Organic light-emitting compound and organic electroluminescent device comprising same

Abstract

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

Description

Organic luminescent compound and organic electroluminescent device containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2023-0166706, filed November 27, 2023, the entire contents of which are incorporated herein by reference.

[0003] Technology field

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

[0005]

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

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

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

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

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

[0011]

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

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

[0014] Prior art literature

[0015] Republic of Korea Patent Publication No. 10-2019-0131391

[0016]

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

[0018] In addition, the present invention aims to provide an organic luminescent compound having a LUMO energy level suitable for use as an organic layer material, specifically an electron transport layer material, of an organic electroluminescent device while exhibiting high electron mobility by expanding the LUMO (the lowest unoccupied molecular orbital) region.

[0019] In addition, the present invention aims to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel organic luminescent compound described above.

[0020] The problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

[0021]

[0022] In order to solve the above-described problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0023] [Chemical Formula 1]

[0024]

[0025] In the above chemical formula 1,

[0026] X1 and X2 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and one of X1 and X2 is N, except when both X1 and X2 are N,

[0027] Ar1 to Ar4 are each independently an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a heterocycloalkyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 2 to 40 carbon atoms, or an arylphosphine oxide group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0028] L is an arylene group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0029] In addition, the present invention provides an organic electroluminescent device comprising the organic luminescent compound.

[0030] In addition, the present invention provides the use of the organic light-emitting compound described above in an organic electroluminescent device.

[0031]

[0032] The organic light-emitting compound according to the present invention exhibits high electron mobility by forming the LUMO (the lowest unoccupied molecular orbital) region widely over the entire molecular region, and can have a LUMO energy level suitable for an electron transport layer material of an organic electroluminescent device.

[0033] In addition, an organic electroluminescent device including an organic light-emitting compound according to the present invention can have significantly improved luminous performance, driving voltage, lifespan, efficiency, etc., and can thus be more effectively applied to full-color display panels, etc.

[0034] The effects of the present invention are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

[0035]

[0036] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various different forms. These embodiments are provided solely to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the present invention, and the present invention is defined solely by the scope of the claims.

[0037] The terminology used herein is for the purpose of describing embodiments and is not intended to limit the present invention. In this specification, singular forms also include plural forms, unless specifically stated otherwise. As used herein, the terms "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0038] Unless otherwise defined, all terms (including technical and scientific terms) used herein may be used in their common sense to those skilled in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0039] Hereinafter, embodiments of the present invention will be described in detail.

[0040] Before proceeding, the meanings of terms used in this specification will be briefly explained. However, please note that the explanation of terms is intended to aid understanding of this specification and, unless explicitly stated to limit the invention, they are not intended to limit the technical spirit of the invention.

[0041] In the present invention, the term “aryl group” may mean a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may refer to, for example, a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a chrysenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, etc., but is not limited thereto. In addition, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon, which is a structure having one more substituent in addition to the "aryl group." The arylene group may refer to, for example, a phenylene group, a naphthylene group, an anthracenylene group, a biphenylene group, etc., but is not limited thereto.

[0042] In the present invention, the term "heteroaryl group" may mean a monovalent functional group derived from an aromatic heterocycle having a monocyclic or condensed ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of the heteroaryl group include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group, a tetrazolyl group, a benzotriazolyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a purinyl group, an indazolyl group, a quinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group, acridinyl group, phenanthridinyl group, carbazolyl group,Nitrogen-containing heteroaryl groups including a phenanthrolinyl group, a phenazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, etc.; Sulfur-containing heteroaryl groups including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples thereof include oxygen-containing heteroaryl groups, such as furyl group, pyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, and benzonaphthofuranyl group. In the above heteroaryl group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may refer to the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heteroaryl group may have a nuclear number of 5 to 60, 5 to 30, or 5 to 20.

[0043] In the present invention, the term “alkyl group” may mean a monovalent functional group derived from a saturated hydrocarbon having a linear or branched structure.The alkyl group may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1-ethylpropyl group, a 2-ethylpropyl group, an n-hexyl group, a 1-methyl-2-ethylpropyl group, a 1-ethyl-2-methylpropyl group, It may mean, but is not limited to, a 1,1,2-trimethylpropyl group, a 1-propylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a 2-methylpentyl group, and a 3-methylpentyl group.

[0044] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon having a ring structure. The cycloalkyl group may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclononyl group, and an adamantyl group, but is not limited thereto.

[0045] In the present invention, the term "heterocycloalkyl group" may mean a monovalent functional group derived from a saturated hydrocarbon having a ring structure, and the heteroaryl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. In the heterocycloalkyl group, the number of nuclear atoms may be defined instead of the number of carbon atoms. Here, the number of nuclear atoms may mean the number of atoms including, in addition to carbon (C) atoms, at least one heteroatom selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the heterocycloalkyl group may have 5 to 60, 5 to 30, or 5 to 20 nuclear atoms.

[0046] In the present invention, the terms "alkylsilyl group" and "arylsilyl group" may each mean a monovalent functional group derived from a compound in which at least one of the hydrogen atoms of a silane is substituted with the aforementioned alkyl group and aryl group. The arylsilyl group may be, for example, a triphenylsilyl group, but is not limited thereto.

[0047] In the present invention, the terms "alkylphosphine oxide group" and "arylphosphine oxide group" may each mean a monovalent functional group derived from a compound in which the aforementioned allyl group and aryl group are substituted on a phosphine oxide. The alkylphosphine oxide group may be, for example, a dimethylphosphine oxide group, and the arylphosphine oxide group may be, for example, a triphenylphosphine oxide group, and the like, but is not limited thereto.

[0048] In the present invention, the term "substitution" means substitution with one or more substituents each independently selected from the group consisting of deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heterocycloalkyl group having 5 to 30 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group, and a halogen group, and when substitution is performed with multiple substituents, they may be the same as or different from each other.

[0049]

[0050] Organic luminescent compounds

[0051] The present invention provides a novel organic luminescent compound. The organic luminescent compound is represented by the following chemical formula 1.

[0052] [Chemical Formula 1]

[0053]

[0054] In the above chemical formula 1,

[0055] X1 and X2 are each independently N or CR, wherein R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and one of X1 and X2 is N, except when both X1 and X2 are N,

[0056] Ar1 to Ar4 are each independently an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a heterocycloalkyl group having 2 to 60 carbon atoms, a heterocycloalkyl group having 5 to 60 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 2 to 40 carbon atoms, or an arylphosphine oxide group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0057] L is an arylene group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted.

[0058] Specifically, one or more groups of the hydrogen atoms, alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylsilyl groups, alkylphosphine oxide groups and arylphosphine oxide groups that can be present in the above Ar1 to Ar4, L are each independently unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heterocycloalkyl group having 5 to 30 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a arylsilyl group having 2 to 20 carbon atoms, It means being substituted with one or more substituents selected from the group consisting of an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group, and a halogen group, and when substituted with multiple substituents, they may be the same or different from each other.

[0059] In one embodiment, in the chemical formula 1,

[0060] X1 and X2 are each independently N or CH, wherein one of said X1 and X2 is N, except when both of said X1 and X2 are N,

[0061] Ar1 to Ar4 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heterocycloalkyl group having 5 to 30 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, or an arylphosphine oxide group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heterocycloalkyl group having 5 to 30 nuclear atoms, an aryl group having 6 to 30 carbon atoms, It may be substituted with a heterocycloalkyl group of 30 carbon atoms, an aryl group of 6 to 30 carbon atoms, a heteroaryl group of 2 to 30 carbon atoms, a heteroaryl group of 5 to 30 nuclear atoms, an alkylsilyl group of 1 to 20 carbon atoms, an arylsilyl group of 6 to 30 carbon atoms, an alkylphosphine oxide group of 2 to 20 carbon atoms, an arylphosphine oxide group of 6 to 30 carbon atoms, a nitrile group or a halogen group,

[0062] L is an arylene group having 6 to 30 carbon atoms, each of which may be unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heterocycloalkyl group having 5 to 30 nuclear atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group, or a halogen group.

[0063] In one embodiment, in the chemical formula 1,

[0064] X1 and X2 are each independently N or CH, wherein one of said X1 and X2 is N, except when both of said X1 and X2 are N,

[0065] Ar1 to Ar4 are each independently an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 5 to 20 nuclear atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 2 to 10 carbon atoms, or an arylphosphine oxide group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 nuclear atoms, a heteroaryl group having 5 to 20 nuclear atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, It may be substituted with an alkylphosphine oxide group, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group, or a halogen group,

[0066] L is an arylene group having 6 to 20 carbon atoms, each of which may be unsubstituted or substituted with a nitrile group.

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

[0068] X1 and X2 are each independently N or CH, and only one of X1 and X2 is N,

[0069] Ar1 to Ar4 are each independently a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group or a triphenylphosphine oxide group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a bicyclononyl group, an adamantyl group, a cyclohexyl group, a dimethylphosphine oxide group, a triphenylsilyl group, a nitrile group or a fluorine group, or each of these rings may form a condensed ring structure.

[0070] L is a phenylene group or a naphthylene group, each of which may be unsubstituted or substituted with a nitrile group.

[0071] In one embodiment, the above chemical formula 1 can be represented by the following chemical formula 2 or chemical formula 3.

[0072] [Chemical Formula 2]

[0073]

[0074] [Chemical Formula 3]

[0075]

[0076] In each of the above chemical formulas 2 and 3,

[0077] Ar1 to Ar4 are each independently a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group or a triphenylphosphine oxide group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a bicyclononyl group, an adamantyl group, a cyclohexyl group, a dimethylphosphine oxide group, a triphenylsilyl group, a nitrile group or a fluorine group, or each of these rings may form a condensed ring structure.

[0078] L is any one of the following chemical formulas L-1 to L-15,

[0079] [Chemical Formula L-1] [Chemical Formula L-2]

[0080]

[0081] [Chemical Formula L-3] [Chemical Formula L-4]

[0082]

[0083] [Chemical Formula L-5] [Chemical Formula L-6]

[0084]

[0085] [Chemical Formula L-7] [Chemical Formula L-8]

[0086]

[0087] [Chemical Formula L-9] [Chemical Formula L-10]

[0088]

[0089] [Chemical Formula L-11] [Chemical Formula L-12]

[0090]

[0091] [Chemical Formula L-13] [Chemical Formula L-14]

[0092]

[0093] [Chemical Formula L-15]

[0094]

[0095] In each of the above chemical formulas L-1 to L-15, * represents a site bonded to the above chemical formula 1.

[0096] In one embodiment, in each of the chemical formula 2 or chemical formula 3,

[0097] Ar1 to Ar4 are each independently a phenyl group, a biphenyl group, a tolyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group or a carbazolyl group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group or a carbazolyl group,

[0098] L is any one of the following chemical formulas L-1 to L-3 and L-5,

[0099] [Chemical Formula L-1] [Chemical Formula L-2]

[0100]

[0101] [Chemical Formula L-3] [Chemical Formula L-5]

[0102]

[0103] In each of the above chemical formulas L-1 to L-3 and L-5, * represents a site bonded to the above chemical formula 1.

[0104] In one embodiment, the organic light-emitting compound represented by the above chemical formula 1 may be any one of the following compounds 001 to 336.

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] As a specific example, the compound represented by the above chemical formula 1 may be any one or more of the above compounds 004, 009, 015, 019, 044, 060, 067, 075, 082, 100, 116, 121, 127, 131, 156, 281, 284, 305, 312, 319, 326, and 331.

[0190] The novel organic light-emitting compound of the present invention has a structure in which an additional pyrimidine is connected to a phenylene or naphthylene at the 4th position of the pyrimidine, thereby exhibiting fast electron transfer characteristics and exhibiting a LUMO energy level suitable for an electron transport layer material, thereby enabling excellent electron transfer capability to an adjacent layer.

[0191] In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, luminescence peak, and current efficiency can be achieved.

[0192]

[0193] Organic electroluminescent devices

[0194] The present invention provides an organic electroluminescent device comprising the novel organic luminescent compound described above. The organic luminescent compound according to the present invention may be included in at least one of the organic layers disposed between the cathode and the anode of the organic electroluminescent device.

[0195] In one embodiment, the organic electroluminescent device comprises an anode; a cathode; a light-emitting layer disposed between the cathode and the anode; and an electron transport region disposed between the cathode and the light-emitting layer, wherein the electron transport region comprises an organic light-emitting compound according to the present invention.

[0196] anode

[0197] The organic electroluminescent device of the present invention includes an anode. The anode serves to inject holes into an organic layer. Here, the organic layer may refer to one or more layers formed between the anode and the cathode.

[0198] The type of the above-mentioned positive electrode material is not particularly limited and can be manufactured according to a conventional method known in the art. The above-mentioned positive electrode material may be, for example, a metal such as vanadium, chromium, copper, zinc and gold or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); a complex of a metal and an oxide such as ZnO:Al and SnO2:Sb; a conductive polymer such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole and polyaniline; and carbon black, etc., and each of these may be used alone or two or more types may be used in combination.

[0199] The method for manufacturing the above anode is not particularly limited, and can be manufactured according to conventional methods known in the art. For example, the anode can be formed by coating an anode material on a substrate such as a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film.

[0200] cathode

[0201] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into the organic layer.

[0202] The type of cathode material forming the above cathode is not particularly limited and can be manufactured according to a conventional method known in the art. The cathode material may be, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0203] luminescent layer

[0204] The organic electroluminescent device of the present invention includes a light-emitting layer disposed between the cathode and the anode. The light-emitting layer is a layer in which holes and electrons meet to form excitons, and the color of light emitted by the organic electroluminescent device may vary depending on the material forming the light-emitting layer.

[0205] The light-emitting material forming the above light-emitting layer can be any of a variety of commercially available materials without any particular limitation, depending on the wavelength of the desired emitted light.

[0206] In one embodiment, the light-emitting material can be classified into blue, green, red light-emitting materials, etc. according to the light-emitting color, and the light-emitting material can form a light-emitting layer by mixing a host material and a dopant material to prevent problems such as a decrease in color purity or a decrease in the efficiency of the device due to a light-emitting attenuation effect. The light-emitting efficiency of the light-emitting device can be improved by using the host material, which is the main material forming the light-emitting layer, and a small amount of dopant having a smaller energy band gap than the host material.

[0207] electron transport region

[0208] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0209] The electron transport region serves to transport electrons injected from the cathode to the light-emitting layer. This electron transport region may include at least one selected from the group consisting of an electron injection layer and an electron transport layer. In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include both the electron transport layer and the electron injection layer described above.

[0210] In the electron transport region, the electron injection layer can use an electron injection material that is easy to inject electrons from the cathode and has high electron mobility without limitation. Non-limiting examples of usable electron injection materials include the above-described bipolar compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As a specific example, the electron injection material may include at least one selected from the group consisting of LiF, Li2O, BaO, NaCl, CsF; lanthanide metals such as Yb; and halogenated metals such as RbCl, RbI.

[0211] The above electron transport layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention has a structure in which an additional pyrimidine is connected to a phenylene or naphthylene at position 4 of a pyrimidine, thereby exhibiting fast electron transfer characteristics and exhibiting a LUMO energy level suitable for an electron transport layer material, thereby enabling excellent electron transfer capability to an adjacent layer. By using the novel organic light-emitting compound according to the present invention as an electron transport layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0212] The above electron transport layer can be formed by mixing the organic light-emitting compound according to the present invention and Liq (lithium quinolate). Liq has a conduction band of 5.58 eV and a valence band of 3.153 eV, thereby having the effect of lowering the potential barrier.

[0213] The electron transport region can be manufactured using conventional methods known in the art. Examples of the electron transport region include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0214] electron transport auxiliary layer

[0215] The organic electroluminescent device of the present invention may include an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region. The electron transport auxiliary layer can prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport region.

[0216] The above electron transport auxiliary layer may include the organic light-emitting compound according to the present invention described above. The organic light-emitting compound according to the present invention has a structure in which an additional pyrimidine is connected to the 4th position of the pyrimidine with one phenylene or naphthylene, thereby exhibiting fast electron transfer characteristics and exhibiting a LUMO energy level suitable for an electron transport layer material, thereby enabling excellent electron transfer capability to an adjacent layer. By using the novel organic light-emitting compound according to the present invention as an electron transport auxiliary layer material, excellent performance in terms of driving voltage, emission peak, and current efficiency can be realized.

[0217] The above electron transport auxiliary layer may be formed by, but is not limited to, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett method, an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, etc., as is known in the art.

[0218] hole transport region

[0219] The organic electroluminescent device of the present invention may further include a hole transport region disposed between the anode and the light-emitting layer. The hole transport region serves to move holes injected from the anode to the light-emitting layer.

[0220] The above-mentioned hole transport region may include at least one of a hole injection layer and a hole transport layer. In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include both the hole injection layer and the hole transport layer described above.

[0221] The materials forming the hole injection layer and the hole transport layer are not particularly limited as long as they have a low hole injection barrier and high hole mobility, and any hole injection material and hole transport material used in the art can be used without limitation. The materials forming the hole injection layer and the hole transport layer may be the same or different from each other.

[0222] The hole-injecting material may be any hole-injecting material known in the art without limitation. Non-limiting examples of usable hole-injecting materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,Ndiphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), etc. Can be used alone or in combination of two or more

[0223] In addition, the hole transport material may be any hole transport material known in the art without limitation. Non-limiting examples of hole transport materials that can be used include carbazole derivatives such as phenylcarbazole and polyvinylcarbazole; fluorene derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(Ncarbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), etc., and these may be used alone or in combination of two or more.

[0224] The above hole transport region can be manufactured by a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0225] hole transport auxiliary layer

[0226] The organic electroluminescent device of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region and the light-emitting layer. The light-emitting auxiliary layer serves to transport holes moving from the hole transport region to the light-emitting layer, while also serving to control the thickness of the organic layer. The light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer, and has a high triplet (T1) energy to prevent excitons in the light-emitting layer from diffusing to the hole transport layer.

[0227] These light-emitting auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the light-emitting auxiliary layers of the red, green, and blue organic light-emitting devices may be made of the same material.

[0228] The above-mentioned light-emitting auxiliary layer material is not particularly limited, and for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives can be used. In addition, the light-emitting auxiliary layer may optionally include a p-type dopant in addition to the above-mentioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field can be used.

[0229] capping layer

[0230] The organic electroluminescent device of the present invention may further include a capping layer disposed on the cathode. The capping layer serves to protect the organic light-emitting device while helping light generated from the organic layer to be efficiently emitted to the outside.

[0231] The capping material forming the capping layer may include, but is not limited to, at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4'-bis[N-(1-naphthyl)-N-phenyl-amino] biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 1,1'-bis(di-4-tolylaminophenyl) cyclohexane (TAPC).

[0232] The capping layer may be a single layer, but may include two or more layers having different refractive indices, so that the refractive index gradually changes as it passes through the two or more layers.

[0233] The above capping layer can be manufactured by a conventional method known in the art, and various methods such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett) method can be used, for example.

[0234]

[0235] The present invention provides a use of the organic light-emitting compound described above in an organic electroluminescent device. This provides an organic electroluminescent device with significantly improved luminescence performance, driving voltage, lifespan, and efficiency.

[0236] In one embodiment, the use of the organic light-emitting compound may be as an electron transport material in the organic electroluminescent device.

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

[0238] In one embodiment, the organic light-emitting compound can be used as a material of an electron transport layer and / or an electron transport auxiliary layer in the organic electroluminescent device.

[0239]

[0240] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0241]

[0242] [Preparation]

[0243] [Preparation Example 1]: Synthesis of P2-1

[0244]

[0245] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain compound P2-1 (4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine) (33.4 g, 79.7 mmol, yield 80%).

[0246] Mass: [(M+H) + ] : 420

[0247]

[0248] [Example 2]: Synthesis of P2-2

[0249]

[0250] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-2(4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine)(40.4 g, 81.7 mmol, yield 82%).

[0251] Mass: [(M+H) + ] : 496

[0252]

[0253] [Example 3]: Synthesis of P2-3

[0254]

[0255] 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (9-phenyl-9H-carbazol-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-3 (2-(6-(3-chlorophenyl)-2-phenylpyrimidin-4-yl)-9-phenyl-9H-carbazole) (38.5 g, 75.7 mmol, yield 76%).

[0256] Mass: [(M+H) + ] : 509

[0257]

[0258] [Example 4]: Synthesis of P2-4

[0259]

[0260] 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid (287.13 g, 99.6 mmol), Pd(PPh3)4 (3.5 g, 3.0 mmol), K2CO3 (41.3 g, 298.8 mmol) were added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-4(9-(3-(6-(3-chlorophenyl)-2-phenylpyrimidin-4-yl)phenyl)-9H-carbazole)(43.0 g, 84.7 mmol, yield 85%).

[0261] Mass: [(M+H) + ] : 509

[0262]

[0263] [Example 5]: Synthesis of P2-5

[0264]

[0265] 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine(30.0 g, 99.6 mmol), naphthalen-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried over magnesium sulfide, concentrated, and purified by column chromatography to obtain compound P2-5(4-(3-chlorophenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine)(32.5 g, 88.7 mmol, yield 89%).

[0266] Mass: [(M+H) + ] : 368

[0267]

[0268] [Example 6]: Synthesis of P2-6

[0269]

[0270] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-6 (2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine) (31.3 g, 74.7 mmol, yield 75%).

[0271] Mass: [(M+H) + ] : 420

[0272]

[0273] [Example 7]: Synthesis of P2-7

[0274]

[0275] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-7 (4-(3-chlorophenyl)-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine) (36.2 g, 83.7 mmol, yield 84%).

[0276] Mass: [(M+H) + ] : 434

[0277]

[0278] [Example 8]: Synthesis of P2-8

[0279]

[0280] 2-chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazol-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-8(9-(3-(4-(3-chlorophenyl)-6-phenylpyrimidin-2-yl)phenyl)-9H-carbazole)(42.0 g, 82.7 mmol, yield 83%).

[0281] Mass: [(M+H) + ] : 509

[0282]

[0283] [Example 9]: Synthesis of P2-9

[0284]

[0285] 2-chloro-4-(3-chlorophenyl)-6-phenylpyrimidine (30.0 g, 99.6 mmol), (9,9-dimethyl-9H-fluoren-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-9 (4-(3-chlorophenyl)-2-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyrimidine) (37.5 g, 81.7 mmol, yield 82%).

[0286] Mass: [(M+H) + ] : 460

[0287]

[0288] [Example 10]: Synthesis of P2-10

[0289]

[0290] 2-Chloro-4-(3-chlorophenyl)-6-phenylpyrimidine(30.0 g, 99.6 mmol), naphthalen-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried over magnesium sulfide, concentrated, and purified by column chromatography to obtain compound P2-10(4-(3-chlorophenyl)-2-(naphthalen-2-yl)-6-phenylpyrimidine)(32.1 g, 81.7 mmol, yield 82%).

[0291] Mass: [(M+H) + ] : 394

[0292]

[0293] [Example 11]: Synthesis of P2-11

[0294]

[0295] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-11 (4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine) (33.4 g, 79.7 mmol, yield 80%).

[0296] Mass: [(M+H) + ] : 420

[0297]

[0298] [Example 12]: Synthesis of P2-12

[0299]

[0300] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (30.0 g, 87.5 mmol), (3-chloronaphthalen-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-12 (4-([1,1'-biphenyl]-4-yl)-6-(3-chloronaphthalen-1-yl)-2-phenylpyrimidine) (32.8 g, 70.0 mmol, yield 80%).

[0301] Mass: [(M+H) + ] : 470

[0302]

[0303] [Example 13]: Synthesis of P2-13

[0304]

[0305] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-13 (2,4-di([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)pyrimidine) (45.8 g, 92.5 mmol, yield 80%).

[0306] Mass: [(M+H) + ] : 496

[0307]

[0308] [Example 14]: Synthesis of P2-14

[0309]

[0310] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-14 (4,6-di([1,1'-biphenyl]-4-yl)-2-(3-chlorophenyl)pyrimidine) (45.2 g, 91.3 mmol, yield 79%).

[0311] Mass: [(M+H) + ] : 496

[0312]

[0313] [Example 15]: Synthesis of P2-15

[0314]

[0315] 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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-15 (4-(2-chlorophenyl)-6-(dibenzo[b,d]furan-3-yl)-2-phenylpyrimidine) (30.7 g, 83.7 mmol, yield 84%).

[0316] Mass: [(M+H) + ] : 368

[0317]

[0318] [Example 16]: Synthesis of P2-16

[0319]

[0320] 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine (30.0 g, 99.6 mmol), (3-(9H-carbazol-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 added to a mixed solvent of 360 ml of toluene, 60 ml of EtOH, and 60 ml of water, and reacted while heating and stirring under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound P2-16 (9-(3-(6-(4-chlorophenyl)-2-phenylpyrimidin-4-yl)phenyl)-9H-carbazole) (43.0 g, 84.7 mmol, yield 85%).

[0321] Mass: [(M+H) + ] : 509

[0322]

[0323] [Example 17]: Synthesis of P1-1

[0324]

[0325] Compound P2-1 (30 g, 71.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 1 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 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%).

[0326] Mass: [(M+H) + ] : 511

[0327]

[0328] [Example 18]: Synthesis of P1-2

[0329]

[0330] Compound P2-2 (30 g, 60.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 2 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-2(4-([1,1':3',1''-terphenyl]-5'-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(30.2 g, 51.5 mmol, yield 85%).

[0331] Mass: [(M+H) + ] : 588

[0332]

[0333] [Example 19]: Synthesis of P1-3

[0334]

[0335] Compound P2-3 (30 g, 59.1 mmol), bis(pinacolato) 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 by the method of Preparation Example 3 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-3(9-phenyl-2-(2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-4-yl)-9H-carbazole)(30.1 g, 50.2 mmol, yield 85%).

[0336] Mass: [(M+H) + ] : 601

[0337]

[0338] [Example 20]: Synthesis of P1-4

[0339]

[0340] Compound P2-4 (30 g, 59.1 mmol), bis(pinacolato) 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 by the method of Preparation Example 4 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-4(9-(3-(2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-4-yl)phenyl)-9H-carbazole)(31.9 g, 53.1 mmol, yield 90%).

[0341] Mass: [(M+H) + ] : 601

[0342]

[0343] [Example 21]: Synthesis of P1-5

[0344]

[0345] Compound P2-5 (30 g, 76.4 mmol), bis(pinacolato) 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) synthesized by the method of Preparation Example 5 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-5(4-(naphthalen-2-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(31.8 g, 65.7 mmol, yield 86%).

[0346] Mass: [(M+H) + ] : 485

[0347]

[0348] [Example 22]: Synthesis of P1-6

[0349]

[0350] Compound P2-6 (30 g, 71.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 6 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-6 (2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine) (32.2 g, 63.0 mmol, yield 88%).

[0351] Mass: [(M+H) + ] : 511

[0352]

[0353] [Example 23]: Synthesis of P1-7

[0354]

[0355] Compound P2-7 (30 g, 69.3 mmol), bis(pinacolato) 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 by the method of Preparation Example 7 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-7 (2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(31.3 g, 59.6 mmol, yield 86%).

[0356] Mass: [(M+H) + ] : 525

[0357]

[0358] [Example 24]: Synthesis of P1-8

[0359]

[0360] Compound P2-8 (30 g, 59.1 mmol), bis(pinacolato) 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 by the method of Preparation Example 8 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-8(9-(3-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-yl)phenyl)-9H-carbazole)(31.2 g, 52.0 mmol, yield 88%).

[0361] Mass: [(M+H) + ] : 601

[0362]

[0363] [Example 25]: Synthesis of P1-9

[0364]

[0365] Compound P2-9 (30 g, 65.4 mmol), bis(pinacolato) 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) synthesized by the method of Preparation Example 9 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-9 (2-(9,9-dimethyl-9H-fluoren-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine) (32.0 g, 58.2 mmol, yield 89%).

[0366] Mass: [(M+H) + ] : 552

[0367]

[0368] [Example 26]: Synthesis of P1-10

[0369]

[0370] Compound P2-10 (30 g, 76.4 mmol), bis(pinacolato) 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) synthesized by the method of Preparation Example 10 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-10 (2-(naphthalen-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine) (29.2 g, 60.3 mmol, yield 79%).

[0371] Mass: [(M+H) + ] : 485

[0372]

[0373] [Example 27]: Synthesis of P1-11

[0374]

[0375] Compound P2-11 (30 g, 71.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 11 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-11 (4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(30.7 g, 60.2 mmol, yield 84%).

[0376] Mass: [(M+H) + ] : 511

[0377]

[0378] [Example 28]: Synthesis of P1-12

[0379]

[0380] Compound P2-12 (30 g, 64.0 mmol), bis(pinacolato) 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 by the method of Preparation Example 12 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-12 (4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)pyrimidine) (29.8 g, 53.1 mmol, yield 83%).

[0381] Mass: [(M+H) + ] : 562

[0382]

[0383] [Example 29]: Synthesis of P1-13

[0384]

[0385] Compound P2-13 (30 g, 60.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 13 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-13 (2,4-di([1,1'-biphenyl]-4-yl)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(29.5 g, 50.3 mmol, yield 83%).

[0386] Mass: [(M+H) + ] : 588

[0387]

[0388] [Example 30]: Synthesis of P1-14

[0389]

[0390] Compound P2-14 (30 g, 60.6 mmol), bis(pinacolato) 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 by the method of Preparation Example 14 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-14 (4,6-di([1,1'-biphenyl]-4-yl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(29.9 g, 50.9 mmol, yield 84%).

[0391] Mass: [(M+H) + ] : 588

[0392]

[0393] [Example 31]: Synthesis of P1-15

[0394]

[0395] Compound P2-15 (30 g, 69.3 mmol), bis(pinacolato) 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 by the method of Preparation Example 15 were added to 300 ml of 1,4-Dioxane and reacted while stirring and heating under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-15 (4-(dibenzo[b,d]furan-3-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine)(30.9 g, 58.9 mmol, yield 85%).

[0396] Mass: [(M+H) + ] : 525

[0397]

[0398] [Example 32]: Synthesis of P1-16

[0399]

[0400] Compound P2-16 (30 g, 59.1 mmol), bis(pinacolato) 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 by the method of Preparation Example 16 were added to 300 ml of 1,4-Dioxane and reacted while heating and stirring under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain compound P1-16(9-(3-(2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-4-yl)phenyl)-9H-carbazole)(28.7 g, 47.8 mmol, yield 81%).

[0401] Mass: [(M+H) + ] : 601

[0402]

[0403] [Synthesis example]

[0404] [Synthesis Example 1]: Synthesis of Compound 004

[0405]

[0406] Compound P1-1 (15.0 g, 29.4 mmol), 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) synthesized by the method of Preparation Example 17 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 004 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidine) (15.4 g, 25.0 mmol, yield 85%).

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

[0408]

[0409] [Synthesis Example 2]: Synthesis of Compound 009

[0410]

[0411] 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 by the method of Preparation Example 18 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 009 (4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidine)(14.8 g, 21.5 mmol, yield 84%).

[0412] Mass: [(M+H) + ] : 692

[0413]

[0414] [Synthesis Example 3]: Synthesis of Compound 015

[0415]

[0416] Compound P1-3 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 19 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 015 (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%).

[0417] Mass: [(M+H) + ] : 705

[0418]

[0419] [Synthesis Example 4]: Synthesis of Compound 019

[0420]

[0421] Compound P1-4 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 20 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 019 (9-(3-(6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidin-4-yl)phenyl)-9H-carbazole) (14.8 g, 21.0 mmol, yield 84%).

[0422] Mass: [(M+H) + ] : 705

[0423]

[0424] [Synthesis Example 5]: Synthesis of Compound 044

[0425]

[0426] Compound P1-5 (15.0 g, 31.0 mmol), 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) synthesized by the method of Preparation Example 21 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 044 (4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine) (15.3 g, 26.0 mmol, yield 84%).

[0427] Mass: [(M+H) + ] : 590

[0428]

[0429] [Synthesis Example 6]: Synthesis of Compound 060

[0430]

[0431] Compound P1-6 (15.0 g, 29.4 mmol), 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) synthesized by the method of Preparation Example 22 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 060 (2-([1,1'-biphenyl]-4-yl)-4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-phenylpyrimidine) (16.1 g, 26.2 mmol, yield 89%).

[0432] Mass: [(M+H) + ] : 616

[0433]

[0434] [Synthesis Example 7]: Synthesis of Compound 067

[0435]

[0436] Compound P1-7 (15.0 g, 28.6 mmol), 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) synthesized by the method of Preparation Example 23 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0437] Mass: [(M+H) + ] : 630

[0438]

[0439] [Synthesis Example 8]: Synthesis of Compound 075

[0440]

[0441] Compound P1-8 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 24 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0442] Mass: [(M+H) + ] : 705

[0443]

[0444] [Synthesis Example 9]: Synthesis of Compound 082

[0445]

[0446] Compound P1-9 (15.0 g, 27.2 mmol), 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) synthesized by the method of Preparation Example 25 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 082 (2-(9,9-dimethyl-9H-fluoren-2-yl)-4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-6-phenylpyrimidine) (15.5 g, 23.7 mmol, yield 87%).

[0447] Mass: [(M+H) + ] : 656

[0448]

[0449] [Synthesis Example 10]: Synthesis of Compound 100

[0450]

[0451] Compound P1-10 (15.0 g, 31.0 mmol), 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) synthesized by the method of Preparation Example 26 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 100 (4-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-(naphthalen-2-yl)-6-phenylpyrimidine) (15.5 g, 26.3 mmol, yield 85%).

[0452] Mass: [(M+H) + ] : 590

[0453]

[0454] [Synthesis Example 11]: Synthesis of Compound 116

[0455]

[0456] Compound P1-1 (15.0 g, 29.4 mmol), 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) synthesized by the method of Preparation Example 17 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 116 (4-([1,1'-biphenyl]-4-yl)-6-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-2-phenylpyrimidine) (15.2 g, 24.7 mmol, yield 84%).

[0457] Mass: [(M+H) + ] : 616

[0458]

[0459] [Synthesis Example 12]: Synthesis of Compound 121

[0460]

[0461] Compound P1-2 (15.0 g, 25.6 mmol), 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) synthesized by the method of Preparation Example 18 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 121 (4-([1,1':3',1''-terphenyl]-5'-yl)-6-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-2-phenylpyrimidine)(14.1 g, 20.5 mmol, yield 80%).

[0462] Mass: [(M+H) + ] : 692

[0463]

[0464] [Synthesis Example 13]: Synthesis of Compound 127

[0465]

[0466] Compound P1-3 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 19 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0467] Mass: [(M+H) + ] : 705

[0468]

[0469] [Synthesis Example 14]: Synthesis of Compound 131

[0470]

[0471] Compound P1-4 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 20 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0472] Mass: [(M+H) + ] : 705

[0473]

[0474] [Synthesis Example 15]: Synthesis of Compound 156

[0475]

[0476] Compound P1-5 (15.0 g, 31.0 mmol), 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) synthesized by the method of Preparation Example 21 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 156 (4-(3-(4,6-diphenylpyrimidin-2-yl)phenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine) (14.8 g, 25.1 mmol, yield 81%).

[0477] Mass: [(M+H) + ] : 590

[0478]

[0479] [Synthesis Example 16]: Synthesis of Compound 281

[0480]

[0481] Compound P1-11 (15.0 g, 29.4 mmol), 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) synthesized by the method of Preparation Example 27 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 281 (4-([1,1'-biphenyl]-4-yl)-6-(2-(2,6-diphenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidine) (14.8 g, 24.1 mmol, yield 82%).

[0482] Mass: [(M+H) + ] : 616

[0483]

[0484] [Synthesis Example 17]: Synthesis of Compound 284

[0485]

[0486] Compound P1-12 (15.0 g, 26.8 mmol), 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) synthesized by the method of Preparation Example 28 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 284 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidin-4-yl)naphthalen-1-yl)-2-phenylpyrimidine) (14.6 g, 21.9 mmol, yield 82%).

[0487] Mass: [(M+H) + ] : 666

[0488]

[0489] [Synthesis Example 18]: Synthesis of Compound 305

[0490]

[0491] Compound P1-13 (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 by the method of Preparation Example 29 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 305 (2,4-di([1,1'-biphenyl]-4-yl)-6-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyrimidine)(14.8 g, 21.5 mmol, yield 84%).

[0492] Mass: [(M+H) + ] : 692

[0493]

[0494] [Synthesis Example 19]: Synthesis of Compound 312

[0495]

[0496] Compound P1-10 (15.0 g, 31.0 mmol), 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) synthesized by the method of Preparation Example 26 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 312 (4-([1,1'-biphenyl]-4-yl)-6-(3-(2-(naphthalen-2-yl)-6-phenylpyrimidin-4-yl)phenyl)-2-phenylpyrimidine)(17.7 g, 26.6 mmol, yield 86%).

[0497] Mass: [(M+H) + ] : 666

[0498]

[0499] [Synthesis Example 20]: Synthesis of Compound 319

[0500]

[0501] Compound P1-14 (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 by the method of Preparation Example 30 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain compound 319 (4,6-di([1,1'-biphenyl]-4-yl)-2-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)pyrimidine)(15.2 g, 22.0 mmol, yield 86%).

[0502] Mass: [(M+H) + ] : 692

[0503]

[0504] [Synthesis Example 21]: Synthesis of Compound 326

[0505]

[0506] Compound P1-15 (15.0 g, 28.6 mmol), 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) synthesized by the method of Preparation Example 31 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0507] Mass: [(M+H) + ] : 630

[0508]

[0509] [Synthesis Example 22]: Synthesis of Compound 331

[0510]

[0511] Compound P1-16 (15.0 g, 25.0 mmol), 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) synthesized by the method of Preparation Example 32 were added to a mixed solvent of 180 ml of toluene, 30 ml of EtOH, and 30 ml of water, and reacted while heating and stirring under reflux for 4 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was concentrated after removing moisture with magnesium sulfide, and purified by column chromatography to obtain 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%).

[0512] Mass: [(M+H) + ] : 705

[0513]

[0514] [Examples and Comparative Examples] - 1

[0515] [Examples 1 to 22 and Comparative Examples 1 to 9]: Fabrication of blue organic electroluminescent devices

[0516] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0517] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0518] An organic electroluminescent device was manufactured by sequentially stacking 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 on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing Compound A and Compound B in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing Compound D and Compound E in a weight ratio of 98:2 on the hole transport auxiliary layer to a thickness of 200 Å, the electron transport auxiliary layer was formed by depositing Compound F in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing an electron transport layer material and Compound G in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. Here, the structures of the compounds A to G are shown in Table 1 below, and the electron transport layer materials are as shown in Table 2 below.

[0519] Compound A Compound B Compound C Compound D Compound E Compound F Compound G

[0520] Electron transport layer material Example 1 Compound 004 Example 2 Compound 009 Example 3 Compound 015 Example 4 Compound 019 Example 5 Compound 044 Example 6 Compound 060 Example 7 Compound 067 Example 8 Compound 075 Example 9 Compound 082 Example 10 Compound 100 Example 11 Compound 116 Example 12 Compound 121 Example 13 Compound 127 Example 14 Compound 131 Example 15 Compound 156 Example 16 Compound 281 Example 17 Compound 284 Example 18 Compound 305 Example 19 Compound 312 Example 20 Compound 319 Example 21 Compound 326 Example 22 Compound 331 Comparative Example 1 Compound H Comparative Example 2 Compound I Comparative Example 3 Compound J Comparative Example 4 Compound K Comparative Example 5 Compound L Comparative Example 6 Compound M Comparative Example 7 Compound N Comparative Example 8 Compound O Comparative Example 9 Compound P

[0521]

[0522] [Experimental Example 1]: Performance evaluation of blue organic electroluminescent devices of Examples 1 to 22 and Comparative Examples 1 to 9

[0523] For the organic electroluminescent devices manufactured in Examples 1 to 22 and Comparative Examples 1 to 9, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 3 below.

[0524] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 13.64539.1 Example 23.74548.9 Example 33.74548.9 Example 43.64539.1 Example 53.84559.1 Example 63.74549.0 Example 73.74559.0 Example 83.74539.0 Example 93.84549.1 Example 103.64559.1 Example 113.64549.1 Example 123.54559.1 Example 133.54559.0 Example 143.64538.9 Example 153.64548.9 Example 163.54548.7 Example 173.74558.9 Example 183.64538.7 Example 193.64538.8 Example 203.84539.0 Example 213.84548.7 Example 223.64558.9 Comparative Example 15.94584.8 Comparative Example 25.84594.9 Comparative Example 36.14585.1 Comparative Example 44.34566.0 Comparative Example 54.24595.9 Comparative Example 64.34585.8 Comparative Example 74.54587.2 Comparative Example 84.44596.8 Comparative Example 94.44587.0

[0525] Referring to Table 3 above, the organic electroluminescent devices manufactured in Examples 1 to 22 showed generally superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 1 to 9.

[0526] Specifically, the blue organic electroluminescent devices of Examples 1 to 22 used novel organic electroluminescent compounds according to the present invention, which have a structure in which an additional pyrimidine is connected to the 4-position of a pyrimidine via one phenylene or naphthylene, as electron transport layer materials, and thus had faster electron transfer characteristics than compounds H to J having one pyrimidine and compounds K to M in which two pyrimidines are connected via each 2-position, and exhibited a LUMO energy level more suitable for an electron transport layer material than compounds N to P in which two triazines are connected via one phenylene or naphthylene, thereby exhibiting superior electron transfer characteristics to adjacent layers, thereby showing superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 9.

[0527]

[0528] [Examples and Comparative Examples] - 2

[0529] [Examples 23 to 44 and Comparative Examples 10 to 18]: Fabrication of blue organic electroluminescent devices

[0530] After the compounds synthesized in the above synthetic examples were purified to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0531] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then cleaned with UV using a UV OZONE cleaner (Power Sonic 405, Hwasin Tech) for 5 minutes to produce a substrate on which an ITO transparent electrode was formed. The manufactured substrate was then transferred to a vacuum deposition machine.

[0532] An organic electroluminescent device was manufactured by sequentially stacking 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 on the ITO transparent electrode (anode) of the substrate prepared as described above. Specifically, the hole injection layer was formed by co-depositing Compound A and Compound B in a weight ratio of 98:2 on the anode to a thickness of 100 Å, the hole transport layer was formed by depositing Compound A in a thickness of 1400 Å on the hole injection layer, the hole transport auxiliary layer was formed by depositing Compound C in a thickness of 50 Å on the hole transport layer, the light-emitting layer was formed by co-depositing Compound D and Compound E in a weight ratio of 98:2 to a thickness of 200 Å on the hole transport auxiliary layer, the electron transport auxiliary layer was formed by depositing an electron transport auxiliary layer material in a thickness of 50 Å on the light-emitting layer, the electron transport layer was formed by co-depositing Compound Q and Compound G in a weight ratio of 1:1 on the electron transport auxiliary layer to a thickness of 300 Å, the electron injection layer was formed by depositing LiF in a thickness of 10 Å on the electron transport layer, and the cathode was formed by depositing Al in a thickness of 1000 Å on the electron injection layer. Here, the structures of the compounds A to E and compound G are the same as the materials in Table 1 of the above examples and comparative example 1, the structure of compound Q is as shown in Table 4 below, and the electron transport auxiliary layer material is as shown in Table 5 below.

[0533] Compound Q

[0534] Electron transport auxiliary layer material Example 23 Compound 004 Example 24 Compound 009 Example 25 Compound 015 Example 26 Compound 019 Example 27 Compound 044 Example 28 Compound 060 Example 29 Compound 067 Example 30 Compound 075 Example 31 Compound 082 Example 32 Compound 100 Example 33 Compound 116 Example 34 Compound 121 Example 35 Compound 127 Example 36 Compound 131 Example 37 Compound 156 Example 38 Compound 281 Example 39 Compound 284 Example 40 Compound 305 Example Compound 41 Example 312 Compound 42 Example 319 Compound 43 Example 326 Compound 44 Compound 331 Comparative Example 10 Compound H Comparative Example 11 Compound I Comparative Example 12 Compound J Comparative Example 13 Compound K Comparative Example 14 Compound L Comparative Example 15 Compound M Comparative Example 16 Compound N Comparative Example 17 Compound O Comparative Example 18 Compound P

[0535]

[0536] [Experimental Example 2]: Performance evaluation of blue organic electroluminescent devices of Examples 23 to 44 and Comparative Examples 10 to 18

[0537] For the organic electroluminescent devices manufactured in Examples 23 to 44 and Comparative Examples 10 to 18, the driving voltage, luminescence peak, and current efficiency were measured at a current density of 10 mA / cm2, and the results are shown in Table 6 below.

[0538] Driving voltage (V) Luminescence peak (nm) Current efficiency (cd / A) Example 233.84539.0 Example 243.74539.1 Example 253.74549.0 Example 263.74539.0 Example 273.84548.9 Example 283.74548.8 Example 293.84548.8 Example 303.84548.9 Example 313.74558.8 Example 323.74558.9 Example 333.84539.0 Example 343.94549.0 Example 353.84548.9 Example 363.74538.9 Example 373.74538.9 Example 383.74539.0 Example 393.74559.0 Example 403.84539.1 Example 413.74549.1 Example 423.74539.0 Example 433.84539.0 Example 443.74558.9 Comparative Example 104.54588.0 Comparative Example 114.44588.2 Comparative Example 124.74578.0 Comparative Example 134.54568.0 Comparative Example 144.44578.2 Comparative Example 154.54578.1 Comparative Example 166.04577.5 Comparative Example 176.14597.6 Comparative Example 186.04587.5

[0539] Referring to Table 6 above, the organic electroluminescent devices manufactured in Examples 23 to 44 showed overall superior results in driving voltage, luminescence peak, and current efficiency evaluations compared to the organic electroluminescent devices manufactured in Comparative Examples 10 to 18.

[0540] Specifically, the blue organic electroluminescent devices of Examples 23 to 44 used novel organic electroluminescent compounds according to the present invention having a structure in which an additional pyrimidine is connected to the 4-position of a pyrimidine with one phenylene or naphthylene as an electron transport layer material, and thus had faster electron transfer characteristics than compounds H to J having one pyrimidine and compounds K to M in which two pyrimidines are connected through each of the 2-positions, and showed shallower LUMO energy levels than compounds N to P in which two triazines are connected with one phenylene or naphthylene, and thus had superior electron transfer characteristics to the light emitting layer, and thus showed superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 10 to 18.

[0541]

[0542] While the embodiments of the present invention have been described above, those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical concept or essential features thereof. Therefore, the embodiments described above should be understood to be illustrative in all respects, not restrictive.

Claims

1. An organic luminescent compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 and X 2 are each independently N or CR, where R is hydrogen, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 60 carbon atoms, and X 1 and X 2 One of them is N, and the above X 1 and X 2 Except for the case where everyone is N, Ar 1 Inland Ar 4 are each independently an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a heterocycloalkyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 2 to 40 carbon atoms or an arylphosphine oxide group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted, L is an arylene group having 6 to 60 carbon atoms, each of which may be unsubstituted or substituted.

2. In paragraph 1, Above X 1 and X 2 are each independently N or CH, wherein X 1 and X 2 One of them is N, and the above X 1 and X 2 Except for the case where everyone is N, Above Ar 1 Inland Ar 4 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms or an arylphosphine oxide group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a alkylsilyl group having 6 to 30 carbon atoms. It may be substituted with an arylsilyl group of 30, an alkylphosphine oxide group of 2 to 20 carbon atoms, an arylphosphine oxide group of 6 to 30 carbon atoms, a nitrile group or a halogen group, An organic light-emitting compound wherein L is an arylene group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group, or a halogen group.

3. In paragraph 1, Above X 1 and X 2 are each independently N or CH, wherein X 1 and X 2 One of them is N, and the above X 1 and X 2 Except for the case where everyone is N, Above Ar 1 Inland Ar 4 are each independently an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 2 to 10 carbon atoms or an arylphosphine oxide group having 6 to 20 carbon atoms, each of which may be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, a nitrile group or a halogen group, An organic light-emitting compound wherein the above L is an arylene group having 6 to 20 carbon atoms, each of which may be unsubstituted or substituted with a nitrile group.

4. In paragraph 1, Above X 1 and X 2 are each independently N or CH, wherein X 1 and X 2 One of them is N, and the above X 1 and X 2 Except for the case where everyone is N, Above Ar 1 Inland Ar 4 are each independently a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a triphenylphosphine oxide group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a bicyclononyl group, an adamantyl group, a cyclohexyl group, a dimethylphosphine oxide group, a triphenylsilyl group, a nitrile group, or a fluorine group, or each of these rings may form a condensed ring structure, An organic light-emitting compound wherein the above L is a phenylene group or a naphthylene group, each of which may be unsubstituted or substituted with a nitrile group.

5. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound represented by the following chemical formula 2 or chemical formula 3: [Chemical formula 2] [Chemical Formula 3] In each of the chemical formulas 2 and 3 above, Above Ar 1 Inland Ar 4 are each independently a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group or a triphenylphosphine oxide group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a bicyclononyl group, an adamantyl group, a cyclohexyl group, a dimethylphosphine oxide group, a triphenylsilyl group, a nitrile group or a fluorine group, or each of these rings may form a condensed ring structure, L is any one of the following chemical formulas L-1 to L-15, [Chemical Formula L-1] [Chemical Formula L-2] [Chemical Formula L-3] [Chemical Formula L-4] [Chemical Formula L-5] [Chemical Formula L-6] [Chemical Formula L-7] [Chemical Formula L-8] [Chemical Formula L-9] [Chemical Formula L-10] [Chemical Formula L-11] [Chemical Formula L-12] [Chemical Formula L-13] [Chemical Formula L-14] [Chemical formula L-15] In each of the chemical formulas L-1 to L-15 above, * Indicates a site that is bonded to the chemical formula 1 above.

6. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound represented by the following chemical formula 2 or chemical formula 3: [Chemical formula 2] [Chemical Formula 3] In each of the chemical formulas 2 and 3 above, Ar 1 Inland Ar 4 are each independently a phenyl group, a biphenyl group, a tolyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group or a carbazolyl group, each of which may be unsubstituted or substituted with a methyl group, a phenyl group or a carbazolyl group, L is any one of the following chemical formulas L-1 to L-3 and L-5, [Chemical Formula L-1] [Chemical Formula L-2] [Chemical Formula L-3] [Chemical Formula L-5] In each of the chemical formulas L-1 to L-3 and L-5, * Indicates a site that is bonded to the chemical formula 1 above.

7. In paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound which is any one of the following compounds 001 to 336.

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

9. In paragraph 8, The above organic electroluminescent device comprises: an anode; a cathode; a light-emitting layer disposed between the cathode and the anode; and an electron transport region disposed between the cathode and the light-emitting layer. The above electron transport region is an organic electroluminescent device comprising the organic light emitting compound.

10. In paragraph 9, The above electron transport region includes at least one of an electron transport layer and an electron transport auxiliary layer, An organic electroluminescent device, wherein the organic light-emitting compound is included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

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

12. In paragraph 11, A use characterized in that the organic light-emitting compound is used as an electron transport material in the organic electroluminescent device.

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