Organic light-emitting compound and organic electroluminescent device using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport ability, light-emitting performance, and thermal stability; and an organic electroluminescent device comprising the novel compound in one or more organic layers thereof and thus having enhanced luminous efficiency, driving voltage and lifespan properties.

Description

Organic light-emitting compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a novel compound having excellent carrier transport capacity, luminescence capacity, and heat resistance, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] Research on organic electroluminescent devices, which began with the observation of organic thin-film luminescence of Bernanose in the 1950s and led to blue electroluminescence using anthracene single crystals in 1965, was presented by Tang in 1987 as a stacked organic electroluminescent device with functional layers divided into a hole layer and an emissive layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, research has evolved by introducing distinct organic layers within the device, leading to the development of specialized materials used for this purpose.

[0004] In organic electroluminescent devices, 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 light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0005] The emissive layer materials of organic electroluminescent devices can be classified into blue, green, and red emitting materials depending on the emission color. In addition, yellow and orange emitting materials are also used to achieve better natural colors. Furthermore, host / dopant systems can be used as emitting materials to increase color purity and luminous efficiency through energy transfer. The above dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex 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, interest is focusing not only on phosphorescent dopants but also on phosphorescent host materials. To date, materials such as NPB, BCP, and Alq3 are widely known for use in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as fluorescent dopant / host 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 due to their significant advantages in terms of efficiency improvement. To date, CBP has demonstrated excellent characteristics as a phosphorescent host material.

[0006] However, while conventional light-emitting materials offer advantages in terms of luminescence characteristics, they do not meet satisfactory standards regarding lifespan in organic electroluminescent devices due to their low glass transition temperatures and very poor thermal stability. Therefore, the development of light-emitting materials with superior performance is required.

[0007]

[0008] The present invention has been devised to solve the aforementioned problems, and more specifically, the technical objective is to provide a novel compound that has excellent heat resistance, carrier transport capacity, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as an electron transport layer material, an electron transport auxiliary layer material, an N-type charge generation layer material, a light-emitting layer material, a lifespan improvement layer material, and / or a light-emitting auxiliary layer material.

[0009] In addition, the present invention has another technical objective of providing an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and improved lifespan.

[0010] Other objects and advantages of the present invention may be more clearly explained by the following detailed description of the invention and claims.

[0011]

[0012] To achieve the above objective, the present invention provides a compound represented by the following chemical formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] X1 to X3 are identical or different from each other, and each is independently CR1 or N, provided that at least two of X1 to X3 are N,

[0017] L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei,

[0018] m and n are each independently integers from 0 to 3, provided that m+n≥ 1, and

[0019] Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei,

[0020] R1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group;

[0021] The arylene group and heteroarylene group of L1 to L2; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of Ar1 to Ar3 and R1 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0022] 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 a compound represented by the chemical formula 1.

[0023] For example, in one embodiment of the present invention, an organic layer comprising a compound represented by Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0024] For example, in one embodiment of the present invention, the organic electroluminescent device comprises: a plurality of light-emitting layer stacks including at least one light-emitting layer; and a charge-generating layer disposed between adjacent stacks among the plurality of light-emitting layer stacks, wherein the charge-generating layer may include a compound represented by the chemical formula 1.

[0025] For example, in one embodiment of the present invention, the charge generating layer comprising the compound may be an N-type charge generating layer.

[0026]

[0027] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0028] In particular, when a compound represented by Formula 1 of the present invention is used as an electron transport layer or electron transport auxiliary layer material, a charge generation layer (e.g., N-type CGL) material, and / or a phosphorescent host, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional host materials or electron transport materials.

[0029] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0030] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0031]

[0032] The present invention will be described in detail below.

[0033] <New Organic Compounds>

[0034] The present invention provides a novel compound having excellent thermal stability, carrier transport capacity, and luminescence capacity.

[0035] According to the present invention, a compound represented by Formula 1 comprises a phenanthroline moiety, a nitrogen-containing heteroaromatic ring, and a phenylene-based moiety of ortho bonds disposed between them, and is characterized by having a basic framework in which they are directly bonded or connected through at least one linker (e.g., L1 to L2).

[0036] Specifically, the phenanthroline moiety included in the compound of Chemical Formula 1 above can form a gap state by binding to a metal (e.g., Li, Yb, etc.) such as an alkali metal or alkaline earth metal, which is a dopant of the N-type charge generation layer. When such a phenanthroline moiety is combined with a nitrogen-containing heteroaromatic ring (e.g., triazine or pyrimidine) having excellent electron transport capabilities, it can be used as an electron transport layer and / or N-type charge generation layer (CGL) material with improved electron transfer characteristics.

[0037] In particular, when phenanthroline capable of forming metal bonds and nitrogen-containing heteroaromatic rings (e.g., triazine or pyrimidine) having strong electron-withdrawing group (EWG) characteristics are connected through phenylene-based moiety of an ortho structure having fast electron transfer and shallow LUMO characteristics, they exhibit a synergy effect in terms of fast electron mobility and interaction with metals, and can be usefully applied as electron transport layer materials or N-type charge generation layer materials with superior performance.

[0038] Accordingly, when the compound of Formula 1, in which a phenanthroline moiety and a nitrogen-containing heteroaromatic ring (e.g., a ring containing X1-X3) are bonded by an ortho-structured phenylene-based moiety, is used as at least one of the electron transport layer material and the N-type charge generation layer material of an organic electroluminescent device, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, and long lifespan characteristics compared to conventional devices can be manufactured.

[0039] Furthermore, since the compound of Chemical Formula 1 has a triplet energy higher than that of the emissive layer, it can prevent excitons generated in the emissive layer from diffusing (moving) to an adjacent electron transport layer or hole transport layer. Accordingly, the number of excitons contributing to light emission increases, thereby improving the luminous efficiency of the device, and the durability and stability of the device are enhanced, which can efficiently increase the lifespan characteristics of the device. In addition, the excellent electron transport capability of the compound represented by Chemical Formula 1 allows for high efficiency and fast mobility in organic electroluminescent devices, and it is easy to control HOMO and LUMO energy levels depending on the direction or position of the substituents.

[0040] As described above, when the compound represented by Formula 1 of the present invention is applied as an organic layer material for an organic electroluminescent device, preferably as an electron transport layer / injection layer material, a charge generation layer (CGL) material, a light-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, a light-emitting auxiliary layer material, or a lifespan improvement layer material, the performance and lifespan characteristics of the organic electroluminescent device can be significantly improved. In particular, when the compound of the present invention is utilized as an electron transport layer, an electron transport auxiliary layer material, and / or an N-type charge generation layer (CGL) material, an organic electroluminescent device can be provided that exhibits a low driving voltage and high luminous efficiency, and has significantly improved lifespan characteristics. Consequently, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0041] According to the present invention, the compound represented by Formula 1 comprises a phenanthroline moiety, a nitrogen-containing heteroaromatic ring (e.g., a ring containing X1-X3), and a phenylene-based moiety of ortho bonds disposed between them, which are directly bonded or bonded through at least one linker (e.g., L1 to L2) to form a basic framework.

[0042] In the compound represented by Chemical Formula 1 above, the phenanthroline moiety (Ar1-containing ring) is a phenanthrene containing two nitrogen groups. Since this phenanthroline moiety is a strong electron withdrawing group (EWG), it exhibits excellent electron transport capacity, and in addition, due to the electron-rich nitrogen and aromatic ring, it has binding characteristics with metals. Accordingly, it can bind to metals such as alkali metals and alkaline earth metals (e.g., Li, Yb, etc.), which are dopants of the charge generation layer (CGL), particularly the N-type charge generation layer, thereby enhancing electron transfer characteristics to the electron transport layer.

[0043] Ar1 can be substituted with various substituents in the phenanthroline moiety. Such Ar1 can be hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar1 is hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40cycloalkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, more specifically hydrogen, deuterium (D), C6~C 60 It is preferable that it be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. Here, specific examples of heteroaryl groups may include carbazole, dibenzofuran, dibenzothiophene, etc., provided that phenanthroline moiety is excluded.

[0044] For example, Ar1 may be embodied as hydrogen or any one selected from the following structural formulas. However, it is not limited thereto.

[0045]

[0046] In the above formula,

[0047] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R1 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0048] As another specific example, the above-mentioned phenanthroline moiety may be further specified as any one of the following structural formulas depending on the bonding position of the introduced Ar1. However, it is not limited thereto.

[0049]

[0050] In the above formula,

[0051] * indicates the part connected to the above chemical formula 1, and

[0052] Ar1 is as defined in Chemical Formula 1.

[0053] In the compound represented by Formula 1 according to the present invention, the other side of the phenanthroline moiety comprises a nitrogen-containing heteroaromatic ring (e.g., azine, a ring containing X1 to X3).

[0054] The above nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X3) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. In one example of a nitrogen-containing heteroaromatic ring, X1 to X3 may be identical or different from each other, and each may independently be CR1 or N, provided that at least two of the plurality of Xs are N. By including a heterocyclic ring containing two to three nitrogen atoms in this way, superior electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

[0055] Here, R1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or may form a condensation ring by combining with any adjacent group. In this case, if there are multiple R1s, the multiple R1s may be identical or different from each other. Specifically, R1 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0056] For example, a nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X3) may be further specified as any one selected from the following structural formulas. However, it is not limited thereto.

[0057]

[0058] In the above formula,

[0059] * indicates the part connected to the above chemical formula 1, and

[0060] Ar2 to Ar3 and R1 are each as defined in Chemical Formula 1.

[0061] The above nitrogen-containing heterocyclic ring (e.g., X-containing ring) may be substituted with Ar2 to Ar3 as various substituents. Ar2 to Ar3 may be identical or different from one another and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar2 to Ar3 are each independently C1 to C 40 alkyl group of, C6~C 60Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, more specifically C6~C 60 It is preferable that the aryl group be selected from the aryl group and the heteroaryl group having 5 to 60 nuclei. Specific examples of the heteroaryl group include carbazole, dibenzofuran, dibenzothiophene, etc., provided that the phenanthroline moiety is excluded.

[0062] For example, Ar2 and Ar3 may be identical or different from each other and may each be independently selected from any one of the following structural formulas. However, this is not limited thereto.

[0063]

[0064]

[0065] In the above formula,

[0066] * indicates the part connected to the above chemical formula 1, and

[0067] R2 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, at least one substituent known in the art (e.g., identical to the R1 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0068] In the compound represented by Formula 1 according to the present invention, the phenanthroline moiety and the nitrogen-containing heteroaromatic ring (e.g., ring containing X1 to X3) are connected through a linker (e.g., L1-L2) attached to an ortho-bonded phenylene moiety (e.g., L1 to L2) positioned between them. When such a linker is present, the HOMO region is expanded to provide an advantage to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO. Additionally, molecular stability can be enhanced.

[0069] The linkers (e.g., L1–L2) are not particularly limited and may be conventional divalent group linkers known in the art. Specifically, L1 and L2 may be identical or different from each other, and each may independently be a single bond or C6–C 24 It may be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei. More specifically, L1 and L2 are each independently C6~C 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei.

[0070] Here, the number of linkers, m and n, are each independently integers from 0 to 3, provided that m+n ≥ 1. Specifically, m and n are each independently integers from 0 to 2, and 0 < m+n < 3. Here, when m is 0, the phenylene moiety of the ortho bond is directly bonded to the phenanthroline moiety without a separate linker (e.g., L1), and when n is 0, the phenylene moiety of the ortho bond is directly bonded to a nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X3) without a linker (e.g., L2).

[0071] Specific examples of the above arylene group linkers include phenylene groups, biphenylene groups, naphthylene groups, anthracenylene groups, indenylene groups, and / or pyrantrenylene groups. More specifically, it is preferable that it be a phenylene group or a biphenylene group. In addition, specific examples of heteroarylene group linkers include pyridine moiety, pyrimidine moiety, pyrazine moiety, triazine moiety, dibenzofuran moiety, dibenzothiophene moiety, dibenzoselenophenone moiety, carbazolilene group, thiophenylene group, indolylene group, furinilene group, quinolinylene group, pyrrolylene group, imidazolilene group, oxazolilene group, and / or thiazolilene group. However, they are not limited thereto.

[0072] For example, L1 and L2 may be identical or different from each other, and each may independently be a single bond or a linker selected from the following structural formulas.

[0073]

[0074] In the above formula,

[0075] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R1 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0076] In the aforementioned Chemical Formula 1, the arylene group and heteroarylene group of L1 to L2; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of Ar1 to Ar3 and R1 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0077] For example, in one embodiment according to the present invention, the compound represented by Chemical Formula 1 may be further specified by Chemical Formula 2 or Chemical Formula 3 depending on the binding position of the ortho linker connected to the phenanthroline moiety.

[0078] [Chemical Formula 2]

[0079]

[0080] [Chemical Formula 3]

[0081]

[0082] In the above formula,

[0083] X1~X3, Ar1~Ar3, L1~L2, m and n are each as defined in Paragraph 1.

[0084] For example, the compound represented by the above chemical formula 2 or 3 may be further embodied in any one of the following chemical formulas 2a to 3b.

[0085] [Chemical Formula 2a]

[0086]

[0087] [Chemical Formula 2b]

[0088]

[0089] [Chemical Formula 2c]

[0090]

[0091] [Chemical Formula 3a]

[0092]

[0093] [Chemical Formula 3b]

[0094]

[0095] In the above formula,

[0096] X1~X3, Ar1~Ar3, L1~L2, m and n are each defined in Chemical Formula 1.

[0097] In another embodiment of the present invention, the compound represented by Chemical Formula 1 can be further specified by Chemical Formula 4 below depending on the type of linker (e.g., L1-L2).

[0098] [Chemical Formula 4]

[0099]

[0100] In the above formula,

[0101] X1~X3, Ar1~Ar3, m and n are each defined in Chemical Formula 1.

[0102] For example, one specific example is the above chemical formula 4. and They may be identical or different from each other, and each may be independently selected from the following structural formulas.

[0103]

[0104]

[0105] In the above formula,

[0106] * indicates the part connected to the above chemical formula 4.

[0107] In another embodiment of the present invention, the compound represented by Formula 4 may be further specified as any one of Formulas 5 to 7 below, depending on the type (e.g., L1-L2) and number (e.g., m~n) of the linker. However, it is not limited thereto.

[0108] [Chemical Formula 5]

[0109]

[0110] [Chemical Formula 6]

[0111]

[0112] [Chemical Formula 7]

[0113]

[0114] In the above formula,

[0115] X1~X3, and Ar1~Ar3 are each as defined in Chemical Formula 1, and

[0116] m and n are integers greater than or equal to 1, respectively.

[0117] For example, the compound represented by the above chemical formulas 5 to 7 may be further embodied in any one of the following chemical formulas 5a to 7e.

[0118] [Chemical Formula 5a]

[0119]

[0120] [Chemical Formula 5b]

[0121]

[0122] [Chemical Formula 5c]

[0123]

[0124] [Chemical Formula 5d]

[0125]

[0126] [Chemical Formula 5e]

[0127]

[0128] [Chemical Formula 6a]

[0129]

[0130] [Chemical Formula 6b]

[0131]

[0132] [Chemical Formula 6c]

[0133]

[0134] [Chemical Formula 6d]

[0135]

[0136] [Chemical Formula 6e]

[0137]

[0138] [Chemical Formula 7a]

[0139]

[0140] [Chemical Formula 7b]

[0141]

[0142] [Chemical Formula 7c]

[0143]

[0144] [Chemical Formula 7d]

[0145]

[0146] [Chemical Formula 7e]

[0147]

[0148] In the above formula,

[0149] X1~X3, and Ar1~Ar3 are each as defined in Chemical Formula 1, and

[0150] m and n are each integers greater than or equal to 1.

[0151] According to another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 8 to 10 below, depending on the type of nitrogen-containing heteroaromatic ring (e.g., a ring containing X1-X3). However, it is not limited thereto.

[0152] [Chemical Formula 8]

[0153]

[0154] [Chemical Formula 9]

[0155]

[0156] [Chemical Formula 10]

[0157]

[0158] In the above formula,

[0159] Ar1~Ar3, L1~L2, m and n are each defined in Chemical Formula 1.

[0160] For example, the compound represented by the above formulas 8 to 10 may be further embodied in any one of the following formulas 8a to 10e.

[0161] [Chemical Formula 8a]

[0162]

[0163] [Chemical Formula 8b]

[0164]

[0165] [Chemical Formula 8c]

[0166]

[0167] [Chemical Formula 8d]

[0168]

[0169] [Chemical Formula 8e]

[0170]

[0171] [Chemical Formula 9a]

[0172]

[0173] [Chemical Formula 9b]

[0174]

[0175] [Chemical Formula 9c]

[0176]

[0177] [Chemical Formula 9d]

[0178]

[0179] [Chemical Formula 9e]

[0180]

[0181] [Chemical Formula 10a]

[0182]

[0183] [Chemical Formula 10b]

[0184]

[0185] [Chemical Formula 10c]

[0186]

[0187] [Chemical Formula 10d]

[0188]

[0189] [Chemical Formula 10e]

[0190]

[0191] In the above formula,

[0192] Ar1~Ar3, L1~L2, m and n are each defined in Chemical Formula 1.

[0193] According to another embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Formulas 11 to 13 below, depending on the binding position of Ar1 introduced into the phenanthroline moiety.

[0194] [Chemical Formula 11]

[0195]

[0196] [Chemical Formula 12]

[0197]

[0198] [Chemical Formula 13]

[0199]

[0200] In the above formula,

[0201] X1~X3, Ar1~Ar3, L1~L2, m and n are each defined in Chemical Formula 1.

[0202] For example, the compound represented by the above chemical formulas 11 to 13 may be further embodied in any one of the following chemical formulas 11a to 13e.

[0203] [Chemical Formula 11a]

[0204]

[0205] [Chemical Formula 11b]

[0206]

[0207] [Chemical Formula 11c]

[0208]

[0209] [Chemical Formula 11d]

[0210]

[0211] [Chemical Formula 11e]

[0212]

[0213] [Chemical Formula 12a]

[0214]

[0215] [Chemical Formula 12b]

[0216]

[0217] [Chemical Formula 12c]

[0218]

[0219] [Chemical Formula 12d]

[0220]

[0221] [Chemical Formula 12e]

[0222]

[0223] [Chemical Formula 13a]

[0224]

[0225] [Chemical Formula 13b]

[0226]

[0227] [Chemical Formula 13c]

[0228]

[0229] [Chemical Formula 13d]

[0230]

[0231] [Chemical Formula 13e]

[0232]

[0233] In the above formula,

[0234] X1~X3, Ar1~Ar3, L1~L2, m and n are each defined in Chemical Formula 1.

[0235] According to another embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Formulas 14 to 18 below, depending on the type of Ar2 to Ar3 introduced into a nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X3).

[0236] [Chemical Formula 14]

[0237]

[0238] [Chemical Formula 15]

[0239]

[0240] [Chemical Formula 16]

[0241]

[0242] [Chemical Formula 17]

[0243]

[0244] [Chemical Formula 18]

[0245]

[0246] In the above formula,

[0247] X1~X3, Ar1, L1~L2, m and n are each as defined in Paragraph 1, and

[0248] Y1 and Y2 are identical or different from each other, and each is independently O, S or CR3R4, and

[0249] R3 and R4 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or may form a condensation ring by combining with any adjacent group. Specifically, R3 and R4 are each independently hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, or to form a condensation ring.

[0250] Ring A is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms. Specific examples of ring A include naphthalene, anthracene, phenanthrene, pyrene, etc. However, it is not limited thereto.

[0251] o and p are identical or different from each other, and each is an integer from 1 to 3 independently.

[0252] The compound represented by Formula 1 of the present invention described above may be further embodied in the compounds exemplified below, such as compounds represented by 1 to 160. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0264] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0265] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0266] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0267] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply attached (penant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0268] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0269] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0270] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0271] In the present invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0272] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0273] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0274] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0275] In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0276]

[0277] Electron Transport Layer Material

[0278] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0279] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0280] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0281] The electron transport layer material that can be mixed with the compound of Formula 1 above includes electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole 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 individually or in combination of two or more types.

[0282] In the present invention, when the compound of Formula 1 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.

[0283]

[0284] Electron Transport Auxiliary Layer Material

[0285] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0286] 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.

[0287] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0288] The electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 above includes electron transport materials that are commonly known in the art. For example, electron transport materials that can be used as the electron transport auxiliary layer may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0289] In the present invention, when the compound of Formula 1 and the electron transport assisting layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0290]

[0291] <Electron Injection Layer Material>

[0292] The present invention provides an electron injection layer comprising a compound represented by the above chemical formula 1.

[0293] The compound represented by the above chemical formula 1 can be used alone as an electron injection layer (EIL) material, or can be used in combination with electron injection layer materials known in the art.

[0294] The electron injection layer material that can be mixed with the compound of Chemical Formula 1 above is not particularly limited as long as it is a material that facilitates electron injection and has high electron mobility, and any electron injection layer material commonly used in the industry can be used without limitation. In this case, the materials forming the electron transport layer and the electron injection layer may be the same or different from each other.

[0295] Non-limiting examples of usable electron injection materials include anthracene derivatives, heteroaromatic compounds, and alkali metal complexes. Specifically, there are lanthanide metals such as LiF, Li2O, BaO, NaCl, CsF; Yb, etc.; or metal halides such as RbCl, RbI, etc., which can be used alone or in a mixture of two or more.

[0296] In the present invention, when the compound of Formula 1 and the electron injection layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0297] The electron injection layer and the electron transport layer according to the present invention may each be used to be co-deposited with an n-type dopant to facilitate the injection of electrons from the cathode. In this case, the n-type dopant may be any alkali metal complex known in the art without limitation, and examples include alkali metals, alkaline earth metals, or rare earth metals.

[0298]

[0299] Charge generation layer

[0300] In addition, the present invention provides a charge generating layer comprising a compound represented by the above chemical formula 1, more specifically an N-type charge generating layer.

[0301] A charge generation layer (CGL) refers to a layer that separates adjacent light-emitting stacks without directly contacting both electrodes (e.g., anode, cathode) in an organic light-emitting device having multiple light-emitting stacks. This charge generation layer is placed between two adjacent light-emitting stacks and acts as a cathode for one light-emitting stack by generating electrons, and acts as an anode for the other light-emitting stack by generating holes.

[0302] The compound represented by the above chemical formula 1 can be used alone as a charge generation layer material, more specifically as an N-type charge generation layer material, or can be used in combination with charge generation layer materials known in the art. Preferably, it is used alone.

[0303] The charge generation layer material mixed with the compound according to the present invention may be any material that can be used as a charge generation layer (CGL) material without limitation. In addition, the material for the charge generation layer may be formed by doping it with a conventional n-type material and / or p-type material known in the art.

[0304] When the compound of Chemical Formula 1 above is mixed with a conventional charge-generating layer material, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0305]

[0306] Organic Electroluminescent Device

[0307] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0308] Specifically, the present invention relates to 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 a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0309] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by the above chemical formula 1. Specifically, the organic layer comprising the compound of the above chemical formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a charge generation layer and / or a lifespan improvement layer, and more specifically, it is preferable to use at least one material among an electron transport layer, an electron transport auxiliary layer, an electron injection layer, and an n-type charge generation layer.

[0310] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0311] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0312] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may 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. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, at least one of the electron transport layer, the electron transport auxiliary layer, and / or the electron injection layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0313] 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.

[0314] 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 one or more of the aforementioned organic layers include a compound represented by Chemical Formula 1.

[0315] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0316] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0317] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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, but are not limited thereto.

[0318] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0319] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0320] In another embodiment of the present invention, the organic electroluminescent device may comprise a plurality of light-emitting stacks, each comprising at least one light-emitting layer.

[0321] A plurality of light-emitting layers included in such a light-emitting stack may each be light-emitting layers that emit light of different colors or light-emitting layers that emit light of the same color. That is, the color of light emitted may vary depending on the material constituting the light-emitting layer. For example, a plurality of light-emitting stacks may include materials that emit blue, green, red, yellow, white, etc., and may be formed using phosphorescent or fluorescent materials. In this case, the colors exhibited by each light-emitting layer may be complementary colors to one another. Additionally, colors may be selected as a combination of colors capable of emitting white light. Each of these light-emitting layers may each include phosphorescent dopants or fluorescent dopants corresponding to the selected color.

[0322] More specifically, the organic electroluminescent device further comprises a plurality of light-emitting layer stacks including at least one light-emitting layer; and a charge generation layer (CGL) disposed between adjacent stacks among the plurality of light-emitting layer stacks, wherein the charge generation layer may be an N-type charge generation layer comprising the compound.

[0323] Such a charge generation layer may further include a material that can be used as a charge generation layer (CGL) material known in the art. Additionally, the material for the charge generation layer may be formed by doping it with a conventional n-type material and / or p-type material known in the art.

[0324]

[0325] The present invention will be explained in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0326]

[0327] [Preparation Examples 1~30]

[0328] [Preparation Example 1] Synthesis of 2-chloro-9-phenyl-1,10-phenanthroline (P-1)

[0329]

[0330] Bromobenzene (21.9 g, 139.7 mmol) was dissolved in 450 ml of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (55.9 mL of 2.5 M in hexane, 139.7 mmol) was slowly added dropwise. After stirring for 1 hour at -78°C, 2-chloro-1,10-phenanthroline (30.0 g, 139.7 mmol) was added and reacted for 3 hours, after which the reaction was terminated with an NH4Cl solution at room temperature. The reaction-terminating mixture was extracted with methylene chloride and washed with brine. The washed organic layer was concentrated, dissolved in 450 ml of methylene chloride, and MnO2 (121.5 g, 1397.3 mmol) was added, followed by heating and reflux stirring for 12 hours. After the reaction was completed, MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and crystallized with acetone and MeOH to obtain 2-chloro-9-phenyl-1,10-phenanthroline (36.2g, 124.4mmol, yield 89%).

[0331] Mass : [(M+H)+] : 292

[0332]

[0333] [Preparation Example 2] Synthesis of 2-([1,1'-biphenyl]-2-yl)-9-chloro-1,10-phenanthroline (P-2)

[0334]

[0335] 2-bromo-1,1'-biphenyl (32.6 g, 139.7 mmol) was dissolved in 450 ml of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (55.9 mL of 2.5 M in hexane, 139.7 mmol) was slowly added dropwise. After stirring for 1 hour at -78°C, 2-chloro-1,10-phenanthroline (30.0 g, 139.7 mmol) was added and reacted for 3 hours, after which the reaction was terminated with NH4Cl solution at room temperature. The reaction-terminating mixture was extracted with Methylene Chloride and washed with Brine. The washed organic layer was concentrated, dissolved in 450 ml of Methylene Chloride, and MnO2 (121.5 g, 1397.3 mmol) was added, followed by heating and reflux stirring for 12 hours. After the reaction was completed, MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and crystallized with acetone and MeOH to obtain 2-([1,1'-biphenyl]-2-yl)-9-chloro-1,10-phenanthroline (43.6g, 118.8mmol, yield 85%).

[0336] Mass : [(M+H)+] : 368

[0337]

[0338] [Preparation Example 3] Synthesis of 2-chloro-9-(naphthalen-2-yl)-1,10-phenanthroline (P-3)

[0339]

[0340] 2-bromonaphthalene (28.9 g, 139.7 mmol) was dissolved in 450 ml of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (55.9 mL of 2.5 M in hexane, 139.7 mmol) was slowly added dropwise. After stirring for 1 hour at -78°C, 2-chloro-1,10-phenanthroline (30.0 g, 139.7 mmol) was added, and the reaction was allowed to proceed for 3 hours before being terminated with an NH4Cl solution at room temperature. The reaction-terminating mixture was extracted with Methylene Chloride and washed with Brine. The washed organic layer was concentrated, dissolved in 450 ml of Methylene Chloride, and MnO2 (121.5 g, 1397.3 mmol) was added, followed by heating and reflux stirring for 12 hours. After the reaction was completed, MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and crystallized with acetone and MeOH to obtain 2-chloro-9-(naphthalen-2-yl)-1,10-phenanthroline (40.0 g, 117.4 mmol, yield 84%).

[0341] Mass : [(M+H)+] : 342

[0342]

[0343] [Preparation Example 4] Synthesis of 2-(2-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-1)

[0344]

[0345] P-1 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1, (2-chlorophenyl)boronic acid (8.1 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(2-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-1) (15.1 g, 41.3 mmol, yield 80%).

[0346] Mass : [(M+H)+] : 368

[0347]

[0348] [Preparation Example 5] Synthesis of 2-(3-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-2)

[0349]

[0350] P-1 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1, (3-chlorophenyl)boronic acid (8.1 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-2) (15.3 g, 41.8 mmol, yield 81%).

[0351] Mass : [(M+H)+] : 368

[0352]

[0353] [Preparation Example 6] Synthesis of 2-(4-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-3)

[0354]

[0355] P-1 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1, (4-chlorophenyl)boronic acid (8.1 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-9-phenyl-1,10-phenanthroline (C-3) (14.4 g, 39.2 mmol, yield 76%).

[0356] Mass : [(M+H)+] : 368

[0357]

[0358] [Preparation Example 7] Synthesis of 2-([1,1'-biphenyl]-2-yl)-9-(4-chlorophenyl)-1,10-phenanth (C-4)

[0359]

[0360] P-2 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 2, (4-chlorophenyl)boronic acid (6.4 g, 40.9 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (17.0 g, 122.7 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-2-yl)-9-(4-chlorophenyl)-1,10-phenanth (C-4) (13.9 g, 31.5 mmol, yield 77%).

[0361] Mass : [(M+H)+] : 444

[0362]

[0363] [Preparation Example 8] Synthesis of 2-(4-chlorophenyl)-9-(naphthalen-2-yl)-1,10-phenanthr (C-5)

[0364]

[0365] P-3 (15.0 g, 44.0 mmol), (4-chlorophenyl)boronic acid (6.9 g, 44.0 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.2 g, 132.0 mmol) synthesized by the method of Preparation Example 3 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-9-(naphthalen-2-yl)-1,10-phenanthr (C-5) (14.1 g, 33.9 mmol, yield 77%).

[0366] Mass : [(M+H)+] : 418

[0367]

[0368] [Preparation Example 9] Synthesis of 7-chloro-2-phenyl-1,10-phenanthroline (C-6)

[0369]

[0370] Step 1. Synthesis of 2,2-dimethyl-5-(((2-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione

[0371] Meldrum's acid (7.4 g, 51.2 mmol) was added to trimethoxymethane (81.6 g, 768.5 mmol), heated and refluxed for 2 hours, then cooled. Subsequently, 2-phenylquinolin-8-amine (10.0 g, 46.6 mmol) was added, and the solution was heated and refluxed for 1.5 hours. Once the reaction was complete, the mixture was cooled to room temperature and then terminated with an NH4Cl solution. The reaction-terminating mixture was extracted with EtOAc and washed with Brine. The washed organic layer was dehydrated with Magnesium Sulfate, concentrated, and recrystallized with EtOH to obtain 2,2-dimethyl-5-(((2-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione (12.2 g, 32.6 mmol, yield 70%).

[0372] Mass : [(M+H)+] : 375

[0373] Step 2. Synthesis of 9-phenyl-1,10-phenanthrolin-4-ol

[0374] 2,2-dimethyl-5-(((2-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione (12.2g, 32.6mmol) synthesized in Step 1 of Preparation Example 9 was added to 122ml of diphenylether and heated and stirred under reflux for 1 hour. After the reaction was completed, it was cooled, petroleum ether was added to crystallize it, and the resulting crystals were filtered to obtain 9-phenyl-1,10-phenanthrolin-4-ol (6.3g, 23.1mmol, yield 71%).

[0375] Mass : [(M+H)+] : 273

[0376] Step 3. Synthesis of 7-chloro-2-phenyl-1,10-phenanthroline

[0377] 9-phenyl-1,10-phenanthrolin-4-ol (6.3g, 23.1mmol) synthesized in Step 2 of Preparation Example 19 was added to POCl3 (71.0g, 463.0mmol) and heated and stirred under reflux for 1 hour. After cooling the solution, it was slowly added to 200ml of water, adjusted to pH 13 with a 20% aqueous NaOH solution, extracted with Methylene Chloride, and after removing water with Magnesium Sulfate, concentrated to obtain 7-chloro-2-phenyl-1,10-phenanthroline (6.4g, 22.0mmol, yield 95%).

[0378] Mass : [(M+H)+] : 292

[0379]

[0380] [Preparation Example 10] Synthesis of 4-chloro-7-phenyl-1,10-phenanthroline (C-7)

[0381]

[0382] Step 1. Synthesis of 2,2-dimethyl-5-(((4-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione

[0383] Meldrum's acid (7.4 g, 51.2 mmol) was added to trimethoxymethane (81.6 g, 768.5 mmol), heated and refluxed for 2 hours, then cooled. Subsequently, 4-phenylquinolin-8-amine (10.0 g, 46.6 mmol) was added, and the solution was heated and refluxed for 1.5 hours. Once the reaction was complete, the mixture was cooled to room temperature and then terminated with an NH4Cl solution. The reaction-terminating mixture was extracted with EtOAc and washed with Brine. The washed organic layer was dehydrated with Magnesium Sulfate, concentrated, and recrystallized with EtOH to obtain 2,2-dimethyl-5-(((4-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione (12.7 g, 34.0 mmol, yield 73%).

[0384] Mass : [(M+H)+] : 375

[0385] Step 2. Synthesis of 7-phenyl-1,10-phenanthrolin-4-ol

[0386] 2,2-dimethyl-5-(((4-phenylquinolin-8-yl)amino)methylene)-1,3-dioxane-4,6-dione (12.7 g, 34.0 mmol) synthesized in Step 1 of Preparation Example 22 was added to 128 ml of diphenylether and heated and stirred under reflux for 1 hour. After the reaction was completed, it was cooled, petroleum ether was added to crystallize it, and the resulting crystals were filtered to obtain 7-phenyl-1,10-phenanthrolin-4-ol (6.7 g, 24.5 mmol, yield 72%).

[0387] Mass : [(M+H)+] : 273

[0388] Step 3. Synthesis of 4-chloro-7-phenyl-1,10-phenanthroline

[0389] 7-phenyl-1,10-phenanthrolin-4-ol (6.7g, 24.5mmol) synthesized in Step 2 of Preparation Example 22 was added to POCl3 (75.1g, 489.6mmol), and the mixture was heated and stirred under reflux for 1 hour. After cooling the solution, it was slowly added to 200ml of water, adjusted to pH 13 with a 20% aqueous NaOH solution, extracted with Methylene Chloride, and after removing water with Magnesium Sulfate, concentrated to obtain 4-chloro-7-phenyl-1,10-phenanthroline (6.5g, 22.5mmol, yield 92%).

[0390] Mass : [(M+H)+] : 292

[0391]

[0392] [Preparation Example 11] Synthesis of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-1)

[0393]

[0394] 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0 g, 56.0 mmol), (2-chlorophenyl)boronic acid (8.8 g, 56.0 mmol), Pd(PPh3)4 (1.9 g, 1.7 mmol), and K2CO3 (23.2 g, 168.1 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-1) (14.4 g, 42.0 mmol, yield 75%).

[0395] Mass : [(M+H)+] : 345

[0396]

[0397] [Preparation Example 12] Synthesis of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-2)

[0398]

[0399] 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0 g, 56.0 mmol), (3-chlorophenyl)boronic acid (8.8 g, 56.0 mmol), Pd(PPh3)4 (1.9 g, 1.7 mmol), and K2CO3 (23.2 g, 168.1 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and refluxed for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-2) (15.2 g, 44.3 mmol, yield 79%).

[0400] Mass : [(M+H)+] : 345

[0401]

[0402] [Preparation Example 13] Synthesis of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-3)

[0403]

[0404] 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0 g, 56.0 mmol), (4-chlorophenyl)boronic acid (8.8 g, 56.0 mmol), Pd(PPh3)4 (1.9 g, 1.7 mmol), and K2CO3 (23.2 g, 168.1 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (T-3) (15.2 g, 44.3 mmol, yield 79%).

[0405] Mass : [(M+H)+] : 345

[0406]

[0407] [Preparation Example 14] Synthesis of 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (T-4)

[0408]

[0409] 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0g, 56.0mmol), (4'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (13.0g, 56.0mmol), Pd(PPh3)4 (1.9g, 1.7mmol), and K2CO3 (23.2g, 168.1mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (T-4) (19.3 g, 45.9 mmol, yield 82%).

[0410] Mass : [(M+H)+] : 421

[0411]

[0412] [Preparation Example 15] Synthesis of 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (T-5)

[0413]

[0414] 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0g, 56.0mmol), (4'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (13.0g, 56.0mmol), Pd(PPh3)4 (1.9g, 1.7mmol), and K2CO3 (23.2g, 168.1mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (T-5) (19.1 g, 45.4 mmol, yield 81%).

[0415] Mass : [(M+H)+] : 421

[0416]

[0417] [Preparation Example 16] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (T-6)

[0418]

[0419] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.0g, 43.6mmol), (2-chlorophenyl)boronic acid (6.8g, 43.6mmol), Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 130.9mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water and heated and stirred under reflux for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (T-6) (14.7 g, 34.9 mmol, yield 80%).

[0420] Mass : [(M+H)+] : 421

[0421]

[0422] [Preparation Example 17] Synthesis of 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (T-7)

[0423]

[0424] 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (15.0g, 47.2mmol), (2-chlorophenyl)boronic acid (7.4g, 47.2mmol), Pd(PPh3)4 (1.6g, 1.4mmol), and K2CO3 (19.6g, 141.6mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water and heated and stirred under reflux for 2 hours. After the reaction was finished, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(2-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (T-7) (16.7 g, 42.5 mmol, yield 90%).

[0425] Mass : [(M+H)+] : 395

[0426]

[0427] [Preparation Example 18] Synthesis of 4-(2-chlorophenyl)-2,6-diphenylpyrimidine (PM-1)

[0428]

[0429] 4-chloro-2,6-diphenylpyrimidine (15.0g, 56.2mmol), (2-chlorophenyl)boronic acid (8.8g, 56.2mmol), Pd(PPh3)4 (1.9g, 1.7mmol), and K2CO3 (23.3g, 168.7mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4-(2-chlorophenyl)-2,6-diphenylpyrimidine (PM-1) (17.0g, 49.5mmol, yield 88%).

[0430] Mass : [(M+H)+] : 344

[0431]

[0432] [Preparation Example 19] Synthesis of 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (PM-2)

[0433]

[0434] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (15.0g, 43.8mmol), (2-chlorophenyl)boronic acid (6.8g, 43.8mmol), Pd(PPh3)4 (1.5g, 1.3mmol), and K2CO3 (18.1g, 131.3mmol) were added to 180ml of toluene, 30ml of ETOH, and 30ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine (PM-2) (16.1 g, 38.5 mmol, yield 88%).

[0435] Mass : [(M+H)+] : 420

[0436]

[0437] [Preparation Example 20] Synthesis of 4-(2-chlorophenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine (PM-3)

[0438]

[0439] 4-chloro-6-(naphthalen-2-yl)-2-phenylpyrimidine (15.0 g, 47.3 mmol), (2-chlorophenyl)boronic acid (7.4 g, 47.3 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), and K2CO3 (19.6 g, 142.0 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4-(2-chlorophenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine (PM-3) (15.8 g, 40.2 mmol, yield 85%).

[0440] Mass : [(M+H)+] : 394

[0441]

[0442] [Preparation Example 21] Synthesis of 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-1)

[0443]

[0444] T-1 (15.0g, 43.6mmol), bis(pinacolato)diboron (14.4g, 56.7mmol), Pd2(dba)3 (1.2g, 1.3 mmol), X-Phos (1.2g, 2.6mmol), and KOAc (8.6g, 87.3mmol), synthesized by the method of Preparation Example 9, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-1)(14.1g, 32.3mmol, yield 74%).

[0445] Mass : [(M+H) + ] : 436

[0446]

[0447] [Preparation Example 22] Synthesis of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-2)

[0448]

[0449] T-2 (15.0g, 43.6mmol), bis(pinacolato)diboron (14.4g, 56.7mmol), Pd2(dba)3 (1.2g, 1.3mmol), X-Phos (1.2g, 2.6mmol), and KOAc (8.6g, 87.3mmol), synthesized by the method of Preparation Example 10, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-2)(13.3g, 30.5mmol, yield 70%).

[0450] Mass : [(M+H) + ] : 436

[0451]

[0452] [Preparation Example 23] Synthesis of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-3)

[0453]

[0454] T-3 (15.0g, 43.6mmol), bis(pinacolato)diboron (14.4g, 56.7mmol), Pd2(dba)3 (1.2g, 1.3 mmol), X-Phos (1.2g, 2.6mmol), and KOAc (8.6g, 87.3mmol), synthesized by the method of Preparation Example 11, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-3) (13.7g, 31.4mmol, yield 72%).

[0455] Mass : [(M+H) + ] : 436

[0456]

[0457] [Preparation Example 24] Synthesis of 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (S-4)

[0458]

[0459] T-4 (15.0g, 35.7mmol), bis(pinacolato)diboron (11.8g, 46.4mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.0g, 2.1mmol), and KOAc (7.0g, 71.4mmol), synthesized by the method of Preparation Example 12, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-1,3,5-triazine (S-4) (13.0g, 25.4mmol, yield 71%).

[0460] Mass : [(M+H) + ] : 512

[0461]

[0462] [Preparation Example 25] Synthesis of 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (S-5)

[0463]

[0464] T-5 (15.0g, 35.7mmol), bis(pinacolato)diboron (11.8g, 46.4mmol), Pd2(dba)3 (1.0g, 1.1 mmol), X-Phos (1.0g, 2.1mmol), and KOAc (7.0g, 71.4mmol), synthesized by the method of Preparation Example 13, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (S-5) (13.2g, 25.7mmol, yield 72%).

[0465] Mass : [(M+H) + ] : 512

[0466]

[0467] [Preparation Example 26] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-6)

[0468]

[0469] T-6 (15.0g, 35.7mmol), bis(pinacolato)diboron (11.8g, 46.4mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.0g, 2.1mmol), and KOAc (7.0g, 71.4mmol), synthesized by the method of Preparation Example 14, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-6)(13.2g, 25.7mmol, yield 72%).

[0470] Mass : [(M+H) + ] : 512

[0471]

[0472] [Preparation Example 27] Synthesis of 2-(naphthalen-2-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-7)

[0473]

[0474] T-7 (15.0g, 38.1mmol), bis(pinacolato)diboron (12.6g, 49.5mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.5g, 76.2mmol), synthesized by the method of Preparation Example 15, were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 2-(naphthalen-2-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (S-7) (13.9g, 28.6mmol, yield 75%).

[0475] Mass : [(M+H) + ] : 486

[0476]

[0477] [Preparation Example 28] Synthesis of 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-8)

[0478]

[0479] PM-1 (15.0 g, 43.8 mmol), bis(pinacolato)diboron (14.4 g, 56.9 mmol), Pd2(dba)3 (1.2 g, 1.3 mmol), X-Phos (1.3 g, 2.6 mmol), and KOAc (8.6 g, 87.5 mmol) synthesized by the method of Preparation Example 16 were added to 300 ml of 1,4-Dioxane and heated under reflux stirring for 6 hours. After the reaction was completed, KOAc was removed by filtration, and the organic layer was concentrated and crystallized with acetone and MeOH to obtain 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-8) (14.4 g, 33.3 mmol, yield 76%).

[0480] Mass : [(M+H) + ] : 435

[0481]

[0482] [Preparation Example 29] Synthesis of 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-9)

[0483]

[0484] PM-2 (15.0g, 35.8mmol), bis(pinacolato)diboron (11.8g, 46.5mmol), Pd2(dba)3 (1.0g, 1.1 mmol), X-Phos (1.0g, 2.1mmol), and KOAc (7.0g, 71.6mmol) synthesized by the method of Preparation Example 17 were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was finished, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-9) (14.4g, 28.3mmol, yield 79%).

[0485] Mass : [(M+H) + ] : 511

[0486]

[0487] [Preparation Example 30] Synthesis of 4-(naphthalen-2-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-10)

[0488]

[0489] PM-3 (15.0g, 38.2mmol), bis(pinacolato)diboron (12.6g, 49.6mmol), Pd2(dba)3 (1.0g, 1.1mmol), X-Phos (1.1g, 2.3mmol), and KOAc (7.5g, 76.4mmol) synthesized by the method of Preparation Example 18 were added to 300ml of 1,4-Dioxane and heated and refluxed for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 4-(naphthalen-2-yl)-2-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (S-10) (13.7g, 28.3mmol, yield 74%).

[0490] Mass : [(M+H) + ] : 485

[0491]

[0492] [Synthesized Examples 1~15]

[0493] [Synthesization Example 1] Synthesis of 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-9-phenyl-1,10-phenanthroline (Compound 3)

[0494]

[0495] C-1 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4, S-2 (17.8 g, 40.9 mmol) synthesized by the method of Preparation Example 20, and Cs2CO3 (26.6 g, 81.8 mmol) were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to prepare 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-9-phenyl-1,10-phenanthroline (3) (20.9g, 32.7mmol, yield 80%).

[0496] Mass : [(M+H)+] :641

[0497]

[0498] [Synthesization Example 2] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-9-phenyl-1,10-phenanthroline (Compound 4)

[0499]

[0500] C-1 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4, S-3 (17.8 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 21 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, followed by the addition of Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol), and the mixture was heated and refluxed for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized using Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-9-phenyl-1,10-phenanthroline (4) (21.2g, 33.1mmol, yield 81%).

[0501] Mass : [(M+H)+] :641

[0502]

[0503] [Synthesization Example 3] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline (Compound 5)

[0504]

[0505] C-2 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 5, and S-1 (17.8 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 19 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline ( 5 )(20.4g, 31.9mmol, yield 78%).

[0506] Mass : [(M+H)+] :641

[0507]

[0508] [Synthesization Example 4] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 6)

[0509]

[0510] C-3 (15.0g, 40.9mmol) synthesized by the method of Preparation Example 6, and S-1 (17.8g, 40.9mmol) and Cs2CO3 (26.6g, 81.8mmol) synthesized by the method of Preparation Example 19 were added to 180ml of Toluene, 30ml of EtOH, and 30ml of DIW, followed by the addition of Pd(OAc)2 (0.3g, 1.2mmol) and X-Phos (1.2g, 2.5mmol), and the mixture was heated and refluxed for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (6) (20.1g, 31.5mmol, yield 77%).

[0511] Mass : [(M+H)+] :641

[0512]

[0513] [Synthesization Example 5] Synthesis of 2-(4''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-9-phenyl-1,10-phenanthroline (Compound 15)

[0514]

[0515] C-1 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4, S-4 (20.9 g, 40.9 mmol) synthesized by the method of Preparation Example 22, and Cs2CO3 (26.6 g, 81.8 mmol) were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(4''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-9-phenyl-1,10-phenanthroline ( 15 )(22.5g, 31.5mmol, yield 76%).

[0516] Mass : [(M+H)+] :717

[0517]

[0518] [Synthesization Example 6] Synthesis of 2-(2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 25)

[0519]

[0520] C-3 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 6, S-5 (20.9 g, 40.9 mmol) synthesized by the method of Preparation Example 23, and Cs2CO3 (26.6 g, 81.8 mmol) were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-yl)-9-phenyl-1,10-phenanthroline ( 25 )(22.2g, 31.1mmol, yield 76%).

[0521] Mass : [(M+H)+] :717

[0522]

[0523] [Synthesization Example 7] Synthesis of 2-(2'-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 48)

[0524]

[0525] C-3 (15.0g, 40.9mmol) synthesized by the method of Preparation Example 6, S-6 (20.9g, 40.9mmol) synthesized by the method of Preparation Example 24, and Cs2CO3 (26.6g, 81.8mmol) were added to 180ml of Toluene, 30ml of EtOH, and 30ml of DIW, followed by the addition of Pd(OAc)2 (0.3g, 1.2mmol) and X-Phos (1.2g, 2.5mmol), and the mixture was heated and refluxed for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized using Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline ( 48 )(22.0g, 30.7mmol, yield 75%).

[0526] Mass : [(M+H)+] :717

[0527]

[0528] [Synthesization Example 8] Synthesis of 2-(2'-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 55)

[0529]

[0530] C-3 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 6, and S-7 (19.8 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 25 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, followed by the addition of Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol), and the mixture was heated and refluxed for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized using Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline ( 55 )(22.3g, 32.3mmol, yield 79%).

[0531] Mass : [(M+H)+] :691

[0532]

[0533] [Synthesization Example 9] Synthesis of 2-(2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 76)

[0534]

[0535] C-3 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 6, and S-8 (17.8 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 26 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (76) (21.4g, 33.5mmol, yield 82%).

[0536] Mass : [(M+H)+] :640

[0537]

[0538] [Synthesization Example 10] Synthesis of 2-(2'-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 79)

[0539]

[0540] C-3 (15.0g, 40.9mmol) synthesized by the method of Preparation Example 6, S-9 (20.9g, 40.9mmol) synthesized by the method of Preparation Example 27, and Cs2CO3 (26.6g, 81.8mmol) were added to 180ml of Toluene, 30ml of EtOH, and 30ml of DIW, after which Pd(OAc)2 (0.3g, 1.2mmol) and X-Phos (1.2g, 2.5mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (79) (23.7 g, 33.1 mmol, yield 81%).

[0541] Mass : [(M+H)+] :716

[0542]

[0543] [Synthesization Example 11] Synthesis of 2-(2'-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (Compound 86)

[0544]

[0545] C-3 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 6, and S-10 (19.8 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 28 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, followed by the addition of Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol), and the mixture was heated and refluxed for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized using Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(6-(naphthalen-2-yl)-2-phenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-9-phenyl-1,10-phenanthroline (86) (22.8g, 33.1mmol, yield 81%).

[0546] Mass : [(M+H)+] :690

[0547]

[0548] [Synthesization Example 12] Synthesis of 2-([1,1'-biphenyl]-2-yl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1,10-phenanthroline (Compound 129)

[0549]

[0550] C-4 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 7, and S-1 (14.7 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.2 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-([1,1'-biphenyl]-2-yl)-9-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-1,10-phenanthroline (129) (20.1g, 28.1mmol, yield 83%).

[0551] Mass : [(M+H)+] :717

[0552]

[0553] [Synthesization Example 13] Synthesis of 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (Compound 138)

[0554]

[0555] C-5 (15.0 g, 36.0 mmol) synthesized by the method of Preparation Example 8, and S-1 (15.7 g, 36.0 mmol) and Cs2CO3 (23.4 g, 72.0 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.2 g, 1.1 mmol) and X-Phos (1.0 g, 2.2 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 2-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (138) (20.6 g, 29.9 mmol, yield 83%).

[0556] Mass : [(M+H)+] :691

[0557]

[0558] [Synthesization Example 14] Synthesis of 7-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-2-phenyl-1,10-phenanthroline (Compound 146)

[0559]

[0560] C-6 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 9, and S-5 (26.4 g, 51.6 mmol) and Cs2CO3 (33.6 g, 103.2 mmol) synthesized by the method of Preparation Example 25 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.5 mmol) and X-Phos (1.5 g, 3.1 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 7-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-2-phenyl-1,10-phenanthroline (146) (26.4g, 41.3mmol, yield 80%).

[0561] Mass : [(M+H)+] :641

[0562]

[0563] [Synthesization Example 15] Synthesis of 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-7-phenyl-1,10-phenanthroline (Compound 151)

[0564]

[0565] C-7 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 10, and S-5 (26.4 g, 51.6 mmol) and Cs2CO3 (33.6 g, 103.2 mmol) synthesized by the method of Preparation Example 25 were added to 180 ml of Toluene, 30 ml of EtOH, and 30 ml of DIW, after which Pd(OAc)2 (0.3 g, 1.5 mmol) and X-Phos (1.5 g, 3.1 mmol) were added and heated under reflux stirring for 4 hours. After the reaction was finished, the temperature was lowered to room temperature, the organic layer was concentrated, and then crystallized with Toluene / Acetone / MeOH. After filtering the crystals, the filtered solid was purified by column chromatography to produce 4-(2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-7-phenyl-1,10-phenanthroline (151) (27.1g, 42.3mmol, yield 82%).

[0566] Mass : [(M+H)+] :641

[0567]

[0568] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0569] Compound 3 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0570] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0571] On the ITO transparent electrode prepared as described above, compound 001 and compound 002 were co-deposited in a weight ratio of 98:2 to form a hole injection layer of 100 Å, then compound 001 was deposited on the hole injection layer to form a hole transport layer of 1400 Å thickness, then compound 003 was deposited on the hole transport layer to a thickness of 50 Å to form a hole transport assist layer, and compound 004 and compound 005 were co-deposited in a weight ratio of 98:2 to form a light-emitting layer of 200 Å thickness. An organic light-emitting diode was fabricated by depositing compound 006 on the upper surface of the above-mentioned light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then co-depositing compound 3 and compound 007 (Liq) in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å, depositing LiF on the upper surface of the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the upper surface of the electron injection layer to form a cathode with a thickness of 1000 Å.

[0572] The structures of compounds 001 to 007 used at this time are as follows.

[0573]

[0574]

[0575] [Examples 2 to 15] Fabrication of Blue Organic Electroluminescent Devices

[0576] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 3 used as the electron transport layer material.

[0577]

[0578] [Comparative Examples 1 to 5] Fabrication of Blue Organic Electroluminescent Devices

[0579] Blue organic electroluminescent devices of Comparative Examples 1 to 5 were fabricated by performing the same procedure as in Example 1, except that compounds A to E were used respectively instead of compound 3 used as the electron transport layer material.

[0580]

[0581]

[0582] [Evaluation Example 1]

[0583] For the blue organic electroluminescent devices fabricated in Examples 1 to 15 and Comparative Examples 1 to 5, respectively, the driving voltage, emission peak, current efficiency, and lifetime characteristics at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0584] Sample Electron Transport Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Lifetime (hrs) Example 1 Compound 33.74578.4328 Example 2 Compound 43.74568.4320 Example 3 Compound 53.84568.4317 Example 4 Compound 63.74578.3298 Example 5 Compound 153.94568.3285 Example 6 Compound 253.74588.3312 Example 7 Compound 483.84588.3326 Example 8 Compound 553.84548.2250 Example 9 Compound 763.74578.4380 Example 10 Compound 793.74588.4376 Example 11 Compound 863.84548.4298 Example 12 Compound 1293.84558.3320 Example 13 Compound 1383.84568.5320 Example 14 Compound 1463.74568.7300 Example 15 Compound 1513.74568.6302 Comparative Example 1 Compound A 4.44566.7190 Comparative Example 2 Compound B 4.44586.8180 Comparative Example 3 Compound C 4.64596.7180 Comparative Example 4 Compound D 6.04596.8110 Comparative Example 5 Compound E 4.74606.2180

[0585] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 13, which use the compounds according to the present invention as electron transport layer materials, are superior in terms of driving voltage, emission peak, current efficiency, and lifetime characteristics compared to the organic electroluminescent devices of Comparative Examples 1 to 5, which use control compounds A to E as electron transport layer materials, in which a phenanthroline moiety and a triazine are combined as a meta-linker instead of an ortho-linker, or in which a moiety with EDG characteristics is combined instead of an arginine group which is an EWG group.

[0586]

[0587] [Example 16] Fabrication of an Organic Electroluminescent Device

[0588] Compound 3 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0589] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0590] On the ITO transparent electrode prepared as described above, compound 001 and compound 002 were co-deposited in a weight ratio of 98:2 to form a hole injection layer of 100 Å, then compound 001 was deposited on the hole injection layer to form a hole transport layer of 200 Å thickness, then compound 003 was deposited to a thickness of 50 Å on the hole transport layer to form a hole transport auxiliary layer, and compound 004 and compound 005 were co-deposited in a weight ratio of 98:2 to form an emissive layer of 200 Å thickness. Compound 007 was deposited to a thickness of 150 Å on the emissive layer to form an electron transport region, and compound 3 and 2% Li were co-deposited on the electron transport region to form an N-type charge generation layer of 80 Å thickness. Compound 001 and Compound 002 were co-deposited in a weight ratio of 98:2 on an N-type charge generation layer to form a 100 Å P-type charge generation layer, then Compound 001 was deposited on the P-type charge generation layer to form a 350 Å thick hole transport layer, then Compound 003 was deposited to a thickness of 50 Å on the hole transport layer to form a hole transport auxiliary layer, and then Compound 004 and Compound 005 were co-deposited in a weight ratio of 98:2 to form a 200 Å thick light-emitting layer. An organic light-emitting device was fabricated by depositing compound 006 on the upper surface of the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then depositing compound 007 and compound 008 in a weight ratio of 1:1 to form an electron transport region with a thickness of 300 Å, depositing LiF on the upper surface of the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the upper surface of the electron injection layer to form a cathode with a thickness of 1000 Å.

[0591] The structures of compounds 001 to 007 used at this time are the same as those described in Example 1, and the structure of compound 008 is as follows.

[0592]

[0593]

[0594] [Examples 17 to 30] Fabrication of Organic Electroluminescent Devices

[0595] An organic electroluminescent device was fabricated by performing the same procedure as in Example 16, except that the compounds in Table 2 below were used instead of Compound 3, which was used as the N-type charge generation layer material in Example 16.

[0596]

[0597] [Comparative Examples 6 to 10] Fabrication of Organic Electroluminescent Devices

[0598] An organic electroluminescent device was fabricated in the same manner as in Example 16, except that compounds A to E were used respectively instead of compound 3 used as the N-type charge generation layer material. The compounds A to E used at this time are the same as those described in Comparative Examples 1 to 5.

[0599]

[0600] [Evaluation Example 2]

[0601] For the organic electroluminescent devices fabricated in Examples 16 to 30 and Comparative Examples 6 to 10, respectively, the driving voltage and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0602] Sample N-type Charge Generation Layer Driving Voltage (V) Current Efficiency (cd / A) Example 16 Compound 37.8 16.0 Example 17 Compound 47.8 15.9 Example 18 Compound 57.8 15.9 Example 19 Compound 67.7 15.8 Example 20 Compound 157.9 16.0 Example 21 Compound 258.0 16.0 Example 22 Compound 487.9 15.9 Example 23 Compound 557.9 15.9 Example 24 Compound 767.8 15.9 Example 25 Compound 797.8 16.0 Example 26 Compound 867.8 16.0 Example 27 Compound 1297.816.0 Example 28 Compound 1387.915.9 Example 29 Compound 1467.716.0 Example 30 Compound 1517.815.9 Comparative Example 6 Compound A8.914.1 Comparative Example 7 Compound B8.914.2 Comparative Example 8 Compound C8.814.0 Comparative Example 9 Compound D8.714.0 Comparative Example 10 Compound E8.912.0

[0603] As shown in Table 2 above, it was found that the organic electroluminescent devices of Examples 16 to 30, which used the compound according to the present invention as an N-type charge generation layer material, were superior in terms of driving voltage and current efficiency compared to the organic electroluminescent devices of Comparative Examples 6 to 10, which used control compounds A to E as N-type charge generation layer materials, in which a phenanthroline moiety and a triazine were combined as a meta-linker instead of an ortho-linker, or in which a moiety with EDG characteristics was combined instead of an argin group which is an EWG group.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 to X3 are identical or different from each other, and each is independently CR1 or N, provided that at least two of X1 to X3 are N, L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei, m and n are each independently integers from 0 to 3, provided that m+n≥ 1, and Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, R1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group; The arylene group and heteroarylene group of L1 to L2; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of Ar1 to Ar3 and R1 are each independently deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

2. In Paragraph 1, The above X1 to X3-containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates the part connected to the above chemical formula 1, and Ar2 to Ar3 and R1 are each as defined in Paragraph 1.

3. In Paragraph 1, Ar2 and Ar3 are identical or different from each other, and each independently C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, The aryl groups and heteroaryl groups of the above Ar2~Ar3 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

4. In Paragraph 1, Compounds in which Ar2 and Ar3 are identical or different from each other and are each independently selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R2 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

5. In Paragraph 1, Ar1 consists of hydrogen, deuterium (D), and C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, The aryl group and heteroaryl group of the above Ar1 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound that is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

6. In Paragraph 1, Ar1 is a compound selected from hydrogen or the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1.

7. In Paragraph 1, L1 and L2 are each independently single bonds, or compounds selected from any one of the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1.

8. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] In the above formula, X1~X3, Ar1~Ar3, L1~L2, m and n are each as defined in Paragraph 1.

9. In Paragraph 1, A compound represented by the above chemical formula 2 or 3 is represented by any one of the following chemical formulas 2a to 3b: [Chemical Formula 2a] [Chemical Formula 2b] [Chemical Formula 2c] [Chemical Formula 3a] [Chemical Formula 3b] In the above formula, X1~X3, Ar1~Ar3, L1~L2, m and n are each as defined in Paragraph 1.

10. In Paragraph 1, Compound represented by the above chemical formula 1 is represented by the following chemical formula 4: [Chemical Formula 4] In the above formula, X1~X3, Ar1~Ar3, m and n are each as defined in Paragraph 1.

11. In Paragraph 10, of the above chemical formula 4 and Compounds that are identical or different from each other and are each independently selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 4.

12. In Paragraph 10, A compound represented by the above chemical formula 4, wherein the compound is represented by any one of the following chemical formulas 5 to 7: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In the above formula, X1~X3 and Ar1~Ar3 are each as defined in Paragraph 1, and m and n are integers greater than or equal to 1, respectively.

13. In Paragraph 12, The compound represented by the above chemical formulas 5 to 7 is a compound represented by any one of the following chemical formulas 5a to 7e: [Chemical Formula 5a] [Chemical Formula 5b] [Chemical Formula 5c] [Chemical Formula 5d] [Chemical Formula 5e] [Chemical Formula 6a] [Chemical Formula 6b] [Chemical Formula 6c] [Chemical Formula 6d] [Chemical Formula 6e] [Chemical Formula 7a] [Chemical Formula 7b] [Chemical Formula 7c] [Chemical Formula 7d] [Chemical Formula 7e] In the above formula, X1~X3 and Ar1~Ar3 are each as defined in Paragraph 1, and m and n are each independently integers greater than or equal to 1.

14. In Paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 8 to 10: [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] In the above formula, Ar1~Ar3, L1~L2, m and n are each as defined in Paragraph 1.

15. In Paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 11 to 13: [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] In the above formula, X1~X3, Ar1~Ar3, L1~L2, m and n are each as defined in Paragraph 1.

16. In Paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 14 to 18: [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] In the above formula, X1~X3, Ar1, L1~L2, m and n are each as defined in Paragraph 1, and Y1 and Y2 are identical or different from each other, and each is independently O, S or CR3R4, and R3 and R4 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group; Ring A is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms, and o and p are identical or different from each other, and each is an integer from 1 to 3 independently.

17. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 160.

18. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound used as one or more materials selected from the group consisting of a light-emitting layer, an electron transport layer, an electron transport assisting layer, an electron injection layer, and an N-type charge generation layer.

19. 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 a compound described in any one of claims 1 to 18.

20. In Paragraph 19, An organic electroluminescent device in which the organic layer containing the above compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer.

21. In Paragraph 19, The above-mentioned organic electroluminescent device is, A plurality of light-emitting layer stacks comprising at least one light-emitting layer; and It further includes a charge generation layer disposed between adjacent stacks among the plurality of light-emitting layer stacks; An organic electroluminescent device in which the charge generating layer comprises the compound.

22. In Paragraph 21, An organic electroluminescent device in which the charge generation layer comprising the above compound is an N-type charge generation layer.

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