Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using same and, more specifically, to an organic compound having excellent electron injection and transport ability and thermal stability, and an organic electroluminescent device comprising same in one or more organic material layers thereof, thereby having improved properties such as luminous efficiency, driving voltage, and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to an organic compound having excellent electron injection and transport capabilities and thermal stability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002] In an organic electroluminescent device (hereinafter referred to as an "organic EL device"), when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials depending on their function.

[0003] The materials forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. Furthermore, a host / dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. Dopant materials can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescent materials, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

[0004] To date, NPB, BCP, Alq3, etc., which are expressed by the following chemical formulas, are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant / host materials for luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are used as blue, green, and red dopant materials as phosphorescent materials that have great advantages in terms of improving efficiency. Currently, CBP has shown excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials offer advantages in terms of luminescence characteristics, their low glass transition temperatures and poor thermal stability make them unsatisfactory in terms of lifespan in organic EL devices. Therefore, the development of high-performance organic layer materials is urgently needed.

[0006] The present invention has as its technical object the provision of a novel compound having excellent heat resistance, carrier transport ability, luminescence ability, etc., which can be used as an organic layer material of an organic electroluminescent device, specifically, as an electron transport layer, an electron transport auxiliary layer, or a luminescent layer.

[0007] In addition, another technical task of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound.

[0008] Other objects and advantages of the present invention can be more clearly explained by the detailed description of the invention and the claims below.

[0009] To achieve the above-mentioned purpose, the present invention provides an organic compound selected from the group consisting of compounds 1 to 41 below:

[0010]

[0011] .

[0012] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0013] For example, the organic layer including the organic compound may be an electron transport layer and / or an electron transport auxiliary layer.

[0014] In one embodiment of the present invention, a compound selected from the group consisting of compounds 1 to 41 can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0015] In particular, when the compound of the present invention is used as an electron transport layer or electron transport auxiliary layer material, it can exhibit high thermal stability, low operating voltage, fast mobility, high current efficiency, and long life characteristics compared to devices using conventional host materials or electron transport materials.

[0016] Accordingly, the organic electroluminescent device including the compound according to the present invention can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0017] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0018] Hereinafter, the present invention will be described in detail.

[0019] <New organic compounds>

[0020] The compound of the present invention is selected from the group consisting of compounds 1 to 41. These compounds have a 9,9-dimethyl-9H-fluorene group substituted with a cyano group, and the fluorene group is bonded to a heteroaromatic ring group (e.g., a triazine group, a pyrimidine group) containing 2 to 3 nitrogen atoms via a linker group. At this time, the compound of the present invention has a structure in which the linker group is an ortho-phenylene group or a meta-phenylene group, or the nitrogen-containing heteroaromatic ring group is substituted with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an ortho-terphenyl group.

[0021] Specifically, the compound of the present invention directly binds a cyano group to a 9,9-dimethyl-9H-fluorene group, thereby controlling the LUMO energy level so that electrons can be efficiently injected from the cathode to the electron transport layer. In this way, the compound of the present invention has improved EWG characteristics and excellent electron injection characteristics, so that, unlike conventional electron transport layer materials that have poor electron injection characteristics and thus lower operating voltage, it can realize low-voltage operating characteristics of the device.

[0022] In addition, the compound of the present invention improves the rigidity of the molecule by including an ortho-phenyl group as a linker group between the 9,9-dimethyl-9H-fluorene group and the nitrogen-containing heteroaromatic ring group, or by substituting the nitrogen-containing heteroaromatic ring group with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an ortho-terphenyl group. Due to these structural features, the compound of the present invention can have physicochemical properties more suitable for electron injection and electron transport by reducing the rearrangement energy (λ) of the molecule and improving the charge transfer rate. In addition, the compound of the present invention can implement long-life characteristics of a device by increasing the molecular stability.

[0023] In addition, the compound of the present invention can induce strong π-π overlap by narrowing the intramolecular conjugation length by limiting the linker group between the 9,9-dimethyl-9H-fluorene group and the nitrogen-containing heteroaromatic ring group to an ortho-phenylene group or a meta-phenylene group, compared to a conventional compound in which the linker group is a para-phenylene group, and thus can realize low-voltage operation of the device. At this time, by substituting the nitrogen-containing heteroaromatic ring group with a naphthyl group, the charge transfer characteristics can be further maximized. In addition, when the linker group is a meta-phenyl group, by substituting the nitrogen-containing heteroaromatic ring group with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an ortho-terphenyl group, the operating voltage and efficiency characteristics of the device can be improved compared to a conventional compound in which the nitrogen-containing heteroaromatic ring group is substituted with a p,p-biphenyl group.

[0024] In addition, by substituting the nitrogen-containing heteroaromatic ring group with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an ortho-terphenyl group, the molecular weight can be increased, thereby improving the thermal stability of the device.

[0025] In addition, since the compound of the present invention has a high triplet energy (T1) by designing the 9,9-dimethyl-9H-fluorene group and the nitrogen-containing heteroaromatic ring group to be ortho- or meta-bonded, unlike para-bonded compounds, it can block excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, not only can the number of excitons contributing to light emission be increased, but light emission can also be confined to a desired region of the device by utilizing the exciton blocking property of the compound. Therefore, the compound of the present invention can improve the light emission efficiency of the device, and can also realize a long life of the device by improving the durability and stability of the device.

[0026] As described above, when the compound of the present invention is applied as an organic layer material of an organic electroluminescent device, specifically, an emitting layer material (a blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, or a life-span improvement layer material, the performance and life-span characteristics of the organic electroluminescent device can be significantly improved. Preferably, when the compound of the present invention is applied as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect in terms of the efficiency, driving voltage, and life-span characteristics of the device can be expected. In particular, when the compound of the present invention is utilized as an electron transport layer or an electron transport auxiliary layer material used as a common layer in an organic electroluminescent device, the performance of the emitting layer, specifically, the blue emitting layer, and the performance of the organic electroluminescent device including the same can be improved. Such an organic electroluminescent device can ultimately maximize the performance of a full-color organic light-emitting panel.

[0027]

[0028] Electron transport layer material

[0029] The present invention provides an electron transport layer comprising a compound selected from the group consisting of compounds 1 to 41.

[0030] The above electron transport layer (ETL) plays a role in moving electrons injected from the cathode to an adjacent layer, specifically, the light-emitting layer.

[0031] The above compound may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

[0032] Electron transport layer materials that can be mixed with the above compounds include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials 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.). These may be used alone or in combination of two or more.

[0033] In the present invention, when the compound and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0034]

[0035] <Electron transport auxiliary layer material>

[0036] In addition, the present invention provides an electron transport auxiliary layer comprising a compound selected from the group consisting of compounds 1 to 41.

[0037] The above electron transport auxiliary layer is positioned 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.

[0038] The above compound may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

[0039] The electron transport auxiliary layer material that can be mixed with the above compound includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a nitrogen-containing heterocyclic derivative, and the like.

[0040] In the present invention, when the compound and the electron transport auxiliary layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0041]

[0042] Organic electroluminescent devices

[0043] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising an organic compound selected from the group consisting of compounds 1 to 41 described above.

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

[0045] The organic layer of one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers includes any one of the compounds 1 to 41. Specifically, the organic layer including the compound is preferably a phosphorescent host material of the light-emitting layer, an electron transport layer, or an electron transport material of the electron transport auxiliary layer.

[0046] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, and may include the compound described above as the host material. In addition, the light-emitting layer of the present invention may include a known compound in the art other than the compound described above as the host.

[0047] When the compound is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound is preferably included in an organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material.

[0048] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have 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 laminated, and optionally, an electron transport auxiliary layer may further be included. At this time, at least one of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport auxiliary layer, the electron transport layer, and the electron injection layer may include any one of the compounds 1 to 41. Preferably, the light-emitting layer (e.g., host), the electron transport layer, or the electron transport auxiliary layer, and more preferably, the electron transport layer or the electron transport auxiliary layer may include any one of the compounds 1 to 41. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.

[0049] The structure of the organic electroluminescent device of the present invention may 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] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers described above contains the compound.

[0051] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0052] The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, etc. can be used.

[0053] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; 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-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0054] Additionally, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0055] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

[0056]

[0057] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0058] [Synthesis Example 1] Synthesis of Compound 1

[0059]

[0060] 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-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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 and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 1, 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%).

[0061] Mass: [(M+H) + ] : 602.74

[0062]

[0063] [Synthesis Example 2] Synthesis of Compound 2

[0064]

[0065] 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-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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 and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 2, 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%).

[0066] Mass: [(M+H) + ] : 602.74

[0067]

[0068] [Synthesis Example 3] Synthesis of Compound 3

[0069]

[0070] 25 g (59.5 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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 and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 3, 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%).

[0071] Mass: [(M+H) + ] : 602.74

[0072]

[0073] [Synthesis Example 4] Synthesis of Compound 4

[0074]

[0075] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine, 26.3 g (76.2 mmol, 1.2 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.6 g (2.5 mmol, 0.04 eq) of Pd(OAc), 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 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 4, 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%).

[0076] Mass: [(M+H) + ] : 576.70

[0077]

[0078] [Synthesis Example 5] Synthesis of Compound 5

[0079]

[0080] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 5, 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%).

[0081] Mass: [(M+H) + ] : 626.76

[0082]

[0083] [Synthesis Example 6] Synthesis of Compound 6

[0084]

[0085] 25g (59.5mmol, 1eq) of 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 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 were added to 375ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 6, 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%).

[0086] Mass: [(M+H) + ] : 602.74

[0087]

[0088] [Synthesis Example 7] Synthesis of Compound 7

[0089]

[0090] 25g (59.5mmol, 1eq) of 2-([1,1'-biphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine, 24.7g (71.4mmol, 1.2eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 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 were added to 375ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 7, 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%).

[0091] Mass: [(M+H) + ] : 602.74

[0092]

[0093] [Synthesis Example 8] Synthesis of Compound 8

[0094]

[0095] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphthalen-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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.6 g (2.5 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 8, 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%).

[0096] Mass: [(M+H) + ] : 576.7

[0097]

[0098] [Synthesis Example 9] Synthesis of Compound 9

[0099]

[0100] 25 g (59.7 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 9, 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%).

[0101] Mass: [(M+H) + ] : 601.75

[0102]

[0103] [Synthesis Example 10] Synthesis of Compound 10

[0104]

[0105] 25 g (59.7 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 10, 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%).

[0106] Mass: [(M+H) + ] : 601.75

[0107]

[0108] [Synthesis Example 11] Synthesis of Compound 11

[0109]

[0110] 25 g (59.7 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 11, 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%).

[0111] Mass: [(M+H) + ] : 601.75

[0112]

[0113] [Synthesis Example 12] Synthesis of Compound 12

[0114]

[0115] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 12, 9,9-dimethyl-7-(2-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)phenyl)-9H-fluorene-2-carbonitrile (23.1 g, yield 63%).

[0116] Mass: [(M+H) + ] : 575.72

[0117]

[0118] [Synthesis Example 13] Synthesis of Compound 13

[0119]

[0120] 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 25.2g(60.0mmol, 1eq), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 24.9g(72.0mmol, 1.2eq), Pd(OAc) 20.5g(2.4mmol, 0.04eq), Xphos 2.3g(4.8mmol, 0.08eq), K2CO3 16.6g(120.0mmol, 2eq) were added to 380ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated under reflux for 6 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 13, 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%).

[0121] Mass: [(M+H) + ] : 603.26

[0122]

[0123] [Synthesis Example 14] Synthesis of Compound 14

[0124]

[0125] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 14, 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%).

[0126] Mass: [(M+H) + ] : 577.23

[0127]

[0128] [Synthesis Example 15] Synthesis of Compound 15

[0129]

[0130] 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 15, 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%).

[0131] Mass: [(M+H) + ] : 577.24

[0132]

[0133] [Synthesis Example 16] Synthesis of Compound 16

[0134]

[0135] 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-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile, 20.7 g (3.0 mmol, 0.04 eq) of Pd(OAc), 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 and stirred under reflux for 8 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 16, 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%).

[0136] Mass: [(M+H) + ] : 577.23

[0137]

[0138] [Synthesis Example 17] Synthesis of Compound 17

[0139]

[0140] 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 31.5g (75.0mmol, 1eq), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile 31.1g (90.0mmol, 1.2eq), Pd(OAc) 20.7g (3.0mmol, 0.04eq), Xphos 2.9g (6.0mmol, 0.08eq), K2CO3 20.7g (150.0mmol, 2eq) were added to 475ml of toluene, 125ml of EtOH, and 125ml of H2O, and heated under reflux for 8 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 17, 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%).

[0141] Mass: [(M+H) + ] : 603.25

[0142]

[0143] [Synthesis Example 18] Synthesis of Compound 18

[0144]

[0145] 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 31.5g (75.0mmol, 1eq), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-4-carbonitrile 31.1g (90.0mmol, 1.2eq), Pd(OAc) 20.7g (3.0mmol, 0.04eq), Xphos 2.9g (6.0mmol, 0.08eq), K2CO3 20.7g (150.0mmol, 2eq) were added to 475ml of toluene, 125ml of EtOH, and 125ml of H2O, and heated under reflux for 8 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 18, 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%).

[0146] Mass: [(M+H) + ] : 603.25

[0147]

[0148] [Synthesis Example 19] Synthesis of Compound 19

[0149]

[0150] 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 31.5g (75.0mmol, 1eq), 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 31.1g (90.0mmol, 1.2eq), Pd(OAc) 20.7g (3.0mmol, 0.04eq), Xphos 2.9g (6.0mmol, 0.08eq), K2CO3 20.7g (150.0mmol, 2eq) were added to 475ml of toluene, 125ml of EtOH, and 125ml of H2O, and heated under reflux for 8 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 19, 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%).

[0151] Mass: [(M+H) + ] : 603.25

[0152]

[0153] [Synthesis Example 20] Synthesis of Compound 20

[0154]

[0155] 25.2g (60.0mmol, 1eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 24.9g (72.0mmol, 1.2eq) of 9,9-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-4-carbonitrile, 20.5g (2.4mmol, 0.04eq) of Pd(OAc), 2.3g (4.8mmol, 0.08eq) of Xphos, and 16.6g (120.0mmol, 2eq) of K2CO3 were added to 380ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated under reflux for 6 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 20, 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%).

[0156] Mass: [(M+H) + ] : 603.24

[0157]

[0158] [Synthesis Example 21] Synthesis of Compound 21

[0159]

[0160] 25.2g (60.0mmol, 1eq) of 2-([1,1'-biphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 24.9g (72.0mmol, 1.2eq) of 9,9-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5g (2.4mmol, 0.04eq) of Pd(OAc), 2.3g (4.8mmol, 0.08eq) of Xphos, and 16.6g (120.0mmol, 2eq) of K2CO3 were added to 380ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated under reflux for 6 hours. It was stirred. After completion of the reaction, it was deactivated with a sufficient amount of water, then transferred to a separatory funnel, MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 21, 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%).

[0161] Mass: [(M+H) + ] : 603.25

[0162]

[0163] [Synthesis Example 22] Synthesis of Compound 22

[0164]

[0165] 25.1 g (60.0 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.4 mmol, 0.04 eq) of Pd(OAc), 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, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 22, 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%).

[0166] Mass: [(M+H) + ] : 602.26

[0167]

[0168] [Synthesis Example 23] Synthesis of Compound 23

[0169]

[0170] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphthalen-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-dioxaborolan-2-yl)-9H-fluorene-3-carbonitrile, 20.6 g (2.5 mmol, 0.04 eq) of Pd(OAc), 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 1.4 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 23 (28 g, yield 75%).

[0171] Mass: [(M+H) + ] : 576.70

[0172]

[0173] [Synthesis Example 24] Synthesis of Compound 24

[0174]

[0175] 25 g (63.5 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(naphthalen-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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.6 g (2.5 mmol, 0.04 eq) of Pd(OAc), 2.4 g (5.1 mmol, 0.08 eq) of Xphos, and 1.4 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 24 (29 g, yield 78%).

[0176] Mass: [(M+H) + ] : 576.70

[0177]

[0178] [Synthesis Example 25] Synthesis of Compound 25

[0179]

[0180] 25 g (54.4 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 25 (26 g, yield 72%).

[0181] Mass: [(M+H) + ] : 652.80

[0182]

[0183] [Synthesis Example 26] Synthesis of Compound 26

[0184]

[0185] 25 g (54.4 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 26 (26 g, yield 74%).

[0186] Mass: [(M+H) + ] : 652.80

[0187]

[0188] [Synthesis Example 27] Synthesis of Compound 27

[0189]

[0190] 25 g (54.4 mmol, 1 eq) of 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 27 (26 g, yield 72%).

[0191] Mass: [(M+H) + ] : 652.80

[0192]

[0193] [Synthesis Example 28] Synthesis of Compound 28

[0194]

[0195] 25 g (54.4 mmol, 1 eq) of 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 28 (25 g, yield 70%).

[0196] Mass: [(M+H) + ] : 652.80

[0197]

[0198] [Synthesis Example 29] Synthesis of Compound 29

[0199]

[0200] 25 g (54.4 mmol, 1 eq) of 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-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 29 (25 g, yield 71%).

[0201] Mass: [(M+H) + ] : 652.80

[0202]

[0203] [Synthesis Example 30] Synthesis of Compound 30

[0204]

[0205] 25 g (54.4 mmol, 1 eq) of 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 30 (27 g, yield 75%).

[0206] Mass: [(M+H) + ] : 652.80

[0207]

[0208] [Synthesis Example 31] Synthesis of Compound 31

[0209]

[0210] 25 g (54.4 mmol, 1 eq) of 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 31 (26 g, yield 72%).

[0211] Mass: [(M+H) + ] : 652.80

[0212]

[0213] [Synthesis Example 32] Synthesis of Compound 32

[0214]

[0215] 25 g (54.4 mmol, 1 eq) of 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-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.2 mmol, 0.04 eq) of Pd(OAc), 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 heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 32 (26 g, yield 69%).

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

[0217]

[0218] [Synthesis Example 33] Synthesis of Compound 33

[0219]

[0220] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.1 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 33 (26 g, yield 75%).

[0221] Mass: [(M+H) + ] : 651.81

[0222]

[0223] [Synthesis Example 34] Synthesis of Compound 34

[0224]

[0225] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.1 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 34 (25 g, yield 72%).

[0226] Mass: [(M+H) + ] : 651.81

[0227]

[0228] [Synthesis Example 35] Synthesis of Compound 35

[0229]

[0230] 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-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.1 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 35 (25 g, yield 72%).

[0231] Mass: [(M+H) + ] : 651.81

[0232]

[0233] [Synthesis Example 36] Synthesis of Compound 36

[0234]

[0235] 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-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 20.5 g (2.1 mmol, 0.04 eq) of Pd(OAc), 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, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 36 (26 g, yield 74%).

[0236] Mass: [(M+H) + ] : 651.81

[0237]

[0238] [Synthesis Example 37] Synthesis of Compound 37

[0239]

[0240] 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 30.3 g (72.4 mmol, 1 eq) of 4-([1,1'-biphenyl]-3-yl)-2-(2-chlorophenyl)-6-phenylpyrimidine, 20.7 g (2.9 mmol, 0.04 eq) of Pd(OAc), 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 37 (34 g, yield 78%).

[0241] Mass: [(M+H) + ] : 607.75

[0242]

[0243] [Synthesis Example 38] Synthesis of Compound 38

[0244]

[0245] 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 25g (72.4mmol, 1eq), 2-([1,1':2',1''-terphenyl]-2-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 35.9g (72.4mmol, 1eq), Pd(OAc)20.7g (2.9mmol, 0.04eq), Xphos 2.8g (5.8mmol, 0.08eq), Cs2CO347.2g (144.8mmol, 2eq) was added to Toluene 375ml, EtOH 100ml, H2O 100ml for 6 hours. The mixture was heated and refluxed. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 38 (34 g, yield 72%).

[0246] Mass: [(M+H) + ] : 678.84

[0247]

[0248] [Synthesis Example 39] Synthesis of Compound 39

[0249]

[0250] 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 35.9 g (72.4 mmol, 1 eq) of 2,4-di([1,1'-biphenyl]-2-yl)-6-(3-chlorophenyl)-1,3,5-triazine, 20.7 g (2.9 mmol, 0.04 eq) of Pd(OAc), 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 39 (35 g, yield 71%).

[0251] Mass: [(M+H) + ] : 678.84

[0252]

[0253] [Synthesis Example 40] Synthesis of Compound 40

[0254]

[0255] 25 g (72.4 mmol, 1 eq) of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile, 34.0 g (72.4 mmol, 1 eq) of 2-(2-chlorophenyl)-4-(2-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine, 20.7 g (2.9 mmol, 0.04 eq) of Pd(OAc), 2.8 g (5.8 mmol, 0.08 eq) of Xphos, and 47.2 g (144.8 mmol, 2 eq) of Cs2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and then MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 40 (34 g, yield 72%).

[0256] Mass: [(M+H) + ] : 652.80

[0257]

[0258] [Synthesis Example 41] Synthesis of Compound 41

[0259]

[0260] 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 25g (72.4mmol, 1eq), 2-([1,1':2',1''-terphenyl]-2-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine 35.9g (72.4mmol, 1eq), Pd(OAc)20.7g (2.9mmol, 0.04eq), Xphos 2.8g (5.8mmol, 0.08eq), Cs2CO347.2g (144.8mmol, 2eq) was added to Toluene 375ml, EtOH 100ml, H2O 100ml for 6 hours. The mixture was heated and refluxed. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel, purified by column chromatography, and stirred in EA / HX to obtain white crystals. The crystals were filtered to obtain the target compound 41 (37 g, yield 75%).

[0261] Mass: [(M+H) + ] : 678.84

[0262]

[0263] [Example 1] Fabrication of a blue organic electroluminescent device

[0264] After the compound 1 synthesized in the above Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, a blue organic electroluminescent device was manufactured according to the following process.

[0265] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0266] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / HB (5 nm) / Compound 1 + Liq (1:1)(30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, HB, and Liq used are as follows, respectively.

[0267]

[0268]

[0269] [Examples 2 to 41] Preparation of blue organic electroluminescent devices

[0270] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the materials described in Table 1 below were used instead of Compound 1 used as an electron transport layer material in Example 1.

[0271]

[0272] [Comparative Examples 1 to 20] Manufacturing of blue organic electroluminescent devices

[0273] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET1 to ETL20 were used instead of Compound 1 used as the electron transport layer material in Example 1. ET1 to ET20 used here are as follows.

[0274]

[0275]

[0276] [Evaluation Example 1]

[0277] For the organic electroluminescent devices manufactured in Examples 1 to 41 and Comparative Examples 1 to 20, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0278] Sample Electron Transport Layer Material Driving Voltage (V) Peak Luminescence (nm) Current Efficiency (cd / A) Example 1 3.24548.6 Example 2 3.74558.6 Example 3 3.54558.8 Example 4 3.54558.8 Example 5 53.74588.5 Example 6 63.34558.5 Example 7 73.24558.6 Example 8 83.74578.8 Example 9 93.84538.4 Example 10 10 3.84538.5 Example 11 11 3.94568.5 Example 12 12 3.74588.4 Example 13 13 3.44568.8 Example 14143.64569 Example 15153.54538.8 Example 16163.54578.6 Example 17173.54568.9 Example 18183.44578.8 Example 19193.54559 Example 20203.54558.8 Example 21213.74568.8 Example 222244558.6 Example 23233.54568.8 Example 24243.54569.2 Example 25253.84578.6 Example 26263.84578.8 Example 27273.74518.8 Example 28283.84518.5 Example 29293.44578.8 Example 30303.54538.6 Example 31313.84588.8 Example 323244558.7 Example 333344538.6 Example 34343.84588.4 Example 35353.94558.4 Example 36363.84538.6 Example 37373.94578.7 Example 38383.74558.5 Example 393944538.7 Example 40403.54589.1 Example 41413.44538.4 Comparative Example 1ET15.54576.5Comparative example 2ET25.24566.7Comparative example 3ET35.54566.8Comparative example 4ET45.14586.7Comparative example 5ET54.84537Comparative example 6ET65.44556.5Comparative example 7ET74.84537.2Comparative example 8ET84.84577.4Comparative example 9ET94.44557.7Comparative example 10ET104.64537.5Comparative example 11ET114.34587.9Comparative example 12ET124.44538Comparative example 13ET134.24558.2Comparative example 14ET144.74558Comparative example 15ET154.84578Comparative example 16ET164.64588.2Comparative example 17ET1754587.8Comparative example 18ET185.24547.8Comparative example 19ET194.84528Comparative example 20ET204.84558.1.

[0279] As shown in Table 1, it was confirmed that the blue organic electroluminescent devices of Examples 1 to 41 using the compound of the present invention in the electron transport layer were superior in terms of driving voltage and current efficiency compared to the organic electroluminescent devices of Comparative Examples 1 to 20 using a conventional electron transport layer material. Specifically, the compound of the present invention has a structure in which a 9,9-dimethyl-9H-fluorene group is substituted with a cyano group. The blue organic electroluminescent devices of Examples 1 to 41 comprising the compound of the present invention as an electron transport layer material were superior in driving voltage and current efficiency compared to the organic electroluminescent devices of Comparative Examples 1 to 8 comprising a conventional electron transport layer material (ET1 to ET8) that did not contain a cyano group or in which a fluorene group was not substituted with a cyano group.

[0280] In addition, the compound of the present invention has a structure in which the fluorene group is bonded to 2 to 3 nitrogen-containing heteroaromatic ring groups through an o-phenylene group, or the fluorene group is bonded to 2 to 3 nitrogen-containing heteroaromatic ring groups substituted with a naphthyl group, a [1,1'-biphenyl]-2-yl substituent, or an o-terphenyl group through an m-phenylene group. The blue organic electroluminescent devices of Examples 1 to 41 comprising the compound of the present invention as an electron transport layer material are organic electroluminescent devices of Comparative Examples 9 to 12, 14, and 17 to 20 comprising conventional electron transport layer materials (ET9 to ET12, ET14, ET17 to 20) in which a fluorene group and a triazine group are bonded to each other through a p-phenylene group, a p,o-biphenylene group, a p,p-biphenylene group, or a naphthalene group; It was confirmed that the organic electroluminescent devices of Comparative Examples 13 and 16 having conventional electron transport layer materials (ET13, ET16) including a triazine group substituted with a [1,1'-biphenyl]-1-yl substituent or a phenyl group, had superior driving voltage, emission peak, and current efficiency compared to the organic electroluminescent devices of Comparative Examples 13 and 16 having conventional electron transport layer materials (ET15) not including a 9,9-dimethyl-9H-fluorene group.

Claims

1. An organic compound selected from the group consisting of compounds 1 to 41 below: .

2. In paragraph 1, The above compound is an organic compound which is a material for an electron transport layer or an electron transport auxiliary layer.

3. An anode; a cathode; and at least one organic layer interposed between the anode and the cathode. An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises an organic compound as described in claim 1 or claim 2.

4. In paragraph 3, An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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