yl)phenyl)-9H-carbazole) (31.9 g, 53.1 mmol, 90% yield).

[0314] Mass spectrometry: [(M+H)] + ]:601

[0315] [Preparation Example 21]: Synthesis of P1-5

[0316]

[0317] Compound P2-5 (30 g, 76.4 mmol), synthesized in Preparation Example 5, along with bis(pinacol)diboron (25.2 g, 99.3 mmol), Pd(dppf)Cl2 (1.7 g, 2.3 mmol), X-Phos (2.2 g, 4.6 mmol), and KOAc (15.0 g, 152.7 mmol), was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-5 (4-(naphthyl-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidine) (31.8 g, 65.7 mmol, yield 86%).

[0318] Mass spectrometry: [(M+H)] + ]:485

[0319] [Preparation Example 22]: Synthesis of P1-6

[0320]

[0321] Compound P2-6 (30 g, 71.6 mmol), synthesized in Preparation Example 6, along with bis(pinacol)diboron (23.6 g, 93.1 mmol), Pd(dppf)Cl2 (1.6 g, 2.1 mmol), X-Phos (2.0 g, 4.3 mmol), and KOAc (14.1 g, 143.2 mmol), was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-6 (2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidine) (32.2 g, 63.0 mmol, yield 88%).

[0322] Mass spectrometry: [(M+H)] + ]:511

[0323] [Preparation Example 23]: Synthesis of P1-7

[0324]

[0325] Compounds P2-7 (30 g, 69.3 mmol), bis(pinacol)diboron (22.9 g, 90.1 mmol), Pd(dppf)Cl2 (1.5 g, 2.1 mmol), X-Phos (2.0 g, 4.2 mmol), and KOAc (13.6 g, 138.6 mmol), synthesized in Preparation Example 7, were added to 300 ml of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-7 (2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (31.3 g, 59.6 mmol, yield 86%).

[0326] Mass spectrometry: [(M+H)] + ]:525

[0327] [Preparation Example 24]: Synthesis of P1-8

[0328]

[0329] Compounds P2-8 (30 g, 59.1 mmol), bis(pinacol)diboron (19.5 g, 76.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.5 mmol), and KOAc (11.6 g, 118.1 mmol), synthesized in Preparation Example 8, were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-8 (9-(3-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidin-2-yl)phenyl)-9H-carbazole) (31.2 g, 52.0 mmol, yield 88%).

[0330] Mass spectrometry: [(M+H)] + ]:601

[0331] [Preparation Example 25]: Synthesis of P1-9

[0332]

[0333] Compound P2-9 (30 g, 65.4 mmol), synthesized in Preparation Example 9, bis(pinacol)diboron (21.6 g, 85.0 mmol), Pd(dppf)Cl2 (1.4 g, 2.0 mmol), X-Phos (1.9 g, 3.9 mmol), and KOAc (12.8 g, 130.7 mmol) were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-9 (2-(9,9-dimethyl-9H-fluoren-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (32.0 g, 58.2 mmol, yield 89%).

[0334] Mass spectrometry: [(M+H)] + ]:552

[0335] [Preparation Example 26]: Synthesis of P1-10

[0336]

[0337] Compound P2-10 (30 g, 76.4 mmol), synthesized in Preparation Example 10, along with bis(pinacol)diboron (25.2 g, 99.3 mmol), Pd(dppf)Cl2 (1.7 g, 2.3 mmol), X-Phos (2.2 g, 4.6 mmol), and KOAc (15.0 g, 152.7 mmol), was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-10 (2-(naphthyl-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidine) (29.2 g, 60.3 mmol, yield 79%).

[0338] Mass spectrometry: [(M+H)] + ]:485

[0339] [Preparation Example 27]: Synthesis of P1-11

[0340]

[0341] Compound P2-11 (30 g, 71.6 mmol), bis(pinacol)diboron (23.6 g, 93.1 mmol), Pd(dppf)Cl2 (1.6 g, 2.1 mmol), X-Phos (2.0 g, 4.3 mmol), and KOAc (14.1 g, 143.2 mmol), synthesized in Preparation Example 11, were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-11 (4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (30.7 g, 60.2 mmol, yield 84%).

[0342] Mass spectrometry: [(M+H)] + ]:511

[0343] [Preparation Example 28]: Synthesis of P1-12

[0344]

[0345] Compound P2-12 (30 g, 64.0 mmol), bis(pinacol)diboron (21.1 g, 83.2 mmol), Pd(dppf)Cl2 (1.4 g, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), and KOAc (12.6 g, 127.9 mmol), synthesized in Preparation Example 12, was added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-12 (4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)naphth-1-yl)pyrimidine) (29.8 g, 53.1 mmol, yield 83%).

[0346] Mass spectrometry: [(M+H)] + ]:562

[0347] [Preparation Example 29]: Synthesis of P1-13

[0348]

[0349] Compound P2-13 (30 g, 60.6 mmol), synthesized in Preparation Example 13, bis(pinacol)diboron (20.0 g, 78.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.6 mmol), and KOAc (11.9 g, 121.2 mmol) were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-13 (2,4-bis([1,1'-biphenyl]-4-yl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (29.5 g, 50.3 mmol, yield 83%).

[0350] Mass spectrometry: [(M+H)] + ]:588

[0351] [Preparation Example 30]: Synthesis of P1-14

[0352]

[0353] Compound P2-14 (30 g, 60.6 mmol), synthesized in Preparation Example 14, bis(pinacol)diboron (20.0 g, 78.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.6 mmol), and KOAc (11.9 g, 121.2 mmol) were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-14 (4,6-bis([1,1'-biphenyl]-4-yl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (29.9 g, 50.9 mmol, yield 84%).

[0354] Mass spectrometry: [(M+H)] + ]:588

[0355] [Preparation Example 31]: Synthesis of P1-15

[0356]

[0357] Compound P2-15 (30 g, 69.3 mmol), synthesized in Preparation Example 15, bis(pinacol)diboron (22.9 g, 90.1 mmol), Pd(dppf)Cl2 (1.5 g, 2.1 mmol), X-Phos (2.0 g, 4.2 mmol), and KOAc (13.6 g, 138.6 mmol) were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-15 (4-(dibenzo[b,d]furan-3-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)pyrimidine) (30.9 g, 58.9 mmol, yield 85%).

[0358] Mass spectrometry: [(M+H)] + ]:525

[0359] [Preparation Example 32]: Synthesis of P1-16

[0360]

[0361] Compound P2-16 (30 g, 59.1 mmol), synthesized in Preparation Example 16, bis(pinacol)diboron (19.5 g, 76.8 mmol), Pd(dppf)Cl2 (1.3 g, 1.8 mmol), X-Phos (1.7 g, 3.5 mmol), and KOAc (11.6 g, 118.1 mmol) were added to 300 mL of 1,4-dioxane and reacted under stirring at reflux for 6 hours. After the reaction was complete, the reaction product was filtered to remove KOAc, the organic layer was concentrated, and then crystallized with acetone and MeOH to give compound P1-16 (9-(3-(2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)pyrimidin-4-yl)phenyl)-9H-carbazole) (28.7 g, 47.8 mmol, yield 81%).

[0362] Mass spectrometry: [(M+H)] + ]:601

[0363] [Synthesis example]

[0364] [Synthetic Example 1]: Synthesis of Compound 004

[0365]

[0366] Compound P1-1 (15.0 g, 29.4 mmol), synthesized in Preparation Example 17, 4-chloro-2,6-diphenylpyrimidine (7.8 g, 29.4 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.2 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 004 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-2-phenylpyrimidine) (15.4 g, 25.0 mmol, yield 85%).

[0367] Mass spectrometry: [(M+H)] + ]:616

[0368] [Synthetic Example 2]: Synthesis of Compound 009

[0369]

[0370] P1-2 (15.0 g, 25.6 mmol), 4-chloro-2,6-diphenylpyrimidine (6.8 g, 25.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.6 g, 76.7 mmol), synthesized in Preparation Example 18, were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 009 (4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-2-phenylpyrimidine) (14.8 g, 21.5 mmol, yield 84%).

[0371] Mass spectrometry: [(M+H)] + ]:692

[0372] [Synthetic Example 3]: Synthesis of Compound 015

[0373]

[0374] Compound P1-3 (15.0 g, 25.0 mmol), synthesized in Preparation Example 19, 4-chloro-2,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound O15 (2-(6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidin-4-yl)-9-phenyl-9H-carbazole) (14.6 g, 20.8 mmol, yield 83%).

[0375] Mass spectrometry: [(M+H)] + ]:705

[0376] [Synthetic Example 4]: Synthesis of Compound 019

[0377]

[0378] Compound P1-4 (15.0 g, 25.0 mmol), synthesized in Preparation Example 20, 4-chloro-2,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound O19 (9-(3-(6-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-2-phenylpyrimidine-4-yl)phenyl)-9H-carbazole (14.8 g, 21.0 mmol, yield 84%).

[0379] Mass spectrometry: [(M+H)] + ]:705

[0380] [Synthetic Example 5]: Synthesis of Compound 044

[0381]

[0382] Compound P1-5 (15.0 g, 31.0 mmol), synthesized in Preparation Example 21, 4-chloro-2,6-diphenylpyrimidine (8.3 g, 31.0 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (12.8 g, 92.9 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 044 (4-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-6-(naphth-2-yl)-2-phenylpyrimidine) (15.3 g, 26.0 mmol, yield 84%).

[0383] Mass spectrometry: [(M+H)] + ]:590

[0384] [Synthesis Example 6]: Synthesis of Compound 060

[0385]

[0386] Compound P1-6 (15.0 g, 29.4 mmol), synthesized in Preparation Example 22, 4-chloro-2,6-diphenylpyrimidine (7.8 g, 29.4 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.2 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 060 (2-([1,1'-biphenyl]-4-yl)-4-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-6-phenylpyrimidine) (16.1 g, 26.2 mmol, yield 89%).

[0387] Mass spectrometry: [(M+H)] + ]:616

[0388] [Synthetic Example 7]: Synthesis of Compound 067

[0389]

[0390] Compound P1-7 (15.0 g, 28.6 mmol), synthesized in Preparation Example 23, 4-chloro-2,6-diphenylpyrimidine (7.6 g, 28.6 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (11.9 g, 85.8 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 067 (2-(dibenzo[b,d]furan-3-yl)-4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-phenylpyrimidine (15.5 g, 24.6 mmol, yield 86%).

[0391] Mass spectrometry: [(M+H)] + ]:630

[0392] [Synthetic Example 8]: Synthesis of Compound 075

[0393]

[0394] Compound P1-8 (15.0 g, 25.0 mmol), synthesized in Preparation Example 24, 4-chloro-2,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 075 (9-(3-(4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-phenylpyrimidin-2-yl)phenyl)-9H-carbazole (15.3 g, 21.8 mmol, yield 87%).

[0395] Mass spectrometry: [(M+H)] + ]:705

[0396] [Synthesis Example 9]: Synthesis of Compound 082

[0397]

[0398] Compound P1-9 (15.0 g, 27.2 mmol), synthesized in Preparation Example 25, 4-chloro-2,6-diphenylpyrimidine (7.3 g, 27.2 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.3 g, 81.7 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 082 (2-(9,9-dimethyl-9H-fluorene-2-yl)-4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-phenylpyrimidine (15.5 g, 23.7 mmol, yield 87%).

[0399] Mass spectrometry: [(M+H)] + ]:656

[0400] [Synthetic Example 10]: Synthesis of Compound 100

[0401]

[0402] Compound P1-10 (15.0 g, 31.0 mmol), synthesized in Preparation Example 26, 4-chloro-2,6-diphenylpyrimidine (8.3 g, 31.0 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (12.8 g, 92.9 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 100 (4-(3-(2,6-diphenylpyrimidine-4-yl)phenyl)-2-(naphth-2-yl)-6-phenylpyrimidine (15.5 g, 26.3 mmol, yield 85%).

[0403] Mass spectrometry: [(M+H)] + ]:590

[0404] [Synthetic Example 11]: Synthesis of Compound 116

[0405]

[0406] Compound P1-1 (15.0 g, 29.4 mmol), synthesized in Preparation Example 17, 2-chloro-4,6-diphenylpyrimidine (7.8 g, 29.4 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.2 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 116 (4-([1,1'-biphenyl]-4-yl)-6-(3-(4,6-diphenylpyrimidine-2-yl)phenyl)-2-phenylpyrimidine) (15.2 g, 24.7 mmol, yield 84%).

[0407] Mass spectrometry: [(M+H)] + ]:616

[0408] [Synthetic Example 12]: Synthesis of Compound 121

[0409]

[0410] Compound P1-2 (15.0 g, 25.6 mmol), synthesized in Preparation Example 18, 2-chloro-4,6-diphenylpyrimidine (6.8 g, 25.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.6 g, 76.7 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 121 (4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-(4,6-diphenylpyrimidine-2-yl)phenyl)-2-phenylpyrimidine) (14.1 g, 20.5 mmol, yield 80%).

[0411] Mass spectrometry: [(M+H)] + ]:692

[0412] [Synthetic Example 13]: Synthesis of Compound 127

[0413]

[0414] Compound P1-3 (15.0 g, 25.0 mmol), synthesized in Preparation Example 19, 2-chloro-4,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 127 (2-(6-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-2-phenylpyrimidin-4-yl)-9-phenyl-9H-carbazole) (14.6 g, 20.8 mmol, yield 83%).

[0415] Mass spectrometry: [(M+H)] + ]:705

[0416] [Synthetic Example 14]: Synthesis of Compound 131

[0417]

[0418] Compound P1-4 (15.0 g, 25.0 mmol), synthesized in Preparation Example 20, 2-chloro-4,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 131 (9-(3-(6-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-2-phenylpyrimidin-4-yl)phenyl)-9H-carbazole (13.9 g, 19.8 mmol, yield 79%).

[0419] Mass spectrometry: [(M+H)] + ]:705

[0420] [Synthetic Example 15]: Synthesis of Compound 156

[0421]

[0422] Compound P1-5 (15.0 g, 31.0 mmol), synthesized in Preparation Example 21, 2-chloro-4,6-diphenylpyrimidine (8.3 g, 31.0 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (12.8 g, 92.9 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 156 (4-(3-(4,6-diphenylpyrimidine-2-yl)phenyl)-6-(naphth-2-yl)-2-phenylpyrimidine) (14.8 g, 25.1 mmol, yield 81%).

[0423] Mass spectrometry: [(M+H)] + ]:590

[0424] [Synthetic Example 16]: Synthesis of Compound 281

[0425]

[0426] Compound P1-11 (15.0 g, 29.4 mmol), synthesized in Preparation Example 27, 4-chloro-2,6-diphenylpyrimidine (7.8 g, 29.4 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.2 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 281 (4-([1,1'-biphenyl]-4-yl)-6-(2-(2,6-diphenylpyrimidine-4-yl)phenyl)-2-phenylpyrimidine) (14.8 g, 24.1 mmol, yield 82%).

[0427] Mass spectrometry: [(M+H)] + ]:616

[0428] [Synthetic Example 17]: Synthesis of Compound 284

[0429]

[0430] Compound P1-12 (15.0 g, 26.8 mmol), synthesized in Preparation Example 28, 4-chloro-2,6-diphenylpyrimidine (7.1 g, 26.8 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.3 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 284 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidine-4-yl)naphth-1-yl)-2-phenylpyrimidine) (14.6 g, 21.9 mmol, yield 82%).

[0431] Mass spectrometry: [(M+H)] + ]:666

[0432] [Synthetic Example 18]: Synthesis of Compound 305

[0433]

[0434] Compound P1-13 (15.0 g, 25.6 mmol), synthesized in Preparation Example 29, 4-chloro-2,6-diphenylpyrimidine (6.8 g, 25.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.6 g, 76.7 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 305 (2,4-bis([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyrimidine) (14.8 g, 21.5 mmol, yield 84%).

[0435] Mass spectrometry: [(M+H)] + ]:692

[0436] [Synthetic Example 19]: Synthesis of Compound 312

[0437]

[0438] Compound P1-10 (15.0 g, 31.0 mmol), synthesized in Preparation Example 26, 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (10.6 g, 31.0 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (12.8 g, 92.9 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane. The extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 312 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2-(naphthyl-2-yl)-6-phenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidin (17.7 g, 26.6 mmol, yield 86%).

[0439] Mass spectrometry: [(M+H)] + ]:666

[0440] [Synthetic Example 20]: Synthesis of Compound 319

[0441]

[0442] Compound P1-14 (15.0 g, 25.6 mmol), synthesized in Preparation Example 30, 4-chloro-2,6-diphenylpyrimidine (6.8 g, 25.6 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.6 g, 76.7 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 319 (4,6-bis([1,1'-biphenyl]-4-yl)-2-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyrimidine) (15.2 g, 22.0 mmol, yield 86%).

[0443] Mass spectrometry: [(M+H)] + ]:692

[0444] [Synthetic Example 21]: Synthesis of Compound 326

[0445]

[0446] Compound P1-15 (15.0 g, 28.6 mmol), synthesized in Preparation Example 31, 4-chloro-2,6-diphenylpyrimidine (7.6 g, 28.6 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (11.9 g, 85.8 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 326 (4-(dibenzo[b,d]furan-3-yl)-6-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidine) (16.0 g, 25.5 mmol, yield 89%).

[0447] Mass spectrometry: [(M+H)] + ]:630

[0448] [Synthetic Example 22]: Synthesis of Compound 331

[0449]

[0450] Compound P1-16 (15.0 g, 25.0 mmol), synthesized in Preparation Example 32, 4-chloro-2,6-diphenylpyrimidine (6.7 g, 25.0 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.4 g, 75.1 mmol) were reacted with stirring under heating and reflux for 4 hours in the presence of a mixed solvent of 180 ml toluene, 30 ml EtOH, and 30 ml water. After the reaction was complete, the reaction product was extracted with dichloromethane, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to give compound 331 (9-(3-(6-(4-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidin-4-yl)phenyl)-9H-carbazole (15.7 g, 22.3 mmol, yield 89%).

[0451] Mass spectrometry: [(M+H)] + ]:705

[0452] [Examples and Comparative Examples] - 1

[0453] [Examples 1 to 22 and Comparative Examples 1 to 9]: Fabrication of Blue Organic Electroluminescent Devices

[0454] 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.

[0455] 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.

[0456] An organic electroluminescent device is fabricated by sequentially laminating a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode onto an ITO transparent electrode (anode) of a substrate prepared as described above. Specifically, a hole injection layer is formed by co-depositing compounds A and B in a weight ratio of 98:2 to a thickness of 100 Å on the anode; a hole transport layer is formed by depositing compound A in a thickness of 1400 Å on the hole injection layer; a hole transport auxiliary layer is formed by depositing compound C in a thickness of 50 Å on the hole transport layer; a light-emitting layer is formed by co-depositing compounds D and E in a weight ratio of 98:2 to a thickness of 200 Å on the hole transport auxiliary layer; an electron transport auxiliary layer is formed by depositing compound F in a thickness of 50 Å on the light-emitting layer; an electron transport layer is formed by co-depositing the material for the electron transport layer and compound G in a weight ratio of 1:1 to a thickness of 300 Å on the electron transport auxiliary layer; an electron injection layer is formed by depositing LiF in a thickness of 10 Å on the electron transport layer; and a cathode is formed by depositing Al in a thickness of 1000 Å on the electron injection layer. The structures of compounds A to G are shown in Table 1 below, and the materials used for the electron transport layer are shown in Table 2 below.

[0457] [Table 1]

[0458]

[0459]

[0460] [Table 2]

[0461]

[0462]

[0463]

[0464]

[0465] [Experimental Example 1]: Evaluation of the performance of blue organic electroluminescent devices of Examples 1 to 22 and Comparative Examples 1 to 9

[0466] At 10 mA / cm 2 The driving voltage, EL peak value, and current efficiency of the organic electroluminescent devices fabricated in Examples 1 to 22 and Comparative Examples 1 to 9 were measured at a current density, and the results are shown in Table 3 below.

[0467] [Table 3]

[0468]

[0469]

[0470] As can be seen from Table 3, compared with the organic electroluminescent devices fabricated in Comparative Examples 1 to 9, the blue organic electroluminescent devices fabricated in Examples 1 to 22 exhibit superior driving voltage, EL peak value, and current efficiency.

[0471] Specifically, the blue organic electroluminescent devices of Examples 1 to 22 use a novel organic light-emitting compound according to the present disclosure as an electron transport layer material. This novel organic light-emitting compound has a structure in which an additional pyrimidine is connected to the 4-position of the pyrimidine via a phenylene or naphthylene group. It exhibits faster electron transport characteristics than compounds H to J having a single pyrimidine and compounds K to M in which two pyrimidines are connected via their respective 2-positions. It also exhibits a LUMO energy level that is more suitable as an electron transport layer material than compounds N to P in which two triazine groups are connected via a single phenylene or naphthylene group. Thus, due to the enhanced electron transfer capability to adjacent layers, it exhibits superior performance in terms of driving voltage, EL peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 9.

[0472] [Examples and Comparative Examples] - 2

[0473] [Examples 23 to 44 and Comparative Examples 10 to 18]: Fabrication of Blue Organic Electroluminescent Devices

[0474] 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.

[0475] 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.

[0476] An organic electroluminescent device is fabricated by sequentially laminating a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode onto an ITO transparent electrode (anode) of a substrate prepared as described above. Specifically, a hole injection layer is formed on the anode by co-depositing compounds A and B in a weight ratio of 98:2 to a thickness of 100 Å; a hole transport layer is formed on the hole injection layer by depositing compound A to a thickness of 1400 Å; a hole transport auxiliary layer is formed on the hole transport layer by depositing compound C to a thickness of 50 Å; a light-emitting layer is formed on the hole transport auxiliary layer by co-depositing compounds D and E in a weight ratio of 98:2 to a thickness of 200 Å; an electron transport auxiliary layer is formed on the light-emitting layer by depositing a material for an electron transport auxiliary layer to a thickness of 50 Å; an electron transport layer is formed on the electron transport auxiliary layer by co-depositing compounds Q and G in a weight ratio of 1:1 to a thickness of 300 Å; an electron injection layer is formed on the electron transport layer by depositing LiF to a thickness of 10 Å; and a cathode is formed on the electron injection layer by depositing Al to a thickness of 1000 Å. The structures of compounds A through E and compound G are shown in Table 1 above, the structure of compound Q is shown in Table 4 below, and the materials used for the electron transport auxiliary layer are shown in Table 5 below.

[0477] [Table 4]

[0478]

[0479] [Table 5]

[0480]

[0481]

[0482]

[0483] [Experimental Example 2]: Evaluation of the performance of the blue organic electroluminescent devices of Examples 23 to 44 and Comparative Examples 10 to 18

[0484] At 10 mA / cm 2 The driving voltage, EL peak value, and current efficiency of the organic electroluminescent devices fabricated in Examples 23 to 44 and Comparative Examples 10 to 18 were measured at a current density, and the results are shown in Table 6 below.

[0485] [Table 6]

[0486]

[0487] As can be seen from Table 6, compared with the organic electroluminescent devices prepared in Comparative Examples 10 to 18, the organic electroluminescent devices prepared in Examples 23 to 44 generally showed better results in the evaluation of driving voltage, EL peak value and current efficiency.

[0488] Specifically, the blue organic electroluminescent devices of Examples 23 to 44 use a novel organic light-emitting compound according to the present disclosure as an electron transport layer material. This novel organic light-emitting compound has a structure in which an additional pyrimidine is connected to the 4-position of the pyrimidine via a phenylene or naphthylene group. It exhibits faster electron transport characteristics than compounds H to J having a single pyrimidine and compounds K to M in which two pyrimidines are connected via their respective 2-positions. It also exhibits a shallower LUMO energy level than compounds N to P in which two triazine groups are connected via a single phenylene or naphthylene group. Thus, it exhibits superior electron transfer capability to the light-emitting layer. Therefore, compared with the blue organic electroluminescent devices of Comparative Examples 10 to 18, it exhibits superior performance in terms of driving voltage, EL peak, and current efficiency.

[0489] 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, X1 and X2 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N. Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 carbon atoms, a cycloalkyl group containing 3 to 60 carbon atoms, a heterocycloalkyl group containing 2 to 60 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 alkylphosphine oxide group containing 2 to 40 carbon atoms, or an arylphosphine oxide group containing 6 to 60 carbon atoms, wherein each of the above groups is unsubstituted or substituted, and L is an arylene containing 6 to 60 carbon atoms, each of which is unsubstituted or substituted.

2. The organic light-emitting compound according to claim 1, wherein... X1 and X2 are each independently either N or CH, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N. Ar1 to Ar4 are each independently an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, or an arylphosphine oxide group containing 6 to 30 carbon atoms. One is unsubstituted or substituted with an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group, and L is an arylene containing 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 30 carbon atoms, a heterocycloalkyl group containing 2 to 30 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 alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group.

3. The organic light-emitting compound according to claim 1, wherein... X1 and X2 are each independently either N or CH, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N. Ar1 to Ar4 are each independently composed of an aryl group containing 6 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, an alkylsilyl group containing 1 to 10 carbon atoms, an arylsilyl group containing 6 to 20 carbon atoms, an alkylphosphine oxide group containing 2 to 10 carbon atoms, or an arylphosphine oxide group containing 6 to 20 carbon atoms, wherein each of the above groups is unsubstituted or substituted with an alkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, an aryl group containing 6 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, an alkylsilyl group containing 1 to 10 carbon atoms, an arylsilyl group containing 6 to 20 carbon atoms, an alkylphosphine oxide group containing 2 to 20 carbon atoms, an arylphosphine oxide group containing 6 to 30 carbon atoms, a nitrile group, or a halogen group. L is an arylene containing 6 to 20 carbon atoms, each of which is unsubstituted or substituted with a nitrile group.

4. The organic light-emitting compound according to claim 1, wherein... X1 and X2 are each independently either N or CH, provided that one of X1 and X2 is N, and excluding the case where both X1 and X2 are N. Ar1 to Ar4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthrene, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoleyl, or triphenylphosphine oxide, each of which is unsubstituted or substituted with methyl, phenyl, pyridyl, carbazoleyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphine oxide, triphenylsilyl, nitrile, or fluorine, or each of which can form a fused ring structure. L is phenylene or naphthylene, each of which is unsubstituted or substituted with a nitrile group.

5. The organic light-emitting compound according to claim 1, wherein formula 1 is represented by formula 2 or formula 3: [Equation 2] [Formula 3] In equations 2 and 3, Ar1 to Ar4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthrene, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoleyl, or triphenylphosphine oxide, each of which is unsubstituted or substituted with methyl, phenyl, pyridyl, carbazoleyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphine oxide, triphenylsilyl, nitrile, or fluorine, or each of which can form a fused ring structure. L can be any one of the groups consisting of free formulas L-1 to L-15. [Equation L-1] [Equation L-2] [Equation L-3] [Equation L-4] [Equation L-5] [Equation L-6] [Formula L-7] [Formula L-8] [Formula L-9] [Formula L-10] [Formula L-11] [Formula L-12] [Equation L-13] [Equation L-14] [Formula L-15] In each of equations L-1 to L-15 * indicates the bonding site with Equation 1.

6. The organic light-emitting compound according to claim 1, wherein formula 1 is represented by formula 2 or formula 3: [Equation 2] [Formula 3] In equations 2 and 3, Ar1 through Ar4 are each independently phenyl, biphenyl, tolyl, naphthyl, fluorenyl, dibenzofuranyl, or carbazoleyl, and each of these groups is either unsubstituted or substituted with methyl, phenyl, or carbazoleyl. L can be any one of the groups consisting of free formulas L-1 to L-3 and L-5. [Equation L-1] [Equation L-2] [Formula L-3] [Formula L-5] In each of equations L-1 to L-3 and L-5, * indicates the bonding site with 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 001 to 336: 。 8. An organic electroluminescent device comprising the organic light-emitting compound according to claim 1.

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 or an electron transport auxiliary layer, and The organic light-emitting compound is contained in at least one layer of the electron transport layer or the electron transport auxiliary layer.

11. Use of the organic light-emitting compound according to claim 1 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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