Organic light-emitting device

Abstract

The organic light-emitting device provided by the present invention can achieve high luminous efficiency and color purity, and can be used as a backlight source for organic EL displays, liquid crystal displays, lighting, light sources for instruments, display panels, marker lights, etc. [Solution] The present invention provides an aromatic amine compound and an organic light-emitting device, the organic light-emitting device comprising a substrate, a first electrode, an emitting layer comprising one or more organic layer films, and a second electrode, the light-emitting device further comprising a capping layer, the capping layer being on the second electrode, the capping layer comprising a first capping layer and a second capping layer, the capping layer comprising the aromatic amine compound.

Description

[Technical field]

[0001] The present invention relates to an organic light-emitting device, in particular an organic light-emitting device in which an aromatic amine compound containing a trifluoromethyl group is used to significantly improve light extraction efficiency, and the present invention further relates to a light-emitting device material used in the organic light-emitting device. [Background technology]

[0002] Organic light-emitting devices are self-luminous display devices, and have features such as being lightweight and thin, having a wide viewing angle, low power consumption, and high contrast.

[0003] The principle of light emission of organic light-emitting devices is that holes and electrons injected from an electrode recombine in the light-emitting layer, passing through an excited state, and then returning to the ground state, generating light. These light-emitting devices have the characteristics of being thin, capable of emitting high-luminance light at a low driving voltage, and capable of emitting multicolor light by selecting the light-emitting material, and for these reasons, they have attracted much attention.

[0004] Regarding this research, since Kodak's CW Tang et al. published an organic thin-film element capable of emitting light with high brightness, a lot of research has already been done on its applications. Organic thin-film light-emitting elements are used in the main displays of mobile phones, and their practical application is steadily progressing. However, there are still many technical challenges, and the biggest challenges are increasing the efficiency of the elements and reducing their power consumption.

[0005] According to the direction in which the light generated from the organic light emitting layer is emitted, the organic light emitting device can be divided into a bottom emission organic light emitting device and a top emission organic light emitting device. In the bottom emission organic light emitting device, the light is emitted toward the substrate, and a reflective electrode is formed on the upper part of the organic light emitting layer, and a transparent electrode is formed on the lower part of the organic light emitting layer. In this case, if the organic light emitting device is an active matrix device, the part where the thin film transistor is formed does not transmit light, so the light emitting area is small. On the other hand, in the top emission organic device, the transparent electrode is formed on the upper part of the organic light emitting layer, and the reflective electrode is formed on the lower part of the organic light emitting layer, so that the light is emitted in the opposite direction to the substrate, and thus the area through which the light transmits is increased, and the brightness is improved.

[0006] In order to increase the luminous efficiency of top-emission organic light-emitting devices, a method has been adopted in which an organic capping layer is formed on the upper semitransparent metal electrode, which transmits the light from the luminescent layer, to adjust the optical interference distance and suppress quenching caused by external light reflection and energy transfer of surface plasma.

[0007] However, it is very difficult to improve the refractive index of the organic compound used in the capping layer, so on the premise of not increasing the amount of material too much, a double capping layer structure has been proposed to further improve the luminous efficiency of organic light-emitting devices, and some research results have been obtained. In this technology, a low refractive index material is inserted between the high refractive index material and the light-emitting layer to form a second resonant cavity. This is the simplest change in the structure of the organic light-emitting device to further increase the luminous efficiency.

[0008] In conventional technologies, aromatic compounds that do not contain trifluoromethyl groups are used as low refractive index layer materials, but their refractive index is always too high, making it difficult for the difference in refractive index with ordinary high refractive index materials to reach 0.3 or more.

[0009] In conventional technology, long-chain alkanes and inorganic fluorides have typically been selected as low refractive index layer materials. However, long-chain alkanes are easily decomposed at high temperatures, making it difficult to use a vapor deposition method for them, and inorganic fluorides have the problem of requiring high vapor deposition temperatures. In the prior art, proposals have been made to use carbazole derivatives, benzimidazole derivatives, triazole derivatives, etc. as low refractive index layer materials, but the above compounds have high attenuation coefficients, resulting in a refractive index of 1.7 or more, and the attenuation coefficient and absorption coefficient have the relationship shown in the following formula (A): (where α is the absorption coefficient, k is the attenuation coefficient, ω is the light frequency, and c is the speed of light).

number

[0010] As shown in formula (A), the extinction coefficient and the absorption coefficient are proportional, so a material with a high absorption coefficient also has a high extinction coefficient. Therefore, none of the above are suitable for low refractive index materials.

[0011] In addition, some prior arts have proposed using boron complex compounds as low refractive index layer materials, but the decomposition temperature of boron complex compounds is low, making it difficult to control the temperature during the deposition process, and some boron complex compounds are direct sublimation compounds, so they are prone to clogging when using general deposition methods, requiring special deposition means to avoid the problem, which increases the difficulty of the deposition process. Therefore, the above boron complex compounds have many inconveniences when used as low refractive index materials.

[0012] As described above, in conventional techniques, long-chain alkanes with specific structures, inorganic fluorides, carbazole derivatives, benzimidazole derivatives, triazole derivatives, boron complex compounds, and the like have been used as low refractive index materials. However, these materials have significant defects in vapor deposition properties such as heat resistance and clogging, and are therefore not suitable for use. Summary of the Invention [Problem to be solved by the invention]

[0013] In order to solve both the problems of luminous efficiency and color purity, the present inventors have conducted in-depth research based on the above results and found that aromatic amine compounds containing trifluoromethyl groups are suitable for low refractive index materials.In addition, aromatic amine compounds containing trifluoromethyl groups have good transparency when used in the second capping layer, so that they can improve luminous efficiency and obtain high color purity devices. [Means for solving the problem]

[0014] Thus, the present invention provides an aromatic amine compound having the structure shown in general formula 1 below. [ka] [General formula 1] Among them, Ar1, Ar2, and Ar3 each represent a group composed of a substituted or unsubstituted aryl group and / or a heteroaryl group. At least one of Ar1, Ar2, and Ar3 is bonded to at least one trifluoromethyl group. The substituents of Ar1, Ar2, and Ar3 are one or more selected from hydrogen, deuterium, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable heterocyclic group, a substitutable alkenyl group, a substitutable cycloalkenyl group, a substitutable alkynyl group, a substitutable alkoxyl group, a substitutable alkylthio group, a substitutable aryl ether group, a substitutable aryl thioether group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable carbonyl group, a substitutable carboxyl group, a substitutable oxycarbonyl group, a substitutable carbamoyl group, a substitutable silyl group, a substitutable alkylamino group, and a substitutable arylamino group.

[0015] Since the thermal stability of the compound can be improved by increasing the number of amine structures, it is preferable that at least one of the substituents of Ar1, Ar2, and Ar3 is substituted with an arylamino group.

[0016] Since the diamine structure has excellent combined capabilities of sublimation performance, thermal stability, and chemical stability, an aromatic amine compound as shown in the following general formula 2 is preferably selected. [ka] [General formula 2] In the above, Ar4 and Ar5 each represent a group consisting of a substituted or unsubstituted aryl group and / or a heteroaryl group. The substituents of Ar4 and Ar5 are one or more selected from hydrogen, deuterium, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable heterocyclic group, a substitutable alkenyl group, a substitutable cycloalkenyl group, a substitutable alkynyl group, a substitutable alkoxyl group, a substitutable alkylthio group, a substitutable aryl ether group, a substitutable aryl thioether group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable carbonyl group, a substitutable carboxyl group, a substitutable oxycarbonyl group, a substitutable carbamoyl group, a substitutable silyl group, a substitutable alkylamino group, and a substitutable arylamino group. n1 and n2 each represent an integer of 0 to 5, and n1 and n2 are not 0 at the same time. Adding trifluoromethyl groups to both sides of the diamine structure further improves the overall performance, such as reducing the refractive index, reducing the sublimation temperature, improving process stability and chemical stability, and the like, so the aromatic amine compound represented by the following general formula 3 is preferably selected. [ka] [General formula 3]

[0017] n3 and n4 are integers from 0 to 5, and n1, n2, n3, and n4 cannot all be 0 at the same time. By adding a trifluoromethyl group to each benzene ring in the middle of the diamine, the refractive index is reduced, the difficulty of the synthesis process is reduced, and the chemical stability is improved, so that the overall performance is further improved. Therefore, the aromatic amine compound shown in the following general formula 4 is preferably selected. [ka] [General formula 4]

[0018] n5 is an integer from 0 to 5, and n1, n2, n3, n4, and n5 cannot all be 0 at the same time. When the intermediate benzene ring of the diamine is biphenyl, the deposition stability and optical performance reach an optimum balance, and therefore, the aromatic amine compound represented by the following general formula 5 is preferably selected. [ka] [General formula 5]

[0019] n6 and n7 are integers from 0 to 5, and n1, n2, n3, n4, n6, and n7 cannot be 0 at the same time.

[0020] Since fused rings and spiro rings increase the refractive index and are not suitable for low refractive index materials, the Ar2 in the general formula 5 is preferably selected from aryl or heteroaryl groups that are not fused rings or spiro rings, where the fused ring refers to a substituted or unsubstituted fused ring, and the spiro ring refers to a substituted or unsubstituted spiro ring.

[0021] The more trifluoromethyl groups there are at both ends of the molecule, the lower the refractive index, and the optimal optical effect is obtained when the total number of the four trifluoromethyl groups at both ends is greater than 4. Therefore, n1+n2+n3+n4>4 in the general formula 5 is desirable.

[0022] Since the introduction of a heteroaryl group improves the light extraction efficiency, in the above general formula 2, Ar1 and Ar4 are preferably heteroaryl groups directly linked to nitrogen.

[0023] Since fused rings and spiro rings increase the refractive index and are not suitable for low refractive index materials, the Ar2 in the general formula 2 is preferably selected from aryl or heteroaryl groups that are not fused rings or spiro rings, where the fused ring refers to a substituted or unsubstituted fused ring, and the spiro ring refers to a substituted or unsubstituted spiro ring.

[0024] The more trifluoromethyl groups there are at both ends of the molecule, the lower the refractive index, and the optimal optical effect is obtained when the total number of the two trifluoromethyl groups at both ends is greater than 2. Therefore, n1+n2>2 in the general formula 2 is desirable.

[0025] The alkyl group is preferably a C1 to C20 alkyl group, and more preferably one or more of saturated aliphatic hydrocarbon groups such as a trifluoromethyl group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a s-butyl group, or a t-butyl group. The alkyl group may or may not have a substituent.

[0026] The cycloalkyl is preferably a C3 to C20 cycloalkyl group, and more preferably one or more of saturated alicyclic alkyl groups such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, or an adamantyl group. The cycloalkyl group may or may not have a substituent.

[0027] The heterocyclic group is preferably a C2 to C20 heterocyclic group, and more preferably one or more of aliphatic rings having atoms other than carbon in the ring, such as a pyran ring, a piperidine ring, or a cyclic amide. The heterocyclic group may or may not have a substituent.

[0028] The alkenyl group is preferably a C2 to C20 alkenyl group, and more preferably one or more of unsaturated aliphatic hydrocarbon groups containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group. The alkenyl group may or may not have a substituent.

[0029] The cycloalkenyl group is preferably a C3 to C20 cycloalkenyl group, and more preferably one or more of unsaturated alicyclic alkyl groups containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group. The cycloalkenyl group may or may not have a substituent.

[0030] The alkynyl group is preferably a C2 to C20 alkynyl group, and more preferably an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group. The alkynyl group may or may not have a substituent.

[0031] The alkoxyl group is preferably a C1 to C20 alkoxyl group, and more preferably one or more of functional groups of an aliphatic hydrocarbon group to which a methoxy group, an ethoxy group, a propoxy group, or the like is bonded via an ether bond. The aliphatic hydrocarbon group may or may not have a substituent.

[0032] The alkylthio group is a group in which the oxygen atom of an alkoxyl group is replaced with a sulfur atom. It is preferably a C1 to C20 alkylthio group, and the alkyl group of the alkylthio group may or may not have a substituent.

[0033] The aryl ether group is preferably a C6 to C40 aryl ether group, and more preferably an aromatic functional group to which a phenoxy group or the like is bonded via an ether bond. The aryl ether group may or may not have a substituent.

[0034] The aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is replaced with a sulfur atom. The aryl thioether group is preferably a C6 to C60 aryl thioether group. The aromatic functional group in the aryl thioether group may or may not have a substituent.

[0035] The aryl group is preferably a C6 to C60 aryl group, and more preferably one or more of aromatic functional groups such as a perfluorophenyl group, a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may or may not have a substituent.

[0036] The heteroaryl is preferably a C4 to C60 aromatic heterocyclic group, and more preferably one or more of a furyl group, a thienyl group, a pyrrolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyridyl group, a quinolinyl group, etc. The aromatic heterocyclic group may or may not have a substituent.

[0037] The carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, and alkylamino group may or may not have a substituent. The number of carbon atoms of the substituent of the alkylamino group is not particularly limited, and is usually in the range of 2 to 60.

[0038] The silyl group is represented as a functional group having a bond to a silicon atom, such as a trimethylsilyl group, a triethylsilyl group, a dimethyl t-butylsilyl group, a triphenylsilyl group, etc., and the silyl group may or may not have a substituent. The number of carbon atoms in the silyl group is not particularly limited, and is usually in the range of 1 to 40.

[0039] The arylamine group is preferably a C6-C40 arylamine group, more preferably an aromatic functional group bonded via an amine bond, such as an azobenzene group, an azopyridine group, or a pyridineazobenzene group. The arylamine group may be substituted or unsubstituted. In the substituted situation, each of the substituents is independently selected from one or more of deuterium, halogen, C1-C6 alkyl group, C3-C6 cycloalkyl group, C3-C6 heterocyclic group, C2-C6 alkenyl group, C4-C6 cycloalkenyl group, C2-C6 alkynyl group, C1-C6 alkoxyl group, or C1-C6 alkylthio group.

[0040] The aromatic amine compound having a trifluoromethyl group provided by the present invention has excellent thin film stability and refractive index, and therefore can solve both the problems of improving luminous efficiency and color purity.

[0041] The aromatic amine compound having a trifluoromethyl group is not particularly limited, and specific examples include the following. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0042] The synthesis of the above aromatic amine compounds containing a trifluoromethyl group can be carried out by known methods, such as, but not limited to, the Buchwald-Hartwig reaction using nickel or palladium, or the Ullman reaction using copper.

[0043] The present invention further provides an organic light-emitting device material, which contains the aromatic amine compound described in any one of the above. The organic light-emitting device obtained by the present invention uses the aromatic amine compound described above, and therefore has excellent thin film stability and refractive index, and can solve both the problems of improving luminous efficiency and improving color purity.

[0044] The present invention further provides an organic light-emitting device, comprising a substrate, a first electrode, an emitting layer comprising one or more organic layer films, a second electrode, and one or more capping layers, wherein the organic light-emitting device comprises the organic light-emitting device material described above.

[0045] The present invention further provides an organic light emitting device capping layer material, the organic light emitting device capping layer material comprising an aromatic amine compound according to any one of the above aspects.

[0046] The present invention further provides an organic light-emitting device, comprising a substrate, a first electrode, a light-emitting layer comprising one or more organic layers, and a second electrode, the light-emitting device further comprising a capping layer, the capping layer being on the second electrode, the capping layer comprising a first capping layer and a second capping layer, the capping layer comprising the above organic light-emitting device capping layer material.

[0047] The refractive index of the light-emitting layer of an organic electroluminescence device is usually 1.7. When the material with a refractive index exceeding that of the light-emitting layer by 0.1 or more is used as the first capping layer, the semi-mirror surface between the first capping layer and the air can better form a resonant cavity with the lower reflective anode, so the refractive index of the first capping layer is selected to be 1.8 or more. The refractive index of the second capping layer is 1.5 to 1.7. Since it is necessary to form another resonant cavity on the first capping layer, the refractive index of the first capping layer and the second capping layer needs to have a relatively large difference, and when the difference is 0.3, a semi-mirror surface can be formed, so more preferably, the difference between the refractive index of the first capping layer and the refractive index of the second capping layer is 0.3 or more.

[0048] The first capping layer is formed of at least one of the following inorganic compounds and organic compounds, in which the inorganic compound is one or more of SiOx, SiNy, Zns, ZnSe, ZrO, or TiO2, and the x and y are integers of 1 to 4. The organic compound is one or more of aromatic amine derivatives, carbazole derivatives, benzimidazole derivatives, or triazole derivatives. Since inorganic compounds require higher temperatures during the deposition process than organic compounds, it is preferable that the first capping layer material is an organic compound.

[0049] The second capping layer of the present invention can be located not only between the first electrode and the second electrode, but also between the second electrode and the first capping layer, or it can be located on the second electrode.

[0050] Since the first capping layer is disposed on the second electrode, the second electrode and the organic light emitting layer can be effectively protected and prevented from being affected by external moisture, oxygen, and contaminants, thereby preventing a decrease in the life span of the organic light emitting device. A top emission light emitting device has an advantage of being able to enlarge the light emitting surface compared to a bottom emission light emitting device, and when used in combination with a capping layer, the overall light extraction efficiency can be improved.

[0051] The second capping layer of the present invention can realize high luminous efficiency by including the aromatic amine compound containing a trifluoromethyl group. The aromatic amine compound containing a trifluoromethyl group has a low refractive index because it has a fluorine element. Furthermore, since the film-forming performance of the evaporated thin film is excellent, it is possible to provide a stable refractive index and attenuation coefficient for various bottom layers such as glass and metal. When the bottom layer of a material having low film-forming performance of the evaporated thin film changes, the refractive index and attenuation coefficient often change significantly. In order to maximize high luminous efficiency and have high color purity, the aromatic amine compound containing a trifluoromethyl group is preferably laminated to a thickness of 20 nm to 120 nm. More preferably, the laminate thickness is 40 nm to 80 nm. In addition, from the viewpoint of maximizing luminous efficiency, the laminate thickness is more preferably 50 nm to 70 nm.

[0052] The method for forming the capping layer is not particularly limited, and examples thereof include electric resistance heating deposition, electron beam deposition, sputtering, molecular lamination, coating, inkjet, scraper, and laser transfer methods, and are not particularly limited.

[0053] Hereinafter, embodiments of the organic light-emitting device of the present invention will be specifically described.

[0054] In the light-emitting element of the present invention, the substrate used is preferably a glass substrate such as sodium glass or non-alkali glass. The thickness of the glass substrate is sufficient to maintain mechanical strength, and 0.5 mm or more is sufficient. As for the glass material, the fewer ions eluted from the glass, the better, so non-alkali glass is preferable. In addition, glass with a protective coating such as SiO2, which is commercially available, can also be used. In addition, as long as the first electrode functions stably, the substrate does not necessarily need to be glass, and for example, the anode may be formed on a plastic substrate.

[0055] The material used for the first electrode is preferably a metal having high refractive index properties, such as gold, silver, or aluminum, or a metal alloy, such as an APC-based alloy. These metals or metal alloys may be multi-layered. Transparent conductive metal oxides, such as tin oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO), may also be laminated on the upper and / or lower surfaces of the metal, metal alloy, or the laminate thereof.

[0056] The material used for the second electrode is preferably a material capable of forming a semi-transparent or transparent film capable of transmitting light. For example, silver, magnesium, aluminum, calcium, or alloys of these metals, tin oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or other transparent conductive metal oxides. These metals, alloys, or metal oxides may also be multi-layer stacks.

[0057] The method for forming the electrodes is not particularly limited and may be electrical resistance heating deposition, electron beam deposition, sputtering, ion plating, adhesive coating, etc. In addition, one of the first electrode and the second electrode acts as an anode with respect to the organic film layer, and the other acts as a cathode, based on the work function of the material used.

[0058] The organic layer may be composed of only the light-emitting layer, or may have a structure in which 1) a hole transport layer / light-emitting layer, 2) a light-emitting layer / electron transport layer, 3) a hole transport layer / light-emitting layer / electron transport layer, 4) a hole injection layer / hole transport layer / light-emitting layer / electron transport layer, 5) a hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer, etc. are laminated. Each of the above layers may be either a single layer or a multilayer. When the structures 1) to 5) are adopted, the anode side electrode is joined to the hole import layer or the hole transport layer, and the cathode side electrode is joined to the electron import layer or the electron transport layer.

[0059] The hole transport layer is formed by laminating or mixing one or more types of hole transport materials, or by using a mixture of a hole transport material and a polymer adhesive. The hole transport material must transport holes from the positive electrode with high efficiency between electrodes to which an electric field is applied, so it is desirable that the hole transport material has high hole injection efficiency and can efficiently transport the injected holes. Therefore, it is required that the hole transport material has an appropriate ion potential, a large hole transition rate, excellent stability, and is unlikely to generate impurities that can become traps during production and use. There is no particular limitation on the substance that satisfies such conditions, and examples of such substances include biphenylamines such as 4,4'-di(N-(3-methylphenyl)-N-phenylamino)biphenyl (TPD), 4,4'-di(N-(1-naphthyl)-N-phenylamino)biphenyl (NPD), 4,4'-di(N,N-di(4-biphenyl)amino)biphenyl (TBDB), and di(N,N-diphenyl-4-phenylamino)-N,N-diphenyl-4,4'-diamino-1,1'-biphenyl (TPD232); star-shaped triarylamine materials such as 4,4',4''-tris(3-methylphenyl(phenyl)amino)triphenylamine (m-MTDATA) and 4,4',4''-tris(1-naphthyl(phenyl)amino)triphenylamine (1-TNATA); The material may be a material having an azole skeleton, among which carbazole polymers are preferred, and specifically, dicarbazole derivatives such as di(N-arylcarbazole) or di(N-alkylcarbazole), tricarbazole derivatives, tetracarbazole derivatives, triphenyl compounds, pyrazoline derivatives, stilbene compounds, hydrazine compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, heterocyclic compounds such as porphyrin derivatives, or fullerene derivatives can be listed, and among the polymers, polycarbonates or styrene derivatives further having the above monomers in the side chains, polythiophenes, polyphenylamines, polyfluorenes, polyvinylcarbazoles, and polysilanes are preferred. Inorganic compounds such as P-type Si and P-type SiC can also be used.

[0060] A hole injection layer may be provided between the anode and the hole transport layer. By providing the hole injection layer, a low driving voltage can be realized in the organic light emitting device, and the durability life can be extended. It is preferable that the hole injection layer is generally made of a material having a lower ion potential than the hole transport layer material. Specifically, for example, it may be a benzidine derivative such as the above TPD232, a star-shaped triarylamine material group, or a phthalocyanine derivative. It is also preferable that the hole injection layer is composed solely of an acceptor compound, or the acceptor compound is doped into another hole transport layer. Examples of the acceptor compound include metal chlorides such as iron trichloride (III), aluminum chloride, gallium chloride, indium chloride, and antimony chloride, metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide, and ruthenium oxide, and charge transfer complexes such as ammonium tris(4-bromophenyl)hexachloroantimonate (TBPAH). Alternatively, organic compounds having a nitro group, a cyano group, a halogen or a trifluoromethyl group in the molecule, quinone compounds, acid anhydride compounds, fullerenes, and the like may also be used.

[0061] In the present invention, the light-emitting layer may be any one of a single layer and a multilayer, and may be formed using light-emitting materials (host material, dope material), and may be a mixture of a host material and a dope material, or may be a host material alone, or either. That is, in each light-emitting layer of the light-emitting element of the present invention, only the host material or only the dope material may emit light, or the host material and the dope material may emit light together. Considering the efficient use of electric energy and the obtainment of light emission with high color purity, it is preferable that the light-emitting layer is formed by mixing a host material and a dope material. Also, the host material and the dope material may each be one type, or a combination of multiple materials may be used, or either. The dope material may be added to the whole host material, or may be added to a part of it, or either. The dope material may be laminated or dispersed, or either. The dope material can control the light emission color. If the amount of the dope material is too large, concentration quenching phenomenon occurs, so the amount of the dope material used is preferably 20% by weight or less, more preferably 10% by weight or less, based on the host material. The doping method may be a method of co-evaporating with the host material, or a method of mixing with the host material in advance and then simultaneously vapor-depositing the mixture.

[0062] Specific examples of the luminescent material that can be used include condensed ring derivatives of anthracene, pyrene, and the like, which are conventionally known as luminescent materials, metal chelate quinolinol compounds such as tris(8-quinolinol)aluminum, dibenzofuran derivatives, carbazole derivatives, indolecarbazole derivatives, polyphenylenevinylene derivatives in polymers, polyparaphenylene derivatives, and polythiophene derivatives, but are not particularly limited thereto.

[0063] There are no particular limitations on the host material contained in the light-emitting material, and examples of the host material that can be used include compounds having a condensed aromatic ring, such as anthracene, phenanthrene, pyrene, benzophenanthrene, tetracene, perylene, benzo[9,10]phenanthrene, fluoranthene, fluorene, and indene, or derivatives thereof; aromatic amine derivatives, such as N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine; metal chelate-based hydroxyl quinoline compounds, such as tris(8-quinolinol)aluminum; pyrrolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolecarbazole derivatives, and triazine derivatives; and, among polymers, polyphenylenevinylidene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives, but there are no particular limitations on the host material.

[0064] The doping material is not particularly limited, and examples thereof include compounds having a condensed aromatic ring such as naphthalene, anthracene, phenanthrene, pyrene, benzophenanthrene, perylene, benzo[9,10]phenanthrene, fluoranthene, fluorene, and indene, or derivatives thereof (e.g., 2-(benzothiazol-2-yl)-9,10-diphenylanthracene, etc.), furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, and dibenzothiophene. Examples of the aromatic heterocyclic compound include compounds having a heteroaromatic ring, such as dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and thioxanthene, or derivatives thereof; borane derivatives, distyrylbenzene derivatives, aminostyrene derivatives, pyrrole methine derivatives, diketopyrrolo[3,4C]pyrrole derivatives, coumarin derivatives, zole derivatives, such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and trizole; and aromatic amine derivatives.

[0065] Also, a phosphorescent material can be doped into the light-emitting layer. The phosphorescent material is a material that can emit phosphorescence even at room temperature. When using a phosphorescent material as a dopant, it must be capable of emitting phosphorescence at room temperature, but there is no particular limitation. The phosphorescent material is preferably an organometallic complex compound containing at least one metal selected from indium, ruthenium, rhodium, palladium, platinum, osmium, and rhenium. From the viewpoint of having high phosphorescent efficiency at room temperature, an organometallic complex containing indium or platinum is more preferable. As the host material used in combination with the phosphorescent dopant, indole derivatives, carbazole derivatives, indolecarbazole derivatives, nitrogen-containing aromatic compound derivatives having pyridine, pyrimidine, or triazine skeletons, polyarylphenyl derivatives, spirofluorene derivatives, aromatic hydrocarbon compound derivatives such as truxene and benzo[9,10]phenanthrene, compounds containing oxygen group elements such as dibenzofuran derivatives and dibenzothiophene, and organometallic complexes such as hydroxyl quinoline beryllium complexes are well used, but are not particularly limited as long as they are larger than the triplet state of the dopant used and can smoothly inject or transport electrons and holes from each transport layer. In addition, two or more triplet-state emitting dopants can be included, and two or more host materials can be included. In addition, one or more triplet-state emitting dopants and one or more fluorescent emitting dopants can be included.

[0066] In the present invention, the electron transport layer is a layer in which electrons are injected from the cathode and further transport the electrons. It is desirable that the electron transport layer has a high electron injection efficiency and can efficiently transport the injected electrons. Therefore, it is desirable that the electron transport layer is made of a material that has a large electron affinity and electron transition rate, is excellent in stability, and is unlikely to generate impurities that can become traps during manufacture and use. However, considering the balance of hole and electron transport, if the electron transport layer can mainly efficiently block holes from the anode from flowing to the cathode without recombining with them, even if it is made of a material with a low electron transport ability, the effect of improving the luminous efficiency will be equivalent to that of a material with a high electron transport ability. Therefore, the electron transport layer of the present invention also includes a hole blocking layer that can efficiently block hole transition as an equivalent.

[0067] The electron transport material used in the electron transport layer is not particularly limited, and examples thereof include condensed aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-di(diphenylvinyl)biphenyl, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, hydroxyquinoline complexes such as tris(8-quinolinol)aluminum, benzoquinolinol complexes, hydroxyzole complexes, azomethine complexes, cycloheptatriene ketone metal complexes, and flavonol metal complexes. From the viewpoints of lowering the driving voltage and enabling efficient light emission, it is desirable to use a compound having a heteroaromatic ring structure, and the heteroaromatic ring structure is composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus, and contains electron-withdrawing nitrogen.

[0068] A heteroaromatic ring containing electron-withdrawing nitrogen has high electrophilicity. An electron transport material containing electron-withdrawing nitrogen is easy to receive electrons from a cathode having high electrophilicity, thereby lowering the driving voltage of a light-emitting device. In addition, since the supply of electrons to the light-emitting layer is increased, the probability of recombination in the light-emitting layer is increased, thereby improving the light-emitting efficiency. Examples of heteroaromatic rings containing electron-withdrawing nitrogen include pyridine rings, pyrazine rings, pyrimidine rings, quinoline rings, quinoxaline rings, naphthyridine rings, pyrimidopyrimidine rings, benzoquinoline rings, phenanthroline rings, imidazole rings, oxazole rings, oxadiazole rings, triazole rings, thiazole rings, thiadiazole rings, benzoxazole rings, benzothiazole rings, benzimidazole rings, and phenanthroimidazole rings.

[0069] In addition, examples of compounds having these heteroaromatic ring structures include benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, and oligopyridine derivatives such as bipyridine and tribipyridine. When the derivative has a condensed aromatic ring skeleton, the glass transition temperature increases, the electron transition rate increases, and the effect of lowering the driving voltage of the light-emitting device is enhanced, which is preferable. In addition, in terms of extending the durability of the light-emitting device, facilitating synthesis, and making it easy to purchase raw materials, the condensed aromatic ring skeleton is preferably an anthracene skeleton, a pyrene skeleton, or a phenanthroline skeleton.

[0070] The electron transport material may be used alone, or two or more of the electron transport materials may be mixed together, or one or more other electron transport materials may be mixed with the electron transport material. A donor compound may also be added. Here, the donor compound refers to a compound that improves the electron conductivity of the electron transport layer by improving the electron injection barrier so that electrons can be easily injected from the cathode or the electron injection layer into the electron transport layer. Suitable examples of the donor compound of the present invention include alkali metals, inorganic salts containing alkali metals, complexes of alkali metals and organic substances, alkaline earth metals, inorganic salts containing alkaline earth metals, and complexes of alkaline earth metals and organic substances. Suitable types of alkali metals or alkaline earth metals include alkali metals such as lithium, sodium, or cesium, which have a low work function and are effective in improving the electron transport ability, and alkaline earth metals such as magnesium and calcium.

[0071] In the present invention, an electron injection layer can also be provided between the cathode and the electron transport layer. Usually, the electron injection layer is inserted to help inject electrons from the cathode to the electron transport layer. During insertion, a compound having a heteroaromatic ring structure containing electron-withdrawing nitrogen may be used, or a layer containing the donor compound may be used. In addition, an inorganic insulator or semiconductor may also be used in the electron injection layer. By using these materials, it is possible to effectively prevent short circuits in the light-emitting device and to improve the electron injection property, so that it is preferable. As these insulators, it is desirable to use at least one metal compound selected from alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. In addition, complexes of organic substances and metals can also be used well.

[0072] The method for forming each of the layers constituting the light-emitting element is not particularly limited, and may include electric resistance heating deposition, electron beam deposition, sputtering, molecular lamination method, coating method, etc. However, in general, electric resistance heating deposition or electron beam deposition is preferable in terms of element characteristics.

[0073] The thickness of the organic layer is not limited because it varies depending on the electrical resistance value of the light-emitting substance, but is preferably 1 to 1000 nm. The thickness of each of the light-emitting layer, the electron transport layer, and the hole transport layer is preferably 1 nm to 200 nm, more preferably 5 nm to 100 nm.

[0074] The light-emitting element of the present invention has a function of converting electric energy into light. Here, direct current is mainly used as the electric energy, but pulse current or alternating current may also be used. There is no particular restriction on the current value and voltage value, but considering the power consumption and life of the element, a method that can obtain maximum brightness with as little energy as possible should be selected.

[0075] The light-emitting device of the present invention can be suitably used, for example, as a flat display in a matrix and / or field mode.

[0076] The matrix method refers to a method in which pixels for display are arranged in two dimensions, such as a grid or mosaic, and characters and images are displayed by a collection of pixels. The shape and size of the pixels are determined by the application. For example, when displaying images and characters on computers, monitors, and televisions, square pixels with side lengths of 300 μm or less are usually used, and for large displays such as display panels, pixels with side lengths of mm are used. For monochrome display, it is sufficient to arrange pixels of the same color, but for color display, red, green, and blue pixels are arranged and displayed. In that case, there are typically triangular and striped types. In addition, the driving method of this matrix can be either drive-by-wire or active matrix. Drive-by-wire has a simple structure, but when considering the operating characteristics, active matrix may be superior in some cases, so it is necessary to use it flexibly according to the application.

[0077] The field method in the present invention refers to a method of forming a pattern and illuminating an area determined by the arrangement of the pattern to display predetermined information. Examples include digital clocks, time and temperature displays in thermometers, operation status displays of audio equipment, microwave ovens, and panel displays in automobiles. Moreover, the matrix display and the field display can coexist on the same panel.

[0078] The light-emitting device of the present invention is preferably used as a portable flat display, and can provide a display with lower power consumption and higher luminous efficiency than conventional displays. Effect of the Invention

[0079] The aromatic amine compound containing trifluoromethyl group provided by the present invention has a low refractive index, and can realize high luminous efficiency and high color purity. In addition, the excellent deposition performance of the evaporated thin film allows it to have a stable refractive index and extinction coefficient on various underlayers such as glass and metal. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0080] The present invention will be described by way of examples through the following examples, but the present invention is not limited to the aromatic amine compounds containing a trifluoromethyl group and the synthesis methods thereof shown in these examples. 1-11、 17-19 are currently reference examples and are examples 12 -16 is an embodiment of the present invention.

[0081] Unless otherwise specified, the materials and methods used in the examples and comparative examples are obtained or used by means that are routinely known to those skilled in the art.

[0082] Toluene, xylene, methanol, 3-aminopyridine, etc. were purchased from a Chinese pharmaceutical company, 4,4'-dibromobiphenyl, 3,5-di(trifluoromethyl)phenylboronic acid, etc. were purchased from Zhengzhou Haihua Photoelectric Co., Ltd., and various palladium catalysts, etc. were purchased from Aldrich.

[0083] 1 H-NMR spectra were measured using a JEOL (400 MHz) nuclear magnetic resonance spectrometer, and HPLC spectra were measured using a Shimadzu LC-20AD high-efficiency liquid chromatograph.

[0084] In the examples and comparative examples, the following compounds were synthesized and / or used. Compound

[15] : 4-trifluoromethylphenyl-bis-(4,4'-biphenyl)-amine Compound

[16] : 4-trifluoromethylphenyl-bis-(4-(3-pyridine)phenyl)-amine Compound

[40] : 3,5-di(trifluoromethyl)phenyl-bis-(N-3-pyridyl-phenyl)amino-amine Compound

[49] : 4,4'-bis(N-phenyl-(3,5-di(3,5-di(trifluoromethyl)phenyl)phenyl))amino-biphenyl Compound

[50] : 4,4'-bis(N-(3-pyridyl)-(3,5-di(3,5-di(trifluoromethyl)phenyl)phenyl))amino-biphenyl Compound

[67] : 4,4'-bis(N-(3-pyridyl)-(3,5-di(3,5-di(trifluoromethyl)phenyl)phenyl)amino-bi(2-pyridine) Compound

[70] : 1,4-bis(N-(3-(2-5-benzothiophene))-(3,5-di(3,5-di(trifluoromethyl)phenyl)phenyl)amino-benzene Compound

[71] : 1,4-bis(N-(3-pyridyl)-(5-(3,5-di(trifluoromethyl)phenyl)-3-(4-phenylcarbonylphenyl)phenyl))amino-benzene Compound

[91] : 1,4-bis(N-(3-pyridyl)-(3-(3,5-di(trifluoromethyl)phenyl)-5-(3,5-diadamanphenyl)phenyl))amino-benzene Compound

[93] : 1,4-bis(N-(3-pyridyl)-(3-(3,5-di(trifluoromethyl)phenyl)pyrene))amino-benzene Compound

[94] : 1,4-bis(N-(3-pyridyl)-(3-(3,5-di(trifluoromethyl)phenyl)-9,9'-spirobifluorene))amino-benzene Compound

[99] : 4,4'-bis(N-bis(3,5-di(trifluoromethyl))phenyl)amino-2,2'-bistrifluoromethylbiphenyl Compound

[0102] : Bis(4-bis(N-bis(3,5-di(trifluoromethyl))phenyl)amino-phenyl)-2,4-bistrifluoromethyl-benzene Compound

[0105] : 4,4'-bis(N-(3,5-di(trifluoromethyl)phenyl)-(4-trifluoromethylphenyl))amino-2,2'-bistrifluoromethylbiphenyl Compound

[0113] : 4,4'-bis(N-(3-pyridyl)-(3,5-di(p-trifluoromethylphenyl)phenyl))amino-biphenyl Compound

[0114] : 4,4'-bis(N-(3-pyridyl)-(3-(3,5-ditrifluoromethylphenyl)-5-(p-trifluoromethyl)phenyl))amino-biphenyl

[0085] The following compounds are also used in the examples and comparative examples. BF3.Et2O: Boron trifluoride ethyl ether complex DIEA: N,N-diisopropylethylamine NPD: (N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,4'-diamine) [ka] F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane) [ka] BH: (9-(2-naphthyl)-10-(4-(1-naphthyl)phenyl)anthracene) [ka] BD: (E-7-(4-(diphenylamino)styrene)-N,N-diphenyl-9,9'-dimethylfluorenyl-2-amine) [ka] Alq3: (Tris(8-hydroxyquinolinato)aluminum) [ka] TBDB: (N,N,N',N'-4(4-biphenyl)benzidine) [ka] DZ1: [[[2,2'-[1,2-ethylenedi[(trivalent nitrogen)methine]]bis[4,6-bis(t-butyl)phenol]](2-)]]tetrafluorodiborane [ka] CZX: 4,4'-bis(N-(3-pyridyl)-(3,5-diphenylphenyl))amino-biphenyl [ka] ZJF: 4,4'-bis(N-(4-pyridyl)-phenyl)amino-2,5-bisbiphenylthiophene [ka] LXY: Bis(N-phenylcarbazole)-2,5-diphenylthiophene [ka]

[0086] When the chemical formula and structural formula of a compound described in the present specification are both described in the present specification, the structure of the compound is based on the structural formula. Preparation Example 1 [ka]

[15]

[0087] Under nitrogen atmosphere, 4.66 g (20.2 mmol) of 4-bromobiphenyl, 1.48 g (9.18 mol) of 4-trifluoromethylaniline, 0.104 mg (0.18 mmol) of bis(dibenzylideneacetone)palladium, 0.174 mg (0.36 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 4.14 g (44.08 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 3.2 g of crude product. The crude product was then subjected to a pressure of 3×10 -3 The mixture was sublimated at 220°C under reduced pressure to obtain 2.5 g of compound

[15] (white). 1HNMR(CDCl3):δ7.50-7.30(m,8H),7.23-7.20(m,8H),6.50(d,4H),6.40(d,2H) HPLC (purity=99.1%) Preparation Example 2 [ka]

[16]

[0088] Under nitrogen atmosphere, 4.73 g (20.2 mmol) of 4-(3-pyridine)bromobenzene, 1.48 g (9.18 mmol) of 4-trifluoromethylaniline, 0.104 mg (0.18 mmol) of bis(dibenzylideneacetone)palladium, 0.174 mg (0.36 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 4.14 g (44.08 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 4.5 g of crude product. The crude product was then subjected to a pressure of 3×10 -3 The mixture was sublimated at 220°C under reduced pressure to obtain 3.9 g of compound

[16] (white). 1 HNMR(CDCl3):δ8.80(s,2H),8.60(d,2H),8.00(d,2H),7.44(dd,2H),7.20(m,6H),6.50(d,4H),6.40(d,2H) HPLC (purity=99.3%) Preparation Example 3 [ka]

[0089] Under nitrogen atmosphere, 3.42g (20.1mmol) of N-(3-pyridine)-phenylamine, 3.84g (20.1mol) of 4-bromochlorobenzene, 0.19mg (0.34mmol) of bis(dibenzylideneacetone)palladium, 0.32mg (0.68mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87g (40.32mmol) of sodium tert-butoxide, and 100ml of xylene were added to a reactor, heated, refluxed, stirred and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100ml of water, filtered and dried to give 5.1g of 4-(N-(3-pyridine)-phenylamino)chlorobenzene. 1 HNMR(CDCl3):δ8.51(s,1H),8.25(d,1H),7.40(dd,1H),7.00(m,4H),6.61(m,1H),6.45-6.40(m,4H) HPLC (purity=99.2%) [ka]

[40]

[0090] Under nitrogen atmosphere, 2.82 g (10.1 mmol) of 4-(N-(3-pyridine)-phenylamino)chlorobenzene, 1.05 g (4.59 mmol) of 3,5-di(trifluoromethyl)aniline, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 3.1 g of crude product. The crude product was then subjected to a pressure of 3×10 -3 The mixture was sublimated at 230°C under reduced pressure to obtain 2.3 g of compound

[40] (white). 1HNMR(CDCl3):δ8.53(s,2H),8.25(d,2H),7.40(dd,2H),7.25(d,2H),7.00(m,5H),6.63(m,4H),6.45(d,4H),6.21(m,8H) HPLC (purity=99.5%) Preparation Example 4 Synthesis of compound

[49] [ka]

[0091] Under nitrogen atmosphere, 14.19g (55mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.76g (25mmol) of 3,5-dibromochlorobenzene, 15.20g (110mmol) of potassium carbonate, 0.70g (1mmol) of bis(triphenylphosphine)palladium(II) dichloride, 125ml of DME and 55ml of water were added to a reactor and reacted under stirring for 6 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300ml of water, washed three times with 300ml of methanol, filtered, and the filter cake was rinsed once with 200ml of methanol, filtered and dried under vacuum to obtain 27.65g of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene. 1 HNMR(DMSO): δ7.68(s,4H),7.61(s,2H),7.60(s,1H),7.48(s,2H) HPLC (purity=98.7%) [ka]

[0092] Under nitrogen atmosphere, 9.00 g (16.8 mmol) of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene, 1.87 g (20.1 mmol) of phenylpyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to give 5.1 g of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-phenyl)amine. 1 HNMR(CDCl3):δ7.67(s,4H),7.61(s,2H),7.02-7.00(m,3H),6.63(m,3H),6.46(d,2H),5.23(s,1H) HPLC (purity=99.3%) [ka]

[49]

[0093] Under nitrogen atmosphere, 5.99 g (10.1 mmol) of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-phenyl)amine, 1.43 g (4.59 mol) of 4,4'-dibromobiphenyl, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100 ml of water three times, filtered, and dried to obtain 5.2 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 280°C under reduced pressure to give 3.5 g of compound

[49] (white). 1HNMR(CDCl3):δ7.67(s,8H),7.60(s,4H),7.23(d,4H),7.02-7.00(m,6H),6.63(m,6H),6.52-6.46(m,8H) HPLC (purity=99.5%) Preparation Example 5 Synthesis of compound

[50] [ka]

[0094] Under nitrogen atmosphere, 14.19g (55mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.76g (25mmol) of 3,5-dibromochlorobenzene, 15.20g (110mmol) of potassium carbonate, 0.70g (1mmol) of bis(triphenylphosphine)palladium(II) dichloride, 125ml of DME and 55ml of water were added to a reactor and reacted under stirring for 6 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300ml of water, washed three times with 300ml of methanol, filtered, and the filter cake was rinsed once with 200ml of methanol, filtered and dried under vacuum to obtain 13.25g of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene. 1 HNMR(DMSO): δ7.68(s,4H),7.61(s,2H),7.60(s,1H),7.48(s,2H) HPLC (purity=98.7%) [ka]

[0095] Under nitrogen atmosphere, 9.00 g (16.8 mmol) of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to give 5.3 g of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-(3-pyridyl))amine. 1 HNMR(CDCl3):δ8.55(s,1H),8.25(d,1H),7.67(s,4H),7.61(s,2H),7.50~7.23(m,2H),7.03(s,1H),6.65(s,2H),5.23(s,1H) HPLC (purity=99.5%) [ka]

[50]

[0096] Under nitrogen atmosphere, 6.00 g (10.1 mmol) of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-(3-pyridyl))amine, 1.43 g (4.59 mol) of 4,4'-dibromobiphenyl, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100 ml of water three times, filtered, and dried to obtain 5.1 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 280°C under reduced pressure to obtain 2.7 g of compound

[50] (white). 1 HNMR(CDCl3):δ8.54(s,2H),8.25(d,2H),7.66(s,8H),7.60(s,4H),7.40(s,2H),7.38~7.23(m,6H),7.03(s,2H),6.64(s,4H),6.50(d,4H) HPLC (purity=99.7%) Preparation Example 6 Synthesis of compound

[67] [ka]

[0097] Under nitrogen atmosphere, 14.19g (55mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.76g (25mmol) of 3,5-dibromochlorobenzene, 15.20g (110mmol) of potassium carbonate, 0.70g (1mmol) of bis(triphenylphosphine)palladium(II) dichloride, 125ml of DME and 55ml of water were added to a reactor and reacted under stirring for 6 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300ml of water, washed three times with 300ml of methanol, filtered, and the filter cake was rinsed once with 200ml of methanol, filtered and dried under vacuum to obtain 27.65g of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene. 1 HNMR(DMSO): δ7.68(s,4H),7.61(s,2H),7.60(s,1H),7.48(s,2H),HPLC(purity)=99.8%) [ka]

[0098] Under nitrogen atmosphere, 9.00 g (16.8 mmol) of 3,5-di(3,5-di(trifluoromethyl)benzene)chlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to give 5.3 g of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-(3-pyridyl))amine. 1 HNMR(CDCl3):δ8.55(s,1H),8.25(d,1H),7.67(s,4H),7.61(s,2H),7.50~7.23(m,2H),7.03(s,1H),6.65(s,2H),5.23(s,1H) HPLC (purity=99.5%) [ka]

[67]

[0099] Under nitrogen atmosphere, 6.00 g (10.1 mmol) of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-(3-pyridyl))amine, 1.43 g (4.59 mmol) of 4,4'-dibromo(3-pyridine), 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100 ml of water three times, filtered, and dried to obtain 4.3 g of crude product. The crude product was subjected to a pressure of 3×10 -3 Sublimation at 290°C and 375°C gave 2.4 g of compound

[67] (light yellow). 1 HNMR(CDCl3):δ8.54(s,2H),8.25(d,2H),7.66(s,8H),7.60(s,4H),7.40(s,2H),7.38~7.23(m,6H),7.03(s,2H),6.64(s,4H),6.50(d,4H) HPLC (purity=99.1%) Preparation Example 7 Synthesis of compound

[70] [ka]

[0100] Under nitrogen atmosphere, 13.75g (55mmol) of 3,5-di(trifluoromethyl)aniline, 6.76g (25mmol) of 3,5-dibromochlorobenzene, 15.20g (110mmol) of potassium carbonate, 0.70g (1mmol) of bis(triphenylphosphine)palladium(II) dichloride, 125ml of DME and 55ml of water were added to a reactor, stirred and refluxed for 6 hours, cooled to room temperature, rotary evaporated, washed 3 times with 300ml of water, washed 3 times with 300ml of methanol, filtered, rinsed the filter cake once with 200ml of methanol, filtered and dried under vacuum to obtain 27.45g of 3,5-di(3,5-di(trifluoromethyl)benzene)aniline. 1 HNMR(DMSO): δ7.67(s,4H),7.60(s,2H),7.07(s,1H),6.62(s,2H),5.2(s,1H) HPLC (purity=99.1%) [ka]

[0101] Under nitrogen atmosphere, 8.68 g (16.8 mmol) of 3,5-di(3,5-di(trifluoromethyl)benzene)aniline, 4.82 g (20.1 mmol) of 5-phenyl-2-bromothiophene, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to give 10.23 g of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-2-(5-benzothiophene))amine. 1 HNMR(CDCl3):δ7.67(s,4H),7.61(s,2H),7.50~7.21(m,5H),7.05(s,1H),6.65(s,2H),6.60(d,1H),6.31(d,1H),5.21(s,1H) HPLC (purity=99.5%) [ka]

[70]

[0102] Under nitrogen atmosphere, 6.87 g (10.1 mmol) of N-((3,5-di(3,5-di(trifluoromethyl)benzene)phenyl)-2-(5-benzothiophene))amine, 1.07 g (4.59 mol) of p-dibromobenzene, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100 ml of water three times, filtered, and dried to obtain 5.3 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 370°C under reduced pressure to give 4.1 g of compound

[70] (light yellow). 1 HNMR(CDCl3):δ7.67(s,8H),7.60(s,4H),7.50~7.21(m,10H),7.06(s,2H),6.65(s,4H),6.60(d,2H),6.31(d,2H),6.20(d,4H) HPLC (purity=99.2%) Preparation Example 8 Synthesis of compound

[71] [ka]

[0103] In a nitrogen atmosphere, 6.19 g (24 mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.75 g (25 mmol) of 3,5-dibromochlorobenzene, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted at 60° C. for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, dried under vacuum, and passed through a column (petroleum ether:toluene=1:1) to obtain 9.21 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene. 1 HNMR(DMSO):δ7.67(s,2H),7.61-7.40(m,4H) HPLC (purity=99.2%) [ka]

[0104] Under nitrogen atmosphere, 9.21 g (23.0 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene, 5.20 g (23.0 mmol) of 4-phenylcarbamoylphenylboronic acid, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted under reflux for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, and dried under vacuum to obtain 9.32 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-(4-biphenylcarbamoylbenzene)chlorobenzene. 1 HNMR(CDCl3):δ7.76-7.58(m,10H),7.46-7.34(m,5H) HPLC (purity=99.1%) [ka]

[0105] Under a nitrogen atmosphere, 8.45 g (16.8 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-(4-phenylcarbamoylbenzene)chlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were placed in a reactor, and the mixture was reacted for 4 hours while being heated under reflux and stirred. Cooled to room temperature, rotary evaporated, washed with 3×100 mL water, filtered, and dried to give 8.41 g of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-(4-phenylcarbamoylbenzene)phenyl)-(3-pyridyl)amine. 1HNMR(CDCl3):δ8.51(s,1H),8.22(d,1H),7.77-7.70(m,4H),7.65-7.57(m, 5H),7.45-7.36(m,4H),7.25(d,1H),7.05(s,1H),6.65(s,2H),5.11(s,1H) HPLC (purity=99.5%) [ka]

[71]

[0106] Under nitrogen atmosphere, 5.68 g (10.1 mmol) of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-(4-phenylcarbamoylbenzene)phenyl)-(3-pyridyl))amine, 1.07 g (4.59 mol) of p-dibromobenzene, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 4.34 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 350°C under reduced pressure to give 3.7 g of compound

[71] (light yellow). 1 HNMR(CDCl3):δ8.52(s,2H),8.23(d,2H),7.77-7.71(m,8H),7.66-7.57(m, 10H),7.45-7.35(m,8H),7.25(d,2H),7.05(s,2H),6.63(s,4H),6.20(d,4H) HPLC (purity=98.9%) Preparation Example 9 Synthesis of compound

[91] [ka]

[0107] In a nitrogen atmosphere, 6.19 g (24 mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.75 g (25 mmol) of 3,5-dibromochlorobenzene, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted at 60° C. for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, dried under vacuum, and passed through a column (petroleum ether:toluene=1:1) to obtain 9.21 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene. 1 HNMR(DMSO):δ7.67(s,2H),7.61-7.40(m,4H) HPLC (purity=99.2%) [ka]

[0108] Under nitrogen atmosphere, 9.21 g (23.0 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene, 8.97 g (23.0 mmol) of 3,5-diadamantylphenylboronic acid, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted under reflux for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, and dried under vacuum to obtain 12.41 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-(3,5-diadamantyl)chlorobenzene. 1 HNMR(CDCl3):δ7.67(s,2H),7.60(s,2H),7.45(s,2H),7.30(s,3H),1.81(m,4H),1.56(m,8H),1.43(m,4H),1.41(m,6H),1.18(m,8H) HPLC (purity=98.7%) [ka]

[0109] Under a nitrogen atmosphere, 11.22 g (16.8 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-(3,5-diadamantyl)chlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were placed in a reactor, and the mixture was heated, refluxed, and stirred to react for 4 hours. Cooled to room temperature, rotary evaporated, washed with 3 x 100 mL water, filtered and dried to give 11.21 g of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-(3,5-diadamantyl)phenyl)-(3-pyridyl)amine.

[0110] 1 HNMR(CDCl3):δ8.52(s,1H),8.23(d,1H),7.67(s,2H),7.60(s,1H),7.40(s,1H),7.30(m,4H),7.06 (s,1H),6.64(s,2H),5.21(s,1H),1.81(m,4H),1.56(m,8H),1.43(m,4H),1.41(m,6H),1.18(m,8H) HPLC (purity=99.1%) [ka]

[91]

[0111] Under nitrogen atmosphere, 7.33 g (10.1 mmol) of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-(3,5-diadamantyl)phenyl)-(3-pyridyl)amine, 1.07 g (4.59 mol) of p-dibromobenzene, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 8 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 10.45 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 390°C under reduced pressure to give 7.3 g of compound

[91] (light yellow). δ8.52(s,2H),8.23(d,2H),7.67(s,4H),7.60(s,2H),7.40(s,2H),7.30(m,8H),7.06(s,2H), 6.64(s,4H),6.20(d,4H),1.81(m,8H),1.56(m,16H),1.43(m,8H),1.41(m,12H),1.18(m,16H) HPLC (purity=99.2%) Preparation Example 10 Synthesis of compound

[93] [ka]

[0112] In a nitrogen atmosphere, 6.19 g (24 mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.75 g (25 mmol) of 3,5-dibromochlorobenzene, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted at 60° C. for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, dried under vacuum, and passed through a column (petroleum ether:toluene=1:1) to obtain 9.21 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene. 1 HNMR(DMSO):δ7.67(s,2H),7.61-7.40(m,4H) HPLC (purity=99.2%) [ka]

[0113] Under nitrogen atmosphere, 9.21 g (23.0 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene, 5.66 g (23.0 mmol) of pyreneboronic acid, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted under reflux for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, and dried under vacuum to obtain 10.12 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-pyrenylchlorobenzene. 1 HNMR(CDCl3):δ8.22(s,2H),8.00(d,2H),7.80(m,1H),7.71-7.67(m,6H),7.60-7.58(m,2H),7.45(s,2H) HPLC (purity=99.3%) [ka]

[0114] Under nitrogen atmosphere, 8.80 g (16.8 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-pyrenylchlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to give 8.41 g of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-pyrenyl)-(3-pyridyl)amine. 1 HNMR(CDCl3):δ8.53(s,1H),8.21(m,3H),8.00(d,2H),7.81(m,1H),7.71-7.67(m ,6H),7.60(s,1H),7.41(m,1H),7.25(d,1H),7.06(s,1H),6.64(s,2H),5.21(s,H) HPLC (purity=99.5%) [ka]

[93]

[0115] Under nitrogen atmosphere, 5.88 g (10.1 mmol) of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-pyrenyl)-(3-pyridyl))amine, 1.07 g (4.59 mol) of p-dibromobenzene, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, filtered, and dried to obtain 4.12 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 370°C under reduced pressure to give 3.4 g of compound

[93] (yellow). 1 HNMR(CDCl3):δ8.53(s,1H),8.21(m,3H),8.00(d,2H),7.82(m,1H),7.71-7.67(m, 6H),7.60(s,1H),7.40(m,1H),7.25(d,1H),7.06(s,1H),6.64(s,2H),6.21(d,4H) HPLC (purity=99.1%) Preparation Example 11 Synthesis of compound

[94] [ka]

[0116] In a nitrogen atmosphere, 6.19 g (24 mmol) of 3,5-di(trifluoromethyl)phenylboronic acid, 6.75 g (25 mmol) of 3,5-dibromochlorobenzene, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME, and 25 ml of water were added to a reactor and reacted at 60° C. for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered, dried under vacuum, and passed through a column (petroleum ether:toluene=1:1) to obtain 9.21 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene. 1 HNMR(DMSO):δ7.67(s,2H),7.61-7.40(m,4H) HPLC (purity=99.2%) [ka]

[0117] In a nitrogen atmosphere, 9.21 g (23.0 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-bromochlorobenzene, 8.28 g (23.0 mmol) of 9,9'-spirobifluoreneboronic acid, 3.4 g (25 mmol) of potassium carbonate, 0.70 g (1 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 60 ml of DME and 25 ml of water were added to a reactor and reacted under reflux for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 300 ml of water, washed three times with 300 ml of methanol, filtered, and the filter cake was rinsed once with 200 ml of methanol, filtered and dried under vacuum to obtain 11.21 g of 5-(3,5-di(trifluoromethyl)phenyl)-3-9,9'-spirobifluorenechlorobenzene. 1 HNMR(CDCl3):δ7.90-7.72(m,5H),7.67-7.45(m,8H),7.38-7.28(m,4H),7.19-7.16(m,4H) HPLC (purity=99.2%) [ka]

[0118] Under a nitrogen atmosphere, 10.72 g (16.8 mmol) of 5-(3,5-di(trifluoromethyl)phenyl)-3-9,9'-spirobifluorenechlorobenzene, 1.90 g (20.1 mmol) of 3-aminopyridine, 0.19 mg (0.34 mmol) of bis(dibenzylideneacetone)palladium, 0.32 mg (0.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87 g (40.32 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, and the mixture was heated, refluxed, and stirred to react for 4 hours. Cool to room temperature, rotary evaporate, wash with 3 x 100 mL water, filter and dry to give 9.38 g of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-9,9'-spirobifluorene)-(3-pyridyl)amine. 1 HNMR(CDCl3):δ8.53(s,1H),8.23(d,1H),7.90-7.72(m,5H),7.67-7.45(m,5H ),7.38-7.28(m,6H),7.19-7.16(m,4H),7.06(s,1H),6.64(s,2H),5.12(s,1H) HPLC (purity=99.7%) [ka]

[94]

[0119] Under nitrogen atmosphere, 7.04 g (10.1 mmol) of N-(5-(3,5-di(trifluoromethyl)phenyl)-3-9,9'-spirobifluorene)-(3-pyridyl))amine, 1.07 g (4.59 mol) of p-dibromobenzene, 0.052 mg (0.09 mmol) of bis(dibenzylideneacetone)palladium, 0.087 mg (0.18 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 2.12 g (22.04 mmol) of sodium tert-butoxide, and 50 ml of xylene were added to a reactor, heated to reflux, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100 ml of water three times, filtered, and dried to obtain 5.29 g of crude product. The crude product was subjected to a pressure of 3×10 -3 The mixture was sublimated at 380°C under reduced pressure to give 2.3 g of compound

[94] (yellow). 1 HNMR(CDCl3):δ8.53(s,1H),8.23(d,1H),7.90-7.72(m,5H),7.67-7.45(m,5H ),7.38-7.28(m,6H),7.19-7.16(m,4H),7.06(s,1H),6.64(s,2H),6.20(d,4H) HPLC (purity=99.5%) Preparation Example 12 [ka]

[0120] Under nitrogen atmosphere, 3.85g (16.8mmol) of 3,5-di(trifluoromethyl)aniline, 4.88g (16.8mmol) of 3,5-di(trifluoromethyl)bromobenzene, 0.19mg (0.34mmol) of bis(dibenzylideneacetone)palladium, 0.32mg (0.68mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87g (40.32mmol) of sodium tert-butoxide, and 100ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed 3 times with 100ml water, washed 3 times with 100ml methanol, and dried to give 7.1g of bis(bis(trifluoromethyl)phenyl)amine. 1 HNMR(CDCl3):δ7.02(s,2H),6.40(s,4H),4.00(s,1H) HPLC (purity=99.9%) [ka]

[0121] Under nitrogen atmosphere, 7.10 g (16.1 mmol) of bis(bis(trifluoromethyl)phenyl)amine, 4.13 g (16.1 mmol) of 4-bromo-2-trifluoromethylchlorobenzene, 0.18 mg (0.33 mmol) of bis(dibenzylideneacetone)palladium, 0.31 mg (0.66 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.70 g (38.64 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, washed three times with 100 ml of methanol, and dried to give 9.2 g of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene. 1 HNMR(CDCl3):δ7.01(s,2H),6.95(s,1H),6.65(s,4H),6.55(s,1H),6.40(s,1H) HPLC (purity=99.1%) [ka]

[0122] Under nitrogen atmosphere, 4.6 g (7.4 mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene, 1.89 g (7.4 mmol) of bispinacolatodiboron, 0.09 mg (0.16 mmol) of bis(dibenzylideneacetone)palladium, 0.15 mg (0.31 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 1.90 g (19.31 mmol) of potassium acetate, and 100 ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, washed three times with 100 ml of methanol, and dried to give 5.0 g of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylphenyl pinacol ester. 1 HNMR(CDCl3):δ7.01(s,2H),6.91(s,1H),6.72(s,1H),6.64(s,4H),6.54(s,1H),1.26(s,12H) HPLC (purity=99.5%) [ka]

[99]

[0123] Under nitrogen atmosphere, 4.35g (7.0mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene, 5.00g (7.0mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylphenyl pinacol ester, 1.33g (9.8mmol) of potassium carbonate, 0.49g (0.7mmol) of bis(triphenylphosphine)palladium(II) dichloride, 24ml of DME and 10ml of water were added to a reactor and reacted at 60°C for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100ml of water, washed three times with 100ml of methanol, filtered, rinsed the filter cake once with 20ml of methanol, filtered, dried in vacuum and passed through a column (petroleum ether:dichloromethane=1:1) to obtain 8.12g of compound

[99] (pink). 1 HNMR(DMSO): δ7.12(s,2H),7.00(s,4H),6.72(s,2H),6.65(s,8H),6.55(s,2H) HPLC (purity=99.9%) Preparation Example 13 [ka]

[0124] Under nitrogen atmosphere, 3.85g (16.8mmol) of 3,5-di(trifluoromethyl)aniline, 4.88g (16.8mmol) of 3,5-di(trifluoromethyl)bromobenzene, 0.19mg (0.34mmol) of bis(dibenzylideneacetone)palladium, 0.32mg (0.68mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87g (40.32mmol) of sodium tert-butoxide, and 100ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed 3 times with 100ml water, washed 3 times with 100ml methanol, and dried to give 7.1g of bis(bis(trifluoromethyl)phenyl)amine. 1HNMR(CDCl3):δ7.02(s,2H),6.40(s,4H),4.00(s,1H) HPLC (purity=99.9%) [ka]

[0125] Under nitrogen atmosphere, 7.10 g (16.1 mmol) of bis(bis(trifluoromethyl)phenyl)amine, 3.04 g (16.1 mmol) of 4-bromochlorobenzene, 0.18 mg (0.33 mmol) of bis(dibenzylideneacetone)palladium, 0.31 mg (0.66 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.70 g (38.64 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, washed three times with 100 ml of methanol, and dried to give 8.81 g of 4-bis(bis(trifluoromethyl)phenyl)amino-chlorobenzene. 1 HNMR(CDCl3):δ7.01(s,4H),6.65(s,4H),6.40(s,2H) HPLC (purity=99.1%) [ka]

[0126] Under nitrogen atmosphere, 8.15g (14.8mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene, 3.78g (14.8mmol) of bispinacolatodiboron, 0.18mg (0.32mmol) of bis(dibenzylideneacetone)palladium, 0.3mg (0.62mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.80g (38.62mmol) of potassium acetate, and 100ml of xylene were added to a reactor, heated, refluxed, stirred and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed 3 times with 100ml water, washed 3 times with 100ml methanol, and dried to give 9.13g of 4-bis(bis(trifluoromethyl)phenyl)amino-phenyl pinacol ester. 1 HNMR(CDCl3):δ7.01(s,4H),6.64(s,4H),6.54(s,2H),1.26(s,12H) HPLC (purity=99.5%) [ka]

[0102]

[0127] In a nitrogen atmosphere, 9.02 g (14.0 mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylphenyl pinacol ester, 2.60 g (7.0 mmol) of 2,5-bistrifluoromethyl-1,4-dibromobenzene, 1.33 g (9.8 mmol) of potassium carbonate, 0.49 g (0.7 mmol) of bis(triphenylphosphine)palladium(II) dichloride, 24 ml of DME, and 10 ml of water were added to a reactor, and the mixture was reacted at 60° C. for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, washed three times with 100 ml of methanol, filtered, and the filter cake was rinsed once with 20 ml of methanol, filtered, dried in vacuum, and passed through a column (petroleum ether:dichloromethane=1:1) to obtain 12.31 g of compound

[0102] (white). 1HNMR(DMSO): δ7.63(s,2H),7.23(d,4H),7.00(s,4H),6.65(s,8H),6.52(d,4H) HPLC (purity=99.7%) Preparation Example 14 [ka]

[0128] Under nitrogen atmosphere, 3.85g (16.8mmol) of 3,5-di(trifluoromethyl)aniline, 3.76g (16.8mmol) of 4-trifluoromethylbromobenzene, 0.19mg (0.34mmol) of bis(dibenzylideneacetone)palladium, 0.32mg (0.68mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.87g (40.32mmol) of sodium tert-butoxide, and 100ml of xylene were added to a reactor, heated, refluxed, stirred, and reacted for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100ml water, washed three times with 100ml methanol, and dried to give 6.21g of N-(3,5-di(trifluoromethyl)phenyl)-(4-trifluoromethylphenyl)amine. 1 HNMR(CDCl3):δ7.21(s,2H),7.02(s,1H),6.64(s,2H),6.38(s,2H),4.00(s,1H) HPLC (purity=99.1%)

[0129] [ka] Under nitrogen atmosphere, 6.00 g (16.1 mmol) of bis(bis(trifluoromethyl)phenyl)amine, 4.13 g (16.1 mmol) of 4-bromo-2-trifluoromethylchlorobenzene, 0.18 mg (0.33 mmol) of bis(dibenzylideneacetone)palladium, 0.31 mg (0.66 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 3.70 g (38.64 mmol) of sodium tert-butoxide, and 100 ml of xylene were added to a reactor, heated, refluxed, and stirred for 4 hours. The mixture was cooled to room temperature, rotary evaporated, washed three times with 100 ml of water, washed three times with 100 ml of methanol, and dried to give 8.24 g of 4-((N-(3,5-di(trifluoromethyl)phenyl)-(4-trifluoromethylphenyl))amino-2-trifluoromethylchlorobenzene. 1 HNMR(CDCl3):δ7.21(s,2H),7.01(s,1H),6.95(s,1H),6.65(s,2H),6.55(s,1H),6.40(s,3H) HPLC (purity=99.0%) [ka]

[0130] Under a nitrogen atmosphere, 4.11 g (7.4 mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene, 1.89 g (7.4 mmol) of bis-pinacolatodiboron, 0.09 mg (0.16 mmol) of bis(dibenzylideneacetone)palladium, 0.15 mg (0.31 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropyldiphenyl, 1.90 g (19.31 mmol) of potassium acetate, and 100 ml of xylene were added to a reactor, and the mixture was heated, refluxed, and stirred to react for 4 hours. Cooling to room temperature, rotary evaporation, washing with 3×100 ml water, 3×100 ml methanol, and drying gave 4.50 g of 4-((N-(3,5-di(trifluoromethyl)phenyl)-(4-trifluoromethylphenyl))amino-2-trifluoromethylphenyl pinacol ester. 1 HNMR(CDCl3):δ7.21(s,2H),7.01(s,1H),6.91(s,1H),6.72(s,1H),6.64(s,2H),6.54(s,1H),6.38(s,2H),1.26(s,12H) HPLC (purity=98.8%) [ka]

[0105]

[0131] Under nitrogen atmosphere, 3.85g (7.0mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylchlorobenzene, 4.50g (7.0mmol) of 4-bis(bis(trifluoromethyl)phenyl)amino-2-trifluoromethylphenyl pinacol ester, 1.33g (9.8mmol) of potassium carbonate, 0.49g (0.7mmol) of bis(triphenylphosphine)palladium(II) dichloride, 24ml of DME and 10ml of water were added to a reactor and reacted at 60°C for 3 hours. The mixture was cooled to room temperature, rotary evaporated, washed with 100ml of water three times, washed with 100ml of methanol three times, filtered, rinsed the filter cake once with 20ml of methanol, filtered, dried in vacuum and passed through a column (petroleum ether:dichloromethane=1:1) to obtain 7.01g of compound

[0105] (white). 1 HNMR(DMSO): δ7.21(s,4H),7.12(s,2H),7.00(s,2H),6.72(s,2H),6.65(s,4H),6.55(s,2H),6.38(s,4H) HPLC (purity=99.9%) Example 1

[0132] (1) Refractive index measurement A non-alkali glass substrate (Asahi Glass Co., Ltd., AN100) was subjected to UV ozone cleaning treatment for 20 minutes, and then placed in a vacuum deposition apparatus. The degree of vacuum in the apparatus was 1×10 -3The chamber was evacuated to a vacuum of over 100 Pa, and compound

[15] was evaporated to a thin film of about 50 nm by electrical resistance heating deposition at a deposition rate of 0.1 nm / s.

[0133] The refractive index and extinction coefficient of the thin film samples prepared above were measured at Toray Research Center, Inc., using an ellipsoidal polarization spectrometer (JA Woollam M-2000) as the measuring instrument.

[0134] The refractive index of compound

[15] at 460 nm was 1.67. The refractive index of TBDB at 460 nm measured by a similar method was 2.06.

[0135] (2) Preparation and evaluation of organic light-emitting devices The non-alkali glass was ultrasonically cleaned with isopropyl alcohol for 15 minutes, and then UV ozone cleaned in the atmosphere for 30 minutes. Using the sputtering method, 100 nm of silver (Ag) and 10 nm of ITO were sequentially deposited on the non-alkali glass to form a reflective anode. After the reflective anode was subjected to UV ozone cleaning for 10 min, a hole injection layer (NPD and F4-TCNQ (weight ratio 97:3), 50 nm), a hole transport layer (NPD, 80 nm), a blue light-emitting layer (BH and BD (weight ratio 97:3, 20 nm), an electron transport layer (Alq3, 35 nm), and an electron injection layer (LiF, 1 nm) were deposited on the anode by vacuum deposition in that order, and then Mg and Ag (weight ratio 10:1, 15 nm) were co-deposited to form a semi-transparent cathode. Then, a 10 nm-thick compound

[15] -based second capping layer and a 50 nm-thick compound [TBDB]-based first capping layer were deposited on the semi-transparent cathode in that order. Finally, an alkali-free glass sealing plate was sealed with epoxy resin adhesive in a glove box with a dry nitrogen atmosphere to form a light-emitting device.

[0136] A direct current of 10 mA / cm2 was applied to the above light-emitting element at room temperature in the atmosphere, and the luminance and color purity of the light emitted from the sealing plate were measured using a spectroradiometer (CS1000, Konica Minolta, Inc.). The measured values ​​were a luminous efficiency of 3.4 cd / A and a color purity of CIE(x,y)=(0.135, 0.048). Example 2

[0137] The same as Example 1, except that the second capping layer is compound

[16] .

[0138] The refractive index of compound

[16] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 3

[0139] Same as Example 1, except that the second capping layer is compound

[40] .

[0140] The refractive index of compound

[40] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 4

[0141] Same as Example 1, except that the second capping layer is compound

[49] .

[0142] The refractive index of compound

[49] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 5

[0143] Same as Example 1, except that the second capping layer is compound

[50] .

[0144] The refractive index of compound

[50] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 6

[0145] Same as Example 1, except that the second capping layer is compound

[67] .

[0146] The refractive index of compound

[67] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 7

[0147] Same as Example 1, except that the second capping layer is compound

[70] .

[0148] The refractive index of compound

[70] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 8

[0149] Same as Example 1, except that the second capping layer is compound

[71] .

[0150] The refractive index of compound

[71] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 9

[0151] Same as Example 1, except that the second capping layer is compound

[91] .

[0152] The refractive index of compound

[91] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 10

[0153] Same as Example 1, except that the second capping layer is compound

[93] .

[0154] The refractive index of compound

[93] was measured, and the compound was evaluated for its performance in an organic light-emitting device. The evaluation results are shown in Table 1. Example 11

[0155] Same as Example 1, except that the second capping layer is compound

[94] .

[0156] The refractive index of compound

[94] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 12

[0157] Same as Example 1, except that the second capping layer is compound

[99] .

[0158] The refractive index of compound

[94] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 13

[0159] Same as Example 1, except that the second capping layer is compound

[0102] .

[0160] The refractive index of compound

[94] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 14

[0161] Same as Example 1, except that the second capping layer is compound

[0105] .

[0162] The refractive index of compound

[94] was measured, and its performance in an organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 15

[0163] The same as Example 1, except that the second capping layer was compound

[99] and the first capping layer was compound ZJF.

[0164] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 16

[0165] The same as in Example 1, except that the second capping layer was the compound

[99] and the first capping layer was the compound LXY.

[0166] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 17

[0167] The same as Example 1, except that the second capping layer was the compound TBDB and the first capping layer was the compound

[99] .

[0168] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 18

[0169] The same as Example 1, except that the second capping layer is compound

[50] and the first capping layer is compound

[91] .

[0170] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Example 19

[0171] The same as Example 1 except that the second capping layer was compound

[50] and there was no first capping layer.

[0172] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 1

[0173] This is the same as Example 1, except that the second capping layer is TBDB and there is no first capping layer.

[0174] The organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 2

[0175] The same as Example 1, except that the second capping layer was TBDB and the first capping layer was NPD.

[0176] The refractive index of the compound NPD was measured, and the organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 3

[0177] The same as Example 1, except that the second capping layer was TBDB and the first capping layer was Alq3.

[0178] The refractive index of the compound Alq3 was measured, and the organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 4

[0179] Same as Example 1, except that the second capping layer is DZ1.

[0180] The refractive index of the compound DZ1 was measured, and the organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 5

[0181] Same as Example 1, except that the second capping layer is DZ1.

[0182] The refractive index of the compound DZ1 was measured, and the organic light-emitting device was evaluated. The evaluation results are shown in Table 1. Comparative Example 6

[0183] The same as Example 1, except that the second capping layer was CZX and the first capping layer was TBDB.

[0184] The refractive index of the compound CZX was measured, and the organic light-emitting device was evaluated. The evaluation results are shown in Table 1.

[0185] [Table 1]

[0186] In the table, n1(460) is the refractive index of the second capping layer when the wavelength is 460 nm, and n2(460) is the refractive index of the first capping layer when the wavelength is 460 nm.

[0187] As shown in Table 1 above, Comparative Example 1 is a technology that is currently commonly used, and compared to Comparative Example 1, the light-emitting elements of Examples 1 to 16 can all improve the luminous efficiency while maintaining high color purity. Among them, a comparison between Example 2 and Example 3 shows that the compound

[40] substituted with an amine has higher thermal stability, and when the refractive index is close, the compound

[40] substituted with an amine has higher luminous efficiency. A comparison between Example 4 and Example 5 shows that, when the refractive index is close, Example 5 with a heteroatom is compared with Example 4 without a heteroatom and has a similar structure, Example 5 with a heteroatom has higher luminous efficiency. A comparison between Example 9, Example 10, and Example 7 shows that, when the number of trifluoromethyl groups is the same, the compounds of Examples 9 and 10 incorporating condensed rings or spiro rings have higher refractive indexes, but their luminous efficiency is somewhat reduced. Example 13 uses two types of materials with a refractive index below 1.7, and Comparative Examples 2 and 3 use two types of materials with a refractive index above 1.8, but the luminous efficiency is not improved from that of the conventional technology. Comparing the three examples of Comparative Example 6, Example 14, and Example 12, it can be seen that the more trifluoromethyl groups there are, the lower the refractive index, and the better the overall optical performance. Example 19 only uses a capping layer material with a refractive index below 1.7, and the luminous efficiency is not improved from the conventional technology. Comparative Example 4 uses a boron complex compound DZ1, which maintains high color purity while significantly improving the luminous efficiency compared to Comparative Example 1, and can reach a luminous efficiency close to that of Example 5 compared to Example 5. However, the compound is prone to clogging during deposition, so the device performance is unstable. Comparative Example 5 is a second experiment using exactly the same materials as Comparative Example 4 under exactly the same conditions, and its luminous efficiency is somewhat weakened compared to Comparative Example 4. This is because the control of the film thickness of the second capping layer deposited after clogging is unstable, and the resonant cavity cannot perform its performance. From the perspective of quality assurance and industrial production, clogging performance increases the defect rate and raises production costs.Comparative Example 6 uses a compound CZX that does not contain a trifluoromethyl group. The refractive index of this compound is 1.83, which is a small difference from that of the light-emitting layer, and the difference from that of the first capping layer material is less than 0.3. The luminous efficiency is obviously lower than that of conventional technology.

[0188] All patent and non-patent documents referred to in this specification are incorporated herein by reference. The term "multiple" as used herein includes all situations of one or more, i.e., "one or more" includes one, two, three, etc. In this specification, when an upper limit and a lower limit are described for a certain numerical range, or when a numerical range is described in a manner of combining an upper limit and a lower limit, each upper limit and each lower limit described therein can be arbitrarily combined to form a new numerical range, which is to be considered as the same as the described form of the numerical range consisting of the combination directly stated. Those skilled in the art can change and improve the present invention without departing from the spirit of the present invention, and these are also included in the scope of the present invention.

Claims

1. An organic light-emitting device comprising a substrate, a first electrode, an emitting layer comprising one or more organic layer films, and a second electrode, the organic light-emitting device further comprising a capping layer, the capping layer being on the second electrode, the capping layer comprising a first capping layer and a second capping layer, the first capping layer having a refractive index of 1.8 or more and the second capping layer having a refractive index of 1.7 or less, and the second capping layer comprising an aromatic amine compound having a structure represented by the following general formula 4: 【Chemistry 1】 [General formula 4] Among them, Ar １ , Ar ２ , Ar ３ each represents a group consisting of a substituted or unsubstituted aryl group and / or a heteroaryl group, １ , Ar ２ , Ar ３ At least one of the Ar １ , Ar ２ , Ar ３ the substituents of are one or more selected from hydrogen, deuterium, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable heterocyclic group, a substitutable alkenyl group, a substitutable cycloalkenyl group, a substitutable alkynyl group, a substitutable alkoxyl group, a substitutable alkylthio group, a substitutable aryl ether group, a substitutable aryl thioether group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable carbonyl group, a substitutable carboxyl group, a substitutable oxycarbonyl group, a substituted carbamoyl group, a substituted silyl group, a substituted alkylamino group, and a substituted arylamino group; wherein Ar 4 and Ar 5 each represent a group consisting of a substituted or unsubstituted aryl group and / or heteroaryl group, the substituents of Ar 4 and Ar 5 are one or more selected from hydrogen, deuterium, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable heterocyclic group, a substitutable alkenyl group, a substitutable cycloalkenyl group, a substitutable alkynyl group, a substitutable alkoxyl group, a substitutable alkylthio group, a substitutable aryl ether group, a substitutable arylthioether group, a substitutable aryl group, a substitutable heteroaryl group, a substitutable carbonyl group, a substitutable carboxyl group, a substitutable oxycarbonyl group, a substitutable carbamoyl group, a substitutable silyl group, a substitutable alkylamino group, and a substitutable arylamino group, and n1 to n4 each represent an integer of 0 to 5, and n5 represents an integer of 2 to 5, wherein n1, n2, n3, n4, and n5 are not all 0 at the same time.

2. The aromatic amine compound is represented by the following general formula 5: 【Chemistry 2】 [General formula 5] n ６ , n ７ is an integer from 0 to 5, １ , n ２ , n ３ , n ４ , n ６ , n ７ are not simultaneously zero. The organic light-emitting device according to claim 1 .

3. The Ar ２ The organic light-emitting device according to claim 1 , wherein is selected from an aryl or heteroaryl group that is not a fused ring or a spiro ring.

4. n １ +n ２ +n ３ +n ４ The organic light-emitting device according to claim 1 , wherein the n-th order is 0.01 or 0.

1.

5. The Ar ２ The organic light-emitting device of claim 1 , wherein is selected from an aryl or heteroaryl group that is not a fused ring or a spiro ring.

6. n １ +n ２ The organic light-emitting device according to claim 1 , wherein:

7. The organic light emitting device according to claim 1, wherein the first capping layer has a refractive index of 1.8 or more, and the second capping layer has a refractive index of 1.5 to 1.

7.

8. The organic light emitting device according to claim 1 , wherein the difference in refractive index between the first capping layer and the second capping layer is 0.3 or more.

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