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

Abstract

The present invention provides a fluoranthene derivative and a photoelectric conversion element and a light-emitting element having the fluoranthene derivative. The present invention relates to a fluoranthene derivative represented by general formula (1), which has a specific structure having a fluoranthene host and an azabenzene host. The present invention also relates to an organic thin-film light-emitting device using the derivative, which has high luminous efficiency, low driving voltage, and long life. [Formula 1] TIFF2025501868000096.tif162155

Description

[Technical field]

[0001] The present invention relates to a light-emitting element that converts electrical energy into light and a material used in the light-emitting element, and can be used in fields such as display elements, flat panel displays, backlights, lighting, interiors, signs, billboards, electronic cameras, virtual reality, augmented reality, smart watches, mobile phones, portable computers, tablet computers, displays, in-vehicle displays, in-vehicle tail lights, televisions, and optical signal generators. [Background technology]

[0002] In recent years, there has been active research into organic thin-film light-emitting devices, also known as organic light-emitting diode (OLED) technology. Organic thin-film light-emitting devices emit light when electrons injected from a cathode and holes injected from an anode recombine in an organic light-emitting body sandwiched between the two electrodes. These light-emitting devices are characterized by their small thickness, their ability to emit light with high luminance even at low driving voltages, and their ability to emit multicolor light by selecting the light-emitting material, and as such are attracting increasing attention.

[0003] Since Kodak's CW Tang et al. disclosed that organic thin-film elements can emit light with high brightness, many researches have been conducted on its applications. Currently, OLEDs are already widespread in fields such as bracelets, mobile phones, and televisions. However, there are still many technical challenges, and one of the biggest challenges is to achieve both high efficiency and long life of the element.

[0004] OLEDs need to improve luminous efficiency, reduce driving voltage, and improve durability. Among them, achieving both luminous efficiency and durability is a major challenge. However, in conventional technologies (Patent Documents 1 to 6), it is difficult to sufficiently reduce the driving voltage of the element, and even if the driving voltage can be reduced, the luminous efficiency and durability of the element are insufficient. Thus, there is no technology that can achieve high luminous efficiency, low driving voltage, and durability at the same time. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2008 / 059713 [Patent Document 2] International Publication No. 2007 / 100010 [Patent Document 3] International Publication No. 2012 / 108388 [Patent Document 4] International Publication No. 2013 / 065213 [Patent Document 5] International Publication No. 2014 / 057874 [Patent Document 6] International Publication No. 2015 / 182547 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide an organic thin-film light-emitting device which overcomes the above-mentioned problems of the prior art and has improved luminous efficiency, driving voltage and durability. [Means for solving the problem]

[0007] In the present invention, by adjusting the number of fluoranthene hosts and azabenzine hosts in the fluoranthene derivative and their nitrogen content, the amount of electrons capable of being transported in the molecule can be controlled, and the luminous efficiency, driving voltage and durability can be adjusted.

[0008] The fluoranthene derivative provided by the present invention has a structure represented by the following general formula (1). General formula (1)

[0009] [ka]

[0010] (L1 is a substituted or unsubstituted arylene group, L2 is a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. X1, X2, X3, X4, and X5 are the same or different and each independently represents N or C-R1. R1 is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl ... It is selected from one or more of an unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted alkylamino group, or a substituted or unsubstituted arylamino. When X1, X3, and X5 are all N, X2 and X4 are all C-R1, R1 is all phenyl groups, and L1 and L2 are all phenylene groups, at least one of L1 and L2 is selected from an o-phenylene group or a p-phenylene group. n1 and n4 are integers of 1 to 3. n2 and n3 are integers of 0 to 3.) The present invention also provides a light-emitting device, in which an organic layer exists between an anode and a cathode, the organic layer containing the fluoranthene derivative.

[0011] The present invention also discloses a photoelectric conversion element containing the above-described fluoranthene derivative. Effect of the Invention

[0012] According to the present invention, it is possible to provide an organic thin-film light-emitting element that simultaneously achieves high luminous efficiency, low driving voltage, and high durability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Specific embodiments of the present invention will be described in detail below.

[0014] First, the fluoranthene derivative having a structure represented by general formula (1) provided by the present invention will be described in detail. General formula (1)

[0015] [ka]

[0016] (L1 is a substituted or unsubstituted arylene group, L2 is a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. X1, X2, X3, X4, and X5 are the same or different and each independently represents N or C-R1. R1 is each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl ... It is selected from one or more of an unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted alkylamino group, or a substituted or unsubstituted arylamino. When X1, X3, and X5 are all N, X2 and X4 are all C-R1, R1 is all phenyl groups, and L1 and L2 are all phenylene groups, at least one of L1 and L2 is selected from an o-phenylene group or a p-phenylene group. n1 and n4 are integers of 1 to 3. n2 and n3 are integers of 0 to 3.) In all of the above groups, hydrogen may be replaced by deuterium.

[0017] In the present specification, when the term "substituted or unsubstituted" is used, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted carbazole ... The substituent is preferably one or more of the following: phenyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted oxycarbonyl group, substituted or unsubstituted aminocarbonyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkylamino group or substituted or unsubstituted arylamino group, halogen, cyano group, carbonyl group, carboxyl group, oxycarbon group, aminocarbonyl group, phosphine oxide group, condensed aromatic hydrocarbon ring, monocyclic aromatic heterocycle and condensed aromatic heterocycle, more preferably, the specific substituent is preferably in the description of each substituent.These substituents can be further substituted or unsubstituted with the above-mentioned substituent.

[0018] When referring to "substituted or unsubstituted", "unsubstituted" refers to substitution with a hydrogen atom.

[0019] In the compounds or partial structures thereof described below, the same applies as above when it is referred to as being "substituted or unsubstituted".

[0020] The alkyl group represents a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, etc., and may or may not have a substituent. If the alkyl group is substituted, the additional substituent is not particularly limited, and may be, for example, an alkyl group, an aryl group, a heteroaryl group, etc., and this point is common to the following description. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20 in terms of ease of material availability and cost.

[0021] The cycloalkyl group refers to a saturated aliphatic cycloalkyl group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, etc., which may or may not have a substituent. The number of carbon atoms in the alkyl portion is not particularly limited, but is preferably in the range of 3 to 20 in terms of ease of material availability and cost.

[0022] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or butadiene, which may or may not have a substituent. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 3 to 20 in terms of ease of material availability and cost.

[0023] The cycloalkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, etc., which may or may not have a substituent. The number of carbon atoms in the alkenyl group is not particularly limited, but is preferably in the range of 3 to 20 in terms of ease of material availability and cost.

[0024] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group. The number of carbon atoms in the alkynyl group, which may or may not have a substituent, is not particularly limited, but is preferably in the range of 3 to 20 in terms of ease of material availability and cost.

[0025] The alkoxy group refers to a functional group having an aliphatic hydrocarbon group bonded via an ether bond, such as a methoxy group, an ethoxy group, a propoxy group, etc., and the aliphatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably in the range of 1 to 20 in terms of ease of material availability and cost.

[0026] An alkylthio group is an alkoxy group in which the oxygen atom of the ether bond is replaced with a sulfur atom. The hydrocarbon group of the alkylthio group may or may not have a substituent. The number of carbon atoms in the alkylthio group is not particularly limited, but is preferably in the range of 1 to 20 in terms of ease of material availability and cost.

[0027] The aryl ether group refers to a functional group having an aromatic hydrocarbon group bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may or may not have a substituent. The number of carbon atoms in the aryl ether group is not particularly limited, but is preferably in the range of 6 to 40 in terms of ease of material availability and cost.

[0028] The aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is replaced with a sulfur atom. The aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent. The number of carbon atoms in the aryl thioether group is not particularly limited, but is preferably in the range of 6 to 40 in terms of material availability and cost.

[0029] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group, or a 1,2-benzoacenaphthylenyl group. The aryl group may or may not have a substituent. The number of carbon atoms in the aryl group is not particularly limited, but is preferably in the range of 6 to 40 in terms of material availability and cost.

[0030] The heteroaryl group refers to a cyclic aromatic group having an atom other than carbon in one or more rings, such as a furanyl group, a thiophenyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a pyrazinyl group, a pyrimidinyl group, a naphthyridinyl group, a benzofuranyl group, a benzophenylthio group, an indolyl group, a dibenzofuranyl group, a dibenzophenylthio group, a carbazolyl group, etc., and may be substituted or unsubstituted. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably in the range of 2 to 30 in terms of ease of material availability and cost.

[0031] Halogen refers to an atom selected from fluorine, chlorine, bromine and iodine.

[0032] The carbonyl group, carboxyl group, oxycarbonyl group, cyano group, carbamoyl group and phosphine oxide group may or may not have a substituent. Examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc., and these substituents may be further substituted or unsubstituted.

[0033] The arylene group represents a divalent or trivalent group derived from an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, or a biphenyl group, and may or may not have a substituent.

[0034] When L1 in the general formula (1) is an arylene group, the number of nuclear carbon atoms is preferably in the range of 6 to 24, more preferably 6 to 12. Specific examples of the arylene group include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 4,4'-biphenylene group, 4,3'-biphenylene group, 3,3'-biphenylene group, 1,4-naphthylene group, 1,5-naphthylene group, 2,5-naphthylene group, 2,6-naphthylene group, and 2,7-naphthylene group. The 1,4-phenylene group and the 1,3-phenylene group are more preferred.

[0035] The heteroarylene group represents a divalent or trivalent substituent derived from an aromatic group having an atom other than carbon in one or more rings, such as a pyridyl group, a quinolyl group, a pyrimidyl group, a pyrazinyl group, a naphthyridinyl group, a dibenzofuranyl group, a dibenzophenylthio group, etc., and may or may not have a substituent. The number of carbon atoms in the heteroarylene group is not particularly limited, but is preferably in the range of 2 to 30.

[0036] 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 (chrysene) ring, a tetracene ring, a triphenylene ring, an acenaphthene ring, a hexacene ring, a fluorene ring, a 1,2-benzoacenaphthylene ring, a tetracene ring, a pentacene ring, a perylene ring, a pentacene ring, a picene ring, a pyranthrene ring, an anthraanthrene ring, etc. The condensed aromatic hydrocarbon ring may have a substituent.

[0037] 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. The monocyclic aromatic heterocycle may have a substituent.

[0038] Examples of the fused 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 representing the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom), etc. The fused aromatic heterocycle may have a substituent.

[0039] The present invention provides a hybrid fluoranthene derivative of fluoranthene and an azobenzene host, in which fluoranthene has a structure in which one cyclopentane is surrounded by three benzene rings, and electrons can be delocalized throughout the fluoranthene structure, while the cyclopentane portion forms an electron cavity portion and tends to absorb electrons. The azabenzene host may be benzene or azabenzene containing multiple nitrogen atoms, and the π electron system of the benzene itself in the azabenzene system can move throughout the molecule, and increasing the nitrogen in the azabenzene host allows the lone pair of nitrogen to further increase the delocalized electrons in the π electron system, enhancing the electron transport ability. The azabenzene host has a weak ability to attract electrons to the atomic nucleus, and the fluoranthene portion tends to attract electrons, which causes the electrons to move toward the fluoranthene portion throughout the molecule (although the molecule itself is neutral), and such a molecule can provide electron transport ability by imitating the delocalization of electrons in a metal key to some extent during film formation. On the other hand, an excess of fluoranthene hosts disrupts the flow of electrons and reduces the efficient transport ability of electrons, and an excess of nitrogen excessively lowers the LUMO, causing the energy level of the electronic processing material to not match with the surrounding materials. Therefore, the number of fluoranthene hosts and the number of azabenzene-based hosts must be precisely controlled for each molecule. Considering the energy level matching of the materials, electronic processing ability, difficulty of synthesis, and cost, it is preferable that the number of fluoranthene hosts (n1) is 1 and the number of azabenzene-based hosts (n4) is 1.

[0040] Research has shown that using a condensed ring compound such as naphthalene at the point where the azabenzene host is directly linked (i.e., at the L2 position) tends to disrupt the electrons supplied from the azabenzene host, reducing the electronic processing performance of the molecule. Therefore, a non-condensed ring phenylene group is used at the L2 position.

[0041] Through research, we have found that when n1=1 and the value of n1×n2+n3×n4 is within 1~5, the energy levels of the molecule can match common OLED systems in most markets.

[0042] Furthermore, when n1=1 and the value of n1×n2+n3×n4 is within a range of 2 to 3, the number of delocalized electrons in the molecule reaches an optimal level, making it possible to realize optimal device performance.

[0043] As mentioned above, the number of nitrogen atoms in the azabenzene host needs to be precisely controlled. Considering the energy levels of materials adjacent to general electronic processing materials and actual test results, when X1, X2, X3, X4, and X5 have 0 to 3 nitrogen atoms, they have good electronic processing performance.

[0044] In particular, there is better efficiency when there are two Ns among X1, X2, X3, X4, and X5.

[0045] In particular, if there are three Ns among X1, X2, X3, X4, and X5, it can have a longer life.

[0046] By adding a benzene-based aromatic group substituent to the substituent of the azobenzene-based host, the energy level and electron donating ability of the entire azobenzene-based host can be finely adjusted and more precise control can be realized. Therefore, when C-R1 is represented by X1, X2, X3, X4, and X5, R1 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted furyl group (e.g., a dibenzofuranyl group is preferable), or a substituted or unsubstituted carbazolyl group, a fluorenyl group, and a dibenzothienyl group.

[0047] In particular, when X2 is C-(Ph)n5, X4 is C-(Ph)n6, Ph is a phenyl group, and n5+n6>2, it can be most widely applied to more peripheral layer materials and has the best effect.

[0048] Different n5 and n6 can improve the productivity and deposition performance of the molecule.

[0049] Research has found that when the azabenzene body is triazine and the substituent is two benzenes, due to its electron donating ability, it is more suitable to transfer to the fluoranthene body via L1 and L2 at para or ortho positions.Therefore, in the azabenzene body, when X1, X3, X5 are all nitrogen atoms, X2 and X4 are all C-R1, and R1 is a phenyl group, and L1 and L2 are phenylene groups, at least one of L1 and L2 is selected from o-phenylene group or p-phenylene group.

[0050] It is clear that when the linking moieties L1 and L2 are selected from phenylene groups, electrons can be transferred from the azabenzene body to the fluoranthene body better.However, when L1 and L2 are both selected from m-phenylene groups, the transport of electrons is bent, so that it is resisted, while the azabenzene body and the fluoranthene body are too far apart, so that there is no spatial effect, which reduces the overall transport ability.Therefore, when the fluoranthene derivative is used as an electron transport layer material, L1 and L2 cannot be m-phenylene groups at the same time.

[0051] In particular, the o-phenylene group can bring the azobenzene body closer to the fluoranthene body, improve the molecular orientation, and achieve low-voltage, high-efficiency performance. Therefore, it is preferable that at least one of L1 and L2 is an o-phenylene group.

[0052] In particular, when at least one of L1 and L2 is an o-phenylene group, the structure using biphenyl-added benzene as a substituent of the azabenzene body can have better electrical properties than bisbenzene, because the steric hindrance-eliminating effect of biphenyl restricts the rotation of the azabenzene body, thereby enhancing the stability of the large delocalized π electrons and enhancing the electronic processing performance.

[0053] In addition, when a nitrogen-containing substituent (e.g., pyridine, pyrimidine, etc.) is added to the substituent of the azabenzene body, the energy levels of the two azabenzene bodies are too low to match with the surrounding materials. On the other hand, when the azabenzene body is substituted with a nitrogen-containing substituent, the chemical bond between them has a low electron cloud density and is easily cleaved because electrons are pulled out by each of the two azabenzene bodies. Therefore, it is not preferable to select the substituent of the azabenzene body from a nitrogen-containing substituent.

[0054] In practice, it is believed that the following molecular structures and their derived structures can provide comprehensively excellent performance in the three areas of efficiency, voltage, and life, depending on the specific device structure and device application, and therefore the following compounds are preferred.

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[0077] The present invention also discloses a light-emitting device, in which an organic layer is present between an anode and a cathode of the light-emitting device, the organic layer being a layer responsible for emitting light and / or a layer responsible for processing electrons or holes, and the organic layer contains the fluoranthene derivative.

[0078] Considering the electron handling ability of such materials, it is preferable that the organic layer has an electron transport layer containing the fluoranthene derivative.

[0079] Considering that such materials contain many electrons exceeding the atomic nucleus binding capacity, the organic layer preferably has an electron generating layer containing the fluoranthene derivative.

[0080] Considering that this type of material is specialized for handling electrons and its energy level is not suitable for transporting holes, the organic layer preferably has a hole blocking layer containing the fluoranthene derivative.

[0081] The present invention also discloses a photoelectric conversion element containing the fluoranthene derivative.

[0082] A known method can be used for the synthesis of the fluoranthene derivative of the present invention. A method for introducing an azabenzene-based body into the fluoranthene derivative skeleton includes, for example, a method using a coupling reaction between a substituted or unsubstituted halogenated fluoranthene body and a substituted or unsubstituted azabenzene-based body under a palladium catalyst or nickel catalyst, but is not limited to these methods. In addition, when an azabenzene-based body is introduced into this fluoranthene derivative via an arylene group or a heteroarylene group, the azabenzene-based body may be a substituted arylboronic acid or a heteroarylboronic acid, or a fluoranthene body substituted with a halogenated aryl group. In addition, a boric acid ester may be used instead of the various boric acids.

[0083] Next, an embodiment of the light-emitting device of the present invention will be described in detail. The light-emitting device of the present invention includes an anode, a cathode, and an organic layer inserted between the anode and the cathode, the organic layer including at least a light-emitting layer and an electron transport layer, and the light-emitting layer emits light when exposed to electric energy.

[0084] The organic layer may have a structure consisting of only a light-emitting layer / electron transport layer, or may have a laminated structure consisting of 1) a hole-transport layer / light-emitting layer / electron transport layer, 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, and 4) a hole-injection layer / hole-transport layer / electron blocking layer / light-emitting layer / hole-blocking layer / electron transport layer / electron injection layer, etc. Each of the layers may be a single layer or a multilayer structure connected by an electron-generating layer and a hole-generating layer.

[0085] The fluoranthene derivative of the present invention can be used in any layer in the above-mentioned device configuration, but is preferably used in an electron transport layer, an electron generating layer, or a hole blocking layer because of its high electron injection and transport ability, fluorescent quantum yield, and thin film stability.

[0086] In the light-emitting device of the present invention, the anode and the cathode have the role of supplying a sufficient current for the device to emit light, and at least one of them is preferably transparent or semi-transparent to emit light. A transparent anode or a transparent cathode can be used depending on the actual application and device design.

[0087] The material used for the anode is a material that can efficiently inject holes into the organic layer, and is transparent or semi-transparent to emit light. It is not particularly limited to conductive metal oxides such as tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), metals such as gold, silver, and chromium, inorganic conductive substances such as copper iodide and copper sulfide, and conductive polymers such as polythiophene, polypyrrole, and polyaniline, and it is particularly preferable to use ITO glass or NESA glass. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed. The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the element, but it is preferable that the resistance is low from the viewpoint of the power consumption of the element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since substrates of about 10Ω / □ are currently available, it is particularly preferable to use a substrate with a low resistance of 20Ω / □ or less. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but is usually between 100 nm and 300 nm.

[0088] In addition, in order to maintain the mechanical strength of the light-emitting element, it is preferable to form the light-emitting element on a substrate. The substrate may be a glass substrate such as soda glass or non-alkali glass, or a flexible substrate made of a polymer component. The thickness of the substrate is sufficient as long as the mechanical strength is maintained sufficiently, and therefore 0.5 mm or more is sufficient. As for the glass material, non-alkali glass is preferable because it is preferable that the glass has few ions eluted from the glass. Alternatively, soda lime glass with a barrier coat such as SiO2 is commercially available, and this soda lime glass may be used. In addition, as long as the first electrode functions stably, for example, an anode may be formed on a polyimide substrate. The ITO film forming method is not particularly limited, and may be an electron beam method, a sputtering method, a chemical reaction method, or the like.

[0089] The material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the light-emitting layer. In general, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys or multilayers of these metals and low work function metals such as lithium, sodium, potassium, calcium, and magnesium are preferred. Among them, the main components are preferably aluminum, silver, and magnesium in terms of resistance value, ease of film formation, film stability, and light-emitting efficiency. In particular, if the material is made of magnesium and silver, it is preferred because it facilitates electron injection into the electron transport layer and electron injection layer in the present invention and enables low-voltage driving.

[0090] In addition, in order to protect the cathode, a preferred example is a method in which metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, and organic polymer compounds such as polyvinyl alcohol, polyvinyl chloride, and hydrocarbon-based polymer compounds are laminated on the cathode to form a protective film layer. The fluoranthene derivative of the present invention can also be used as a protective film layer. However, in the case of an element structure in which light is emitted from the cathode side (top emission structure), the protective film layer can be selected from materials that are transparent in the visible light region. The manufacturing method of these electrodes is resistance heating, electron beam, sputtering, ion plating, coating, etc., and is not particularly limited. In order to further improve the light extraction efficiency and reduce the light extraction efficiency due to the lack of transparency of the transparent cathode, an organic material with a high refractive index may be used. In addition, a thin film encapsulation (TFE) layer can be added after optical tuning using metal (e.g. LiF) or low refractive index organic small molecule compounds to provide flexible protection, thereby realizing flexibility and even foldability, and also protecting the device from the effects of moisture and oxygen. The specific structure is not limited.

[0091] The hole transport layer can be formed by laminating or mixing one or more types of hole transport materials, or by using a mixture of a hole transport material and a polymer binder. The hole transport material must efficiently transport holes from the positive electrode between electrodes that apply an electric field, and it is preferable that the hole transport material has high hole injection efficiency and efficiently transports the injected holes. Therefore, it is required that the hole transport material has a suitable ionization potential, a large hole mobility, excellent stability, and is unlikely to generate impurities that become traps during production and use. Examples of compounds that satisfy such conditions include, but are not limited to, benzidine derivatives such as 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-biphenyl)amino)biphenyl (TBDB), and bis(N,N'-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4'-diamino-1,1'-biphenyl (TPD232); stir bars such as 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine (m-MTDATA) and 4,4',4"-tris(1-naphthyl(phenyl)amino)triphenylamine (1-TNATA); The material group called stoichiometric, materials having a carbazole skeleton (particularly carbazole polymers, specifically derivatives of carbazole dimers such as bis(N-arylcarbazole) and bis(N-alkylcarbazole), derivatives of carbazole trimers, and derivatives of carbazole tetramers), triphenylene compounds, pyrazoline derivatives, stilbene compounds, hydrazone compounds, heterocyclic compounds such as benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, and porphyrin derivatives, fullerene derivatives, polycarbonates or styryl derivatives having the monomers in the side chains in polymer systems, polythiophenes, polyanilines, polyfluorenes, polyvinylcarbazoles, and polysilanes. Inorganic compounds such as p-type Si and p-type SiC may also be used.

[0092] The fluoranthene derivative of the present invention has excellent electron injection and transport properties, so when it is used in the electron transport layer, there is a risk that electrons will not be bonded in the light-emitting layer and some of them will 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 carbazole skeleton-containing compound is preferable because it has excellent electron blocking properties and contributes to high efficiency of the light-emitting device. In addition, it is preferable that the carbazole skeleton-containing compound contains a carbazole dimer, a carbazole trimer, or a carbazole tetramer skeleton. This is because these compounds have both good electron blocking properties and hole injection and transport properties. 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 material described later. This is because the compound having the carbazole skeleton also has a high triplet exciton blocking function, and when combined with a phosphorescent material, high light-emitting efficiency is possible. In addition, it is preferable to use a triphenylene skeleton-containing compound, which is excellent in terms of having high hole mobility, in the hole transport layer because it can provide effects such as improved carrier balance, improved light-emitting efficiency, and improved durability. It is more preferable that the triphenylene skeleton-containing compound has two or more diarylamino groups. The carbazole skeleton-containing compound or the triphenylene skeleton-containing compound may be used alone as the hole transport layer, or may be mixed with each other. Other materials may be mixed within a range that does not impair the effects of the present invention. In addition, when the hole transport layer is composed of multiple layers, any one of the layers may contain the carbazole skeleton-containing compound or the triphenylene skeleton-containing compound. However, since the principle of light emission is that one material simultaneously receives electrons and holes, forms excitons, and then returns to the ground state to emit energy and emit light, the light-emitting material layer material needs to be designed to have a structure that receives electrons and holes but does not transmit them. Therefore, the structure is significantly different from that of materials that transmit or block electrons or holes, and the fluoranthene-based compound of the present invention cannot be used in the light-emitting layer.

[0093] A hole injection layer may 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 improved. For the hole injection layer, it is preferable to use a material having a smaller ionization potential than the material usually used for the hole transport layer. Specifically, in addition to the benzidine derivative such as the above-mentioned TPD232, and the starburst arylamine material group, phthalocyanine derivatives and the like can be used. It is also preferable that the hole injection layer is composed of an acceptor compound alone, or that the acceptor compound is doped into another hole transport material. Examples of the acceptor compound 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). In addition, 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. can also be suitably used.Specific examples of these compounds include hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane (TCNQ), tetrafluorotetracyanoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CNQ), 6), p-tetrafluorobenzoquinone (p-fluoranil), p-tetrachlorobenzoquinone, p-tetrabromobenzoquinone, p-benzoquinone, 2,6-dichlorobenzoquinone, 2,5-dichlorobenzoquinone, tetramethylbenzoquinone, 1,2,4,5-tetracyanobenzene, o-dicyanobenzene, p-dicyanobenzene, 1,4-dicyanotetrafluorobenzene, 2,3-dichloro-5,6-dicyanobenzoquinone, p-dinitrobenzene, m-dinitrobenzene, o-dinitrobenzene, p-cyanonitro Examples of the alkylene oxide include benzene, 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-tetracyanopyridine, maleic anhydride, phthalic anhydride, C60, and C70.

[0094] Among these compounds, metal oxides and cyano group-containing compounds are preferred because they are easy to handle and vapor-deposit, and therefore the above-mentioned effects can be easily obtained. Examples of preferred metal oxides include molybdenum oxide, vanadium oxide, and ruthenium oxide. Among cyano group-containing compounds, (a) compounds having at least one electron-accepting nitrogen atom in addition to the nitrogen atom of a cyano group in the molecule, (b) compounds having both a halogen and a cyano group in the molecule, (c) compounds having both a carbonyl group and a cyano group in the molecule, or (d) compounds having both a halogen and a cyano group in the molecule and having at least one electron-accepting nitrogen atom in addition to the nitrogen atom of a cyano group are more preferred because they act as strong electron acceptors. Specific examples of such compounds include the following:

[0095] [ka]

[0096] [ka]

[0097] In either case where the hole injection layer is made of an acceptor compound alone or where the hole injection layer is doped with an acceptor compound, the hole injection layer may be a single layer or may be a laminate of multiple layers. In addition, in the case where the acceptor compound is doped, from the viewpoint of reducing the barrier for injecting holes into the hole transport layer, it is more preferable that the hole injection material used in combination with the hole transport layer is the same compound as the compound used in the hole transport layer.

[0098] The light-emitting layer may be a single layer or a multilayer, each of which is formed from a light-emitting material (main material, dopant material), and may be a mixture of the main material and the dopant material, or may be only the main material. That is, in the light-emitting device of the present invention, in each light-emitting layer, only the main material or the dopant material may emit light, or both the main material and the dopant material may emit light. From the viewpoint of efficiently utilizing electric energy and obtaining light emission with high color purity, it is preferable that the light-emitting layer contains a mixture of the main material and the dopant material. In addition, optionally, the main material and the dopant material may each be one type, or a combination of multiple types. Optionally, the dopant material may be included in the entire main material, or may be included partially. Optionally, the doping material may be laminated or dispersed. The dopant material can control the emission color. If the amount of the dopant material is too large, concentration quenching phenomenon occurs, so it is preferable to use it in an amount of 20% by weight or less, more preferably 10% by weight or less, based on the main material. As a doping method, the dopant may be formed by co-evaporation with the main body material, or may be mixed with the main body material in advance and then evaporated at the same time.

[0099] Specific examples of the luminescent material that can be used include, but are not limited to, condensed ring derivatives such as anthracene and pyrene, which are conventionally known as luminescent bodies; metal chelate doxinoid compounds such as tris(8-quinolinolato)aluminum; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene 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, polyphenyleneacetylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives in polymerization systems.

[0100] The main material contained in the luminescent material is not particularly limited, and examples thereof include compounds having a condensed aryl ring, such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, tetracene, triphenylene, perylene, 1,2-benzoacenaphthylene, fluorene, and indene, or derivatives thereof, aromatic amine derivatives such as N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, metal chelated oxinoid compounds, such as tris(8-quinolinolato)aluminum(III), and distyrylbenzene derivatives. Examples of the compound that can be used include, but are not limited to, bisstyryl derivatives such as styrene-butadiene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, pyrrolopyrrole derivatives, thiadiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivatives, triazine derivatives, polymer-based polyphenylenevinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives.In addition, the dopant material is not particularly limited, but examples thereof include compounds having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, triphenylene, perylene, 1,2-benzoacenaphthylene, fluorene, and indene, or derivatives thereof (for example, 2-(benzothiazol-2-yl)-9,10-diphenylanthracene or 5,6,11,12-tetraphenyltetracene, etc.), furan, pyrrole, thiophene, Having a heteroaryl ring such as silacyclopentadiene, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioanthracene, etc. Compounds or derivatives thereof, borane derivatives, distyrylbenzene derivatives, aminostyryl derivatives such as 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl and 4,4'-bis(N-(stilben-4-yl)-N-phenylamino)stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldehyde azo derivatives, pyrromethene derivatives, diketopyrrolopyrrole[3,4-c]pi coumarin derivatives such as 2,3,5,6-1H,4H-tetrahydro-9-(2'-benzothiazolyl)quinolidinyl[9,9a,1-gh]coumarin, etc. azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole, etc. and their metal complexes, aromatic amine derivatives represented by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, etc.

[0101] The light-emitting layer may also contain a phosphorescent material. The phosphorescent material is a material that exhibits phosphorescence even at room temperature. When using a phosphorescent material as a dopant, it is basically necessary to obtain phosphorescence even at room temperature, and although there is no particular limitation, 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) is preferred. Among them, from the viewpoint of having a high phosphorescence yield even at room temperature, an organometallic complex containing iridium or platinum is more preferred. As the main body used in combination with the phosphorescent dopant, indole derivatives, carbazole derivatives, indolocarbazole derivatives, nitrogen-containing aromatic compound derivatives having pyridine, pyrimidine, or triazine skeletons, aromatic hydrocarbon compound derivatives such as polyarylbenzene derivatives, spirofluorene derivatives, tripolyindene (truxene) derivatives, and triphenylene derivatives, sulfur-containing compounds such as dibenzofuran derivatives and dibenzothiophene derivatives, and organometallic complexes such as quinolinol beryllium complexes are preferably used, and are not limited to these as long as they have a higher triplet energy than the dopant basically used and allow electrons and holes to be smoothly injected and transported from each transport layer. In addition, the main body may contain two or more triplet light-emitting dopants, and may contain two or more main body materials. In addition, the main body may contain one or more triplet light-emitting dopants and one or more fluorescent light-emitting dopants.

[0102] Preferred phosphorescent bodies or dopants are not particularly limited, but specific examples include those shown below.

[0103] [ka]

[0104] [ka]

[0105] In the present invention, the electron transport layer is a layer into which electrons are injected from the cathode and which transports the electrons. An ideal electron transport layer has high electron injection efficiency and can efficiently transport the injected electrons. Therefore, it is preferable that the electron transport layer is made of a material that has a large electron affinity, a large electron mobility, excellent stability, and is unlikely to generate impurities that become traps during production and use. However, when considering the balance of hole and electron transport, if the electron transport layer mainly plays a role of efficiently blocking holes from the anode from flowing to the cathode without binding, even if the electron transport layer is made of a material with a low electron transport ability, the effect of improving the luminous efficiency will be the same as when the electron transport layer is made of a material with a high electron transport ability. Therefore, the electron transport layer in the present invention also includes a substance synonymous with the hole blocking layer that can efficiently block the movement of holes.

[0106] Examples of electron transport materials used in the electron transport layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylvinyl)biphenyl, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, quinolinol complexes such as tris(8-quinolinolato)aluminum(III), benzoquinolinol complexes, hydroxyoxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. In order to reduce the driving voltage and obtain highly efficient light emission, it is preferable to use a compound that is composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus and has a heteroaryl ring structure containing electron-accepting nitrogen.

[0107] Aromatic heterocycles containing electron-accepting nitrogen have high electron affinity. Electron-transporting materials with electron-accepting nitrogen are more likely to accept electrons from a cathode with high electron affinity, allowing for lower voltage operation. Meanwhile, the lone pair of electron-accepting nitrogen can accommodate more electrons after merging into a large π-electron system, improving the load of electron transport and improving the electron transport capacity. In addition, the supply of electrons to the light-emitting layer is increased, increasing the recombination probability, thereby improving the luminous efficiency.

[0108] Examples of heteroaryl rings containing an electron-accepting nitrogen include a pyridine ring, a pyrazine ring, a pyrimidine ring, a quinoline ring, a quinoxaline ring, a naphthyridine ring, a pyrimidopyrimidine 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 phenanthreneimidazole ring.

[0109] Examples of 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 and terpyridine, quinoxaline derivatives, and naphthyridine derivatives. Among these, 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 and 1,3-bis(1,10-phenanthroline-9-yl)benzene, 2,2' Benzoquinoline derivatives such as -bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, bipyridine derivatives such as 2,5-bis(6'-(2',2"-bipyridine))-1,1-dimethyl-3,4-diphenylsilacyclopentadiene, terpyridine derivatives such as 1,3-bis(4'-(2,2':6'2"-terpyridine))benzene, and naphthyridine derivatives such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide can be preferably used. These derivatives are more preferable because they have a condensed polycyclic aromatic skeleton, which increases the glass transition temperature and electron mobility, and has a large effect of reducing the voltage of the light-emitting element. In addition, in consideration of the improvement of the durability life of the element, the ease of synthesis, and the ease of obtaining raw materials, it is particularly preferable that the condensed polycyclic aromatic skeleton is an anthracene skeleton, a pyrene skeleton, or a phenanthroline skeleton. The electron transport material may be used alone, or may be used by mixing two or more of the electron transport materials, or may be used by mixing one or more of other electron transport materials with the electron transport material. The fluoranthene derivative of the present invention also has high electron injection and transport ability, so it can be suitably used as an electron transport material.

[0110] When using the fluoranthene derivative of the present invention, it is not necessary to limit each to one type, and a plurality of types of fluoranthene compounds of the present invention may be mixed and used, or one or more types of other electron transport materials may be mixed with the fluoranthene compound of the present invention within a range that does not impair the effects of the present invention. Examples of electron transport materials that can be mixed include, but are not limited to, compounds having condensed aryl rings such as naphthalene, anthracene, pyrene, etc., or derivatives thereof, styryl aromatic ring derivatives such as 4,4'-bis(diphenylvinyl)biphenyl, perylene derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives, quinolinol complexes such as tris(8-quinolinolato)aluminum(III), hydroxyoxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, triphenol ketone metal complexes, and flavonoid alcohol metal complexes.

[0111] The electron transport material may be used alone, or may be used by mixing two or more of the electron transport materials, or may be used by mixing one or more other electron transport materials with the electron transport material. The electron transport material may also contain a donor material. Here, the donor material is a compound that improves the electron injection barrier, thereby facilitating electron injection from the cathode or the electron injection layer to the electron transport layer, and further improves the conductivity of the electron transport layer.

[0112] Preferable 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, etc. Preferable types of alkali metals and alkaline earth metals include alkali metals such as lithium, sodium, cesium, ytterbium, etc., which have a low work function and a large effect of improving the electron transport ability, and compounds thereof, and alkaline earth metals such as magnesium, calcium, etc., and compounds thereof.

[0113] A suitable doping concentration varies depending on the material and 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-deposit the electron transport material and the donor material so that the deposition rate ratio is in the range of 10000:1 to 2:1 to form an electron transport layer. The deposition rate ratio is more preferably 100:1 to 5:1, and even more preferably 100:1 to 10:1. When the donor material is a complex of a metal and an organic material, it is preferable to co-deposit the electron transport material and the donor material so that the deposition rate ratio is in the range of 100:1 to 100 to form an electron transport layer. The deposition rate ratio is more preferably 10:1 to 1:10, and even more preferably 7:3 to 3:7.

[0114] Moreover, the electron transport layer obtained by doping the fluoranthene derivative of the present invention with a donor material as described above can be used as a charge generating layer in a tandem structure element in which a plurality of light emitting elements are connected.

[0115] The method of doping the electron transport layer with a donor material to improve the electron transport ability is particularly effective when the thin film layer is thick. It can be particularly preferably used when the total thickness of the electron transport layer and the light emitting layer is 50 nm or more. For example, there is a method of improving the light emission efficiency by aligning the phase of the light directly emitted from the light emitting layer with the light reflected by the cathode, and utilizing the interference effect to improve the light emission efficiency. The optimal condition varies depending on the emission wavelength of the light, but when the total thickness of the electron transport layer and the light emitting layer is 50 nm or more, and in the case of long wavelength emission such as red, the film may become thick, approaching 100 nm.

[0116] The thickness of the electron transport layer to be doped may be either a part or the whole of the electron transport layer. When a part of the electron transport layer is doped, it is desirable to provide a doped region at least at the electron transport layer / cathode interface, and the effect of reducing the voltage can be obtained even if the doped region is only near the cathode interface. On the other hand, when the donor material is in direct contact with the light emitting layer, it may have an adverse effect of reducing the light emitting efficiency, and in this case, it is preferable to provide an undoped region at the light emitting layer / electron transport layer interface.

[0117] In the present invention, an electron injection layer may be provided between the cathode and the electron transport layer. In general, the electron injection layer is inserted for the purpose of contributing to electron injection from the cathode to the electron transport layer. In the case of insertion, a compound having a heteroaryl ring structure containing electron-accepting nitrogen may be used, or a layer containing the above-mentioned donor material may be used. The fluoranthene derivative of the present invention may be included in the electron injection layer. In addition, an inorganic material such as an insulator or semiconductor, or a metal may be used for the electron injection layer. By using these materials, it is possible to effectively prevent short circuits in the light-emitting device and improve the electron injection property, which is preferable. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of an alkali metal chalcogen compound, an alkaline earth metal chalcogen compound, an alkali metal halide, and an alkaline earth metal halide. It is more preferable that the electron injection layer is composed of these alkali metal chalcogen compounds, etc., in that it can further improve the electron injection property. Specifically, preferred alkali metal chalcogen compounds include Li2O, Na2S, and Na2Se, and preferred alkaline earth metal chalcogen compounds include CaO, BaO, SrO, BeO, BaS, and CaSe. Preferred alkali metal halides include LiF, NaF, KF, LiCl, KCl, and NaCl. Preferred alkaline earth metal halides include fluorides or halides other than fluorides, such as CaF2, BaF2, SrF2, MgF2, and BeF2. Complexes of organic substances and metals can also be used suitably. When a complex of organic substances and metals is used in the electron injection layer, it is more preferable because the film thickness can be easily adjusted. Examples of such organometallic complexes include preferred examples of organic substances in the complex with an organic substance, such as quinolinol, benzoquinolinol, pyridylphenol, flavator, hydroxyimidazopyridine, hydroxyazaindene, and hydroxytriazole. Furthermore, metals may be used, for example, Li, Yb, Ba, and the like.

[0118] The method for forming each of the layers constituting the light-emitting device is not particularly limited and may be resistance heating deposition, electron beam deposition, sputtering, molecular lamination, coating, etc., but resistance heating deposition or electron beam deposition is usually preferred in terms of device characteristics.

[0119] The thickness of the organic layer is not limited because it depends on the resistance value of the light-emitting material, but is preferably 1 nm to 1000 nm. The thickness of each of the light-emitting layer, the electron transport layer, and the hole transport layer is preferably 1 nm to 200 nm, more preferably 5 nm to 100 nm.

[0120] The light-emitting element of the present invention has a function of converting electric energy into light. Here, the electric energy mainly uses a direct current, but a pulse current or an alternating current may also be used. The current value and the voltage value are not particularly limited, but should be selected so that the maximum brightness can be obtained with the lowest possible energy, taking into consideration the power consumption and lifespan of the element.

[0121] The light-emitting element of the present invention can also be suitably used as a backlight for various devices. Backlights are primarily intended to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, the light-emitting element of the present invention is preferably used as a backlight for liquid crystal display devices (particularly for personal computers, for which thinning is being considered), and can provide a backlight that is thinner and lighter than conventional backlights. EXAMPLES

[0122] The present invention will be described below with reference to examples, but the present invention is not limited to these.

[0123] The materials used in the examples and comparative examples are shown below.

[0124] Toluene, xylene, methanol, etc. were purchased from Sinopharm, triazine compounds were purchased from TCI, fluoranthene compounds were purchased from alfa-aeser, and various catalysts, etc. were purchased from Aldrich.

[0125] Synthesis Example 1 Synthesis of compound [6]

[0126] [ka]

[0127] 2.67g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 3.5g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine as a white solid.

[0128] 3.5g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 7 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 4.68g of yellow solid compound [6] (purity 99.9%).

[0129] Synthesis Example 2 Synthesis of compound [7]

[0130] [ka]

[0131] 3.00g of 2-(4-p-biphenyl)-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 1.22g of bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.2g of white solid 2-(4-p-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine.

[0132] 3.2g of 2-(4-p-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 100ml of o-xylene to obtain 3.82g of 2-(4-p-biphenyl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine as a white solid.

[0133] 3.82g of 2-(4-p-biphenyl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine, 2.3g of fluoranthene boronic acid, 0.12g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 50ml of methanol, and recrystallized from 100ml of o-xylene to obtain 5.21g of pale yellow solid compound [7] (purity 99.9%).

[0134] Synthesis Example 3 Synthesis of compound [8]

[0135] [ka]

[0136] 3.00g of 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. Then, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 1.22g of bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.2g of white solid 2-(4-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine.

[0137] 3.2g of 2-(4-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 80ml of o-xylene to obtain 3.78g of 2-(4-biphenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine as a white solid.

[0138] 3.78g of 2-(4-biphenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 2.3g of fluoranthene boronic acid, 0.12g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 50ml of methanol, and recrystallized from 80ml of o-xylene to obtain 5.00g of pale yellow solid compound [8] (purity 99.9%).

[0139] Synthesis Example 4 Synthesis of compound [9]

[0140] [ka]

[0141] 2.55g of 2-phenyl-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. After that, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 2.00g of m-bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.1g of white solid 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine.

[0142] 3.1g of 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5 triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 100ml of o-xylene to obtain 3.75g of 2-(4-phenyl)-4-(4-chlorophenyl)6-m-biphenyl-1,3,5 triazine as a white solid.

[0143] 3.75g of 2-(4-phenyl)-4-(4-chlorophenyl)6-m-biphenyl-1,3,5 triazine, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 4.94g (purity 99.9%) of pale yellow solid compound [9].

[0144] Synthesis Example 5 Synthesis of compound

[10]

[0145] [ka]

[0146] 2.55g of 2-phenyl-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. After that, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 2.00g of m-bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.1g of white solid 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine.

[0147] 3.1g of 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5 triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 80ml of o-xylene to obtain 3.83g of 2-(4-phenyl)-4-(3-chlorophenyl)-6-m-biphenyl-1,3,5 triazine as a white solid.

[0148] 3.83g of 2-(4-phenyl)-4-(3-chlorophenyl)-6-m-biphenyl-1,3,5-triazine, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 8 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 50ml of methanol, and recrystallized from 80ml of o-xylene to obtain 5.11g (99.9% purity) of pale yellow solid compound

[10] .

[0149] Synthesis Example 6 Synthesis of compound

[18]

[0150] [ka]

[0151] 2.67g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 3.5g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine as a white solid.

[0152] 3.5g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.1g of 4-chloro-4'-(4,6-diphenyl-1,3,5-triazine group)biphenyl as a white solid.

[0153] A flask was charged with 4.1g of 4-chloro-4'-(4,6-diphenyl-1,3,5-triazine group)biphenyl, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 5.82g (99.9% purity) of pale yellow solid compound

[18] .

[0154] Synthesis Example 7 Synthesis of compound

[22]

[0155] [ka]

[0156] 2.67g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2.12g of 2-dibenzofuran boric acid, 0.06g of ditriphenylphosphine palladium dichloride, and 5.20g of potassium carbonate were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated xylene was poured in. The mixture was reacted with ice water for one hour. The mixture was allowed to warm to room temperature and then the reaction was continued for three hours. The solvent was spun dry, washed three times with 100ml of water, and recrystallized with 100ml of o-xylene to obtain 3.8g of 2-(4,6-diphenyl-1,3,5-triazine group)-dibenzofuran as a white solid.

[0157] 3.8g of 2-(4,6-diphenyl-1,3,5-triazine group)-dibenzofuran, 3.4g of N-bromosuccinimide, and 3.60g of potassium phosphate trihydrate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried and separated using a silica gel column (PE:EA=1:20), to obtain 4.2g of 2-(4,6-diphenyl-1,3,5-triazine group)-8-bromodibenzofuran as a white solid.

[0158] 4.2g of 2-(4,6-diphenyl-1,3,5-triazine group)-8-bromodibenzofuran, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated xylene was poured in. The temperature was raised to 150°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 200ml of methanol, and recrystallized from 100ml of o-xylene to obtain 5.13g of pale yellow solid compound

[22] (purity 99.9%).

[0159] Synthesis Example 8 Synthesis of compound

[25]

[0160] [ka]

[0161] 2.64g of 2-chloro-4,6-diphenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.4g of 2-(4-chlorophenyl)-4,6-diphenylpyrimidine as a white solid.

[0162] 3.4g of 2-(4-chlorophenyl)-4,6-diphenylpyrimidine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 70ml of o-xylene to obtain 4.0g of 4-chloro-4'-(4,6-diphenylpyrimidine)biphenyl as a white solid.

[0163] A flask was charged with 4.0g of 4-chloro-4'-(4,6-diphenylpyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 5.90g of pale yellow solid compound

[25] (purity 99.9%).

[0164] Synthesis Example 9 Synthesis of compound

[26]

[0165] [ka]

[0166] 2.64g of 4-chloro-2,6-diphenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.4g of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine as a white solid.

[0167] 3.4g of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 70ml of o-xylene to obtain 4.0g of 4-chloro-4'-(2,6-diphenylpyrimidine)biphenyl as a white solid.

[0168] A flask was charged with 4.0 g of 4-chloro-4'-(2,6-diphenylpyrimidine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 5.90 g of pale yellow solid compound

[26] (purity 99.9%).

[0169] Synthesis Example 10 Synthesis of compound

[28]

[0170] [ka]

[0171] 2.9g of 2,6-diphenyl-4-chloropyridine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried and washed twice with 100ml of water to obtain 3.4g of 4-(2,6-diphenylpyridyl)chlorobenzene as a white solid.

[0172] 3.4g of 4-(2,6-diphenylpyridyl)chlorobenzene, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for one hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and washed three times with 100ml of methanol, to obtain 4.0g of 4-chloro-4'-(2,6-diphenylpyridyl)biphenyl, a white solid.

[0173] A flask was charged with 4.0 g of 4-chloro-4'-(2,6-diphenylpyridyl)biphenyl, 2.1 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for four hours. After cooling to room temperature, the solvent was removed by rotary drying, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 100 ml of o-xylene to obtain 5.45 g of pale yellow solid compound

[28] (purity 99.9%).

[0174] Synthesis Example 11 Synthesis of compound

[30]

[0175] [ka]

[0176] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized from 50 ml of o-xylene to obtain 4.60 g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine as a white solid.

[0177] A flask was charged with 4.60 g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.8 g of 4-chloro-3'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl as a white solid.

[0178] A flask was charged with 4.8g of 4-chloro-3'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 6.10g of pale yellow solid compound

[30] (purity 99.9%).

[0179] Synthesis Example 12 Synthesis of compound

[37]

[0180] [ka]

[0181] 2.55g of 2-phenyl-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. After that, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 2.00g of m-bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.1g of white solid 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine.

[0182] 3.1g of 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine, 1.21g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 3.9g of 2-(3-chlorophenyl)-4-phenyl-6-m-biphenyl-1,3,5-triazine as a white solid.

[0183] 3.9g of 2-(3-chlorophenyl)-4-phenyl-6-m-biphenyl-1,3,5-triazine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 5.0g of 3-chloro-3'-(4-phenyl-6-m-biphenyl-1,3,5-triazine)biphenyl as a white solid.

[0184] 5.0g of 3-chloro-3'-(4-phenyl-6-m-biphenyl-1,3,5-triazine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 2 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 6.3g of pale yellow solid compound

[37] (purity 99.9%).

[0185] Synthesis Example 13 Synthesis of compound

[38]

[0186] [ka]

[0187] 2.64g of 4-chloro-2,6-diphenylpyrimidine, 1.22g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.4g of 4-(3-chlorophenyl)-2,6-diphenylpyrimidine as a white solid.

[0188] 3.4g of 4-(3-chlorophenyl)-2,6-diphenylpyrimidine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 70ml of o-xylene to obtain 4.0g of 3-chloro-3'-(2,6-diphenylpyrimidine)biphenyl as a white solid.

[0189] A flask was charged with 4.0 g of 3-chloro-3'-(2,6-diphenylpyrimidine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 5.78 g of pale yellow solid compound

[38] (purity 99.9%).

[0190] Synthesis Example 14 Synthesis of compound

[39]

[0191] [ka]

[0192] 2.64g of 2-chloro-4,6-diphenylpyrimidine, 1.22g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.4g of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine as a white solid.

[0193] 3.4g of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 70ml of o-xylene to obtain 4.0g of 3-chloro-3'-(4,6-diphenylpyrimidine)biphenyl as a white solid.

[0194] A flask was charged with 4.0 g of 3-chloro-3'-(4,6-diphenylpyrimidine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 5.92 g of pale yellow solid compound

[39] (purity 99.9%).

[0195] Synthesis Example 15 Synthesis of compound

[43]

[0196] [ka]

[0197] 2.67g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 80°C and reacted for 24 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.2g of 2-(2-chlorophenyl)-4,6-diphenylpyrimidine as a white solid.

[0198] 3.2g of 2-(2-chlorophenyl)-4,6-diphenylpyrimidine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 70ml of o-xylene to obtain 3.8g of 3-chloro-2'-(4,6-diphenylpyrimidine)biphenyl as a white solid.

[0199] 3.8g of 3-chloro-2'-(4,6-diphenylpyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 5.65g of pale yellow solid compound

[43] (purity 99.9%).

[0200] Synthesis Example 16 Synthesis of compound

[61]

[0201] [ka]

[0202] 3.00g of 2-(4-p-biphenyl)-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 1.22g of bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.2g of white solid 2-(4-p-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine.

[0203] 3.2g of 2-(4-p-biphenylyl)-4-chloro-6-phenyl-1,3,5-triazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 100ml of o-xylene to obtain 4.0g of 2-(4-chlorophenyl)-4-p-biphenyl-6-phenyl-1,3,5-triazine as a white solid.

[0204] A flask was charged with 4.0 g of 2-(4-chlorophenyl)-4-p-biphenyl-6-phenyl-1,3,5-triazine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 100 ml of o-xylene to obtain 4.8 g of 4-chloro-4'-(4-p-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl as a white solid.

[0205] A flask was charged with 4.8g of 4-chloro-4'-(4-p-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 200ml of o-xylene to obtain 6.4g of pale yellow solid compound

[61] (purity 99.9%).

[0206] Synthesis Example 17 Synthesis of compound

[62]

[0207] [ka]

[0208] 2.55g of 2-phenyl-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. After that, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 2.00g of m-bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 3.1g of white solid 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine.

[0209] 3.1g of 2-(4-phenyl)-4-chloro-6-m-biphenyl-1,3,5-triazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 3.9g of 2-(4-chlorophenyl)-4-m-biphenyl-6-phenyl-1,3,5-triazine as a white solid.

[0210] 3.9g of 2-(4-chlorophenyl)-4-m-biphenyl-6-phenyl-1,3,5-triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.8g of white solid 4-chloro-4'-(4-m-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl.

[0211] A flask was charged with 4.8g of 4-chloro-4'-(4-m-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 6.5g of pale yellow solid compound

[62] (purity 99.9%).

[0212] Synthesis Example 18 Synthesis of compound

[63]

[0213] [ka]

[0214] 2.55g of 2-phenyl-4,6-dichloro-1,3,5-triazine and 0.24g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was replaced with argon gas three times. After that, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 2.00g of o-bromobenzene dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was spun dry to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:30) to obtain 3.0g of white solid 2-(4-phenyl)-4-chloro-6-o-biphenyl-1,3,5-triazine.

[0215] 3.0g of 2-(4-phenyl)-4-chloro-6-o-biphenyl-1,3,5-triazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 40ml of o-xylene to obtain 3.7g of 2-(4-chlorophenyl)-4-o-biphenyl-6-phenyl-1,3,5-triazine as a white solid.

[0216] 3.7g of 2-(4-chlorophenyl)-4-o-biphenyl-6-phenyl-1,3,5-triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.5g of 4-chloro-4'-(4-o-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl as a white solid.

[0217] A flask was charged with 4.5g of 4-chloro-4'-(4-o-biphenylyl-6-phenyl-1,3,5-triazinyl)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was spun dry, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 6.1g of pale yellow solid compound

[63] (purity 99.9%).

[0218] Synthesis Example 19 Synthesis of compound

[0106]

[0219] [ka]

[0220] 1.82g of 1,3,5-trichlorotriazine and 0.48g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was purged with argon gas three times. Then, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 5.0g of 3-bromodibenzofuran dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was rotary dried to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 4.0g of a white solid bisdibenzofuran substituted product.

[0221] A flask was charged with 4.0 g of bisdibenzofuran substituted product, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the mixture was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 100 ml of o-xylene to obtain 5.1 g of 2-(4-chlorophenyl)-4,6-bisdibenzofuran-1,3,5-triazine as a white solid.

[0222] A flask was charged with 5.1 g of 2-(4-chlorophenyl)-4,6-bisdibenzofuran-1,3,5-triazine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 100 ml of o-xylene to obtain 5.7 g of 4-chloro-4'-(4,6-bisdibenzofuran-1,3,5-triazine group)biphenyl as a white solid.

[0223] A flask was charged with 5.7g of 4-chloro-4'-(4,6-bisdibenzofuran-1,3,5-triazine group)biphenyl, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 200ml of o-xylene to obtain 6.5g of pale yellow solid compound

[0106] (purity 99.9%).

[0224] Synthesis Example 20 Synthesis of compound

[0110]

[0225] [ka]

[0226] 1.82g of 1,3,5-trichlorotriazine and 0.48g of magnesium block activated with hydrochloric acid were added to the flask, and the mixture was purged with argon gas three times. Then, dehydrated and deoxygenated toluene was poured in and stirred for 20 minutes. 5.0g of 3-bromodibenzofuran dissolved in toluene was added and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature and cold water was added to quench the reaction. The reaction product was then extracted with toluene, and the salt in the reaction product was further extracted with water. The organic phase was rotary dried to obtain a solid. The mixture was separated using a silica gel column (PE:EA=1:10) to obtain 4.0g of a white solid bisdibenzofuran substituted product.

[0227] A flask was charged with 4.0 g of bisdibenzofuran substituted product, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the mixture was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 50 ml of o-xylene to obtain 5.2 g of 2-(3-chlorophenyl)-4,6-bisdibenzofuran-1,3,5-triazine as a white solid.

[0228] A flask was charged with 5.2g of 2-(3-chlorophenyl)-4,6-bisdibenzofuran-1,3,5-triazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 5.8g of 3-chloro-3'-(4,6-bisdibenzofuran-1,3,5-triazine group)biphenyl as a white solid.

[0229] 5.8g of 3-chloro-3'-(4,6-bisdibenzofuran-1,3,5-triazine group)biphenyl, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 6.5g of pale yellow solid compound

[0110] (purity 99.9%).

[0230] Synthesis Example 21 Synthesis of compound

[0111]

[0231] [ka]

[0232] 2.7g of 3,5-dibromochlorobenzene, 5.0g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 7.20g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed three times with 200ml of methanol, and recrystallized from 100ml of o-xylene to obtain 5.0g of yellow solid compound 3,5-difluoranthene chlorobenzene.

[0233] 5.0g of 1,3-difluoranthene-5-chlorobenzene, 2.33g of 1,3-diphenyl-5-boronic acid triazine, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 5 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed twice with 100ml of methanol, and recrystallized from 70ml of o-xylene to obtain 6.5g of pale yellow solid compound

[0111] (purity 99.9%).

[0234] Synthesis Example 22 Synthesis of compound

[0112]

[0235] [ka]

[0236] 3.46g of 2,4,6-tribromochlorobenzene, 7.5g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 10.0g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed three times with 200ml of methanol, and recrystallized from 200ml of o-xylene to obtain 7.1g of yellow solid compound 2,4,6-trifluoranthene chlorobenzene.

[0237] 7.1g of 2,4,6-trifluoranthene chlorobenzene, 2.33g of 1,3-diphenyl-5-boronic acid triazine, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 5 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed twice with 100ml of methanol, and recrystallized from 300ml of o-xylene to obtain 8.0g of yellow solid compound

[0112] (purity 99.9%).

[0238] Synthesis Example 23 Synthesis of compound

[0113]

[0239] [ka]

[0240] 2.7g of 3,5-dibromochlorobenzene, 4.66g of 1,3-diphenyl-5-boronic acid triazine, 0.06g of ditriphenylphosphine palladium dichloride, and 5.0g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 4 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed three times with 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 5.5g of white solid compound 3,5-bis(3,5-diphenyltriazinyl)chlorobenzene.

[0241] 5.5g of 3,5-bis(3,5-diphenyltriazinyl)chlorobenzene, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, washed three times with 100ml of methanol, and recrystallized from 200ml of o-xylene to obtain 6.2g of 1-(4-chlorophenyl)-3,5-bis(1,3-diphenyltriazinyl)benzene as a white solid.

[0242] 6.2g of 1-(4-chlorophenyl)-3,5-bis(1,3-diphenyltriazinyl)benzene, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 500ml of o-xylene to obtain 8.0g of white solid compound

[0113] (purity 99.9%).

[0243] Synthesis Example 24 Synthesis of compound

[0114]

[0244] [ka]

[0245] 2.8g of 3,5-diphenylchlorobenzene, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried and washed with 100ml of water three times to obtain 3.4g of 2-(4-chlorophenyl)4,6-diphenylbenzene as a white solid.

[0246] 3.4g of 2-(4-chlorophenyl)4,6-diphenylbenzene, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.0g of 4-chloro-4'-(4,6-diphenylbenzene)biphenyl as a white solid.

[0247] A flask was charged with 4.0g of 4-chloro-4'-(4,6-diphenylbenzene)biphenyl, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for four hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 300ml of methanol, and recrystallized from 6000ml of o-xylene to obtain 5.31g (purity 99.9%) of pale yellow solid compound

[0114] .

[0248] Synthesis Example 25 Synthesis of compound

[0115]

[0249] [ka]

[0250] 3.4g of 1-(4-chlorophenyl)-3-p-biphenylyl-2,4,5,6-tetrazine, 1.56g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.1g of 4-chloro-4'-(1-3-p-biphenyl-2,4,5,6-tetrazinyl)biphenyl as a white solid.

[0251] 4.1g of 4-chloro-4'-(1-3-p-biphenyl-2,4,5,6-tetrazinyl)biphenyl, 2.1g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was spun dry, washed four times with 100ml of water and 100ml of methanol, and recrystallized from 100ml of o-xylene to obtain 3.13g of pale yellow solid compound

[0115] (purity 99.9%).

[0252] Synthesis Example 26 Synthesis of compound

[0138]

[0253] [ka]

[0254] 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltriazine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.63g of 2-([1,1'-biphenyl]4-yl)-4-(2-chlorophenyl)-6-phenyltriazine as a white solid.

[0255] A flask was charged with 4.63 g of 2-([1,1'-biphenyl]4-yl)-4-(2-chlorophenyl)-6-phenyltriazine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.7 g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-triazine)biphenyl as a white solid.

[0256] A flask was charged with 4.7g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-triazine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 3.25g of pale yellow solid compound

[0138] (purity 99.9%).

[0257] Synthesis Example 27 Synthesis of compound

[0139]

[0258] [ka]

[0259] A flask was charged with 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate, and the mixture was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.61g of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0260] A flask was charged with 4.61 g of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0261] A flask was charged with 4.6g of 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized with 120ml of o-xylene to obtain 3.24g (purity 99.9%) of pale yellow solid compound

[0139] .

[0262] Synthesis Example 28 Synthesis of compound

[0140]

[0263] [ka]

[0264] A flask was charged with 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate, and the mixture was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.65g of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenylpyrimidine as a white solid.

[0265] A flask was charged with 4.65 g of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.7 g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl as a white solid.

[0266] A flask was charged with 4.7g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized with 120ml of o-xylene to obtain 4.56g of pale yellow solid compound

[0140] (purity 99.9%).

[0267] Synthesis Example 29 Synthesis of compound

[0141]

[0268] [ka]

[0269] 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltriazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.50g of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyltriazine as a white solid.

[0270] A flask was charged with 4.50 g of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyltriazine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-triazine)biphenyl as a white solid.

[0271] A flask was charged with 4.6g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-triazine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized with 120ml of o-xylene to obtain 3.20g (purity 99.9%) of pale yellow solid compound

[0141] .

[0272] Synthesis Example 30 Synthesis of compound

[0142]

[0273] [ka]

[0274] A flask was charged with 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.41g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0275] A flask was charged with 4.41 g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0276] A flask was charged with 4.6g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized with 120ml of o-xylene to obtain 3.10g (purity 99.9%) of pale yellow solid compound

[0142] .

[0277] Synthesis Example 31 Synthesis of compound

[0143]

[0278] [ka]

[0279] 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 4.50g of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenylpyrimidine as a white solid.

[0280] A flask was charged with 4.50 g of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenylpyrimidine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.41 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl as a white solid.

[0281] 4.41g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 3.08g (purity 99.9%) of pale yellow solid compound

[0143] .

[0282] Synthesis Example 32 Synthesis of compound

[0183]

[0283] [ka]

[0284] 3.50g of 2,6-diphenyl-4-chlorotriazine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 4.53g of 2,6-diphenyl-4-(2-chlorophenyl)triazine as a white solid.

[0285] A flask was charged with 4.53 g of 2,6-diphenyl-4-(2-chlorophenyl)triazine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.61 g of 4-chloro-2'-(2,6-diphenyltriazine group)biphenyl as a white solid.

[0286] A flask was charged with 4.61g of 4-chloro-2'-(2,6-diphenyltriazine group)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized with 120ml of o-xylene to obtain 3.46g (purity 99.9%) of pale yellow solid compound

[0183] .

[0287] Synthesis Example 33 Synthesis of compound

[0186]

[0288] [ka]

[0289] 3.50g of 2,6-diphenyl-4-chlorotriazine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 4.30g of 2,6-diphenyl-4-(4-chlorophenyl)triazine as a white solid.

[0290] A flask was charged with 4.30 g of 2,6-diphenyl-4-(4-chlorophenyl)triazine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.50 g of 2-chloro-4'-(2,6-diphenyl-4-yl-triazine)biphenyl as a white solid.

[0291] 4.50g of 2-chloro-4'-(2,6-diphenyl-4-yl-triazine)biphenyl, 2.2g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 3.10g (purity 99.9%) of pale yellow solid compound

[0186] .

[0292] Synthesis Example 34 Synthesis of compound

[0148]

[0293] [ka]

[0294] 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of o-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 4.61g of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0295] A flask was charged with 4.61 g of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0296] A flask was charged with 4.6 g of 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 3.01 g of 4-(4-chlorophenyl)-3'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0297] 3.01g of 4-(4-chlorophenyl)-3'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.0g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 2.11g of pale yellow solid compound

[0148] (purity 99.9%).

[0298] Synthesis Example 35 Synthesis of compound

[0151]

[0299] [ka]

[0300] 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.41g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0301] A flask was charged with 4.41 g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0302] A flask was charged with 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 2.54 g of 2-(4-chlorophenyl)-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0303] 2.54g of 2-(4-chlorophenyl)-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the flask was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 1.02g (purity 99.9%) of pale yellow solid compound

[0151] .

[0304] Synthesis Example 36 Synthesis of compound

[0154]

[0305] [ka]

[0306] 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of p-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 4.41g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0307] A flask was charged with 4.41 g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.6 g of 4-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl as a white solid.

[0308] A flask was charged with 4.6 g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphinepalladium dichloride, and 3.60 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized from 70 ml of o-xylene to obtain 3.12 g of 2''-chloro-4-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)terphenyl as a white solid.

[0309] 3.12g of 2''-chloro-4-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine) terphenyl, 2.0g of fluoranthene boronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.6g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water and 100ml of methanol, and recrystallized from 120ml of o-xylene to obtain 1.20g of pale yellow solid compound

[0154] (purity 99.9%).

[0310] Synthesis Example 37 Synthesis of compound

[34]

[0311] [ka]

[0312] 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltriazine, 1.22g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized from 50ml of o-xylene to obtain 3.50g of 2-([1,1'-biphenyl]4-yl)-4-(3-chlorophenyl)-6-phenyltriazine as a white solid.

[0313] 3.50g of 2-([1,1'-biphenyl]4-yl)-4-(3-chlorophenyl)-6-phenyltriazine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.2g of 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenyltriazine)biphenyl as a white solid.

[0314] A flask was charged with 4.2 g of 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenyltriazine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was removed by rotary drying, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 4.73 g of pale yellow solid compound

[34] (purity 99.9%).

[0315] Synthesis Example 38 Synthesis of compound

[40]

[0316] [ka]

[0317] 3.67g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 3.70g of 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine as a white solid.

[0318] A flask was charged with 3.70 g of white solid 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water, and recrystallized with 70 ml of o-xylene to obtain 4.10 g of white solid 3-chloro-3'-(4-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine)biphenyl.

[0319] A flask was charged with 4.10 g of 3-chloro-3'-(4-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was then poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was removed by rotary drying, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 4.31 g of pale yellow solid compound

[40] (purity 99.9%).

[0320] Synthesis Example 39 Synthesis of compound

[41]

[0321] [ka]

[0322] 3.67g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphine palladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the mixture was replaced with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 50ml of o-xylene to obtain 3.69g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine as a white solid.

[0323] 3.69g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine, 1.56g of m-chlorophenylboronic acid, 0.06g of ditriphenylphosphinepalladium dichloride, and 3.60g of potassium carbonate were added to a flask, and the flask was purged with argon gas three times, after which dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 1 hour. After cooling to room temperature, the solvent was rotary dried, washed three times with 100ml of water, and recrystallized with 70ml of o-xylene to obtain 4.02g of 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine)biphenyl as a white solid.

[0324] A flask was charged with 4.02 g of white solid 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine)biphenyl, 2.2 g of fluoranthene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate. The flask was then purged with argon gas three times, and dehydrated and deoxygenated toluene was poured in. The temperature was raised to 120°C and the reaction was carried out for 12 hours. After cooling to room temperature, the solvent was rotary dried, washed three times with 100 ml of water and 100 ml of methanol, and recrystallized from 120 ml of o-xylene to obtain 3.90 g of pale yellow solid compound

[41] (purity 99.9%).

[0325] Example 1 A glass substrate (Geomatec Corporation, 11 Ω / □, sputtered product) on which a 165 nm ITO transparent conductive film had been deposited was cut to 38 mm × 46 mm and etched. The resulting substrate was ultrasonically cleaned for 15 minutes using "Semico Clean 56" (product name, Furuuchi Chemical Corporation), and then washed with ultrapure water. Before fabricating the element, the substrate was treated with ultraviolet (UV)-ozone for 1 hour, placed in a vacuum deposition apparatus, and the degree of vacuum in the apparatus was 5 × 10 -4 The chamber was evacuated until the pressure reached 75 Pa or less. First, 75 nm of HAT-CN6 was deposited as a hole injection layer and 42.5 nm of HT-1 was deposited as a hole transport layer by resistance heating. Then, the host material H-1 and the dopant material D-1 were deposited to a thickness of 20 nm so that the doping concentration was 5% by weight, forming an emission layer. Compound [6] was then deposited to a thickness of 30 nm to form an electron transport layer. After that, 1 nm of Yb was deposited, and 15 nm of Mg / Aa (1:9) was deposited as a cathode to produce a 5 mm x 5 mm square element. The film thickness referred to here is the value displayed by a quartz crystal oscillation film thickness monitor (Conltaec's Eon LT). The 10 mA / cm thickness of this light-emitting element was 2 The characteristics at this temperature were a driving voltage of 4.51 V and an efficiency of 6.6 cd / A. The initial luminance was 10 mA / cm 2When the device was driven at a constant current and set at 1,600 hours, the brightness half-life was 1600 hours, at which the brightness decreased by 50%. The above-mentioned HAT-CN 6, HT-1, H-1, and D-1 are the compounds shown below. A device consisting of such a single light-emitting unit is called a single device to distinguish it from a tandem device consisting of one or more light-emitting units as shown below.

[0326] [ka]

[0327] Example 2 to Example 41 A light-emitting device was produced and evaluated in the same manner as in Example 1, except that a compound shown in Table 1 was used in the electron transport layer.

[0328] Comparative Examples 1 to 8 A light-emitting device was produced and evaluated in the same manner as in Example 1, except that the electron transport layer was formed using the compounds shown in Table 1. C-1 to C-7 and HB-1 are the compounds shown below.

[0329] [ka]

[0330] [ka]

[0331] Examples 42 to 45 A light-emitting element was prepared in the same manner as in Example 1, except that compound C-4 was used in the electron transport layer and compound HB-1 was used in the hole blocking layer. After preparing this light-emitting element, the compounds shown in Table 1 were vapor-deposited as compounds for the charge generating layer, and then a similar light-emitting element was vapor-deposited to prepare a tandem device and evaluate it.

[0332] Comparative Example 9 A light-emitting device was prepared in the same manner as in Example 1, except that compound C-4 was used for the electron transport layer and compound HB-1 was used for the hole blocking layer. After preparing this light-emitting device, Alq3 was vapor-deposited as a charge generation layer compound, and then a similar light-emitting device was vapor-deposited to prepare a tandem device and evaluate it.

[0333] [ka]

[0334] [Table 1]

[0335] Comparative Example 1 and Comparative Example 2 are commercially available fluoranthene and fluoranthene-based materials. Comparative Example 1 has a problem of high efficiency but short high voltage life. On the other hand, Comparative Example 2 has a long life but low efficiency. Comparative Example 3 and Comparative Example 4 are commercially available electron transport materials with leading levels, Comparative Example 3 has low voltage, high efficiency but short life. On the other hand, Comparative Example 4 has high efficiency, high voltage, and not long life. These devices have defects in performance, which may have a significant impact on practical applications. Comparative Example 5 and Comparative Example 6 are some fluoranthene-based materials that have been investigated, Comparative Example 5 has low voltage but low life and efficiency. In addition, Comparative Example 5 itself is unstable and may decompose during the sublimation process. It is difficult to make a device, and the rate of non-defective products decreases. Comparative Example 6 has a relatively long life, but the voltage is somewhat high and the efficiency is low, and the materials of Examples 1 to 31 are superior to Comparative Examples 1 to 6 in overall performance and showed better performance as devices.

[0336] Comparing Example 1, Example 21, and Example 22, it was found that when the fluoranthene group is reduced, the energy level transition of the molecular orbital becomes deeper, so that the matching with the electron injection layer material improves, the voltage decreases, and the lifespan also tends to increase. In particular, when one fluoranthene group is preferred, the voltage and lifespan are significantly improved. Also, when one fluoranthene group is preferred, it is easier to vapor-deposit the material.

[0337] By comparing Example 6 and Example 23, it can be seen that reducing the azabenzene group deepens the molecular orbital energy level transition, improving the matching with the electron injection layer material, lowering the voltage, and increasing the lifetime. In particular, when one azabenzene group is preferred, the voltage and lifetime are significantly improved. Also, when one azabenzene group is preferred, the deposition of the material is easier. This trend is similar to that of the fluoranthene group, but the reduction of the azabenzene group has a stronger degree of optimization for device effects than fluoranthene.

[0338] By comparing Example 6, Example 9, Example 10, Example 24, and Example 25, when the azabenzine host contains a nitrogen atom, the supply of electrons increases, improving the number of electrons in the entire molecule and improving the device efficiency. When there is no nitrogen in the center of the azobenzene host, the efficiency is very low, and when there is one nitrogen, the efficiency is higher than when there is no nitrogen at all, but it is still at a level that does not have a significant advantage. When there are four nitrogens, the energy level is too deep and the voltage is too high. Preferably, when the center of the aza body contains two nitrogen atoms (pyrimidine) or three nitrogen atoms (triazine), the efficiency can be improved while maintaining a low voltage and achieving a good balance between the two. When there are two nitrogens in the center, the efficiency is higher, and when there are three nitrogens, the life is longer. This tendency was also observed in Examples 26 to 31.

[0339] Comparing Examples 11 to 14 with Comparative Example 7, when diphenyltriazine and fluoranthene are connected with two m-phenylene groups, none of the voltage, efficiency, and lifespan are favorable. However, by changing the azabenzine host to a pyrimidine and / or the phenyl group to a biphenyl group, the voltage can be reduced and the efficiency and lifespan can be improved.

[0340] By comparing Examples 6, 16, and 26 to 31, it can be seen that by introducing adjacent benzene into the molecule, the distance between the fluoranthene host and the azobenzene host can be shortened, and the electronic processing ability can be enhanced, thereby improving the electrical properties, reducing the voltage, improving the efficiency, and the effect is very significant.

[0341] By comparing Example 6 with Example 16, it can be seen that when the substituents of the azabenzene host are benzene and biphenyl, the efficiency and lifespan can be improved compared to two benzenes, but the voltage is slightly improved. In addition, the compound used in Example 6 is more symmetrical in the azabenzene host, so it is easy to block holes during deposition, resulting in a lower yield rate and a lower production tact. On the other hand, Example 16, which improves the asymmetry of the azabenzine host, showed a better production tact. Furthermore, by comparing Examples 26, 29, 32, and 33, it can be seen that after introducing ortho-substituents to further strengthen the electronic processing ability, the azabenzine host substituted with benzene and biphenyl further reduces the voltage, improves the efficiency, and improves the lifespan, but the increase in the bisbenzene material is small. In addition to the compatibility with the surrounding materials, the space exclusion effect of biphenyl restricts the rotation of the azabenzine host, thereby strengthening the stability of the large delocalized π electrons and strengthening the electronic processing performance, which is also an important cause.

[0342] Comparing Examples 16 and 18 with Comparative Example 5, it can be seen that when a nitrogen-containing substituted azabenzene host is used, the energy level is adjusted excessively, resulting in a mismatch with the surrounding layer materials, resulting in a decrease in efficiency.

[0343] By comparing Examples 16 and 18 with Comparative Example 6, it can be seen that when a fused ring is linked to an azobenzene-based host, the fused ring disrupts the regular electron transfer by fluoranthene, reducing the electron processing ability of the molecule and improving the voltage reduction efficiency.

[0344] As can be seen by comparing Examples 29-31 with Examples 34-36, increasing the length of the benzene rings in L1 and L2 increases the length of the π electron system, further improving performance.

[0345] Comparing Examples 37 to 41 with Comparative Examples 4 and 8, it can be seen that the fluoranthene-based compounds provided by the present invention are specialized for electrons, and therefore have reduced hole-processing ability. When used as a hole-blocking layer, they can effectively block the passage of holes, improve efficiency, and extend life, compared with the general hole-blocking material HB-1 and compound C7.

[0346] Comparing Examples 42-45 with Comparative Example 9, it can be seen that even when the fluoranthene-based compound of the present invention is used as a charge generation layer material, it is possible to achieve a lower voltage, higher efficiency, and longer life than the general charge generation layer material Alq3. However, it is pointed out that the device is not a combination of the properties of each material layer linearly superimposed, but a combination of multiple material layers. Therefore, when the surrounding materials change, some electron transport layer materials are accordingly optimal. Thus, the present invention provides a series of materials for tuning molecules for different practical devices.

Claims

1. A fluoranthene derivative represented by general formula (1) or the following formula 73, 74, 75, 150, 151, 152, 168, 169 or 170. General formula (1) 【Chemical 1】 (L １ represents a substituted or unsubstituted arylene group, L ２ represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted heteroarylene group, provided that at least one of L 1 and L 2 is an o-phenylene group. X １ , X ２ , X ３ , X ４ , X ５ are the same or different, and each independently represents N or C-R １ However, among X 1 , X 2 , X 3 , X 4 and X 5 , the number of N is 2 or 3, X 2 is C-(Ph)n5, X 4 is C-(Ph)n6, Ph is a phenyl group, and n5+n6>2. R １ are each independently selected from one or more of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted silanyl group, a substituted or unsubstituted alkylamino group, or a substituted or unsubstituted arylamino. n1 and n4 are integers from 1 to 3. n2 and n3 are integers from 0 to 3. However, they cannot both be 0.) 【Chemistry 2】

2. 2. The fluoranthene derivative according to claim 1, wherein n1=1 and n4=1 in the general formula (1).

3. 2. The fluoranthene derivative according to claim 1, wherein in the general formula (1), when n1=1, the value of n1×n2+n3×n4 is an integer of 1 to 5.

4. 2. The fluoranthene derivative according to claim 1, wherein in the general formula (1), when n1=1, the value of n1×n2+n3×n4 is an integer of 2 or 3.

5. C-R １ R １ 2. The fluoranthene derivative according to claim 1, wherein is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzothiophene, and a substituted or unsubstituted fluorene.

6. 2. The fluoranthene derivative according to claim 1, wherein n5≠n6.

7. L １ and L ２ are each independently selected from a phenylene group (provided that L １ and L ２ and are not simultaneously an m-phenylene group.

8. 2. The fluoranthene derivative according to claim 1, wherein the fluoranthene derivative is selected from the following compounds in the general formula (1): 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】

9. A light-emitting device, comprising an organic layer between an anode and a cathode, the organic layer being responsible for emitting light and / or processing electrons or holes, and the organic layer comprising the fluoranthene derivative according to any one of claims 1 to 8.

10. 10. The light-emitting device according to claim 9, wherein the organic layer is a layer that processes electrons or holes, and the organic layer contains the fluoranthene derivative according to any one of claims 1 to 8.

11. 10. The light-emitting device according to claim 9, wherein an electron transport layer is present in the organic layer, and the electron transport layer contains the fluoranthene derivative according to any one of claims 1 to 8.

12. 10. The light-emitting device according to claim 9, wherein an electron generating layer is present in the organic layer, and the electron generating layer contains the fluoranthene derivative according to any one of claims 1 to 8.

13. 10. The light-emitting device according to claim 9, wherein a hole-blocking layer is present in the organic layer, and the hole-blocking layer contains the fluoranthene derivative according to any one of claims 1 to 8.

14. A photoelectric conversion element comprising the fluoranthene derivative according to any one of claims 1 to 8.

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