Organic compound and organic electroluminescent element comprising the same

Abstract

This invention relates to a novel organic compound and an organic electroluminescent element utilizing the same, and more specifically, to an organic compound with excellent electron injection, transport capability and thermal stability, and an organic electroluminescent element whose luminous efficiency, driving voltage, lifetime and other characteristics are improved by including it in one or more organic layers.

Description

Technical Field

[0001] This invention relates to a novel organic compound and an organic electroluminescent element comprising the same, and more specifically, to an organic compound with excellent electron injection, transport capability and thermal stability, and an organic electroluminescent element whose luminous efficiency, driving voltage, lifetime and other characteristics are improved by including the compound in one or more organic layers. Background Technology

[0002] When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as "organic EL device"), holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, they form excitons. When these excitons transition to the ground state, they emit light. The materials used as the organic layer can be classified according to their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0003] The light-emitting layer materials of organic EL devices can be categorized into blue, green, and red light-emitting materials based on their emission color. In addition, yellow and orange light-emitting materials are used to achieve more natural colors. Furthermore, to improve luminous efficiency through increased color purity and energy transfer, a host / dopant system can be used as the light-emitting material. Dopants can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of such phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, not only phosphorescent dopants but also phosphorescent host materials are attracting considerable attention.

[0004] To date, NPB, BCP, Alq3, and other materials represented by the following chemical formulas are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Regarding luminescent materials, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, phosphorescent materials, such as Ir-containing metal coordination compounds like Firmic, Ir(ppy)3, and (acac)Ir(btp)2, which offer significant advantages in improving efficiency, have been used as blue, green, and red dopants. To date, CBP has shown excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperature and poor thermal stability have resulted in unsatisfactory lifetime performance in organic EL devices. Therefore, there is a need to develop high-performance organic layer materials. Summary of the Invention

[0006] Technical issues

[0007] The technical challenge of this invention is to provide an organic layer material with excellent heat resistance, charge carrier transport capability, and light emission capability, which can be used as an organic electroluminescent element, specifically a novel compound that can be used as an electron transport layer, an electron transport auxiliary layer, or a light emission layer.

[0008] Furthermore, another technical challenge of the present invention is to provide an organic electroluminescent element comprising the above-mentioned novel compound, thereby exhibiting low driving voltage, high luminous efficiency, and improved lifetime.

[0009] Other objects and advantages of the present invention can be more clearly set forth in the following detailed description of the invention and the claims.

[0010] Technical solution

[0011] To achieve the above objectives, the present invention provides an organic compound selected from the group consisting of compounds 1 to 41:

[0012]

[0013] .

[0014] Furthermore, the present invention provides an organic electroluminescent element comprising: an anode; a cathode; and one or more organic layers between the anode and the cathode, wherein at least one of the organic layers comprises the aforementioned organic compound.

[0015] As an example, the organic layer containing the above-mentioned organic compounds can be an electron transport layer and / or an electron transport auxiliary layer.

[0016] The effects of the invention

[0017] According to an embodiment of the present invention, compounds selected from the group consisting of compounds 1 to 41 are used as organic layer materials for organic electroluminescent elements due to their excellent electron transport capability, luminescence capability, heat resistance, etc.

[0018] In particular, when the compounds of the present invention are used as electron transport layer or electron transport auxiliary layer materials, they can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency and long lifetime characteristics compared with components that use conventional host materials or electron transport materials.

[0019] Therefore, organic electroluminescent elements containing the compounds of the present invention can be significantly improved in terms of excellent luminescence performance, low driving voltage, long lifespan and high efficiency, and can thus be effectively applied to full-color display panels, etc.

[0020] The effects of the present invention are not limited to those illustrated above, and this specification includes a wider variety of effects. Detailed Implementation

[0021] The present invention will now be described in detail.

[0022] <Novel Organic Compounds>

[0023] The compounds of the present invention are selected from the group consisting of compounds 1 to 41 above. Such compounds have a cyano group substituted on a 9,9-dimethyl-9H-fluorene group, said fluorene group being bonded to a heteroaromatic cyclic group containing 2 to 3 nitrogen atoms (e.g., triazine, pyrimidinyl) via a linking group. In this case, the compounds of the present invention have a structure in which the linking group is an ortho-phenylene or meta-phenylene, or the above-mentioned nitrogen-containing heteroaromatic cyclic group is substituted with a naphthyl, [1,1'-biphenyl]-2-yl ([1,1'-biphenyl]-2-yl) substituent, or an ortho-terphenyl group.

[0024] Specifically, the compounds of the present invention, by directly bonding a cyano group to a 9,9-dimethyl-9H-fluorenyl group, modulate the LUMO energy level, enabling electrons to be effectively injected from the cathode into the electron transport layer. Thus, the electron-withdrawing group (EWG) characteristics of the compounds of the present invention are improved, resulting in excellent electron injection characteristics. Therefore, unlike conventional electron transport layer materials that suffer from insufficient electron injection characteristics leading to reduced driving voltage, these compounds can achieve low-voltage driving characteristics for devices.

[0025] Furthermore, the compounds of the present invention improve molecular rigidity by including an o-phenyl group as a linking group between the 9,9-dimethyl-9H-fluorenyl group and the nitrogen-containing heteroaromatic ring, or by substituting the nitrogen-containing heteroaromatic ring with a naphthyl, [1,1'-biphenyl]-2-yl, or o-terphenyl. Due to these structural features, the recombination energy (λ) of the molecules of the compounds of the present invention is reduced, and the charge migration rate is increased, thereby exhibiting physicochemical properties more suitable for electron injection and electron transport. In addition, the increased molecular stability of the compounds of the present invention enables the achievement of long-lifetime characteristics in devices.

[0026] Furthermore, the compounds of the present invention, by limiting the linking group between the 9,9-dimethyl-9H-fluorene group and the nitrogen-containing heteroaromatic ring group to ortho-phenylene or meta-phenylene, can shorten the intramolecular conjugation length and induce strong π-π overlap compared to conventional compounds with a p-phenylene linking group, thereby enabling low-voltage drive of the device. In this case, by substituting the aforementioned nitrogen-containing heteroaromatic ring group with a naphthyl group, the charge transfer characteristics can be further maximized. Moreover, when the linking group is meta-phenyl, by substituting the aforementioned nitrogen-containing heteroaromatic ring group with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an ortho-terphenyl group, the drive voltage and efficiency characteristics of the device can be improved compared to conventional compounds with a p-, p-biphenyl group.

[0027] Furthermore, by substituting the aforementioned nitrogen-containing heteroaromatic cyclic group with naphthyl or [1,1'-biphenyl]-2-yl substituents or o-terphenyl, the molecular weight is increased, thereby improving the thermal stability of the element.

[0028] Furthermore, the compounds of this invention are designed with the 9,9-dimethyl-9H-fluorenyl group and the nitrogen-containing heteroaromatic ring group bonded at the ortho- or meta- position, thereby possessing a high triplet energy level (T1). Therefore, unlike compounds bonded at the para- position, they can block the diffusion (migration) of excitons generated in the luminescent layer to adjacent electron transport layers or hole transport layers. Thus, not only can the number of excitons contributing to luminescence be increased, but the exciton-blocking properties of this compound can also be used to confine luminescence to the desired region of the device. Therefore, the compounds of this invention can improve the luminescence efficiency of the device and achieve a longer lifetime by improving the device's durability and stability.

[0029] As previously stated, when the compounds of the present invention are used as organic layer materials in organic electroluminescent elements, specifically as luminescent layer materials (blue, green, and / or red phosphorescent host materials), electron transport layer / injection layer materials, hole transport layer / injection layer materials, luminescent auxiliary layer materials, and lifetime improvement layer materials, the performance and lifetime characteristics of the organic electroluminescent elements can be significantly improved. Preferably, when the compounds of the present invention are used as electron transport layer or electron transport auxiliary layer materials, significant and excellent performance improvements in terms of element efficiency, driving voltage, and lifetime characteristics can be expected. In particular, when the compounds of the present invention are used as electron transport layer or electron transport auxiliary layer materials as common layers in organic electroluminescent elements, the performance of the luminescent layer, specifically the blue luminescent layer, and the organic electroluminescent element incorporating it can be improved. Such organic electroluminescent elements ultimately enable the maximization of the performance of full-color organic light-emitting panels.

[0030] <Electron Transport Layer Materials>

[0031] The present invention provides an electron transport layer comprising a compound selected from the group consisting of compounds 1 to 41 described above.

[0032] The aforementioned electron transport layer (ETL) serves to move electrons injected from the cathode to adjacent layers, specifically to the light-emitting layer.

[0033] The above compounds can be used alone as electron transport layer (ETL) materials or in combination with electron transport layer materials known in the art. Use alone is preferred.

[0034] Electron transport layer materials that can be mixed with the above-mentioned compounds include electron transport substances generally known in the art. Non-limiting examples of usable electron transport substances include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3, tris(8-quinolinolato)-aluminium, BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. They can be used alone or in combination of two or more.

[0035] In this invention, when the above-mentioned compounds are mixed with electron transport layer materials, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0036] <Electron Transport Auxiliary Layer Materials>

[0037] Furthermore, the present invention provides an electron transport auxiliary layer comprising a compound selected from the group consisting of compounds 1 to 41 described above.

[0038] The electron transport auxiliary layer is disposed between the light-emitting layer and the electron transport layer, and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0039] The above compounds can be used alone as electron transport auxiliary layer materials, or they can be used in combination with electron transport layer materials known in the art. Use alone is preferred.

[0040] Electron transport assist layer materials that can be used in conjunction with the above-mentioned compounds include electron transport substances generally known in the art. For example, the electron transport assist layer may comprise oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0041] In this invention, when the above-mentioned compounds are mixed with electron transport auxiliary layer materials, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0042] Organic electroluminescent elements

[0043] On the other hand, the present invention provides an organic electroluminescent element (hereinafter referred to as "organic EL element") comprising an organic compound selected from the group consisting of the aforementioned compounds 1 to 41.

[0044] Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the organic layers comprises any one of compounds 1 to 41 described above. In this case, the compounds may be used alone or in combination of two or more.

[0045] The one or more organic layers can be any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, wherein at least one organic layer contains any one of the compounds 1 to 41 mentioned above. Specifically, the organic layer containing the above compounds is preferably the phosphorescent host material of the light-emitting layer, the electron transport material of the electron transport layer, or the electron transport auxiliary layer.

[0046] The light-emitting layer of the organic electroluminescent element of the present invention comprises a host material and a dopant material, wherein the aforementioned compound may be included as the host material. Furthermore, the light-emitting layer of the present invention may include compounds known in the art, other than those described above, as the host material.

[0047] When the above-mentioned compounds are used as the light-emitting layer material of an organic electroluminescent element, preferably as a blue, green, or red phosphorescent host material, the efficiency (luminous efficiency and power efficiency), lifetime, brightness, and driving voltage of the organic electroluminescent element can be improved due to the increased binding force between holes and electrons in the light-emitting layer. Specifically, the above-mentioned compounds are preferably included in the organic electroluminescent element as a green and / or red phosphorescent host, fluorescent host, or dopant material.

[0048] The structure of the organic electroluminescent element of the present invention is not particularly limited, and can be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked, and optionally, an electron transport auxiliary layer may also be included. In this case, one or more of the aforementioned hole injection layer, hole transport layer, light-emitting auxiliary layer, light-emitting layer, electron transport auxiliary layer, electron transport layer, and electron injection layer may contain any one of the compounds 1 to 41. Preferably, the light-emitting layer (e.g., the host), the electron transport layer, or the electron transport auxiliary layer, more preferably, the electron transport layer or the electron transport auxiliary layer contains any one of the compounds 1 to 41. On the other hand, an electron injection layer may be further stacked on the aforementioned electron transport layer.

[0049] The organic electroluminescent element of the present invention can be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0050] In the organic electroluminescent element of the present invention, one or more of the aforementioned organic layers contain the above-mentioned compounds. In addition, the organic layers and electrodes can be formed and manufactured using materials and methods known in the art.

[0051] The aforementioned organic layer can be formed by vacuum evaporation or solution coating. Examples of solution coating methods include spin coating, dip coating, doctor blade coating, inkjet printing, or thermal transfer, but are not limited to these.

[0052] The substrate used in manufacturing the organic electroluminescent element of the present invention is not particularly limited, and for example, silicone wafers, quartz, glass plates, metal plates, plastic films and sheets can be used.

[0053] Furthermore, the anode material can be any anode material known in the art without restriction. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxothiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but not limited thereto.

[0054] Furthermore, cathode materials known in the art can be used without restriction. Examples include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead; and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0055] Furthermore, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and commonly known materials in the art can be used without restriction.

[0056] The present invention will be described in detail below through embodiments. However, the following embodiments are merely illustrative of the present invention, and the present invention is not limited to the following embodiments.

[0057] [Synthesis Example 1] Synthesis of Compound 1

[0058]

[0059] The following substances were added: 25 g (59.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine), 24.7 g (71.4 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile (9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile), 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, and Xphos. 2.3 g (4.8 mmol, 0.08 eq) and 16.5 g (119.1 mmol, 2 eq) of K₂CO₃ were added to 375 mL of toluene, 100 mL of EtOH, and 100 mL of H₂O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water. The solution was then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in an EA / HX system to obtain white crystals. The crystals were filtered to obtain target compound 1, namely 7-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (27.3 g, yield 76%).

[0060] Mass spectrometry: [(M+H)]+ ]:602.74

[0061] [Synthesis Example 2] Synthesis of Compound 2

[0062]

[0063] Add 25g (59.5mmol, 1eq) of 2-([1,1'-biphenyl]-3-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-3-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine), 24.7g (71.4mmol, 1.2eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 20.5g (2.4mmol, 0.04eq) of Pd(OAc), 2.3g (4.8mmol, 0.08eq) of Xphos, and 16.5g (119.1mmol, 2eq) of K2CO3 to 375ml of toluene, 100ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 2, namely 7-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (28.4 g, yield 79%).

[0064] Mass spectrometry: [(M+H)] + ]:602.74

[0065] [Synthesis Example 3] Synthesis of Compound 3

[0066]

[0067] Add 25 g (59.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine), 24.7 g (71.4 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.1 mmol, 2 eq) of K2CO3 to 375 ml of toluene and EtOH. The mixture was heated under reflux for 6 hours with 100 ml of H2O. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 3, namely 7-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (29.4 g, yield 82%).

[0068] Mass spectrometry: [(M+H)] + ]:602.74

[0069] [Synthetic Example 4] Synthesis of Compound 4

[0070]

[0071] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.6 g (2.5 mmol, 0.04 eq) of Pd(OAc)2, 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 17.5 g (127.0 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 4, namely 9,9-dimethyl-7-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-fluorene-2-carbonitrile (25.6 g, yield 70%).

[0072] Mass spectrometry: [(M+H)] + ]:576.70

[0073] [Synthetic Example 5] Synthesis of Compound 5

[0074]

[0075] 25 g (56.3 mmol, 1 eq) of 2-(2-chlorophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine, 23.3 g (67.7 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 20.5 g (2.3 mmol, 0.04 eq) of Pd(OAc), 2.1 g (4.5 mmol, 0.08 eq) of Xphos, and 15.6 g (112.6 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 5, namely 7-(2-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (24.0 g, yield 68%).

[0076] Mass spectrometry: [(M+H)] + ]:626.76

[0077] [Synthesis Example 6] Synthesis of Compound 6

[0078]

[0079] 25 g (59.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-3-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine, 24.7 g (71.4 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 0.08 g (4.8 mmol, 0.08 eq) of K2CO3 were added. 16.5 g (119.1 mmol, 2 eq) was added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 6, namely 6-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (6-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (27.3 g, yield 76%).

[0080] Mass spectrometry: [(M+H)] + ]:602.74

[0081] [Synthesis Example 7] Synthesis of Compound 7

[0082]

[0083] 25 g (59.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine, 24.7 g (71.4 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.1 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O and heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 7, namely 6-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (6-(2-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (24.4 g, yield 68%).

[0084] Mass spectrometry: [(M+H)] + ]:602.74

[0085] [Synthetic Example 8] Synthesis of Compound 8

[0086]

[0087] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine, 26.3 g (76.1 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.6 g (2.5 mmol, 0.04 eq) of Pd(OAc)2, 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 17.5 g (119.1 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. The mixture was stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 8, namely 9,9-dimethyl-6-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-fluorene-2-carbonitrile (23.8 g, yield 65%).

[0088] Mass spectrometry: [(M+H)] + ]:576.7

[0089] [Synthetic Example 9] Synthesis of Compound 9

[0090]

[0091] Add 25 g (59.7 mmol, 1 eq) of 4-([1,1'-biphenyl]-3-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (4-([1,1'-biphenyl]-3-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine), 24.7 g (71.6 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.4 mmol, 2 eq) of K2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 mL. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 9, namely 7-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (25.9 g, yield 72%).

[0092] Mass spectrometry: [(M+H)] + ]:601.75

[0093] [Synthetic Example 10] Synthesis of Compound 10

[0094]

[0095] Add 25 g (59.7 mmol, 1 eq) of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine), 24.7 g (71.6 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.4 mmol, 2 eq) of K2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 10, namely 7-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (27.3 g, yield 76%).

[0096] Mass spectrometry: [(M+H)] + ]:601.75

[0097] [Synthetic Example 11] Synthesis of Compound 11

[0098]

[0099] Add 25 g (59.7 mmol, 1 eq) of 4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine (4-([1,1'-biphenyl]-4-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine), 24.7 g (71.6 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.4 mmol, 2 eq) of K2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 mL. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 11, namely 7-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenylpyrimidin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (26.2 g, yield 73%).

[0100] Mass spectrometry: [(M+H)] + ]:601.75

[0101] [Synthetic Example 12] Synthesis of Compound 12

[0102]

[0103] 25 g (59.7 mmol, 1 eq) of 4-(2-chlorophenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine, 24.7 g (71.6 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.5 g (119.4 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 12, namely 9,9-dimethyl-7-(2-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)phenyl)-9H-fluorene-2-carbonitrile (23.1 g, yield 63%).

[0104] Mass spectrometry: [(M+H)] + ]:575.72

[0105] [Synthetic Example 13] Synthesis of Compound 13

[0106]

[0107] Add 25.2 g (60.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine) to 380 ml of toluene and EtOH. Also add 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2 (2.4 mmol, 0.04 eq), 2.3 g (4.8 mmol, 0.08 eq) of Xphos and 16.6 g (120.0 mmol, 2 eq) of Xphos to 380 ml of toluene and EtOH. The mixture was heated under reflux for 6 hours with 100 ml of H2O. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 13, namely 7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (27.8 g, yield 77%).

[0108] Mass spectrometry: [(M+H)] + ]:603.26

[0109] [Synthetic Example 14] Synthesis of Compound 14

[0110]

[0111] Add 23.6 g (60.0 mmol, 1 eq) of 2-(3-chlorophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine, 24.9 g (72.0 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.6 g (120.0 mmol, 2 eq) of K2CO3 to 380 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 14, namely 9,9-dimethyl-7-(3-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-fluorene-2-carbonitrile (23.8 g, yield 69%).

[0112] Mass spectrometry: [(M+H)] + ]:577.23

[0113] [Synthetic Example 15] Synthesis of Compound 15

[0114]

[0115] 23.6 g (60.0 mmol, 1 eq) of 2-(3-chlorophenyl)-4-(naphth-1-yl)-6-phenyl-1,3,5-triazine, 24.9 g (72.0 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.6 g (120.0 mmol, 2 eq) of K2CO3 were added to 380 ml of toluene and EtOH. The mixture was heated under reflux for 6 hours with 100 ml of H2O and 100 ml of water. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 15, namely 9,9-dimethyl-6-(3-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-fluorene-3-carbonitrile (24.9 g, yield 72%).

[0116] Mass spectrometry: [(M+H)] + ]:577.24

[0117] [Synthetic Example 16] Synthesis of Compound 16

[0118]

[0119] Add 29.5 g (75.0 mmol, 1 eq) of 2-(3-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine, 31.1 g (90.0 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-3-carboxynitrile, 0.7 g (3.0 mmol, 0.04 eq) of Pd(OAc)2, 2.9 g (6.0 mmol, 0.08 eq) of Xphos, and 20.7 g (150.0 mmol, 2 eq) of K2CO3 to 475 ml of toluene, 125 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 8 hours in 125 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 16, namely 9,9-dimethyl-6-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-fluorene-3-carbonitrile (32.0 g, yield 74%).

[0120] Mass spectrometry: [(M+H)] + ]:577.23

[0121] [Synthetic Example 17] Synthesis of Compound 17

[0122]

[0123] The following substances were added: 31.5 g (75.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine; 31.1 g (90.0 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile; 0.7 g (3.0 mmol, 0.04 eq) of Pd(OAc)2; 2.9 g (6.0 mmol, 0.08 eq) of Xphos; and K2CO3. 20.7 g (150.0 mmol, 2 eq) was added to 475 ml of toluene, 125 ml of EtOH, and 125 ml of H2O, and the mixture was heated under reflux and stirred for 8 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 17, namely 7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-3-carbonitrile (7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-3-carbonitrile) (30.7 g, yield 68%).

[0124] Mass spectrometry: [(M+H)] + ]:603.25

[0125] [Synthetic Example 18] Synthesis of Compound 18

[0126]

[0127] The following substances were added: 31.5 g (75.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine; 31.1 g (90.0 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-4-carbonitrile; 0.7 g (3.0 mmol, 0.04 eq) of Pd(OAc)2; 2.9 g (6.0 mmol, 0.08 eq) of Xphos; and K2CO3. 20.7 g (150.0 mmol, 2 eq) was added to 475 ml of toluene, 125 ml of EtOH, and 125 ml of H2O, and the mixture was heated under reflux and stirred for 8 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 18, namely 7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-4-carbonitrile (7-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-4-carbonitrile) (33.0 g, yield 73%).

[0128] Mass spectrometry: [(M+H)] + ]:603.25

[0129] [Synthetic Example 19] Synthesis of Compound 19

[0130]

[0131] 31.5 g (75.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 31.1 g (90.0 mmol, 1.2 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.7 g (3.0 mmol, 0.04 eq) of Pd(OAc)2, 2.9 g (6.0 mmol, 0.08 eq) of Xphos, and 20.7 g (150.0 mmol, 2 eq) of K2CO3 were added to 475 ml of toluene, 125 ml of EtOH, and 125 ml of H2O and heated under reflux with stirring for 8 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 19, namely 6-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (6-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (34.4 g, yield 76%).

[0132] Mass spectrometry: [(M+H)] + ]:603.25

[0133] [Synthetic Example 20] Synthesis of Compound 20

[0134]

[0135] The following substances were added: 25.2 g (60.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine; 24.9 g (72.0 mmol, 1 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-4-carbonitrile; 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2; 2.3 g (4.8 mmol, 0.08 eq) of Xphos; and K2CO3. 16.6 g (120.0 mmol, 2 eq) was added to 380 mL of toluene, 100 mL of EtOH, and 100 mL of H₂O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 20, namely 6-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-4-carbonitrile (6-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-4-carbonitrile) (26.4 g, yield 73%).

[0136] Mass spectrometry: [(M+H)] + ]:603.24

[0137] [Synthetic Example 21] Synthesis of Compound 21

[0138]

[0139] The following substances were added: 25.2 g (60.0 mmol, 1 eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine; 24.9 g (72.0 mmol, 1 eq) of 9,9-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile; 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2; 2.3 g (4.8 mmol, 0.08 eq) of Xphos; and K2CO3. 16.6 g (120.0 mmol, 2 eq) was added to 380 mL of toluene, 100 mL of EtOH, and 100 mL of H₂O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 21, namely 5-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (5-(3-(4-([1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (25.3 g, yield 70%).

[0140] Mass spectrometry: [(M+H)] + ]:603.25

[0141] [Synthetic Example 22] Synthesis of Compound 22

[0142]

[0143] Add 25.1 g (60.0 mmol, 1 eq) of 4-([1,1'-biphenyl]-2-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine (4-([1,1'-biphenyl]-2-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine), 24.9 g (72.0 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.4 mmol, 0.04 eq) of Pd(OAc)2, 2.3 g (4.8 mmol, 0.08 eq) of Xphos, and 16.6 g (120.0 mmol, 2 eq) of K2CO3 to 380 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 22, namely 7-(3-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile (7-(3-(6-([1,1'-biphenyl]-2-yl)-2-phenylpyrimidin-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-carbonitrile) (25.6 g, yield 71%).

[0144] Mass spectrometry: [(M+H)] + ]:602.26

[0145] [Synthetic Example 23] Synthesis of Compound 23

[0146]

[0147] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine, 21.9 g (63.5 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-3-carboxynitrile, 0.6 g (2.5 mmol, 0.04 eq) of Pd(OAc)2, 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 41.4 g (126.9 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 23 (28 g, yield 75%).

[0148] Mass spectrometry: [(M+H)] + ]:576.70

[0149] [Synthetic Example 24] Synthesis of Compound 24

[0150]

[0151] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine, 21.9 g (63.5 mmol, 1.0 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.6 g (2.5 mmol, 0.04 eq) of Pd(OAc)2, 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 41.4 g (126.9 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and the mixture was heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give target compound 24 (29 g, yield 78%).

[0152] Mass spectrometry: [(M+H)] + ]:576.70

[0153] [Synthetic Example 25] Synthesis of Compound 25

[0154]

[0155] Add 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(2-phenylnaphthalen-1-yl)-1,3,5-triazine (2-(2-chlorophenyl)-4-phenyl-6-(2-phenylnaphthalen-1-yl)-1,3,5-triazine), 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronacecyclopentan-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 25 (26 g, yield 72%).

[0156] Mass spectrometry: [(M+H)] + ]:652.80

[0157] [Synthetic Example 26] Synthesis of Compound 26

[0158]

[0159] Add 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(1-phenylnaphthalen-2-yl)-1,3,5-triazine (2-(2-chlorophenyl)-4-phenyl-6-(1-phenylnaphthalen-2-yl)-1,3,5-triazine), 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 26 (26 g, yield 74%).

[0160] Mass spectrometry: [(M+H)] + ]:652.80

[0161] [Synthetic Example 27] Synthesis of Compound 27

[0162]

[0163] 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(2-phenylnaphth-1-yl)-1,3,5-triazine, 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water. The solution was then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give target compound 27 (26 g, yield 72%).

[0164] Mass spectrometry: [(M+H)] + ]:652.80

[0165] [Synthetic Example 28] Synthesis of Compound 28

[0166]

[0167] 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(1-phenylnaphth-2-yl)-1,3,5-triazine, 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and the mixture was heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 28 (25 g, 70% yield).

[0168] Mass spectrometry: [(M+H)] + ]:652.80

[0169] [Synthetic Example 29] Synthesis of Compound 29

[0170]

[0171] 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(1-phenylnaphth-2-yl)-1,3,5-triazine, 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and the mixture was heated under reflux with stirring for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give target compound 29 (25 g, yield 71%).

[0172] Mass spectrometry: [(M+H)] + ]:652.80

[0173] [Synthetic Example 30] Synthesis of Compound 30

[0174]

[0175] Add 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(3-phenylnaphthalen-2-yl)-1,3,5-triazine (2-(2-chlorophenyl)-4-phenyl-6-(3-phenylnaphthalen-2-yl)-1,3,5-triazine), 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 30 (27 g, yield 75%).

[0176] Mass spectrometry: [(M+H)] + ]:652.80

[0177] [Synthetic Example 31] Synthesis of Compound 31

[0178]

[0179] 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(3-phenylnaphth-2-yl)-1,3,5-triazine, 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain target compound 31 (26 g, yield 72%).

[0180] Mass spectrometry: [(M+H)] + ]:652.80

[0181] [Synthetic Example 32] Synthesis of Compound 32

[0182]

[0183] 25 g (54.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenyl-6-(3-phenylnaphth-2-yl)-1,3,5-triazine, 18.8 g (54.4 mmol, 1.0 eq) of 9,9-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.2 mmol, 0.04 eq) of Pd(OAc)2, 2.1 g (4.3 mmol, 0.08 eq) of Xphos, and 35.4 g (108.7 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give the target compound 32 (26 g, yield 69%).

[0184] Mass spectrometry: [(M+H)] + ]:652.80

[0185] [Synthetic Example 33] Synthesis of Compound 33

[0186]

[0187] 25 g (53.3 mmol, 1 eq) of 4-(2-chlorophenyl)-2-phenyl-6-(2-phenylnaphthalen-1-yl)pyrimidine, 18.4 g (53.3 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.1 mmol, 0.04 eq) of Pd(OAc)2, 2.0 g (4.3 mmol, 0.08 eq) of Xphos, and 34.7 g (106.6 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the compound was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 33 (26 g, yield 75%).

[0188] Mass spectrometry: [(M+H)] + ]:651.81

[0189] [Synthetic Example 34] Synthesis of Compound 34

[0190]

[0191] 25 g (53.3 mmol, 1 eq) of 4-(2-chlorophenyl)-2-phenyl-6-(1-phenylnaphthalen-2-yl)pyrimidine, 18.4 g (53.3 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.1 mmol, 0.04 eq) of Pd(OAc)2, 2.0 g (4.3 mmol, 0.08 eq) of Xphos, and 34.7 g (106.6 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the compound was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 34 (25 g, yield 72%).

[0192] Mass spectrometry: [(M+H)] + ]:651.81

[0193] [Synthetic Example 35] Synthesis of Compound 35

[0194]

[0195] 25 g (53.3 mmol, 1 eq) of 4-(2-chlorophenyl)-2-phenyl-6-(3-phenylnaphthalen-2-yl)pyrimidine, 18.4 g (53.3 mmol, 1.0 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.1 mmol, 0.04 eq) of Pd(OAc)2, 2.0 g (4.3 mmol, 0.08 eq) of Xphos, and 34.7 g (106.6 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the compound was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 35 (25 g, yield 72%).

[0196] Mass spectrometry: [(M+H)] + ]:651.81

[0197] [Synthetic Example 36] Synthesis of Compound 36

[0198]

[0199] 25 g (53.3 mmol, 1 eq) of 4-(2-chlorophenyl)-2-phenyl-6-(3-phenylnaphth-2-yl)pyrimidine, 18.4 g (53.3 mmol, 1.0 eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 0.5 g (2.1 mmol, 0.04 eq) of Pd(OAc)2, 2.0 g (4.3 mmol, 0.08 eq) of Xphos, and 34.7 g (106.6 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give the target compound 36 (26 g, yield 74%).

[0200] Mass spectrometry: [(M+H)]+ ]:651.81

[0201] [Synthetic Example 37] Synthesis of Compound 37

[0202]

[0203] Add 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 30.3 g (72.4 mmol, 1 eq) of 4-([1,1'-biphenyl]-3-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine, 0.7 g (2.9 mmol, 0.04 eq) of Pd(OAc)2, 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 37 (34 g, yield 78%).

[0204] Mass spectrometry: [(M+H)] + ]:607.75

[0205] [Synthetic Example 38] Synthesis of Compound 38

[0206]

[0207] 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 35.9 g (72.4 mmol, 1 eq) of 2-([1,1':2',1''-terphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1':2',1''-terphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine), 0.7 g (2.9 mmol, 0.04 eq) of Pd(OAc)2, 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and Cs2CO3 were added. 47.2 g (144.8 mmol, 2 eq) was added to 375 mL of toluene, 100 mL of EtOH, and 100 mL of H₂O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 38 (34 g, yield 72%).

[0208] Mass spectrometry: [(M+H)] + ]:678.84

[0209] [Synthetic Example 39] Synthesis of Compound 39

[0210]

[0211] Add 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 35.9 g (72.4 mmol, 1 eq) of 2,4-di([1,1'-biphenyl]-2-yl)-6-(3-chlorophenyl)-1,3,5-triazine (2,4-di([1,1'-biphenyl]-2-yl)-6-(3-chlorophenyl)-1,3,5-triazine), 0.7 g (2.9 mmol, 0.04 eq) of Pd(OAc)2, 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml of water. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 39 (35 g, yield 71%).

[0212] Mass spectrometry: [(M+H)] + ]:678.84

[0213] [Synthetic Example 40] Synthesis of Compound 40

[0214]

[0215] Add 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 34.0 g (72.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(2-(1-naphthalenyl)phenyl)-6-phenyl-1,3,5-triazine (2-(2-chlorophenyl)-4-(2-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine), 0.7 g (2.9 mmol, 0.04 eq) of Pd(OAc)2, 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 to 375 ml of toluene, 100 ml of EtOH, and H2O. The mixture was heated to reflux and stirred for 6 hours in 100 ml. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to give the target compound 40 (34 g, yield 72%).

[0216] Mass spectrometry: [(M+H)] + ]:652.80

[0217] [Synthetic Example 41] Synthesis of Compound 41

[0218]

[0219] 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-9H-fluorene-2-carboxynitrile, 35.9 g (72.4 mmol, 1 eq) of 2-([1,1':2',1''-terphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (2-([1,1':2',1''-terphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine), 0.7 g (2.9 mmol, 0.04 eq) of Pd(OAc)2, 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and Cs2CO3 were added. 47.2 g (144.8 mmol, 2 eq) was added to 375 mL of toluene, 100 mL of EtOH, and 100 mL of H₂O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography with stirring in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 41 (37 g, yield 75%).

[0220] Mass spectrometry: [(M+H)] + ]:678.84

[0221] [Example 1] Fabrication of a blue organic electroluminescent element

[0222] After refining compound 1 synthesized in Synthesis Example 1 to high purity by commonly known methods, a blue organic electroluminescent element was fabricated according to the following procedure.

[0223] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1200 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes. Finally, the substrate was transferred to a vacuum evaporation machine.

[0224] On the ITO transparent electrode prepared above, an organic electroluminescent element is fabricated by stacking the following compounds in the order of HI + 2% HAT-CN6 (10nm) / HI (140nm) / EB (5nm) / BH + 2% BD (20nm) / HB (5nm) / Compound 1 + Liq (1:1) (30nm) / LiF (1nm) / Al (100nm). The structures of HI, HAT-CN6, EB, BH, BD, HB, and Liq used are as follows.

[0225]

[0226] [Examples 2 to 41] Fabrication of Blue Organic Electroluminescent Element

[0227] The blue organic electroluminescent element was fabricated using the substances listed in Table 1 below instead of Compound 1, which was used as the electron transport layer material in Example 1.

[0228] [Comparative Examples 1 to 20] Fabrication of Blue Organic Electroluminescent Element

[0229] The blue organic electroluminescent element was fabricated using ET1 to ET20 instead of compound 1, which was used as the electron transport layer material in Example 1. Otherwise, the process was the same as in Example 1. The ET1 to ET20 used in this case are as follows.

[0230]

[0231] [Evaluation Example 1]

[0232] The current density of the organic electroluminescent elements manufactured in Examples 1 to 41 and Comparative Examples 1 to 20 was measured at 10 mA / cm². 2 The driving voltage, emission wavelength, and current efficiency are shown in Table 1 below.

[0233] [Table 1]

[0234]

[0235]

[0236] As shown in Table 1, it can be confirmed that the blue organic electroluminescent elements of Examples 1 to 41, which use the compounds of the present invention as electron transport layers, exhibit superior driving voltage and current efficiency compared to the organic electroluminescent elements of Comparative Examples 1 to 20, which use conventional electron transport layer materials. Specifically, the compounds of the present invention have a structure in which a cyano group is substituted on a 9,9-dimethyl-9H-fluorenyl group. The blue organic electroluminescent elements of Examples 1 to 41, which use such compounds of the present invention as electron transport layer materials, exhibit superior driving voltage and current efficiency compared to the organic electroluminescent elements of Comparative Examples 1 to 8, which use conventional electron transport layer materials (ET1 to ET8) that do not contain a cyano group or whose cyano group is not substituted on a fluorenyl group.

[0237] Furthermore, it can be confirmed that the compounds of the present invention have the structure in which the above-mentioned fluorene group is bonded to 2 to 3 nitrogen-containing heteroaromatic ring groups via an ortho-phenylene group, or the above-mentioned fluorene group is bonded to 2 to 3 nitrogen-containing heteroaromatic ring groups substituted with naphthyl, [1,1'-biphenyl]-2-yl substituent or ortho-terphenyl group via a meta-phenylene group. The blue organic light-emitting elements of Examples 1-41, which possess such compounds of the present invention as electron transport layer materials, exhibit superior driving voltage, emission peak, and current efficiency compared to the organic light-emitting elements of the comparative examples. These comparative examples are: Comparative Examples 9-12, 14, 17-20, which possess conventional electron transport layer materials (ET9-ET12, ET14, ET17-20) in which fluorene and triazine groups are bonded via p-phenylene, p-,o-biphenylene, p-,p-biphenylene, or naphthyl groups; Comparative Examples 13 and 16, which possess conventional electron transport layer materials (ET13, ET16) in which triazine groups are substituted with [1,1'-biphenyl]-1-yl or phenyl groups; and Comparative Examples 13 and 16, which possess conventional electron transport layer materials (ET15) without 9,9-dimethyl-9H-fluorene groups.

Claims

1. An organic compound selected from the group consisting of compounds 1 to 41: 。 2. The organic compound according to claim 1, wherein, The compound is an electron transport layer or electron transport auxiliary layer material.

3. An organic electroluminescent element, comprising: Anode, cathode, and one or more organic layers between the anode and cathode. At least one of the more than one organic layer comprises the organic compound of claim 1 or 2.

4. The organic compound according to claim 3, wherein, The organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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