Fluoranthene derivative, light-emitting element, and photoelectric conversion element

Abstract

The invention provides a fluoranthene derivative, a photoelectric conversion element containing the fluoranthene derivative, and a light-emitting element containing the fluoranthene derivative. The fluoranthene derivative according to the present invention uses a substituent containing a heteroatom, and adjusts the number of aza-benzene-based hosts and the nitrogen content thereof to control the amount of electrons that can transport in molecules, thereby providing an organic thin-film light-emitting element that simultaneously achieves high light-emitting efficiency, low driving voltage, and long endurance life.

Description

Technical Field

[0001] The present invention relates to a light-emitting element that can convert electric energy into light and materials used in the light-emitting element. The present invention can be used in fields such as display elements, flat panel displays, backlights, lighting, interior decoration, signs, billboards, electronic cameras, virtual reality, augmented reality, smart watches, mobile phones, laptops, tablets, displays, in-vehicle displays, in-vehicle tail lights, televisions, and optical signal generators. Background Art

[0002] In recent years, research on organic thin-film light-emitting elements, also known as organic light-emitting diodes (OLEDs), has become increasingly active. When electrons injected from the cathode and holes injected from the anode recombine in the organic light-emitting body sandwiched between the two electrodes, the above-mentioned organic thin-film light-emitting element emits light. This light-emitting element is characterized by a small thickness, can emit light with high brightness at a low driving voltage, and can achieve multi-color light emission by selecting a light-emitting material, so it has attracted much attention.

[0003] Since the organic thin-film element was revealed by Tang (C.W.Tang) of Eastman Kodak Company et al. to be able to emit light with high brightness, a large number of practical studies have been carried out. Nowadays, OLEDs have been popularized in fields such as bracelets, mobile phones, and televisions. However, there are still many technical problems, and one of the major problems is to simultaneously achieve high efficiency and long life of the element.

[0004] OLEDs must satisfy the improvement of luminous efficiency, the reduction of driving voltage, and the improvement of durability. Among them, the simultaneous achievement of luminous efficiency and durable life is a major problem. However, it is difficult to sufficiently reduce the driving voltage of the element using the existing technologies (Patent Documents 1-6), and even if the driving voltage can be reduced, the luminous efficiency and durable life of the element are not sufficient. On the other hand, as the trend of OLEDs fully replacing LCDs in the display industry to increase market share becomes increasingly strong, a simpler process to reduce the overall factory operation difficulty and cost has also become an important technical index. As described above, a technology that can simultaneously achieve high luminous efficiency, low driving voltage, durable life, and a simple manufacturing process has been found.

[0005] [Prior Art Documents]

[0006] [Patent Documents]

[0007] [Patent Document 1] International Publication No. 2008 / 059713

[0008] [Patent Document 2] International Publication No. 2007 / 100010

[0009] [Patent Document 3] International Publication No. 2012 / 108388

[0010] [Patent Document 4] International Publication No. WO2013 / 065213

[0011] [Patent Document 5] International Publication No. WO2014 / 057874

[0012] [Patent Document 6] International Publication No. WO2015 / 182547. SUMMARY OF THE INVENTION

[0013] [Problems to be Solved by the Invention]

[0014] An object of the present invention is to solve the problems of the above-mentioned prior art, and to provide an organic thin film light emitting element with improved luminous efficiency, driving voltage, durability, and a simple manufacturing process.

[0015] [Means for Solving the Problems]

[0016] The present invention controls the amount of electrons with transporting ability in the molecule by using a substituent containing a heteroatom and adjusting the number and nitrogen content of the azabenzene-based host, thereby regulating the luminous efficiency, driving voltage, and durability. In addition, by increasing the substituent containing a heteroatom, the response sensitivity of electron release during metal doping is reduced, thereby improving the process window.

[0017] The present invention provides a fluoranthene derivative having a structure represented by the following General Formula 1.

[0018] [General Formula 1]

[0019]

[0020] A, B, C, D, E, F, and G are each independently selected from a single bond, a phenyl group which may be substituted, or a monocyclic heteroaryl group which may be substituted;

[0021] At least one of A, B, C, F, and G is a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group

[0022] a, b, c, d, and e are each independently selected from 0 or 1;

[0023] When F is a monocyclic heteroaryl group which may be substituted or a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group, d is selected from 1;

[0024] When G is a monocyclic heteroaryl group which may be substituted or a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group, e is selected from 1;

[0025] Only one of A, B, and C is ortho-substituted;

[0026] The substituents of the above-mentioned phenyl or heteroaryl that can be substituted are each independently selected from one or more of hydrogen, deuterium, cyano, alkyl that can be substituted, cycloalkyl that can be substituted, heterocyclic group that can be substituted, alkenyl that can be substituted, cycloalkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkylthio that can be substituted, aryl ether group that can be substituted, aryl thioether group that can be substituted, aryl that can be substituted, monocyclic heteroaryl that can be substituted, carbonyl that can be substituted, carboxyl that can be substituted, oxycarbonyl that can be substituted, carbamoyl that can be substituted, silyl that can be substituted, alkylamino that can be substituted or arylamino that can be substituted;

[0027] X1, X2, X3 are N or C-R1;

[0028] wherein each R1 is independently selected from one or more of hydrogen, deuterium, cyano, alkyl that can be substituted, cycloalkyl that can be substituted, heterocyclic group that can be substituted, alkenyl that can be substituted, cycloalkenyl that can be substituted, alkynyl that can be substituted, alkoxy that can be substituted, alkylthio that can be substituted, aryl ether group that can be substituted, aryl thioether group that can be substituted, aryl that can be substituted, monocyclic heteroaryl that can be substituted, carbonyl that can be substituted, carboxyl that can be substituted, oxycarbonyl that can be substituted, carbamoyl that can be substituted, silyl that can be substituted, alkylamino that can be substituted or arylamino that can be substituted;

[0029] In addition, the present invention provides a light-emitting element in which an organic layer exists between an anode and a cathode, and the above-mentioned fluoranthene derivative is contained in the organic layer.

[0030] In addition, the present invention also discloses a photoelectric conversion element containing the above-mentioned fluoranthene derivative.

[0031] [Effects of the Invention]

[0032] According to the present invention, an organic thin-film light-emitting element that can simultaneously achieve high luminous efficiency, low driving voltage, high durability, and a simple manufacturing process can be provided. Detailed Embodiments

[0033] The following will describe in detail the detailed embodiments of the present invention.

[0034] First, the fluoranthene derivative having the structure shown in the general formula (1) provided by the present invention will be described in detail.

[0035]

General Formula 1

[0036]

[0037] A, B, C, D, E, F, G are each independently selected from a single bond, phenyl that can be substituted or monocyclic heteroaryl that can be substituted;

[0038] At least one of A, B, C, F, and G is a monocyclic heteroaryl that can be substituted or a phenyl group substituted with a cyano group;

[0039] a, b, c, d, and e each independently selected from 0 or 1;

[0040] When F is a monocyclic heteroaryl that can be substituted or a phenyl group substituted with a cyano group, d is selected from 1;

[0041] When G is a monocyclic heteroaryl that can be substituted or a phenyl group substituted with a cyano group, e is selected from 1;

[0042] Only one of A, B, and C is ortho-substituted;

[0043] The substituents of the above-mentioned phenyl group or heteroaryl group that can be substituted are each independently selected from one or more of hydrogen, deuterium, cyano group, alkyl group that can be substituted, cycloalkyl group that can be substituted, heterocyclic group that can be substituted, alkenyl group that can be substituted, cycloalkenyl group that can be substituted, alkynyl group that can be substituted, alkoxy group that can be substituted, alkylthio group that can be substituted, aryl ether group that can be substituted, aryl thioether group that can be substituted, aryl group that can be substituted, monocyclic heteroaryl group that can be substituted, carbonyl group that can be substituted, carboxyl group that can be substituted, oxycarbonyl group that can be substituted, carbamoyl group that can be substituted, silyl group that can be substituted, alkylamino group that can be substituted, or arylamino group that can be substituted;

[0044] X1, X2, and X3 are N or C-R1;

[0045] Wherein R1 are each independently selected from one or more of hydrogen, deuterium, cyano group, alkyl group that can be substituted, cycloalkyl group that can be substituted, heterocyclic group that can be substituted, alkenyl group that can be substituted, cycloalkenyl group that can be substituted, alkynyl group that can be substituted, alkoxy group that can be substituted, alkylthio group that can be substituted, aryl ether group that can be substituted, aryl thioether group that can be substituted, aryl group that can be substituted, monocyclic heteroaryl group that can be substituted, carbonyl group that can be substituted, carboxyl group that can be substituted, oxycarbonyl group that can be substituted, carbamoyl group that can be substituted, silyl group that can be substituted, alkylamino group that can be substituted, or arylamino group that can be substituted;

[0046] Among all the above substituents, hydrogen can also be deuterium.

[0047] Moreover, in the case of "substitutable", the preferred substituents are the substitutable alkyl groups, substitutable cycloalkyl groups, substitutable heterocyclic groups, substitutable alkenyl groups, substitutable cycloalkenyl groups, substitutable alkynyl groups, substitutable alkoxy groups, substitutable alkylthio groups, substitutable aryl ether groups, substitutable aryl thioether groups, substitutable aryl groups, substitutable heteroaryl groups, substitutable carbonyl groups, substitutable carboxyl groups, substitutable oxycarbonyl groups, substitutable carbamoyl groups, substitutable silyl groups, substitutable alkylamino groups or substitutable arylamino groups, halogen, cyano, carbonyl, carboxyl, oxycarbonyl, carbamoyl, phosphinyl, condensed aromatic hydrocarbon rings, monocyclic aromatic heterocycles and condensed aromatic heterocycles, one or more of them. Additionally, the specific substituents preferably set in the description of each substituent are preferred. Moreover, these substituents may also be further substituted by the above-mentioned substituents.

[0048] In the case of "unsubstituted" in the case of "substitutable", it means being substituted by a hydrogen atom.

[0049] "Ortho substitution" refers to taking two adjacent carbons on the benzene ring of monocyclic compounds such as benzene ring and pyridine as the connection sites of substituents.

[0050] In the compounds or their partial structures described below, in the case of "substitutable", it is the same as above.

[0051] The so-called alkyl group means saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc., which may or may not have substituents. There are no particular restrictions on the additional substituents in the case of being substituted. For example, alkyl groups, aryl groups, heteroaryl groups, etc. can be cited, and this also applies to the following descriptions. Moreover, the number of carbon atoms of the alkyl group is not particularly limited. Considering the ease of obtaining materials and cost, it is preferably 1 or more and 20 or less.

[0052] The so-called cycloalkyl group means saturated aliphatic cycloalkyl groups such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may or may not have substituents. The number of carbon atoms in the alkyl part is not particularly limited. Considering the ease of obtaining materials and cost, it is preferably in the range of 3 or more and 20 or less.

[0053] The so-called alkenyl group means unsaturated aliphatic hydrocarbon groups containing double bonds such as vinyl, allyl, butadiene, etc., which may or may not have substituents. The number of carbon atoms of the alkenyl group is not particularly limited. Considering the ease of obtaining materials and cost, it is preferably in the range of 3 or more and 20 or less.

[0054] The so-called cycloalkenyl group means an unsaturated aliphatic hydrocarbon group containing a double bond such as cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, etc., which may or may not have a substituent. The carbon number of the alkenyl group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 3 or more and 20 or less is preferred.

[0055] The so-called alkynyl group means an unsaturated aliphatic hydrocarbon group containing a triple bond such as ethynyl group, etc., which may or may not have a substituent. The carbon number of the alkenyl group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 3 or more and 20 or less is preferred.

[0056] The so-called alkoxy group means a functional group of an aliphatic hydrocarbon group bonded via an ether bond such as methoxy group, ethoxy group, propoxy group, etc., and the aliphatic hydrocarbon group may or may not have a substituent. The carbon number of the alkoxy group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 1 or more and 20 or less is preferred.

[0057] The so-called alkylthio group is formed by substituting the oxygen atom of the ether bond of the alkoxy group with a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The carbon number of the alkylthio group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 1 or more and 20 or less is preferred.

[0058] The so-called aryl ether group means a functional group of an aromatic hydrocarbon group bonded via an ether bond such as phenoxy group, etc., and the aromatic hydrocarbon group may or may not have a substituent. The carbon number of the aryl ether group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 6 or more and 40 or less is preferred.

[0059] The so-called aryl thioether group is formed by substituting the oxygen atom of the ether bond of the aryl ether group with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The carbon number of the aryl thioether group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 6 or more and 40 or less is preferred.

[0060] The so-called aryl group means an aromatic hydrocarbon group such as phenyl group, naphthyl group, biphenyl group, phenanthryl group, terphenyl group, pyrenyl group, 1,2-benzacenaphthylenyl group, etc. The aryl group may or may not have a substituent. The carbon number of the aryl group is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 6 or more and 40 or less is preferred.

[0061] The so-called heteroaryl refers to a cyclic aromatic group having an atom other than carbon within one ring, such as furyl, thiophenyl, pyridyl, quinolinyl, isoquinolinyl, pyrazinyl, pyrimidinyl, etc., which may be unsubstituted or substituted. The number of carbons in the heteroaryl is not particularly limited, and from the aspects of ease of material acquisition and cost, a range of 2 or more and 6 or less is preferred.

[0062] The so-called halogen refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0063] The carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, and phosphine oxide group may or may not have a substituent. Here, examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc., and these substituents may also be further substituted.

[0064] The so-called arylene refers to a divalent or trivalent group derived from an aromatic hydrocarbon group such as phenyl, naphthyl, biphenyl, etc., which may or may not have a substituent.

[0065] Examples of the condensed aromatic hydrocarbon ring include a naphthalene ring, an azulene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a 1,2-benzophenanthrene ring, a tetracene ring, a triphenylene ring, an acenaphthene ring, a hexabenzobenzene ring, a fluorene ring, a 1,2-benzacenaphthene ring, a tetracene ring, a pentacene ring, a perylene ring, a pentaphene ring, a picene ring, a pyranthrene ring, an anthraanthrene ring, etc. In addition, the above-mentioned condensed aromatic hydrocarbon ring may also have a substituent.

[0066] Examples of the monocyclic aromatic heterocycle include a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole ring, a thiazole ring, etc. In addition, the above-mentioned monocyclic aromatic heterocycle may also have a substituent.

[0067] Examples of the condensed aromatic heterocycle include a quinoline ring, an isoquinoline ring, a quinoxaline ring, a benzimidazole ring, an indole ring, a benzimidazole ring, a benzothiazole ring, a benzoxazole ring, a quinoxaline ring, a quinazoline ring, a phthalazine ring, a carbazole ring, a carboline ring, a diazacarbazole ring (a ring in which one of the carbon atoms of the hydrocarbon ring constituting the carboline ring is further substituted by a nitrogen atom), etc. In addition, the above-mentioned condensed aromatic heterocycle may also have a substituent.

[0068] The present invention provides a fluoranthene derivative composed of a nitrogen-containing benzene system main body, and the structure of fluoranthene is three benzene rings around a cyclopentane, and electrons can be delocalized in the whole fluoranthene structure, and on the other hand, the cyclopentane part forms an electron hole part, and the tendency of electron absorption is generated. The nitrogen-containing benzene system main body can be benzene or the nitrogen-containing benzene of multiple nitrogens, and the large π bond of benzene itself in the nitrogen-containing benzene system can move in the molecular global domain, and when nitrogen is increased in the nitrogen-containing benzene system main body, the lone pair of electrons of nitrogen can further increase the delocalized electrons in the large π bond, so as to strengthen the transmission capacity of electrons. Meanwhile, ortho-phenylene can improve the orientation of molecule in addition to allowing the nitrogen-containing benzene system main body to be close to the fluoranthene main body, and further improve efficiency. But it is worth noting that when two ortho-phenylenes are connected, the electron flow in the molecule will be disturbed, and the electron transmission capacity of the molecule will be reduced instead.

[0069] On the other hand, since the electron control ability of heteroatoms in condensed ring heterocycles such as dibenzothiophene, dibenzofuran, carbazole, etc. is affected by the dispersion effect of the condensed rings, thereby reducing the electron transmission ability, the heteroatom compounds provided by the present invention are generally monocyclic heteroaromatic compounds.

[0070] In the disclosed compositions of fluoranthene and azobenzene-based hosts, these compounds need to be used in combination with alkali metal releasers such as Liq to function as the host, and some of these host compounds will have problems with insufficient or excessive release of the alkali metal releaser when used in combination with the alkali metal releaser. After research, it was found that relying solely on the heteroatom of a nitrogen-based host is insufficient to capture alkali metals, and the resulting complex is not stable enough. Under harsh conditions such as vacuum high-temperature evaporation, there will be problems with unstable performance after film formation. By increasing the number of sites containing heteroatoms in the molecule, the bond between the molecule and the metal is strengthened, so that a more stable complex can be obtained, thereby achieving more stable film-forming characteristics and reducing process difficulty.

[0071] When the number of benzene rings connecting fluoranthene and azobenzene is too small, the mobility of the molecule is reduced, the transmission capacity of the electron is reduced, and the molecular weight may be too small to reduce the glass transition temperature. On the other hand, when the number of benzene rings is too large, the distance between fluoranthene and azobenzene is too far, the electron cannot move within the molecule, and the transmission capacity of the electron is also reduced. At the same time, the sublimation temperature is also increased. If the sublimation temperature is too high (generally higher than 380 degrees), it is impossible to evaporate, and it is impossible to make an OLED panel. Therefore, it is preferred that at least two of a, b, and c are selected from 1.

[0072] Through experiments, it was found that when two of a, b, and c are selected from 1 and the other one is selected from 0, the distance between fluoranthene and the nitrogen-containing benzene host is closer, the electron transfer is faster, and the device shows higher efficiency.

[0073] When a = b = c = 1, more benzene rings increase the mobility and result in a lower voltage in the device.

[0074] Considering the energy levels of common electron injection layers and hole blocking layers, as well as the actual test results, good electron transport performance can be achieved when at least two of X1, X2, and X3 are N.

[0075] In particular, when two of X1, X2, and X3 are N, the compatibility with the electron injection layer is better, leading to better efficiency.

[0076] In particular, when three of X1, X2, and X3 are N, the compatibility with the hole blocking layer is better, resulting in a longer lifespan.

[0077] When a heterocycle containing a heteroatom or a benzene ring with a hetero substituent is introduced into the center of fluoranthene and the nitrogen-containing host, the heteroatom can provide additional electrons and enhance the electron transport ability. Non-fused ring groups such as pyridyl and cyanophenyl have better effects on enhancing electron transport ability because the electrons are not dispersed by the fused rings. Therefore, it is preferred that at least one of A, B, and C is selected from pyridyl or cyanophenyl.

[0078] When a heterocycle containing a heteroatom or a benzene ring with a hetero substituent is introduced at the outermost edge of the nitrogen-containing host, the increased heteroatom center strengthens the coordination ability with the metal during metal coordination, thereby reducing the response sensitivity of electron release during metal doping and improving the process window. Non-fused ring groups such as pyridyl and cyanophenyl have better coordination ability because the electrons are not dispersed by the fused rings. Therefore, it is preferred that at least one of F and G is selected from pyridyl or cyanophenyl.

[0079] Through practice, we believe that the following molecular structures and their derivative structures can achieve excellent comprehensive performance in terms of efficiency, voltage, and lifespan depending on the specific device structure and device application. Therefore, the following compounds are preferred:

[0080]

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[0100]

[0101] The present invention also discloses a light-emitting element, which has an organic layer between an anode and a cathode; the organic layer is a layer responsible for light emission and / or a layer responsible for processing electrons or holes, and the above-mentioned fluoranthene derivative is contained in the organic layer.

[0102] Considering that a large number of electrons can be contained in this material and it has the ability to process electrons. At the same time, holes are naturally generated after losing electrons, so it can also process holes. Preferably, the organic layer is a layer responsible for processing electrons or holes, and the above-mentioned fluoranthene derivative is contained in the organic layer.

[0103] Considering the electron transport ability of this material, preferably, the organic layer has an electron transport layer, and the above-mentioned fluoranthene derivative is contained in the electron transport layer.

[0104] Considering a large number of electrons in this material that exceed the binding ability of the atomic nucleus, preferably, the organic layer has an electron generation layer, and the above-mentioned fluoranthene derivative is contained in the electron generation layer.

[0105] Considering that a large number of electrons are contained in this material, which can thus prevent the movement of holes, preferably, the organic layer has a hole blocking layer, and the above-mentioned fluoranthene derivative is contained in the hole blocking layer.

[0106] In addition, the present invention also discloses a photoelectric conversion element containing the above-mentioned fluoranthene derivative.

[0107] In the synthesis of the fluoranthene derivative of the present invention, known methods can be used. As a method for introducing a pyridine-based host into the fluoranthene derivative skeleton, for example, a coupling reaction method using a substituted or unsubstituted halogenated fluoranthene host and a substituted or unsubstituted pyridine-based host under a palladium catalyst or a nickel catalyst can be cited, but it is not limited to these methods. In addition, when introducing a pyridine-based host into the fluoranthene derivative via an arylene or heteroarylene, a substituted arylboronic acid or heteroarylboronic acid is used as the pyridine-based host, or a fluoranthene host substituted with a halogenated aryl can also be used. Moreover, a borate ester can also be used instead of the above various boronic acids.

[0108] The fluoranthene derivative of the present invention is preferably used as an electron transport material and an electron generation material. Here, the so-called electron transport material and electron generation material refer to materials used in any layer of a light-emitting element. As described later, in addition to materials used in layers selected from a hole transport layer, a light-emitting layer, and an electron transport layer, it also includes materials used in a protective film of a cathode. By using the fluoranthene derivative of the present invention in any layer of a light-emitting element, a light-emitting element with high luminous efficiency, low driving voltage, and high durability can be obtained.

[0109] Next, an embodiment of the light-emitting element of the present invention will be described in detail. The light-emitting element of the present invention includes an anode and a cathode, and an organic layer inserted between these anode and cathode. The organic layer includes at least a light-emitting layer and an electron transport layer, and the light-emitting layer emits light using electric energy.

[0110] In addition to the structure that only includes a light-emitting layer / electron transport layer, the organic layer can also include: 1) a hole transport layer / light-emitting layer / electron transport layer and 2) a hole transport layer / light-emitting layer / electron transport layer / electron injection layer, 3) a hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer, etc. Moreover, each of the above layers can be a single layer or a multi-layer connected by an electron generation layer and a hole generation layer.

[0111] The fluoranthene derivative of the present invention can be used in any layer in the above element structure, but has high electron injection and transport ability, fluorescence quantum yield, and film stability. Therefore, it is preferably used in an electron transport layer and an electron generation layer.

[0112] In the light-emitting element of the present invention, the anode and the cathode have the function of supplying sufficient current for the element to emit light. In order to make the light exit, at least one of them is preferably transparent or semi-transparent. According to actual applications and device designs, a transparent anode or a transparent cathode can be used.

[0113] The material used in the anode, if it is a material that can inject holes efficiently into the organic layer and is transparent or semi-transparent for light emission, is not particularly limited to conductive metal oxides such as tin oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc., or metals such as gold, silver, chromium, inorganic conductive substances such as copper iodide, copper sulfide, conductive polymers such as polythiophene, polypyrrole, polyaniline, etc. Particularly preferably, ITO glass or Nesa glass is used. These electrode materials can be used alone, or multiple materials can be laminated or mixed. The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the device. From the perspective of power consumption of the device, a low resistance is preferred. For example, an ITO substrate with a resistance of 300 Ω / square or less can function as an element electrode, but now substrates with a resistance of about 10 Ω / square can also be supplied. Therefore, it is particularly preferred to use a low-resistance substrate with a resistance of 20 Ω / square or less. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 100 nm to 300 nm in many cases.

[0114] Moreover, in order to maintain the mechanical strength of the light-emitting device, it is preferred to form the light-emitting device on a substrate. As the substrate, a glass substrate such as soda glass or non-alkali glass can be suitably used, or a flexible substrate with a high polymer content can also be used. The thickness of the substrate only needs to be a thickness that can sufficiently maintain the mechanical strength, so a thickness of 0.5 mm or more is sufficient. Regarding the material of the glass, it is preferably a material with fewer eluted ions from the glass, so non-alkali glass is preferred. Alternatively, soda-lime glass with a barrier coat such as SiO2 is also commercially available, so this soda-lime glass can also be used. In addition, if the first electrode can function stably, for example, an anode can also be formed on a polyimide substrate. The ITO film formation method is not particularly limited, such as the electron beam method, sputtering method, and chemical reaction method.

[0115] The material used in the cathode, if it is a material that can inject electrons efficiently into the light-emitting layer, is not particularly limited. Generally, metals such as platinum, gold, silver, copper, iron, tin, aluminum, indium, etc. are preferred, or alloys or multi-layer laminates of these metals with low work function metals such as lithium, sodium, potassium, calcium, magnesium, etc. Among them, considering the resistance value, film formation ease, film stability, light-emitting efficiency, etc., the main component is preferably aluminum, silver, or magnesium. In particular, if it is composed of magnesium and silver, the electron injection into the electron transport layer and electron injection layer in the present invention becomes easier, and low-voltage driving can be achieved, so it is preferred.

[0116] In addition, in order to protect the cathode, the following methods can be cited as preferred examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride, and organic polymer compounds such as polyvinyl alcohol, polyvinyl chloride, and hydrocarbon-based polymer compounds are laminated on the cathode as a protective film layer. Moreover, the fluoranthene derivative of the present invention can also be used as the protective film layer. However, in the case of an element structure (top-emitting structure) in which light is emitted from the cathode side, the protective film layer can be selected from materials having translucency in the visible light region. The production methods of these electrodes include resistance heating, electron beam, sputtering, ion plating, coating, etc., and there is no particular limitation. In order to further improve the light extraction efficiency and thus reduce the reduction in the light emission efficiency caused by the insufficient transparency of the transparent cathode, an organic material with a high refractive index can also be used. On top of this, a metal (such as LiF) or a low refractive index organic compound can also be used for optical adjustment and then a thin film encapsulation (TFE) layer is added for flexible protection to achieve flexibility or even foldability while protecting the device from the influence of water and oxygen. The specific structure is not limited.

[0117] The hole transport layer can be formed by the following methods: a method of laminating or mixing one or more hole transport materials, or a method of using a mixture of a hole transport material and a polymer binder. Moreover, the hole transport material must efficiently transport holes from the positive electrode between the electrodes to which an electric field is applied, and preferably has a high hole injection efficiency and efficiently transports the injected holes. Therefore, it is required to have an appropriate ionization potential, a large hole mobility, excellent stability, and a substance that is difficult to generate impurities that become traps during manufacturing and use. There is no particular limitation on the substance that satisfies such conditions. For example, preferably, 4,4′-bis(N-(3-methylphenyl)-N-phenylamino)biphenyl (TPD), 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPD), 4,4′-bis(N,N-bis(4-biphenylyl)amino)biphenyl (TBDB), bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenyl (TPD232) and other benzidine derivatives, materials groups such as 4,4′,4″-tris(3-methylphenyl(phenyl)amino)triphenylamine (m-MTDATA), 4,4′,4″-tris(1-naphthyl(phenyl)amino)triphenylamine (1-TNATA) and other materials called starburst arylamines, materials having a carbazole skeleton (wherein carbazole polymers, specifically derivatives of carbazole dimers such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), derivatives of carbazole trimers, derivatives of carbazole tetramers), triphenylene compounds, pyrazoline derivatives, stilbene-based compounds, hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives and other heterocyclic compounds, fullerene derivatives, polycarbonates or styrene derivatives having the above monomers in the side chain in the polymer system, polythiophene, polyaniline, polyfluorene, polyvinylcarbazole and polysilane. In addition, inorganic compounds such as p-type Si and p-type SiC can also be used.

[0118] The hole mobility of the fluoranthene derivative of the present invention is large, and the electrochemical stability is excellent. Therefore, it can also be used as a hole transport material. The fluoranthene derivative of the present invention can also be used as a hole injection material, but because of its high hole mobility, it can be suitably used as a hole transport material.

[0119] The fluoranthene derivative of the present invention has excellent electron injection and transport characteristics. Therefore, when it is used in the electron transport layer, there is a concern that electrons no longer recombine in the light-emitting layer and partially leak into the hole transport layer. Therefore, it is preferable to use a compound with excellent electron blocking properties in the hole transport layer. Among them, a compound containing a carbazole skeleton has excellent electron blocking properties and can contribute to the high efficiency of the light-emitting element, so it is preferable. In addition, the above-mentioned compound containing a carbazole skeleton preferably contains a carbazole dimer, a carbazole trimer, or a carbazole tetramer skeleton. The reason is that these compounds have both good electron blocking properties and hole injection and transport characteristics. In addition, when a compound containing a carbazole skeleton is used in the hole transport layer, it is more preferable that the combined light-emitting layer contains a phosphorescent light-emitting material described later. The reason is that the compound having the above-mentioned carbazole skeleton also has a high triplet exciton blocking function, and high luminous efficiency can be achieved when combined with a phosphorescent light-emitting material. Moreover, if a compound containing a triphenylene skeleton, which is excellent in terms of having a high hole mobility, is used in the hole transport layer, effects such as improved carrier balance, improved luminous efficiency, and improved durability life can be obtained, so it is preferable. If the compound containing a triphenylene skeleton has two or more diarylamino groups, it is more preferable. The above-mentioned compound containing a carbazole skeleton or a compound containing a triphenylene skeleton can be used alone as the hole transport layer or can be used by mixing them with each other. Moreover, other materials can also be mixed within the range that does not impair the effects of the present invention. Moreover, when the hole transport layer is composed of multiple layers, it is sufficient that any one layer contains a compound containing a carbazole skeleton or a compound containing a triphenylene skeleton.

[0120] A hole injection layer may also be provided between the anode and the hole transport layer. By providing the hole injection layer, the driving voltage of the light-emitting element is reduced and the durability life is also improved. In the hole injection layer, a material having an ionization potential smaller than that of the material generally used in the hole transport layer may be preferably used. Specifically, in addition to the above-listed benzidine derivatives such as TPD232 and the starburst arylamine material group, phthalocyanine derivatives and the like may also be used. Moreover, it is also preferable that the hole injection layer is composed of a receptor compound alone, or the receptor compound is doped in other hole transport materials and used. Examples of the receptor compound may include metal chlorides such as iron(III) chloride, 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). Moreover, organic compounds having a nitro group, a cyano group, a halogen, or a trifluoromethyl group in the molecule, quinone compounds, acid anhydride compounds, fullerenes, etc. may also be suitably used. Specific examples of these compounds may include hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyano-p-benzoquinodimethane (TCNQ), tetrafluoro-tetracyano-p-benzoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN6), p-fluoranil, p-chloranil, p-bromanil, p-benzoquinone, 2,6-dichlorobenzoquinone, 2,5-dichlorobenzoquinone, tetramethylbenzoquinone, 1,2,4,5-tetracyano benzene, o-dicyanobenzene, p-dicyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-dichloro-5,6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, p-cyanonitrobenzene, m-cyanonitrobenzene, o-cyanonitrobenzene, 1,4-naphthoquinone, 2,3-dichloronaphthoquinone, 1-nitronaphthalene, 2-nitronaphthalene, 1,3-dinitronaphthalene, 1,5-dinitronaphthalene, 9-cyanoanthracene, 9-nitroanthracene, 9,10-anthraquinone, 1,3,6,8-tetranitrocarbazole, 2,4,7-trinitro-9-fluorenone, 2,3,5,6-tetracyano pyridine, maleic anhydride, phthalic anhydride, C60, or C70, etc.

[0121] Among these compounds, metal oxides or cyanide group-containing compounds are easy to handle and also easy to vapor-deposit, so the above effects can be easily obtained, and thus they are preferred. Examples of preferred metal oxides include molybdenum oxide, vanadium oxide, or ruthenium oxide. Among cyanide group-containing compounds, (a) compounds having at least one electron-accepting nitrogen atom in the molecule in addition to the nitrogen atom of the cyanide group, (b) compounds having both a halogen and a cyanide group in the molecule, (c) compounds having both a carbonyl group and a cyanide group in the molecule, or (d) compounds having both a halogen and a cyanide group in the molecule and having at least one electron-accepting nitrogen atom in addition to the nitrogen atom of the cyanide group are strong electron acceptors, and thus are more preferred. Specific examples of such compounds are as described below.

[0122]

[0123]

[0124] In any case where the hole injection layer is composed of a receptor compound alone or where a receptor compound is doped in the hole injection layer, the hole injection layer can be a single layer or multiple layers can be stacked. Moreover, in the case of doping a receptor compound, from the viewpoint of being able to alleviate the barrier for injecting holes into the hole transport layer, the hole injection material used in combination is more preferably the same compound as the compound used in the hole transport layer.

[0125] The light-emitting layer can be either a single layer or multiple layers, and is formed by a light-emitting material (host material, dopant material) respectively. It can be a mixture of a host material and a dopant material, or can be a host material alone, and can be arbitrary. That is, in the light-emitting element of the present invention, in each light-emitting layer, it can be that only the host material or the dopant material emits light, or both the host material and the dopant material can emit light. From the viewpoint of efficiently using electric energy and obtaining light emission with high color purity, it is preferred that the light-emitting layer contains a mixture of a host material and a dopant material. Moreover, the host material and the dopant material can each be one kind or a combination of multiple kinds, and can be arbitrary. The dopant material can be contained in the whole of the host material or can be partially contained, and can be arbitrary. The dopant materials can be stacked or dispersed, and can be arbitrary. The dopant material can control the emission color. If the amount of the dopant material is too large, a concentration quenching phenomenon will occur, so it is preferred to use it at 20% by weight or less relative to the host material, and more preferably 10% by weight or less. As a doping method, it can be formed by co-evaporation with the host material, or can be evaporated simultaneously after being premixed with the host material.

[0126] As the luminescent material, condensed ring derivatives such as anthracene or pyrene which have been known as luminescent substances since before, metal chelated oxinoid compounds such as tris(8-hydroxyquinoline)aluminum, bisstyryl derivatives such as bisstyryl anthracene derivatives or stilbenylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, polyphenylacetylene derivatives, poly(phenylene) derivatives, and polythiophene derivatives in the polymer system can be used, but there is no particular limitation.

[0127] The host material contained in the luminescent material is not particularly limited, and compounds or their derivatives having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, tetracene, triphenylene, perylene, 1,2-benzacenaphthene, fluorene, indene, etc., aromatic amine derivatives such as N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, metal chelate oxine compounds such as tris(8-hydroxyquinoline) aluminum(III), bisstyryl derivatives such as stilbenylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, pyrrolopyrrole derivatives, thiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, triazine derivatives, polyphenylacetylene derivatives, poly(p-phenylene) derivatives, polyfluorene derivatives, poly(vinylcarbazole) derivatives, polythiophene derivatives, etc. in the polymer system are not particularly limited. Further, the doping material is not particularly limited, and compounds or their derivatives having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, triphenylene, perylene, 1,2-benzacenaphthene, fluorene, indene, etc. (for example, 2-(benzothiazol-2-yl)-9,10-diphenylanthracene or 5,6,11,12-tetraphenyltetracene, etc.), compounds or their derivatives having a heteroaryl ring such as furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene, etc., borane derivatives, stilbenylbenzene derivatives, aminostyryl derivatives such as 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, 4,4'-bis(N-(stilbene-4-yl)-N-phenylamino)stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, azomethine derivatives, pyrromethene derivatives, diketopyrrolo[3,4-c]pyrrole derivatives, coumarin derivatives such as 2,3,5,6-1H,4H-tetrahydro-9-(2'-benzothiazolyl)quinazino[9,9a,1-gh]coumarin, imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and other azole derivatives and their metal complexes, and aromatic amine derivatives represented by N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, etc.

[0128] In addition, a phosphorescent light-emitting material is also included in the light-emitting layer. The so-called phosphorescent light-emitting material is a material that exhibits phosphorescent emission even at room temperature. When a phosphorescent light-emitting material is used as a dopant, it is basically required to obtain phosphorescent emission even at room temperature, and there is no particular limitation. Preferably, it is an organometallic complex compound containing at least one metal selected from the group consisting of iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re). Among them, from the viewpoint of having a high phosphorescent emission yield even at room temperature, an organometallic complex having iridium or platinum is more preferable. As a host used in combination with a phosphorescent dopant, an indole derivative, a carbazole derivative, an indolocarbazole derivative, a nitrogen-containing aromatic compound derivative having a pyridine, pyrimidine, or triazine skeleton, a polyarylbenzene derivative, a spirofluorene derivative, a truxene derivative, a triphenylene derivative, etc., an aromatic hydrocarbon compound derivative, a chalcogen-containing compound such as a dibenzofuran derivative or a dibenzothiophene derivative, an organometallic complex such as a beryllium hydroxyquinoline complex, etc. can be suitably used. If it has a larger triplet energy than the dopant basically used and electrons and holes are smoothly injected and transported from their respective transport layers, it is not limited to these compounds. Moreover, two or more triplet light-emitting dopants may be contained, and two or more host materials may be contained. In addition, one or more triplet light-emitting dopants and one or more fluorescent light-emitting dopants may be contained.

[0129] As a preferable phosphorescent host or dopant, there is no particular limitation, and specific examples are shown below.

[0130]

[0131]

[0132] In the present invention, the so-called electron transport layer is a layer that injects electrons from the cathode and further transports the electrons. The electron transport layer desirably has a high electron injection efficiency and efficiently transports the injected electrons. Therefore, the electron transport layer is preferably composed of a material having the following properties: a large electron affinity, a large electron mobility, and excellent stability, and it is difficult to generate impurities that become traps during manufacturing and use. However, when considering the transport balance of holes and electrons, if the electron transport layer mainly functions to efficiently prevent holes from the anode from recombining and flowing to the cathode side, even if it is composed of a material with not so high electron transport ability, the effect of improving the light emission efficiency becomes the same as that composed of a material with high electron transport ability. Therefore, the electron transport layer in the present invention also includes the same meaning as a hole blocking layer that can efficiently prevent hole migration.

[0133] Examples of the electron transport material used in the electron transport layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, quinone derivatives such as anthraquinone or p-benzoquinone, phosphorus oxide derivatives, various metal complexes such as tris(8-hydroxyquinoline)aluminum(III), benzo-hydroxyquinoline complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. Considering reducing the driving voltage and obtaining high efficiency light emission, it is preferable to use a compound having a heteroaryl ring structure, which is composed of elements selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus and contains electron-accepting nitrogen.

[0134] An aromatic heterocycle containing electron-accepting nitrogen has a high electron affinity. An electron transport material having electron-accepting nitrogen easily accepts electrons from a cathode having a high electron affinity, enabling driving at a lower voltage. Moreover, the supply of electrons to the light-emitting layer increases and the recombination probability becomes higher, thus improving the light emission efficiency.

[0135] Examples of the heteroaryl ring containing electron-accepting nitrogen include a pyridine ring, a pyrazine ring, a pyrimidine ring, a quinoline ring, a quinoxaline ring, a naphthyridine ring, a pyrimidinepyrimidine ring, a benzoquinoline ring, a phenanthroline ring, an imidazole ring, an oxazole ring, an oxadiazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthroimidazole ring.

[0136] Examples of the compounds having these heteroaryl 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, oligopyridine derivatives such as bipyridine or terpyridine, quinoxaline derivatives, naphthyridine derivatives, etc. as preferred compounds. Among them, from the viewpoint of electron transport ability, imidazole derivatives such as tris(N-phenylbenzimidazol-2-yl)benzene, oxadiazole derivatives such as 1,3-bis[(4-tert-butylphenyl)-1,3,4-oxadiazolyl]benzene, triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine or 1,3-bis(1,10-phenanthrolin-9-yl)benzene, benzoquinoline derivatives such as 2,2′-bis(benzo[h]quinolin-2-yl)-9,9′-spirobifluorene, bipyridine derivatives such as 2,5-bis(6′-(2′,2″-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, terpyridine derivatives such as 1,3-bis(4′-(2,2′:6′,2″-terpyridyl))benzene, naphthyridine derivatives such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide can be preferably used. Moreover, if these derivatives have a condensed polycyclic aromatic skeleton, the glass transition temperature is increased, the electron mobility is also increased, and the effect of lowering the voltage of the light-emitting element is great, so they are more preferred. In addition, considering the improvement of the element durability, the ease of synthesis, and the easy availability of raw materials, the condensed polycyclic aromatic skeleton is particularly preferably an anthracene skeleton, a pyrene skeleton, or a phenanthroline skeleton. The above electron transport materials can be used alone, or two or more of the above electron transport materials can be mixed and used, or one or more of other electron transport materials can be mixed in the above electron transport materials for use. The fluoranthene derivative of the present invention also has a high electron injection and transport ability, so it can be suitably used as an electron transport material.

[0137] When using the fluoranthene derivative of the present invention, it is not necessary to limit it to one kind of each. A plurality of fluoranthene compounds of the present invention can also be mixed and used, or one or more of other electron transport materials can be mixed with the fluoranthene compounds of the present invention within the range not impairing the effects of the present invention. The electron transport materials that can be mixed are not particularly limited, and examples include compounds or their derivatives having condensed aryl rings such as naphthalene, anthracene, and pyrene, styryl-based aromatic ring derivatives represented by 4,4′-bis(diphenylethenyl)biphenyl, perylene derivatives, violanthrone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, quinone derivatives such as anthraquinone or p-benzoquinone, phosphine oxide derivatives, carbazole derivatives, indole derivatives, hydroxyquinoline complexes such as tris(8-hydroxyquinoline)aluminum(III) or hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes.

[0138] The above-mentioned electron transport material can be used alone, but two or more of the above-mentioned electron transport materials can also be used in combination, or one or more of other electron transport materials can be mixed into the above-mentioned electron transport material for use. Moreover, a donor material may also be contained. Here, the so-called donor material is a compound that improves the electron injection barrier, makes the electron injection from the cathode or the electron injection layer to the electron transport layer easier, and further improves the conductivity of the electron transport layer.

[0139] Preferred examples of the donor material in 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, or complexes of alkaline earth metals and organic substances. Preferred types of alkali metals and alkaline earth metals include alkali metals such as lithium, sodium, cesium, etc. and alkaline earth metals such as magnesium, calcium, etc., which have a low work function and a large effect of improving the electron transport ability.

[0140] The appropriate doping concentration varies depending on the material or the film thickness of the doped region. For example, when the donor material is an inorganic material such as an alkali metal or an alkaline earth metal, it is preferable to co-evaporate to form an electron transport layer such that the evaporation rate ratio of the electron transport material to the donor material is in the range of 10,000:1 to 2:1. The evaporation rate ratio is more preferably 100:1 to 5:1, and even more preferably 100:1 to 10:1. Moreover, when the donor material is a complex of a metal and an organic substance, it is preferable to co-evaporate to form an electron transport layer such that the evaporation rate ratio of the electron transport material to the donor material is in the range of 100:1 to 1:100. The evaporation rate ratio is more preferably 10:1 to 1:10, and even more preferably 7:3 to 3:7.

[0141] Moreover, an electron transport layer doped with a donor material in the fluoranthene derivative of the present invention as described above can be used as a charge generation layer in a tandem structure element that connects a plurality of light-emitting elements.

[0142] The method of doping a donor material in the electron transport layer to improve the electron transport ability particularly exerts an effect when the film thickness of the thin film layer is relatively thick. It can be particularly preferably used when the total film thickness of the electron transport layer and the light-emitting layer is 50 nm or more. For example, there is a method of utilizing the interference effect to improve the light emission efficiency, which is a method of aligning the phase of the light directly emitted from the light-emitting layer and the light reflected by the cathode to improve the light extraction efficiency. The optimal conditions vary depending on the emission wavelength of the light. When the total film thickness of the electron transport layer and the light-emitting layer becomes 50 nm or more and the emission is of a long wavelength such as red, there are cases where the film thickness approaches 100 nm.

[0143] The film thickness of the doped electron transport layer can be arbitrary for a part or all of the electron transport layer. In the case of doping a part, it is desirable to provide a doped region at least at the electron transport layer / cathode interface. Even if doping is performed only near the cathode interface, the effect of reducing the voltage can be obtained. On the other hand, if the donor material is directly in contact with the light-emitting layer, there is a case where an adverse effect of reducing the light-emitting efficiency occurs. In this case, it is preferable to provide an undoped region at the light-emitting layer / electron transport layer interface.

[0144] In the present invention, an electron injection layer can also be provided between the cathode and the electron transport layer. Generally, the electron injection layer is inserted for the purpose of facilitating electron injection from the cathode into the electron transport layer. In the case of insertion, a compound having a heteroaryl ring structure containing an electron-accepting nitrogen can be used, or a layer containing the above donor material can also be used. The electron injection layer can also contain the fluoranthene derivative of the present invention. Moreover, an insulator or a semiconductor inorganic substance, or a metal can also be used in the electron injection layer. By using these materials, short circuits of the light-emitting element can be effectively prevented, and the electron injection property can be improved, so it is preferable. Such an insulator is preferably at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is more preferable in terms of further improving the electron injection property. Specifically, preferred alkali metal chalcogenides include, for example, Li2O, Na2S, and Na2Se, and preferred alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, BeO, BaS, and CaSe. Moreover, preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl. Moreover, preferred alkaline earth metal halides include, for example, fluorides such as CaF2, BaF2, SrF2, MgF2, and BeF2 or halides other than fluorides. A complex of an organic substance and a metal can also be suitably used. When a complex of an organic substance and a metal is used in the electron injection layer, it is easier to adjust the film thickness, so it is more preferable. As an example of such an organometallic complex, preferred examples of the organic substance in the complex with the organic substance include hydroxyquinoline, benzo-hydroxyquinoline, pyridylphenol, flavonol, hydroxyimidazopyridine, hydroxyindole, and hydroxytriazole. In addition, a metal can also be used, for example, Li, Yb, Ba, etc.

[0145] The formation method of each of the above layers constituting the light-emitting element is not particularly limited, such as resistance heating evaporation, electron beam evaporation, sputtering, molecular layer deposition method, coating method, etc. Generally, from the aspect of element characteristics, resistance heating evaporation or electron beam evaporation is preferable.

[0146] The thickness of the organic layer is determined by the resistance value of the light-emitting substance and thus cannot be defined. Preferably, it is 1 nm to 1000 nm. The film thicknesses of the light-emitting layer, the electron transport layer, and the hole transport layer are preferably 1 nm or more and 200 nm or less, and more preferably 5 nm or more and 100 nm or less.

[0147] The light-emitting element of the present invention has a function of converting electric energy into light. Here, direct current is mainly used for the electric energy, and pulse current or alternating current may also be used. The current value and the voltage value are not particularly limited. Considering the power consumption or the life of the element, they should be selected in such a way that the maximum brightness is obtained with as low energy as possible.

[0148] The light-emitting element of the present invention can also preferably be used as a backlight for various devices and the like. The backlight is mainly used to improve the visibility of a display device that does not emit light itself and is used in liquid crystal display devices, clocks, audio devices, automotive panels, display boards, signs, and the like. In particular, the light-emitting element of the present invention is preferably used in the backlight of a liquid crystal display device (especially for personal computer applications where thinness has been studied), and a thinner and lighter backlight than the existing backlights can be provided.

[0149] [Examples]

[0150] Hereinafter, the present invention will be described by way of examples, but the present invention is not limited to these examples.

[0151] The materials used in the examples and comparative examples are as follows:

[0152] Toluene, xylene, methanol, etc. were purchased from Sinopharm Chemical Reagent Co., Ltd.; triazine compounds were purchased from TCI; fluoranthene compounds were purchased from Alfa Aesar; various catalysts, etc. were purchased from Aldrich.

[0153] Synthesis Example 1

[0154] Synthesis of Compound [3]

[0155]

[0156] 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. After heating to 120° and reacting for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness, washed 3 times with 100 ml of water, and recrystallized with 50 ml of o-xylene to obtain 3.5 g of white solid 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine.

[0157] Add 3.5 g of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, 1.8 g of 2-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 5.0 g of 2-(2-(4-chloro-2-cyano)phenyl)-4,6-diphenyl-1,3,5-triazine.

[0158] Add 5.0 g of 2-(2-(4-chloro-2-cyano)phenyl)-4,6-diphenyl-1,3,5-triazine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 4.13 g (purity 99.9%) of the yellow solid compound [3].

[0159] Synthesis Example 2

[0160] Synthesis of Compound [4]

[0161]

[0162] Add 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.5 g of white solid 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine.

[0163] Add 3.5 g of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, 1.8 g of 4-chloro-2-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 5.8 g of 2-(4-chloro-2-pyridyl)-4,6-diphenyl-1,3,5-triazine.

[0164] 5.8 g of 2-(4-chloro-2-pyridyl)-4,6-diphenyl-1,3,5-triazine, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized twice from 100 ml of o-xylene to obtain 4.00 g of a yellow solid compound [4] (purity 99.9%).

[0165] Synthesis Example 3

[0166] Synthesis of Compound [9]

[0167]

[0168] 2.67 g of 2-chloro-4,6-diphenyl-1,3-pyrimidine, 1.22 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.5 g of 2-(2-chlorophenyl)-4,6-diphenyl-1,3-pyrimidine as a white solid.

[0169] 3.5 g of 2-(2-chlorophenyl)-4,6-diphenyl-1,3-pyrimidine, 1.8 g of 2-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized from 100 ml of o-xylene to obtain 4.9 g of 2-(2-(4-chloro-2-cyano)phenyl)-4,6-diphenyl-1,3-pyrimidine.

[0170] 4.9 g of 2-(2-(4-chloro-2-cyano)phenyl)-4,6-diphenyl-1,3-pyrimidine, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized twice from 100 ml of o-xylene to obtain 4.10 g of a yellow solid compound [9] (purity 99.9%).

[0171] Synthesis Example 4

[0172] Synthesis of Compound

[10]

[0173]

[0174] Add 2.67 g of 2-chloro-4,6-diphenyl-1,3-pyrimidine, 1.22 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water three times, and recrystallize with 50 ml of o-xylene to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4,6-diphenyl-1,3-pyrimidine.

[0175] Add 3.4 g of 2-(2-chlorophenyl)-4,6-diphenyl-1,3-pyrimidine, 1.8 g of 4-chloro-2-pyridylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water and 100 ml of methanol three times respectively, and recrystallize with 100 ml of o-xylene to obtain 5.8 g of 2-(4-chloro-2-pyridyl)-4,6-diphenyl-1,3-pyrimidine.

[0176] Add 5.8 g of 2-(4-chloro-2-pyridyl)-4,6-diphenyl-1,3-pyrimidine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water and 100 ml of methanol three times respectively, and recrystallize with 100 ml of o-xylene twice to obtain 4.20 g (purity 99.9%) of yellow solid compound

[10] .

[0177] Synthesis Example 5

[0178] Synthesis of Compound

[15]

[0179]

[0180] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water three times, and recrystallize with 50 ml of o-xylene to obtain 3.6 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0181] Add 3.6 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 2-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 5.1 g of 2-(2-(4-chloro-2-cyano)phenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0182] Add 5.1 g of 2-(2-(4-chloro-2-cyano)phenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 4.20 g (purity 99.9%) of the yellow solid compound

[15] .

[0183] Synthesis Example 6

[0184] Synthesis of Compound

[16]

[0185]

[0186] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.6 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0187] Add 3.6 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 4-chloro-2-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 5.8 g of 2-(4-chloro-2-pyridyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0188] 5.8 g of 2-(4-chloro-2-pyridyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated, and it was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 3.12 g of a yellow solid compound

[16] (purity 99.9%).

[0189] Synthesis Example 7

[0190] Synthesis of Compound

[27]

[0191]

[0192] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated, and it was washed three times with 100 ml of water to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine by recrystallization with 50 ml of o-xylene.

[0193] 3.4 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 2-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated, and it was washed three times with 100 ml of water and 100 ml of methanol respectively to obtain 5.1 g of 2-(2-(4-chloro-2-cyano)phenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine by recrystallization with 100 ml of o-xylene.

[0194] 5.1 g of 2-(2-(4-chloro-2-cyano)phenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated, and it was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 4.10 g of a yellow solid compound

[27] (purity 99.9%).

[0195] Synthesis Example 8

[0196] Synthesis of Compound

[28]

[0197]

[0198] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After displacing the air with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated, washed three times with 100 ml of water, and recrystallized with 50 ml of o-xylene to obtain 3.6 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0199] 3.6 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 4-chloro-2-pyridylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After displacing the air with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized with 100 ml of o-xylene to obtain 5.5 g of 2-(4-chloro-2-pyridyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0200] 5.5 g of 2-(4-chloro-2-pyridyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After displacing the air with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 4.20 g (purity 99.9%) of yellow solid compound

[28] .

[0201] Synthesis Example 9

[0202] Synthesis of Compound

[31]

[0203]

[0204] 2.67 g of 2-chloro-4-phenyl-6-(4-4-pyridinyl-phenyl)-1,3-pyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After displacing the air with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated, washed three times with 100 ml of water, and recrystallized with 50 ml of o-xylene to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-(4-4-pyridinyl-phenyl)-1,3-pyrimidine.

[0205] 3.4 g of 2-(2-chlorophenyl)-4-phenyl-6-(4-pyridin-4-ylphenyl)-1,3-pyrimidine, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-(4-pyridin-4-ylphenyl)-1,3-pyrimidine.

[0206] 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-(4-pyridin-4-ylphenyl)-1,3-pyrimidine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 4.00 g (purity 99.9%) of a yellow solid compound

[31] .

[0207] Synthesis Example 10

[0208] Synthesis of Compound

[84]

[0209]

[0210] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0211] 3.4 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0212] 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 2-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 5.0 g of 2-(2-4-chlorophenyl)-2''-(4-phenyl-6-diphenyl-1,3,5-triazine)-4-4-4-terphenyl.

[0213] 5.0 g of 2-(2-4-chlorophenyl)-2''-(4-phenyl-6-diphenyl-1,3,5-triazine)-4-4-4-terphenyl, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 4.20 g (purity 99.9%) of the yellow solid compound

[84] .

[0214] Synthesis Example 11

[0215] Synthesis of Compound

[87]

[0216]

[0217] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0218] 3.4 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0219] 5.0 g of 2-(2-4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 4-chloro-2-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized with 100 ml of o-xylene to obtain 5.1 g of 2-(4-4-chlorophenyl)phenyl-2'-(4-phenyl-6-diphenyl-1,3,5-triazine)-4-4-biphenyl.

[0220] 5.1 g of 2-(4-4-chlorophenyl)phenyl-2'-(4-phenyl-6-diphenyl-1,3,5-triazine)-4-4-biphenyl, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 4.12 g (purity 99.9%) of the yellow solid compound

[87] .

[0221] Synthesis Example 12

[0222] Synthesis of Compound

[99]

[0223]

[0224] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of o-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water, and recrystallized with 50 ml of o-xylene to obtain 3.4 g of white solid 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0225] 3.4 g of 2-(2-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 4-chloro-2-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized with 100 ml of o-xylene to obtain 4.8 g of 2-(2-4-pyridyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0226] 4.8 g of 2-(2-pyridin-4-yl)-4-phenyl-6-diphenyl-1,3-diazinane, 1.8 g of 4-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 5.0 g of 2-((2-(4-chlorophenyl)-pyridin-4-yl)-2'-(4-phenyl-6-diphenyl-1,3-diazinane)-4,4'-terphenyl).

[0227] 5.0 g of 2-((2-(4-chlorophenyl)-pyridin-4-yl)-2'-(4-phenyl-6-diphenyl-1,3-diazinane)-4,4'-terphenyl), 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 4.10 g (purity 99.9%) of a yellow solid compound

[99] .

[0228] Synthesis Example 13

[0229] Synthesis of Compound

[167]

[0230]

[0231] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of 4-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.3 g of white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0232] 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 2-chloro-4-cyanobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 4.7 g of 4-(2-chloro-4-cyano)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0233] Add 4.7 g of 4-(2-chloro-4-cyano)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure. Wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.7 g of 2-(4-chlorophenyl)-4-cyano-4''-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl.

[0234] Add 4.7 g of 2-(4-chlorophenyl)-4-cyano-4''-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure. Wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 4.12 g (purity 99.9%) of the yellow solid compound

[167] .

[0235] Synthesis Example 14

[0236] Synthesis of Compound

[168]

[0237]

[0238] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, evaporate the solvent under reduced pressure. Wash three times with 100 ml of water and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0239] Add 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure. Wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.7 g of 2-(4-chlorophenyl)-4''-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl.

[0240] Add 4.7 g of 2-(4-chlorophenyl)-4”-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl, 1.8 g of 2-chloro-4-cyanobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.8 g of 2-(2-cyano-4-chlorophenyl)-4”-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl.

[0241] Add 4.8 g of 2-(2-cyano-4-chlorophenyl)-4”-4-phenyl-6-diphenyl-1,3,5-triazine-biphenyl, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 4.08 g (purity 99.9%) of the yellow solid compound

[168] .

[0242] Synthesis Example 15

[0243] Synthesis of Compound

[171]

[0244]

[0245] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.22 g of 4-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine.

[0246] Add 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3,5-triazine, 1.8 g of 2-chloro-4-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.7 g of 4-(2-4-pyridyl)-4”-4-phenyl-6-diphenyl-1,3,5-triazine-benzene.

[0247] 4.7 g of 4-(2-4-pyridyl)-4”-4-phenyl-6-diphenyl-1,3,5-triazine-benzene, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness. It was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized with 100 ml of o-xylene to obtain 4.6 g of (2-4-chlorophenyl)-5-pyridin-4-yl-4-phenyl-6-diphenyl-1,3,5-triazine-benzene.

[0248] 4.6 g of (2-4-chlorophenyl)-5-pyridin-4-yl-4-phenyl-6-diphenyl-1,3,5-triazine-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness. It was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 4.01 g (purity 99.9%) of the yellow solid compound

[171] .

[0249] Synthesis Example 16

[0250] Synthesis of Compound

[179]

[0251]

[0252] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness. It was washed three times with 100 ml of water and recrystallized with 50 ml of o-xylene to obtain 3.3 g of the white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0253] 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 2-chloro-4-cyanophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness. It was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized with 100 ml of o-xylene to obtain 4.7 g of 4-(2-4-cyanophenyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0254] Add 4.7 g of 4-(2-4-cyanophenyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.5 g of (2-4-chlorophenyl)-4-cyano-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0255] Add 4.5 g of (2-4-chlorophenyl)-4-cyano-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 3.91 g (purity 99.9%) of the yellow solid compound

[179] .

[0256] Synthesis Example 17

[0257] Synthesis of Compound

[180]

[0258]

[0259] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 1 hour. After cooling to room temperature, evaporate the solvent under reduced pressure, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0260] Add 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.7 g of 4-(2-phenyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0261] Add 4.7 g of 4-(2-phenyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 1.8 g of 3-cyano-4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.2 g of (2-4-chloro-3-cyanophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0262] Add 4.2 g of (2-4-chloro-3-cyanophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 3.88 g (purity 99.9%) of a yellow solid compound

[180] .

[0263] Synthesis Example 18

[0264] Synthesis of Compound

[183]

[0265]

[0266] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.22 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine.

[0267] Add 3.3 g of 2-(4-chlorophenyl)-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.8 g of 2-chloro-5-pyridylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.5 g of 4-(2-chloro-5-pyridyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0268] Add 4.5 g of 4-(2-chloro-5-pyridyl)-4”-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 1.8 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 ° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.1 g of (2-4-chloro-5-pyridyl)-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene.

[0269] Add 4.1 g of (2-4-chloro-5-pyridyl)-4-phenyl-6-diphenyl-1,3-pyrimidine-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 ° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 3.90 g (purity 99.9%) of the yellow solid compound

[183] .

[0270] Synthesis Example 19

[0271] Synthesis of Compound

[237]

[0272]

[0273] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.4 g of 4-chlorobiphenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 ° and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water, and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0274] Add 3.3 g of 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 1.8 g of 2-chloro-5-cyanophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat up to 120 ° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.2 g of 4-(2-chloro-5-cyanophenyl)phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0275] 4.2 g of 4-(2-chloro-5-cyanophenyl)phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. It was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 3.95 g of a yellow solid compound

[237] (purity 99.9%).

[0276] Synthesis Example 20

[0277] Synthesis of Compound

[241]

[0278]

[0279] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.4 g of 4-chlorobiphenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated. It was washed three times with 100 ml of water to obtain 3.3 g of 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene as a white solid by recrystallization with 50 ml of o-xylene.

[0280] 3.3 g of 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 1.8 g of 2-chloro-5-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. It was washed three times with 100 ml of water and 100 ml of methanol respectively to obtain 4.4 g of 4-(2-chloro-5-pyridyl)phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene by recrystallization with 100 ml of o-xylene.

[0281] 4.4 g of 4-(2-chloro-5-pyridyl)phenyl-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated. It was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 3.90 g of a yellow solid compound

[241] (purity 99.9%).

[0282] Synthesis Example 21

[0283] Synthesis of Compound

[249]

[0284]

[0285] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.4 g of 4-chlorobiphenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 1 hour. After cooling to room temperature, evaporate the solvent under reduced pressure, wash it three times with 100 ml of water, and recrystallize it from 50 ml of o-xylene to obtain 3.3 g of white solid 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene.

[0286] Add 3.3 g of 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 1.8 g of 2-chloro-5-cyanobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure, wash it three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize it from 100 ml of o-xylene to obtain 4.2 g of 4-(2-chloro-5-cyanophenyl)phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene.

[0287] Add 4.2 g of 4-(2-chloro-5-cyanophenyl)phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After displacing the air with argon three times, inject dehydrated and deoxygenated toluene. Heat the mixture to 120 °C and react for 7 hours. After cooling to room temperature, evaporate the solvent under reduced pressure, wash it three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize it twice from 100 ml of o-xylene to obtain 3.80 g of yellow solid compound (purity 99.9%).

[0289] Synthesis Example 22

[0290] Synthesis of Compound

[253]

[0291]

[0292] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.4 g of 4-chlorobiphenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water three times, and recrystallize with 50 ml of o-xylene to obtain 3.3 g of white solid 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene.

[0293] Add 3.3 g of 4-chloro-phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 1.8 g of 2-chloropyridine-5-boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water and 100 ml of methanol three times respectively, and recrystallize with 100 ml of o-xylene to obtain 4.2 g of 4-(2-chloro-5-pyridyl)phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene.

[0294] Add 4.2 g of 4-(2-chloro-5-pyridyl)phenyl-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water and 100 ml of methanol three times respectively, and recrystallize with 100 ml of o-xylene twice to obtain 3.94 g of yellow solid compound (purity 99.9%).

[0296] Synthesis Example 23

[0297] Synthesis of Compound

[306]

[0298]

[0299] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.3 g of 4-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate into a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120 °C and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash with 100 ml of water three times, and recrystallize with 50 ml of o-xylene to obtain 3.0 g of white solid 4-chloro-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0300] 3.0 g of 4-chloro-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 1.8 g of 2-chloro-4-cyanobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 4.0 g of 4-(2-chloro-4-cyanophenyl)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0301] 4.0 g of 4-(2-chloro-4-cyanophenyl)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 3.70 g (purity 99.9%) of a yellow solid compound.

[0303] Synthesis Example 24

[0304] Synthesis of Compound

[309]

[0305]

[0306] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3,5-triazine, 1.3 g of 4-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water, and recrystallized from 50 ml of o-xylene to obtain 3.0 g of 4-chloro-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene as a white solid.

[0307] 3.0 g of 4-chloro-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 1.8 g of 2-chloro-5-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene.

[0308] Add 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-diphenyl-1,3,5-triazine)-benzene, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate to a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 3.60 g of a yellow solid compound (purity 99.9%).

[0310] Synthesis Example 25

[0311] Synthesis of Compound

[318]

[0312]

[0313] Add 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.3 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate to a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 1 hour. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water to obtain 3.0 g of white solid 4-chloro-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene by recrystallization with 50 ml of o-xylene.

[0314] Add 3.0 g of 4-chloro-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 1.8 g of 2-chloro-4-cyanophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate to a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize with 100 ml of o-xylene to obtain 4.0 g of 4-(2-chloro-4-cyanophenyl)-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene.

[0315] Add 4.0 g of 4-(2-chloro-4-cyanophenyl)-1-(4-phenyl-6-diphenyl-1,3-pyrimidine)-benzene, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate to a flask. After purging with argon three times, inject dehydrated and deoxygenated toluene. Heat to 120° and react for 7 hours. After cooling to room temperature, rotary evaporate the solvent, wash three times with 100 ml of water and 100 ml of methanol respectively, and recrystallize twice with 100 ml of o-xylene to obtain 3.86 g of a yellow solid compound (purity 99.9%).

[0317] Synthesis Example 26

[0318] Synthesis of Compound

[321]

[0319]

[0320] 2.67 g of 2-chloro-4-phenyl-6-diphenyl-1,3-pyrimidine, 1.3 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.0 g of white solid 4-chloro-1-(4-phenyl-6-diphenyl-1,3-pyrimidinyl)-benzene.

[0321] 3.0 g of 4-chloro-1-(4-phenyl-6-diphenyl-1,3-pyrimidinyl)-benzene, 1.8 g of 2-chloro-5-pyridylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized from 100 ml of o-xylene to obtain 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-diphenyl-1,3-pyrimidinyl)-benzene.

[0322] 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-diphenyl-1,3-pyrimidinyl)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized twice from 100 ml of o-xylene to obtain 3.78 g of yellow solid compound (purity 99.9%).

[0324] Synthesis Example 27

[0325] Synthesis of Compound

[362]

[0326]

[0327] 2.67 g of 2-chloro-4,6-bis(4-(2-pyridyl)phenyl)-1,3,5-triazine, 1.3 g of 4-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.0 g of white solid 4-chloro-1-(4,6-bis(4-(2-pyridyl)phenyl)-1,3,5-triazine)-benzene.

[0328] 3.0 g of 4-chloro-1-(4,6-bis(4-(2-pyridyl)phenyl)-1,3,5-triazine)-benzene, 1.8 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized from 100 ml of o-xylene to obtain 4.2 g of 4-(2-chloro-4-cyanophenyl)-1-(4,6-bis(4-(2-pyridyl)phenyl)-1,3,5-triazine)-benzene.

[0329] 4.2 g of 4-(2-chloro-4-cyanophenyl)-1-(4,6-bis(4-(2-pyridyl)phenyl)-1,3,5-triazine)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and three times with 100 ml of methanol, and recrystallized twice from 100 ml of o-xylene to obtain 3.61 g (purity 99.9%) of yellow solid compound

[362] .

[0330] Synthesis Example 28

[0331] Synthesis of Compound

[368]

[0332]

[0333] 2.67 g of 2-chloro-4-phenyl-6-(4-(4-pyridyl)phenyl)-1,3-pyrimidine, 1.3 g of 2-chlorophenylboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and recrystallized from 50 ml of o-xylene to obtain 3.0 g of white solid 2-chloro-1-(4-phenyl-6-(4-(4-pyridyl)phenyl)-1,3-pyrimidine)-benzene.

[0334] 3.0 g of 2-chloro-1-(4-phenyl-6-(4-(4-pyridyl)phenyl)-1,3-pyrimidinyl)benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 3.13 g of a yellow solid compound (purity 99.9%).

[0336] Synthesis Example 29

[0337] Synthesis of Compound

[369]

[0338]

[0339] 2.67 g of 2-chloro-4-phenyl-6-biphenyl-1,3-pyrimidine, 1.3 g of 2-chloropyridine-4-boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water to obtain 2.7 g of a white solid, 2-chloro-1-(4-phenyl-6-biphenyl-1,3-pyrimidinyl)-4-pyridine, by recrystallization from 50 ml of o-xylene.

[0340] 2.7 g of 2-chloro-1-(4-phenyl-6-biphenyl-1,3-pyrimidinyl)-4-pyridine, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 3.01 g of a yellow solid compound

[369] (purity 99.9%).

[0341] Synthesis Example 30

[0342] Synthesis of Compound

[370]

[0343]

[0344] 2.67 g of 2-chloro-4-phenyl-6-(4-(4-pyridyl)phenyl)-1-pyridine, 1.3 g of o-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water, and recrystallized from 50 ml of o-xylene to obtain 3.0 g of white solid 2-chloro-1-(4-phenyl-6-(4-(4-pyridyl)phenyl)-1-pyridine)-benzene.

[0345] 3.0 g of 2-chloro-1-(4-phenyl-6-(4-(4-pyridyl)phenyl)-1-pyridine)-benzene, 2.2 g of fluorantheneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice from 100 ml of o-xylene to obtain 3.01 g (purity 99.9%) of yellow solid compound.

[0347] Synthesis Example 31

[0348] Synthesis of Compound

[371]

[0349]

[0350] 2.67 g of 2-chloro-4-phenyl-6-(4-deuterophenyl)phenyl-1,3-pyrimidine, 1.3 g of p-chlorobenzeneboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water, and recrystallized from 50 ml of o-xylene to obtain 3.0 g of white solid 4-chloro-1-(4-phenyl-6-(4-deuterophenyl)phenyl-1,3-pyrimidine)-benzene.

[0351] 3.0 g of 4-chloro-1-(4-phenyl-6-(4-deuterophenyl)phenyl-1,3-pyrimidine)-benzene, 1.8 g of 2-chloro-5-pyridineboronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium(II), and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized from 100 ml of o-xylene to obtain 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-(4-deuterophenyl)phenyl-1,3-pyrimidine)-benzene.

[0352] 3.8 g of 4-(2-chloro-5-pyridyl)-1-(4-phenyl-6-(4-deuterophenyl)phenyl)-1,3-pyrimidine, 2.2 g of fluoranthene boronic acid, 0.06 g of dichlorobis(triphenylphosphine)palladium, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The temperature was raised to 120 °C and the reaction was carried out for 7 hours. After cooling to room temperature, the solvent was evaporated to dryness, and the residue was washed three times with 100 ml of water and 100 ml of methanol respectively, and recrystallized twice with 100 ml of o-xylene to obtain 3.88 g of a yellow solid compound

[371] (purity 99.9%).

[0353] Example 1

[0354] A glass substrate (manufactured by Geomatec Co., Ltd., 11 Ω / □, sputtered product) with a 165 nm ITO transparent conductive film deposited thereon was cut into 38 mm × 46 mm and etched. The obtained substrate was ultrasonically cleaned for 15 minutes with "SemicoClean 56" (trade name, manufactured by Furuuchi Chemical Co., Ltd.), and then washed with ultrapure water. Before fabricating the device, the substrate was subjected to ultraviolet (UV)-ozone treatment for 1 hour, placed in a vacuum evaporation apparatus, and evacuated until the vacuum degree inside the apparatus reached 5×10 -4 Pa or less. First, 75 nm of HAT-CN6 was evaporated as a hole injection layer and 42.5 nm of HT-1 was evaporated as a hole transport layer by the resistance heating method. Then, the host material H-1 and the dopant material D-1 were evaporated to a thickness of 20 nm so that the doping concentration became 5 wt% as a light-emitting layer. Then, 30 nm of the compound [3] was deposited as an electron transport layer. Then, after evaporating 1 nm of Yb, 15 nm of Mg / Aa (1:9) was evaporated as a cathode to fabricate a 5 mm × 5 mm square device. The film thickness here refers to the value displayed by a quartz crystal oscillator film thickness monitor (Eon LT of Conltaec). The characteristics of this light-emitting device at 10 mA / cm 2 were a driving voltage of 4.40 V and an efficiency of 6.0 cd / A. Moreover, when the initial brightness was set to 10 mA / cm 2 and constant current driving was performed, the brightness half-life time when the brightness decreased by 50% was 2000 hours. Among them, HAT-CN6, HT-1, H-1, and D-1 are the compounds shown below.

[0355]

[0356] Examples 2 to 33

[0357] A light-emitting element was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 1 was used in the electron transport layer.

[0358] Comparative Examples 1 to 13

[0359] A light-emitting element was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 1 was used in the electron transport layer. C-1 to C-11 are the compounds shown below.

[0360]

[0361]

[0362] [Table 1]

[0363]

[0364]

[0365] Comparative Examples 1-6 are compounds of known fluoranthene and azabenzene-based hosts. Compared with these compounds, it can be seen from the Examples that overall, after adding the azabenzene-based host, there is an effect of reducing the voltage and improving the efficiency. In particular, according to Examples 1-9, 23-27, it can be seen that when the aromatic ring connecting the fluoranthene host and the azabenzene-based host is 3, higher efficiency can be achieved, and according to Examples 10-22, it can be seen that when using an aromatic ring connecting the fluoranthene host and the azabenzene-based host with 2, lower voltage can be obtained.

[0366] Furthermore, from the comparison of, for example, Examples 3, 4 with 9, 10, it can be seen that when using triazine in the compound, longer lifetime can be achieved, and when using pyrimidine, the efficiency can be further improved.

[0367] Comparing Examples 28, 29, 30 with other Examples, it can be seen that when the number of benzene rings connecting the fluoranthene host and the azabenzene-based host is 1, although there is progress compared with the Comparative Examples, due to the lack of a linear structure in the connecting part, the electron transport ability is reduced, so the overall device performance is not as good as the cases where the number of benzene rings is 2 and 3.

[0368] Furthermore, comparing Example 28 with Examples 29, 30, it can be seen that when the azabenzene-based host is pyrimidine or triazine, more electrons can be provided compared with pyridine, thus further reducing the voltage and improving the efficiency.

[0369] Comparing Example 31 with Example 26, it can be seen that introducing deuterium into the molecule can improve the lifetime of the device.

[0370] Some other older Comparative Examples were also used for comparison.

[0371] Comparative Examples 7 and 8 compared with the Examples show that when using a linear structure, since the distance between the fluoranthene host and the azabenzene host is relatively far, its electron transport ability is relatively weak, resulting in a low efficiency of the device.

[0372] Comparative Examples 9, 10, and 11 compared with the Examples show that in the structure using a hetero-fused ring, since the hetero-fused ring disperses the electrons of the heteroatoms, the path from the fluoranthene host to the azabenzene host becomes disordered, thus reducing the electron transport ability, resulting in a high voltage and a low efficiency of the device. In particular, in Comparative Example 9, the ortho structure is used twice, and such a structure will further disorder the overall electron flow, resulting in a further increase in voltage and a decrease in efficiency of its device performance compared with Comparative Examples 10 and 11. Therefore, using heteroaryl with a monocyclic structure such as pyridine and cyanophenyl at the connection part between the fluoranthene and the azabenzene host or the periphery of the azabenzene host can improve the electron transport ability.

[0373] Comparing Comparative Examples 2, 12, and 13 with Examples 26, 32, and 33 shows that after increasing the heteroatoms in the molecule, the coordination between the molecule and Liq is strengthened, thus improving the problem of unstable process when Compound C2 is used.

[0374] However, it should be pointed out that the performance of the device is not a linear superposition of the performance of each layer of material, but the cooperation of multiple layers of materials. Therefore, when the surrounding materials change, there will also be a corresponding most suitable electron transport layer material. Therefore, the present invention provides a series of materials to adjust the molecules for different actual devices.

Claims

1. A fluoranthene derivative having the structure shown in the following general formula 1: A, B, C, D, E, F, G are each independently selected from a single bond, a phenyl group which may be substituted, or a monocyclic heteroaryl group which may be substituted; At least one of A, B, C, F, G is a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group; a, b, c, d, e are each independently selected from 0 or 1; When F is a monocyclic heteroaryl group which may be substituted or a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group, d is selected from 1; When G is a monocyclic heteroaryl group which may be substituted or a monocyclic heteroaryl group which may be substituted or a phenyl group substituted with a cyano group, e is selected from 1; Only one of A, B, C is ortho-substituted; The substituents of the above-mentioned phenyl group which may be substituted or heteroaryl group are each independently selected from one or more of hydrogen, deuterium, cyano group, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, a heterocyclic group which may be substituted, an alkenyl group which may be substituted, a cycloalkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted, an aryl ether group which may be substituted, an aryl thioether group which may be substituted, an aryl group which may be substituted, a monocyclic heteroaryl group which may be substituted, a carbonyl group which may be substituted, a carboxyl group which may be substituted, an oxycarbonyl group which may be substituted, a carbamoyl group which may be substituted, a silyl group which may be substituted, an alkylamino group which may be substituted or an arylamino group which may be substituted; X1, X2, X3 are N or C-R1; Wherein R1 is each independently selected from one or more of hydrogen, deuterium, cyano group, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, a heterocyclic group which may be substituted, an alkenyl group which may be substituted, a cycloalkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted, an aryl ether group which may be substituted, an aryl thioether group which may be substituted, an aryl group which may be substituted, a monocyclic heteroaryl group which may be substituted, a carbonyl group which may be substituted, a carboxyl group which may be substituted, an oxycarbonyl group which may be substituted, a carbamoyl group which may be substituted, a silyl group which may be substituted, an alkylamino group which may be substituted or an arylamino group which may be substituted.

2. The fluoranthene derivative according to claim 1, wherein: In the general formula 1, at least two of a, b, c are selected from 1.

3. The fluoranthene derivative according to claim 2, wherein: In the general formula 1, any two of a, b, c are selected from 1, and the other is 0.

4. The fluoranthene derivative according to claim 2, wherein: In the general formula 1, a = b = c = 1.

5. The fluoranthene derivative according to claim 1, wherein: In the general formula 1, at least two of X1, X2, X3 are N.

6. The fluoranthene derivative according to claim 5, wherein: In the general formula 1, two of X1, X2, X3 are N.

7. The fluoranthene derivative according to claim 5, wherein: In the general formula 1, X1, X2, X3 are all N.

8. The fluoranthene derivative according to claim 1, characterized in that: At least one of A, B, C is selected from pyridyl or cyano phenyl.

9. The fluoranthene derivative according to claim 1, wherein: At least one of F, G is selected from pyridyl or cyano phenyl.

10. A light-emitting element, in which an organic layer is present between an anode and a cathode, the organic layer being a layer responsible for light emission and / or a layer responsible for treating electrons or holes, and the organic layer contains the fluoranthene derivative according to any one of claims 1-9.

11. The light-emitting element according to claim 10, wherein, The organic layer is a layer responsible for treating electrons or holes, and the organic layer contains the fluoranthene derivative according to any one of claims 1-9.

12. The light-emitting element according to claim 10, wherein, The organic layer has an electron transport layer, and the electron transport layer contains the fluoranthene derivative according to any one of claims 1-9.

13. The light-emitting element according to claim 10, wherein, The organic layer has an electron generation layer, and the fluoranthene derivative according to any one of claims 1-9 is contained in the electron generation layer.

14. The light-emitting element according to claim 10, wherein, The organic layer has a hole blocking layer, and the fluoranthene derivative according to any one of claims 1-9 is contained in the hole blocking layer.

15. A photoelectric conversion element containing the fluoranthene derivative according to any one of claims 1-9.

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