Compound and organic electroluminescent element comprising same

Abstract

The present invention relates to a compound and an organic electroluminescent element comprising the same. The present invention relates to: a novel dibenzofuran-based compound having excellent thermal stability, carrier transport ability, light-emitting ability, and the like; and an organic electroluminescent element having a low driving voltage and improved luminous efficiency, lifespan characteristics, and the like by comprising the same as a material of one or more organic material layers.

Description

[0001] This application is a divisional application of the Chinese patent application with the application date of July 9, 2018, application number 201880046686.4, and invention name "Organic compounds and organic electroluminescent elements containing the same". Technical Field

[0002] The present invention relates to a novel organic compound and an organic electroluminescent element containing the same, and more specifically, to a novel dibenzofuran compound having excellent thermal stability, carrier transport ability, luminescence ability, etc., and an organic electroluminescent element having low driving voltage, improved luminescence efficiency, life characteristics, etc. by containing the compound as a material for one or more organic layers. Background Art

[0003] Starting from Bernanose's observation of organic thin film luminescence in the 1950s, research was conducted on organic electroluminescent (EL) elements (hereinafter referred to as "organic EL elements") developed from the blue electroluminescence of anthracene single crystals in 1965. Subsequently, in 1987, Tang proposed an organic EL element with a two-layer stacked structure consisting of a hole layer (NPB) and a light-emitting layer (Alq3).

[0004] Later, in order to achieve the high efficiency and long life characteristics required for commercialization of organic EL elements, a multilayer stacked structure with unique characteristics and subdivided functions was proposed, such as an organic layer that performs hole injection and transport functions, an organic layer that performs electron injection and transport functions, and an organic layer that induces electroluminescence by the combination of holes and electrons.

[0005] Regarding organic electroluminescent elements, if a voltage is applied between two electrodes, 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 and electrons meet, excitons are formed, and when the excitons transition to the ground state, light is emitted. The substances contained in the above-mentioned organic layer can be divided into luminescent substances, hole injection substances, hole transport substances, electron transport substances, electron injection substances, etc. according to their functions.

[0006] The electron spin of the exciton formed by the recombination of electrons and holes is generated at a ratio of 25% for singlet excitons and 75% for triplet excitons. At this time, the organic EL element can be divided into a fluorescent EL element in which the singlet exciton contributes to the emission of light and a phosphorescent EL element in which the triplet exciton contributes to the emission of light, according to the type of electron spin of the exciton formed.

[0007] It is generally believed that the internal quantum efficiency of a fluorescent EL element that emits light by means of singlet excitons will not exceed 25% theoretically depending on the generation ratio, and the upper limit of the external quantum efficiency is 5%.

[0008] When a phosphorescent EL element that emits light by triplet excitons uses a metal complex containing heavy atoms of a transition metal such as Ir or Pt as a phosphorescent dopant, the light emission efficiency can be improved by up to four times compared to fluorescence.

[0009] Thus, phosphorescent EL elements theoretically show higher efficiency in terms of luminous efficiency than fluorescent elements. However, unlike green and red phosphorescent elements, blue phosphorescent elements are not developed enough in terms of deep blue color purity, efficient phosphorescent dopants, and hosts with wide energy band gaps, so they cannot be commercialized, and blue fluorescent elements are used in products instead.

[0010] As the performance of organic EL elements has been improved to the point of commercialization due to the introduction of a multi-layer stacked structure, efforts are being made to expand their application range, starting with automotive radio display products in 1997, to portable information display devices and TV display elements.

[0011] In addition, in recent years, due to the trend of larger and higher resolution displays, it is required to develop organic EL elements with high efficiency and long life. In particular, the high resolution of the display can only be achieved when more pixels are formed in the same area. Due to such high resolution, the light-emitting area of ​​the organic EL pixel is reduced, resulting in a shortened life, which has become the most important technical issue that organic EL elements have to overcome.

[0012] However, the glass transition temperature of the materials of conventional organic EL elements is low and the thermal stability is reduced, so the life of the organic electroluminescent elements cannot reach a satisfactory level and the light emitting characteristics also need to be improved. Summary of the invention

[0013] Technical issues

[0014] An object of the present invention is to provide a novel compound which has excellent thermal stability, carrier transport ability, and luminescence ability and can be used as a light-emitting layer material, a hole transport layer material, a light-emitting auxiliary layer material, or an electron transport auxiliary layer material.

[0015] Another object of the present invention is to provide an organic electroluminescent device comprising the novel compound and having low driving voltage, high luminous efficiency, and improved life characteristics.

[0016] Solution to the problem

[0017] The present invention provides a compound represented by the following chemical formula 1:

[0018] [Chemical formula 1]

[0019]

[0020] [Chemical formula 2]

[0021]

[0022] in,

[0023] X1 is selected from O, S, C (R9) (R 10 ) and N(R 11 ),

[0024] At least one group of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, and R7 and R8 is condensed with the ring represented by the above chemical formula 2 to form a condensed ring,

[0025] R1, R2, R3, R4, R5, R6, R7 and R8 which do not form a condensed ring with the ring represented by the above chemical formula 2 are the same as or different from each other, and each independently can be selected from hydrogen, deuterium, C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or combined with adjacent groups to form a condensed ring,

[0026] The dotted line in the above chemical formula 2 is the part that forms a condensation with the chemical formula 1.

[0027] X2 and X3 are the same or different and are independently selected from hydrogen, deuterium, C1-C2 alkyl and C6-C 60 The aromatic group,

[0028] L is selected from a single bond, C6~C 18and a heteroarylene group having 5 to 18 atomic nuclei,

[0029] R9 to R 11 are the same or different from each other and are independently selected from hydrogen, deuterium, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0030] R 12 Choose from C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Mono- or diarylphosphonyl, and C6~C 60 A group consisting of arylamine groups,

[0031] R1 to R 12 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, mono- or diarylphosphono, and arylamine groups of X2 and X3 can be independently selected from C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Mono- or diarylphosphonyl, and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents in the group consisting of the arylamine group. When the arylamine group is substituted with a plurality of substituents, they may be the same as or different from each other.

[0032] The present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound of Chemical Formula 1.

[0033] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0034] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0035] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0036] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached to each other (pendant) or condensed. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, etc.

[0037] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having a nucleus number of 5 to 60. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other, and further may include a form condensed with an aromatic group. Examples of such heteroaryl groups include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0038] In the present invention, "aryloxy" means a monovalent substituent represented by RO-, wherein R is an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, and diphenoxy.

[0039] In the present invention, "alkoxy" means a monovalent substituent represented by R'O-, wherein R' is an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, and the like.

[0040] In the present invention, the "arylamino group" means an amine group substituted with an aryl group having 6 to 60 carbon atoms.

[0041] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0042] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include morpholinyl and piperidinyl, but are not limited thereto.

[0043] In the present invention, an "alkylsilyl group" means a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and an "arylsilyl group" means a silyl group substituted by an aryl group having 6 to 60 carbon atoms.

[0044] In the present invention, the "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle or a combination thereof.

[0045] Effects of the Invention

[0046] The compound provided by the present invention has excellent thermal stability, carrier transport ability and luminescence ability, and can therefore be effectively used as an organic layer material of an organic electroluminescent element.

[0047] In addition, an organic electroluminescent element in which the compound of the present invention is added to an organic layer has excellent luminescent performance, low driving voltage, high efficiency and long life, and can be effectively applied to full-color display panels and the like. DETAILED DESCRIPTION

[0048] Hereinafter, the present invention will be described.

[0049] 1. New organic compounds

[0050] The present invention provides a novel compound having excellent thermal stability, carrier transport capability, luminescence capability and the like.

[0051] Specifically, the novel organic compound of the present invention has a structure in which an indene moiety or the like is condensed with a hetero compound to form a basic skeleton, and various substituents are bonded or condensed to the basic skeleton.

[0052] Preferably, the novel organic compound of the present invention can be represented by the following Chemical Formula 1:

[0053] [Chemical formula 1]

[0054]

[0055] [Chemical formula 2]

[0056]

[0057] in,

[0058] X1 is selected from O, S, C (R9) (R 10 ) and N(R 11 ),

[0059] At least one group of R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, and R7 and R8 is condensed with the ring represented by the above chemical formula 2 to form a condensed ring,

[0060] R1, R2, R3, R4, R5, R6, R7 and R8 which do not form a condensed ring with the ring represented by the above chemical formula 2 are the same as or different from each other, and each independently can be selected from hydrogen, deuterium, C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or combined with adjacent groups to form a condensed ring,

[0061] The dotted line in the above chemical formula 2 is the part that forms a condensation with the chemical formula 1.

[0062] X2 and X3 are the same or different and are independently selected from hydrogen, deuterium, C1-C2 alkyl and C6-C 60 The aromatic group,

[0063] L is selected from a single bond, C6~C 18 and a heteroarylene group having 5 to 18 atomic nuclei,

[0064] R9 to R 11 are the same or different from each other and are independently selected from hydrogen, deuterium, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0065] R 12 Choose from C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Mono- or diarylphosphonyl, and C6~C 60 A group consisting of arylamine groups,

[0066] R1 to R 12 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, mono- or diarylphosphono, and arylamine groups of X2 and X3 can be independently selected from C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Mono- or diarylphosphonyl, and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents in the group consisting of the arylamine group. When the arylamine group is substituted with a plurality of substituents, they may be the same as or different from each other.

[0067] More specifically, the novel organic compound of the present invention has a structure in which an indene moiety or the like is condensed with a compound composed of dibenzofuran, dibenzothiophene, fluorene or carbazole to form a basic skeleton, preferably an indene moiety or the like is condensed with dibenzofuran to form a basic skeleton and various substituents are bonded or condensed.

[0068] According to a preferred embodiment of the present invention, the above Chemical Formula 1 can be represented by the following Chemical Formulas 3 to 8:

[0069] [Chemical formula 3]

[0070]

[0071] [Chemical formula 4]

[0072]

[0073] [Chemical formula 5]

[0074]

[0075] [Chemical formula 6]

[0076]

[0077] [Chemical formula 7]

[0078]

[0079] [Chemical formula 8]

[0080]

[0081] in,

[0082] X1 to X3, L and R1 to R8 are respectively the same as defined in the above Chemical Formula 1.

[0083] According to a preferred embodiment of the present invention, X1 in the above Chemical Formulae 1 to 8 may be O.

[0084] According to a preferred embodiment of the present invention, X2 and X3 in the above Chemical Formulae 1 to 8 may be methyl groups.

[0085] According to a preferred embodiment of the present invention, R 12 The substituent may be any one of the following Chemical Formulas 9 to 11:

[0086] [Chemical formula 9]

[0087]

[0088] [Chemical formula 10]

[0089]

[0090] [Chemical formula 11]

[0091]

[0092] in,

[0093] * means the combined part,

[0094] n is an integer from 0 to 2,

[0095] Y1 to Y3 are the same or different from each other and are each independently C(R 15 ) or N, and at least one of them is N,

[0096] Y4 to Y7 are the same or different from each other and are each independently C(R 16 ) or N,

[0097] X4 is selected from O, S, C (R 17 )(R 18 )、Si(R 19 )(R 20 ) and N(R 21 ),

[0098] R 12 To R 14 are the same or different from each other and are independently selected from hydrogen, deuterium, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0099] R 15 and R 16 The same or different from each other, each independently can be selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or combined with adjacent groups to form a condensed ring,

[0100] R 17 To R 21 The same or different from each other, each independently can be selected from C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 or combined with adjacent groups to form a condensed ring,

[0101] R 12 To R 21 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, mono- or diarylphosphono, and arylamine groups can be independently selected from C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Mono- or diarylphosphonyl, and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents in the group consisting of the arylamine group. When the arylamine group is substituted with a plurality of substituents, they may be the same as or different from each other.

[0102] According to a preferred embodiment of the present invention, the above L may be a single bond, a phenylene group or a biphenylene group.

[0103] According to a preferred embodiment of the present invention, the compound represented by the above Chemical Formula 1 may be a compound characterized by being selected from the group consisting of the following compounds:

[0104] The compound represented by the above Chemical Formula 1 is a compound selected from the group consisting of the following compounds:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] The compound of Chemical Formula 1 of the present invention can be synthesized by a general synthesis method (see Chem. Rev., 60: 313 (1960); J. Chem. Soc. 4482 (1955); Chem. Rev. 95: 2457 (1995) etc.). The detailed synthesis process of the compound of the present invention will be specifically described in the synthesis examples described below.

[0139] 2. Organic electroluminescent elements

[0140] In addition, another aspect of the present invention provides an organic electroluminescent device including the compound represented by the above Chemical Formula 1.

[0141] Specifically, the organic electroluminescent element of the present invention comprises (i) an anode, (ii) a cathode, and (iii) one or more organic layers between the anode and the cathode, and at least one of the organic layers comprises the compound represented by the chemical formula 1. In this case, the compound represented by the chemical formula 1 can be used alone or in combination of two or more.

[0142] According to one example of the present invention, the above-mentioned one or more organic layers may include any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic layer may include the compound represented by the above Chemical Formula 1.

[0143] Preferably, the organic layer containing the compound represented by the above chemical formula 1 can be a light-emitting layer or a hole transport layer. More preferably, when the light-emitting layer contains the compound represented by the above chemical formula 1, the luminous efficiency, brightness, power efficiency, thermal stability and element life of the organic electroluminescent element can be greatly improved.

[0144] For example, the compound represented by the above Chemical Formula 1 can be a phosphorescent host, a fluorescent host or a dopant material of the light-emitting layer, and preferably can be a phosphorescent host of the light-emitting layer.

[0145] According to another example of the present invention, the above-mentioned one or more organic layers may include any one or more of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer and an electron injection layer. In this case, at least one organic layer may include the compound represented by the above Chemical Formula 1.

[0146] Preferably, the organic layer containing the compound represented by the above chemical formula 1 can be a light-emitting auxiliary layer. In particular, when the light-emitting auxiliary layer material of the organic electroluminescent element contains the compound represented by the above chemical formula 1, the efficiency (luminous efficiency and power efficiency), life and brightness of the organic electroluminescent element can be further improved, and the driving voltage can be further reduced.

[0147] According to another example of the present invention, the above-mentioned one or more organic layers may include one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. In this case, at least one organic layer may include the compound represented by the above Chemical Formula 1.

[0148] Preferably, the organic layer containing the compound represented by the above chemical formula 1 may be an electron transport auxiliary layer. In particular, when the electron transport auxiliary layer of the organic electroluminescent element contains the compound represented by the above chemical formula 1, the efficiency (luminous efficiency and power efficiency), life and brightness of the organic electroluminescent element can be further improved, and the driving voltage can be further reduced.

[0149] The structure of the organic electroluminescent element of the present invention is not particularly limited, and may be, for example, a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0150] According to one example, the organic electroluminescent element may be a structure in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode are stacked in sequence on a substrate. As needed, a light-emitting auxiliary layer may be inserted between the hole transport layer and the light-emitting layer. In addition, an electron injection layer may also be provided on the electron transport layer.

[0151] The organic electroluminescent element of the present invention can be formed and manufactured by materials and methods known in the art, in addition to being formed in a manner that at least one of the above-mentioned one or more organic layers, such as a light-emitting layer or a light-emitting auxiliary layer, contains the compound represented by the above-mentioned Chemical Formula 1.

[0152] The organic layer may be formed by vacuum deposition or solution coating, and examples of the solution coating method include spin coating, dip coating, blade coating, inkjet printing, thermal transfer, etc., but are not limited thereto.

[0153] Examples of the substrate that can be used when producing the organic electroluminescent element in the present invention include, but are not limited to, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, and the like.

[0154] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; or carbon black, but are not limited to these.

[0155] In addition, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0156] Furthermore, the materials used for the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and any common materials known in the art can be used without limitation.

[0157] Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are merely illustrative of the present invention and the present invention is not limited to the following examples.

[0158] [Preparation Example 1] Synthesis of Compounds Inv 1 and Inv 2

[0159]

[0160] <Step 1> Synthesis of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0161] After 2-bromodibenzo[b,d]furan (94 g, 0.38 mol), bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl2 (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) were added to the flask, 1,4-dibromo[b,d]furan (94 g, 0.38 mol) was added to the flask. alkane (2L) was added and dissolved, and then heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain the compound 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (73g, yield 62%).

[0162] <Step 2> Synthesis of methyl 5-chloro-2-(dibenzo[b,d]furan-2-yl)benzoate

[0163] 2-(Dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22.6 g, 76.9 mmol), methyl 2-bromo-5-chlorobenzoate (21.1 g, 84.57 mmol) and Pd(PPh3)4 (0.89 g, 0.769 mmol) obtained in <Step 1> were added to a flask and dissolved in 1,4-dioxaborolane under a nitrogen atmosphere. After 257 mL of alkane, 128 ml of an aqueous solution in which 17 g (115.3 mmol) of K2CO3 was dissolved was added, and then the mixture was refluxed and stirred at 70°C for 8 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, dried with Na2SO4, and distilled under reduced pressure, and then purified by column chromatography to obtain 21.8 g (yield 84%) of the compound 5-chloro-2-(dibenzo[b,d]furan-2-yl)benzoic acid methyl ester.

[0164] <Step 3> Synthesis of Compounds Inv 1 and Inv 2

[0165] In a three-necked round-bottom flask dried by heating under vacuum, 21.8 g (64.95 mmol) of methyl 5-chloro-2-(dibenzo[b, d]furan-2-yl)benzoate obtained in <Step 2> was added under a nitrogen atmosphere, and 325 mL of THF was added to dissolve it, then cooled to -10°C and stirred. 54 mL of 3.0 M CH3MgBr (in ether, 162.4 mmol) was slowly added thereto over 30 minutes. The reaction solution was warmed to room temperature and stirred for 12 hours under a nitrogen atmosphere. After the reaction solution was cooled to 0°C, an aqueous solution prepared by dissolving 100 mL of distilled water in NH4Cl (10.4 g, 194.85 mmol) was slowly added thereto. The reaction solution was extracted with distilled water and ether, the organic layer solution was dried over Na2SO4, and the filtrate was concentrated under reduced pressure after filtration. After the dried residue was added to a three-necked round-bottom flask, 325 mL of CH2Cl2 was added under a nitrogen atmosphere, and after dissolving, it was cooled to 0°C and stirred. Boron trifluoride ether (4 mL, 32.5 mmol) was slowly added thereto over 10 minutes, and after warming to room temperature, it was stirred for 12 hours. After the reaction was completed, sodium bicarbonate aqueous solution was slowly added at 0°C and stirred for 30 minutes. The extract extracted with dichloromethane / distilled water was dried over Na2SO4, distilled under reduced pressure, and refined by column chromatography to obtain compound Inv 1 (10.3 g, yield 50%) and compound Inv 2 (9.3 g, yield 45%).

[0166] [Preparation Example 2] Synthesis of Compounds Inv 3 and Inv 4

[0167]

[0168] <Step 1> Synthesis of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0169] After 2-bromodibenzo[b,d]furan (94 g, 0.38 mol), bis(pinacolato)diboron (115.8 g, 0.46 mol), Pd(dppf)Cl2 (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) were added to the flask, 1,4-dibromo[b,d]furan (94 g, 0.38 mol) was added to the flask. After dissolving in alkane (2L), heating and stirring were performed for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain the compound 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73g, yield 62%).

[0170] <Step 2> Synthesis of methyl 4-chloro-2-(dibenzo[b,d]furan-2-yl)benzoate

[0171] The 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69 g, 0.235 mol), 2-bromo-4-chloro-1-nitrobenzene (67 g, 0.282 mol) and Pd(PPh3)4 (13.5 g, 0.011 mol) obtained in the above <Step 1> were added to a flask, and a 2M Na2CO3 saturated aqueous solution (352 ml) and 1,4-dioxaborolane were added thereto. After dissolving in 1,4-dioxane (2L), the mixture was heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain the compound 4-chloro-2-(dibenzo[b,d]furan-2-yl)benzoic acid methyl ester (71g, yield 91%).

[0172] <Step 3> Synthesis of compounds Inv 3 and Inv 4

[0173] In a three-necked round-bottom flask dried by heating under vacuum, 21.8 g (64.95 mmol) of methyl 4-chloro-2-(dibenzo[b, d]furan-2-yl)benzoate obtained in <Step 2> was added under a nitrogen atmosphere, and 325 mL of THF was added to dissolve it, then cooled to -10°C and stirred. 54 mL of 3.0 M CH3MgBr (in ether, 162.4 mmol) was slowly added thereto over 30 minutes. The reaction solution was warmed to room temperature and stirred for 12 hours under a nitrogen atmosphere. After the reaction solution was cooled to 0°C, an aqueous solution prepared by dissolving 100 mL of distilled water in NH4Cl (10.4 g, 194.85 mmol) was slowly added thereto. The reaction solution was extracted with distilled water and ether, the organic layer solution was dried over Na2SO4, and the filtrate was concentrated under reduced pressure after filtration. After the dried residue is added to a three-necked round-bottom flask, 325 mL of CH2Cl2 is added under a nitrogen atmosphere, and after dissolving, it is cooled to 0 ° C and stirred. Boron trifluoride ether (4 mL, 32.5 mmol) is slowly added thereto over 10 minutes, and after warming to room temperature, it is stirred for 12 hours. After the reaction is completed, sodium bicarbonate aqueous solution is slowly added at 0 ° C and stirred for 30 minutes. The extract extracted with dichloromethane / distilled water is dried over Na2SO4, distilled under reduced pressure, and refined by column chromatography to obtain compound Inv 3 (9.3 g, yield 45%) and compound Inv 4 (8.2 g, yield 39%).

[0174] [Preparation Example 5] Synthesis of Compounds Inv 5 and Inv 6

[0175]

[0176] The same process as in Preparation Example 1 was carried out except that 3-bromodibenzo[b,d]furan was used instead of 2-bromodibenzo[b,d]furan in <Step 1> to obtain Compound Inv 5 (9.0 g, yield 43%) and Compound Inv 6 (8.6 g, yield 41%).

[0177] [Preparation Example 6] Synthesis of Compounds Inv 7 and Inv 8

[0178]

[0179] The same process as in Preparation Example 2 was carried out except that 3-bromodibenzo[b,d]furan was used instead of 2-bromodibenzo[b,d]furan in <Step 1> to obtain Compound Inv 7 (8.8 g, yield 43%) and Compound Inv 8 (8.9 g, yield 43%).

[0180] [Synthesis Example 1] Synthesis of Cpd 10

[0181]

[0182] <Step 1> 2-(7,7-dimethyl-7H-fluoren[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3, Synthesis of 2-Dioxaborane

[0183] After Inv 1 (100 g, 0.313 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (95.6 g, 0.376 mol), Pd(OAc)2 (7 g, 0.031 mol), X-Phos (14.9 g, 0.031 mol) and KOAc (61.4 g, 0.626 mol) were added to the flask, 1,4-dioxaborolane was added. After dissolving in alkane (2L), heating and stirring were performed for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain compound 2-(7,7-dimethyl-7H-fluoren[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (91.1 g, yield 71%).

[0184] <Step 2> Synthesis of Cpd 10

[0185] 2-(7,7-dimethyl-7H-fluoren[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.2 g, 20 mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (8.2 g, 24 mmol), Pd(OAc)2 (0.45 g, 2 mmol), X-Phos (0.95 g, 2 mmol) and Cs2CO3 (13.0 g, 40 mmol) obtained in the above <Step 1> were added to a flask, and 1,4-dioxaborolane was added thereto. After dissolving in 2 L of oxane, the mixture was heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 10 (9.3 g, yield 79%). HRMS [M] + :591.231

[0186] [Synthesis Example 2] Synthesis of Cpd 15

[0187]

[0188] The same process as in Synthesis Example 1 was carried out, except that 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 15 (8.7 g, yield 74%). HRMS [M] + :591.231

[0189] [Synthesis Example 3] Synthesis of Cpd 16

[0190]

[0191] The same process as in Synthesis Example 1 was carried out, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 16 (9.5 g, yield 71%). HRMS [M] + :667.262

[0192] [Synthesis Example 4] Synthesis of Cpd 18

[0193]

[0194] The same process as in Synthesis Example 1 was carried out, except that 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 18 (10.3 g, yield 76%). HRMS [M] + :681.242

[0195] [Synthesis Example 5] Synthesis of Cpd 28

[0196]

[0197] The same process as in Synthesis Example 1 was carried out, except that 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 28 (9.7 g, yield 73%). HRMS [M] + :667.262

[0198] [Synthesis Example 6] Synthesis of Cpd 29

[0199]

[0200] The same process as in Synthesis Example 1 was carried out, except that 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 29 (10.1 g, yield 76%). HRMS [M] + :667.262

[0201] [Synthesis Example 7] Synthesis of Cpd 30

[0202]

[0203] The same process as in Synthesis Example 1 was carried out, except that 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used in place of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine in <Step 2> to obtain compound Cpd 30 (9.5 g, yield 71%). HRMS [M] + :667.262

[0204] [Synthesis Example 8] Synthesis of Cpd 40

[0205] The same process as in Synthesis Example 1 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 40 (9.1 g, yield 77%). HRMS [M] + :591.231

[0206] [Synthesis Example 9] Synthesis of Cpd 45

[0207] The same process as in Synthesis Example 2 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 45 (8.6 g, yield 73%). HRMS [M] + :591.231

[0208] [Synthesis Example 10] Synthesis of Cpd 46

[0209] The same process as in Synthesis Example 3 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 46 (9.5 g, yield 71%). HRMS [M] + :667.262

[0210] [Synthesis Example 11] Synthesis of Cpd 48

[0211] The same process as in Synthesis Example 4 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 48 (9.8 g, yield 72%). HRMS [M] + :681.242

[0212] [Synthesis Example 12] Synthesis of Cpd 58

[0213] The same process as in Synthesis Example 5 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 58 (10.0 g, yield 75%). HRMS [M] + :667.262

[0214] [Synthesis Example 13] Synthesis of Cpd 59

[0215] The same process as in Synthesis Example 6 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 59 (9.7 g, yield 73%). HRMS [M] + :667.262

[0216] [Synthesis Example 14] Synthesis of Cpd 60

[0217] The same process as in Synthesis Example 7 was carried out except that Inv 3 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 60 (10.1 g, yield 76%). HRMS [M] + :667.262

[0218] [Synthesis Example 15] Synthesis of Cpd 130

[0219] The same process as in Synthesis Example 1 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 130 (8.3 g, yield 70%). HRMS [M] + :591.231

[0220] [Synthesis Example 16] Synthesis of Cpd 135

[0221] The same process as in Synthesis Example 2 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 135 (9.0 g, yield 76%). HRMS [M] + :591.231

[0222] [Synthesis Example 17] Synthesis of Cpd 136

[0223] The same process as in Synthesis Example 3 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 136 (10.3 g, yield 77%). HRMS [M] + :667.262

[0224] [Synthesis Example 18] Synthesis of Cpd 138

[0225] The same process as in Synthesis Example 4 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 138 (10.2 g, yield 75%). HRMS [M] + :681.242

[0226] [Synthesis Example 19] Synthesis of Cpd 148

[0227] The same process as in Synthesis Example 5 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 148 (9.6 g, yield 72%). HRMS [M] + :667.262

[0228] [Synthesis Example 20] Synthesis of Cpd 149

[0229] The same process as in Synthesis Example 6 was carried out, except that Inv 6 was used instead of Inv 1 in <Step 1>. Compound Cpd149 (9.7 g, yield 73%) HRMS[M]+:667.262

[0230] [Synthesis Example 21] Synthesis of Cpd 150

[0231] The same process as in Synthesis Example 7 was carried out except that Inv 6 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 150 (9.6 g, yield 72%). HRMS [M] + :667.262

[0232] [Synthesis Example 22] Synthesis of Cpd 160

[0233] The same process as in Synthesis Example 1 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 160 (9.1 g, yield 77%). HRMS [M] + :591.231

[0234] [Synthesis Example 23] Synthesis of Cpd 165

[0235] The same process as in Synthesis Example 2 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 165 (8.6 g, yield 73%). HRMS [M] + :591.231

[0236] [Synthesis Example 24] Synthesis of Cpd 166

[0237] The same process as in Synthesis Example 3 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 166 (9.5 g, yield 71%). HRMS [M] + :667.262

[0238] [Synthesis Example 25] Synthesis of Cpd 168

[0239] The same process as in Synthesis Example 4 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 168 (9.8 g, yield 72%). HRMS [M] +: 681.242

[0240] [Synthesis Example 26] Synthesis of Cpd 178

[0241] The same process as in Synthesis Example 5 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 178 (10.0 g, yield 75%). HRMS [M] + :667.262

[0242] [Synthesis Example 27] Synthesis of Cpd 179

[0243] The same process as in Synthesis Example 6 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 179 (9.7 g, yield 73%). HRMS [M] + :667.262

[0244] [Synthesis Example 28] Synthesis of Cpd 180

[0245] The same process as in Synthesis Example 7 was carried out except that Inv 8 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 180 (10.1 g, yield 76%). HRMS [M] + :667.262

[0246] [Synthesis Example 29] Synthesis of Cpd 190

[0247] The same process as in Synthesis Example 1 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 190 (8.8 g, yield 74%). HRMS [M] + :591.231

[0248] [Synthesis Example 30] Synthesis of Cpd 195

[0249] The same process as in Synthesis Example 2 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 195 (9.2 g, yield 78%). HRMS [M] + :591.231

[0250] [Synthesis Example 31] Synthesis of Cpd 196

[0251] The same process as in Synthesis Example 3 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 196 (10.0 g, yield 75%). HRMS [M] + :667.262

[0252] [Synthesis Example 32] Synthesis of Cpd 198

[0253] The same process as in Synthesis Example 4 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 198 (10.4 g, yield 76%). HRMS [M] + :681.242

[0254] [Synthesis Example 33] Synthesis of Cpd 208

[0255] The same process as in Synthesis Example 5 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 208 (10.2 g, yield 76%). HRMS [M] + :667.262

[0256] [Synthesis Example 34] Synthesis of Cpd 209

[0257] The same process as in Synthesis Example 6 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 209 (9.5 g, yield 71%). HRMS [M] + :667.262

[0258] [Synthesis Example 35] Synthesis of Cpd 210

[0259] The same process as in Synthesis Example 7 was carried out except that Inv 2 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 210 (9.9 g, yield 74%). HRMS [M] + :667.262

[0260] [Synthesis Example 36] Synthesis of Cpd 220

[0261] The same process as in Synthesis Example 1 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 220 (9.2 g, yield 78%). HRMS [M] + :591.231

[0262] [Synthesis Example 37] Synthesis of Cpd 225

[0263] The same process as in Synthesis Example 2 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 225 (9.3 g, yield 79%). HRMS [M] + :591.231

[0264] [Synthesis Example 38] Synthesis of Cpd 226

[0265] The same process as in Synthesis Example 3 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 226 (9.8 g, yield 73%). HRMS [M] + :667.262

[0266] [Synthesis Example 39] Synthesis of Cpd 228

[0267] The same process as in Synthesis Example 4 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 228 (10.4 g, yield 76%). HRMS [M] + :681.242

[0268] [Synthesis Example 40] Synthesis of Cpd 238

[0269] The same process as in Synthesis Example 5 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 238 (10.3 g, yield 77%). HRMS [M] + :667.262

[0270] [Synthesis Example 41] Synthesis of Cpd 239

[0271] The same process as in Synthesis Example 6 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 239 (9.9 g, yield 74%). HRMS [M] + :667.262

[0272] [Synthesis Example 42] Synthesis of Cpd 240

[0273] The same process as in Synthesis Example 7 was carried out except that Inv 4 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 240 (10.4 g, yield 78%). HRMS [M] + :667.262

[0274] [Synthesis Example 43] Synthesis of Cpd 310

[0275] The same process as in Synthesis Example 1 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 310 (8.5 g, yield 72%). HRMS [M] + :591.231

[0276] [Synthesis Example 44] Synthesis of Cpd 315

[0277] The same process as in Synthesis Example 2 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 315 (8.9 g, yield 75%). HRMS [M] + :591.231

[0278] [Synthesis Example 45] Synthesis of Cpd 316

[0279] The same process as in Synthesis Example 3 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 316 (10.2 g, yield 76%). HRMS [M] + :667.262

[0280] [Synthesis Example 46] Synthesis of Cpd 318

[0281] The same process as in Synthesis Example 4 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 318 (10.4 g, yield 76%). HRMS [M] + :681.242

[0282] [Synthesis Example 47] Synthesis of Cpd 328

[0283] The same process as in Synthesis Example 5 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 328 (10.3 g, yield 77%). HRMS [M] + :667.262

[0284] [Synthesis Example 48] Synthesis of Cpd 329

[0285] The same process as in Synthesis Example 6 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 329 (9.9 g, yield 74%). HRMS [M] + :667.262

[0286] [Synthesis Example 49] Synthesis of Cpd 330

[0287] The same process as in Synthesis Example 7 was carried out except that Inv 5 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 330 (10.0 g, yield 75%). HRMS [M] + :667.262

[0288] [Synthesis Example 50] Synthesis of Cpd 340

[0289] The same process as in Synthesis Example 1 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 340 (9.3 g, yield 79%). HRMS [M] + :591.231

[0290] [Synthesis Example 51] Synthesis of Cpd 345

[0291] The same process as in Synthesis Example 2 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 345 (9.0 g, yield 76%). HRMS [M] + :591.231

[0292] [Synthesis Example 52] Synthesis of Cpd 346

[0293] The same process as in Synthesis Example 3 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 436 (10.4 g, yield 78%). HRMS [M] + :667.262

[0294] [Synthesis Example 53] Synthesis of Cpd 348

[0295] The same process as in Synthesis Example 4 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 348 (10.2 g, yield 75%). HRMS [M] + :681.242

[0296] [Synthesis Example 54] Synthesis of Cpd 358

[0297] The same process as in Synthesis Example 5 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 358 (9.9 g, yield 74%). HRMS [M] + :667.262

[0298] [Synthesis Example 55] Synthesis of Cpd 359

[0299] The same process as in Synthesis Example 6 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 359 (9.6 g, yield 72%). HRMS [M] + :667.262

[0300] [Synthesis Example 56] Synthesis of Cpd 360

[0301] The same process as in Synthesis Example 7 was carried out except that Inv 7 was used instead of Inv 1 in <Step 1> to obtain compound Cpd 360 (10.0 g, yield 75%). HRMS [M] + :667.262

[0302] [Synthesis Example 57] Synthesis of Cpd 363

[0303]

[0304] 2-(7,7-dimethyl-7H-fluoren[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.2 g, 20 mmol), 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole (11.4 g, 24 mmol) and Pd(PPh3)4 (1.2 g, 1 mmol) obtained in Synthesis Example 1 were added to a flask, and a 2M Na2CO3 saturated aqueous solution (30 ml) and 1,4-dimethyl-1,3,2-dioxaborolane (8.2 g, 20 mmol) were added to the flask. After dissolving in alkane (100 ml), the mixture was heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 363 (11.3, yield 83%). HRMS [M] + :680.258

[0305] [Synthesis Example 58] Synthesis of Cpd 367

[0306] The same process as in Synthesis Example 57 was carried out, except that 9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine-2-yl)-3-bromo-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd 367 (12.8 g, yield 85%). HRMS [M] + :756.289

[0307] [Synthesis Example 59] Synthesis of Cpd 370

[0308] The same process as in Synthesis Example 57 was carried out, except that 3-bromo-9-(4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd 370 (12.3 g, yield 80%). HRMS [M] + :770.268

[0309] [Synthesis Example 60] Synthesis of Cpd 371

[0310] The same process as in Synthesis Example 57 was carried out, except that 3-bromo-9-(4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd 371 (12.6 g, yield 82%). HRMS [M] + :770.268

[0311] [Synthesis Example 61] Synthesis of Cpd 409

[0312] The same process as in Synthesis Example 57 was carried out, but 3-bromo-9-(4-phenylquinazolin-2-yl)-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd409 (9.4 g, yield 72%). HRMS [M] + :653.247

[0313] [Synthesis Example 62] Synthesis of Cpd 411

[0314] The same process as in Synthesis Example 57 was carried out, except that 3-bromo-9-(4-(4-phenylquinazolin-2-yl)phenyl)-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd411 (10.8 g, yield 74%). HRMS [M] + :729.278

[0315] [Synthesis Example 63] Synthesis of Cpd 412

[0316] The same process as in Synthesis Example 57 was carried out, but 3-bromo-9-(3-(4-phenylquinazolin-2-yl)phenyl)-9H-carbazole was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd412 (10.3 g, yield 71%). HRMS [M] + :729.278

[0317] [Synthesis Example 64] Synthesis of Cpd 413

[0318] The same process as in Synthesis Example 61 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd413 (9.8 g, yield 75%). HRMS [M] + :653.247

[0319] [Synthesis Example 65] Synthesis of Cpd 415

[0320] The same process as in Synthesis Example 62 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd415 (10.3 g, yield 71%). HRMS [M] + :729.278

[0321] [Synthesis Example 66] Synthesis of Cpd 416

[0322] The same process as in Synthesis Example 63 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd416 (10.5 g, yield 72%). HRMS [M] + :729.278

[0323] [Synthesis Example 67] Synthesis of Cpd 417

[0324] The same process as in Synthesis Example 57 was carried out, but N-(4-bromophenyl)-N-phenylnaphthalen-1-amine was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd417 (10.0 g, yield 87%). HRMS [M] + :577.241

[0325] [Synthesis Example 68] Synthesis of Cpd 418

[0326] The same process as in Synthesis Example 57 was carried out, but N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd418 (12.1 g, yield 89%). HRMS [M] + :679.288

[0327] [Synthesis Example 69] Synthesis of Cpd 420

[0328] The same process as in Synthesis Example 57 was carried out, but N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 3-bromo-9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole to obtain compound Cpd 420 (12.5 g, yield 87%). HRMS [M] + :719.319

[0329] [Synthesis Example 70] Synthesis of Cpd 419

[0330]

[0331] The compound Inv 1 (6.4 g, 20.0 mmol) synthesized in Preparation Example 1 and di([1,1'-biphenyl]-4-yl)amine (7.7 g, 24.0 mmol) were dissolved in 100 ml of toluene, and Pd2(dba)3 (0.9 g, 1.0 mmol) was added under nitrogen. Then, NaOtBu (38.4 g, 40 mmol) was added thereto, and (t-Bu)3P (1.0 ml, 1.0 mmol) was added to the reaction solution, and the mixture was refluxed and stirred for 5 hours.

[0332] After the reaction was confirmed to be complete by TLC, the mixture was cooled to room temperature. After the reaction was complete, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na2SO4, distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 419 (10.7 g, yield 89%). HRMS [M] + :603.256

[0333] [Synthesis Example 71] Synthesis of Cpd 429

[0334] The same process as in Synthesis Example 67 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd429 (10.1 g, yield 88%). HRMS [M] + :577.241

[0335] [Synthesis Example 72] Synthesis of Cpd 430

[0336] The same process as in Synthesis Example 68 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd430 (11.4 g, yield 84%). HRMS [M] + :679.288

[0337] [Synthesis Example 73] Synthesis of Cpd 432

[0338] The same process as in Synthesis Example 69 was carried out, but 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(7,7-dimethyl-7H-fluorenyl[2,3-b]benzofuran-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to obtain compound Cpd432 (11.8 g, yield 82%). HRMS [M] + :719.319

[0339] [Synthesis Example 74] Synthesis of Cpd 431

[0340] The same process as in Synthesis Example 70 was carried out except that Inv 3 was used instead of Inv 1 to obtain compound Cpd431 (10.4 g, yield 86%). HRMS [M] + :603.256

[0341] [Example 1] Production of green organic electroluminescent element

[0342] The compound Cpd 417 synthesized in Synthesis Example 1 was purified by sublimation to a high purity according to a generally known method, and then a green organic electroluminescent device was produced as follows.

[0343] Will be The glass substrate coated with a 1000mm thick film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After the distilled water washing, it was ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic405, HwashinTech), and the substrate was cleaned with UV for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

[0344] On the ITO transparent electrode prepared in this way, m-MTDATA (60nm) / TCTA (80nm) / compound Cpd417 (40nm) / CBP+10% Ir(ppy)3 (30nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm) are stacked in sequence to manufacture an organic electroluminescent element.

[0345] The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP used here are as follows.

[0346]

[0347] [Examples 2 to 8] Production of green organic electroluminescent elements

[0348] Organic EL devices were produced in the same manner as in Example 1 except that the compounds listed in the following Table 1 were used instead of the compound Cpd 417 used in Example 1.

[0349] [Comparative Example 1] Production of Green Organic Electroluminescent Element

[0350] A green organic electroluminescent device was produced in the same manner as in Example 1 except that the compound Cpd 417 used in Example 1 was not used.

[0351] [Evaluation Example 1]

[0352] The current density of the green organic electroluminescent devices prepared in Examples 1 to 8 and Comparative Example 1 was measured at 10 mA / cm 2 The driving voltage, current efficiency and luminescence peak at the time of RT-PCR are shown in the following Table 1.

[0353] [Table 1]

[0354] Light-emitting auxiliary layer materials Driving voltage(V) Luminescence peak (nm) Current efficiency (cd / A) Example 1 Cpd 417 6.80 520 42.0 Example 2 Cpd 418 6.75 519 41.9 Example 3 Cpd 419 6.70 517 41.5 Example 4 Cpd 420 6.73 518 41.8 Example 5 Cpd 429 6.80 520 41.5 Example 6 Cpd 430 6.71 519 41.5 Example 7 Cpd 431 6.85 517 41.8 Example 8 Cpd 432 6.80 520 41.8 Comparative Example 1 - 6.93 516 38.2

[0355] As shown in Table 1 above, it can be seen that the green organic electroluminescent elements of Examples 1 to 8 using the compounds of the present invention as light-emitting auxiliary layer materials have a slightly lower driving voltage than the green organic electroluminescent element of Comparative Example 1 using only CBP as a light-emitting layer material without a light-emitting auxiliary layer, and have a better current efficiency than the green organic electroluminescent element of Comparative Example 1.

[0356] [Example 9] Production of red organic electroluminescent element

[0357] The compound Cpd 417 synthesized in Synthesis Example 1 was purified by sublimation to a high purity according to a generally known method, and then a red organic electroluminescent device was produced as follows.

[0358] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After the distilled water washing, it was ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech), and the substrate was cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

[0359] On the ITO transparent electrode prepared in this way, m-MTDATA (60nm) / TCTA (80nm) / compound Cpd417 (40nm) / CBP+10% (piq)2Ir(acac) (30nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm) are stacked in sequence to manufacture an organic electroluminescent element.

[0360] The structures of m-MTDATA, TCTA, CBP and BCP used here are the same as those described in Example 1, and (piq)2Ir(acac) is as follows.

[0361]

[0362] [Examples 10 to 16] Production of red organic electroluminescent elements

[0363] A red organic EL device was produced in the same manner as in Example 32 except that the compounds listed in the following Table 2 were used instead of the compound Cpd 417 used in Example 9.

[0364] [Comparative Example 2] Preparation of red organic electroluminescent element

[0365] A red organic electroluminescent device was produced in the same manner as in Example 32 except that the compound Cpd 417 used in Example 9 was not used.

[0366] [Evaluation Example 2]

[0367] For each of the red organic electroluminescent devices prepared in Examples 9 to 16 and Comparative Example 2, the current density was measured at 10 mA / cm 2 The driving voltage and current efficiency at the time of , are shown in the following Table 2.

[0368] [Table 2]

[0369] Light-emitting auxiliary layer materials Driving voltage(V) Current efficiency (cd / A) Example 9 Cpd 417 5.15 11.2 Example 10 Cpd 418 5.10 11.0 Embodiment 11 Cpd 419 5.15 11.3 Example 12 Cpd 420 5.10 11.0 Embodiment 13 Cpd 429 5.14 11.3 Embodiment 14 Cpd 430 5.15 10.8 Embodiment 15 Cpd 431 5.10 11.3 Example 16 Cpd 432 5.15 11.0 Comparative Example 2 - 5.25 8.2

[0370] As shown in Table 2 above, it can be seen that the red organic electroluminescent elements of Examples 9 to 16 using the compounds of the present invention as the luminescent auxiliary layer material have not only a slightly lower driving voltage but also better current efficiency than the red organic electroluminescent element of Comparative Example 2 using only CBP as the luminescent layer material without the luminescent auxiliary layer.

[0371] [Example 17] Preparation of green organic EL element

[0372] The compound Cpd10 synthesized in Synthesis Example 17 was purified by sublimation to a high purity according to a commonly known method, and then a green organic electroluminescent device was prepared according to the following process.

[0373] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After the distilled water washing, it was ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech), and the substrate was cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

[0374] On the ITO transparent electrode prepared in this way, m-MTDATA (60nm) / TCTA (80nm) / compound Cpd10+10% Ir(ppy)3 (30nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm) are stacked in sequence to produce an organic electroluminescent element.

[0375] [Examples 18 to 75] Production of green organic electroluminescent elements

[0376] Green organic EL devices were produced in the same manner as in Example 17 except that the compounds described in the following Table 3 were used instead of the compound Cpd10 used in Example 17.

[0377] [Comparative Example 3] Preparation of Green Organic EL Element

[0378] A green organic EL device was prepared in the same manner as in Example 17 except that CBP was used instead of the compound Cdp10 used as a light-emitting host substance when forming the light-emitting layer in Example 17.

[0379] [Evaluation Example 3]

[0380] The current density of each green organic EL element prepared in Examples 17 to 75 and Comparative Example 3 was measured at 10 mA / cm 2 The driving voltage, current efficiency and luminescence peak at 500 ℃ are shown in Table 3 below.

[0381] [Table 3]

[0382]

[0383]

[0384] As shown in Table 3 above, it can be seen that when the compounds of the present invention are used as light-emitting layer materials in Examples 17 to 75, the green organic electroluminescent elements show more excellent performance in current efficiency and driving voltage compared with the green organic EL element of Comparative Example 3 using CBP in the past.

[0385] [Example 76] Production of red organic EL element

[0386] The compound Cpd 409 synthesized in Synthesis Example 76 was purified by sublimation to a high purity according to a commonly known method, and then a red organic electroluminescent element was prepared according to the following process.

[0387] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After the distilled water washing, it was ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech), and the substrate was cleaned with UV for 5 minutes, and then transferred to a vacuum evaporator.

[0388] On the ITO transparent electrode prepared in this way, m-MTDATA (60nm) / TCTA (80nm) / compound Cpd409+10% (piq)2Ir(acac) (30nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm) are stacked in sequence to produce an organic electroluminescent element.

[0389] [Comparative Example 4]

[0390] A red organic electroluminescent element was prepared by the same procedure as in Example 76, except that CBP was used instead of the compound Cdp 409 used as the light-emitting host substance when forming the light-emitting layer.

[0391] [Examples 77 to 81] Production of red organic electroluminescent elements

[0392] A green organic EL device was produced in the same manner as in Example 76 except that the compounds listed in the following Table 4 were used instead of the compound Cpd 409 used in Example 76.

[0393] [Evaluation Example 4]

[0394] For each organic electroluminescent element prepared in Examples 76 to 81 and Comparative Example 4, the current density of 10 mA / cm 2 The driving voltage and current efficiency at the time of , are shown in the following Table 4.

[0395] [Table 4]

[0396] sample main body Driving voltage(V) Current efficiency (cd / A) Embodiment 76 Cpd 409 4.77 11.5 Embodiment 77 Cpd 411 4.72 10.2 Embodiment 78 Cpd 412 4.80 11.0 Embodiment 79 Cpd 413 4.59 12.8 Embodiment 80 Cpd 415 4.80 10.4 Embodiment 81 Cpd 416 4.54 12.1 Comparative Example 4 CBP 5.25 8.2

[0397] As shown in Table 4 above, it can be seen that when the compound of the present invention is used as a material for the light-emitting layer of a red organic electroluminescent element (Examples 76-81), it shows excellent performance in terms of efficiency and driving voltage compared to the red organic electroluminescent element in which CBP is used as a material for the light-emitting layer (Comparative Example 4).

[0398] [Example 82] Production of blue organic EL element

[0399] The compound Cpd10 synthesized in Synthesis Example 17 was purified by sublimation to a high purity according to a generally known method, and then a blue organic electroluminescent device was produced as follows.

[0400] Will be The glass substrate coated with a 1000mm thick film of indium tin oxide (ITO) was washed with distilled water ultrasonically. After the distilled water washing, it was ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic405, HwashinTech), and the substrate was cleaned with UV for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

[0401] On the thus prepared ITO transparent electrode, DS-205 (80 nm) / NPB (15 nm) / AND+5% DS-405 (30 nm) / compound Cpd10 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent element.

[0402] [Examples 83 to 137] - Manufacture of blue organic EL elements

[0403] In Example 82, a blue organic EL element was produced in the same manner as in Example 82, except that the compounds listed in Table 5 were used instead of the compound Cpd10 used as the electron transport auxiliary substance.

[0404] [Comparative Example 5] - Manufacture of a blue organic electroluminescent element

[0405] In Example 82, a blue organic electroluminescent element was produced in the same manner as in Example 82 except that the compound Cpd10 used as the electron transport auxiliary layer material was not used and Alq3 as the electron transport layer material was deposited at 30 nm instead of 25 nm.

[0406] [Comparative Example 6] - Manufacture of a blue organic electroluminescent element

[0407] In Example 83, an organic electroluminescent element was produced in the same manner as in Example 83 except that BCP was used instead of the compound Cpd10 used as the electron transport assisting layer material.

[0408] [Evaluation Example 5]

[0409] The current density of 10 mA / cm was measured for the organic electroluminescent devices manufactured in Examples 82 to 137 and Comparative Examples 5 and 6. 2 The driving voltage, current efficiency, luminescent wavelength and lifespan (T97) at the time of irradiation are shown in the following Table 5.

[0410] [Table 5]

[0411]

[0412]

[0413] As can be seen from Table 5, in the case of the blue organic EL elements of Examples 82 to 137 using the compounds of the present invention as electron transport auxiliary layer materials, the driving voltage is similar to or slightly better than that of the blue organic EL element of Comparative Example 5 which does not use an electron transport auxiliary layer, but the current efficiency and life are greatly improved.

[0414] Furthermore, compared with the blue organic EL element of Comparative Example 6 in which CBP is used as a hole blocking layer material instead of an electron transport assisting layer, the driving voltage and current efficiency are excellent and the life span is significantly improved.

Claims

1. A compound represented by the following compound:

2. An organic electroluminescent element, characterized in that: comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers between the anode and the cathode, At least one of the one or more organic layers comprises the compound according to claim 1. 3 . The organic electroluminescent element according to claim 2 , wherein the organic layer is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer. The organic electroluminescent element according to claim 2 , wherein the organic layer is a light-emitting layer or a hole transport layer.

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