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. The present invention can achieve excellent performance with low driving voltage, high luminous efficiency, and improved lifespan.

Description

Organic light-emitting compounds and organic electroluminescent devices containing the same

[0001] Cross-citation with related applications

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0142128 filed on October 17, 2024, and all contents disclosed in the document of said Korean Patent Application are incorporated herein as part of this specification.

[0003] Technology field

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

[0005]

[0006] Research on organic electroluminescent (EL) devices has continued since Bernanose’s observation of organic thin-film luminescence in the 1950s, leading to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic electroluminescent device with a stacked structure divided into a hole layer and a functional layer for the emissive layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has progressed by introducing distinct organic layers within the device, leading to the development of specialized materials used for this purpose.

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

[0008] The light-emitting materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials depending on the color of emission. In addition, yellow and orange light-emitting materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as light-emitting materials to increase color purity and luminous efficiency through energy transfer.

[0009] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since the development of these phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, a lot of research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

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

[0011] As such, while conventional organic layer materials have advantages in terms of luminescence characteristics, they do not meet satisfactory standards in terms of the lifespan of organic electroluminescent devices because their low glass transition temperature results in very poor thermal stability.

[0012] Therefore, the development of high-performance organic layer materials is required.

[0013] Prior art literature

[0014] U.S. Patent Publication US 9,831,444 B1

[0015]

[0016] The present invention aims to provide a novel compound and its uses that can be used as an organic layer material for organic electroluminescent devices, specifically as an electron transport layer material and an N-type charge generation layer material, due to its excellent heat resistance, carrier transport capacity, etc.

[0017] In addition, the present invention aims to provide an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and an improved lifespan.

[0018] The problems that the present invention aims to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by a person skilled in the art from the description below.

[0019]

[0020] To solve the above-mentioned problem, the present invention provides an organic light-emitting compound represented by the following chemical formula 1.

[0021] Organic luminescent compound represented by the following chemical formula 1:

[0022] [Chemical Formula 1]

[0023]

[0024] In the above chemical formula 1,

[0025] A is any one of the substituents shown in Chemical Formula 2 below, and

[0026] B is any one of the electron withdrawers (EWGs) shown in Chemical Formula 3 below, and

[0027] L1 and L2 are each independently an arylene having 6 to 60 carbon atoms or a heteroarylene having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and

[0028] m and n are each independently integers from 0 to 3, and

[0029] [Chemical Formula 2]

[0030]

[0031] [Chemical Formula 3]

[0032]

[0033] In the above Chemical Formulas 2 and 3,

[0034] * is connected to L1 or L2, and

[0035] R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, and each may be unsubstituted or substituted.

[0036] Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and adjacent substituents may be connected to each other to form a spiro ring or a fused ring, and

[0037] X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and

[0038] R is independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and

[0039] Y is O or S, and

[0040] The above L1, L2, R1 to R6, Ar1, Ar2, and R are each independently unsubstituted or deuterium, halogen group, cyano group, hydroxyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 nuclei, haloalkyl group having 1 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 5 to 30 nuclei, alkylsilyl group having 1 to 20 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkylboron group having 1 to 20 carbon atoms, and alkyl of 6 to 30 carbon atoms It can be substituted with one or more substituents selected from the group consisting of an arylborone group, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms.

[0041] In addition, the present invention provides an organic electroluminescent device comprising the above organic light-emitting compound.

[0042] In addition, the present invention provides the use of the above-described organic light-emitting compound in an organic electroluminescent device.

[0043]

[0044] The organic light-emitting compound according to the present invention can provide an electron transport layer material or an N-type charge generation layer material having excellent performance in rapid electron mobility and interaction with metals by combining a strong EDG, such as carbazole or amine, with phenanthroline capable of forming metal bonds to enhance metal bonding strength, and at the same time combining an EWG with excellent electron transport capability.

[0045] In addition, by using the compound of the present invention, it is possible to provide an organic electroluminescent device that exhibits a low driving voltage and high luminous efficiency and has an improved lifespan.

[0046] In addition, an organic electroluminescent device comprising an organic light-emitting compound according to the present invention can achieve a low driving voltage, and its light emission performance, lifespan, and efficiency can be significantly improved.

[0047] The effects of the present invention are not limited to those mentioned above, and other unmentioned effects will be clearly understood by a person skilled in the art from the description below.

[0048]

[0049] The advantages and features of the present invention and the methods for achieving them will become clear by referring to the embodiments described in detail below. However, the present invention is not limited to the embodiments disclosed below but can be implemented in various different forms. These embodiments are provided merely 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 only by the scope of the claims.

[0050] The terms used herein are for describing the embodiments and are not intended to limit the invention. In this specification, the singular form includes the plural form unless specifically stated otherwise in the text. As used herein, "comprises" and / or "comprising" do not exclude the presence or addition of one or more other components in addition to the components mentioned.

[0051] Unless otherwise defined, all terms used herein (including technical and scientific terms) may be used in a meaning commonly understood by those skilled in the art to which the present invention pertains. Additionally, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0052] Hereinafter, embodiments of the present invention will be described in detail.

[0053] Prior to the explanation, the meanings of the terms used in this specification are briefly explained. However, since the explanation of terms is intended to aid in understanding this specification, it should be noted that they are not used to limit the technical scope of the invention unless explicitly stated to be a limiting factor.

[0054] In the present invention, the term "aryl group" may refer to a monovalent functional group derived from an aromatic hydrocarbon. The above aryl group may mean, for example, a phenyl group, a naphthyl group, anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a chrysenyl group, a spirobifluorenyl group, a fluoranthenyl group, a fluorenyl group, a perylenyl group, an indenyl group, an azulenyl group, a heptalenyl group, a phenalenyl group, a phenanthrenyl group, a phenanthrenyl group, and the like, but is not limited thereto. In addition, the term "arylene group" may refer to a divalent functional group derived from an aromatic hydrocarbon.

[0055] In the present invention, the term "heteroaryl group" may refer to a monovalent functional group derived from an aromatic heterocyclic ring of a single ring 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 heteroatoms in addition to carbon atoms. Specific examples of the above heteroaryl groups include: pyrrolyl group, pyridyl group, pyridazinyl group, triazinyl group, pyrimidinyl group, pyrazinyl group, naphthyridyl group, acenaphthopyridyl group, triazolyl group, tetrazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indolyl group, isoindolyl group, indolizinyl group, and purinyl group. group), indazolyl group, quinolyl group, benzoquinolyl group, isoquinolinyl group, quinolizinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, imidazotriazinyl group,A nitrogen-containing heteroaryl group including an acridinyl group, a phenanthridyl group, a carbazolyl group, a phenanthrolinyl group, a phenazinyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a pyrazolopyridyl group, a heptaazaphenalenyl group, etc.; a sulfur-containing heteroaryl group including a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzonaphthothiophenyl group, etc.; Examples include oxygen-containing heteroaryl groups including furyl groups, pyranyl groups, benzofuranyl groups, isobenzofuranyl groups, dibenzofuranyl groups, benzonaphthofuranyl groups, oxanthrenyl groups, xanthenyl groups, benzoxanthenyl groups, etc.; oxygen and sulfur complex-containing heteroaryl groups including thiadiazolyl groups, oxadiazolyl groups, phenoxathiinyl groups, benzothienopyrimidinyl groups, and benzofuropyridyl groups. In addition, the term "heteroarylene group" refers to nitrogen (N), sulfur (S), oxygen (O), phosphorus (P) as heteroatoms,It may refer to a divalent functional group derived from an aromatic hydrocarbon containing at least one of selenium (Se) and silicon (Si). In the heteroaryl group and heteroarylene group, the number of nuclei may be defined instead of the number of carbon atoms. Here, the number of nuclei may refer to the number of atoms including one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si), in addition to carbon (C) atoms. For example, the heteroaryl group and heteroarylene group may each have a number of nuclei of 5 to 60, 5 to 30, or 5 to 20.

[0056] In the present invention, the term "alkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of a linear or branched structure.The above alkyl group is, 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, 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 2-methylpentyl group, and 3-methylpentyl group.

[0057] In the present invention, the term "cycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of 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.

[0058] In the present invention, the term "heterocycloalkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon of a ring structure, and the heterocycloalkyl group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a heteroatom in addition to a carbon atom. The heterocycloalkyl group may be defined by the number of nuclei instead of the number of carbon atoms. Here, the number of nuclei may refer to the number of atoms including one or more heteroatoms selected from the group consisting of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) in addition to the carbon (C) atom. For example, the heterocycloalkyl group may have a number of nuclei of 3 to 60, 3 to 30, or 3 to 20.

[0059] In the present invention, the term "alkenyl group" may refer to a monovalent functional group derived from a hydrocarbon containing one or more carbon double bonds at the middle or end of an alkyl group.

[0060] In the present invention, the term "alkynyl group" may refer to a monovalent functional group derived from a hydrocarbon containing one or more carbon triple bonds at the middle or end of an alkyl group.

[0061] In the present invention, the term "haloalkyl group" may refer to a monovalent functional group derived from a compound in which a halogen atom is substituted on one or more of the hydrogens of the aforementioned alkyl group. Here, the halogen atom may be one or more of F, Cl, Br, and I.

[0062] In the present invention, the terms "alkylsilyl group" and "arylsilyl group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of a silane are substituted with the aforementioned alkyl group or aryl group.

[0063] In the present invention, the terms "alkylamine group" and "arylamine group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of an amine are substituted with the aforementioned alkyl group or aryl group.

[0064] In the present invention, the terms "alkylboron group" and "arylboron group" may each refer to a monovalent functional group derived from a compound in which one or more of the hydrogens of the boran are substituted with the aforementioned alkyl group or aryl group.

[0065] In the present invention, the term "arylphosphine group" may refer to a monovalent functional group derived from a compound in which the aforementioned aryl group is substituted on phosphine.

[0066] In the present invention, the terms "alkylphosphine oxide group" and "arylphosphine oxide group" may each refer to a monovalent functional group derived from a compound in which the aforementioned alkyl group or aryl group is substituted on phosphine oxide.

[0067] In the present invention, the term "substitution" each independently refers to a deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, and a group having 6 to It means being substituted with one or more substituents selected from the group consisting of 30 arylphosphine oxide groups, alkylamine groups having 1 to 20 carbon atoms, and arylamine groups having 6 to 30 carbon atoms, and when substituted with multiple substituents, they may be the same or different from each other.

[0068] In the present invention, the terms "spiro ring" and "fused ring" refer to a ring structure formed by connecting adjacent substituents. Specifically, a spiro ring refers to a ring structure formed by connecting two substituents that have been substituted on one carbon atom, and a fused ring refers to a ring structure formed by connecting substituents that have been substituted on adjacent carbon atoms. The spiro ring and the fused ring may be ring structures with 3 to 10 nuclei, and the formed ring structure may be a cycloalkane, cycloalkene, heterocycloalkane, or heterocycloalkene structure, and the heteroatom may be O, N, or S. For example, the spiro ring and the fusion ring may each be cyclopentane, cyclohexane, cyclopentene, cyclohexene, tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, or piperidine, and these may each be unsubstituted or substituted with a substituent defined in the present invention.

[0069]

[0070] Organic light-emitting compounds

[0071] The present invention provides a novel organic light-emitting compound. The organic light-emitting compound is represented by the following chemical formula 1.

[0072] [Chemical Formula 1]

[0073]

[0074] In the above chemical formula 1,

[0075] A is any one of the substituents shown in Chemical Formula 2 below, and

[0076] B is any one of the electron withdrawers (EWGs) shown in Chemical Formula 3 below, and

[0077] L1 and L2 are each independently an arylene having 6 to 60 carbon atoms or a heteroarylene having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and

[0078] m and n are each independently integers from 0 to 3, and

[0079] [Chemical Formula 2]

[0080]

[0081] [Chemical Formula 3]

[0082]

[0083] In the above Chemical Formulas 2 and 3,

[0084] * is connected to L1 or L2, and

[0085] R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, and each may be unsubstituted or substituted.

[0086] Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and adjacent substituents may be connected to each other to form a spiro ring or a fused ring, and

[0087] X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and

[0088] R is independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and

[0089] Y is O or S, and

[0090] The above L1, L2, R1 to R6, Ar1, Ar2, and R are each independently unsubstituted or deuterium, halogen group, cyano group, hydroxyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 nuclei, haloalkyl group having 1 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 5 to 30 nuclei, alkylsilyl group having 1 to 20 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkylboron group having 1 to 20 carbon atoms, and alkyl of 6 to 30 carbon atoms It can be substituted with one or more substituents selected from the group consisting of an arylborone group, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms.

[0091] In one embodiment, when m is 0

[0092] In one embodiment, when m is 0, L1 does not exist and means that A and the phenanthroline moiety are single-bonded.

[0093] In one embodiment, when n is 0, L2 does not exist and means that B and the phenanthroline moiety are single-bonded.

[0094]

[0095] In one embodiment, in the above formula 1,

[0096] The above L1 and L2 are each independently an arylene having 6 to 30 carbon atoms or a heteroarylene having 5 to 30 nuclei, and each of these may be unsubstituted or substituted, and

[0097] m is an integer from 0 to 2, and

[0098] n is an integer from 0 to 3, and

[0099] The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, and each of these may be unsubstituted or substituted.

[0100] Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted, and adjacent substituents may be connected to each other to form a spiro ring or a fused ring, and

[0101] X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and

[0102] R is independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted.

[0103]

[0104] In one embodiment, in the above formula 1,

[0105] The above L1 and L2 are each independently an arylene having 6 to 30 carbon atoms or a heteroarylene having 5 to 30 nuclei, each of which is unsubstituted or a deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, It can be substituted with one or more substituents selected from the group consisting of an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and

[0106] m is 0 or 1, and

[0107] n is an integer from 0 to 3, and

[0108] The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, and these are each unsubstituted or deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, It can be substituted with one or more substituents selected from the group consisting of an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms.

[0109] Ar1 and Ar2 are each independently selected from the group consisting of phenyl groups, naphthyl groups, biphenyl groups, terphenyl groups, anthracenyl groups, naphthasenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, fluorenyl groups, and dibenzofuranyl groups, each of which is unsubstituted or deuterium, halogen groups, cyano groups, hydroxyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, pyridinyl groups, alkenyl groups having 2 to 20 carbon atoms, alkynyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, heterocycloalkyl groups having 3 to 20 nuclei, haloalkyl groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, heteroaryl groups having 5 to 30 nuclei, and 1 to It can be substituted with one or more substituents selected from the group consisting of 20 alkylsilyl groups, 6 to 30 arylsilyl groups, 1 to 20 alkylboron groups, 6 to 30 arylboron groups, 6 to 30 arylphosphine groups, 1 to 20 alkylphosphine oxide groups, 6 to 30 arylphosphine oxide groups, 1 to 20 alkylamine groups, and 6 to 30 arylamine groups, and adjacent substituents can be connected to each other to form a spiro ring or a fused ring.

[0110] X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and

[0111] R is each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which is unsubstituted or deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, and 6 to It can be substituted with one or more substituents selected from the group consisting of 30 arylborone groups, 6 to 30 carbon atom arylphosphine groups, 1 to 20 carbon atom alkylphosphine oxide groups, 6 to 30 carbon atom arylphosphine oxide groups, 1 to 20 carbon atom alkylamine groups, and 6 to 30 carbon atom arylamine groups.

[0112]

[0113] In one embodiment, in the above formula 1,

[0114] The above L1 and L2 are each independently an arylene having 6 to 20 carbon atoms or a heteroarylene having 5 to 20 nuclei, and

[0115] m is 0 or 1, and

[0116] n is an integer from 0 to 3, and

[0117] The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei.

[0118] Ar1 and Ar2 are each independently selected from the group consisting of phenyl groups, naphthyl groups, biphenyl groups, and terphenyl groups, and adjacent substituents can be connected to each other to form a spiro ring or a fused ring, and

[0119] X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and

[0120] R can each independently be hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei.

[0121]

[0122] In one embodiment, the organic light-emitting compound represented by the above formula 1 may be any one selected from the following compounds 1 to 214.

[0123]

[0124]

[0125] As a specific example, the compound represented by the above chemical formula 1 may be any one selected from the above compounds 5, 9, 15, 19, 21, 31, 93, 96, 129, 137 and 144.

[0126] The organic light-emitting compound according to the present invention has a strong EDG, such as carbazole or amine, bonded to phenanthroline capable of forming a metal bond to enhance the metal bonding strength, and at the same time, an EWG with excellent electron transport capability is bonded to provide fast electron mobility and excellent performance in interaction with metal.

[0127] In addition, by using the novel organic light-emitting compound according to the present invention as an electron transport layer and an N-type charge generation layer material, excellent performance can be achieved, such as a low driving voltage, high luminous efficiency, and improved lifespan of the organic electroluminescent device.

[0128]

[0129] Organic Electroluminescent Device

[0130] The present invention provides an organic electroluminescent device comprising the novel organic light-emitting compound described above. The organic light-emitting compound according to the present invention may be included in one or more of the organic layers disposed between the cathode and the anode of the organic electroluminescent device.

[0131] 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.

[0132] anode

[0133] 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.

[0134] The type of the anode material is not specifically limited and can be manufactured according to conventional methods known in the industry. The anode material may be, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); composites of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers 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 in combination of two or more types.

[0135] The method of manufacturing the above anode is not particularly limited and can be manufactured according to conventional methods known in the industry. The above anode can be formed by coating an anode material onto a substrate, such as, for example, a silicon wafer, quartz, a glass plate, a metal plate, and a plastic film.

[0136] cathode

[0137] The organic electroluminescent device of the present invention includes a cathode. The cathode serves to inject electrons into an organic layer.

[0138] The type of cathode material forming the above cathode is not specifically limited and can be manufactured according to conventional methods known in the industry. 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 multilayer structural materials such as LiF / Al or LiO2 / Al.

[0139] light-emitting layer

[0140] 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.

[0141] The light-emitting material forming the above-mentioned light-emitting layer may use various commercially available materials without special restrictions, depending on the desired wavelength of emitted light.

[0142] In one embodiment, the light-emitting material can be classified into blue, green, red, etc., depending on the light emission color. To prevent problems such as reduced color purity or decreased efficiency of the device due to light emission attenuation effects, the light-emitting material can form a light-emitting layer by mixing a host material and a dopant material. The light-emitting efficiency of the light-emitting device can be improved by using a host material, which is the main material forming the light-emitting layer, and a small amount of dopant having a smaller energy band gap compared to the host material.

[0143] Electronic transport area

[0144] The organic electroluminescent device of the present invention includes an electron transport region disposed between the light-emitting layer and the cathode.

[0145] The above electron transport region serves to move electrons injected from the cathode to the light-emitting layer. This electron transport region may include one or more types 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 aforementioned electron transport layer and electron injection layer.

[0146] In the electron transport region above, the electron injection layer can use an electron injection material that facilitates electron injection from the cathode and has high electron mobility without limitation. Non-limiting examples of usable electron injection materials include the above-mentioned anode compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As a specific example, the electron injection material may include one or more selected from the group consisting of lanthanide metals such as LiF, Li2O, BaO, NaCl, CsF; Yb, etc.; and halogenated metals such as RbCl, RbI, etc.

[0147] The electron transport layer described above may include the organic light-emitting compound according to the present invention. In addition, by using the novel organic light-emitting compound according to the present invention as the electron transport layer material, excellent performance can be achieved in terms of driving voltage, emission peak, current efficiency, and lifespan.

[0148] The electron transport layer above can be formed by mixing the organic light-emitting compound according to the present invention with Liq (Lithium quinolate). The conduction band of Liq is 5.58 eV and the valence band is 3.153 eV, which has the effect of lowering the potential barrier.

[0149] The electron transport region can be manufactured using conventional methods known in the relevant technical field. Examples of electron transport regions include, but are not limited to, vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0150] Electron transport auxiliary layer

[0151] 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.

[0152] The electron transport assist layer described above may include the organic light-emitting compound according to the present invention. In addition, by using the novel organic light-emitting compound according to the present invention as the electron transport assist layer material, excellent performance can be achieved in terms of driving voltage, emission peak, and current efficiency.

[0153] As is known in the art, the above electron transport assist layer can be formed by vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc., but is not limited thereto.

[0154] Precision transport area

[0155] 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.

[0156] The hole transport region described above may include one or more 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 aforementioned hole injection layer and the hole transport layer.

[0157] The materials forming the hole injection layer and the hole transport layer are not particularly limited as long as they are materials with a low hole injection barrier and high hole mobility, and hole injection materials and hole transport materials used in the industry 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.

[0158] The hole injection material mentioned above may be any hole injection material known in the art without limitation. Non-limiting examples of usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,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)). These can be used alone, Or, two or more types can be mixed.

[0159] In addition, the hole transport material mentioned above may be any hole transport material known in the art without limitation. Non-limiting examples of usable hole transport materials 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) and TCTA (4,4',4"-tris(Ncarbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine) and TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), and these may be used alone or in combination of two or more types.

[0160] The hole transport region described above can be manufactured through conventional methods known in the art. Examples include, but are not limited to, vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0161] Precision transport auxiliary layer

[0162] The organic electroluminescent device of the present invention may further include a hole transport auxiliary layer disposed between the hole transport region and the light-emitting layer. The hole transport auxiliary layer serves to transport holes moving from the hole transport region to the light-emitting layer and to control the thickness of the organic layer. This hole transport 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 of the light-emitting layer from diffusing into the hole transport layer.

[0163] These hole transport auxiliary layers may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the hole transport auxiliary layers of red, green, and blue organic light-emitting diodes may be made of the same material.

[0164] The hole transport assisting layer material is not particularly limited and, for example, carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives may be used. In addition, the hole transport assisting layer may optionally include a p-type dopant in addition to the aforementioned materials. As the p-type dopant, known p-type dopants used in the relevant art field may be used.

[0165] capping layer

[0166] The organic electroluminescent device of the present invention may further include a capping layer disposed on the cathode. The capping layer protects the organic light-emitting device while facilitating the efficient emission of light generated from the organic layer to the outside.

[0167] The capping material forming the capping layer may include, for example, one or more 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), and 1,1'-bis(di-4-tolylaminophenyl) cyclohexane (TAPC), but is not limited thereto.

[0168] The capping layer may be a single layer, but may include two or more layers having different refractive indices, so that the refractive index changes gradually as it passes through the two or more layers.

[0169] The above capping layer can be manufactured through conventional methods known in the art, and various methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method can be used.

[0170] tandem element

[0171] The organic electroluminescent device of the present invention may be a tandem device having a plurality of light-emitting units. The tandem device typically includes an anode; a cathode; a plurality of light-emitting units disposed between the cathode and the anode; and a charge generating layer comprising an N-type charge generating layer and a P-type charge generating layer interposed between adjacent light-emitting units.

[0172] Such tandem organic electroluminescent devices have at least two light-emitting units, and the number of light-emitting units can be increased by interposing a charge-generating layer between adjacent light-emitting units.

[0173] The charge generation layer is positioned between adjacent light-emitting units to regulate the charge between the light-emitting units, thereby achieving charge balance.

[0174] Among the charge generation layers above, the N-type charge generation layer may include the organic light-emitting compound according to the present invention described above. Furthermore, by using the novel organic light-emitting compound according to the present invention as the N-type charge generation layer material, excellent performance can be achieved in terms of driving voltage, luminous efficiency, and lifespan.

[0175] The thickness of the N-type charge generating layer is not particularly limited and, for example, may be in the range of 5 to 30 nm.

[0176] The above P-type charge generating layer may be composed of a metal or a P-type doped organic material. Here, the metal includes Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti, and these may be used alone or as an alloy of two or more. In addition, the P-type dopant and host materials used in the above P-type doped organic material are not particularly limited as long as they are commonly used materials. For example, the above P-type dopant includes F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), iodine, FeCl3, FeF3, and SbCl5, and these may be used alone or as a mixture of two or more. In addition, non-limiting examples of the above host include NPB (N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine), TPD (N,N'-bis(3-methylphenyl)N,N'-bis(phenyl)-benzidine), and TNB (N,N,N',N'-tetra-naphthalenyl-benzidine), which may be used alone or in combination of two or more.

[0177]

[0178] The present invention provides an application of the above-described organic light-emitting compound in an organic electroluminescent device. Through this, it provides an organic electroluminescent device with significantly improved luminescence performance, driving voltage, lifespan, and efficiency.

[0179] In one embodiment, the organic light-emitting compound may be used as an electron transport material in the organic electroluminescent device.

[0180] In one embodiment, the organic light-emitting compound may be used as a material for an electron transport region and / or an electron transport auxiliary layer in the organic electroluminescent device.

[0181] In one embodiment, the organic light-emitting compound can be used as a material for an N-type charge generation layer in the organic electroluminescent device.

[0182]

[0183] The present invention will be described in detail below through examples, but the following examples are merely illustrative of the invention and the invention is not limited by the following examples.

[0184]

[0185] [Preparation Example 1] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-chlorophenyl)-1,10-phenanthroline (C1-1)

[0186]

[0187] 2-chloro-9-(3-chlorophenyl)-1,10-phenanthroline (30.0g, 92.3mmol) and (3-(9H-carbazol-9-yl)phenyl)boronic acid (26.5g, 92.3mmol), Pd(PPh3)4 (3.2g, 2.8mmol), and K2CO3 (38.3g, 276.8mmol) were added to 360ml of toluene, 60ml of ETOH, and 60ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-chlorophenyl)-1,10-phenanthroline (C1-1) (40.7 g, 76.6 mmol, yield 83%).

[0188] Mass : [(M+H)+] : 533

[0189]

[0190] [Preparation Example 2] Synthesis of 2-(3-chlorophenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (C2-1)

[0191]

[0192] 2-chloro-9-(3-chlorophenyl)-1,10-phenanthroline (30.0g, 92.3mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid (26.5g, 92.3mmol), Pd(PPh3)4 (3.2g, 2.8mmol), and K2CO3 (38.3g, 276.8mmol) were added to 360ml of toluene, 60ml of ETOH, and 60ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (C2-1) (39.8 g, 74.7 mmol, yield 81%).

[0193] Mass : [(M+H)+] : 533

[0194]

[0195] [Preparation Example 3] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-chlorophenyl)-1,10-phenanthroline (C3-1)

[0196]

[0197] 2-chloro-9-(4-chlorophenyl)-1,10-phenanthroline (30.0 g, 92.3 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid (26.5 g, 92.3 mmol), Pd(PPh3)4 (3.2 g, 2.8 mmol), and K2CO3 (38.3 g, 276.8 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-chlorophenyl)-1,10-phenanthroline (C3-1) (39.8 g, 74.7 mmol, yield 81%).

[0198] Mass : [(M+H)+] : 533

[0199]

[0200] [Preparation Example 4] Synthesis of 2-(4-chlorophenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (C4-1)

[0201]

[0202] 2-chloro-9-(4-chlorophenyl)-1,10-phenanthroline (30.0g, 92.3mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid (26.5g, 92.3mmol), Pd(PPh3)4 (3.2g, 2.8mmol), and K2CO3 (38.3g, 276.8mmol) were added to 360ml of toluene, 60ml of ETOH, and 60ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (C4-1) (40.2 g, 75.6 mmol, yield 82%).

[0203] Mass : [(M+H)+] : 533

[0204]

[0205] [Preparation Example 5] Synthesis of 3-(9-(3-chlorophenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (C5-1)

[0206]

[0207] 2-chloro-9-(3-chlorophenyl)-1,10-phenanthroline (30.0g, 92.3mmol), (3-(diphenylamino)phenyl)boronic acid (26.7g, 92.3mmol), Pd(PPh3)4 (3.2g, 2.8mmol), and K2CO3 (38.3g, 276.8mmol) were added to 360ml of toluene, 60ml of ETOH, and 60ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3-(9-(3-chlorophenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (C5-1) (38.9 g, 72.9 mmol, yield 79%).

[0208] Mass : [(M+H)+] : 535

[0209]

[0210] [Preparation Example 6] Synthesis of 3-(9-(4-chlorophenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (C6-1)

[0211]

[0212] 2-chloro-9-(4-chlorophenyl)-1,10-phenanthroline (30.0g, 92.3mmol), (3-(diphenylamino)phenyl)boronic acid (26.7g, 92.3mmol), Pd(PPh3)4 (3.2g, 2.8mmol), and K2CO3 (38.3g, 276.8mmol) were added to 360ml of toluene, 60ml of ETOH, and 60ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3-(9-(4-chlorophenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (C6-1) (41.9 g, 78.4 mmol, yield 85%).

[0213] Mass : [(M+H)+] : 535

[0214]

[0215] [Preparation Example 7] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C1)

[0216]

[0217] C1-1 (20.0g, 37.6mmol), bis(pinacolato)diboron (12.4g, 48.9mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.4g, 75.2mmol), synthesized by the method of Preparation Example 1, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C1) (16.4g, 26.3mmol, yield 70%).

[0218] Mass : [(M+H) + ] : 625

[0219]

[0220] [Preparation Example 8] Synthesis of 2-(9-phenyl-9H-carbazol-3-yl)-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C2)

[0221]

[0222] C2-1 (20.0g, 37.6mmol), bis(pinacolato)diboron (12.4g, 48.9mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.4g, 75.2mmol), synthesized by the method of Preparation Example 2, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 2-(9-phenyl-9H-carbazol-3-yl)-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C2) (15.9g, 25.6mmol, yield 68%).

[0223] Mass : [(M+H) + ] : 625

[0224]

[0225] [Preparation Example 9] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C3)

[0226]

[0227] C3-1 (20.0g, 37.6mmol), bis(pinacolato)diboron (12.4g, 48.9mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.4g, 75.2mmol), synthesized by the method of Preparation Example 3, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C3) (16.2g, 25.9mmol, yield 69%).

[0228] Mass : [(M+H) + ] : 625

[0229]

[0230] [Preparation Example 10] Synthesis of 2-(9-phenyl-9H-carbazol-3-yl)-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C4)

[0231]

[0232] C4-1 (20.0g, 37.6mmol), bis(pinacolato)diboron (12.4g, 48.7mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.4g, 75.2mmol), synthesized by the method of Preparation Example 4, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 2-(9-phenyl-9H-carbazol-3-yl)-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (C4) (16.2g, 25.9mmol, yield 69%).

[0233] Mass : [(M+H) + ] : 625

[0234]

[0235] [Preparation Example 11] Synthesis of N,N-diphenyl-3-(9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl)aniline (C5)

[0236]

[0237] C5-1 (20.0g, 37.4mmol), bis(pinacolato)diboron (12.4g, 48.7mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.2mmol), and KOAc (7.4g, 74.9mmol), synthesized by the method of Preparation Example 5, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 N,N-diphenyl-3-(9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl)aniline (C5) (16.4g, 26.2mmol, yield 70%).

[0238] Mass : [(M+H) + ] : 625

[0239]

[0240] [Preparation Example 12] Synthesis of N,N-diphenyl-3-(9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl)aniline (C6)

[0241]

[0242] C6-1 (20.0g, 37.4mmol), bis(pinacolato)diboron (12.4g, 48.7mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.2mmol), and KOAc (7.4g, 74.9mmol), synthesized by the method of Preparation Example 6, were added to 200ml of 1,4-Dioxane and heated and refluxed 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 N,N-diphenyl-3-(9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl)aniline (C6) (16.9g, 27.0mmol, yield 72%).

[0243] Mass : [(M+H) + ] : 627

[0244]

[0245] [Preparation Example 13] Synthesis of 2-(2-(6-chloropyridin-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (S1)

[0246]

[0247] 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (30.0 g, 68.9 mmol), 2-bromo-6-chloropyridine (13.3 g, 68.9 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), and K2CO3 (28.6 g, 206.7 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(2-(6-chloropyridin-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (S1) (24.7 g, 58.6 mmol, yield 85%).

[0248] Mass : [(M+H)+] : 422

[0249]

[0250] [Synthesis Example 1] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (5)

[0251]

[0252] (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 7, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline ( 5 ) (13.9 g , 19.0 mmol , yield 79%).

[0253] Mass : [(M+H)+] : 730

[0254]

[0255] [Synthesis Example 2] Synthesis of 2-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (9)

[0256]

[0257] C2 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 8, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (9) (14.2 g, 19.5 mmol, yield 81%).

[0258] Mass : [(M+H)+] : 730

[0259]

[0260] [Synthesis Example 3] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (15)

[0261]

[0262] C3 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 9, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, water was removed with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (15) (14.2 g, 19.5 mmol, yield 81%).

[0263] Mass : [(M+H)+] : 730

[0264]

[0265] [Synthesis Example 4] Synthesis of 2-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (19)

[0266]

[0267] C4 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 10, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, the water was removed with Magnesium Sulfate, the mixture was concentrated, and purified by column chromatography to obtain 2-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9-(9-phenyl-9H-carbazol-3-yl)-1,10-phenanthroline (19) (14.7 g, 20.2 mmol, yield 84%).

[0268] Mass : [(M+H)+] : 730

[0269]

[0270] [Synthesization Example 5] Synthesis of 3-(9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (21)

[0271]

[0272] C5 (15.0 g, 24.0 mmol) synthesized by the method of Preparation Example 11, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.0 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (9.9 g, 71.9 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, water was removed with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3-(9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (21) (14.4 g, 19.7 mmol, yield 82%).

[0273] Mass : [(M+H)+] : 732

[0274]

[0275] [Synthesization Example 6] Synthesis of 3-(9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (31)

[0276]

[0277] C6 (15.0 g, 24.0 mmol) synthesized by the method of Preparation Example 12, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24.0 mmol), (6.4 g, 24.0 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (9.9 g, 71.9 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, the water was removed with Magnesium Sulfate, the mixture was concentrated, and purified by column chromatography to obtain 3-(9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthrolin-2-yl)-N,N-diphenylaniline (31) (14.0 g, 19.2 mmol, yield 80%).

[0278] Mass : [(M+H)+] : 732

[0279]

[0280] [Synthesis Example 7] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (137)

[0281]

[0282] C1 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 7, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.3 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (137) (14.5 g, 18.0 mmol, yield 75%).

[0283] Mass : [(M+H)+] : 806

[0284]

[0285] [Synthesis Example 8] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (144)

[0286]

[0287] C1 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 7, 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (7.6 g, 24.1 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.0 g, 72.2 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was finished, the organic layer was extracted with Methylene Chloride, water was removed with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-1,10-phenanthroline (144) (14.6 g, 18.8 mmol, yield 78%).

[0288] Mass : [(M+H)+] : 780

[0289]

[0290] [Synthesis Example 9] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (93)

[0291]

[0292] C1 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 7, and S-5 (8.3 g, 24.1 mmol) and Cs2CO3 (15.7 g, 48.1 mmol) synthesized by the method of Preparation Example 20 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.2 g, 0.7 mmol) and X-Phos (0.7 g, 1.4 mmol) were added and heated and stirred under active water for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(3-(9H-carbazol-9-yl)phenyl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (93) (15.3g, 19.0mmol, yield 79%).

[0293] Mass : [(M+H)+] :806

[0294]

[0295] [Synthesis Example 10] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1,10-phenanthroline (96)

[0296]

[0297] C3 (15.0 g, 24.1 mmol) synthesized by the method of Preparation Example 9, and S-5 (8.3 g, 24.1 mmol) and Cs2CO3 (15.7 g, 48.1 mmol) synthesized by the method of Preparation Example 20 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.2 g, 0.7 mmol) and X-Phos (0.7 g, 1.4 mmol) were added and heated and stirred under running water for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(3-(9H-carbazol-9-yl)phenyl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1,10-phenanthroline (96) (15.3g, 19.0mmol, yield 79%).

[0298] Mass : [(M+H)+] :806

[0299]

[0300] [Synthesis Example 11] Synthesis of 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(6-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)phenyl)-1,10-phenanthroline (129)

[0301]

[0302] S1 (15.0g, 35.6mmol) synthesized by the method of Preparation Example 13 and C3 (22.2g, 35.6mmol), Pd(PPh3)4 (1.2g, 1.1mmol), and K2CO3 (14.8g, 106.9mmol) synthesized by the method of Preparation Example 9 were added to 180ml of Toluene, 30ml of ETOH, and 30ml of Water, and heated and refluxed for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(3-(9H-carbazol-9-yl)phenyl)-9-(4-(6-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridin-2-yl)phenyl)-1,10-phenanthroline (129) (26.7 g, 30.3 mmol, yield 85%).

[0303] Mass : [(M+H)+] : 883

[0304]

[0305] [Example]

[0306]

[0307] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0308] Compound 5 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0309] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0310] On the ITO transparent electrode prepared as described above, compound 001 and compound 002 were co-deposited in a weight ratio of 98:2 to form a hole injection layer of 100 Å, then compound 001 was deposited on the hole injection layer to form a hole transport layer of 1400 Å thickness, then compound 003 was deposited on the hole transport layer to a thickness of 50 Å to form a hole transport assist layer, and compound 004 and compound 005 were co-deposited in a weight ratio of 98:2 to form a light-emitting layer of 200 Å thickness. An organic light-emitting device was fabricated by depositing compound 006 on the upper surface of the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then co-depositing compound 5 and compound 007 in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å, depositing LiF on the upper surface of the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the upper surface of the electron injection layer to form a cathode with a thickness of 1000 Å.

[0311] The structures of compounds 001 to 007 used at this time are as follows.

[0312]

[0313]

[0314] [Examples 2 to 11] Fabrication of Blue Organic Electroluminescent Devices

[0315] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 5 used as the electron transport layer material.

[0316]

[0317] [Comparative Examples 1 to 5] Fabrication of Blue Organic Electroluminescent Devices

[0318] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that compounds A to E were used respectively instead of compound 5 used as the electron transport layer material.

[0319]

[0320]

[0321] [Evaluation Example 1]

[0322] For the blue organic electroluminescent devices fabricated in Examples 1 to 11 and Comparative Examples 1 to 5, respectively, the driving voltage, emission peak, current efficiency, and lifetime at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0323] Sample Electron Transport Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Lifetime (h) Example 1 Compound 53.74578.5330 Example 2 Compound 93.74568.4335 Example 3 Compound 153.74568.4336 Example 4 Compound 193.84578.4335 Example 5 Compound 213.74568.5327 Example 6 Compound 313.84588.6328 Example 7 Compound 933.84588.5315 Example 8 Compound 963.84578.5315 Example 9 Compound 1293.84578.6320 Example 10 Compound 1373.74588.5326 Example 11 Compound 1443.74578.4334 Comparative Example 1 Compound A 4.34587.1190 Comparative Example 2 Compound B 4.34597.0195 Comparative Example 3 Compound C 5.44596.9185 Comparative Example 4 Compound D 5.34596.7184 Comparative Example 5 Compound E 6.04596.8170

[0324]

[0325] As shown in Table 1 above, the blue organic electroluminescent devices of Examples 1 to 11, which used the compound according to the present invention in the electron transport layer, exhibited superior performance in driving voltage, emission peak, current efficiency, and device lifespan compared with materials in which the phenanthroline moiety is combined with EWG without EDG, materials in which the EDG is connected to a linker connecting phenanthroline and EWG or to EWG, and materials that do not contain phenanthroline.

[0326]

[0327] [Example 12] Fabrication of an Organic Electroluminescent Device

[0328] Compound 5 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0329] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0330] On the ITO transparent electrode prepared as described above, compound 001 and compound 002 were co-deposited in a weight ratio of 98:2 to form a hole injection layer of 100 Å, then compound 001 was deposited on the hole injection layer to form a hole transport layer of 200 Å thickness, then compound 003 was deposited to a thickness of 50 Å on the hole transport layer to form a hole transport assist layer, and compound 004 and compound 005 were co-deposited in a weight ratio of 98:2 to form a emitting layer of 200 Å thickness. Compound 007 was deposited to a thickness of 150 Å on the emitting layer to form an electron transport region, and compound 5 and 2% Li were co-deposited on the electron transport region to form an N-type charge generation layer of 80 Å thickness. Compound 001 and Compound 002 were co-deposited in a weight ratio of 98:2 on an N-type charge generation layer to form a 100 Å P-type charge generation layer, then Compound 001 was deposited on the P-type charge generation layer to form a 350 Å thick hole transport layer, then Compound 003 was deposited to a thickness of 50 Å on the hole transport layer to form a hole transport assist layer, and then Compound 004 and Compound 005 were co-deposited in a weight ratio of 98:2 to form a 200 Å thick emissive layer. An organic light-emitting device was fabricated by depositing compound 006 on the upper surface of the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then depositing compound 007 and compound 008 in a weight ratio of 1:1 to form an electron transport region with a thickness of 300 Å, depositing LiF on the upper surface of the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the upper surface of the electron injection layer to form a cathode with a thickness of 1000 Å.

[0331] The structures of compounds 001 to 007 used at this time are the same as those described in Example 1, and the structure of compound 008 is as follows.

[0332]

[0333]

[0334] [Examples 13 to 22] Fabrication of Organic Electroluminescent Devices

[0335] An organic electroluminescent device was fabricated by performing the same procedure as in Example 12, except that the compounds in Table 2 were used instead of Compound 5, which was used as the N-type charge generation layer material in Example 12.

[0336]

[0337] [Comparative Examples 6 to 10] Fabrication of Organic Electroluminescent Devices

[0338] An organic electroluminescent device was fabricated in the same manner as in Example 12, except that compounds A to E were used respectively instead of compound 5 used as the N-type charge generating layer material. The compounds A to E used at this time are the same as those described in Comparative Examples 1 to 5.

[0339]

[0340] [Evaluation Example 2]

[0341] For the organic electroluminescent devices fabricated in Examples 12 to 22 and Comparative Examples 6 to 10, respectively, the driving voltage and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0342] Sample N-type charge generation layer Driving voltage (V) Current efficiency (cd / A) Example 12 Compound 57.716.7 Example 13 Compound 97.616.8 Example 14 Compound 157.816.5 Example 15 Compound 197.716.5 Example 16 Compound 217.716.7 Example 17 Compound 317.716.6 Example 18 Compound 937.616.5 Example 19 Compound 967.916.7 Example 20 Compound 1297.816.7 Example 21 Compound 1377.816.8 Example 22 Compound 1447.716.8 Comparative Example 6 Compound A8.614.1 Comparative Example 7 Compound B8.514.5 Comparative Example 8 Compound C9.210.1 Comparative Example 9 Compound D9.110.3 Comparative Example 10 Compound E8.614.1

[0343]

[0344] As shown in Table 2 above, the blue organic electroluminescent devices of Examples 12 to 22, which used the compound according to the present invention in the N-type charge generation layer, exhibited superior performance in driving voltage and current efficiency compared to materials in which the phenanthroline moiety is combined with EWG without EDG, materials in which the EDG is connected to a linker or EWG connecting phenanthroline and EWG, and materials that do not contain phenanthroline.

[0345]

[0346] Although embodiments of the present invention have been described above, those skilled in the art will understand that the present invention may be implemented in other specific forms without altering its technical concept or essential features. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. Organic luminescent compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A is any one of the substituents shown in Chemical Formula 2 below, and B is any one of the electron withdrawers (EWGs) shown in Chemical Formula 3 below, and L1 and L2 are each independently an arylene having 6 to 60 carbon atoms or a heteroarylene having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and m and n are each independently integers from 0 to 3, and [Chemical Formula 2] [Chemical Formula 3] In the above Chemical Formulas 2 and 3, * is connected to L1 or L2, and R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 40 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, and each may be unsubstituted or substituted. Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and adjacent substituents may be connected to each other to form a spiro ring or a fused ring, and X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and R is independently hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 5 to 60 nuclei, each of which may be unsubstituted or substituted, and Y is O or S, and The above L1, L2, R1 to R6, Ar1, Ar2, and R are each independently unsubstituted or deuterium, halogen group, cyano group, hydroxyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heterocycloalkyl group having 3 to 20 nuclei, haloalkyl group having 1 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 5 to 30 nuclei, alkylsilyl group having 1 to 20 carbon atoms, arylsilyl group having 6 to 30 carbon atoms, alkylboron group having 1 to 20 carbon atoms, and alkyl of 6 to 30 carbon atoms It can be substituted with one or more substituents selected from the group consisting of an arylborone group, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms.

2. In Paragraph 1, The above L1 and L2 are each independently an arylene having 6 to 30 carbon atoms or a heteroarylene having 5 to 30 nuclei, and each of these may be unsubstituted or substituted, and m is an integer from 0 to 2, and n is an integer from 0 to 3, and The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, and each of these may be unsubstituted or substituted. Ar1 and Ar2 are each independently selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted, and adjacent substituents may be connected to each other to form a spiro ring or a fused ring, and X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and R is each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which may be unsubstituted or substituted, an organic light-emitting compound.

3. In Paragraph 1, The above L1 and L2 are each independently an arylene having 6 to 30 carbon atoms or a heteroarylene having 5 to 30 nuclei, each of which is unsubstituted or a deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, It can be substituted with one or more substituents selected from the group consisting of an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms, and m is 0 or 1, and n is an integer from 0 to 3, and The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei, and these are each unsubstituted or deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, It can be substituted with one or more substituents selected from the group consisting of an alkylboron group having 1 to 20 carbon atoms, an arylboron group having 6 to 30 carbon atoms, an arylphosphine group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 1 to 20 carbon atoms, an arylphosphine oxide group having 6 to 30 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 30 carbon atoms. Ar1 and Ar2 are each independently selected from the group consisting of phenyl groups, naphthyl groups, biphenyl groups, terphenyl groups, anthracenyl groups, naphthasenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, fluorenyl groups, and dibenzofuranyl groups, each of which is unsubstituted or deuterium, halogen groups, cyano groups, hydroxyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, pyridinyl groups, alkenyl groups having 2 to 20 carbon atoms, alkynyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, heterocycloalkyl groups having 3 to 20 nuclei, haloalkyl groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, heteroaryl groups having 5 to 30 nuclei, and 1 to It can be substituted with one or more substituents selected from the group consisting of 20 alkylsilyl groups, 6 to 30 arylsilyl groups, 1 to 20 alkylboron groups, 6 to 30 arylboron groups, 6 to 30 arylphosphine groups, 1 to 20 alkylphosphine oxide groups, 6 to 30 arylphosphine oxide groups, 1 to 20 alkylamine groups, and 6 to 30 arylamine groups, and adjacent substituents can be connected to each other to form a spiro ring or a fused ring. X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and R is each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 30 nuclei, each of which is unsubstituted or deuterium, a halogen group, a cyano group, a hydroxyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 nuclei, a haloalkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 nuclei, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 20 carbon atoms, and 6 to An organic light-emitting compound that can be substituted with one or more substituents selected from the group consisting of 30 arylborone groups, 6 to 30 carbon atom arylphosphine groups, 1 to 20 carbon atom alkylphosphine oxide groups, 6 to 30 carbon atom arylphosphine oxide groups, 1 to 20 carbon atom alkylamine groups, and 6 to 30 carbon atom arylamine groups.

4. In Paragraph 1, The above L1 and L2 are each independently an arylene having 6 to 20 carbon atoms or a heteroarylene having 5 to 20 nuclei, and m is 0 or 1, and n is an integer from 0 to 3, and The above R1 to R6 are each independently selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei. Ar1 and Ar2 are each independently selected from the group consisting of phenyl groups, naphthyl groups, biphenyl groups, and terphenyl groups, and adjacent substituents can be connected to each other to form a spiro ring or a fused ring, and X1 to X3 are each independently N or CR, and at least two of X1 to X3 are N, and An organic light-emitting compound in which R is independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 nuclei.

5. In Paragraph 1, The organic light-emitting compound represented by the above chemical formula 1 is an organic light-emitting compound selected from any one of the following compounds 1 to 214.

6. Anode; cathode; light-emitting layer disposed between the cathode and the anode; and electron transport region disposed between the cathode and the light-emitting layer, comprising The above electron transport region is an organic electroluminescent device comprising an organic light-emitting compound according to claim 1.

7. Anode; cathode; light-emitting layer disposed between the cathode and the anode; and electron transport region and electron transport auxiliary layer disposed between the cathode and the light-emitting layer, comprising The above electron transport region and / or electron transport auxiliary layer comprises an organic electroluminescent device according to claim 1.

8. Anode; cathode; a plurality of light-emitting units disposed between the cathode and the anode; and an N-type charge generating layer and a P-type charge generating layer interposed between adjacent light-emitting units, The above N-type charge generating layer is an organic electroluminescent device comprising an organic light-emitting compound according to claim 1.

9. Use of the organic light-emitting compound according to paragraph 1 in an organic electroluminescent device.

10. In Paragraph 9, An application characterized by the above organic light-emitting compound being used as an electron transport material in the above organic electroluminescent device.

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