Propylene oxygenate derivatives, light-emitting elements, and photoelectric conversion elements

Abstract

This invention provides a propylene pyroxene derivative, comprising a photoelectric conversion element and a light-emitting element. The propylene pyroxene derivative of this invention has a specific structure comprising a propylene pyroxene host and a azirbenzene host. According to this invention, an organic thin-film light-emitting element can be provided that simultaneously achieves high luminous efficiency, low driving voltage, and long lifespan.

Description

Propylene oxygenate derivatives, light-emitting elements, and photoelectric conversion elements This invention relates to light-emitting elements that can convert electrical energy into light and the materials used in such light-emitting elements. This invention can be applied in the fields of display elements, flat panel displays, backlights, lighting, interior decoration, signage, billboards, electronic cameras, virtual reality, augmented reality, smartwatches, mobile phones, laptops, tablets, displays, automotive displays, automotive taillights, televisions, and light signal generators. In recent years, research on organic thin-film light-emitting elements, also known as organic light-emitting diodes (OLEDs), has become increasingly active. These organic thin-film light-emitting elements emit light when electrons injected from the cathode and holes injected from the anode recombine within the organic light-emitting body sandwiched between the two electrodes. The characteristics of this light-emitting element are its small thickness and ability to emit light with high brightness at low driving voltage. It can also achieve multi-color emission by selecting light-emitting materials, and therefore has attracted much attention. Since the discovery by C.T. Tang et al. of Kodak that organic thin-film devices could emit light with high brightness, this research has led to extensive practical applications. Currently, OLEDs are widely used in wristbands, mobile phones, televisions, and other fields. However, many technical challenges remain, among which simultaneously achieving high efficiency and long lifespan for these devices is a major one. OLEDs must achieve improved luminous efficiency, reduced driving voltage, and increased durability. Achieving both luminous efficiency and durability simultaneously is a significant challenge. However, existing technologies (Patent Documents 1-6) struggle to sufficiently reduce the driving voltage of the device, and even when the driving voltage is reduced, the luminous efficiency and durability remain insufficient. As mentioned above, no technology has yet been found that can simultaneously achieve high luminous efficiency, low driving voltage, and high durability. [Prior Art Documents] [Patent Documents] [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. (The problem the invention aims to solve) The purpose of this invention is to solve the problems of the prior art described above, and to provide an organic thin-film light-emitting element with improved luminous efficiency, driving voltage, and lifespan. (Technical means to solve the problem) This invention controls the amount of electrons with transport capabilities in the molecule by adjusting the number and nitrogen content of the propylene pyroxene host and the azirmonide host in the propylene pyroxene derivative, thereby adjusting the luminous efficiency, driving voltage and durability. This invention provides a propadiene oxyacetate derivative having the structure shown in General Formula 1 below. [General Formula 1] Wherein, L1 is a substituted aryl group; L2 is a single bond, a substituted aryl group, or a substituted heteroaryl group; X1, X2, X3, X4, and X5 may be the same or different, and each is independently N or C-R1; wherein R1 is independently selected from hydrogen, deuterium, substituted alkyl, substituted cycloalkyl, substituted heterocyclic, substituted alkenyl, substituted cycloalkenyl, substituted alkynyl, substituted alkoxy, substituted alkylthio, substituted aryl ether, and substituted aryl thioether. One or more of the following: substituted aryl, substituted heteroaryl, substituted carbonyl, substituted carboxyl, substituted oxycarbonyl, substituted aminomethyl, substituted silyl, substituted alkylamine, or substituted arylamine; when X1, X3, and X5 are all N, X2 and X4 are all C-R1 and R1 is all phenyl, and L1 and L2 are both phenylene, at least one of L1 and L2 is selected from o-phenylene or para-phenylene; n1 and n4 are integers from 1 to 3; n2 and n3 are integers from 0 to 3. In addition, the present invention provides a light-emitting element having an organic layer between the anode and the cathode, wherein the organic layer contains the aforementioned propylene oxygenate derivative. In addition, the present invention discloses a photoelectric conversion element containing the aforementioned propylene oxygenate derivative. (Effectiveness compared to prior art) The present invention provides an organic thin-film light-emitting element that simultaneously achieves high luminous efficiency, low driving voltage, and long lifespan. The specific embodiments of the present invention will be described in detail below. First, the propylene oxyacetylene derivatives having the structure shown in general formula (1) provided by the present invention will be described in detail. [General Formula 1] Wherein, L1 is a substituted aryl group; L2 is a single bond, a substituted aryl group, or a substituted heteroaryl group; X1, X2, X3, X4, and X5 may be the same or different, and each is independently N or C-R1; wherein R1 is independently selected from hydrogen, deuterium, substituted alkyl, substituted cycloalkyl, substituted heterocyclic, substituted alkenyl, substituted cycloalkenyl, substituted alkynyl, substituted alkoxy, substituted alkylthio, substituted aryl ether, and substituted aryl thioether. One or more of the following: substituted aryl, substituted heteroaryl, substituted carbonyl, substituted carboxyl, substituted oxycarbonyl, substituted aminomethyl, substituted silyl, substituted alkylamine, or substituted arylamine; when X1, X3, and X5 are all N, X2 and X4 are all C-R1 and R1 is all phenyl, and L1 and L2 are both phenylene, at least one of L1 and L2 is selected from o-phenylene or para-phenylene; n1 and n4 are integers from 1 to 3; n2 and n3 are integers from 0 to 3. Among all the above groups, hydrogen can also be deuterium. In this document, when "substitutable" is used, the substituent is preferably a substituted alkyl group, a substituted cycloalkyl group, a substituted heterocyclic group, a substituted alkenyl group, a substituted cycloalkenyl group, a substituted alkynyl group, a substituted alkoxy group, a substituted alkylthio group, a substituted aryl ether group, a substituted aryl thioether group, a substituted aryl group, a substituted heteroaryl group, a substituted carbonyl group, a substituted carboxyl group, a substituted oxycarbonyl group, a substituted aminomethyl group, a substituted silyl group, a substituted alkylamine group or a substituted arylamine group, a halogen, a cyano group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an aminomethyl group, a phosphonyl group, a condensed aromatic hydrocarbon ring, a monocyclic aromatic heterocycle, and a condensed aromatic heterocycle, and further preferably, specific substituents are listed in the description of each substituent. Moreover, these substituents can be further replaced by the aforementioned substituents. The case of "not being replaced" in the context of "can be replaced" means that it is replaced by a hydrogen atom. The same applies to the "substitutable" situation in the compounds or parts thereof described below. The term "alkyl" refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tributyl, which may or may not have substituents. There are no particular restrictions on the additional substituents added when substituted; examples include alkyl, aryl, and heteroaryl groups, and this will be used consistently in the following description. Furthermore, there is no particular limitation on the number of carbon atoms in the alkyl group; however, considering the ease of obtaining materials and cost, a number of 1 to 20 carbon atoms is preferred. The term cycloalkyl refers to saturated aliphatic cycloalkyl groups such as cyclopropyl, cyclohexyl, noralkyl, and adamantyl, which may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkyl moiety; however, considering the ease of material availability and cost, a range of 3 to 20 carbon atoms is preferred. The term alkenyl refers to unsaturated aliphatic hydrocarbon groups containing double bonds, such as vinyl, allyl, and butadiene, which may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkenyl group; however, considering the ease of material availability and cost, a range of 3 to 20 carbon atoms is preferred. The term "cycloalkenyl" refers to unsaturated aliphatic hydrocarbon groups containing double bonds, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl. These groups may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkenyl group; however, considering the ease of obtaining materials and cost, a range of 3 to 20 carbon atoms is preferred. The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as ethynyl, which may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkenyl group; however, considering the ease of material availability and cost, a range of 3 to 20 carbon atoms is preferred. The term alkoxy refers to a functional group consisting of an aliphatic hydrocarbon group, such as methoxy, ethoxy, or propoxy, bonded via an ether bond. This aliphatic hydrocarbon group may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkoxy group; however, considering the ease of obtaining materials and cost, a range of 1 to 20 carbon atoms is preferred. An alkylthio group is formed by replacing the oxygen atom in the ether bond of an alkoxy group with a sulfur atom. The hydrocarbon group of an alkylthio group may or may not have substituents. There is no particular limitation on the number of carbon atoms in the alkylthio group, but considering the ease of obtaining materials and cost, a range of 1 to 20 is preferred. The term "aryl ether" refers to a functional group consisting of an aromatic hydrocarbon group, such as a phenoxy group, bonded via an ether bond. This aromatic hydrocarbon group may or may not have substituents. There is no particular limitation on the number of carbon atoms in the aryl ether group; however, considering the ease of obtaining materials and cost, a range of 6 to 40 carbon atoms is preferred. The term "aryl thioether" refers to an aryl ether group where the oxygen atom in the ether bond is replaced by a sulfur atom. The aromatic hydrocarbon group in an aryl thioether group may or may not have substituents. There is no particular limitation on the number of carbon atoms in the aryl thioether group; however, considering the ease of obtaining materials and cost, a range of 6 to 40 carbon atoms is preferred. The term "aryl" refers to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthryl, triphenyl, pyrene, and 1,2-benzoacenaphthene. Aryl groups may or may not have substituents. There is no particular limitation on the number of carbon atoms in an aryl group; however, considering the ease of obtaining materials and cost, a range of 6 to 40 carbon atoms is preferred. The term "heteroaryl" refers to cyclic aromatic groups such as furanyl, thiophenyl, pyridinyl, quinolinyl, isoquinolinyl, pyridyl, pyrimidinyl, naphthidyl, benzofuranyl, benzobenzenethio, indolyl, dibenzofuranyl, dibenzobenzenethio, and carbazoleyl, which have atoms other than carbon atoms in one or more rings. These groups can be unsubstituted or substituted. There is no particular limitation on the number of carbon atoms in a heteroaryl group; however, considering the ease of obtaining materials and cost, a range of 2 to 30 carbon atoms is preferred. The term halogen refers to an atom selected from fluorine, chlorine, bromine, and iodine. Carbonyl, carboxyl, oxycarbonyl, cyano, aminomethyl, and phosphine oxide groups may or may not have substituents. Examples of substituents include alkyl, cycloalkyl, aryl, and heteroaryl groups, which can be further substituted. The term "aryl" refers to a divalent or trivalent group derived from aromatic hydrocarbon groups such as phenyl, naphthyl, and biphenyl. It may or may not have substituents. When L1 of general formula 1 is an aryl group, the preferred number of carbon atoms is 6 or more and 24 or less, with 6 or more and 12 or less being even more preferred. Specific examples of aryl groups include: 1,4-elongylphenyl, 1,3-elongylphenyl, 1,2-elongylphenyl, 4,4′-elongyl-biphenyl, 4,3′-elongyl-biphenyl, 3,3′-elongyl-biphenyl, 1,4-elongyl-naphthyl, 1,5-elongyl-naphthyl, 2,5-elongyl-naphthyl, 2,6-elongyl-naphthyl, 2,7-elongyl-naphthyl, etc. 1,4-elongylphenyl and 1,3-elongylphenyl are even more preferred. The term "enthalpyrrolyl" refers to a divalent or trivalent substituent derived from an aromatic group such as pyridyl, quinolinyl, pyrimidinyl, pyridyl, naphthidyl, dibenzofuranyl, or dibenzophenylthioyl, which has atoms other than carbon atoms in one or more rings. It may or may not have substituents. The number of carbon atoms in the enthalpyrrolyl group is not particularly limited, but a range of 2 to 30 is preferred. Examples of condensed aromatic hydrocarbon rings include naphthalene rings, azurite rings, anthracene rings, phenanthrene rings, pyrene rings, 1,2-benzophenanthrene rings, fused tetraphenyl rings, triphenylbenzene rings, acenaphthene rings, cardamom rings, fenestration rings, 1,2-benzoacenaphthene rings, fused tetraphenyl rings, fused pentaphenyl rings, perylene rings, iso-fused pentaphenyl rings, picene rings, pyranthrene rings, and anthraanthrene rings. Furthermore, these condensed aromatic hydrocarbon rings may also have substituents. Monocyclic aromatic heterocycles can include, for example, furan rings, thiophene rings, pyridine rings, pyrazine rings, pyrimidine rings, pyrazine rings, triazole rings, diazole rings, triazole rings, imidazole rings, pyrazole rings, and thiazole rings. Furthermore, these monocyclic aromatic heterocycles may also have substituents. Examples of condensed aromatic heterocycles include quinoline rings, isoquinoline rings, quinoline rings, benzimidazole rings, indole rings, benzimidazole rings, benzothiazole rings, benzoxazole rings, quinoline rings, quinazolin rings, thiazoline rings, carbazole rings, carbline rings, and diazacarbazole rings (representing a ring in which a carbon atom of the hydrocarbon ring constituting the carbline ring is further replaced by a nitrogen atom). Furthermore, these condensed aromatic heterocycles may also have substituents. This invention provides a combined allene pyrenoid host and azirene host allene pyrenoid derivative. The allene pyrenoid structure consists of three benzene rings surrounding a cyclopentane group, allowing electrons to be delocalized throughout the entire allene pyrenoid structure. Conversely, the cyclopentane group forms electron voids, exhibiting a tendency to absorb electrons. The azirene host can be benzene or an azirene containing multiple nitrogen atoms. In the azirene group, the large π bond of benzene itself can move throughout the molecule. Adding nitrogen to the azirene host further increases the number of delocalized electrons in the large π bond, thereby enhancing electron transport capability. The electrons in the azirene host are less attracted to the atomic nucleus, while the allene pyrenoid group has a tendency to attract electrons, causing electrons to tend to move towards the allene pyrenoid group throughout the molecule (even though the molecule itself is neutral). When such molecules accumulate to form a film, they can, to some extent, mimic the electron delocalization in metallic bonds, thus providing electron transport capability. On the other hand, excessive propylene pyroxene hosts can disrupt electron flow and reduce efficient electron transport, while excessive nitrogen can excessively lower the LUMO, resulting in an energy level mismatch between the electron-processed material and the surrounding materials. Therefore, the number of propylene pyroxene hosts and aziridine hosts needs to be precisely controlled at the molecular level. Considering the energy level matching, electron processing capability, synthesis difficulty, and cost, the optimal scenario is a propylene pyroxene host quantity (n1) of 1 and an aziridine host quantity (n4) of 1. Research has shown that using fused-ring compounds such as naphthalene at the L2 position (the direct connection to the azirbenzene host) can easily disrupt the electrons provided by the azirbenzene host, thus reducing the molecule's electronic processing performance. Therefore, a non-fused-ring phenyl group is used at the L2 position. Research has shown that when n1=1 and the values ​​of n1×n2+n3×n4 are between 1 and 5, the energy levels of the molecules can match most common OLED systems on the market. Furthermore, when n1=1 and the value of n1×n2+n3×n4 is within 2-3, the number of delocalized electrons in the molecule reaches the optimal level, which can achieve the best device performance. As mentioned above, the number of nitrogen atoms in the azirbenzene matrix needs to be precisely controlled. Considering the energy levels of common materials adjacent to electronic processing materials and actual test results, X1, X2, X3, X4, and X5 exhibit better electronic processing performance when they contain 0-3 N atoms. In particular, better efficiency can be achieved when there are two N values ​​in X1, X2, X3, X4, and X5. In particular, when there are 3 Ns in X1, X2, X3, X4, and X5, the lifespan can be longer. By adding benzene-based aromatic substituents to the substituents of the azirbenzene host, the overall energy levels and electron-donating ability of the azirbenzene host can be fine-tuned, thereby achieving more precise control. Therefore, when X1, X2, X3, X4, and X5 are preferably C-R1, R1 is selected from substituted phenyl groups, substituted furanyl groups (e.g., preferably dibenzofuranyl groups), or substituted carbazoyl, fumonyl, or dibenzothiophene groups. In particular, when X2 is C-(Ph)n5, X4 is C-(Ph)n6, Ph is phenyl, and n5+n6>2, it can be most widely adapted to more peripheral layer materials and achieve the best results. When n5 and n6 are different, the productivity of molecules and the performance of vapor deposition can be improved. Research has revealed that when the azirbenzene host is triphenyl and has two benzene substituents, it is more suitable to transfer electrons to the propylene oxygenate host via para- or ortho-substituted L1 and L2, based on its electron-donating ability. Therefore, when X1, X3, and X5 in the azirbenzene host are all N, X2 and X4 are both C-R1 with R1 being phenyl, and L1 and L2 are phenylene, at least one of L1 and L2 must be selected from ortho- or para-phenylene. It should be clarified that when the connecting portions L1 and L2 are selected from phenyl groups, electrons can be transferred more effectively from the azirbenzene host to the propylene pyroxene host. However, when both L1 and L2 are selected from meta-phenyl groups, electron transport is hindered due to bending; furthermore, the azirbenzene host and the propylene pyroxene host are too far apart, resulting in a lack of spatial interaction and an overall decrease in transport capability. Therefore, when this propylene pyroxene derivative is used as an electron transport layer material, L1 and L2 should not both be meta-phenyl groups. In particular, o-phenyl groups not only allow the azirbenzene host to approach the propylene oxygenate host, but also improve molecular orientation, further achieving low-voltage, high-efficiency performance. Therefore, it is preferable that at least one of L1 and L2 is an o-phenyl group. In particular, when at least one of L1 and L2 is an o-phenyl group, the substituents of the azirbenzene host exhibit better electrical performance than the biphenyl plus benzene structure. This is because the steric exclusion effect of biphenyl restricts the rotation of the azirbenzene host, thereby strengthening the stability of the delocalized large π bond and enhancing electronic processing performance. It is worth noting that when nitrogen-containing substituents (such as pyridine or pyrimidine) are added to the substituents of the azirbenzene host, the energy levels of the two azirbenzene hosts become too low, resulting in a mismatch with the surrounding materials. On the other hand, when the azirbenzene host is replaced by a nitrogen-containing substituent, the chemical bonds between them have very low electron cloud density due to the electrons being withdrawn by each of the two azirbenzene hosts, making them prone to breakage. Therefore, it is not recommended to select nitrogen-containing substituents for the azirbenzene host. Through practice, we believe that the following molecular structures and their derivatives can achieve excellent overall performance in terms of efficiency, voltage, and lifetime, depending on the specific device structure and application. Therefore, the following compounds are preferred: . The present invention also discloses a light-emitting element having an organic layer between its anode and cathode, the organic layer being a layer responsible for light emission and / or a layer responsible for processing electrons or holes, wherein the organic layer contains the aforementioned propylene oxygenate derivative. Considering the ability of this type of material to process electrons, the organic layer preferably has an electron transport layer containing the aforementioned propylene oxygenate derivative. Considering the large number of electrons exceeding the nuclear binding capacity in this type of material, the organic layer preferably has an electron-generating layer containing the aforementioned propylene syndiol derivative. Considering that this type of material is specialized for processing electrons and its energy level is not suitable for the transport of holes, the organic layer preferably has a hole-blocking layer containing the aforementioned propylene oxygenate derivative. In addition, the present invention also discloses a photoelectric conversion element containing the aforementioned propylene oxygenate derivative. Known methods can be used in the synthesis of the propylene pyroxene derivatives of the present invention. For example, methods for introducing an aziridine host into the propylene pyroxene derivative skeleton include coupling reactions of a substituted or unsubstituted halogenated propylene pyroxene host with a substituted or unsubstituted aziridine host under a palladium or nickel catalyst, but these methods are not limited to. Furthermore, when introducing the aziridine host into the propylene pyroxene derivative via an aryl or heteroaryl group, the aziridine host may be a substituted arylboronic acid or heteroarylboronic acid, or a propylene pyroxene host substituted with a halogenated aryl group may also be used. Moreover, borate esters may be used instead of the various borate acids mentioned above. Next, embodiments of the light-emitting element of the present invention will be described in detail. The light-emitting element of the present invention includes an anode and a cathode, and an organic layer inserted between the anode and the cathode. The organic layer includes at least a light-emitting layer and an electron transport layer, and the light-emitting layer emits light using electrical energy. Besides consisting solely of a light-emitting layer / electron transport layer, organic layers can also include: 1) a stacked structure of a hole transport layer / light-emitting layer / electron transport layer; 2) a stacked structure of a hole transport layer / light-emitting layer / electron transport layer / electron injection layer; 3) a stacked structure of a hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer; and 4) a stacked structure of a hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer. Furthermore, each of these layers can be a single layer or multiple layers connected by electron-generating layers and hole-generating layers. The propylene oxygenate derivatives of the present invention can be used in any layer in the above-mentioned device configuration, but have high electron injection transport capability, fluorescence quantum yield and thin film stability. Therefore, they are preferred in electron transport layer, electron generation layer and hole blocking layer. In the light-emitting element of the present invention, the anode and cathode serve to supply sufficient current for the element to emit light. Preferably, at least one is transparent or semi-transparent in order to allow light to escape. Depending on the actual application and device design, a transparent anode or a transparent cathode can be used. The material used in the anode is not particularly limited to conductive metal oxides such as tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), or metals such as gold, silver, and chromium; inorganic conductive materials such as copper iodide and copper sulfide; or conductive polymers such as polythiophene, polypyrrole, and polyaniline. ITO glass or Nether glass is preferred. These electrode materials can be used individually or in combination. The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the device. However, from the viewpoint of power consumption, low resistance is preferred. For example, an ITO substrate with a resistance of 300 Ω / □ or less functions as a device electrode, but substrates with a resistance of around 10 Ω / □ are now also possible. Therefore, a substrate with a low resistance of 20 Ω / □ or less is preferred. The thickness of ITO can be chosen arbitrarily according to the resistance value, but it is usually used in the range of 100nm to 300nm. Furthermore, to maintain the mechanical strength of the light-emitting element, it is preferable to form the light-emitting element on the substrate. Suitable substrates include glass substrates such as soda-lime glass or alkali-free glass, as well as flexible substrates with high polymer content. The substrate thickness only needs to be sufficient to maintain mechanical strength; therefore, 0.5 mm or more is adequate. Regarding the glass material, it is preferable to use a material with fewer dissolved ions, therefore alkali-free glass is preferred. Alternatively, commercially available soda-lime glass with a barrier coating such as SiO2 can also be used. Additionally, if the first electrode can function stably, the anode can be formed on a polyimide substrate, for example. The ITO film formation method is not particularly limited to electron beam deposition, sputtering, or chemical reaction methods. The material used in the cathode is not particularly limited as long as it can efficiently inject electrons into the light-emitting layer. Generally, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium are preferred, as well as alloys or multilayers of these metals with low work function metals such as lithium, sodium, potassium, calcium, and magnesium. Among these, aluminum, silver, and magnesium are preferred as the main components, considering factors such as self-resistivity, ease of film formation, film stability, and luminous efficiency. In particular, if it is composed of magnesium and silver, electron injection into the electron transport layer and electron injection layer of the present invention becomes easier, enabling low-voltage driving, which is therefore preferred. In addition, to protect the cathode, the following methods are preferred examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys of these metals, inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, and organic polymers such as polyvinyl alcohol, polyvinyl chloride, and hydrocarbon polymers are laminated onto the cathode as a protective film layer. Furthermore, the propylene alloy derivatives of this invention can also be used as this protective film layer. However, in the case of an element structure where light is emitted from the cathode side (top-emitting structure), the protective film layer can be selected from materials that are transparent in the visible light region. These electrodes can be fabricated using methods such as resistance heating, electron beam, sputtering, ion plating, and coating, and there are no particular limitations. To further improve the light extraction efficiency and thereby reduce the reduction in light extraction efficiency caused by insufficient transparency of the transparent cathode, high-refractive-index organic materials can also be used. On top of this, metals (such as LiF) or low-refractive-index organic small molecule compounds can be used for optical adjustments, followed by a thin-film encapsulation (TFE) layer for flexible protection. This allows for flexible or even foldable devices while protecting them from the effects of water and oxygen. Specific structures are not limited. A hole transport layer can be formed by layering or mixing one or more hole transport materials, or by using a mixture of a hole transport material and a polymeric adhesive. Furthermore, the hole transport material must efficiently transport holes from the positive electrode between the electrodes subjected to an electric field; preferably, it should have high hole injection efficiency and efficient transport of the injected holes. Therefore, it is required to have a suitable ionization potential, high hole mobility, and excellent stability, and to be a substance that is unlikely to generate traps during manufacturing and use. There are no particular limitations on the substances that meet these conditions. Preferred examples include 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), bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenyl (TPD232), and other benzidine derivatives, as well as 4,4′,4″-tris(3-methylphenyl(phenyl)amino)triphenylamine (m-MTDATA) and 4,4′,4″-tris(1-naphthyl(phenyl)amine. Materials including 1-TNATA (triphenylamine) and other compounds known as starburst arylamines, materials with a carbazole backbone (including carbazole polymers, specifically derivatives of carbazole dimers, trimers, and tetramers such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triphenylbenzene compounds, pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran or thiophene derivatives, diazole derivatives, phthalocyanine derivatives, porphyrin derivatives, and other heterocyclic compounds, fullerene derivatives, and polymer systems containing the aforementioned monomers in the side chains, such as polycarbonate or styrene derivatives, polythiophene, polyaniline, polyoxocyanate, polyvinylcarbazole, and polysilane. Additionally, inorganic compounds such as p-type Si and p-type SiC can also be used. The propylene oxygenate derivatives of the present invention exhibit excellent electron injection transport characteristics. However, when used in an electron transport layer, there is a concern that electrons may not recombine in the luminescent layer, partially leaking into the hole transport layer. Therefore, it is preferable to use compounds with excellent electron blocking properties in the hole transport layer. Compounds containing a carbazole framework are preferred as they possess excellent electron blocking properties, contributing to the high efficiency of the luminescent element. Furthermore, the aforementioned carbazole-containing compounds preferably contain a carbazole dimer, carbazole trimer, or carbazole tetramer framework. This is because these compounds possess both good electron blocking and hole injection transport characteristics. Moreover, when using compounds containing a carbazole framework in the hole transport layer, it is even more preferable that the combined luminescent layer includes a phosphorescent material described later. This is because compounds with the aforementioned carbazole framework also possess high triplet exciton blocking capabilities, enabling high luminous efficiency when combined with a phosphorescent material. Furthermore, using compounds containing a triphenylene skeleton, which excels in high hole mobility, in the hole transport layer yields improved carrier balance, luminescence efficiency, and durability, which is preferable. It is even more desirable if the compound containing the triphenylene skeleton has two or more diarylamine groups. The aforementioned compounds containing a carbazole skeleton or compounds containing a triphenylene skeleton can be used individually as hole transport layers or mixed together. Other materials can also be mixed without compromising the effects of the present invention. Moreover, when the hole transport layer is constructed in multiple layers, it is sufficient to include a compound containing a carbazole skeleton or a compound containing a triphenylene skeleton in any one layer. However, it is worth noting that since the principle of luminescence involves a material simultaneously receiving electrons and holes, forming excitons, and then returning to the ground state to release energy and emit light, the luminescent material layer needs to be designed to accept electrons and holes but not transmit them. Therefore, due to the significant structural differences between materials that transmit or block electrons or holes, the propylene compounds of the present invention cannot be used in the luminescent layer. A hole injection layer can also be provided between the anode and the hole transport layer. By providing a hole injection layer, the driving voltage of the light-emitting element is reduced, and the lifespan is improved. It is preferable to use materials with a lower ionization potential than those typically used in hole transport layers in the hole injection layer. Specifically, in addition to the aforementioned group of materials such as benzidine derivatives like TPD232 and starburst-type arylamines, phthalocyanine derivatives can also be used. Furthermore, it is preferable that the hole injection layer is composed solely of an acceptor compound, or that the acceptor compound is doped into other hole transport materials. Examples of acceptor compounds include metal chlorides such as ferric(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 tris(4-bromophenyl)hexachloroantimonate (TBPAH). Moreover, organic compounds or quinone compounds, acid anhydride compounds, fullerenes, etc., that have an intramolecular nitro, cyano, halogen, or trifluoromethyl groups can also be suitably used. Specific examples of these compounds include hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyano-p-quinone dimethyl ether (TCNQ), tetrafluorotetracyano-p-quinone dimethyl ether (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatribenzene (HAT-CN6), 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-cyanonitrobenzene, m-cyanonitrobenzene, o-cyanonitrobenzene, 1,4-naphthoquinone, 2,3-dichloronaphthoquinone, 1-nitronaphthalene, 2-nitronaphthalene, 1,3-dinitronaphthalene, 1,5-dinitronaphthalene, 9-cyanoanthracene, 9-nitroanthracene, 9,10-anthraquinone, 1,3,6,8-tetranitrocarbazole, 2,4,7-trinitro-9-furonone, 2,3,5,6-tetracyanopyridine, maleic anhydride, phthalic anhydride, C60, or C70, etc. Among these compounds, metal oxides or cyano-containing compounds are preferred because they are easy to handle and readily vapor-deposit, thus readily achieving the aforementioned effects. Examples of preferred metal oxides include molybdenum oxide, vanadium oxide, or ruthenium oxide. Among cyano-containing compounds, those that (a) have at least one electron-accepting nitrogen atom in addition to the nitrogen atom of the cyano group, (b) have both a halogen and a cyano group in the molecule, (c) have both a carbonyl and a cyano group in the molecule, or (d) have both a halogen and a cyano group in the molecule, and also have at least one electron-accepting nitrogen atom in addition to the nitrogen atom of the cyano group, are preferred as they act as strong electron acceptors. Such compounds are specifically exemplified by the compounds described below. In either the case where the hole injection layer is composed solely of an acceptor compound, or where an acceptor compound is doped into the hole injection layer, the hole injection layer can be a single layer or multiple layers stacked together. Moreover, when an acceptor compound is doped, from the viewpoint of mitigating the barrier to injecting holes into the hole transport layer, it is preferable that the hole injection material used is the same compound as the compound used in the hole transport layer. Optionally, the light-emitting layer can be a single layer or multiple layers, each formed of a light-emitting material (a host material and a dopant material). Optionally, it can be a mixture of the host material and the dopant material, or it can be the host material alone. That is, in the light-emitting element of the present invention, in each light-emitting layer, only the host material or the dopant material emits light, or both the host material and the dopant material emit light. From the viewpoint of efficiently utilizing electrical energy and obtaining light emission with high color purity, it is preferable that the light-emitting layer contains a mixture of the host material and the dopant material. Moreover, optionally, the host material and the dopant material can be one type, or a combination of multiple types. Optionally, the dopant material can be included entirely or partially in the host material. Optionally, the dopant material can be stacked or dispersed. The emission color can be controlled by the dopant material. If the amount of dopant material is too large, a concentration quenching phenomenon will occur. Therefore, it is preferable to use less than 20% by weight relative to the host material, and more preferably less than 10% by weight. As a doping method, it can be formed by co-evaporation with the host material, or it can be pre-mixed with the host material and then simultaneously evaporated. Specifically, luminescent materials may include condensed ring derivatives such as anthracene or pyrene, which are known as luminescent bodies from the past; metal chelated oxinoid compounds, primarily tris(8-hydroxyquinoline)aluminum; bis(styrene) derivatives such as bis(styrene)-anthracene derivatives or styrene-phenyl derivatives; tetraphenylbutadiene derivatives; indene derivatives; coumarin derivatives; acetazole derivatives; pyrrolopyridine derivatives; violetone derivatives; cyclopentadiene derivatives; acetazole derivatives; thiadiazopyridine derivatives; dibenzofuran derivatives; carbazole derivatives; indolecarbazole derivatives; polyphenylacetylene derivatives and poly(p-phenylene) derivatives in polymer systems; and polythiophene derivatives, etc., but there are no particular limitations. The main material contained in the luminescent material is not particularly limited. It can be a compound or its derivative with a condensed aryl ring, such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, condensed tetraphenylene, triphenylene, perylene, 1,2-benzoacenaphthene, fumonisin, indene, etc.; aromatic amine derivatives such as N,N′-dinaphthyl-N,N′-diphenyl-4,4′-diphenyl-1,1′-diamine; metal chelate compounds such as tris(8-hydroxyquinoline)aluminum(III); and stilbene derivatives. The derivatives of bis(styrene) group, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, acetylene derivatives, pyrrolopyridine derivatives, violet ketone derivatives, cyclopentadiene derivatives, pyrrolopyrrole derivatives, thiadiazopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolecarbazole derivatives, triterpenoid derivatives, and polymeric derivatives such as polyphenylacetylene derivatives, poly(p-phenylene) derivatives, poly(poly(carbazole)) derivatives, and polythiophene derivatives are not particularly limited. Furthermore, there are no particular limitations on the doping material. Compounds or their derivatives with condensed aryl rings, such as naphthalene, anthracene, phenanthrene, pyrene, 1,2-benzophenanthrene, triphenylene, perylene, 1,2-benzoacenaphthene, fumonisin, and indene (e.g., 2-(benzothiazol-2-yl)-9,10-diphenylanthracene or 5,6,11,12-tetraphenyltetraphenyl), furan, pyrrole, thiophene, silacyclopentadiene, 9-silafluorene, 9,9′-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthrene, pyridine, pyridine, naphthidine, quinoline, pyrrolopyridine, and thiophene, can be used. Compounds with heteroaryl rings such as thioxanthene, or their derivatives, borane derivatives, stilbene derivatives, 4,4′-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, 4,4′-bis(N-(indino-4-yl)-N-phenylamino)indino, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, indino derivatives, aldehyde azo derivatives, and pyrromethene derivatives. Coumarin derivatives such as diketopyrrolo[3,4-c]pyrrole derivatives, 2,3,5,6-1H,4H-tetrahydro-9-(2′-benzothiazolyl)quinoyl[9,9a,1-gh]coumarin, imidazole, thiazole, thiadiazole, carbazole, succinazole, succinazole, triazole and other azole derivatives and their metal complexes, as well as aromatic amine derivatives represented by N,N′-diphenyl-N,N′-di(3-methylphenyl)-4,4′-diphenyl-1,1′-diamine, etc. Furthermore, the luminescent layer may also contain phosphorescent materials. Phosphorescent materials are materials that exhibit phosphorescence even at room temperature. When using phosphorescent materials as dopants, it is generally necessary to obtain phosphorescence even at room temperature, and there are no particular limitations. Preferably, it is an organometallic complex 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). From the viewpoint of having a high phosphorescence yield even at room temperature, organometallic complexes containing iridium or platinum are even more preferred. As a base material used in combination with phosphorescent dopants, suitable alternatives include indole derivatives, carbazole derivatives, indole-carbazole derivatives, nitrogen-containing aromatic compound derivatives with pyridine, pyrimidine, or triphenylene skeletons, polyarylbenzene derivatives, spirocyclohexene derivatives, triphenylene derivatives, and other aromatic hydrocarbon compound derivatives; dibenzofuran derivatives, dibenzothiophene derivatives, and other compounds containing sulfide elements; and organometallic complexes such as hydroxyquinoline beryllium complexes. These compounds are not limited to those with higher triplet energy compared to the primarily used dopants, allowing for smooth injection and transport of electrons and holes from their respective transport layers. Furthermore, the material may contain two or more triplet-state luminescent dopants and two or more base materials. Additionally, it may contain one or more triplet-state luminescent dopants and one or more phosphorescent dopants. There are no particular limitations on what constitutes a preferred phosphorescent host or dopant; specific examples can be listed below. In this invention, the electron transport layer is a layer that further transports electrons injected from the cathode. An ideal electron transport layer can achieve high electron injection efficiency and efficient transport of the injected electrons. Therefore, the electron transport layer is preferably composed of a material with the following properties: high electron affinity, high electron mobility, and excellent stability, making it difficult to generate impurities that could become traps during manufacturing and use. However, considering the balance between hole and electron transport, if the electron transport layer primarily functions to efficiently prevent holes from the anode from recombinizing and flowing to the cathode side, then even if it is composed of a material with relatively low electron transport capability, the effect of improving luminous efficiency becomes equivalent to that of a material with high electron transport capability. Therefore, the electron transport layer in this invention also includes a material synonymous with a hole-blocking layer that efficiently prevents hole migration. Electron transport materials used in the electron transport layer can include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styrene-based aromatic ring derivatives represented by 4,4′-bis(diphenylvinyl)biphenyl, quinone derivatives such as anthraquinone or bi-benzoquinone, phosphorus oxide derivatives, hydroxyquinoline complexes such as tris(8-hydroxyquinoline)aluminum(III), benzo(hydroxyquinoline) complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes, among other metal complexes. Considering the need to reduce the driving voltage and achieve high-efficiency luminescence, it is preferable to use compounds with heteroaryl ring structures. These heteroaryl ring structures are composed of elements selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus, and include electron-accepting nitrogen. Aromatic heterocycles containing electron-accepting nitrogen exhibit high electron affinity. Electron transport materials containing electron-accepting nitrogen readily accept electrons from cathodes with high electron affinity, enabling lower voltage driving. Furthermore, the lone pairs of electrons in electron-accepting nitrogen, after incorporating into the large π bond, can accommodate more electrons, increasing electron load and improving electron transport capability. Moreover, the increased electron supply to the luminescent layer leads to a higher recombination probability, thus improving luminescence efficiency. Examples of heteroaryl rings containing electron-accepting nitrogen include pyridine rings, pyridine rings, pyrimidine rings, quinoline rings, quinoline rings, naphthidine rings, pyrimidine rings, benzoquinoline rings, phenanthrene rings, imidazole rings, thiazole rings, thiadiazole rings, triazole rings, thiazole rings, benzothiazole rings, benzoimidazolium rings, phenanthrene imidazolium rings, etc. Compounds possessing these heteroaryl ring structures include, for example, benzimidazole derivatives, benzo[a]azole derivatives, benzo[thiazol]azole derivatives, acediazole derivatives, thiadiazole derivatives, triazole derivatives, pyridine derivatives, phenanthroline derivatives, quinoline derivatives, quinoline derivatives, benzo[quinoline], oligopyridine derivatives such as bipyridine or terpyridine, quinoline derivatives, and naphthidine derivatives as preferred compounds. From the viewpoint of electron transport capability, imidazole derivatives such as tris(N-phenylbenzimidazole-2-yl)benzene, acediazole derivatives such as 1,3-bis[(4-tert-butylphenyl)1,3,4-acediazole]benzene, triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathcuproine or 1,3-bis(1,10-phenanthroline-9-yl)benzene, and 2 Benzoquinoline derivatives such as 2′-bis(benzo[h]quinoline-2-yl)-9,9′-spirodicyclohexane, bipyridine derivatives such as 2,5-bis(6′-(2′,2″-bipyridine))-1,1-dimethyl-3,4-diphenylsilanecyclopentadiene, terpyridine derivatives such as 1,3-bis(4′-(2,2′:6′2″-terpyridyl))benzene, and naphthidine derivatives such as bis(1-naphthyl)-4-(1,8-naphthidin-2-yl)phenylphosphine oxide are preferred. Furthermore, derivatives with condensed polycyclic aromatic skeletons exhibit increased glass transfer temperature and electron mobility, resulting in greater low-voltage performance of the light-emitting element. Additionally, considering improved element lifespan, ease of synthesis, and readily available raw materials, condensed polycyclic aromatic skeletons such as anthracene, pyrene, or phenanthroline skeletons are particularly advantageous. The aforementioned electron transport materials can be used alone, or two or more of the aforementioned electron transport materials can be used in combination, or one or more other electron transport materials can be mixed into the aforementioned electron transport materials. The propylene oxygenate derivative of the present invention also has high electron injection transport capability, and therefore can be suitably used as an electron transport material. When using the propylene chelate derivatives of the present invention, it is not necessary to limit oneself to one of them. Multiple propylene chelate compounds of the present invention can be mixed and used together, or one or more other electron transport materials can be mixed and used with the propylene chelate compounds of the present invention without impairing the effects of the present invention. As a miscible electron transport material, there is no particular limitation. Examples include compounds having condensed aryl rings such as naphthalene, anthracene, and pyrene, or their derivatives; styrene-based aromatic ring derivatives represented by 4,4′-bis(diphenylvinyl)biphenyl; perylene derivatives; violet ketone derivatives; coumarin derivatives; naphthyldimethylimine derivatives; quinone derivatives such as anthraquinone or bi-benzoquinone; phosphorus oxide derivatives; carbazole derivatives and indole derivatives; hydroxyquinoline complexes such as tris(8-hydroxyquinoline)aluminum(III) or hydroxyphenyl oxychloride complexes such as hydroxyazole complexes; azomethine complexes; tyrosine metal complexes; and flavonol metal complexes. The aforementioned electron transport materials can be used alone, or two or more of the aforementioned electron transport materials can be used in combination, or one or more other electron transport materials can be mixed into the aforementioned electron transport materials. Furthermore, they may contain donor materials. Here, the donor material is a compound that improves the electron injection barrier, facilitating electron injection from the cathode or electron injection layer to the electron transport layer, and further enhancing the conductivity of the electron transport layer. Preferred examples of donor materials in this invention include alkali metals, inorganic salts containing alkali metals, complexes of alkali metals and organic compounds, alkaline earth metals, inorganic salts containing alkaline earth metals, or complexes of alkaline earth metals and organic compounds. Preferred types of alkali metals and alkaline earth metals include lithium, sodium, cesium, ytterbium, and other alkali metals and their compounds, which have low work function and significantly improve electron transport capabilities, or magnesium, calcium, and other alkaline earth metals and their compounds. The suitable doping concentration varies depending on the material or the film thickness of the doped region. For example, when the donor material is an inorganic material such as an alkali metal or alkaline earth metal, it is preferable to co-deposit the electron transport layer by a deposition rate ratio of 10000:1 to 2:1 between the electron transport material and the donor material. A more preferred deposition rate ratio is 100:1 to 5:1, and even more preferred is 100:1 to 10:1. Furthermore, when the donor material is a metal-organic complex, it is preferable to co-deposit the electron transport layer by a deposition rate ratio of 100:1 to 1:100 between the electron transport material and the donor material. A more preferred deposition rate ratio is 10:1 to 1:10, and even more preferred is 7:3 to 3:7. Furthermore, the electron transport layer doped with donor material in the propylene oxygen derivative of the present invention as described above can be used as a charge generation layer in a series structure element that connects multiple light-emitting elements. The method of improving electron transport capability by doping the electron transport layer with donor materials is particularly effective when the film thickness is relatively thick. It is especially suitable when the combined thickness of the electron transport layer and the emitting layer is 50 nm or more. For example, there are methods that utilize interference effects to improve luminous efficiency, which involves aligning the phase of light emitted directly from the self-emitting layer with the light reflected by the cathode, thereby increasing the light emission efficiency. The optimal conditions vary depending on the emission wavelength; when the combined thickness of the electron transport layer and the emitting layer is 50 nm or more, and the light emits at a red wavelength, a film thickness approaching 100 nm can be achieved. The thickness of the doped electron transport layer can be arbitrary, consisting of part or all of the electron transport layer. When doping only a portion, it is ideal to have a doped region at least at the electron transport layer / cathode interface; even doping only near the cathode interface can achieve a low-voltage effect. On the other hand, if the donor material is directly in contact with the luminescent layer, it can have an adverse effect on reducing luminous efficiency. In this case, it is preferable to have an undoped region at the luminescent layer / electron transport layer interface. In this invention, an electron injection layer may also be provided between the cathode and the electron transport layer. Generally, the electron injection layer is inserted to facilitate the injection of electrons from the cathode into the electron transport layer. When inserted, a compound having a heteroaryl ring structure containing electron-accepting nitrogen can be used, or a layer containing the aforementioned donor material can be used. The electron injection layer may also contain the propylene sulfide derivative of this invention. Furthermore, inorganic materials that are insulators or semiconductors, or metals, can also be used in the electron injection layer. Using these materials effectively prevents short circuits in the light-emitting element and improves electron injection performance, which is preferable. Preferably, the insulator is at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides, it is even better in terms of further improving electron injection performance. Specifically, preferred alkali metal chalcogenides include, for example, Li... 2O, Na 2S and Na 2Se, preferred alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, BeO, BaS, and CaSe. Furthermore, preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl. Moreover, preferred alkaline earth metal halides include, for example, CaF… 2. BaF 2. SrF 2. MgF 2 and BeF 2. Fluorides or halides other than fluorides. Complexes of organic compounds and metals may also be suitable. When using complexes of organic compounds and metals in the electron injection layer, the film thickness is easily adjusted, which is therefore preferable. Examples of such organometallic complexes include, as preferred examples of organic compounds in complexes with organic compounds, hydroxyquinoline, benzo[a]hydroxyquinoline, pyridylphenol, flavonols, hydroxyimidazo[a]pyridine, hydroxyindene, hydroxytriazole, etc. Additionally, metals may also be used, such as Li, Yb, Ba, etc. The methods for forming the layers constituting the light-emitting element include resistance heating evaporation, electron beam evaporation, sputtering, molecular layering, coating, etc., without any particular limitation. Generally, considering the characteristics of the element, resistance heating evaporation or electron beam evaporation is preferred. The thickness of the organic layer is determined by the resistance value of the luminescent material and therefore cannot be limited, but is preferably 1 nm to 1000 nm. The film thicknesses of the luminescent layer, electron transport layer, and hole transport layer are preferably above 1 nm and below 200 nm, respectively, and more preferably above 5 nm and below 100 nm. The light-emitting element of this invention has the function of converting electrical energy into light. Here, the electrical energy is mainly direct current, but pulsed current or alternating current can also be used. There are no particular limitations on the current and voltage values; however, when considering the power consumption or lifespan of the element, it should be selected in a way that obtains maximum brightness using the lowest possible energy. The light-emitting element of the present invention can also be preferably used as backlighting for various devices, etc. Backlighting is primarily used to improve the visibility of non-self-emissive display devices, and is used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs, etc. The light-emitting element of the present invention is particularly preferred for backlighting liquid crystal displays (especially for personal computers where thinning has been studied), providing a thinner and lighter backlight than existing backlights. [Examples] The present invention is illustrated below with examples, but the present invention is not limited to these examples. The materials used in the examples and comparative examples are as follows: Toluene, xylene, methanol, etc. were purchased from Sinopharm Company; triterpenoids were purchased from TCI; propylene compounds were purchased from Alfa-Aeser; various catalysts, etc. were purchased from Aldrich Company. Synthesis Example 1 Synthesis of compound [6] 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triphenylamine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.5 g of a white solid, 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triphenylamine. 3.5 g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triphenylamine, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 7 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to obtain 4.68 g of a yellow solid compound [6] (purity 99.9%). Synthesis Example 2 Synthesis of Compound [7] 3.00 g of 2-(4-biphenyl)-4,6-dichloro-1,3,5-tris(II) and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 1.22 g 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 the reaction was quenched with cold water. The reactants were then extracted with toluene, and the salts were extracted with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.2 g of a white solid, 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-tris(II). 3.2 g of 2-(4-p-biphenyl)-4-chloro-6-phenyl-1,3,5-tris(2-di ...)-1,3,5-tris(2-diphenyl)-4-chloro-6-phenyl)-1,3,5-tris(2-diphenyl)-4-chloro-6-phenyl)-1,3,5-tris(2-diphenyl)-4-chloro-6-phenyl)-1,3,5-tris(2-diphenyl)-4-chloro-6-phenyl)-1,3,5-tris(2-diphenyl)-4-chloro-6-phenyl)-1,3,5-tris(2-diphenyl)-4-chloro- 3.82 g of 2-(4-p-biphenyl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triphenylamine, 2.3 g of propylene boric acid, 0.12 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 50 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to obtain 5.21 g of a pale yellow solid compound [7] (purity 99.9%). Synthesis Example 3 Synthesis of compound [8] 3.00 g of 2-(4-biphenyl)-4,6-dichloro-1,3,5-tris(II) and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 1.22 g 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 the reaction was quenched with cold water. The reactants were then extracted with toluene, and the salts were extracted with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.2 g of a white solid, 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-tris(II). 3.2 g of 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-tris(II)-methyl, 1.56 g of m-chlorophenylboronic acid, 0.06 g of diphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 80 ml of o-xylene to give 3.78 g of a white solid, 2-(4-biphenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-tris(II). 3.78 g of 2-(4-biphenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triphenylamine, 2.3 g of propylene boric acid, 0.12 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 50 ml of methanol, respectively. The mixture was recrystallized with 80 ml of o-xylene to obtain 5.00 g of a pale yellow solid compound [8] (purity 99.9%). Synthesis Example 4 Synthesis of compound [9] 2.55 g of 2-phenyl-4,6-dichloro-1,3,5-triphenyl ether and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask, purged three times with argon, and then dehydrated and deoxygenated toluene was injected and stirred for 20 minutes. 2.00 g of m-bromobiphenyl dissolved in toluene was added, and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature, and the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.1 g of a white solid, 2-(4-phenyl)-4-chloro-6-meta-phenyl-1,3,5-triphenyl ether. 3.1 g of 2-(4-phenyl)-4-chloro-6-metaphenyl-1,3,5-triphenylamine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to give 3.75 g of a white solid, 2-(4-phenyl)-4-(4-chlorophenyl)-6-metaphenyl-1,3,5-triphenylamine. 3.75 g of 2-(4-phenyl)-4-(4-chlorophenyl)-6-metaphenyl-1,3,5-triphenylamine, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to obtain 4.94 g of a pale yellow solid compound [9] (purity 99.9%). Synthesis Example 5 Synthesis of compound

[10] 2.55 g of 2-phenyl-4,6-dichloro-1,3,5-triphenyl ether and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask, purged three times with argon, and then dehydrated and deoxygenated toluene was injected and stirred for 20 minutes. 2.00 g of m-bromobiphenyl dissolved in toluene was added, and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature, and the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.1 g of a white solid, 2-(4-phenyl)-4-chloro-6-meta-phenyl-1,3,5-triphenyl ether. 3.1 g of 2-(4-phenyl)-4-chloro-6-metaphenyl-1,3,5-triphenylamine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 3 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 80 ml of o-xylene to give 3.83 g of a white solid, 2-(4-phenyl)-4-(3-chlorophenyl)-6-metaphenyl-1,3,5-triphenylamine. 3.83 g of 2-(4-phenyl)-4-(3-chlorophenyl)-6-metaphenyl-1,3,5-triphenylamine, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 8 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 50 ml of methanol, respectively. The mixture was recrystallized with 80 ml of o-xylene to obtain 5.11 g of a pale yellow solid compound

[10] (purity 99.9%). Synthesis Example 6 Synthesis of compound

[18] 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triphenylamine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.5 g of a white solid, 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triphenylamine. 3.5 g of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triphenylbenzyl ... 4.1 g of 4-chloro-4'-(4,6-diphenyl-1,3,5-triphenyl)biphenyl, 2.1 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to obtain 5.82 g of a pale yellow solid compound

[18] (purity 99.9%). Synthesis Example 7 Synthesis of compound

[22] 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triphenylfuran, 2.12 g of 2-dibenzofuranboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 5.20 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated xylene was injected. The reaction was carried out in ice water for 1 hour. After warming to room temperature, the reaction was continued for 3 hours. The solvent was then evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to obtain 3.8 g of a white solid, 2-(4,6-diphenyl-1,3,5-triphenyl)-dibenzofuran. 3.8 g of 2-(4,6-diphenyl-1,3,5-trisyl)-dibenzofuran, 3.4 g of N-bromosuccinimide, and 3.60 g of potassium phosphate trihydrate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was separated using a silicone column (PE:EA = 1:20) to obtain 4.2 g of a white solid, 2-(4,6-diphenyl-1,3,5-trisyl)-8-bromodibenzofuran. 4.2 g of 2-(4,6-diphenyl-1,3,5-tris(2,4-diphenyl)-8-bromodibenzofuran, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated xylene was injected. The mixture was heated to 150°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 200 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to obtain 5.13 g of a pale yellow solid compound

[22] (purity 99.9%). Synthesis Example 8 Synthesis of compound

[25] 2.64 g of 2-chloro-4,6-diphenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.4 g of a white solid, 2-(4-chlorophenyl)-4,6-diphenylpyrimidine. 3.4 g of 2-(4-chlorophenyl)-4,6-diphenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.0 g of a white solid, 4-chloro-4'-(4,6-diphenylpyrimidine)biphenyl. 4.0 g of 4-chloro-4'-(4,6-diphenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to obtain 5.90 g of a pale yellow solid compound

[25] (purity 99.9%). Synthesis Example 9 Synthesis of compound

[26] 2.64 g of 4-chloro-2,6-diphenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.4 g of a white solid, 4-(4-chlorophenyl)-2,6-diphenylpyrimidine. 3.4 g of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.0 g of a white solid, 4-chloro-4'-(2,6-diphenylpyrimidine)biphenyl. 4.0 g of 4-chloro-4'-(2,6-diphenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 5.90 g of a pale yellow solid compound

[26] (purity 99.9%). Synthesis Example 10 Synthesis of compound

[28] 2.9 g of 2,6-diphenyl-4-chloropyridine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed twice with 100 ml of water to obtain 3.4 g of a white solid, 4-(2,6-diphenylpyridyl)chlorobenzene. 3.4 g of 4-(2,6-diphenylpyridinyl)chlorobenzene, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and three times with 100 ml of methanol to obtain 4.0 g of a white solid, 4-chloro-4'-(2,6-diphenylpyridinyl)biphenyl. 4.0 g of 4-chloro-4'-(2,6-diphenylpyridyl)biphenyl, 2.1 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 4 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to obtain 5.45 g of a pale yellow solid compound

[28] (purity 99.9%). Synthesis Example 11 Synthesis of compound

[30] 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.60 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine. 4.6 g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine, 1.56 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.8 g of a white solid, 4-chloro-3'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl. 4.8 g of 4-chloro-3'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2 g of propadiene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 6.10 g of a pale yellow solid compound

[30] (purity 99.9%). Synthesis Example 12 Synthesis of compound

[37] 2.55 g of 2-phenyl-4,6-dichloro-1,3,5-triphenyl ether and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask, purged three times with argon, and then dehydrated and deoxygenated toluene was injected and stirred for 20 minutes. 2.00 g of m-bromobiphenyl dissolved in toluene was added, and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature, and the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.1 g of a white solid, 2-(4-phenyl)-4-chloro-6-meta-phenyl-1,3,5-triphenyl ether. 3.1 g of 2-(4-phenyl)-4-chloro-6-meta-phenyl-1,3,5-triphenylamine, 1.21 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.9 g of a white solid, 2-(3-chlorophenyl)-4-phenyl-6-meta-phenyl-1,3,5-triphenylamine. 3.9 g of 2-(3-chlorophenyl)-4-phenyl-6-meta-phenyl-1,3,5-triphenylbenzyl ... 5.0 g of 3-chloro-3'-(4-phenyl-6-meta-phenyl-1,3,5-triphenyl)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to give 6.3 g of a pale yellow solid compound

[37] (purity 99.9%). Synthesis Example 13 Synthesis of compound

[38] 2.64 g of 4-chloro-2,6-diphenylpyrimidine, 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. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.4 g of a white solid, 4-(3-chlorophenyl)-2,6-diphenylpyrimidine. 3.4 g of 4-(3-chlorophenyl)-2,6-diphenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.0 g of a white solid, 3-chloro-3'-(2,6-diphenylpyrimidine)biphenyl. 4.0 g of 3-chloro-3'-(2,6-diphenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 5.78 g of a pale yellow solid compound

[38] (purity 99.9%). Synthesis Example 14 Synthesis of compound

[39] 2.64 g of 2-chloro-4,6-diphenylpyrimidine, 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. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.4 g of a white solid, 2-(3-chlorophenyl)-4,6-diphenylpyrimidine. 3.4 g of 2-(3-chlorophenyl)-4,6-diphenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.0 g of a white solid, 3-chloro-3'-(4,6-diphenylpyrimidine)biphenyl. 4.0 g of 3-chloro-3'-(4,6-diphenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 5.92 g of a pale yellow solid compound

[39] (purity 99.9%). Synthesis Example 15 Synthesis of compound

[43] 2.67 g of 2-chloro-4,6-diphenyl-1,3,5-triphenylpyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 80°C and reacted for 24 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 3.2 g of a white solid, 2-(2-chlorophenyl)-4,6-diphenylpyrimidine. 3.2 g of 2-(2-chlorophenyl)-4,6-diphenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 3.8 g of a white solid, 3-chloro-2'-(4,6-diphenylpyrimidine)biphenyl. 3.8 g of 3-chloro-2'-(4,6-diphenylpyrimidine)biphenyl, 2.2 g of propadiene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 5.65 g of a pale yellow solid compound

[43] (purity 99.9%). Synthesis Example 16 Synthesis of compound

[61] 3.00 g of 2-(4-biphenyl)-4,6-dichloro-1,3,5-tris(II) and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 1.22 g 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 the reaction was quenched with cold water. The reactants were then extracted with toluene, and the salts were extracted with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.2 g of a white solid, 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-tris(II). 3.2 g of 2-(4-p-Biphenyl)-4-chloro-6-phenyl-1,3,5-tris(2-chlorophenylboronic acid), 1.22 g of p-chlorophenylboronic acid, 0.06 g of diphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to give 4.0 g of a white solid, 2-(4-chlorophenyl)-4-p-Biphenyl-6-phenyl-1,3,5-tris(2-chlorophenyl) ... 4.0 g of 2-(4-chlorophenyl)-4-p-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to obtain 4.8 g of a white solid, 4-chloro-4'-(4-p-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl. 4.8 g of 4-chloro-4'-(4-p-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 2.2 g of propadiene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 200 ml of o-xylene to give 6.4 g of a pale yellow solid compound

[61] (purity 99.9%). Synthesis Example 17 Synthesis of compound

[62] 2.55 g of 2-phenyl-4,6-dichloro-1,3,5-triphenyl ether and 0.24 g of hydrochloric acid-activated magnesium block were placed in a flask, purged three times with argon, and then dehydrated and deoxygenated toluene was injected and stirred for 20 minutes. 2.00 g of m-bromobiphenyl dissolved in toluene was added, and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature, and the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 3.1 g of a white solid, 2-(4-phenyl)-4-chloro-6-meta-phenyl-1,3,5-triphenyl ether. 3.1 g of 2-(4-phenyl)-4-chloro-6-metaphenyl-1,3,5-triphenylamine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to give 3.9 g of a white solid, 2-(4-chlorophenyl)-4-metaphenyl-6-phenyl-1,3,5-triphenylamine. 3.9 g of 2-(4-chlorophenyl)-4-meta-phenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.8 g of a white solid, 4-chloro-4'-(4-meta-phenyl-6-phenyl-1,3,5-triphenyl)biphenyl. 4.8 g of 4-chloro-4'-(4-meta-phenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 2.2 g of propadiene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to give 6.5 g of a pale yellow solid compound

[62] (purity 99.9%). Synthesis Example 18 Synthesis of compound

[63] 2.55 g of 2-phenyl-4,6-dichloro-1,3,5-triphenyl was placed in a flask along with 0.24 g of hydrochloric acid-activated magnesium. After purging three times with argon, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 2.00 g of o-bromobiphenyl dissolved in toluene was added, and the temperature was raised to 120°C. After 4 hours, the mixture was cooled to room temperature, and the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction with water to remove the salts. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:30) yielded 3.0 g of a white solid, 2-(4-phenyl)-4-chloro-6-o-biphenyl-1,3,5-triphenyl. 3.0 g of 2-(4-phenyl)-4-chloro-6-o-biphenyl-1,3,5-triphenylamine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 40 ml of o-xylene to give 3.7 g of a white solid, 2-(4-chlorophenyl)-4-o-biphenyl-6-phenyl-1,3,5-triphenylamine. 3.7 g of 2-(4-chlorophenyl)-4-o-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.5 g of a white solid, 4-chloro-4'-(4-o-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl. 4.5 g of 4-chloro-4'-(4-o-biphenyl-6-phenyl-1,3,5-triphenyl)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to give 6.1 g of a pale yellow solid compound

[63] (purity 99.9%). Synthesis Example 19 Synthesis of compound

[106] 1.82 g of 1,3,5-trichlorotriazine and 0.48 g of hydrochloric acid-activated magnesium block were placed in a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 5.0 g 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 the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 4.0 g of a white solid, a bis(dibenzofuran) substituted product. 4.0 g of the bis(4-)-dibenzofuran derivative, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di(triphenylphosphine)palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to give 5.1 g of a white solid, 2-(4-chlorophenyl)-4,6-bis(4-)-dibenzofuran-1,3,5-triphenylfuran. 5.1 g of 2-(4-chlorophenyl)-4,6-bis(dibenzofuran)-1,3,5-triphenyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 100 ml of o-xylene to obtain 5.7 g of a white solid, 4-chloro-4'-(4,6-bis(dibenzofuran)-1,3,5-triphenyl)biphenyl. 5.7 g of 4-chloro-4'-(4,6-bis(dibenzofuran-1,3,5-tris(2-diphenyl)biphenyl), 2.1 g of propylene borate, 0.06 g of diphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 200 ml of o-xylene to give 6.5 g of a pale yellow solid compound

[106] (purity 99.9%). Synthesis Example 20 Synthesis of compound

[110] 1.82 g of 1,3,5-trichlorotriazine and 0.48 g of hydrochloric acid-activated magnesium block were placed in a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected, and the mixture was stirred for 20 minutes. 5.0 g 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 the reaction was quenched with cold water. The reactants were then extracted with toluene, followed by extraction of the salts with water. The organic phase was evaporated to dryness to obtain a solid. Separation using a silicone column (PE:EA = 1:10) yielded 4.0 g of a white solid, a bis(dibenzofuran) substituted product. 4.0 g of the bis(3-chlorophenyl)-4,6-bis(3-benzofuran)-1,3,5-triphenylphosphine palladium dichloride was added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to give 5.2 g of a white solid, 2-(3-chlorophenyl)-4,6-bis(3-benzofuran)-1,3,5-triphenylphosphine. 5.2 g of 2-(3-chlorophenyl)-4,6-bis(dibenzofuran)-1,3,5-triphenylbenzyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 5.8 g of a white solid, 3-chloro-3'-(4,6-bis(dibenzofuran)-1,3,5-triphenyl)biphenyl. 5.8 g of 3-chloro-3'-(4,6-bis(dibenzofuran-1,3,5-trisyl)biphenyl, 2.1 g of propadiene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 6.5 g of a pale yellow solid compound

[110] (purity 99.9%). Synthesis Example 21 Synthesis of compound

[111] 2.7 g of 3,5-dibromochlorobenzene, 5.0 g of propadiene-boronic acid, 0.06 g of di(triphenylphosphine)palladium dichloride, and 7.20 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and three times with 200 ml of methanol. Recrystallization was performed using 100 ml of o-xylene to obtain 5.0 g of a yellow solid, 3,5-dipropadiene-boronic acid. 5.0 g of 1,3-dipropadiene-5-chlorobenzene, 2.33 g of trichlorobenzene 1,3-diphenyl-5-boronic acid, 0.06 g of palladium dichloride dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 5 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and twice with 100 ml of methanol. It was recrystallized with 70 ml of o-xylene to give 6.5 g (purity 99.9%) of a pale yellow solid compound

[111] . Synthesis Example 22 Synthesis of compound

[112] 3.46 g of 2,4,6-tribromochlorobenzene, 7.5 g of propadiene-boronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 10.0 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 2 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and three times with 200 ml of methanol. Recrystallization was performed using 200 ml of o-xylene to obtain 7.1 g of a yellow solid, 2,4,6-tripropadiene-boronic acid. 7.1 g of 2,4,6-tripropadiene chlorobenzene, 2.33 g of triphenyl-5-boronic acid, 0.06 g of palladium dichloride dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 5 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and twice with 100 ml of methanol. It was recrystallized from 300 ml of o-xylene to give 8.0 g (purity 99.9%) of a yellow solid compound

[112] . Synthesis Example 23 Synthesis of compound

[113] 2.7 g of 3,5-dibromochlorobenzene, 4.66 g of tris(3,5-diphenyl-5-boronic acid), 0.06 g of palladium dichloride dichloride, and 5.0 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 4 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and three times with 100 ml of methanol. Recrystallization was performed using 100 ml of o-xylene to obtain 5.5 g of a white solid, 3,5-bis(3,5-diphenyltris(3,5-diphenyl)chlorobenzene. 5.5 g of 3,5-bis(3,5-diphenyltrisyl)chlorobenzene, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and three times with 100 ml of methanol. Recrystallization was performed using 200 ml of o-xylene to obtain 6.2 g of a white solid, 1-(4-chlorophenyl)-3,5-bis(1,3-diphenyltrisyl)benzene. 6.2 g of 1-(4-chlorophenyl)-3,5-bis(1,3-diphenyltriphenyl)benzene, 2.1 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 500 ml of o-xylene to give 8.0 g of a white solid compound

[113] (purity 99.9%). Synthesis Example 24 Synthesis of compound

[114] 2.8 g of 3,5-diphenylchlorobenzene, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water to obtain 3.4 g of a white solid, 2-(4-chlorophenyl)-4,6-diphenylbenzene. 3.4 g of 2-(4-chlorophenyl)-4,6-diphenylbenzene, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.0 g of a white solid, 4-chloro-4'-(4,6-diphenylbenzene)biphenyl. 4.0 g of 4-chloro-4'-(4,6-diphenylbenzene)biphenyl, 2.1 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 4 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 300 ml of methanol, respectively. The mixture was recrystallized from 6000 ml of o-xylene to give 5.31 g of a pale yellow solid compound

[114] (purity 99.9%). Synthesis Example 25 Synthesis of compound

[115] 3.4 g of 1-(4-chlorophenyl)-3-p-biphenyl-2,4,5,6-tetraphenylbenzyl)biphenyl, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.1 g of a white solid, 4-chloro-4'-(1,3-p-biphenyl-2,4,5,6-tetraphenyl)biphenyl. 4.1 g of 4-chloro-4'-(1-3-p-biphenyl-2,4,5,6-tetrafluoroethylene)biphenyl, 2.1 g of propylene boronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed four times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 100 ml of o-xylene to give 3.13 g of a white solid compound

[115] (purity 99.9%). Synthesis Example 26 Synthesis of compound

[138] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltrisulfite, 1.22 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.63 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyltrisulfite. 4.63 g of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyltriphenylbiphenyl (PTB), 1.56 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.7 g of a white solid, 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-triphenylbiphenyl). 4.7 g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-triphenyl)biphenyl, 2.2 g of propylene borate, 0.06 g of diphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.25 g of a pale yellow solid compound

[138] (purity 99.9%). Synthesis Example 27 Synthesis of compound

[139] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.61 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 4.6 g of 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.24 g of a pale yellow solid compound

[139] (purity 99.9%). Synthesis Example 28 Synthesis of compound

[140] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.65 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.7 g of a white solid, 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl. 4.7 g of 4-chloro-2'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 4.56 g of a pale yellow solid compound

[140] (purity 99.9%). Synthesis Example 29 Synthesis of compound

[141] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltrisulfite, 1.22 g of p-chlorophenylboronic acid, 0.06 g of diphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.50 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyltrisulfite. 4.50 g of 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyltriphenylbenzene, 1.56 g of o-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-triphenylbenzene). 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-triphenyl)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.20 g of a pale yellow solid compound

[141] (purity 99.9%). Synthesis Example 30 Synthesis of compound

[142] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.41 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 4.6 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.10 g of a pale yellow solid compound

[142] (purity 99.9%). Synthesis Example 31 Synthesis of compound

[143] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.50 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.41 g of a white solid, 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl. 4.41 g of 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-4-yl-pyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.08 g of a pale yellow solid compound

[143] (purity 99.9%). Synthesis Example 32 Synthesis of compound

[183] 3.50 g of 2,6-diphenyl-4-chlorotrichlorotrichloroacetic acid, 1.22 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.53 g of a white solid, 2,6-diphenyl-4-(2-chlorophenyl)trichloroacetic acid. 4.53 g of 2,6-diphenyl-4-(2-chlorophenyl)triphenylbenzyl chloride, 1.56 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging three times with argon gas, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.61 g of a white solid, 4-chloro-2'-(2,6-diphenyltriphenyl)biphenyl. 4.61 g of 4-chloro-2'-(2,6-diphenyltriphenyl)biphenyl, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.46 g of a pale yellow solid compound

[183] ​​(purity 99.9%). Synthesis Example 33 Synthesis of compound

[186] 3.50 g of 2,6-diphenyl-4-chlorotriphenylamine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.30 g of a white solid, 2,6-diphenyl-4-(4-chlorophenyl)triphenylamine. 4.30 g of 2,6-diphenyl-4-(4-chlorophenyl)triphenylbenzene, 1.56 g of o-chlorophenylboronic acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.50 g of a white solid, 2-chloro-4'-(2,6-diphenyl-4-yl-triphenyl)biphenyl. 4.50 g of 2-chloro-4'-(2,6-diphenyl-4-yl-triphenyl)biphenyl, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 3.10 g of a pale yellow solid compound

[186] (purity 99.9%). Synthesis Example 34 Synthesis of compound

[148] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of o-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.61 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 4-chloro-2'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 4.60 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to give 3.01 g of a white solid, 4-(4-chlorophenyl)-3'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 3.01 g of 4-(4-chlorophenyl)-3'-(4-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 2.0 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 2.11 g of a pale yellow solid compound

[148] (purity 99.9%). Synthesis Example 35 Synthesis of compound

[151] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.41 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 2-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 4.60 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to give 2.54 g of a white solid, 2-(4-chlorophenyl)-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 2.54 g of 2-(4-chlorophenyl)-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl, 0.06 g of diphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized from 120 ml of o-xylene to give 1.02 g of a pale yellow solid compound

[151] (purity 99.9%). Synthesis Example 36 Synthesis of compound

[154] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of p-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 4.41 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine. 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.6 g of a white solid, 4-chloro-4'-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)biphenyl. 4.60 g of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine, 1.56 g of o-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 3.12 g of a white solid, 2''-chloro-4-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)terphenyl. 3.12 g of 2''-chloro-4-(2-phenyl-[1,1'-biphenyl]-6-yl-pyrimidine)terphenyl, 2.0 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 1.20 g of a pale yellow solid compound

[154] (purity 99.9%). Synthesis Example 37 Synthesis of compound

[34] 3.67 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyltrisulfite, 1.22 g of m-chlorophenylboronic acid, 0.06 g of diphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 3.50 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyltrisulfite. 3.50 g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyltriphenylbenzene, 1.56 g of m-chlorophenylboronic acid, 0.06 g of diphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.2 g of a white solid 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenyltriphenylbenzene). 4.2 g of white solid 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenyltriphenyl)biphenyl, 2.2 g of propylene boric acid, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to give 4.73 g of pale yellow solid compound

[34] (purity 99.9%). Synthesis Example 38 Synthesis of compound

[40] 3.67 g of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine, 1.22 g of m-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 3.70 g of a white solid, 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine. 3.70 g of 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.10 g of a white solid 3-chloro-3'-(4-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine)biphenyl. 4.10 g of white solid 3-chloro-3'-(4-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to obtain 4.31 g of pale yellow solid compound

[40] (purity 99.9%). Synthesis Example 39 Synthesis of compound

[41] 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 di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 50 ml of o-xylene to obtain 3.69 g of a white solid, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine. 3.69 g of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine, 1.56 g of m-chlorophenylboronic acid, 0.06 g of di-triphenylphosphine palladium dichloride, and 3.60 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 1 hour. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water. Recrystallization was performed using 70 ml of o-xylene to obtain 4.02 g of a white solid, 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine)biphenyl. 4.02 g of white solid 3-chloro-3'-(2-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidine)biphenyl, 2.2 g of propylene borate, 0.06 g of ditriphenylphosphine palladium dichloride, and 3.6 g of potassium carbonate were added to a flask. After purging with argon three times, dehydrated and deoxygenated toluene was injected. The mixture was heated to 120°C and reacted for 12 hours. After cooling to room temperature, the solvent was evaporated, and the mixture was washed three times with 100 ml of water and 100 ml of methanol, respectively. The mixture was recrystallized with 120 ml of o-xylene to obtain 3.90 g of a pale yellow solid compound

[41] (purity 99.9%). Example 1 A glass substrate (manufactured by Geomatec Co., Ltd., 11Ω / □, sputtered) with a 165nm ITO transparent conductive film deposited on it was cut into 38mm × 46mm pieces and etched. The resulting substrate was ultrasonically cleaned for 15 minutes using Semico Clean 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.), and then rinsed with ultrapure water. Before component fabrication, the substrate was subjected to a 1-hour ultraviolet (UV)-ozone treatment in a vacuum evaporation apparatus, with exhaust gas applied until the vacuum level reached 5 × 10⁻⁶. -4Below Pa. Using resistance heating, HAT-CN6 of 75 nm was first deposited as a hole injection layer, and HT-1 of 42.5 nm was deposited as a hole transport layer. Then, the host material H-1 and the dopant material D-1 were deposited to a thickness of 20 nm at a doping concentration of 5% by weight as the light-emitting layer. Then, compound [6] was deposited to a thickness of 30 nm as the electron transport layer. Then, Yb of 1 nm was deposited, and Mg / Aa (1:9) of 15 nm was deposited as the cathode to fabricate a 5 mm × 5 mm square element. The film thickness referred to here is the value displayed by a quartz oscillating film thickness monitor (Conltaec Eon LT). The light-emitting element has a thickness of 10 mA / cm. 2 The characteristics at that time were a driving voltage of 4.51V and an efficiency of 6.6cd / A. Furthermore, the initial brightness was set to 10mA / cm. 2 When driven by a constant current, the brightness decreases by 50% in 1600 hours, resulting in a halving time. HAT-CN6, HT-1, H-1, and D-1 are the compounds shown below. This type of device, consisting of a single light-emitting unit, is called a single-layer device to distinguish it from the tandem device, which consists of more than one light-emitting unit, as described below. Examples 2 to 41 The light-emitting element was fabricated and evaluated using the compounds listed in Table 1 in the electron transport layer, except that the process was the same as in Example 1. Comparative Examples 1 to 8 The light-emitting element was fabricated and evaluated using the compounds listed in Table 1 in the electron transport layer, except otherwise described in Example 1. C-1 to C-7 and HB-1 are the compounds shown below. Examples 42 to 45 Compound C-4 was used in the electron transport layer, and compound HB-1 was used in the hole blocking layer. Otherwise, the process was the same as in Example 1 to fabricate a light-emitting element. After fabrication, the compounds listed in Table 1 were deposited as charge-generating layers. Then, the same light-emitting element was deposited again to fabricate a tandem device, which was then evaluated. Comparative Example 9 Compound C-4 was used in the electron transport layer and compound HB-1 was used in the hole blocking layer. Otherwise, the same procedure as in Example 1 was followed to fabricate a light-emitting element. After fabrication, Alq3 was deposited as the charge generation layer compound, and then the same light-emitting element was deposited to fabricate a tandem device for evaluation. Comparative Examples 1 and 2 are commercially available propylene oxyhydroxide and propylene oxyhydroxide-like materials. While Comparative Example 1 has high efficiency, it suffers from high voltage and short lifespan. Comparative Example 2, while having a long lifespan, has relatively low efficiency. Comparative Examples 3 and 4 are commercially leading electron transport materials. Comparative Example 3 has low voltage and high efficiency, but a very short lifespan. Comparative Example 4 has high efficiency, but also high voltage and a short lifespan. The device performance exhibits a bottleneck effect, which severely impacts practical applications. Comparative Examples 5 and 6 are some previously studied propylene oxyhydroxide materials. Comparative Example 5 has a low voltage, but also low lifespan and efficiency. Furthermore, Comparative Example 5 is inherently unstable and sometimes decomposes during sublimation, making it difficult to fabricate devices and reducing yield. Comparative Example 6 has a relatively long lifespan, but a slightly higher voltage and very low efficiency. The materials in Examples 1-31 are superior to Comparative Examples 1-6 in overall performance and can perform better as devices. Comparing Examples 1, 21, and 22, it can be observed that reducing the number of propylene glycol groups leads to an excessively deeper molecular orbital energy level, improving the matching with the electron injection layer material, resulting in a decrease in voltage and an increase in lifetime. In particular, with a preferred number of propylene glycol groups, both voltage and lifetime are significantly improved. Furthermore, with a preferred number of propylene glycol groups, material vapor deposition is also easier. Comparing Examples 6 and 23, it can be observed that reducing the number of azirbenzene groups leads to an excessively deeper molecular orbital energy level, improving the matching with the electron injection layer material, resulting in a decrease in voltage and an increase in lifetime. In particular, with a preferred number of azirbenzene groups, both voltage and lifetime are significantly improved. Furthermore, with a preferred number of azirbenzene groups, material deposition is also easier. While the tendency is similar to that shown by propylene oxide groups, the reduction of azirbenzene groups has a stronger effect on device performance optimization than propylene oxide groups. Comparing Examples 6, 9, 10, 24, and 25, it is evident that when the azabenzene host contains nitrogen atoms, the increased number of electrons in the overall molecule leads to improved device efficiency due to the increased electron availability. When the central portion of the azabenzene host lacks nitrogen, the efficiency is very low. While containing one nitrogen atom provides a higher efficiency than the nitrogen-free case, it still lacks a significant advantage. Four nitrogen atoms result in excessively deep energy levels and high voltages. Preferably, when the central portion of the azabenzene host contains two nitrogen atoms (pyrimidine) or three nitrogen atoms (triazine), a good balance is achieved between improved efficiency and low voltage. Two nitrogen atoms in the central portion exhibit higher efficiency, while three nitrogen atoms demonstrate a longer lifetime. This tendency is also reflected in Examples 26-31. Comparing Examples 11-14 with Comparative Example 7, it can be seen that the voltage, efficiency and lifetime of the diphenyltriphenylene-propylene complex connected by two metaphenyl groups are not ideal. However, when the aziridine host is changed to a pyrimidine and / or the phenyl group is changed to a biphenyl group, the voltage can be reduced and the efficiency and lifetime can be improved. Comparing Examples 6, 16, and 26-31, it can be seen that introducing ortho-benzene into the molecule can shorten the distance between the propadiene pyroxene host and the azirbenzene host, enhance the electron handling capability, thereby improving its electrical performance, reducing voltage, and increasing efficiency, and the effect is very significant. Comparing Examples 6 and 16, it is evident that when the substituents of the azirbenzene host are benzene and biphenyl, efficiency and lifetime are improved compared to two benzenes, although the voltage is slightly increased. Furthermore, the compound used in Example 6, due to its more symmetrical azirbenzene host, is more prone to pore blockage during vapor deposition, leading to decreased yield and slower production. Example 16, which improved the asymmetry of the azirbenzene host, exhibits better production performance. Further comparing Examples 26, 29, 32, and 33, it is seen that introducing ortho-substituents to further enhance electronic processing capabilities further reduces voltage, improves efficiency, and increases lifetime for benzene and biphenyl-substituted azirbenzene hosts, while the increase in voltage for bisbenzene materials is smaller. Besides compatibility with surrounding materials, the steric hindrance effect of biphenyl restricts the rotation of the azirbenzene host, thereby strengthening the stability of the delocalized large π bond and enhancing electronic processing performance, which is also a crucial factor. By comparing Examples 16, 18 and Comparative Example 5, it can be seen that when nitrogen-containing substituents are used to replace the azirbenzene host, the efficiency is reduced due to excessive energy level adjustment and mismatch with the surrounding layer material. By comparing Examples 16 and 18 with Comparative Example 6, it can be seen that when a fused ring is attached to the azirbenzene host, the fused ring will disrupt the regular electron movement brought about by the propylene fusion, reduce the electron handling capability of the molecule, and thus improve the voltage reduction efficiency. As can be seen from the comparison between Examples 29-31 and Examples 34-36, increasing the length of the benzene ring in L1 and L2 increases the length of the large Π bond, thereby further improving the performance. By comparing Examples 37-41 with Comparative Examples 4 and 8, it can be seen that the propylene compounds provided by the present invention are specialized for electrons, thus reducing the ability to process holes. When used as a hole blocking layer, compared with common hole blocking materials HB-1 and compound C-7, they can effectively prevent holes from passing through, improve efficiency, and extend lifespan. Comparing Examples 42-45 with Comparative Example 9, it is evident that the propylene oxyacetylene compounds provided by this invention, when used as charge generation layer materials, can achieve lower voltage, higher efficiency, and longer lifetime than the common charge generation layer material Alq3. However, it should be noted that the device's performance is not a linear superposition of the properties of each layer, but rather a combination of multiple layers. Therefore, when the surrounding materials change, there will be a corresponding optimal electron transport layer material. Thus, this invention provides a series of materials for molecular tuning to suit different practical devices.

Claims

1. A propylene oxyacetyl derivative having the structure shown in formula 1 or formulas 73, 74, 75, 150, 151, 152, 168, 169 or 170: L1 is a substituted phenyl group; L2 is a single bond, a substituted phenyl group, or a substituted heteroaryl group; at least one of L1 and L2 is an o-phenyl group; X1, X2, X3, X4, and X5 are the same or different, and each is independently N or C-R1, wherein, The number of N atoms in X1, X2, X3, X4, and X5 is 2 or 3, X2 is C-(Ph)n5, X4 is C-(Ph)n6, Ph is phenyl, and n5+n6>2; R1 is independently selected from one or more of hydrogen, deuterium, substituted alkyl, substituted cycloalkyl, substituted heterocyclic, substituted alkenyl, substituted cycloalkenyl, substituted alkynyl, substituted alkoxy, substituted alkylthio, substituted aryl ether, substituted aryl thioether, substituted aryl, substituted heteroaryl, substituted carbonyl, substituted carboxyl, substituted oxycarbonyl, substituted aminomethyl, substituted silyl, substituted alkylamine, or substituted arylamine; n1 and n4 are integers from 1 to 3; n2 and n3 are integers from 0 to 3, but not both simultaneously 0.

2. As in claim 1, a propylene oxyacetate derivative, wherein, In the general formula 1, n1=1 and n4=1.

3. As in claim 1, a propylene oxyacetate derivative, wherein, In the general formula 1, when n1=1, the value of n1×n2+n3×n4 is an integer from 1 to 5.

4. As in claim 1, a propylene oxyacetate derivative, wherein, In the general formula 1, when n1=1, the value of n1×n2+n3×n4 is an integer between 2 and 3.

5. As in claim 1, a polypropylene derivative, wherein, In C-R1, R1 is selected from substituted phenyl, substituted dibenzofuranyl, substituted carbazoyl, substituted fumonyl, and substituted dibenzothiopheneyl.

6. The allene-based derivative of claim 1, wherein, n5 is not equal to n6.

7. The allene oxypropene derivative as claimed in claim 1, wherein, L1 and L2 are each independently selected from phenylene, but L1 and L2 are not simultaneously metaphenylene.

8. The allene oxygenate derivative of claim 1 is selected from the following compounds.

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

10. The light-emitting element as claimed in claim 9, wherein, The organic layer is a layer responsible for processing electrons or holes, and the organic layer contains any one of claims 1 to 8 of the propylene syndiol derivative.

11. The light-emitting element as claimed in claim 9, wherein, The organic layer has an electron transport layer containing any one of claims 1 to 8 of the propylene syndiol derivative.

12. The light-emitting element as described in claim 9, wherein, The organic layer has an electron-generating layer containing any one of claims 1 to 8 of the propylene syndiol derivative.

13. The light-emitting element as described in claim 9, wherein, The organic layer has a hole-blocking layer containing any one of claims 1 to 8 of the propylene syndiol derivative.

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

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