Organic light-emitting compound and organic electroluminescent device comprising same

Abstract

Disclosed are a novel organic light-emitting compound having high current efficiency and low driving voltage represented by Formula 1 (see the disclosure), and an organic electroluminescent device comprising the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2023-0171095, filed with the Korean Intellectual Property Office on November 30, 2023, the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] Embodiments of this disclosure relate to novel organic light-emitting compounds and organic electroluminescent devices comprising the organic light-emitting compounds. Background Technology

[0004] Since Bernanose first discovered the luminescence of organic thin films in the 1950s, and in 1965, studies were conducted on organic electroluminescent (EL) devices based on blue electroluminescence using anthracene single crystals. In 1987, Tang proposed an organic electroluminescent device with a stacked structure, which is divided into multiple functional layers, including a hole layer and a light-emitting layer. Since then, organic electroluminescent devices have been developed that incorporate their own characteristic organic layers to impart high efficiency and long lifetime to the devices and the specific materials used in them.

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

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

[0007] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complexes containing heavy atoms such as Ir and Pt. Since these phosphorescent materials can theoretically increase luminescence efficiency by up to four times that of fluorescent materials, extensive research is being conducted on both phosphorescent host materials and phosphorescent dopant materials.

[0008] As shown below, NPB, BCP, Alq3, etc., are currently 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 luminescent layer materials. In particular, among luminescent layer materials, Ir-containing metal complexes such as FIrpic, Ir(ppy)3, and (acac)Ir(btp)2, which have the advantage of improving efficiency, are used as phosphorescent dopants for blue, green, and red light, and 4,4-dicarbazole biphenyl (CBP), as shown below, is used as a phosphorescent host material.

[0009]

[0010] Therefore, although conventional organic layer materials have advantages in terms of light-emitting properties, they cannot satisfactorily improve the lifespan of organic electroluminescent devices due to their low glass transition temperature and the resulting poor thermal stability.

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

[0012] Existing technical documents

[0013] Korean Patent Publication No. 10-2017-0118675 Summary of the Invention

[0014] Technical issues

[0015] Embodiments of this disclosure provide novel compounds with excellent heat resistance, carrier transport capability, luminescence capability, etc., and their uses. These compounds can be used as organic layers in organic electroluminescent devices, specifically as electron transport layer materials and electron transport auxiliary layer materials.

[0016] Embodiments of this disclosure provide an organic electroluminescent device comprising the novel organic light-emitting compound described above, which has low driving voltage, high luminous efficiency, and improved lifetime.

[0017] It should be noted that this disclosure is not limited to the above-mentioned purposes, and other unmentioned purposes of this disclosure will be clearly understood by those skilled in the art from the following description.

[0018] Technical solution

[0019] Embodiments of this disclosure provide organic light-emitting compounds represented by the following formula 1:

[0020] [Formula 1]

[0021]

[0022] In Equation 1,

[0023] Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, at least two of Z1 to Z3 are N, and each of them is unsubstituted or substituted.

[0024] Ar1 and Ar2 are each independently an alkenyl group containing 2 to 40 carbon atoms, an alkynyl group containing 2 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a heterocycloalkyl group containing 2 to 40 carbon atoms, an alkyl group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, an alkoxy group containing 1 to 40 carbon atoms, an aryloxy group containing 6 to 60 carbon atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylboron group containing 1 to 40 carbon atoms, an arylboron group containing 6 to 60 carbon atoms, an arylphosphine group containing 6 to 60 carbon atoms, an oxyarylphosphine group containing 6 to 60 carbon atoms, or an arylamine group containing 6 to 60 carbon atoms, and each of these is unsubstituted or substituted.

[0025] R1 to R3 are each independently an alkyl group containing 1 to 40 carbon atoms or an aryl group containing 6 to 60 carbon atoms, wherein each is unsubstituted or substituted, and wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure.

[0026] L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 30 carbon atoms, and each of them is either unsubstituted or substituted.

[0027] The premise is that L1 and L3 are not both bonded to L2 in adjacent positions.

[0028] Embodiments of this disclosure provide an organic electroluminescent device comprising an organic light-emitting compound.

[0029] Embodiments of this disclosure provide the use of organic light-emitting compounds in organic electroluminescent devices.

[0030] Beneficial effects

[0031] The organic light-emitting compound of this disclosure comprises a heteroaryl ring separated by a terphenyl moiety and a silane-based dibenzo[a] moiety, thereby inducing delocalization of the least unoccupied molecular orbital (LUMO). Based on the ortho-bonding position of the terphenyl moiety, steric hindrance is maximized to increase the triplet energy and exciton confinement on the host side is promoted through the exciton blocking effect. This enhances the efficiency and lifetime of the organic electroluminescent device. At the same time, compared with conventional carbon-based heteroaryl ring moieties, the silane-based dibenzo[a] moiety further provides higher electron-donating properties and improved molecular stability.

[0032] Furthermore, organic electroluminescent devices containing organic light-emitting compounds according to this disclosure can achieve low driving voltage and significantly improved luminescent performance, lifespan, efficiency, etc., thereby being more effectively applied to full-color display panels, etc.

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

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

[0035] The terminology used herein is for illustrative purposes only and should not be construed as limiting the scope of this disclosure. Unless the context clearly indicates otherwise, the singular forms are intended to include the plural forms as well. It will be further understood that the terms “comprising” and / or “including” as used herein do not exclude the presence or addition of one or more other components besides those mentioned.

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

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

[0038] Before proceeding, the meanings of the terms used herein will be briefly described. However, the explanation of the terms is for the purpose of better understanding this disclosure, and the terms should not be construed as limiting the technical ideas of this disclosure unless the context clearly indicates that the terms are used to limit the scope of this disclosure.

[0039] As used herein, the term "aryl group" can refer to a monovalent functional group derived from aromatic hydrocarbons. Aryl groups may include, but are not limited to, phenyl groups, naphthyl groups, anthracene groups, tetraphenyl groups, pyrene groups, tolyl groups, biphenyl groups, terphenyl groups, phenazine groups, spirodifluorenyl groups, fluorenyl groups, peryl groups, indole groups, azulel groups, heptadene groups, phenarenyl groups, phenanthrene groups, etc. Furthermore, the term "arylene group" can refer to a divalent functional group derived from aromatic hydrocarbons.

[0040] As used herein, the term "heteroaryl group" can refer to a monovalent functional group derived from an aromatic heterocycle having a monocyclic or fused-ring structure, and a heteroaryl group may contain at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), or silicon (Si) as a heteroatom in addition to a carbon atom. Specific examples of heteroaryl groups include nitrogen-containing heteroaryl groups, including pyrroleyl groups, pyridinyl groups, pyridazinyl groups, triazinyl groups, pyrimidinyl groups, pyrazinyl groups, triazolyl groups, tetrazolyl groups, benzotriazolyl groups, pyrazolyl groups, imidazole groups, benzimidazole groups, indoleyl groups, isoindoleyl groups, indoleazinyl groups, purine groups, indazole groups, quinolinyl groups, isoquinolinyl groups, quinolinazinyl groups, phthalazinyl groups, naphthidyl groups, quinoxalinyl groups, quinazolinyl groups, quinazolinyl groups, and cinnamic acid groups. The heteroaryl group includes linyl groups, pteridyl groups, imidazotriazinyl groups, acridine groups, phenanthridine groups, carbazole groups, phenanthroline groups, phenazinyl groups, imidazopyridyl groups, imidazopyrimidine groups, pyrazolidine groups, etc.; sulfur-containing heteroaryl groups include thiophene groups, benzothiophene groups, dibenzothiophene groups, benzonaphthothiophene groups, etc.; oxygen-containing heteroaryl groups include furanyl groups, pyranyl groups, benzofuranyl groups, isobenzofuranyl groups, dibenzofuranyl groups, benzonaphthofuranyl groups, etc. Heteroaryl groups can be defined by the number of nucleoatomic atoms rather than the number of carbon atoms. Here, the number of nucleoatomic atoms can refer to the total number of atoms containing one or more heteroatoms other than carbon (C), which are selected from nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the number of nucleoatomic atoms in heteroaryl groups and heteroarylene groups can be 5 to 60, 5 to 30, or 5 to 20.

[0041] As used herein, the term "alkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon having a linear or branched structure. Alkyl groups may include, but are not limited to, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, n-pentyl groups, 1,1-dimethylpropyl groups, 1,2-dimethylpropyl groups, 2,2-dimethylpropyl groups, 1-ethylpropyl groups, 2-ethylpropyl groups, n-hexyl groups, 1-methyl-2-ethylpropyl groups, 1-ethyl-2-methylpropyl groups, 1,1,2-trimethylpropyl groups, 1-propylpropyl groups, 1-methylbutyl groups, 2-methylbutyl groups, 1,1-dimethylbutyl groups, 1,2-dimethylbutyl groups, 2,2-dimethylbutyl groups, 1,3-dimethylbutyl groups, 2,3-dimethylbutyl groups, 2-ethylbutyl groups, 2-methylpentyl groups, 3-methylpentyl groups, or similar groups.

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

[0043] As used herein, the term "alkenyl group" may refer to a monovalent functional group derived from a hydrocarbon, wherein the alkyl group of the hydrocarbon contains one or more carbon-carbon double bonds at its center or end.

[0044] As used herein, the term "alkynyl group" may refer to a monovalent functional group derived from a hydrocarbon, wherein the alkyl group of the hydrocarbon contains one or more carbon-carbon triple bonds at its center or end.

[0045] As used herein, the term "heterocyclic alkyl group" may refer to a monovalent functional group derived from a saturated hydrocarbon having a cyclic structure, wherein the heterocyclic alkyl group may contain at least one heteroatom selected from nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), or silicon (Si) in addition to a carbon atom. A heterocyclic alkyl group may be defined by the number of nucleomeric atoms rather than the number of carbon atoms. Here, the number of nucleomeric atoms may refer to the total number of atoms containing one or more heteroatoms other than a carbon (C) atom, selected from nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si). For example, the number of nucleomeric atoms in a heterocyclic alkyl group may be 5 to 60, 5 to 30, or 5 to 20.

[0046] As used herein, "alkoxy group" and "aryloxy group" can both refer to monovalent functional groups derived from compounds, wherein the oxygen atom is additionally contained at the bonding site of the linker to the aforementioned alkyl or aryl group.

[0047] As used herein, "alkylsilyl group" and "arylsilyl group" can both refer to monovalent functional groups derived from compounds, wherein at least one hydrogen atom on a silane is replaced by the aforementioned alkyl or aryl group, respectively.

[0048] As used herein, the terms “alkylboronyl group” and “arylboronyl group” refer to monovalent functional groups derived from compounds in which at least one hydrogen atom of a borane is replaced by the aforementioned alkyl or aryl group, respectively.

[0049] As used herein, the terms “arylphosphine group” and “oxyarylphosphine group” refer to monovalent functional groups derived from compounds in which the oxides and phosphine oxides are respectively replaced by the aforementioned aryl groups.

[0050] As used herein, the term "arylamine group" refers to a monovalent functional group derived from a compound in which at least one hydrogen atom of ammonia is replaced by the aforementioned aryl group.

[0051] As used herein, the term "substitution" refers to substitution with at least one substituent selected from: deuterium, an alkenyl group containing 2 to 20 carbon atoms, an alkynyl group containing 2 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a heterocyclic alkyl group containing 2 to 20 carbon atoms, a heterocyclic alkyl group containing 5 to 20 nucleomeric atoms, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a group containing 5 to 30 nucleomeric atoms. The substituents include: heteroaryl groups with a nuclear atom; alkoxy groups containing 1 to 20 carbon atoms; aryloxy groups containing 6 to 30 carbon atoms; alkylsilyl groups containing 1 to 20 carbon atoms; arylsilyl groups containing 6 to 30 carbon atoms; alkylboryl groups having 1 to 20 carbon atoms; arylboryl groups having 6 to 30 carbon atoms; arylphosphinyl groups having 6 to 30 carbon atoms; oxyarylphosphinyl groups having 6 to 30 carbon atoms; or arylamine groups having 6 to 30 carbon atoms. In the substitution of multiple substituents, these substituents may be the same or different.

[0052] <Organic luminescent compounds>

[0053] This disclosure provides novel organic light-emitting compounds. The organic light-emitting compounds are represented by the following formula 1:

[0054] [Formula 1]

[0055]

[0056] In Equation 1,

[0057] Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, at least two of Z1 to Z3 are N, and each of them is unsubstituted or substituted.

[0058] Ar1 and Ar2 are each independently an alkenyl group containing 2 to 40 carbon atoms, an alkynyl group containing 2 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a heterocyclic alkyl group containing 2 to 40 carbon atoms, a heterocyclic alkyl group containing 5 to 40 nucleomeric atoms, an alkyl group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, a heteroaryl group containing 5 to 60 nucleomeric atoms, and a group containing 1 to 40 carbon atoms. An alkoxy group containing 1 carbon atom, an aryloxy group containing 6 to 60 carbon atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylboron group containing 1 to 40 carbon atoms, an arylboron group containing 6 to 60 carbon atoms, an arylphosphine group containing 6 to 60 carbon atoms, an oxyarylphosphine group containing 6 to 60 carbon atoms, or an arylamine group containing 6 to 60 carbon atoms, and each of these groups is unsubstituted or substituted.

[0059] R1 to R3 are each independently an alkyl group containing 1 to 40 carbon atoms or an aryl group containing 6 to 60 carbon atoms, wherein each is unsubstituted or substituted, and wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure.

[0060] L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 30 carbon atoms, and each of them is either unsubstituted or substituted.

[0061] The premise is that L1 and L3 are not both bonded to L2 in adjacent positions.

[0062] Specifically, at least one of the following groups, represented as R, Ar1, Ar2, R1 to R3 and L, is independently unsubstituted or substituted by at least one substituent selected from: deuterium, an alkenyl group containing 2 to 20 carbon atoms, an alkynyl group containing 2 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, a group containing 5 to 20 carbon atoms, an alkenyl group containing 2 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, a group containing 5 to 20 carbon atoms, or an arylamine group. The substituents include: heterocyclic alkyl groups with one nucleomeric atom; alkyl groups containing 1 to 20 carbon atoms; aryl groups containing 6 to 30 carbon atoms; heteroaryl groups containing 2 to 30 carbon atoms; heteroaryl groups containing 5 to 30 nucleomeric atoms; alkoxy groups containing 1 to 20 carbon atoms; aryloxy groups containing 6 to 30 carbon atoms; alkylsilyl groups containing 1 to 20 carbon atoms; arylsilyl groups containing 6 to 30 carbon atoms; alkylboryl groups having 1 to 20 carbon atoms; arylboryl groups having 6 to 30 carbon atoms; arylphosphinyl groups having 6 to 30 carbon atoms; oxyarylphosphinyl groups having 6 to 30 carbon atoms; or arylamine groups having 6 to 30 carbon atoms. In the substitution of multiple substituents, these substituents may be the same as or different from each other.

[0063] In one implementation, in Equation 1,

[0064] Z1 to Z3 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 20 carbon atoms, and at least two of Z1 to Z3 are N.

[0065] Ar1 and Ar2 are each independently an alkenyl group containing 2 to 20 carbon atoms, an alkynyl group containing 2 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a heterocyclic alkyl group containing 2 to 20 carbon atoms, a heterocyclic alkyl group containing 5 to 20 nucleomeric atoms, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nucleomeric atoms. Groups, including alkoxy groups containing 1 to 20 carbon atoms, aryloxy groups containing 6 to 30 carbon atoms, alkylsilyl groups containing 1 to 20 carbon atoms, arylsilyl groups containing 6 to 30 carbon atoms, alkylboron groups containing 1 to 20 carbon atoms, arylboron groups containing 6 to 30 carbon atoms, arylphosphine groups containing 6 to 30 carbon atoms, oxyarylphosphine groups containing 6 to 30 carbon atoms, or arylamine groups containing 6 to 30 carbon atoms.

[0066] R1 to R3 are each independently an alkyl group containing 1 to 20 carbon atoms or an aryl group containing 6 to 30 carbon atoms, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure (for example, in the case of an aryl group, a fused ring structure can be formed with an adjacent aryl group), and

[0067] L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 20 carbon atoms.

[0068] Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

[0069] In one implementation, in Equation 1,

[0070] Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N.

[0071] Ar1 and Ar2 are each independently an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, or a heteroaryl group containing 5 to 30 nuclear atoms.

[0072] R1 to R3 are each independently an alkyl group containing 1 to 10 carbon atoms or an aryl group containing 6 to 20 carbon atoms, and at least one of R1 and R3 is an aryl group having 2 to 20 carbon atoms, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure (e.g., in the case of an aryl group, a fused ring structure can be formed with an adjacent aryl group), and

[0073] L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 20 carbon atoms.

[0074] Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

[0075] In one implementation, in Equation 1,

[0076] Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N.

[0077] Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, or a dibenzo[a] group.

[0078] R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group, or a naphthyl group, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure (for example, a phenyl group, a biphenyl group, and a naphthyl group can form a fused ring structure with adjacent phenyl groups, biphenyl groups, or naphthyl groups, respectively), and

[0079] L by This indicates that L1 to L3 are each independently a phenylene group, a biphenyl group, or a naphthyl group.

[0080] Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

[0081] In one implementation, L can be represented by any one of the following formulas L-1 to L-7.

[0082] [Formula L-1]

[0083]

[0084] [Formula L-2]

[0085]

[0086] [Formula L-3]

[0087]

[0088] [Formula L-4]

[0089]

[0090] [Formula L-5]

[0091]

[0092] [Formula L-6]

[0093]

[0094] [Formula L-7]

[0095]

[0096] In each of equations L-1 to L-7, This indicates the bonding site with Equation 1.

[0097] In one implementation, in Equation 1,

[0098] Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N.

[0099] Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, or a naphthyl group.

[0100] R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group, or a naphthyl group, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure (for example, a phenyl group, a biphenyl group, and a naphthyl group can form a fused ring structure with adjacent phenyl groups, biphenyl groups, or naphthyl groups, respectively), and

[0101] L is represented by the following formulas: L-1, L-2, L-6, or L-7.

[0102] [Formula L-1]

[0103]

[0104] [Formula L-2]

[0105]

[0106] [Formula L-6]

[0107]

[0108] [Formula L-7]

[0109]

[0110] In each of equations L-1, L-2, L-6, or L-7, This indicates the bonding site with Equation 1.

[0111] In one implementation, Equation 1 may be represented by any one of Equations 2 through 5 below.

[0112] [Equation 2]

[0113]

[0114] [Formula 3]

[0115]

[0116] [Formula 4]

[0117]

[0118] [Formula 5]

[0119]

[0120] In each of Equations 2 to 5,

[0121] Ar1 and Ar2 are each independently a phenyl group or a biphenyl group, and

[0122] R1 to R3 are each independently a methyl group, a phenyl group, or a biphenyl group, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure (for example, a phenyl group and a biphenyl group can form a fused ring structure with adjacent phenyl groups and biphenyl groups, respectively).

[0123] In one embodiment, the organic light-emitting compound represented by Formula 1 may be any one selected from compounds 1 to 180.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] As a specific example, the compound represented by Formula 1 may be any one of compounds 1, 21, 27, 43, 46, 61, 81, 87, 103, 106, 121, 141, 147, 163 and 166.

[0148] The novel organic light-emitting compound disclosed herein comprises a heteroaromatic moiety and a silane-based dibenzo[a] moiety, separated by a terphenyl moiety, thereby inducing delocalization of the lowest unoccupied molecular orbital (LUMO). Furthermore, steric hindrance is maximized according to the ortho-bonding position of the terphenyl moiety, thereby increasing the triplet energy and promoting exciton confinement on the host side. This can enhance the device efficiency and lifetime of organic electroluminescent devices through exciton blocking effects. Moreover, compared to conventional carbon-based heteroaromatic ring moieties, the silane-based dibenzo[a] moiety offers superior electron-donating properties and improved molecular stability.

[0149] Furthermore, by using the novel organic light-emitting compounds disclosed herein as materials for the electron transport layer, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0150] Organic electroluminescent devices

[0151] This disclosure provides an organic electroluminescent device containing the novel organic light-emitting compound described above. The organic light-emitting compound according to this disclosure can be incorporated into at least one organic material layer disposed between the cathode and anode of the organic electroluminescent device.

[0152] In one embodiment, the organic electroluminescent device includes an anode, a cathode, a light-emitting layer disposed between the cathode and the anode, and an electron transport region disposed between the cathode and the light-emitting layer, wherein the electron transport region contains an organic light-emitting compound according to the present disclosure.

[0153] anode

[0154] The organic electroluminescent device disclosed herein includes an anode. The anode is used to inject holes into an organic layer. Here, the organic layer may mean at least one layer formed between the anode and the cathode.

[0155] There are no particular limitations on the type of anode material, and it can be prepared according to conventional methods known in the art. Anode materials may include, for example, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); 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, or polyaniline; or carbon black. These compounds may be used alone or in combination of two or more of them.

[0156] There are no particular limitations on the method for preparing the anode, and it can be prepared according to conventional methods known in the art. For example, the anode can be formed by coating an anode material onto a substrate such as a silicon wafer, quartz, glass plate, metal plate, or plastic film.

[0157] cathode

[0158] The organic electroluminescent device disclosed herein includes a cathode. The cathode is used to inject electrons into an organic layer.

[0159] There are no particular limitations on the type of cathode material used to constitute the cathode, and it can be prepared according to conventional methods known in the art. Cathode materials include, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; or multilayer materials such as LiF / Al or LiO2 / Al.

[0160] Emissive layer

[0161] The organic electroluminescent device disclosed herein includes a light-emitting layer disposed between a cathode and an anode. The light-emitting layer is a layer in which holes and electrons combine to form excitons, and the color of the light emitted by the organic electroluminescent device can vary depending on the material constituting the light-emitting layer.

[0162] The luminescent material constituting the luminescent layer can be selected from a variety of commercially available materials without particular limitation, depending on the desired emission wavelength of the light.

[0163] In one embodiment, the luminescent material can be categorized into blue, green, and red luminescent materials, etc., based on the color of the emitted light. The luminescent layer can be formed as a combination of a host material and dopants to prevent problems such as deterioration in color purity or reduced device efficiency due to light emission attenuation. Using a host material as the main component of the luminescent layer and a small amount of dopants with a band gap smaller than that of the host material can improve the luminous efficiency of the organic electroluminescent device.

[0164] Electronic transmission area

[0165] The organic electroluminescent device disclosed herein includes an electron transport region disposed between the light-emitting layer and the cathode.

[0166] An electron transport region is used to move electrons injected from the cathode to the light-emitting layer. Such an electron transport region may include at least one selected from the electron injection layer or the electron transport layer. In this case, considering the characteristics of organic electroluminescent devices, the organic electroluminescent device preferably includes both the electron transport layer and the electron injection layer described above.

[0167] In the electron transport region, the electron injection layer can be formed of any electron injection material that promotes electron injection from the cathode and has high electron mobility. Non-limiting examples of useful electron injection materials include the aforementioned amphiphilic compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. As specific examples, electron injection materials include at least one selected from: lanthanides such as LiF, Li₂O, BaO, NaCl, CsF, and Yb; and metal halides such as RbCl and RbI.

[0168] The electron transport region may contain the organic light-emitting compound according to the present disclosure described above. The organic light-emitting compound according to the present disclosure comprises a heteroaryl ring moiety separated by a terphenyl moiety and a silane-based dibenzo[a] moiety, thereby inducing delocalization of the lowest unoccupied molecular orbital (LUMO). Furthermore, based on the ortho-bonding position of the terphenyl moiety, steric hindrance is maximized to increase the triplet energy and exciton confinement on the host side is promoted through exciton blocking effects. This enhances the efficiency and lifetime of the organic electroluminescent device. Simultaneously, compared to conventional carbon-based heteroaryl ring moieties, the silane-based dibenzo[a] moiety further provides higher electron-donating properties and improved molecular stability. Moreover, by using the novel organic light-emitting compound according to the present disclosure as a material for the electron transport layer, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0169] An electron transport layer can be formed by mixing the organic light-emitting compound according to this disclosure with lithium quinoline (Liq). Liq has a conduction band of 5.58 eV and a valence band of 3.153 eV, which helps to lower the potential barrier.

[0170] The electron transport region can be prepared according to conventional methods known in the art. Methods for forming the electron transport region may include, for example, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser-induced thermal imaging (LITI), but are not limited thereto.

[0171] Electron transport auxiliary layer

[0172] The organic light-emitting element disclosed herein may include an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region. The electron transport auxiliary layer prevents excitons or holes generated in the light-emitting layer from diffusing into the electron transport region.

[0173] The electron transport auxiliary layer may comprise the organic light-emitting compound according to the present disclosure described above. The organic light-emitting compound according to the present disclosure comprises a heteroaryl ring moiety separated by a terphenyl moiety and a silane-based dibenzo[a] moiety, thereby inducing delocalization of the lowest unoccupied molecular orbital (LUMO). Furthermore, based on the ortho-bonding position of the terphenyl moiety, steric hindrance is maximized to increase the triplet energy and exciton confinement on the host side is promoted through exciton blocking effects. This enhances the efficiency and lifetime of the organic electroluminescent device. Simultaneously, compared to conventional carbon-based heteroaryl ring moieties, the silane-based dibenzo[a] moiety further provides higher electron-donating properties and improved molecular stability. Moreover, by using the novel organic light-emitting compound according to the present disclosure as the material for the electron transport auxiliary layer, excellent performance can be achieved in terms of driving voltage, EL peak, and current efficiency.

[0174] The electron transport auxiliary region can be formed according to conventional methods known in the art, such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser-induced thermal imaging (LITI), but is not limited thereto.

[0175] Hole transport region

[0176] The organic electroluminescent device disclosed herein includes a hole transport region disposed between an anode and a light-emitting layer. The hole transport region is used to move holes injected by the anode to the light-emitting layer.

[0177] The hole transport region may include at least one selected from the hole injection layer or the hole transport layer. In this case, considering the characteristics of the organic electroluminescent device, the organic electroluminescent device preferably includes both the hole transport layer and the hole injection layer.

[0178] Any material can be used for both the hole injection layer and the hole transport layer, provided it has a low hole injection barrier and a high hole mobility, without particular limitation. It can be selected from hole injection and hole transport materials used in the art without restriction. The materials constituting the hole injection layer and the materials constituting the hole transport layer can be the same or different from each other.

[0179] The hole injection material can be selected from hole injection materials known in the art without limitation. Non-limiting examples of useful hole injection materials include phthalocyanine compounds, such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine), TDATA (4,4'4"-tris(N,N-diphenylamino)triphenylamine), TDATA (4,4',4"-tri{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrenesulfonate)), etc. These compounds can be used alone or in combination of two or more thereof.

[0180] Furthermore, hole transport materials can be selected from hole transport materials known in the art without limitation. Non-limiting examples of useful hole transport materials include: carbazole derivatives, such as phenylcarbazole and polyvinylcarbazole; fluorene-based derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine); NPB (N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-cyclohexamethylenebis[N,N-bis(4-methylphenyl)aniline]), etc. These compounds can be used alone or in combination of two or more of them.

[0181] Hole transport materials can be formed using conventional methods known in the art, such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser-induced thermal imaging (LITI), but are not limited thereto.

[0182] Hole transport auxiliary layer

[0183] The organic electroluminescent device according to this disclosure may further include a light-emitting auxiliary layer disposed between the hole transport region and the light-emitting layer. The light-emitting auxiliary layer is used to control the thickness of the organic layer while transporting holes from the hole transport region to the light-emitting layer. The light-emitting auxiliary layer prevents electrons from moving to the hole transport layer based on its higher LUMO and prevents excitons from moving from the light-emitting layer to the hole transport layer based on its higher triplet (T1) energy level.

[0184] The light-emitting auxiliary layer may include a hole transport material and may be formed of the same material as the hole transport region. Furthermore, the light-emitting auxiliary layers of red, green, and blue organic electroluminescent devices may be formed of the same material as each other.

[0185] The material of the light-emitting auxiliary layer is not particularly limited, and may be, for example, a carbazole derivative, an arylamine derivative, or a carbazole-arylamine derivative. Furthermore, in addition to the materials described above, the light-emitting auxiliary layer may selectively contain a p-type dopant. The p-type dopant may be any p-type dopant commonly used in the art.

[0186] Cover layer

[0187] The organic electroluminescent device disclosed herein may further include a capping layer disposed on the cathode. The capping layer serves to protect the electroluminescent device and promote the efficient emission of light generated in the organic layer to the outside.

[0188] The covering material constituting the covering layer may include, for example, at least one selected from the group consisting of: aluminum tri-8-hydroxyquinoline (Alq3), ZnSe, 2,5-bis(6'-(2',2''-bipyridine))-1,1-dimethyl-3,4-diphenylsilanecyclopentadiene, 4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), and 1,1'-bis(di-4-toluamidephenyl)cyclohexane (TAPC), but is not limited thereto.

[0189] The covering layer may be a single layer, or it may include two or more layers with different refractive indices, so that the refractive index of light passing through the two or more layers changes gradually.

[0190] The capping layer can be formed according to conventional methods known in the art, and the methods can be selected from a variety of methods such as vacuum deposition, spin coating, casting and LB (Langmuir-Blodgett).

[0191] This disclosure provides the use of the above-mentioned organic light-emitting compounds in organic electroluminescent devices. The organic light-emitting compounds impart significantly improved luminescent performance, driving voltage, lifetime, and efficiency to organic electroluminescent devices.

[0192] In one embodiment, the organic light-emitting compound can be used as an electron transport material in an organic electroluminescent device.

[0193] In one embodiment, when the organic light-emitting compound is used as an electron transport material in an organic electroluminescent device, it can be used as a material for the electron transport region.

[0194] In one embodiment, the organic light-emitting compound can be used as a material for an electron transport layer and / or an electron transport auxiliary layer in an organic electroluminescent device.

[0195] The present disclosure will now be described with reference to specific examples. However, the examples provided are merely for illustrative purposes and should not be construed as limiting the scope of the disclosure.

[0196] [ Preparation Examples ]

[0197] [Preparation Example 1]: Synthesis of SC-1

[0198]

[0199] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were reacted with a mixture of 160 mL dioxane and 40 mL water under heating and reflux with stirring for 3 h. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-1 (9.2 g, 60% yield).

[0200] 1H-NMR: δ 8.36 (d, 4H), 7.96 (d, 2H), 7.71 (d, 1H), 7.61~7.60 (m, 3H), 7.50 (t, 6H), 7.38 (t, 2H), 7.25 (d, 4H)

[0201] Mass: [(M+H)] + ]:497

[0202] [Preparation Example 2]: Synthesis of SC-2

[0203]

[0204] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were reacted with a mixture of 160 mL dioxane and 40 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-2 (8.9 g, 58% yield).

[0205] 1H-NMR: δ 8.36 (d, 4H), 8.10 (d, 2H), 7.96-7.94 (m, 3H), 7.73 (t, 1H), 7.62-7.50 (m, 12H)

[0206] Mass: [(M+H)] + ]:497

[0207] [Preparation Example 3]: Synthesis of SC-3

[0208]

[0209] 2-([1,1'-biphenyl]-3-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were reacted with a mixture of 160 mL dioxane and 40 mL water under heating and reflux with stirring for 3 h. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-3 (8.7 g, 59% yield).

[0210] 1H-NMR: δ 8.38 (d, 1H), 8.36 (d, 2H), 8.10 (d, 2H), 7.96-7.94 (m, 4H), 7.75-7.73 (m, 4H), 7.62-7.60 (m, 7H), 7.50-7.41 (m, 6H)

[0211] Mass: [(M+H)] + ]:573

[0212] [Preparation Example 4]: Synthesis of SC-4

[0213]

[0214] 2-(5-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were reacted with a mixture of 160 mL dioxane and 40 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-4 (8.2 g, 55% yield).

[0215] 1H-NMR: δ 8.36 (d, 4H), 8.04 (s, 1H), 7.75-7.71 (m, 3H), 7.61 (d, 1H), 7.50-7.38 (m, 11H), 7.25 (d, 4H)

[0216] Mass: [(M+H)] + ]:573

[0217] [Preparation Example 5]: Synthesis of SC-5

[0218]

[0219] 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenylpyrimidine (12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were reacted with a mixture of 160 mL dioxane and 40 mL water under heating and reflux with stirring for 3 h. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-5 (8.3 g, 56% yield).

[0220] 1H-NMR: δ 8.23 ​​(s, 1H), 7.96-7.94 (m, 7H), 7.75-7.71 (m, 5H), 7.61-7.38 (m, 12H), 7.25 (2H)

[0221] Mass: [(M+H)] + ]:572

[0222] [Synthesis Example]

[0223] [Synthetic Example 1]: Synthesis of Compound 1

[0224]

[0225] Compound SC-1 (5.0 g, 10.1 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), synthesized by the method of Example 1, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (3.1 g, 38% yield).

[0226] Mass: [(M+H)] + ]:797

[0227] [Synthetic Example 2]: Synthesis of Compound 21

[0228]

[0229] SC-2 (5.0 g, 10.1 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), synthesized by the method in Example 2, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 21 (3.1 g, 39% yield).

[0230] Mass: [(M+H)] + ]:797

[0231] [Synthetic Example 3]: Synthesis of Compound 27

[0232]

[0233] Compound SC-3 (5.0 g, 8.7 mmol), synthesized by the method in Example 3, along with (3-([1,1'-biphenyl]-3-yldiphenylsilyl)phenyl)boronic acid (4.0 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 27 (3.4 g, 41% yield).

[0234] Mass: [(M+H)] + ]:949

[0235] [Synthetic Example 4]: Synthesis of Compound 43

[0236]

[0237] Compound SC-4 (5.0 g, 8.7 mmol), (4-(triphenylsilyl)phenyl)boronic acid (3.3 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), synthesized by the method in Example 4, was reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 43 (3.1 g, 40% yield).

[0238] Mass: [(M+H)] + ]:873

[0239] [Synthetic Example 5]: Synthesis of Compound 46

[0240]

[0241] Compound SC-5 (5.0 g, 8.8 mmol), (4-(triphenylsilyl)phenyl)boronic acid (3.3 g, 8.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), synthesized by the method in Example 5, was reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 46 (3.0 g, 39% yield).

[0242] Mass: [(M+H)] + ]:872

[0243] [Synthetic Example 6]: Synthesis of Compound 61

[0244]

[0245] Compound SC-1 (5.0 g, 10.1 mmol), (3-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), synthesized by the method of Example 1, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 61 (2.6 g, 38% yield).

[0246] Mass: [(M+H)] + ]:673

[0247] [Synthetic Example 7]: Synthesis of Compound 81

[0248]

[0249] Compound SC-2 (5.0 g, 10.1 mmol), (3-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), synthesized by the method in Example 2, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 81 (2.8 g, 41% yield).

[0250] Mass: [(M+H)] + ]:673

[0251] [Synthetic Example 8]: Synthesis of Compound 87

[0252]

[0253] Compound SC-3 (5.0 g, 10.1 mmol), synthesized by the method in Example 3, along with (3-([1,1'-biphenyl]-3-yldimethylsilyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc) (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs₂CO₃ (5.7 g, 17.5 mmol), were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 87 (2.9 g, 40% yield).

[0254] Mass: [(M+H)] + ]:825

[0255] [Synthetic Example 9]: Synthesis of Compound 103

[0256]

[0257] Compound SC-4 (5.0 g, 10.1 mmol), (4-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), synthesized by the method in Example 4, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 103 (2.5 g, 38% yield).

[0258] Mass: [(M+H)] + ]:749

[0259] [Synthetic Example 10]: Synthesis of Compound 106

[0260]

[0261] Compound SC-5 (5.0 g, 10.1 mmol), (4-(dimethyl(phenyl)silyl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), synthesized by the method in Example 5, were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 106 (2.8 g, 42% yield).

[0262] Mass: [(M+H)] + ]:748

[0263] [Synthetic Example 11]: Synthesis of Compound 121

[0264]

[0265] Compound SC-1 (5.0 g, 10.1 mmol), synthesized by the method in Example 1, along with (5,5-diphenyl-5H-dibenzo[b,d]siloxane-1-yl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 121 (3.2 g, 40% yield).

[0266] Mass: [(M+H)] + ]:795

[0267] [Synthetic Example 12]: Synthesis of Compound 141

[0268]

[0269] Compound SC-2 (5.0 g, 10.1 mmol), synthesized by the method in Example 2, along with (5,5-diphenyl-5H-dibenzo[b,d]siloxane-3-yl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol), were reacted with stirring under heating and reflux for 3 hours in the presence of a mixed solvent of 80 mL dioxane and 20 mL water. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 141 (3.1 g, 39% yield).

[0270] Mass: [(M+H)] + ]:795

[0271] [Synthetic Example 13]: Synthesis of Compound 147

[0272]

[0273] Compound SC-3 (5.0 g, 10.1 mmol), synthesized by the method in Example 3, along with (3-(5-diphenyl-5H-dibenzo[b,d]siloxane-5-yl)phenyl)boronic acid (3.8 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), were reacted with stirring under heating and reflux for 3 hours in the presence of a mixed solvent of 80 mL dioxane and 20 mL water. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 147 (3.1 g, 41% yield).

[0274] Mass: [(M+H)] + ]:871

[0275] [Synthetic Example 14]: Synthesis of Compound 163

[0276]

[0277] Compound SC-4 (5.0 g, 8.7 mmol), synthesized by the method in Example 4, along with (5,5-diphenyl-5H-dibenzo[b,d]siloxane-2-yl)boronic acid (3.8 g, 8.7 mmol), Pd(OAc) (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs₂CO₃ (5.7 g, 17.5 mmol), were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 163 (3.1 g, 41% yield).

[0278] Mass: [(M+H)] + ]:871

[0279] [Synthetic Example 15]: Synthesis of Compound 166

[0280]

[0281] Compound SC-5 (5.0 g, 8.8 mmol), synthesized by the method in Example 5, along with 5,5'-spirobis[dibenzo[b,d]siloxane-2-ylboronic acid (3.3 g, 8.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol), were reacted with a mixture of 80 mL dioxane and 20 mL water under heating and reflux with stirring for 3 hours. After the reaction was complete, the mixture was quenched with sufficient water, and the resulting solid was filtered to remove the solution and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 166 (2.9 g, 38% yield).

[0282] Mass: [(M+H)] + ]:868

[0283] [Example and Comparative Example]

[0284] [Examples 1 to 15 and Comparative Examples 1 to 7] Fabrication of a Blue Organic Electroluminescent Device

[0285] The compounds synthesized in the synthesis examples were purified to high purity by sublimation using common methods, and then a blue organic electroluminescent device was fabricated according to the following procedure.

[0286] First, indium tin oxide (ITO) is coated to a thickness of 1200 μm. The glass substrate was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, or methanol, then dried, and subjected to UV cleaning for 5 minutes using a Power Sonic 405 (Hwashin Tech) to fabricate a substrate with an ITO transparent electrode. The fabricated substrate was then transferred to a vacuum evaporator.

[0287] An organic electroluminescent device is fabricated by sequentially laminating a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode onto an ITO transparent electrode (anode) prepared as described above. Specifically, the hole injection layer is formed by co-depositing HI and HAT-CN at a weight ratio of 98:2 to a thickness of 6 to 10 nm on the anode; the hole transport layer is formed by depositing compound HI to a thickness of 140 nm on the hole injection layer; the light-emitting auxiliary layer is formed by depositing EB to a thickness of 5 nm on the hole transport layer; the light-emitting layer is formed by co-depositing BH and BD at a weight ratio of 98:2 to a thickness of 20 nm on the light-emitting auxiliary layer; the electron transport layer is formed by co-depositing electron transport layer material and Liq at a weight ratio of 1:1 to a thickness of 30 nm on the light-emitting layer; the electron injection layer is formed by depositing LiF to a thickness of 1 nm on the electron transport layer; and the cathode is formed by depositing Al to a thickness of 100 nm on the electron injection layer. Table 1 below shows the structures of HI, HAT-CN6, EB, BH, BD and Liq, and Table 2 below shows the materials used for the electron transport layer.

[0288] [Table 1]

[0289]

[0290] [Table 2]

[0291]

[0292]

[0293] [Examples 16 to 30 and Comparative Examples 8 to 14] Fabrication of a Blue Organic Electroluminescent Device

[0294] The compounds synthesized in the synthesis examples were purified to high purity by sublimation using common methods, and then a blue organic electroluminescent device was fabricated according to the following procedure.

[0295] First, indium tin oxide (ITO) is coated to a thickness of 1200. The glass substrate was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, or methanol, then dried, and subjected to UV cleaning for 5 minutes using a Power Sonic 405 (Hwashin Tech) to fabricate a substrate with an ITO transparent electrode. The fabricated substrate was then transferred to a vacuum evaporator.

[0296] An organic electroluminescent device is fabricated by sequentially laminating a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode onto an ITO transparent electrode (anode) of a substrate prepared as described above. Specifically, the hole injection layer is formed by co-depositing HI and HAT-CN at a weight ratio of 98:2 to a thickness of 6 to 10 nm on the anode; the hole transport layer is formed by depositing compound HI on the hole injection layer to a thickness of 140 nm; the luminescent auxiliary layer is formed by depositing EB on the hole transport layer to a thickness of 5 nm; the luminescent layer is formed by co-depositing BH and BD on the luminescent auxiliary layer at a weight ratio of 98:2 to a thickness of 20 nm; the electron transport auxiliary layer is formed by depositing a material for the electron luminescent auxiliary layer on the luminescent layer to a thickness of 5 nm; the electron transport layer is formed by co-depositing ET and Liq on the electron transport auxiliary layer at a weight ratio of 1:1 to a thickness of 30 nm; the electron injection layer is formed by depositing LiF on the electron transport layer to a thickness of 1 nm; and the cathode is formed by depositing Al on the electron injection layer to a thickness of 100 nm. Table 3 below shows the structure of ET, and Table 4 below shows the materials used for the electron transport auxiliary layer.

[0297] [Table 3]

[0298]

[0299] [Table 4]

[0300]

[0301]

[0302] [Experimental Examples]

[0303] [Experimental Example 1] Evaluation of the performance of the blue organic electroluminescent devices of Examples 1 to 15 and Comparative Examples 1 to 7

[0304] At 10 mA / cm 2 At a current density, the driving voltage, EL peak, and current efficiency of the organic electroluminescent devices fabricated in Examples 1 to 15 and Comparative Examples 1 to 7 were measured, and the results are shown in Table 5 below.

[0305] [Table 5]

[0306]

[0307] As can be seen from Table 5, the blue organic electroluminescent devices manufactured in Examples 1 to 15 exhibit superior overall results compared to the organic electroluminescent devices manufactured in Comparative Examples 1 to 7 in terms of driving voltage, EL peak, and current efficiency.

[0308] [Experimental Example 2] Evaluation of the performance of the blue organic electroluminescent devices of Examples 16 to 30 and Comparative Examples 8 to 14

[0309] At 10 mA / cm 2 At a current density, the driving voltage, EL peak, and current efficiency of the organic electroluminescent devices fabricated in Examples 16 to 30 and Comparative Examples 8 to 14 were measured, and the results are shown in Table 6 below.

[0310] [Table 6]

[0311]

[0312] As can be seen from Table 6, the blue organic electroluminescent devices prepared in Examples 16 to 30 showed better overall results in terms of driving voltage, EL peak and current efficiency compared with the organic electroluminescent devices prepared in Comparative Examples 8 to 14.

[0313] Specifically, referring to Tables 5 and 6, even compared to the comparative examples using SP-3 to SP-6 (which have different ortho-bonding positions in the structure of the organic light-emitting compounds according to the invention), the device exhibits superior overall performance in the evaluation of driving voltage, EL peak, and current efficiency.

[0314] Although embodiments of this disclosure have been disclosed, those skilled in the art will understand that various modifications, additions, and substitutions can be made without departing from the scope and spirit of this disclosure. Therefore, it is clear that the above exemplary embodiments are illustrative in all respects and do not limit this disclosure.

Claims

1. An organic light-emitting compound, represented by the following formula 1: [Formula 1] ; in, In Equation 1, Z1 to Z3 are each independently N or CR, wherein R is hydrogen, an alkyl group containing 1 to 30 carbon atoms, or an aryl group containing 6 to 60 carbon atoms, at least two of Z1 to Z3 are N, and each of them is unsubstituted or substituted. Ar1 and Ar2 are each independently an alkenyl group containing 2 to 40 carbon atoms, an alkynyl group containing 2 to 40 carbon atoms, a cycloalkyl group containing 3 to 40 carbon atoms, a heterocycloalkyl group containing 2 to 40 carbon atoms, an alkyl group containing 1 to 40 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, an alkoxy group containing 1 to 40 carbon atoms, an aryloxy group containing 6 to 60 carbon atoms, an alkylsilyl group containing 1 to 40 carbon atoms, an arylsilyl group containing 6 to 60 carbon atoms, an alkylboron group containing 1 to 40 carbon atoms, an arylboron group containing 6 to 60 carbon atoms, an arylphosphine group containing 6 to 60 carbon atoms, an oxyarylphosphine group containing 6 to 60 carbon atoms, or an arylamine group containing 6 to 60 carbon atoms, and each of these is unsubstituted or substituted. R1 to R3 are each independently an alkyl group containing 1 to 40 carbon atoms or an aryl group containing 6 to 60 carbon atoms, wherein each is unsubstituted or substituted. In this configuration, two adjacent groups selected from R1 to R3 can bond together to form a fused ring structure, and L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 30 carbon atoms, and each of them is either unsubstituted or substituted. The premise is that L1 and L3 are not both bonded to L2 in adjacent positions.

2. The organic light-emitting compound according to claim 1, wherein... Z1 to Z3 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 20 carbon atoms, and at least two of Z1 to Z3 are N. Ar1 and Ar2 are each independently an alkenyl group containing 2 to 20 carbon atoms, an alkynyl group containing 2 to 20 carbon atoms, a cycloalkyl group containing 3 to 20 carbon atoms, a heterocycloalkyl group containing 2 to 20 carbon atoms, an alkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, an alkoxy group containing 1 to 20 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, an alkylsilyl group containing 1 to 20 carbon atoms, an arylsilyl group containing 6 to 30 carbon atoms, an alkylboron group containing 1 to 20 carbon atoms, an arylboron group containing 6 to 30 carbon atoms, an arylphosphine group containing 6 to 30 carbon atoms, an oxyarylphosphine group containing 6 to 30 carbon atoms, or an arylamine group containing 6 to 30 carbon atoms. R1 to R3 are each independently an alkyl group containing 1 to 20 carbon atoms or an aryl group containing 6 to 30 carbon atoms, wherein... Two adjacent groups selected from R1 to R3 can bond together to form a fused ring structure, and L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 20 carbon atoms. Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

3. The organic light-emitting compound according to claim 1, wherein... Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N. Ar1 and Ar2 are each independently an aryl group containing 6 to 30 carbon atoms, or a heteroaryl group containing 2 to 30 carbon atoms. R1 to R3 are each independently an alkyl group containing 1 to 10 carbon atoms or an aryl group containing 6 to 20 carbon atoms, and at least one of R1 and R3 is an aryl group having 2 to 20 carbon atoms. Two adjacent groups selected from R1 to R3 can bond together to form a fused ring structure, and L by This indicates that L1 to L3 are each independently an aryl group containing 6 to 20 carbon atoms. Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

4. The organic light-emitting compound according to claim 1, wherein... Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N. Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, or a dibenzo[a] group. R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group, or a naphthyl group, wherein, Two adjacent groups selected from R1 to R3 can bond together to form a fused ring structure, and L by This indicates that L1 to L3 are each independently a phenylene group, a biphenyl group, or a naphthyl group. Among them, the bonding sites adjacent to L1 ( ) and the bonding site adjacent to L3 ( At least one of L1 and L3 is bonded at an adjacent position, and not both L1 and L3 are bonded to L2 at adjacent positions.

5. The organic light-emitting compound according to claim 1, wherein L can be represented by any one of the following formulas L-1 to L-7: [Formula L-1] ; [Formula L-2] ; [Formula L-3] ; [Formula L-4] ; [Formula L-5] ; [Formula L-6] ; [Formula L-7] ; In each of equations L-1 to L-7, This indicates the bonding site with Equation 1.

6. The organic light-emitting compound according to claim 1, wherein... Z1 to Z3 are each independently N or CH, and at least two of Z1 to Z3 are N. Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, or a naphthyl group. R1 to R3 are each independently a methyl group, a phenyl group, a biphenyl group, or a naphthyl group, wherein, Two adjacent groups selected from R1 to R3 can bond together to form a fused ring structure, and L is represented by the following formulas: L-1, L-2, L-6, or L-7: [Formula L-1] ; [Formula L-2] ; [Formula L-6] ; [Formula L-7] ; In each of equations L-1, L-2, L-6, or L-7, This indicates the bonding site with Equation 1.

7. The organic light-emitting compound according to claim 1, wherein formula 1 can be represented by any one of formulas 2 to 5: [Equation 2] ; [Formula 3] ; [Formula 4] ; [Formula 5] ; in, In each of Equations 2 to 5, Ar1 and Ar2 are each independently either phenyl groups or biphenyl groups. R1 to R3 are each independently a methyl group, a phenyl group, or a biphenyl group, wherein two adjacent groups selected from R1 to R3 can be bonded together to form a fused ring structure.

8. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound represented by formula 1 is selected from any one of compounds 1 to 180: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 。 9. An organic electroluminescent device comprising the organic light-emitting compound according to claim 1.

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

11. The organic electroluminescent device according to claim 10, wherein, The electron transport region includes at least one of an electron transport layer or an electron transport auxiliary layer; and The organic light-emitting compound is contained in at least one layer of the electron transport layer or the electron transport auxiliary layer.

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

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

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