Organic compounds and organic electroluminescent elements containing such organic compounds

Abstract

This invention relates to a compound represented by chemical formula 1 and an organic electroluminescent element containing the compound, providing an organic compound with excellent lifetime, efficiency, electrochemical stability and thermal stability, and an organic electroluminescent element containing the compound.

Description

Technical Field

[0001] This invention relates to a novel organic compound and an organic electroluminescent element comprising the organic compound. Background Technology

[0002] Compared with other flat panel display elements such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic light-emitting diodes (OLEDs) have a simple structure, various advantages in manufacturing processes, high brightness and excellent viewing angle characteristics, fast response speed, and are being actively developed and commercialized due to their low driving voltage. This makes them suitable for use as light sources in flat panel displays such as wall-mounted TVs, backlighting of displays, lighting, billboards, etc.

[0003] The first organic EL device was reported by Tang et al. of Eastman Kodak (CWTang, SAVanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987). Its light-emitting principle is generally based on the fact that when a voltage is applied, holes injected from the positive electrode and electrons injected from the negative electrode recombine to form excitons, i.e., electron-hole pairs, and the energy of the excitons is transferred to the light-emitting material to be converted into light.

[0004] More specifically, the organic electroluminescent device has a structure including a negative electrode (electron injection electrode) and a positive electrode (hole injection electrode) and one or more organic layers between the two electrodes. In this case, the organic electroluminescent device is laminated from the positive electrode in the following order: hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL) or electron injection layer (EIL). To improve the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) can be further included before and after the light emitting layer, respectively.

[0005] The organic layer materials used in organic electroluminescent elements are mostly pure organic materials or complex compounds that form complexes between organic materials and metals. According to their uses, they can be classified as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials.

[0006] Among these, organic compounds that are easily oxidized and have an electrochemically stable state during oxidation are mainly used as hole injection or hole transport substances. Organic compounds that are easily reduced and have an electrochemically stable state during reduction are mainly used as electron injection or electron transport substances.

[0007] On one hand, the light-emitting layer material is preferably a material that is stable in both oxidized and reduced states, and preferably a material with high luminous efficiency in converting excitons into light. More specifically, the light-emitting layer is composed of two materials: a host material and a dopant material. The dopant material needs to have high quantum efficiency, and the host material preferably has a larger band gap than the dopant material to facilitate energy transfer to the dopant. Displays used in televisions, mobile devices, etc., achieve full color using red, green, and blue colors, and the light-emitting layers are respectively composed of red host / dopant, green host / dopant, and blue host / dopant.

[0008] Among existing materials used for blue dopants, fluorescent molecules such as perylene, coumarine, anthracene, and pyrene are widely utilized. However, the broad emission spectra and full width at half maximum (FWHM) of these dopants make it difficult to utilize pure blue light in device fabrication. This characteristic not only reduces the efficiency of blue light in the device's resonant structure but is also the main reason why the deep blue region is difficult to use.

[0009] Recently, literature on boron-based dopant-based devices with narrow emission spectra and high device efficiency has been published in Adv. Mater. 2016, 28, 2777-2781 and Angew. Chem. Int. Ed 2017, 56, 5087-5090, and also published in Korean Patent Publication No. 10-2016-0119683. In existing boron-based blue dopant materials, boron atoms are contained at the center and cyclized, thus forming only three coordination bonds, thereby maintaining the molecular structure in a planar state.

[0010] The advantage of this planar dopant structure is that the energy levels of the molecular vibrational modes are similar, thus narrowing the emission spectrum and half-width at half-maximum to produce pure light. However, when using this planar dopant structure to fabricate devices, the lack of outermost electrons in boron atoms increases the intensity of interactions with adjacent dopants, resulting in a more severe concentration quenching of the dopant.

[0011] Therefore, there is a need to develop a novel dopant that can maintain a narrow emission spectrum and half-amplitude while solving the concentration quenching problem during device fabrication. The concentration quenching phenomenon is the main reason for the decrease in efficiency due to the dopant concentration and the long wavelength of the color coordinates. Summary of the Invention

[0012] The problem the invention aims to solve

[0013] This invention provides an organic compound with excellent lifespan, efficiency, electrochemical stability and thermal stability, and an organic electroluminescent element containing the compound.

[0014] The organic compound of the present invention has a planar structure and can minimize the π (π-π) mutual attraction between molecules within the molecule, while the energy levels of the molecular vibration modes are almost similar, resulting in a narrow emission spectrum and half-amplitude. When the compound is used as a dopant, it provides an organic compound that can suppress possible concentration quenching.

[0015] In addition, the present invention provides an organic compound comprising atoms of a planar structure, such as boron-based elements, providing a compound of chemical formula 1, which can prevent the formation of excimers within the molecule, increase the electron density of the nucleus and the stability of the dopant, thereby increasing the efficiency and lifetime of the device.

[0016] In addition, the present invention aims to provide a blue host / dopant system and organic electroluminescent element suitable for AM-OLED blue series using the organic compound.

[0017] Solution for solving the problem

[0018] The present invention provides a compound represented by chemical formula 1, which is an organic compound having a narrow emission spectrum and half-amplitude, and being able to suppress concentration quenching even at high doping concentrations.

[0019] In addition, to provide organic electroluminescent devices with excellent luminous efficiency and lifetime characteristics, compounds represented by chemical formula 1 are used as dopants.

[0020] Invention Effects

[0021] This invention utilizes organic compounds with excellent lifetime, efficiency, electrochemical stability and thermal stability to provide an organic electroluminescent element with low driving voltage, high efficiency in the low doping range, and relatively suppressed efficiency reduction in the overdoping range. In particular, it has excellent lifetime and other characteristics. Detailed Implementation

[0022] The embodiments of the present invention will now be described in detail. However, these are merely examples, and the present invention is not limited to these examples; rather, it is defined only by the scope of the claims.

[0023] In this invention, unless otherwise defined, “substitution” means that at least one hydrogen atom in a substituent or compound is substituted by one or more substituents selected from the group consisting of deuterium, cyano, nitro, halogen, hydroxyl, alkylthio with 1 to 4 carbon atoms, aryloxy with 6 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, alkylamino with 1 to 30 carbon atoms, arylamino with 6 to 30 carbon atoms, arylalkylamino with 6 to 30 carbon atoms, heteroarylamino with 2 to 24 carbon atoms, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkyl with 1 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, alkynyl with 2 to 24 carbon atoms, aryl with 7 to 30 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, and heteroarylalkyl with 6 to 30 carbon atoms.

[0024] Furthermore, in the substituted cyano, nitro, halogen, hydroxyl, alkylthio group with 1 to 4 carbon atoms, aryloxy group with 6 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, alkylamino group with 1 to 30 carbon atoms, arylamino group with 6 to 30 carbon atoms, arylalkylamino group with 6 to 30 carbon atoms, heteroarylamino group with 2 to 24 carbon atoms, alkylsilyl group with 1 to 30 carbon atoms, arylsilyl group with 6 to 30 carbon atoms, alkyl group with 1 to 30 carbon atoms, alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 24 carbon atoms, aryl group with 7 to 30 carbon atoms, aryl group with 6 to 30 carbon atoms, heteroaryl group with 5 to 60 carbon atoms, and heteroarylalkyl group with 6 to 30 carbon atoms, the fusion of two adjacent substituents can form a ring.

[0025] In this specification, "halogen group" means fluorine, chlorine, bromine or iodine.

[0026] In this invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include methyl, ethyl, propyl, isobutyl, isopropyl, tert-butyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0027] In this invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples include vinyl, allyl, isopropenyl, and 2-butenyl, but it is not limited thereto.

[0028] In this invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples include ethynyl and 2-propynyl, but it is not limited to these.

[0029] In this invention, "alkylthio" refers to the alkyl group bonded by a sulfur bond (-S-).

[0030] In this invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon with 6 to 60 carbon atoms, consisting of a single ring or two or more rings bonded together. Additionally, it may include forms where two or more rings are laterally attached to each other or fused together. Examples of such aryl groups include phenyl, naphthyl, phenanthryl, anthraceneyl, dimethylfluorenyl, pyrene, terpenyl, etc., but are not limited thereto.

[0031] In this invention, "heteroaryl" refers to a monovalent substituent derived from a mono- or poly-heterocyclic aromatic hydrocarbon with 5 to 60 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S, or Se. Additionally, it may include forms in which two or more rings are pendant or fused together, and may also include forms fused with an aryl group. Examples of such heteroaryl groups include 6-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic groups such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazoyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto.

[0032] In this invention, "aryloxy group" is a monovalent substituent represented by RO-, where R refers to an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, and diphenoxy groups, but are not limited thereto.

[0033] In this invention, "alkyloxy" is a monovalent substituent represented by R'O-, where R' refers to an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of alkyloxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

[0034] In this invention, "aralkyl" refers to an aryl group and an alkyl group that is an aryl-alkyl group as described above. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenylethyl, and naphthylmethyl. The connection to the parent residue is formed via an alkyl group.

[0035] In this invention, "aromatic amino" refers to an amine that has been substituted with an aryl group.

[0036] In this invention, "heteroaromatic amino" refers to an amino group that has been substituted by an aryl or heterocyclic group.

[0037] In this invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0038] In this invention, "heterocyclic alkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon with 3 to 40 nuclear atoms, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S, or Se. Examples of such heterocyclic alkyl groups include morpholine and piperazine, but are not limited thereto.

[0039] In this invention, "alkylsilyl" refers to silyl groups substituted with alkyl groups having 1 to 40 carbon atoms, and "arylsilyl" refers to silyl groups substituted with aryl groups having 6 to 60 carbon atoms.

[0040] In this invention, "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0041] In this invention, "forming a ring by combining with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a fused ring thereof by combining with adjacent groups.

[0042] In this specification, "aliphatic hydrocarbon ring" refers to a non-aromatic ring composed only of carbon and hydrogen atoms.

[0043] Examples of "aromatic hydrocarbon rings" in this specification include phenyl, naphthyl, anthracene, etc., but are not limited to these.

[0044] In this specification, "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms.

[0045] In this specification, "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms.

[0046] In this specification, aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles can be monocyclic or polycyclic.

[0047] In this specification, "concentration quenching" refers to the decrease in the luminous efficiency of a device as the concentration of dopant molecules increases.

[0048] In this specification, "boron-based element", "boron-based compound", and "boron-based dopant" refer to the element boron (B) with atomic sequence 5, a compound containing boron, or a dopant.

[0049] According to an embodiment of the present invention, a compound represented by the following chemical formula 1 is provided as an organic compound for an organic electroluminescent element.

[0050] [Chemical Formula 1]

[0051]

[0052] Where Y is B, P (=O) or P (=S), X1 and X2 are the same or different from each other, and are independently selected from O, S, Se and N (R). 12 The group consisting of R1 to R 12 They may be the same as or different from each other, and each independently can be selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 carbon atoms, or substituted or unsubstituted carbon group with 6 to 30 carbon atoms. The group consisting of heteroarylalkyl groups, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino groups having 1 to 30 carbon atoms, substituted or unsubstituted arylamino groups having 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino groups having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, capable of combining with adjacent groups to form substituted or unsubstituted rings, R1 to R 12 At least one of them is a cyclic alkyl group having 3 to 20 carbon atoms, whether substituted or unsubstituted, in which case the R1 to R... 12The groups selected are respectively hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, aryloxy group with 6 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, alkylamino group with 1 to 30 carbon atoms, aromaticamino group with 6 to 30 carbon atoms, arylalkylamino group with 6 to 30 carbon atoms, and carbon atoms... The substance is substituted with one or more of the following groups: heteroarylamino with 2 to 24 carbon atoms, alkylsilyl with 1 to 30 carbon atoms, arylsilyl with 6 to 30 carbon atoms, alkyl with 1 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, alkynyl with 2 to 24 carbon atoms, aralkyl with 7 to 30 carbon atoms, aryl with 6 to 30 carbon atoms, heteroaryl with 5 to 60 carbon atoms, and heteroarylalkyl with 6 to 30 carbon atoms.

[0053] The compounds of Formula 1 according to the present invention contain at least one substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms. According to the present invention, Formula 1 contains at least one substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, thereby enabling the tuning of molecular polarity and minimizing π-π mutual attraction between molecules.

[0054] Therefore, when the compound of chemical formula 1 of the present invention is used excessively as a dopant, the concentration quenching phenomenon can also be suppressed. Furthermore, the compound of chemical formula 1 can prevent the formation of excimers and increase the electron density and stability of the nucleus. The luminous efficiency and lifetime of the device using the organic compound of the present invention can be improved.

[0055] Furthermore, the substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms that are replaced by the compounds of Formula 1 will not affect the energy level due to electron localization, and the stability of the film can be improved by increasing the melting point or glass transition temperature.

[0056] According to a preferred embodiment of the present invention, in the following chemical formula 1, Y is B, and X1 and X2 are each independently N(R) 12 ( ), which may be the same as or different from each other.

[0057] [Chemical Formula 1]

[0058]

[0059] According to an embodiment of the present invention, in the chemical formula 1, R1 to R3 may be the same as or different from each other, and each independently consists of the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms.

[0060] According to a preferred embodiment of the present invention, R1 to R3 may be the same as or different from each other, and may each be independently selected from the group consisting of hydrogen, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl and substituted or unsubstituted adamantyl. More preferably, at least one of R1 to R3 is substituted or unsubstituted cyclohexyl or substituted or unsubstituted adamantyl.

[0061] According to another embodiment of the present invention, in the chemical formula 1, R4 to R 11 They may be the same as or different from each other, and each independently can be selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, trimethylsilylethynyl (TMS), alkylthio (1 to 4 carbon atoms), alkylamino (1 to 10 carbon atoms), alkyl (1 to 10 carbon atoms), alkoxy (1 to 10 carbon atoms), cycloalkyl (1 to 30 carbon atoms), substituted or unsubstituted aryl (6 to 20 carbon atoms), substituted or unsubstituted heteroaryl (5 to 60 carbon atoms), substituted or unsubstituted heteroarylalkyl (6 to 20 carbon atoms). The group consisting of substituted or unsubstituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted alkylamino groups having 1 to 10 carbon atoms, substituted or unsubstituted arylamino groups having 6 to 20 carbon atoms, substituted or unsubstituted arylalkylamino groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylamino groups having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and substituted or unsubstituted aryloxy groups having 6 to 20 carbon atoms.

[0062] More specifically, R4 to R 11Each of the following is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, sec-butyl, tert-butyl, cyano, trifluoromethyl, fluoro, trimethylsilylethynyl (TMS), dimethylamino, diethylamino, methylthio, ethylthio, methoxy, ethoxy, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted naphthonaphthyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted substituted or unsubstituted phenothiazine, substituted or unsubstituted phenyloxazine, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted thiophenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted peryl, substituted or unsubstituted indole, substituted or unsubstituted furanyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxazolyl Diazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, and the group consisting of the following chemical formulas 2 to 6.

[0063] [Chemical Formula 2]

[0064]

[0065] [Chemical Formula 3]

[0066]

[0067] [Chemical Formula 4]

[0068]

[0069] [Chemical Formula 5]

[0070]

[0071] [Chemical Formula 6]

[0072]

[0073] In the above formula, X3 and X5 are S, O, N(R'), C(R')(R”) or Si(R')(R”); X4 is N, and each of R' and R” is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 20 carbon atoms. As an example, X3 and X5 are S, O, N-Ph, CH2, C(CH3)2 or Si(CH3)2; R' and R” are independently hydrogen, methyl, ethyl, propyl, phenyl, etc.

[0074] More preferably, R4 to R 11 One or more aryl groups having 6 to 20 carbon atoms, either substituted or unsubstituted, wherein the aryl substitution is selected from deuterium, methyl, ethyl, isopropyl, sec-butyl, tert-butyl, cyano, trifluoromethyl, fluoro, trimethylsilylethynyl (TMS), dimethylamino, diethylamino, methylthio, ethylthio, methoxy, ethoxy, phenoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, phenyl, naphthyl, anthracene, phenanthryl, naphthonaphthyl, pyrene, biphenyl, p-terphenyl, m-terphenyl, etc. The group consisting of 1 or more substituents, including phenthiazinyl, phenyloxazinyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, thiophenyl, triphenylene, peryl, indyl, furanyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, benzofuranyl, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, and one or more substituents from the group consisting of the following chemical formulas 2 to 13.

[0075] [Chemical Formula 2]

[0076]

[0077] [Chemical Formula 3]

[0078]

[0079] [Chemical Formula 4]

[0080]

[0081] [Chemical Formula 5]

[0082]

[0083] [Chemical Formula 6]

[0084]

[0085] [Chemical Formula 7]

[0086]

[0087] [Chemical Formula 8]

[0088]

[0089] [Chemical Formula 9]

[0090]

[0091] [Chemical Formula 10]

[0092]

[0093] [Chemical Formula 11]

[0094]

[0095] [Chemical Formula 12]

[0096]

[0097] [Chemical Formula 13]

[0098]

[0099] In the above formula, X3, X5, X8 to X 11 X4 is S, O, N(R'), C(R')(R”) or Si(R')(R”); X4 is N, and each of R' and R” is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 20 carbon atoms. As an example, X3, X5, X8 to X 11 It can be S, O, N-Ph, CH2, C(CH3)2 or Si(CH3)2; R' and R” can each be hydrogen, methyl, ethyl, propyl, phenyl, etc.

[0100] According to a preferred embodiment of the present invention, the compound represented by the chemical formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] The compound of Formula 1 of the present invention can be effectively used as a dopant material for the light-emitting layer. Specifically, the organic compound, as a dopant material, provides thermal stability and minimizes concentration quenching compared to existing boron-based dopants.

[0127] In addition, the present invention relates to materials for forming light-emitting layers containing the aforementioned organic compounds.

[0128] The material for forming the light-emitting layer may also include a host substance, which is a substance typically added when the organic compound is made into the form required to form the light-emitting layer.

[0129] The material used to form the light-emitting layer can be a dopant material.

[0130] In addition, the present invention relates to an organic electroluminescent element, wherein an organic thin film layer consisting of one or more layers including at least a light-emitting layer is laminated between the negative electrode and the positive electrode. In the organic electroluminescent element, the light-emitting layer comprises only one organic compound represented by the aforementioned chemical formula 1, or comprises a combination of two or more organic compounds.

[0131] The organic electroluminescent element may have a structure of a positive electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a negative electrode laminate. If necessary, an electron blocking layer, a hole blocking layer, etc., may also be further laminated.

[0132] The organic electroluminescent element of the present invention will be described below by way of example. However, the following examples do not limit the organic electroluminescent element of the present invention.

[0133] According to an embodiment of the present invention, an organic electroluminescent device is provided, comprising one or more light-emitting layers containing a compound represented by the chemical formula 1 as a dopant between a first electrode and a second electrode opposite to the first electrode. In addition to the light-emitting layer, it may further comprise an organic layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Specifically, the organic electroluminescent device of the invention may have a structure in which a positive electrode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), and a negative electrode (electron injection electrode) are laminated in sequence. Preferably, an electron blocking layer (EBL) may be further included between the positive electrode and the light-emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the negative electrode and the light-emitting layer. Additionally, a hole blocking layer (HBL) may be included between the negative electrode and the light-emitting layer.

[0134] As a method for manufacturing the organic electroluminescent element of the present invention, firstly, a positive electrode material is coated on the surface of a substrate using conventional methods to form a positive electrode. The substrate used is preferably a glass substrate or a transparent plastic substrate that exhibits excellent transparency, surface flatness, ease of handling, and water resistance. Furthermore, the positive electrode material can be transparent and possess excellent conductivity, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO).

[0135] Next, a hole injection layer (HIL) material is vacuum thermally vaporized or spin-coated onto the surface of the positive electrode using conventional methods to form a hole injection layer. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), or IDE406, which can be purchased from Idemitsu Corporation.

[0136] A hole transport layer (HTL) material is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating using conventional methods. Examples of hole transport layer materials include bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthyl-1-yl)-N,N'-biphenyl-benzidine (NPB), or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).

[0137] A light-emitting layer (EML) is formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating using conventional methods. In this case, the individual light-emitting material or the main light-emitting material used in the EML can be tris(8-hydroxyquinoline)aluminum (Alq3) for green light, and Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-bistyryl)-1,1'-biphenyl) series, spiro (Spiro) substances, spiro-DPVBi (spiro-4,4'-bis(2,2-bistyryl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)-phenol lithium salt), bis(bistyryl)benzene, aluminum-quinoline metal complexes, imidazole, thiazole, and oxazole metal complexes, etc.

[0138] The dopant in the luminescent layer material that can be used with the luminescent host is preferably the compound of the present invention as a blue fluorescent dopant. Other fluorescent dopants that can be used are IDE102 and IDE105, which are available from Idemitsu. As phosphorescent dopants, tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), bis[[(4,6-difluorophenyl)pyridyl-N,C-2']pyridinecarboxylic acid iridium(III) (FIrpic) (reference [ChihayaAdachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), platinum(II) octaethylporphyrin (PtOEP), TBE002 (Corbian Corporation), etc.

[0139] Optionally, an electron blocking layer (EBL) may be further formed between the hole transport layer and the light-emitting layer.

[0140] An electron transport layer (ETL) material is formed on the surface of the light-emitting layer by vacuum thermal evaporation or spin coating using conventional methods. There are no particular limitations on the electron transport layer material used; tris(8-hydroxyquinoline)aluminum (Alq3) is preferred.

[0141] Selectively, by further forming a hole blocking layer (HBL) between the emitting layer and the electron transport layer and using a phosphorescent dopant in the emitting layer, the diffusion of triplet excitons or holes into the electron transport layer can be prevented.

[0142] The hole blocking layer can be formed by vacuum thermal evaporation or spin coating of the hole blocking layer material using conventional methods. There are no particular restrictions on the hole blocking layer material, and preferred materials include (8-hydroxyquinolinyl)lithium (Liq), bis(8-hydroxy-2-methylquinolinyl)-biphenoxyaluminum (BAlq), bath copper (BCP), and LiF.

[0143] An electron injection layer is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating using conventional methods. The electron injection layer materials used include LiF, Liq, Li₂O, BaO, NaCl, and CsF.

[0144] The negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer using conventional methods.

[0145] At this point, the negative electrode material used can be lithium (Li), aluminum (Al), lithium aluminum (Al-Li), calcium (Ca), magnesium (Mg), magnesium indium (Mg-In), magnesium silver (Mg-Ag), etc. Additionally, the preceding light-emitting organic electroluminescent element can use indium tin oxide (ITO) or indium zinc oxide (IZO) to form a transparent negative electrode that allows light to pass through.

[0146] The following will provide representative examples illustrating the synthesis methods of the compounds. However, the synthesis methods of the compounds of the present invention are not limited to those described below; the compounds of the present invention can be obtained by the methods described below and methods known in the art.

[0147] Synthesis example 1

[0148]

[0149] Starting material 1 Compound 1

[0150] 10.6 g of starting material 1 (20 mmol) was dissolved in 250 ml of tert-butylbenzene and cooled to 0 °C. Under a nitrogen atmosphere, 24.7 ml of a 1.7 M tert-butyllithium solution (in pentane) (42 mmol) was added and the mixture was stirred at 60 °C for 2 hours.

[0151] The reactants were then cooled to 0°C again, and 4.0 mL of BBr3 (42 mmol) was added. The mixture was stirred at room temperature for 0.5 hours. The reactants were then cooled to 0°C again, and 7.3 mL of N,N-diisopropylethylamine (42 mmol) was added. The mixture was then stirred at 60°C for 2 hours.

[0152] The reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. After removing the solvent from the extracted organic layer, purification was performed by silica gel column chromatography (DCM / Hexane:DCM / n-hexane). Subsequently, after recrystallization purification with a DCM / acetone mixed solvent, 2.3 g of compound 1 was obtained in a yield of 23.2%.

[0153] MS(MALDI-TOF) m / z: 502[M]+

[0154] Synthesis example 2

[0155]

[0156] Starting material 70 Compound 70

[0157] Except that 12.1 g of starting material 70 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.2 g of the compound 70 was obtained in a yield of 10.2%.

[0158] MS(MALDI-TOF) m / z: 579[M]+

[0159] Synthesis example 3

[0160]

[0161] Starting material 92 Compound 92

[0162] Except that 11.4 g of starting material 92 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.6 g of the compound 92 was obtained in a yield of 15.0%.

[0163] MS(MALDI-TOF) m / z: 545[M]+

[0164] Synthesis example 4

[0165]

[0166] Starting material 120 Compound 120

[0167] Except that 14.4 g of starting material 120 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.8 g of the compound 120 was obtained in a yield of 13.3%.

[0168] MS(MALDI-TOF) m / z: 694[M]+

[0169] Synthesis example 5

[0170]

[0171] Starting material 133 Compound 133

[0172] Except that 13.9 g of starting material 133 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.7 g of the compound 133 was obtained in a yield of 12.5%.

[0173] MS(MALDI-TOF) m / z: 666[M]+

[0174] Synthesis example 6

[0175]

[0176] Starting material 158 Compound 158

[0177] Except that 15.6 g of starting material 158 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.6 g of the compound 158 was obtained in a yield of 17.3%.

[0178] MS(MALDI-TOF) m / z: 754 [M]+

[0179] Synthesis Example 7

[0180]

[0181] Starting material 167 Compound 167

[0182] Except that 17.3 g of starting material 167 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.9 g of the compound 167 was obtained in a yield of 11.5%.

[0183] MS(MALDI-TOF) m / z: 834[M]+

[0184] Synthesis example 8

[0185]

[0186] Starting material 168 Compound 168

[0187] Except that 17.2 g of starting material 168 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.7 g of the compound 168 was obtained in a yield of 16.4%.

[0188] MS(MALDI-TOF) m / z: 832[M]+

[0189] Synthesis example 9

[0190]

[0191] Starting material 251 Compound 251

[0192] Except that 16.1 g of starting material 251 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.4 g of the compound 251 was obtained in a yield of 15.2%.

[0193] MS(MALDI-TOF) m / z: 778[M]+

[0194] Synthesis example 10

[0195]

[0196] Starting material 304 Compound 304

[0197] Except that 14.9 g of starting material 304 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 0.6 g of the compound 304 was obtained in a yield of 4.4%.

[0198] MS(MALDI-TOF) m / z: 718[M]+

[0199] Synthesis example 11

[0200]

[0201] Starting material 401 Compound 401

[0202] Except that 16.1 g of starting material 401 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.6 g of the compound 401 was obtained in a yield of 16.6%.

[0203] MS(MALDI-TOF) m / z: 778[M]+

[0204] Synthesis example 12

[0205]

[0206] Starting material 454 Compound 454

[0207] Except that 15.3 g of starting material 454 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.6 g of the compound 454 was obtained in a yield of 17.7%.

[0208] MS(MALDI-TOF) m / z: 736[M]+

[0209] Synthesis example 13

[0210]

[0211] Starting material 459 Compound 459

[0212] Except that 15.0 g of starting material 459 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.8 g of the compound 459 was obtained in a yield of 19.1%.

[0213] MS(MALDI-TOF) m / z: 722[M]+

[0214] Synthesis example 14

[0215]

[0216] Starting material 462 Compound 462

[0217] Except that 15.0 g of starting material 462 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.6 g of the compound 462 was obtained in a yield of 18.0%.

[0218] MS(MALDI-TOF) m / z: 722[M]+

[0219] Synthesis Example 15

[0220]

[0221] Starting material 463 Compound 463

[0222] Except that 15.1 g of starting material 463 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 3.1 g of the compound 463 was obtained in a yield of 21.2%.

[0223] MS(MALDI-TOF) m / z: 726[M]+

[0224] Synthesis example 16

[0225]

[0226] Starting material 464 Compound 464

[0227] 16.1 g of starting material 464 (20 mmol) was dissolved in 250 mL of tert-butylbenzene and cooled to 0 °C. Under a nitrogen atmosphere, 24.7 mL of a 1.7 M tert-butyllithium solution (in pentane) (42 mmol) was added, and the mixture was stirred at 60 °C for 2 hours. The mixture was then cooled back to 0 °C, and 4.0 mL of BBr3 (42 mmol) was added, followed by stirring at room temperature for 0.5 hours. The mixture was then cooled back to 0 °C, and 7.3 mL of N,N-diisopropylethylamine (42 mmol) was added, followed by stirring at 60 °C for 2 hours. The reaction mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. After removing the solvent from the extracted organic layer, purification was performed using silica gel column chromatography (DCM / Hexane: DCM / n-hexane). Subsequently, after recrystallization purification using a DCM / acetone mixed solvent, 3.2 g of the compound 464 was obtained in a yield of 20.7%.

[0228] MS(MALDI-TOF) m / z: 778[M]+

[0229] Synthesis Example 17

[0230]

[0231] Starting material 465 Compound 465

[0232] *The same method as in Synthesis Example 1 was used except that 13.1 g of starting material 465 was used instead of starting material 1, and 1.2 g of the compound 465 was obtained in 9.9% yield.

[0233] MS(MALDI-TOF) m / z: 626[M]+

[0234] Synthesis Example 18

[0235]

[0236] Starting material 467 Compound 467

[0237] Except that 13.6 g of starting material 467 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.1 g of the compound 467 was obtained in a yield of 8.3%.

[0238] MS(MALDI-TOF) m / z: 654 [M]+

[0239] Synthesis example 19

[0240]

[0241] Starting material 469 Compound 469

[0242] Except that 15.1 g of starting material 469 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.7 g of the compound 469 was obtained in a yield of 15.5%.

[0243] MS(MALDI-TOF) m / z: 726[M]+

[0244] Synthesis example 20

[0245]

[0246] Starting material 475 Compound 475

[0247] Except that 17.7 g of starting material 475 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 3.5 g of the compound 475 was obtained in a yield of 20.1%.

[0248] MS(MALDI-TOF) m / z: 858[M]+

[0249] Synthesis Example 21

[0250]

[0251] Starting material 477 Compound 477

[0252] Except that 14.7 g of starting material 477 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.4 g of the compound 477 was obtained in a yield of 16.6%.

[0253] MS(MALDI-TOF) m / z: 558[M]+

[0254] Synthesis example 22

[0255]

[0256] Starting material 505 Compound 505

[0257] Except that 15.0 g of starting material 505 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.7 g of the compound 505 was obtained in a yield of 18.8%.

[0258] MS(MALDI-TOF) m / z: 722[M]+

[0259] Synthesis example 23

[0260]

[0261] Starting material 509 Compound 509

[0262] Except that 13.3 g of starting material 509 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.3 g of the compound 509 was obtained in a yield of 17.8%.

[0263] MS(MALDI-TOF) m / z: 640[M]+

[0264] Synthesis example 24

[0265]

[0266] Starting material 511 Compound 511

[0267] Except that 14.5 g of starting material 511 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.8 g of the compound 511 was obtained in a yield of 20.4%.

[0268] MS(MALDI-TOF) m / z: 696[M]+

[0269] Synthesis example 25

[0270]

[0271] Starting material 512 Compound 512

[0272] Except that 15.5 g of starting material 512 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 3.2 g of the compound 512 was obtained in a yield of 21.1%.

[0273] MS(MALDI-TOF) m / z: 748[M]+

[0274] Synthesis Example 26

[0275]

[0276] Starting material 513 Compound 513

[0277] Except that 16.9 g of starting material 513 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 3.0 g of the compound 513 was obtained in a yield of 18.2%.

[0278] MS(MALDI-TOF) m / z: 818[M]+

[0279] Synthesis Example 27

[0280]

[0281] Starting material 514 Compound 514

[0282] Except that 14.4 g of starting material 514 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.7 g of the compound 514 was obtained in a yield of 19.5%.

[0283] MS(MALDI-TOF) m / z: 694[M]+

[0284] Synthesis example 28

[0285]

[0286] Starting material 515 Compound 515

[0287] Except that 13.9 g of starting material 515 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.6 g of the compound 515 was obtained in a yield of 19.2%.

[0288] MS(MALDI-TOF) m / z: 670 [M]+

[0289] Synthesis Example 29

[0290]

[0291] Starting material 516 Compound 516

[0292] Except that 16.6 g of starting material 516 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.9 g of the compound 516 was obtained in a yield of 17.8%.

[0293] MS(MALDI-TOF) m / z: 800[M]+

[0294] Synthesis example 30

[0295]

[0296] Starting material 517 Compound 517

[0297] Except that 14.5 g of starting material 517 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.1 g of the compound 517 was obtained in a yield of 15.4%.

[0298] MS(MALDI-TOF) m / z: 696[M]+

[0299] Synthesis example 1

[0300]

[0301] Starting material 518 Compound 518

[0302] Except that 16.1 g of starting material 518 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.9 g of the compound 518 was obtained in a yield of 18.3%.

[0303] MS(MALDI-TOF) m / z: 778[M]+

[0304] Synthesis example 32

[0305]

[0306] Starting material 586 Compound 586

[0307] Except that 11.6 g of starting material 586 was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 0.9 g of the compound 586 was obtained in a yield of 8.4%.

[0308] MS(MALDI-TOF) m / z: 552[M]+

[0309] Comparative Example 1 - Synthesis of Compound A

[0310]

[0311] Starting material A, compound A

[0312] Except that starting material A was used instead of starting material 1, 13.4 g of the compound A was used in the same manner as in Synthesis Example 1, and 2.7 g of the compound A was obtained in a yield of 21.7%.

[0313] MS(MALDI-TOF) m / z: 644[M]+

[0314] Comparative Example 2 - Synthesis of Compound B

[0315]

[0316] Starting material B, compound B

[0317] Except that starting material B was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 2.0 g of the compound was obtained in 18.5% yield.

[0318] MS(MALDI-TOF) m / z: 532[M]+

[0319] Comparative Example 3 - Synthesis of Compound C

[0320]

[0321] Starting material C compound C

[0322] Except that 8.9 g of starting material C was used instead of starting material 1, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.7 g of the compound C was obtained in a yield of 20.2%.

[0323] MS(MALDI-TOF) m / z: 420[M]+

[0324] Comparative Example 4 - Synthesis of Compound D

[0325]

[0326] Starting material D, compound D

[0327] Except for using 10.4 g of starting material D, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.3 g of the compound D was obtained in a yield of 12.7%.

[0328] MS(MALDI-TOF) m / z: 492[M]+

[0329] Comparative Example 5 - Synthesis of Compound E

[0330]

[0331] Starting material E, compound E

[0332] Except for using 12.4 g of starting material E, the same method as in Synthesis Example 1 was used to conduct the experiment, and 1.9 g of the compound E was obtained in a yield of 16.4%.

[0333] MS(MALDI-TOF) m / z: 592[M]+

[0334] Example

[0335] <Manufacturing Method of Back-Emitting Organic Electroluminescent Element>

[0336] Using photolithography, an ITO (100 nm) substrate, on which the positive electrode of the organic electroluminescent element is laminated, is divided into negative and positive electrode regions and an insulating layer, and patterned. Then, to improve the work function of the positive electrode (ITO) and for cleaning, ultraviolet ozone treatment and surface treatment with O2:N2 plasma are performed. A hole injection layer (HIL) with a thickness of 10 nm is formed on top of this. Next, a hole transport layer with a thickness of 60 nm is formed by vacuum evaporation on top of the hole injection layer (HTL), and an electron blocking layer (EBL) with a thickness of 5 nm is formed on top of the hole transport layer (HTL). The main body of a blue emitting layer is deposited on top of the electron blocking layer (EBL), and simultaneously, 3% of compound 463 is doped as a dopant to form an emitting layer (EML) with a thickness of 25 nm.

[0337] A 25nm electron transport layer (ETL) is deposited on top of the organic light-emitting element (OLED), followed by a 1nm electron injection layer. A 100nm layer of aluminum is then deposited as the cathode. A seal cap containing a getter is then bonded to the OLED using a UV-curable adhesive to protect it from atmospheric oxygen or moisture, thus fabricating the OLED.

[0338] Examples 2 to 22: Fabrication of Organic Electroluminescent Devices

[0339] Organic electroluminescent elements were fabricated using the same method as in Example 1, except that compounds 464, 505, 515, 517, 251, 133, 511, 516, 514, 1, 512, 465, 469, 459, 462, 477, 509, 513, 518, and 586 were used instead of compound 463 as dopants.

[0340] Comparative Examples 1 to 5: Fabrication of Organic Electroluminescent Devices

[0341] The organic electroluminescent element was fabricated using the same method as in Example 1, except that compounds A to E were used instead of compound 463 as a dopant.

[0342] Characteristic analysis of organic electroluminescent devices

[0343] Hereinafter, the back-emitting organic electroluminescent devices manufactured in Examples 1 to 22 and Comparative Examples 1 to 5 are subjected to an A / cm² pressure of 10 mA / cm². 2 The current was used to measure the electro-optic properties, and the results are shown in Table 1 below.

[0344] [Table 1]

[0345]

[0346] As can be seen from the results in Table 1, the luminous efficiency of the components in the embodiments is superior compared to that of the components in the comparative examples.

[0347] <Manufacturing Method of Organic Electroluminescent Element with Front-Emitting Light Structure>

[0348] A substrate, consisting of a 10nm Ag alloy (as a light-reflecting layer) and a 50nm ITO (as the positive electrode of an organic electroluminescent element), was sequentially laminated using a photolithography process. This was divided into negative and positive electrode regions, along with an insulating layer, and then patterned. To improve the work function of the ITO and for cleaning, ultraviolet ozone treatment and O2:N2 plasma surface treatment were performed. A hole injection layer (HIL) with a thickness of 10nm was then formed on top of this substrate. Next, a hole transport layer with a thickness of 110nm was vacuum-deposited on top of the hole injection layer (HTL), and an electron blocking layer (EBL) with a thickness of 15nm was formed on top of the hole transport layer (HTL). The main body of a blue emitting layer was then deposited on top of the electron blocking layer (EBL), and simultaneously, 1-5% dopant was added to form a 20nm emitting layer (EML).

[0349] A 30nm electron transport layer (ETL) is deposited on top of the negative electrode, and magnesium (Mg) and silver (Ag) are deposited in a 9:1 ratio to form a 17nm thick negative electrode. After depositing a capping layer (CPL) on the negative electrode, a seal cap containing a getter is bonded to it using a UV-curable adhesive to protect the organic light-emitting element from atmospheric oxygen or moisture, thus fabricating the organic light-emitting element.

[0350] Characteristic analysis of organic electroluminescent devices

[0351] Hereinafter, the compounds of Examples 2, 4, 5, and 6 and the compound of Comparative Example 1 (compound A) were applied to the organic electroluminescent element with the above-mentioned light-emitting structure, and the relationship between doping concentration and luminous efficiency (doping concentration dependence) was measured and compared. The results are shown in Tables 2 and 3 below.

[0352] According to Table 2 below, in Comparative Example 1-1, the luminous efficiency decreased with increasing doping concentration when compound A was used. Conversely, it can be seen that the luminous efficiency remained constant in Examples 2-1 to 6-1. This indicates that the luminous efficiency of the present invention is not affected by the doping concentration.

[0353] [Table 2]

[0354]

[0355] [Table 3]

[0356]

[0357] According to Table 3 below, in Comparative Example 1-1, it can be seen that the luminous efficiency decreases with increasing concentration when compound A is used, while it remains constant in Examples 2-1 to 6-1. This indicates that the luminous efficiency of the present invention is not affected by the doping concentration. From the results in Tables 2 and 3, it can be seen that, compared with unsubstituted cycloalkyl compounds, the boron-based compounds with substituted cycloalkyl groups of the present invention minimize concentration quenching and exhibit the smallest change in lifetime decay with increasing doping concentration.

[0358] This invention is not limited to the embodiments described, and can be made in various different forms. Those skilled in the art will understand that it can be implemented in other specific forms without altering the technical concept or essential features of the invention. Therefore, it should be understood that the above embodiments are exemplary in all respects and not restrictive.

Claims

1. A compound selected from the group consisting of: ， ， ， 。 2. An organic electroluminescent element, characterized in that, include: First electrode; A second electrode is disposed opposite to the first electrode; and one or more organic layers are disposed between the first electrode and the second electrode. The organic layer comprises the compound of claim 1.

3. The organic electroluminescent element according to claim 2, characterized in that, The organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

4. The organic electroluminescent element according to claim 3, characterized in that, The organic layer is a light-emitting layer.

5. The organic electroluminescent element according to claim 4, characterized in that, The light-emitting layer contains the compound of claim 1 as a dopant.

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