Organic light-emitting compound and organic electroluminescent device comprising same

Abstract

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

Description

Cross-references to related applications

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2023-0171096, filed with the Korean Intellectual Property Office on November 30, 2023, and Korean Patent Application No. 10-2024-0147485, filed with the Korean Intellectual Property Office on October 25, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The embodiments disclosed herein relate to a novel organic light-emitting compound and an organic electroluminescent device comprising the compound. Background Technology

[0003] Since Bernanose first discovered the phenomenon of organic thin film luminescence in the 1950s, research on organic electroluminescence (EL) devices based on blue electroluminescence was conducted using anthracene single crystals in 1965. In 1987, Tang proposed an organic electroluminescence device with a stacked structure, which consists of functional layers including a hole layer and a light-emitting layer. Subsequently, organic electroluminescence devices with various characteristic organic layers have been developed to endow the devices with high efficiency and long lifetime, and specific materials for the devices have been developed.

[0004] When a voltage is applied between the two electrodes of an organic electroluminescent device, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes combine with the electrons, excitons are formed. When the excitons transition to the ground state, light is emitted. In this case, based on their function, the materials used for the organic material layer can be classified as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials, etc.

[0005] Light-emitting materials used in organic electroluminescent devices can be categorized into blue, green, and red light-emitting materials based on the color of the light emitted. Additionally, yellow and orange light-emitting materials are also used to achieve more natural color effects. Furthermore, host / dopant systems can also be used as light-emitting materials to improve color purity and luminous efficiency through energy transfer.

[0006] Dopant materials can be divided into fluorescent dopants that use organic materials and phosphorescent dopants that use metal complexes containing heavy atoms such as iridium and platinum. Since such phosphorescent materials can theoretically increase the luminous efficiency to four times that of fluorescent materials, a great deal of research has been conducted on phosphorescent host materials and phosphorescent dopant materials.

[0007] As shown below, NPB, BCP, Alq3, etc., are currently widely considered as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as luminescent layer materials. In particular, among luminescent layer materials, iridium-containing metal complexes, such as FIrpic, Ir(ppy)3, and (acac)Ir(btp)2 shown below, have the advantage of improved efficiency and are used as blue, green, and red phosphorescent dopants, while 4,4-dicarbazolium biphenyl (CBP) shown below is used as a phosphorescent host material.

[0008]

[0009] Therefore, traditional organic layer materials have advantages in terms of light-emitting properties, but due to their low glass transition temperature and poor thermal stability, they cannot satisfactorily improve the lifespan of organic electroluminescent devices.

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

[0011] Existing technical documents

[0012] Korean Patent Publication No. 10-2021-0030417 Summary of the Invention

[0013] [Technical Issues]

[0014] The embodiments disclosed herein provide novel organic light-emitting compounds and their uses that exhibit excellent thermal stability, hole-electron binding energy, efficiency, etc.

[0015] The embodiments disclosed herein provide an organic electroluminescent device comprising the novel organic light-emitting compound, which has low driving voltage, high current efficiency, and improved luminescent performance and lifetime.

[0016] It should be noted that the purpose of 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.

[0017] [Technical Solution]

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

[0019] [Formula 1]

[0020]

[0021] In Equation 1,

[0022] X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N.

[0023] Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N.

[0024] The premise is to exclude the cases where all X1 to X3 and Y1 to Y3 are N.

[0025] R1 and R2 are each independently hydrogen, an alkyl group containing 1 to 30 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 50 carbon atoms, a silyl group containing 1 to 60 carbon atoms, a phosphine oxide group containing 1 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted, and

[0026] Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, a silyl group containing 4 to 60 carbon atoms, a phosphine oxide group containing 3 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted.

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

[0028] Embodiments of this disclosure provide the use of organic light-emitting compounds in organic electroluminescent devices.

[0029] [Beneficial Effects]

[0030] The organic light-emitting compounds disclosed herein possess excellent thermal stability due to their high glass transition temperature (Tg), thus providing a long lifetime, while exhibiting improved electron transport and luminescence capabilities, and are therefore suitable as organic layers in organic electroluminescent devices.

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

[0032] The effects of this disclosure are not limited to those described above, and other technical effects not mentioned will be apparent to those skilled in the art from the following description.

[0033] [Best Mode]

[0034] The advantages and features of this disclosure and its implementation methods will be clearly understood from the following detailed description of the embodiments. However, this disclosure is not limited to these embodiments and may be implemented in different forms. These embodiments are only intended to provide a thorough and complete understanding of this disclosure and to fully inform those skilled in the art of the technical conception of this disclosure, which is limited only by the scope of 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 specifies otherwise, the singular form should also include the plural form. Furthermore, it should be 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 described.

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

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

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

[0039] As used in this article, the term "aryl group" can refer to a monovalent functional group derived from aromatic hydrocarbons. Aryl groups may include, for example, phenyl groups, naphthyl groups, anthracene groups, tetraphenyl groups, pyrene groups, tolyl groups, biphenyl groups, terphenyl groups, phenanthrene groups, spirodifluorenyl groups, fluorenyl groups, peryl groups, indole groups, azulel groups, hepta-enyl groups, naphthylphenyl groups, phenanthrene groups, etc., but are not limited to these.

[0040] As used herein, the term "heteroaryl group" refers to a monovalent functional group derived from an aromatic heterocycle having a monocyclic or fused-ring structure. In addition to a carbon atom, 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. 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, indole groups, isoindole groups, nitrogen-containing indole groups, purine groups, indazole groups, quinolinyl groups, isoquinolinyl groups, quinazinyl groups, phthalazinyl groups, naphthyl groups, quinoxalinyl groups, quinazolinyl groups, and porphyrin groups. The heteroaryl groups include: pyridyl groups, imidazotriazinyl groups, acridine groups, phenanthridine groups, carbazoyl 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. For example, the number of nucleoatomic atoms in each heteroaryl group 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, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl, n-hexyl, 1-methyl-2-ethylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl, 1-propylpropyl, 1-methylbutyl, 2-methylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 2-methylpentyl, 3-methylpentyl, etc., but are not limited thereto.

[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, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited to these.

[0043] As used herein, the term "halogenated alkyl group" refers to a monovalent functional group derived from an alkyl group (in which at least one hydrogen atom is replaced by a halogen atom). The halogen atom may be at least one selected from F, Cl, Br, and I.

[0044] As used herein, the term "silyl group" may refer to a monovalent functional group derived from a compound in which at least one hydrogen atom of a silane is replaced by the aforementioned alkyl group and / or aryl group.

[0045] As used herein, the term "phosphine oxide group" may refer to a monovalent functional group derived from a compound in which phosphine oxide is substituted by the aforementioned alkyl and / or aryl groups.

[0046] As used herein, the term "substitution" means substitution by at least one substituent selected from the group consisting of: deuterium, halogen, cyano group, nitrile group, alkyl group containing 1 to 30 carbon atoms, haloalkyl group containing 1 to 30 carbon atoms, cycloalkyl group containing 1 to 30 carbon atoms, aryl group containing 6 to 30 carbon atoms, heteroaryl group containing 2 to 20 carbon atoms, or heteroaryl group containing 5 to 20 nucleomeric atoms. When substituted by multiple substituents, these substituents may be the same or different from each other. Furthermore, the substituents may be in the form of bonds to a deuterium (D) atom.

[0047] <Organic luminescent compounds>

[0048] This disclosure provides a novel organic light-emitting compound. The organic light-emitting compound is represented by the following formula 1.

[0049] [Formula 1]

[0050]

[0051] In Equation 1,

[0052] X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N.

[0053] Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N.

[0054] The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded.

[0055] R1 and R2 are each independently hydrogen, an alkyl group containing 1 to 30 carbon atoms, an aryl group containing 6 to 60 carbon atoms, a heteroaryl group containing 2 to 50 carbon atoms, a heteroaryl group containing 5 to 50 nucleomeric atoms, a silyl group containing 1 to 60 carbon atoms, a phosphine oxide group containing 1 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted.

[0056] Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 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, a silyl group containing 4 to 60 carbon atoms, a phosphine oxide group containing 3 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted.

[0057] Specifically, at least one of hydrogen, alkyl group, aryl group, heteroaryl group, silyl group, phosphine oxide group, or nitrile group may exist as R1, R2, and Ar1 to Ar4, each of which is independently unsubstituted or substituted by at least one substituent selected from the group consisting of: deuterium, halogen, cyano group, nitrile group, alkyl group containing 1 to 30 carbon atoms, haloalkyl group containing 1 to 30 carbon atoms, cycloalkyl group containing 1 to 30 carbon atoms, aryl group containing 5 to 30 carbon atoms, heteroaryl group containing 2 to 20 carbon atoms, or heteroaryl group containing 5 to 20 nucleomeric atoms. When substituted by multiple substituents, these substituents may be the same or different from each other.

[0058] In one implementation scheme, in Equation 1,

[0059] X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N.

[0060] Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N.

[0061] The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded.

[0062] R1 and R2 are each independently hydrogen, or alkyl groups containing 1 to 10 carbon atoms, and

[0063] Ar1 to Ar4 are each independently an aryl group containing 6 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a heteroaryl group containing 5 to 30 nucleomeric atoms, a silyl group containing 1 to 30 carbon atoms, or a phosphine oxide group containing 1 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group containing 1 to 10 carbon atoms, a haloalkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, a heteroaryl group containing 5 to 20 nucleomeric atoms, a halogen group, a nitrile group, or a hydroxyl group.

[0064] In one implementation scheme, in Equation 1,

[0065] X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N.

[0066] Y1 to Y3 are each independently either N or CR2, wherein at least one of Y1 to Y3 is N.

[0067] The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded.

[0068] R1 and R2 are each independently hydrogen, and

[0069] Ar1 to Ar4 are each independently selected from one of formulas 1-1 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 6 to 10 carbon atoms, a heteroaryl group containing 2 to 10 carbon atoms, a heteroaryl group containing 5 to 10 nucleomeric atoms, a halogen group, a nitrile group, or a hydroxyl group.

[0070] [Equation 1-1]

[0071]

[0072] [Equation 1-2]

[0073]

[0074] [Equation 1-3]

[0075]

[0076] [Equations 1-4]

[0077]

[0078] [Equations 1-5]

[0079]

[0080] [Equations 1-6]

[0081]

[0082] [Equations 1-7]

[0083]

[0084] [Equations 1-8]

[0085]

[0086] [Equations 1-9]

[0087]

[0088] [1-10]

[0089]

[0090] [Equation 11-11]

[0091]

[0092] [Equation 1-12]

[0093]

[0094] [Equation 1-13]

[0095]

[0096] [Equation 1-14]

[0097]

[0098] [Equation 1-15]

[0099]

[0100] [Equation 1-16]

[0101]

[0102] [Equation 1-17]

[0103]

[0104] In each of Equations 1-1 to 1-17, * denotes the bonding site with Equation 1, and

[0105] R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

[0106] A ring formed by the interconnection of R4 and R5 refers to a ring structure formed by the connection of R4 and R5 via single bonds. For example, when R4 is an alkyl group containing 5 carbon atoms and R5 is an alkyl group containing 4 carbon atoms, R4 and R5 can be connected to form a ring with up to 9 carbon atoms. However, the position of the single bond connecting R4 and R5 is not limited to its terminal position; it can also be formed in the internal position of R4 and R5. The ring formed by R4 and R5 can be, for example, cyclopentane, cyclohexane, cycloheptane, chlorocyclopentane, or chlorocyclohexane, but is not limited to these.

[0107] In one implementation scheme, in Equation 1,

[0108] One of X1 to X3 is N and one of Y1 to Y3 is N; one of X1 to X3 is N and two of Y1 to Y3 are N; one of X1 to X3 is N and all of Y1 to Y3 are N; two of X1 to X3 are N and two of Y1 to Y3 are N; two of X1 to X3 are N and all of Y1 to Y3 are N; all of X1 to X3 are N and one of Y1 to Y3 is N; or all of X1 to X3 are N and two of Y1 to Y3 are N;

[0109] R1 and R2 are each independently hydrogen;

[0110] Ar1 and Ar2 are each independently selected from one of equations 1-1 to 1-3;

[0111] Ar3 and Ar4 are each independently selected from one of formulas 1-1 to 1-3, 1-7 to 1-9, and 1-12 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, or a nitrile group.

[0112] [Equation 1-1]

[0113]

[0114] [Equation 1-2]

[0115]

[0116] [Equation 1-3]

[0117]

[0118] [Equations 1-7]

[0119]

[0120] [Equations 1-8]

[0121]

[0122] [Equations 1-9]

[0123]

[0124] [Equation 1-12]

[0125]

[0126] [Equation 1-13]

[0127]

[0128] [Equation 1-14]

[0129]

[0130] [Equation 1-15]

[0131]

[0132] [Equation 1-16]

[0133]

[0134] [Equation 1-17]

[0135]

[0136] In each of Equations 1-1 to 1-3, 1-7 to 1-9, and 1-12 to 1-17, * denotes the binding site with Equation 1, and

[0137] R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

[0138] In one implementation scheme, in Equation 1,

[0139] Two of X1 to X3 are N and all of Y1 to Y3 are N, all of X1 to X3 are N and two of Y1 to Y3 are N, or two of X1 to X3 are N and two of Y1 to Y3 are N;

[0140] R1 and R2 are each independently hydrogen;

[0141] Ar1 and Ar2 are given by equation 1-1, and

[0142] Ar3 and Ar4 are each independently selected from one of formulas 1-1, 1-2, 1-7, 1-8, 1-14, and 1-15, each of which is either unsubstituted or substituted with a halogen group.

[0143] [Equation 1-1]

[0144]

[0145] [Equation 1-2]

[0146]

[0147] [Equations 1-7]

[0148]

[0149] [Equations 1-8]

[0150]

[0151] [Equation 1-14]

[0152]

[0153] [Equation 1-15]

[0154]

[0155] In each of Equations 1-1, 1-2, 1-7, 1-8, 1-14, and 1-15, * denotes the binding site with Equation 1.

[0156] R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

[0157] In one embodiment, the organic light-emitting compound represented by Formula 1 may be any one selected from compounds 1 to 701.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] In one implementation, Equation 1 may be represented by any one of Equations 2 through 6 below:

[0228] [Equation 2]

[0229]

[0230] [Formula 3]

[0231]

[0232] [Formula 4]

[0233]

[0234] [Formula 5]

[0235]

[0236] [Formula 6]

[0237]

[0238] In each of equations 2 to 6,

[0239] Ar1 and Ar2 are phenyl groups, and

[0240] Ar3 and Ar4 are each independently a phenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrimidinyl group, or a fluorophenyl group.

[0241] As a specific example, the compound represented by Formula 1 may be selected from any one of compounds 1, 17, 27, 39, 58, 61, 96, 111, 271, 287, 297, 309, 328, 361, 411, 441, 449, 471, 468, 506 and 521.

[0242] The novel organic light-emitting compounds disclosed herein contain two strong electron-withdrawing groups, namely a triazine group and a pyrimidine group, in their molecular structure, thereby providing favorable properties in terms of electron injection and transport, and exhibiting excellent electron transfer capability to transfer electrons to the light-emitting layer. Therefore, when used in organic electroluminescent devices, they can help improve the initial driving voltage of the organic electroluminescent devices.

[0243] Furthermore, the novel organic light-emitting compounds according to this disclosure have a structure in which a triazine group and a pyrimidine group are bonded to opposite sides of a biphenyl group, one in the ortho position and the other in the meta position, thereby enabling the realization of shallower least unoccupied molecular orbital (LUMO) energy levels and improving processability.

[0244] Furthermore, the novel organic light-emitting compounds according to this disclosure contain aromatic groups rather than simple aliphatic ring structures, thus they are expected to have high thermal stability and do not exhibit a crystallization temperature (Tc), thereby effectively improving the processability and lifespan of the device.

[0245] Organic electroluminescent devices

[0246] This disclosure provides an organic electroluminescent device comprising the aforementioned novel organic light-emitting compound. 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.

[0247] 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.

[0248] anode

[0249] The organic electroluminescent device disclosed herein includes an anode. The anode is used to inject holes into an organic layer. Here, the organic layer may refer to at least one layer formed between the anode and the cathode.

[0250] There are no particular limitations on the type of anode material, which can be prepared according to conventional methods known in the art. For example, anode materials may include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); metal-oxide complexes such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDT), polypyrrole, or polyaniline; or carbon black. The compound may be used alone or in combination of two or more of these materials.

[0251] There are no particular limitations on the preparation method of the anode, and it can be prepared according to conventional methods known in the art. For example, the anode can be formed by coating a substrate such as a silicon wafer, quartz, glass plate, metal plate or plastic film with an anode material.

[0252] cathode

[0253] The organic electroluminescent device disclosed herein includes a cathode. The cathode is used to inject electrons into an organic layer.

[0254] There are no particular restrictions 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.

[0255] Emissive layer

[0256] 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.

[0257] The light-emitting material that constitutes the light-emitting layer can be selected from a variety of commercially available materials without any particular restriction, depending on the required light emission wavelength.

[0258] In one implementation, the luminescent material can be categorized into blue, green, and red luminescent materials, based on the color of the emitted light. The luminescent layer can be formed as a combination of a host material and dopants, serving as the luminescent material to prevent problems such as decreased color purity or reduced device efficiency due to light emission attenuation effects. The luminous efficiency of an organic electroluminescent device can be improved by using a host material (which constitutes the main material of the luminescent layer) and a small amount of dopants with a band gap smaller than that of the host material.

[0259] Electronic transmission area

[0260] The organic electroluminescent device disclosed herein includes an electron transport region disposed between the light-emitting layer and the cathode.

[0261] An electron transport region is used to transport electrons injected from the cathode to the light-emitting layer. This electron transport region may include at least one of the group consisting of an electron injection layer or an electron transport layer. In this case, considering the characteristics of an organic electroluminescent device, the organic electroluminescent device preferably includes both the aforementioned electron transport layer and electron injection layer.

[0262] In the electron transport region, the electron injection layer can be formed of any electron injection material that facilitates 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 the group consisting of lanthanides such as LiF, Li₂O, BaO, NaCl, CsF, and Yb; and metal halides such as RbCl and RbI.

[0263] The electron transport layer may comprise the organic light-emitting compound according to the present disclosure. The organic light-emitting compound according to the present disclosure contains two strongly electron-withdrawing groups, namely a triazine group and a pyrimidine group, in its molecular structure, thereby providing advantageous properties in terms of electron injection and transport, and exhibiting excellent electron transfer capability to transfer electrons to the light-emitting layer, thus contributing to improving the initial driving voltage of the organic electroluminescent device when used in such a device. Furthermore, the novel organic light-emitting compound according to the present disclosure has a structure in which the triazine group and the pyrimidine group are bonded to opposite sides of the biphenyl group, one in the ortho position and the other in the meta position, thereby enabling the realization of a shallower least unoccupied molecular orbital (LUMO) energy level and improving processability. Moreover, organic electroluminescent devices using the organic light-emitting compound according to the present invention in the electron transport layer can have low refractive index, high efficiency, and long lifetime.

[0264] 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, thus lowering the potential barrier.

[0265] The electron transport region can be prepared using conventional methods known in the art. Methods for forming the electron transport region may include, but are not limited to, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0266] Electron transport auxiliary layer

[0267] The organic electroluminescent device disclosed herein may include an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region. The electron transport auxiliary layer prevents excitons or holes generated in the light-emitting layer from diffusing into the electron transport region.

[0268] As described above, the electron transport auxiliary layer may comprise an organic light-emitting compound according to the present disclosure. The organic light-emitting compound according to the present disclosure contains two strongly electron-withdrawing groups, namely a triazine group and a pyrimidine group, in its molecular structure, thereby providing advantageous properties in terms of electron injection and transport, and exhibiting excellent electron transfer capability to transfer electrons to the light-emitting layer, thus contributing to improved initial driving voltage of the organic electroluminescent device when used in such devices. Furthermore, the novel organic light-emitting compound according to the present disclosure has a structure in which the triazine group and the pyrimidine group are bonded to opposite sides of the biphenyl group, one in the ortho position and the other in the meta position, thereby enabling the realization of shallower least unoccupied molecular orbital (LUMO) energy levels and improving processability. Moreover, organic electroluminescent devices using the organic light-emitting compound according to the present invention in the electron transport auxiliary layer can have low refractive index, high efficiency, and long lifetime.

[0269] The electron transport auxiliary layer can be formed according to conventional methods known in the art, such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser-induced thermal imaging (LITI), but is not limited thereto.

[0270] Hole transport region

[0271] 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 from the anode to the light-emitting layer.

[0272] The hole transport region may include at least one selected from the group consisting of a hole injection layer or a hole transport layer. In this case, considering the characteristics of the organic electroluminescent device, the organic electroluminescent device preferably includes both the hole transport layer and the hole injection layer described above.

[0273] Any material can be used as the hole injection layer and the hole transport layer without particular limitation, as long as it has a low hole injection barrier and a high hole mobility, and can be selected from hole injection materials and hole transport materials already used in the art without limitation. The materials constituting the hole injection layer and the materials constituting the hole transport layer may be the same or different from each other.

[0274] Hole injection materials 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), 2TNATA (4,4'... The compounds include 4'-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine, PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), etc. These compounds can be used alone or in combination of two or more of them.

[0275] Furthermore, the hole transport material can be selected from hole transport materials known in the art without limitation. Non-limiting examples of useful hole transport materials include: carbazole derivatives such as phenylcarbazole and polyvinylcarbazole; fluorenyl derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4''-tris(N-carbazolyl)triphenylamine); NPB (N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]), etc. The compound can be used alone or in combination of two or more of these materials.

[0276] The hole transport layer 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 is not limited thereto.

[0277] Light-emitting auxiliary layer

[0278] 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 and to transport holes from the hole transport region to the light-emitting layer. The light-emitting auxiliary layer prevents electrons from moving to the hole transport layer based on its high LUMO; and prevents excitons from moving from the light-emitting layer to the hole transport layer based on its high triplet (T1) energy.

[0279] The light-emitting auxiliary layer may contain 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.

[0280] There are no particular limitations on the materials used for the light-emitting auxiliary layer, such as carbazole derivatives, arylamine derivatives, or carbazole-arylamine derivatives. In addition to the above materials, the light-emitting auxiliary layer may optionally contain a p-type dopant. The p-type dopant can be any p-type dopant used in the art.

[0281] Cover layer

[0282] 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.

[0283] The covering material constituting the covering layer may include, for example, at least one selected from the group consisting of: tri-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2"-bipyridine))-1,1-dimethyl-3,4-diphenylthiophene, 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-tolylaminophenyl)cyclohexane (TAPC), but is not limited thereto.

[0284] The covering layer may be a single layer, or it may include two or more layers with different refractive indices to gradually change the refractive index of light passing through the two or more layers.

[0285] The capping layer can be formed using conventional methods known in the art, which can be selected from a variety of methods such as vacuum deposition, spin coating, casting and LB (Langmuir-Blodgett).

[0286] This disclosure provides the use of the aforementioned organic light-emitting compound in organic electroluminescent devices. The organic light-emitting compound significantly improves the luminescence performance, driving voltage, lifetime, and efficiency of organic electroluminescent devices.

[0287] In one embodiment, the organic light-emitting compound can be used as an electron transport material in an organic electroluminescent device.

[0288] 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.

[0289] In one embodiment, the organic light-emitting compound can be used as a material for the electron transport layer and / or electron transport auxiliary layer in an organic electroluminescent device.

[0290] The present disclosure will now be described with reference to specific embodiments. However, the following embodiments are for illustrative purposes only and should not be construed as limiting the scope of the disclosure.

[0291]

Preparation Examples

[0292]

Preparation Example 1

[0293]

[0294] 2-Chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (3.1 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-1 (2.14 g, 80% yield) was obtained by column chromatography.

[0295]

Preparation Example 2

[0296]

[0297] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (4.19 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxoborane) (2.5 g, 10 mmol), Pd(dppf)Cl2 (0.2 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and KOAc (2.0 g, 19.9 mmol) were added to 100 mL of 1,4-dioxane and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-2 (3.1 g, 75% yield) was obtained by column chromatography.

[0298]

Preparation Example 3

[0299]

[0300] 4-Chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (3.1 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-3 (2.13 g, 80% yield) was obtained by column chromatography.

[0301]

Preparation Example 4

[0302]

[0303] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine (4.18 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxoborane) (2.5 g, 10 mmol), Pd(dppf)Cl2 (0.2 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and KOAc (2.0 g, 19.9 mmol) were added to 100 mL of 1,4-dioxane and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-4 (2.93 g, 70% yield) was obtained by column chromatography.

[0304]

Preparation Example 5

[0305]

[0306] 2-Chloro-4,6-diphenylpyrimidine (2.66 g, 10 mmol), 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (3.1 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-5 (2.13 g, 80% yield) was obtained by column chromatography.

[0307]

Preparation Example 6

[0308]

[0309] 2-(2'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyridine (4.18 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxoborane) (2.5 g, 10 mmol), Pd(dppf)Cl2 (0.2 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and KOAc (2.0 g, 19.9 mmol) were added to 100 mL of 1,4-dioxane and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and the target compound H-6 (2.93 g, 70% yield) was obtained by column chromatography.

[0310]

Synthesis Example

[0311] [Synthetic Example 1]: Synthesis of Compound 1

[0312]

[0313] H⁻⁵ (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), Pd(PPh₃)₄ (0.34 g, 0.3 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO₄, and filtered. The solvent was removed from the filtered organic layer, and compound 1 (3.58 g, 70% yield) was obtained by column chromatography.

[0314] Mass: [(M+H)] + ]:615

[0315] [Synthetic Example 2]: Synthesis of Compound 17

[0316]

[0317] H⁻⁵ (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), Pd(PPh₃)₄ (0.34 g, 0.3 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO₄, and filtered. The solvent was removed from the filtered organic layer, and compound 17 (3.83 g, 75% yield) was obtained by column chromatography.

[0318] Mass: [(M+H)] + ]:615

[0319] [Synthetic Example 3]: Synthesis of Compound 27

[0320]

[0321] H⁻⁵ (5.11 g, 10 mmol), 4-chloro-2-(naphth-2-yl)-6-phenylpyrimidine (3.16 g, 10 mmol), Pd(PPh₃)₄ (0.34 g, 0.3 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO₄, and filtered. The solvent was removed from the filtered organic layer, and compound 27 (4.5 g, 88% yield) was obtained by column chromatography.

[0322] Mass: [(M+H)] + ]:665

[0323] [Synthetic Example 4]: Synthesis of Compound 39

[0324]

[0325] H-2 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine (3.56 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 39 (4.60 g, 90% yield) was obtained by column chromatography.

[0326] Mass: [(M+H)] +]:705

[0327] [Synthetic Example 5]: Synthesis of Compound 58

[0328]

[0329] H-2 (5.11 g, 10 mmol), 4-chloro-2-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenylpyrimidine (3.82 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL Et4-chloro-2-(dibenzo[b,d]thiophene-3-yl)-6-phenylpyrimidine OH, and 25 mL water. The mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 58 (3.78 g, 74% yield) was obtained by column chromatography.

[0330] Mass: [(M+H)] + ]:731

[0331] [Synthetic Example 6]: Synthesis of Compound 61

[0332]

[0333] H-2 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]thiophene-3-yl)-6-phenylpyrimidine (3.72 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 61 (3.89 g, 76% yield) was obtained by column chromatography.

[0334] Mass: [(M+H)] + ]:772

[0335] [Synthetic Example 7]: Synthesis of Compound 96

[0336]

[0337] H₂ (5.11 g, 10 mmol), 4-chloro-6-phenyl-2-(pyridin-3-yl)pyrimidine (2.67 g, 10 mmol), Pd(PPh₃)₄ (0.34 g, 0.3 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO₄, and filtered. The solvent was removed from the filtered organic layer, and compound 96 (3.94 g, 77% yield) was obtained by column chromatography.

[0338] Mass: [(M+H)] + ]:616

[0339] [Synthetic Example 8]: Synthesis of Compound 111

[0340]

[0341] H⁻⁵ (5.11 g, 10 mmol), 4-chloro-2-(4-fluorophenyl)-6-phenylpyrimidine (2.84 g, 10 mmol), Pd(PPh₃)₄ (0.34 g, 0.3 mmol), and K₂CO₃ (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO₄, and filtered. The solvent was removed from the filtered organic layer, and compound 111 (3.78 g, 74% yield) was obtained by column chromatography.

[0342] Mass: [(M+H)] + ]:633

[0343] [Synthetic Example 9]: Synthesis of Compound 271

[0344]

[0345] H-4 (5.10 g, 10 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 271 (3.83 g, 75% yield) was obtained by column chromatography.

[0346] Mass: [(M+H)]+ ]:615

[0347] [Synthetic Example 10]: Synthesis of Compound 287

[0348]

[0349] H-6 (5.11 g, 10 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 287 (3.93 g, 77% yield) was obtained by column chromatography.

[0350] Mass: [(M+H)] + ]:615

[0351] [Synthetic Example 11]: Synthesis of Compound 297

[0352]

[0353] H-6 (5.11 g, 10 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (3.17 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 297 (3.32 g, 65% yield) was obtained by column chromatography.

[0354] Mass: [(M+H)] + ]:665

[0355] [Synthetic Example 12]: Synthesis of Compound 309

[0356]

[0357] H-4 (5.11 g, 10 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.57 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 309 (3.83 g, 75% yield) was obtained by column chromatography.

[0358] Mass: [(M+H)] + ]:705

[0359] [Synthetic Example 13]: Synthesis of Compound 328

[0360]

[0361] H-4 (5.11 g, 10 mmol), 2-chloro-4-(9,9-dimethyl-9H-fluorene-3-yl)-6-phenyl-1,3,5-triazine (3.83 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 328 (3.78 g, 74% yield) was obtained by column chromatography.

[0362] Mass: [(M+H)] + ]:731

[0363] [Synthetic Example 14]: Synthesis of Compound 361

[0364]

[0365] H-4 (5.11 g, 10 mmol), 2-chloro-4-(4-fluorophenyl)-6-phenyl-1,3,5-triazine (2.85 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 361 (4.08 g, 80% yield) was obtained by column chromatography.

[0366] Mass: [(M+H)] + ]:633

[0367] [Synthetic Example 15]: Synthesis of Compound 411

[0368]

[0369] H-4 (5.11 g, 10 mmol), 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 411 (3.73 g, 73% yield) was obtained by column chromatography.

[0370] Mass: [(M+H)] + ]:614

[0371] [Synthetic Example 16]: Synthesis of Compound 441

[0372]

[0373] H-4 (5.11 g, 10 mmol), 4-chloro-2-(naphth-1-yl)-6-phenylpyrimidine (3.16 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 441 (3.93 g, 77% yield) was obtained by column chromatography.

[0374] Mass: [(M+H)]+ ]:664

[0375] [Synthetic Example 17]: Synthesis of Compound 449

[0376]

[0377] H-4 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]furan-3-yl)-6-phenylpyrimidine (3.56 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 449 (3.83 g, 75% yield) was obtained by column chromatography.

[0378] Mass: [(M+H)] + ]:704

[0379] [Synthetic Example 18]: Synthesis of Compound 471

[0380]

[0381] H-4 (5.11 g, 10 mmol), 4-chloro-2-(dibenzo[b,d]thiophene-3-yl)-6-phenylpyrimidine (3.72 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 471 (3.93 g, 77% yield) was obtained by column chromatography.

[0382] Mass: [(M+H)] + ]:720

[0383] [Synthetic Example 19]: Synthesis of Compound 468

[0384]

[0385] H-4 (5.11 g, 10 mmol), 4-chloro-2-(9,9-dimethyl-9H-fluorene-3-yl)-6-phenylpyrimidine (3.82 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 468 (3.78 g, 74% yield) was obtained by column chromatography.

[0386] Mass: [(M+H)] + ]:730

[0387] [Synthetic Example 20]: Synthesis of Compound 506

[0388]

[0389] H-4 (5.11 g, 10 mmol), 4-chloro-6-phenyl-2-(pyridin-3-yl)pyrimidine (2.67 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL water, and 25 mL water. The mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 506 (3.83 g, 75% yield) was obtained by column chromatography.

[0390] Mass: [(M+H)] + ]:615

[0391]

Synthetic Example 21

[0392]

[0393] H-4 (5.11 g, 10 mmol), 4-chloro-2-(4-fluorophenyl)-6-phenylpyrimidine (2.84 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to a mixed solvent of 100 mL toluene, 25 mL ethanol, and 25 mL water, and the mixture was stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, treated with MgSO4, and filtered. The solvent was removed from the filtered organic layer, and compound 521 (3.68 g, 72% yield) was obtained by column chromatography.

[0394] Mass: [(M+H)] + ]:632

[0395] [Examples and Comparative Examples]

[0396] [Examples 1 to 21 and Comparative Examples 1 to 3]: Fabrication of a blue organic electroluminescent device

[0397] The compounds synthesized in the synthesis examples were purified to high purity by sublimation using commonly known methods, and then a blue organic electroluminescent device was manufactured according to the following process.

[0398] First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1200 Å is ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate is ultrasonically cleaned with a solvent such as isopropanol, and then dried and cleaned for 5 minutes using a UV ozone cleaner (Powersonic 405, Hwashin Tech) to fabricate a substrate with ITO transparent electrodes. The fabricated substrate is then transferred to a vacuum evaporator.

[0399] Hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport auxiliary layer, electron transport layer, electron injection layer and cathode are sequentially laminated onto the ITO transparent electrode (anode) of the substrate prepared as described above to manufacture an organic electroluminescent device. Specifically, the hole injection layer is formed by depositing 98 wt% HI and 2 wt% HAT-CN on the anode to a thickness of 6 to 10 nm; the hole transport layer is formed by depositing compound HI on the hole injection layer to a thickness of 140 nm; the light-emitting auxiliary layer is formed by depositing EB on the hole transport layer to a thickness of 5 nm; the light-emitting layer is formed by depositing 98 wt% BH and 2 wt% BD on the light-emitting auxiliary layer to a thickness of 20 nm; the electron transport auxiliary layer is formed by depositing material for the electron transport auxiliary layer on the light-emitting layer to a thickness of 5 nm; the electron transport layer is formed by depositing ET and Liq in a weight ratio of 1:1 on the electron transport auxiliary layer 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. The structures of HI, HAT-CN6, EB, BH, BD, ET and Liq are shown in Table 1 below, and the materials used for the electron transport auxiliary layer are shown in Table 2 below.

[0400] Table 1

[0401]

[0402] [Table 2]

[0403]

[0404] [Examples 22 to 42 and Comparative Examples 4 to 6]: Fabrication of a blue organic electroluminescent device

[0405] The compounds synthesized in the synthesis examples were purified to high purity by sublimation using commonly known methods, and then a blue organic electroluminescent device was manufactured according to the following process.

[0406] First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1200 Å is ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate is ultrasonically cleaned with a solvent such as isopropanol, and then dried and cleaned for 5 minutes using a UV ozone cleaner (Powersonic 405, Huaxin Technology) to fabricate a substrate with ITO transparent electrodes. The fabricated substrate is then transferred to a vacuum evaporator.

[0407] Hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport auxiliary layer, electron transport layer, electron injection layer and cathode are sequentially laminated onto the ITO transparent electrode (anode) of the substrate prepared as described above to manufacture an organic electroluminescent device. Specifically, the hole injection layer is formed by depositing 98 wt% HI and 2 wt% HAT-CN on the anode to a thickness of 6 to 10 nm; the hole transport layer is formed by depositing compound HI on the hole injection layer to a thickness of 140 nm; the light-emitting auxiliary layer is formed by depositing EB on the hole transport layer to a thickness of 5 nm; the light-emitting layer is formed by depositing 98 wt% BH and 2 wt% BD on the light-emitting auxiliary layer to a thickness of 20 nm; the electron transport auxiliary layer is formed by depositing HB on the light-emitting layer to a thickness of 5 nm; the electron transport layer is formed by depositing a material for the electron transport layer and Liq in a 1:1 weight ratio on the electron transport auxiliary layer 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. The structure of HB is shown in Table 3 below, and the material for the electron transport layer is shown in Table 4 below.

[0408] Table 3

[0409]

[0410] [Table 4]

[0411]

[0412]

Experimental Examples

[0413] [Experimental Example 1] Evaluation of the performance of the blue organic electroluminescent devices of Examples 1 to 21 and Comparative Examples 1 to 3

[0414] At 10mA / cm 2 The driving voltage, EL peak, and current efficiency of the organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 3 were measured at a current density, and the results are shown in Table 5 below.

[0415] Table 5

[0416]

[0417] As can be seen from Table 5, compared with the organic electroluminescent devices manufactured in Comparative Examples 1 to 3, the blue organic electroluminescent devices manufactured in Examples 1 to 21 showed excellent overall results in the evaluation of driving voltage and current efficiency.

[0418] [Experimental Example 2]: Evaluation of the performance of the blue organic electroluminescent devices of Examples 22 to 42 and Comparative Examples 4 to 6

[0419] At 10mA / cm 2 The driving voltage, EL peak, and current efficiency of the organic electroluminescent devices fabricated in Examples 22 to 42 and Comparative Examples 4 to 6 were measured at a current density, and the results are shown in Table 6 below.

[0420] Table 6

[0421]

[0422] As can be seen from Table 6, compared with the organic electroluminescent devices manufactured in Comparative Examples 4 to 6, the blue organic electroluminescent devices manufactured in Examples 22 to 42 showed excellent overall results in the evaluation of driving voltage and current efficiency.

[0423] 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 exemplary in various respects and do not limit this disclosure.

Claims

1. Organic light-emitting compounds represented by the following formula 1: [Formula 1] ; in, In Equation 1, X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N. Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N. The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded. R1 and R2 are each independently hydrogen, an alkyl group containing 1 to 30 carbon atoms, an aryl group containing 5 to 60 carbon atoms, a heteroaryl group containing 2 to 50 carbon atoms, a silyl group containing 1 to 60 carbon atoms, a phosphine oxide group containing 1 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted, and Ar1 to Ar4 are each independently an alkyl group containing 1 to 30 carbon atoms, an aryl group containing 5 to 60 carbon atoms, a heteroaryl group containing 2 to 60 carbon atoms, a silyl group containing 4 to 60 carbon atoms, a phosphine oxide group containing 3 to 60 carbon atoms, or a nitrile group, each of which is unsubstituted or substituted.

2. The organic light-emitting compound according to claim 1, wherein... X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N. Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N. The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded. R1 and R2 are each independently hydrogen or an alkyl group containing 1 to 10 carbon atoms, and Ar1 to Ar4 are each independently an aryl group containing 5 to 30 carbon atoms, a heteroaryl group containing 2 to 30 carbon atoms, a silyl group containing 1 to 30 carbon atoms, or a phosphine oxide group containing 1 to 30 carbon atoms, each of which is unsubstituted or substituted with deuterium, an alkyl group containing 1 to 10 carbon atoms, a haloalkyl group containing 1 to 10 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 20 carbon atoms, a heteroaryl group containing 2 to 20 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group.

3. The organic light-emitting compound according to claim 1, wherein... X1 to X3 are each independently N or CR1, wherein at least one of X1 to X3 is N. Y1 to Y3 are each independently N or CR2, wherein at least one of Y1 to Y3 is N. The premise is that the cases where X1 to X3 and Y1 to Y3 are all N are excluded. R1 and R2 are each independently hydrogen, and Ar1 to Ar4 are each independently selected from one of formulas 1-1 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group. [Equation 1-1] ; [Equation 1-2] ; [Equation 1-3] ; [Equations 1-4] ; [Equations 1-5] ; [Equations 1-6] ; [Equations 1-7] ; [Equations 1-8] ; [Equations 1-9] ; [1-10] ; [Equation 11-11] ; [Equation 1-12] ; [Equation 1-13] ; [Equation 1-14] ; [Equation 1-15] ; [Equation 1-16] ; [Equation 1-17] ; In each of equations 1-1 to 1-17, * indicates the bonding site with Equation 1, and R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

4. The organic light-emitting compound according to claim 1, wherein... One of X1 to X3 is N and one of Y1 to Y3 is N; one of X1 to X3 is N and two of Y1 to Y3 are N; one of X1 to X3 is N and all of Y1 to Y3 are N; two of X1 to X3 are N and two of Y1 to Y3 are N; two of X1 to X3 are N and all of Y1 to Y3 are N; all of X1 to X3 are N and one of Y1 to Y3 is N; or all of X1 to X3 are N and two of Y1 to Y3 are N; R1 and R2 are each independently hydrogen; Ar1 and Ar2 are each independently selected from one of equations 1-1 to 1-3; and Ar3 and Ar4 are each independently selected from one of formulas 1-1 to 1-3, 1-7 to 1-9, and 1-12 to 1-17, each of which is unsubstituted or substituted with deuterium, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, or a nitrile group. [Equation 1-1] ; [Equation 1-2] ; [Equation 1-3] ; [Equations 1-7] ; [Equations 1-8] ; [Equations 1-9] ; [Equation 1-12] ; [Equation 1-13] ; [Equation 1-14] ; [Equation 1-15] ; [Equation 1-16] ; [Equation 1-17] ; In each of equations 1-1 to 1-3, 1-7 to 1-9, and 1-12 to 1-17, * indicates the bonding site with Equation 1, and R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

5. The organic light-emitting compound according to claim 1, wherein... Two of X1 to X3 are N and all of Y1 to Y3 are N, all of X1 to X3 are N and two of Y1 to Y3 are N, or two of X1 to X3 are N and two of Y1 to Y3 are N; R1 and R2 are each independently hydrogen; Ar1 and Ar2 are given by equation 1-1, and Ar3 and Ar4 are each independently selected from one of formulas 1-1, 1-2, 1-7, 1-8, 1-14, and 1-15, each of which is either unsubstituted or substituted with a halogen group. [Equation 1-1] ; [Equation 1-2] ; [Equations 1-7] ; [Equations 1-8] ; [Equation 1-14] ; [Equation 1-15] ; In each of equations 1-1, 1-2, 1-7, 1-8, 1-14, and 1-15, * indicates the bonding site with Equation 1, and R4 and R5 are each independently hydrogen, deuterium, an alkyl group containing 1 to 5 carbon atoms, a haloalkyl group containing 1 to 5 carbon atoms, a cycloalkyl group containing 1 to 20 carbon atoms, an aryl group containing 5 to 10 carbon atoms, a halogen group, a nitrile group, or a hydroxyl group, and R4 and R5 can be linked together to form a ring.

6. 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 701: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 。 7. The organic light-emitting compound according to claim 1, wherein formula 1 is represented by any one selected from formulas 2 to 6: [Equation 2] ; [Formula 3] ; [Formula 4] ; [Formula 5] ; [Formula 6] ; In each of equations 2 to 6, Ar1 and Ar2 are phenyl groups, and Ar3 and Ar4 are each independently a phenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyrimidinyl group, or a fluorophenyl group.

8. An organic electroluminescent device comprising the organic light-emitting compound according to claim 1.

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

10. The organic electroluminescent device according to claim 9, 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 of the electron transport layer or electron transport auxiliary layer.

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

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

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