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

Abstract

The present invention relates to a novel compound with excellent carrier transport ability, luminescence ability, and thermal stability, and to an organic electroluminescent element in which characteristics such as luminescence efficiency, driving voltage, and lifespan are improved by incorporating this compound in one or more organic layers.

Description

[Technical Field]

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent element using the same, and more particularly to a compound with excellent electron transport capability, and an organic electroluminescent element in which characteristics such as luminescence efficiency, driving voltage, and lifetime are improved by incorporating the compound into one or more organic layers. [Background technology]

[0002] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. The injected holes and electrons combine to form excitons, and light is emitted when these excitons return to their ground state. In this process, the material used as the organic layer can be classified according to its function into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] Luminescent materials are classified according to their emission color into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials for achieving better natural colors. Furthermore, host / dopant systems can be used as luminescent materials to improve color purity and enhance luminescence efficiency through energy transfer.

[0004] Dopant materials can be divided into fluorescent dopants, which use organic materials, and phosphorescent dopants, which use metal complex compounds containing heavy atoms such as Ir and Pt. In this regard, the development of phosphorescent materials can theoretically improve the luminescence efficiency by up to four times compared to fluorescence, so there is a lot of research being done not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] Currently, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as materials for light-emitting layers. In particular, among light-emitting layer materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of improving efficiency, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0006] However, while conventional organic layer materials have advantages in terms of luminescence properties, their low glass transition temperature and poor thermal stability mean they are not satisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, there is a need to develop organic layer materials with superior performance. [Overview of the project] [Problems that the invention aims to solve]

[0007] The present invention aims to provide a novel organic compound that exhibits excellent heat resistance, carrier transport ability, and luminescence ability, and can be used as an organic layer material for organic electroluminescent elements, specifically as a luminescence layer material, a life-improvement layer material, a luminescence auxiliary layer material, an electron transport layer material, and an electron transport auxiliary layer material.

[0008] Furthermore, the present invention also aims to provide an organic electroluminescent element with a low driving voltage, high luminous efficiency, and improved lifespan by incorporating the aforementioned novel compound. [Means for solving the problem]

[0009] To achieve the above objective, the present invention provides a compound represented by the following chemical formula 1.

[0010] [ka] In the aforementioned chemical formula 1, Ar1 to Ar3 are the same or different from each other, and each is independently hydrogen, deuterium (D), C1 to C 40 alkyl group, C2 to C 40 alkenyl group, C2 to C 40 alkynyl group, C3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C1 to C 40 alkyloxy group, C6 to C 60 aryloxy group, C3 to C 40 alkylsilyl group, C6 to C 60 arylsilyl group, C1 to C 40 alkylboron group, C6 to C 60 arylboron group, C6 to C 60 arylphosphine group, C6 to C 60 arylphosphine oxide group and C6 to C 60 arylamine group, provided that the case where at least two or more of Ar1 to Ar3 are hydrogen is excluded, X1 to X5 are the same or different from each other, and each is independently C(R1) or N, provided that at least two or more of X1 to X5 are N, when there are a plurality of R1, the plurality of R1 are the same or different from each other, and each is independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 to C 40 alkyl group, C2 to C 40 alkenyl group, C2 to C 40 alkynyl group, C3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C1 to C 40 alkyloxy group, C6 to C 60 aryloxy group, C3 to C 40 alkylsilyl group, C6 to C 60 arylsilyl group, C1 to C 40 alkylboron group, C6 to C 60The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, two of the multiple R1s are represented as B1 and B2. A1-A2 and B1-B2 are either identical or different from each other, and independently represent hydrogen, deuterium (D), and C1-C. 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60 The aryloxy group, C3~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, L1 and L2 are either identical or different from each other, independently of each other, and are either single bonds or C6~C 18 Selected from the group consisting of arylene groups and heteroarylene groups with 5 to 18 nuclear atoms, d and e are each independent integers between 0 and 4. The aforementioned L1-L2 arylene groups and heteroarylene groups, and the aforementioned Ar1-Ar3, R 1、A1-A2, B1-B2 alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, aryloxy groups, alkyloxy groups, cycloalkyl groups, heterocycloalkyl groups, arylamine groups, alkylsilyl groups, alkylboron groups, arylboron groups, phosphine groups, phosphine oxide groups, and arylamine groups are each independently composed of deuterium (D), halogen, cyano group, nitro group, C1-C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60 The aryloxy group, C1~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group and C6~C 60 It can be substituted with one or more substituents selected from the group consisting of arylamine groups, and if there are multiple substituents, they may be the same or different from one another. Furthermore, the present invention provides an organic electroluminescent element comprising a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers contains a compound represented by the chemical formula 1.

[0011] Here, the organic layer containing the compound represented by chemical formula 1 may be selected from the group consisting of an emissive layer, an emissive auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by chemical formula 1 may be included as at least one of the phosphorescent host material of the emissive layer, the electron transport layer, and the electron transport auxiliary layer. [Effects of the Invention]

[0012] According to one embodiment of the present invention, the compound represented by chemical formula 1 has excellent electron transport ability, luminescence ability, heat resistance, and other properties, and can therefore be used as an organic layer material for an organic electroluminescent element.

[0013] In particular, when the compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer, electron transport auxiliary layer, or light emission auxiliary layer material, it can exhibit a lower refractive index, higher thermal stability, lower driving voltage, higher mobility, higher current efficiency, and longer lifespan compared to conventional host materials or electron transport materials.

[0014] As a result, the organic electroluminescent element containing the compound of chemical formula 1 can be significantly improved in terms of excellent light emission performance, low driving voltage, long lifespan, and high efficiency, and can therefore be effectively applied to full-color display panels and the like.

[0015] The effects of the present invention are not limited to those exemplified above, and a wider range of effects are included herein. [Modes for carrying out the invention]

[0016] The present invention will be described in detail below.

[0017] <Novel Organic Compounds>

[0018] The compound of chemical formula 1 according to the present invention has two azine-based moieties (e.g., a pyrazine group and a pyrimidine / triazine group) with electron-withdrawing group (EWG) capabilities at both ends of the molecule, with a silane group between them, which are either directly linked or linked via another linker (e.g., L1-L2) to form a basic skeleton.

[0019] The compound of chemical formula 1 having such a structure contains, in its molecular structure, a triazine / pyrimidine group and a pyrazine group as functional groups with two strong electron-withdrawing capabilities (EWG). By forming a dual EWG structure [e.g., triazine / pyrimidine group (EWG1)-silane group-pyrazine group (EWG2)], it is advantageous in electron injection and transport properties, thereby improving the electron transport capability to the light-emitting layer and having a great effect on improving the initial drive voltage of the device.

[0020] Furthermore, by arranging different dual EWG groups, such as a triazine / pyrimidine group and a pyrazine group, on either side of a silane group, an asymmetrical structure is formed with respect to the long axis of the molecule. The compound of the present invention exhibits the effect of lowering the device's driving voltage through the combination of a high triplet (T1) energy level due to structural asymmetry and the low-voltage characteristics of the pyrazine group, while simultaneously increasing the strong electron-withdrawing properties of azine groups such as triazine / pyrimidine, thereby improving the device's high-efficiency characteristics. As a result, when the compound of chemical formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, electrons from the negative electrode can be well accommodated, allowing for smooth electron transfer to the light-emitting layer. Consequently, the device's driving voltage can be lowered, resulting in high efficiency and long lifespan characteristics. In particular, because the compound of the present invention has an asymmetrical structure, there is no Tc (Crystallization Temp) in its thermal properties, which is advantageous in terms of processability.

[0021] Furthermore, because this invention uses aromatic hydrocarbon groups and stable structures in condensed forms, rather than simple aliphatic ring groups, the thermal stability of the material can be enhanced. Moreover, since the material does not have a crystallization temperature (Tc), it is effective in improving not only the processability of the device but also its lifespan.

[0022] Furthermore, the compound of chemical formula 1 has a silyl (Si)-based molecule at the center of the molecule, which breaks electron conjugation and has a high triplet (T1) energy value via steric hindrance. This not only protects against holes but also has the ability to quench when an excess of excitons is generated, thus preventing excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. By increasing the number of excitons contributing to light emission in the light-emitting layer, the luminescence efficiency of the device can be improved, and the durability and stability of the device can be improved, thereby efficiently increasing the lifespan of the device. In addition, the introduction of a silane-based molecule increases the molecular weight and ensures a high glass transition temperature (Tg), which can significantly improve heat resistance.

[0023] Furthermore, the compound represented by chemical formula 1 is not only highly advantageous for electron transport, but also exhibits low drive voltage, high efficiency, and long lifetime characteristics. The excellent electron transport capability of such compounds allows for high efficiency and fast mobility in organic electroluminescent devices, and the HOMO and LUMO energy levels can be easily adjusted depending on the orientation or position of the substituents. Therefore, organic electroluminescent devices using the compound can exhibit high electron transport ability.

[0024] The compound represented by chemical formula 1 according to the present invention has a basic skeletal structure comprising two different nitrogen-containing heteroaromatic rings (e.g., pyrimidine / triazine, pyrazine) and a silane moiety, which are directly linked or linked via another linker (e.g., L1-L2).

[0025] The silane moiety positioned at the center of the compound represented by the chemical formula 1 can be any conventional tetravalent silyl / silane moiety (-SiA1A2-) known in the art, without limitation. Such a silane moiety may be substituted with A1 and A2 as substitutions. Such A1-A2 may be identical or different from each other, and each may independently be hydrogen, deuterium (D), and C1-C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60 The aryloxy group, C3~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group, and C6~C 60 Selected from the group consisting of arylamine groups. Specifically, A1 and A2 are either identical or different from each other, and independently of each other, C6-C 60 The group may be selected from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms, more specifically C6 to C 40 It may also be an aryl group.

[0026] In one specific example, A1 and A2 may be identical or different from each other, and each may be independently embodied in any one selected from the following structural formulas. However, this is not limited to these.

[0027] [ka] JPEG2026530485000003.jpg112116

[0028] In the above formula, * indicates the linkage site with the aforementioned chemical formula 1. R2 is hydrogen, deuterium (D), C1~C 40 alkyl groups, C6~C 60 The group is selected from the group consisting of aryl groups and heteroarylene groups with 5 to 18 nuclear atoms. In addition, although not shown in the structural formula above, at least one substituent known in the field (for example, similar to the definition of R1) may be substituted.

[0029] Two different EWG groups (e.g., nitrogen-containing heterocycles) are substituted on one side and the other side of the silane-based moiety, forming an asymmetric dual EWG structure. These two EWG groups may be, for example, a pyrazine group and a pyrimidine / triazine group (e.g., X1-X5 containing rings).

[0030] The X1-X5 ring, a type of azine group, can be a monocyclic nitrogen-containing heteroaromatic ring containing at least two nitrogen atoms. In one example of a nitrogen-containing heteroaromatic ring (e.g., an X1-X5 ring), X1-X5 are either identical or different from each other, and each is independently either C(R1) or N, provided that at least two of X1-X5 are N, specifically containing 2-3 N atoms. Thus, the inclusion of a heteroring containing 2-3 nitrogen atoms results in superior electron absorption properties, which are advantageous for electron injection and transport.

[0031] These B1-B2 groups are either identical or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C1-C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60aryloxy group, C3~C 40 alkylsilyl group, C6~C 60 arylsilyl group, C1~C 40 alkylboron group, C6~C 60 arylboron group, C1~C 40 phosphine group, C1~C 40 phosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups. Specifically, R1 is hydrogen, deuterium, halogen, cyano group, C1~C 40 alkyl group, C6~C 60 is preferably selected from the group consisting of aryl groups and heteroaryl groups having 5 to 60 nuclear atoms.

[0032] In this case, two of the plurality of R1 located on the nitrogen-containing heteroaromatic ring (e.g., a ring containing X1 to X5) may be represented by B1 and B2. Such B1 to B2 are the same as or different from each other, and each independently represents hydrogen, deuterium (D), C1~C 40 alkyl group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 alkyloxy group, C6~C 60 aryloxy group, C3~C 40 alkylsilyl group, C6~C 60 arylsilyl group, C1~C 40 alkylboron group, C6~C 60 arylboron group, C6~C 60 arylphosphine group, C6~C 60 arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups. Specifically, B1 and B2 are the same as or different from each other, and each independently is a non-hydrogen substituent, for example, C6~C 60The group may be selected from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms, more specifically, C6 to C 40 It may also be an aryl group.

[0033] In one specific example, the nitrogen-containing heteroaromatic ring (for example, the X1-X5 containing ring) may be any one selected from the following structural formulas.

[0034] [ka]

[0035] In the above formula, * indicates the linkage site with the aforementioned chemical formula 1. R1, B1, and B2 are defined as in Chemical Formula 1, respectively. Specifically, R1 is hydrogen, deuterium, halogen, cyano group, C1-C 40 alkyl groups, C6~C 60 Selected from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms, B1 and B2 are each independently non-hydrogen substituents, i.e., C6-C 60 It is preferable to select from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms.

[0036] As a more specific example, B1 and B2 may be identical or different from each other, and each may be independently selected from the following structural formulas. However, this is not limited to these examples.

[0037] [ka] JPEG2026530485000006.jpg112114

[0038] In the above formula, * indicates the linkage site with the aforementioned chemical formula 1. R2 is hydrogen, deuterium (D), C1~C 40 alkyl groups, C6~C 60The group is selected from the group consisting of aryl groups and heteroarylene groups with 5 to 18 nuclear atoms. In addition, although not shown in the structural formula above, at least one substituent known in the field (for example, similar to the definition of R1) may be substituted.

[0039] On the other hand, the pyrazine group bonded to the other side of the silane moiety may be substituted with Ar1 to Ar3 as substituents. Such Ar1 to Ar3 may be identical or different from each other, and each may independently be hydrogen, deuterium (D), and C1 to C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60 The aryloxy group, C3~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group, and C6~C 60 Selected from the group consisting of arylamine groups, except that cases where at least two of Ar1 to Ar3 are hydrogen are excluded. Specifically, Ar1 to Ar3 are either identical or different from each other, and each is independently hydrogen, deuterium (D), and C1 to C 40 alkyl groups, C6~C 60 Selected from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms, more specifically C6 to C6 60 It may be an aryl group or a heteroaryl group with 5 to 60 nuclear atoms.

[0040] In one specific example, Ar1 to Ar3 may be identical or different from each other, and each may be independently embodied in any one of the following structural formulas selected from among them. However, it is not limited to this.

[0041] [ka]

[0042] In the above formula, * indicates the linkage site with the aforementioned chemical formula 1. R3 consists of hydrogen, deuterium (D), and C1-C. 40 alkyl groups, C6~C 60 The group is selected from the group consisting of aryl groups and heteroarylene groups with 5 to 18 nuclear atoms. In addition, although not shown in the structural formula above, at least one substituent known in the field (for example, similar to the definition of R1) may be substituted.

[0043] In the compound represented by chemical formula 1 according to the present invention, the pyrazine group and pyrimidine / triazine group located at both ends of a silane moiety are either directly bonded or linked via another linker (e.g., L1-L2). In this way, the presence of linkers (e.g., L1-L2) expands the HOMO region, providing a gain to the HOMO-LUMO distribution, and the appropriate superposition of HOMO-LUMO can enhance charge transfer efficiency.

[0044] Such linkers (e.g., L1-L2) are not particularly limited and may be single bonds or ordinary divalent linkers known in the art. Specifically, L1-L2 may be identical or different from each other and independently single bonds (e.g., direct bonds) or C6-C6 18The group can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. Specific examples of the arylene group and heteroarylene group include phenylene group, biphenylene group, pyrrolylene group, imidazoylene group, oxazolylene group, thiazoylene group, triazolylene group, pyridinylene group, and pyrimidinylene group. More specifically, L1 to L2 are either identical or different from each other, and each is independently single-bonded or C6 to C6 12 It can be selected from the group consisting of arylene groups and heteroarylene groups with 5 to 12 nuclear atoms.

[0045] In this case, the number of linkers (e.g., d, e) may each be an integer between 0 and 4. Specifically, d + e ≥ 1, and more specifically, d and e may each be an integer between 1 and 3. For example, when d and e are 0, L1 and L2 may each be single bonds. Also, when d and e are greater than 0 and 4 or less, multiple L1 and L2 may be identical or different from each other, and each may independently be the remaining substituents after excluding the single bonds in the linker definition described above.

[0046] In one specific example, L1 and L2 may be identical or different from each other, and each may be a single bond or a linking group selected from the following structural formulas.

[0047] [ka]

[0048] In the above formula, * indicates a linkage site with chemical formula 1. Furthermore, at least one substituent known in the art (for example, similar to the R1 definition) may be substituted, although not shown in the aforementioned structural formula.

[0049] In the aforementioned chemical formula 1, the arylene groups L1 to L2 and the heteroarylene group, and the Ar1 to Ar3, R 1、A1-A2, B1-B3 alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, aryloxy groups, alkyloxy groups, cycloalkyl groups, heterocycloalkyl groups, arylamine groups, alkylsilyl groups, alkylboron groups, arylboron groups, phosphine groups, phosphine oxide groups, and arylamine groups are each independently deuterium (D), halogen, cyano group, nitro group, C1-C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3-40 nuclear atoms, C6-C 60 aryl groups, heteroaryl groups with 5-60 nuclear atoms, C1-C 40 alkyloxy group, C6~C 60 The aryloxy group, C1~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 The arylphosphine oxide group, and C6~C 60 The substituents may be substituted with one or more substituents selected from the group consisting of arylamine groups, and if there are multiple substituents, they may be the same or different from each other.

[0050] According to one embodiment of the present invention, the compound represented by chemical formula 1 may be embodied in the following chemical formula 2, depending on the type of linker (e.g., L1 to L2).

[0051] [ka]

[0052] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, d, and e are defined in the same way as in Chemical Formula 1.

[0053] In one specific example, the chemical formula 2

[0054] [ka] (If d and e are each 1 or greater) the following structural formulas may be selected independently, either identical or different from each other.

[0055] [ka]

[0056] In the above formula, * indicates the linkage site with chemical formula 2.

[0057] According to another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 3 to 5, depending on the bonding position of the linker (e.g., L2) connected to the nitrogen-containing heterocycle (e.g., X1 to X5-containing ring). However, it is not limited thereto.

[0058] [ka]

[0059] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, d, and e are defined in the same way as in Chemical Formula 1.

[0060] According to another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 6a to 6l, depending on the number of linkers (e=1 to 2) located between the silane group and the nitrogen-containing heterocycle (e.g., X1 to X5-containing rings) and their bonding positions. However, it is not limited thereto.

[0061] [ka] JPEG2026530485000014.jpg143131JPEG2026530485000015.jpg152130JPEG2026530485000016.jpg122133JPEG2026530485000017.jpg102131

[0062] In the above formula, Ar1-Ar3, A1-A2, B1-B2, R1, and d are defined in the same way as in Equation 1. According to yet another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 7 to 9, depending on the bonding position of the linker (e.g., L1) linked to the pyrazine (e.g., an Ar1-Ar3 containing ring). However, it is not limited thereto.

[0063] [ka] JPEG2026530485000019.jpg63134

[0064] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, d, and e are defined in the same way as in Chemical Formula 1.

[0065] According to yet another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 10a to 10l, depending on the number of linkers (d=1 to 2) located between the pyrazine group and the silane group and their bonding positions. However, it is not limited thereto.

[0066] [ka] JPEG2026530485000021.jpg148135JPEG2026530485000022.jpg165134JPEG2026530485000023.jpg145135JPEG2026530485000024.jpg124134

[0067] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, and e are defined in the same way as in Chemical Formula 1.

[0068] According to yet another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 11 to 14, depending on the type of linker (e.g., L1 to L2) and nitrogen-containing heterocycle (e.g., X1 to X5-containing ring). However, it is not limited thereto.

[0069] [ka] JPEG2026530485000026.jpg45131

[0070] In the above formula, Ar1-Ar3, A1-A2, B1-B2, d, and e are defined in the same way as in Chemical Formula 1.

[0071] According to yet another embodiment of the present invention, the compound represented by chemical formula 1 may be further embodied in any one of the following chemical formulas 15 to 18, depending on the type of substituted Ar1 to Ar3 introduced to the pyrazine group. However, it is not limited thereto.

[0072] [ka] JPEG2026530485000028.jpg44125

[0073] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, L1-L2, d, and e are defined in the same way as in Equation 1, except that Ar1-Ar3 are hydrogen.

[0074] The compounds represented by the aforementioned chemical formulas 15 to 18 may be further specified by any one of the following chemical formulas 15a to 18a, depending on the type of linker (e.g., L1 to L2).

[0075] [ka] JPEG2026530485000030.jpg48138

[0076] In the above formula, X1-X5, Ar1-Ar3, A1-A2, B1-B2, d, and e are defined in the same way as in Chemical Formula 1, except when Ar1-Ar3 is hydrogen.

[0077] The compound represented by chemical formula 1 according to the present invention, as described above, may be further embodied in any one of the compounds 1 to 128 exemplified below. However, the compound represented by chemical formula 1 of the present invention is not limited to the examples shown below.

[0078] [ka] JPEG2026530485000032.jpg175142JPEG2026530485000033.jpg173144JPEG2026530485000034.jpg17913 8JPEG2026530485000035.jpg172136JPEG2026530485000036.jpg179138JPEG2026530485000037.jpg66141

[0079] In the present invention, "nuclear atom number" means the number of ring atoms constituting a cyclic structure, and the nuclear atom may mean carbon, or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the nuclear atom number of pyridine means 6 atoms, including 5 C and 1 N that constitute the pyridine ring.

[0080] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl.

[0081] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0082] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples include, but are not limited to, ethynyl and 2-propynyl.

[0083] In the present invention, "aryl" means a monovalent substituent derived from a C6-C40 aromatic hydrocarbon, either a single ring or a combination of two or more rings. It may also include forms in which two or more rings are pendant or fused to one another. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0084] In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms, are substituted with heteroatoms such as N, O, S, or Se. Furthermore, forms in which two or more rings are pendanted or fused to each other may also be included, as may forms fused with an aryl group. Examples of such heteroaryls include, but are not limited to, six-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, 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.

[0085] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl compound having 5 to 40 carbon atoms. Examples of such aryloxys include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0086] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' means an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0087] In this invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0088] In the present invention, "cycloalkyl" means 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.

[0089] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon with 3 to 40 nuclear atoms, wherein one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0090] In this 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.

[0091] 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.

[0092] <Electron transport layer material>

[0093] The present invention provides an electron transport layer containing the compound represented by the chemical formula 1.

[0094] The electron transport layer (ETL) plays the role of moving electrons injected from the negative electrode to an adjacent layer, specifically the light-emitting layer.

[0095] The compound represented by chemical formula 1 may be used alone as an electron transport layer (ETL) material, or it may be used in combination with electron transport layer materials known in the art, but it is preferable to use it alone.

[0096] The electron transport layer material that can be mixed with the compound of chemical formula 1 includes ordinary electron transport materials known in the art. Examples of usable electron transport materials include, but are not limited to, oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3(tris(8-quinolinolato)-aluminium), BAlq, SAlq, Almq3), and gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used individually or in combination of two or more.

[0097] In the present invention, when the compound of chemical formula 1 and the electron transport layer material are used in combination, the mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0098] <Electron transport auxiliary layer material>

[0099] Furthermore, the present invention provides an electron transport auxiliary layer containing the compound represented by the chemical formula 1.

[0100] The electron transport 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.

[0101] The compound represented by chemical formula 1 may be used alone as an electron transport auxiliary layer material, or it may be used in combination with electron transport layer materials known in the art, but it is preferable to use it alone.

[0102] The electron transport auxiliary layer material that can be mixed with the compound of chemical formula 1 includes ordinary electron transport materials known in the art. Examples of the electron transport auxiliary layer include oxadiazole derivatives, triazole derivatives, penanthroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives.

[0103] In the present invention, when the compound of chemical formula 1 and the electron transport auxiliary layer material are mixed, the mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0104] <Organic electroluminescent element>

[0105] Another aspect of the present invention relates to an organic electroluminescent element (organic EL element) containing the compound represented by chemical formula 1 according to the present invention as described above.

[0106] Specifically, the present invention relates to an organic electroluminescent element comprising a positive electrode (anode), a negative electrode (cathode), and one or more organic layers interposed between the positive and negative electrodes, wherein at least one of the one or more organic layers contains a compound represented by the chemical formula 1. In this case, the compound may be used alone or as a mixture of two or more.

[0107] The one or more organic layers may be any one or more of the following: a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifetime improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic layers contains the compound represented by chemical formula 1. Specifically, the organic layer containing the compound of chemical formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifetime improvement layer, and more specifically, it is preferable that it is an electron transport layer, an electron transport auxiliary layer, or a light-emitting auxiliary layer.

[0108] The light-emitting layer of the organic electroluminescent element according to the present invention comprises a host material and a dopant material, and the host material may include the compound of chemical formula 1. In addition, the light-emitting layer of the present invention may include, in addition to the compound of chemical formula 1, compounds known in the art as hosts.

[0109] When the compound represented by chemical formula 1 is included as a light-emitting layer material, preferably a blue, green, or red phosphorescent host material, in an organic electroluminescent element, the bonding 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 element. Specifically, the compound represented by chemical formula 1 is preferably included in the organic electroluminescent element as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by chemical formula 1 of the present invention is preferably an exciplex N-type host material for green phosphorescence in a light-emitting layer having high efficiency.

[0110] The structure of the organic electroluminescent element of the present invention is not particularly limited, but it may be a structure in which a substrate, a positive electrode, a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport layer, and a negative electrode are sequentially stacked. In this case, one or more of the hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport layer, and electron injection layer may contain the compound represented by chemical formula 1, preferably the light emission layer, and more preferably the phosphorescent host may contain the compound represented by chemical formula 1. Furthermore, an electron injection layer may be further stacked on top of the electron transport layer.

[0111] The structure of the organic electroluminescent element of the present invention may be one in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

[0112] The organic electroluminescent element of the present invention can be manufactured by forming the organic layers and electrodes using materials and methods known in the industry, except that one or more of the aforementioned organic layers contain the compound represented by chemical formula 1.

[0113] The organic layer may be formed by vacuum deposition or solution coating. Examples of solution coating methods include, but are not limited to, spin coating, deep coating, doctor bladening, inkjet printing, or thermal transfer.

[0114] The substrate used in the manufacture of the organic electroluminescent element of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0115] Furthermore, any cathode material known in the field can be used without restriction. Examples include, but are not limited to, 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 polythiopene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiopene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0116] Furthermore, any negative electrode material known in the field can be used without limitation. Examples include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0117] Furthermore, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and any ordinary material known in the industry can be used without restriction.

[0118] The present invention will be described in detail below with reference to examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited to the following examples.

[0119] <Synthesis Examples 1-11> [Synthesis Example 1] Synthesis of Compound 1

[0120] [ka]

[0121] [Synthesis Example 1-1] Synthesis of Compound 1-iii

[0122] [ka]

[0123] 50 g of (3-bromophenyl)(3-chlorophenyl)diphenylsilane (111.1 mmol, 1 eq), 33.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (133.4 mmol, 1.2 eq), 3.3 g of PdCl2 (dppf) (4.4 mmol, 0.04 eq), and 21.9 g of KOAc (222.3 mmol, 2 eq) were added to 750 ml of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 1-iii, (3-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (45.3 g, yield 82%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H): σ=7.85 (1H, d), 7.61 (1H, s), 7.55 (1H, s), 7.50-7.32(15H, m), 1,20 (12H, s)

[0124] [Synthesis Example 1-2] Synthesis of Compound 1-ii

[0125] [ka]

[0126] 45.3 g (91.1 mmol, 1 eq) of (3-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 26.7 g (100.3 mmol, 1.1 eq) of 5-chloro-2,3-diphenylpyrazine, 3.2 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 25.2 g (182.3 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmol. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 1-ii, 5-(3-((3-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine (38.4 g, yield 70%). Mass:[(M+H)] + ]:602.11 NMR ( 1 H):σ=8.79(1H, s), 8.50(1H, d), 8.44(1H, s), 8.03(2H, d), 7.68~7.59(5H, m), 7.46~7.32(19H, m)

[0127] [Synthesis Example 1-3] Synthesis of Compound 1-i

[0128] [ka]

[0129] 38.4 g (63.8 mmol, 1 eq) of 5-(3-((3-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine, 19.4 g (76.6 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.3 g (3.2 mmol, 0.04 eq) of PdCl2 (dppf), 6.1 g (12.8 mmol, 0.2 eq) of XPhos, and 15.1 g (153.1 mmol, 2 eq) of KOAc were added to 570 mL of 1,4-dioxane and stirred under heating and reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 1-i,5-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine (34.0 g, yield 77%). Mass:[(M+H)] + ]:692.74 NMR ( 1 H):σ=8.79(1H, s), 8.50(1H, d), 8.46(1H, s), 8.03(2H, d), 7.85(1H, d), 7.68-7.59(5H, m), 7.46-7.32(18H, m), 1.20(12H, s)

[0130] [Synthesis Example 1-4] Synthesis of Compound 1

[0131] [ka]

[0132] 34.0 g (49.1 mmol, 1 eq) of 5-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine, 14.5 g (54 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.7 g (1.5 mmol, 0.03 eq) of Pd(PPh3)4, and 13.6 g (98.3 mmol, 2 eq) of K2CO3 were placed in 500 mL of toluene, 150 mL of EtOH, and 150 mL of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 1 (target compound B), a white solid (33.3 g, yield 85%). Mass:[(M+H)] + ]:798.04

[0133] [Synthesis Examples 2-11] Except for changing the substance of intermediate A as shown in Table 1 below, the method for producing compound 1 was carried out in the same manner as described above, and the target compound B for synthesis examples 2 to 11 was synthesized as follows.

[0134] [Table 1] JPEG2026530485000044.jpg162135

[0135] <Synthesis Examples 12-17> [Synthesis Example 12] Synthesis of Compound 21

[0136] [ka]

[0137] [Synthesis Example 12-1] Synthesis of Compound 21-iii

[0138] [ka]

[0139] 50 g of (4-bromophenyl)(3-chlorophenyl)diphenylsilane (111.1 mmol, 1 eq), 33.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (133.4 mmol, 1.2 eq), 3.3 g of PdCl2 (dppf) (4.4 mmol, 0.04 eq), and 21.9 g of KOAc (222.3 mmol, 2 eq) were added to 750 mL of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 21-iii, ((3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.2 g, yield 80%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.55(1H, s), 7.46-7.32(15H, m), 1.20(12H, s)

[0140] [Synthesis Example 12-2] Synthesis of Compound 21-ii

[0141] [ka]

[0142] 44.2 g (88.9 mmol, 1 eq) of (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 26.1 g (97.8 mmol, 1.1 eq) of 5-chloro-2,3-diphenylpyrazine, 3.1 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 24.6 g (177.8 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 21-ii, 5-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine (37.4 g, yield 70%). Mass:[(M+H)] + ]:602.11 NMR ( 1 H): σ=8.79(1H, s), 8.50(1H, d), 8.44(1H, s), 8.03(2H, d), 7.68-7.59(5H, m), 7.46-7.32(19H, m)

[0143] [Synthesis Example 12-3] Synthesis of Compound 21-i

[0144] [ka]

[0145] 37.4 g (62.2 mmol, 1 eq) of 5-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine, 19.0 g (74.7 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.3 g (3.1 mmol, 0.04 eq) of PdCl2 (dppf), 5.9 g (12.4 mmol, 0.2 eq) of Xphos, and 14.7 g (149.4 mmol, 2 eq) of KOAc were added to 560 ml of 1,4-dioxane and stirred under reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated and then adsorbed onto silica gel and purified by column chromatography to obtain compound 21-i, 5-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine (34.1 g, yield 79%). Mass:[(M+H)] + ]:692.74 NMR ( 1H ): σ= 8.79(1H, s), 8.43(2H, d), 8.03(2H, d), 7.85(1H, d), 7.69(2H, d), 7.61-7.59(3H, m), 7.45-7.32(18H, m), 1.20(12H, s)

[0146] [Synthesis Example 12-4] Synthesis of Compound 21

[0147] [ka]

[0148] 34.1 g (49.2 mmol, 1 eq) of 5-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine, 14.5 g (54.1 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.7 g (1.5 mmol, 0.03 eq) of Pd(PPh3)4, and 13.6 g (98.3 mmol, 2 eq) of K2CO3 were placed in 500 ml of toluene, 140 ml of EtOH, and 140 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 21 (target compound B) (33.0 g, yield 84%), a white solid. Mass:[(M+H)] + ]:798.04

[0149] [Synthesis Examples 13-17] Except for changing the substance of intermediate A as shown in Table 2 below in Synthesis Example 12, the procedure was carried out in the same manner as the method for producing compound 21, and the target compound B for Synthesis Examples 13 to 17 was synthesized as follows.

[0150] [Table 2] JPEG2026530485000051.jpg76135

[0151] <Synthesis Examples 18-22> [Synthesis Example 18] Synthesis of Compound 41

[0152] [ka]

[0153] [Synthesis Example 18-1] Synthesis of Compound 41-iii

[0154] [ka]

[0155] 50 g (111.1 mmol, 1 eq) of (4-bromophenyl)(4-chlorophenyl)diphenylsilane, 33.9 g (133.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 3.3 g (4.4 mmol, 0.04 eq) of PdCl2 (dppf), and 21.9 g (222.3 mmol, 2 eq) of KOAc were added to 750 ml of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated and then adsorbed onto silica gel and purified by column chromatography to obtain compound 41-iii, (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.7 g, yield 81%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.52-7.38(16H, m), 1.20(12H, s)

[0156] [Synthesis Example 18-2] Synthesis of Compound 41-ii

[0157] [ka]

[0158] (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane 44.7 g (90.0 mmol, 1 eq), 5-chloro-2,3-diphenylpyrazine 26.4 g (99.0 mmol, 1.1 eq), Pd(PPh3)4 3.1 g (2.7 mmol, 0.03 eq), and K2CO3 24.6 g (180.1 mmol, 2 eq) were added into 650 mL of toluene, 180 mL of EtOH and 180 mL of H2O, followed by stirring under heating and reflux for 8 hours. After completion of the reaction, the reaction was quenched with a sufficient amount of water, transferred to a separatory funnel, then MC was added to separate and extract the organic layer. After the extracted organic layer was concentrated, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of EA and hexane was filtered to obtain compound 41-ii, 5-(4-((4-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine (41.1 g, yield 76%). Mass:[(M+H) + :602.11 NMR( 1 H):σ=8.79(1H, s), 8.43(2H, d), 8.03(2H, d), 7.69(2H, d), 7.59-7.32(22H, m)

[0159] [Synthesis Example 18-3] Synthesis of Compound 41-i

[0160]

Chemical Formula

[0161] 41.1 g (68.4 mmol, 1 eq) of 5-(4-((4-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine, 20.9 g (82.1 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (3.4 mmol, 0.04 eq) of PdCl2 (dppf), 6.5 g (13.7 mmol, 0.2 eq) of Xphos, and 16.2 g (164.2 mmol, 2 eq) of KOAc were added to 620 ml of 1,4-dioxane and stirred under reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 41-i, 5-(4-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine (38.9 g, yield 82%). Mass:[(M+H)] + ]:692.74 NMR ( 1H ): σ= 8.79(1H, s), 8.43(2H, d), 8.03(2H, d), 7.85(1H, d), 7.69(2H, d), 7.61-7.59(3H, m), 7.45-7.32(18H, m), 1.20(12H, s)

[0162] [Synthesis Example 18-4] Synthesis of Compound 41

[0163] [ka]

[0164] 38.9 g (56.1 mmol, 1 eq) of 5-(4-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine, 16.5 g (61.7 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.9 g (1.7 mmol, 0.03 eq) of Pd(PPh3)4, and 15.5 g (112.2 mmol, 2 eq) of K2CO3 were placed in 600 ml of toluene, 150 ml of EtOH, and 150 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 41 (target compound B) (37.2 g, yield 83%), a white solid. Mass:[(M+H)] + ]:874.14

[0165] [Synthesis Examples 19-22] Except for changing the substance of intermediate A as shown in Table 3 below in Synthesis Example 18, the procedure was carried out in the same manner as the method for producing compound 41, and the target compound B for Synthesis Examples 19 to 22 was synthesized as follows.

[0166] [Table 3] JPEG2026530485000058.jpg47141

[0167] <Synthesis Examples 23-28> [Synthesis Example 23] Synthesis of Compound 61

[0168] [ka]

[0169] [Synthesis Example 23-1] Synthesis of Compound 61-iii

[0170]

Chem.

[0171] 50 g (111.1 mmol, 1 eq) of (3-bromophenyl)(4-chlorophenyl)diphenylsilane, 33.9 g (133.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 3.3 g (4.4 mmol, 0.04 eq) of PdCl₂(dppf) and 21.9 g (222.3 mmol, 2 eq) of KOAc were added into 750 mL of 1,4-dioxane, and the mixture was stirred under heating and reflux for 4 hours. After completion of the reaction, the reaction was quenched with a sufficient amount of water, then transferred to a separatory funnel, MC was added thereto, and the organic layer was separated and extracted. After the extracted organic layer was concentrated, it was adsorbed onto silica gel and purified by column chromatography to obtain compound 61-iii, (4-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (45.3 g, yield 82%). Mass:[(M+H) + :496.91 NMR( 1 H):σ=7.85(1H, d), 7.61(1H, s), 7.52-7.32(16H, m), 1.20(12H, s)

[0172] [Synthesis Example 23-2] Synthesis of Compound 61-ii

[0173]

Chem.

[0174] 45.3 g (91.1 mmol, 1 eq) of (4-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 26.7 g (100.3 mmol, 1.1 eq) of 5-chloro-2,3-diphenylpyrazine, 3.2 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 25.2 g (182.3 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 61-ii, 5-(3-((4-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine (43.8 g, yield 80%). Mass:[(M+H)] + ]:602.11 NMR ( 1 H):σ=8.79(1H, s), 8.50(1H, d), 8.46(1H, s), 8.03(2H, d), 7.68-7.32(24H, m)

[0175] [Synthesis Example 23-3] Synthesis of Compound 61-i

[0176] [ka]

[0177] 43.8 g (72.9 mmol, 1 eq) of 5-(3-((4-chlorophenyl)diphenylsilyl)phenyl)-2,3-diphenylpyrazine, 22.2 g (87.5 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.7 g (3.6 mmol, 0.04 eq) of PdCl2 (dppf), 7.0 g (14.6 mmol, 0.2 eq) of Xphos, and 17.2 g (175.0 mmol, 2 eq) of KOAc were added to 640 ml of 1,4-dioxane and stirred under reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 61-i, 5-(3-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine (38.4 g, yield 76%). Mass:[(M+H)] + ]:692.74 NMR ( 1 H):σ=8.79(1H, s), 8.50(1H, d), 8.46(1H, s), 8.03(2H, d), 7.85(1H, d), 7.68-7.59(5H, m), 7.46-7.32(18H, m), 1.20(12H, s)

[0178] [Synthesis Example 23-4] Synthesis of Compound 61

[0179] [ka]

[0180] 38.4 g (55.4 mmol, 1 eq) of 5-(3-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2,3-diphenylpyrazine, 16.3 g (61.0 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.9 g (1.7 mmol, 0.03 eq) of Pd(PPh3)4, and 15.3 g (110.8 mmol, 2 eq) of K2CO3 were placed in 550 ml of toluene, 150 ml of EtOH, and 150 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 61 (target compound B) (36.3 g, yield 82%), a white solid. Mass:[(M+H)] + ]:798.04

[0181] [Synthesis Examples 24-28] Except for changing the substance of intermediate A as shown in Table 4 below in Synthesis Example 23, the procedure was carried out in the same manner as the method for producing compound 61, and the target compound B for Synthesis Examples 24 to 28 was synthesized as follows.

[0182] [Table 4] JPEG2026530485000065.jpg58141

[0183] [Synthesis Example 29] Synthesis of Compound 81

[0184] [ka]

[0185] [Synthesis Example 29-1] Synthesis of Compound 81-iii 50 g (111.1 mmol, 1 eq) of (3-bromophenyl)(3-chlorophenyl)diphenylsilane, 33.9 g (133.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 3.3 g (4.4 mmol, 0.04 eq) of PdCl2 (dppf), and 21.9 g (222.3 mmol, 2 eq) of KOAc were added to 750 ml of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 81-iii, (3-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (45.3 g, yield 82%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H): σ=7.85 (1H, d), 7.61 (1H, s), 7.55 (1H, s), 7.50-7.32(15H, m), 1,20 (12H, s)

[0186] [Synthesis Example 29-2] Synthesis of Compound 81-ii 45.3 g (91.1 mmol, 1 eq) of (3-chlorophenyl)diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 34.4 g (100.3 mmol, 1.1 eq) of 2-chloro-3,5,6-triphenylpyrazine, 3.2 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 25.2 g (182.3 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 9 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 81-ii, 2-(3-((3-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine (46.3 g, yield 75%). Mass:[(M+H)] + ]:677.32 NMR ( 1 H):σ=8.50(1H, d), 8.44(1H, d), 8.03(6H, s), 7.66-7.59(6H, m), 7.46-7.32(19H, m)

[0187] [Synthesis Example 29-3] Synthesis of Compound 81-i 46.3 g (68.4 mmol, 1 eq) of 2-(3-((3-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine, 20.8 g (82.0 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (3.4 mmol, 0.04 eq) of PdCl2 (dppf), 6.5 g (13.7 mmol, 0.2 eq) of Xphos, and 16.1 g (164.1 mmol, 2 eq) of KOAc were added to 700 ml of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 81-i, 2-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine (40.5 g, yield 77%). Mass:[(M+H)] + ]:768.84 MRN( 1 H): σ=8.50(1H,d), 8.44(1H,s), 8.03(6H,d), 7.85(2H,d), 7.68-7.59(5H,m), 7.46-7.32(18H,m), 1.20(12H,s)

[0188] [Synthesis Example 29-4] Synthesis of Compound 81 40.5 g (52.6 mmol, 1 eq) of 2-(3-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine, 15.5 g (57.9 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.8 g (1.6 mmol, 0.03 eq) of Pd(PPh3)4, and 14.5 g (105.3 mmol, 2 eq) of K2CO3 were placed in 600 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 6 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 81 (target compound B) (36.8 g, yield 80%), a white solid. Mass:[(M+H)] + ]:874.14

[0189] [Synthesis Example 30] Synthesis of Compound 82

[0190] [ka]

[0191] [Synthesis Example 30-1] Synthesis of Compound 81-iii 50 g of (4-bromophenyl)(3-chlorophenyl)diphenylsilane (111.1 mmol, 1 eq), 33.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (133.4 mmol, 1.2 eq), 3.3 g of PdCl2 (dppf) (4.4 mmol, 0.04 eq), and 21.9 g of KOAc (222.3 mmol, 2 eq) were added to 750 mL of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 82-iii, (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.2 g, yield 80%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.55(1H, s), 7.46-7.32(15H, m), 1.20(12H, s)

[0192] [Synthesis Example 30-2] Synthesis of Compound 82-ii 44.2 g (88.9 mmol, 1 eq) of (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 33.5 g (97.8 mmol, 1.1 eq) of 2-chloro-3,5,6-triphenylpyrazine, 3.1 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 24.6 g (177.8 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 9 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 82-ii, 2-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine (47.6 g, yield 75%). Mass:[(M+H)] + ]:677.32 NMR ( 1 H):σ=8.43(2H, d), 8.03(6H, d), 7.69(2H, d), 7.59-7.55(4H, m), 7.46-7.32(19H, m)

[0193] [Synthesis Example 30-3] Synthesis of Compound 81-i 47.6 g (70.2 mmol, 1 eq) of 2-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine, 21.4 g (84.3 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.6 g (3.5 mmol, 0.04 eq) of PdCl2 (dppf), 6.7 g (14.0 mmol, 0.2 eq) of Xphos, and 16.6 g (168.6 mmol, 2 eq) of KOAc were added to 700 ml of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 82-i, 2-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine (41.6 g, yield 77%). Mass:[(M+H)] + ]:768.84 NMR ( 1H ): σ= 8.79(1H, s), 8.43(2H, d), 8.03(2H, d), 7.85(1H, d), 7.69(2H, d), 7.61-7.59(3H, m), 7.45-7.32(18H, m), 1.20(12H, s)

[0194] [Synthesis Example 30-4] Synthesis of Compound 82 41.6 g (54.1 mmol, 1 eq) of 2-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine, 25.0 g (59.5 mmol, 1.1 eq) of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (intermediate A), 1.9 g (1.6 mmol, 0.03 eq) of Pd(PPh3)4, and 15.0 g (108.2 mmol, 2 eq) of K2CO3 were placed in 600 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and stirred under reflux for 6 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with plenty of water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring with a small amount of EA and hexane was filtered to obtain compound 81 (target compound B), 42.1 g (yield 82%), as a white solid. Mass:[(M+H)] + ]=950.23

[0195] [Synthesis Example 31] Synthesis of Compound 85

[0196] [ka]

[0197] [Synthesis Example 31-1] Synthesis of Compound 85-iii 50 g (111.1 mmol, 1 eq) of (4-bromophenyl)(4-chlorophenyl)diphenylsilane, 33.9 g (133.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 3.3 g (4.4 mmol, 0.04 eq) of PdCl2 (dppf), and 21.9 g (222.3 mmol, 2 eq) of KOAc were added to 750 ml of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 85-iii, (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 44.7 g (81% yield). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.52-7.38(16H, m), 1.20(12H, s)

[0198] [Synthesis Example 31-2] Synthesis of Compound 85-ii 44.7 g (90.0 mmol, 1 eq) of (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 34.0 g (99.0 mmol, 1.1 eq) of 2-chloro-3,5,6-triphenylpyrazine, 3.1 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 24.6 g (180.1 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 85-ii, 2-(3-((4-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine 45.7 g (75% yield). Mass:[(M+H)] + ]:602.11 NMR ( 1 H):σ=8.50(1H,d), 8.44(1H,s), 8.03(6H,d), 7.66-7.32(25H,m)

[0199] [Synthesis Example 31-3] Synthesis of Compound 85-i 45.7 g (67.5 mmol, 1 eq) of 2-(3-(4-chlorophenyl)diphenylsilyl)phenyl)-3,5,6-triphenylpyrazine, 20.6 g (81.0 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (3.4 mmol, 0.04 eq) of PdCl2 (dppf), 6.4 g (13.5 mmol, 0.2 eq) of Xphos, and 15.9 g (162.1 mmol, 2 eq) of KOAc were added to 620 ml of 1,4-dioxane and stirred under reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 85-i,2-(3-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine (40.0 g, yield 77%). Mass:[(M+H)] + ]:692.74 MRN( 1 H): σ=8.50(1H,d), 8.44(1H,s), 8.03(6H,d), 7.85(2H,d), 7.68-7.59(5H,m), 7.46-7.32(18H,m), 1.20(12H,s)

[0200] [Synthesis Example 31-4] Synthesis of Compound 85 40.0 g (52.0 mmol, 1 eq) of 2-(3-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-3,5,6-triphenylpyrazine, 15.3 g (57.2 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.8 g (1.6 mmol, 0.03 eq) of Pd(PPh3)4, and 14.4 g (104.0 mmol, 2 eq) of K2CO3 were placed in 600 ml of toluene, 150 ml of EtOH, and 150 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with sufficient water and MeOH. Next, it was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 85 (target compound B) (37.3 g, yield 82%), a white solid. Mass:[(M+H)] + ]:874.14

[0201] [Synthesis Example 32] Synthesis of Compound 89

[0202] [ka]

[0203] [Synthesis Example 32-1] Synthesis of Compound 89-iii 50 g of (4-bromophenyl)(3-chlorophenyl)diphenylsilane (111.1 mmol, 1 eq), 33.9 g of 4,4,4',4',5,5',5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (133.4 mmol, 1.2 eq), 3.3 g of PdCl2 (dppf) (4.4 mmol, 0.04 eq), and 21.9 g of KOAc (222.3 mmol, 2 eq) were added to 750 mL of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 89-iii, (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.2 g, yield 80%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.55(1H, s), 7.46-7.32(15H, m), 1.20(12H, s)

[0204] [Synthesis Example 32-2] Synthesis of Compound 89-ii 44.2 g (88.9 mmol, 1 eq) of (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 33.5 g (97.8 mmol, 1.1 eq) of 5-(3-chlorophenyl)-2,3-diphenylpyrazine, 3.1 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 24.6 g (177.8 mmol, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and heated under reflux stirring for 6 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 89-ii, 5-(4'-((3-chlorophenyl)diphenylsilyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine (46.4 g, yield 77%). Mass:[(M+H)] + ]:677.32 NMR ( 1 H): σ=8.79(1H, s), 8.50(2H, d), 8.03(2H, d), 7.87(2H, d), 7.77(1H, d), 7.71(1H, d), 7.65-7.55(5H, m), 7.48-7.32(19H, m)

[0205] [Synthesis Example 32-3] Synthesis of Compound 89-i 46.4 g (68.5 mmol, 1 eq) of 5-(4'-((3-chlorophenyl)diphenylsilyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine, 20.9 g (82.2 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (3.4 mmol, 0.04 eq) of PdCl2 (dppf), 6.5 g (13.7 mmol, 0.2 eq) of Xphos, and 16.2 g (164.3 mmol, 2 eq) of KOAc were added to 700 ml of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water and transferred to a separatory funnel. The organic layer was then separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 89-i, 5-(4'-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine (39.0 g, yield 74%). Mass:[(M+H)] + ]:768.84 NMR ( 1 H):σ==8.79(1H,s), 8.50(2H,d), 8.03(2H,d), 7.87-7.85(3H,m), 7.77( 1H,d), 7.71(1H,d), 7.65-7.55(5H,m), 7.48-7.32(18H,m), 1.20(12H,s)

[0206] [Synthesis Example 32-4] Synthesis of Compound 89 39.0 g (50.7 mmol, 1 eq) of 5-(4'-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine, 14.9 g (55.7 mmol, 1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A), 1.8 g (1.5 mmol, 0.03 eq) of Pd(PPh3)4, and 14.0 g (101.3 mmol, 2 eq) of K2CO3 were placed in 550 ml of toluene, 160 ml of EtOH, and 160 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with plenty of water and MeOH. Next, the compound was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 89 (target compound B) (36.3 g, yield 82%) as a white solid. Mass:[(M+H)] + ]:874.14

[0207] [Synthesis Example 33] Synthesis of Compound 90

[0208] [ka]

[0209] [Synthesis Example 33-1] Synthesis of Compound 90-iii 50 g (111.1 mmol, 1 eq) of (4-bromophenyl)(4-chlorophenyl)diphenylsilane, 33.9 g (133.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 3.3 g (4.4 mmol, 0.04 eq) of PdCl2 (dppf), and 21.9 g (222.3 mmol, 2 eq) of KOAc were added to 750 ml of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 90-iii, (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.7 g, yield 81%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.52-7.38(16H, m), 1.20(12H, s)

[0210] [Synthesis Example 33-2] Synthesis of Compound 90-ii 44.7 g (90.0 mol, 1 eq) of (4-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 34.0 g (99.0 mmol, 1.1 eq) of 5-(3-chlorophenyl)-2,3-diphenylpyrazine, 3.1 g (2.7 mmol, 0.03 eq) of Pd(PPh3)4, and 24.6 g (180.1 ml, 2 eq) of K2CO3 were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmolecule (MC). The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 90-ii, 5-(4'-((4-chlorophenyl)diphenylsilyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine (45.7 g, yield 75%). Mass:[(M+H)] + ]:677.32 NMR ( 1 H):σ=8.79(1H,d), 8.50(2H,d), 8.03(2H,d), 7.87-7.85(4H,m), 7.77(1H,d), 7.71(1H,s), 7.65-7.32(22H,m)

[0211] [Synthesis Example 33-3] Synthesis of Compound 90-i 45.7 g (67.5 mmol, 1 eq) of 5-(4'-((4-chlorophenyl)diphenylsilyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine, 20.6 g (81.0 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.5 g (3.4 mmol, 0.04 eq) of PdCl2 (dppf), 6.4 g (13.5 mmol, 0.2 eq) of Xphos, and 15.9 g (162.1 mmol, 2 eq) of KOAc were added to 650 ml of 1,4-dioxane and stirred under reflux for 6 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 90-i, 5-(4'-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine (40.0 g, yield 77%). Mass:[(M+H)] + ]:768.84 NMR ( 1 H):σ=8.79(1H,s), 8.50(2H,d), 8.03(2H,d), 7.87-7.85(4H,m), 7.77-7.59(6H,m), 7.59-7.32(18H,m), 1.20(12H,s)

[0212] [Synthesis Example 33-4] Synthesis of Compound 90 40.0 g of 5-(4'-(diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)-[1,1'-biphenyl]-3-yl)-2,3-diphenylpyrazine (52.0 mmol, 1 eq) and 15.3 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A) (57.2 mmol, 1.1 eq), 1.8 g of Pd (PPh3)4 (1.6 mmol, 0.03 eq), and 14.4 g of K2CO3 (104.0 mmol, 2 eq) were placed in 600 ml of toluene, 150 ml of EtOH, and 150 ml of H2O, and the mixture was stirred under reflux for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with plenty of water and MeOH. Next, the compound was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 90 (target compound B), a white solid (36.4 g, 80% yield). Mass:[(M+H)] + ]:874.14

[0213] [Synthesis Example 34] Synthesis of Compound 118

[0214] [ka]

[0215] [Synthesis Example 34-1] Synthesis of Compound 118-iii 50 g of (4-bromophenyl)(3-chlorophenyl)diphenylsilane (111.1 mmol, 1 eq), 33.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (133.4 mmol, 1.2 eq), 3.3 g of PdCl2 (dppf) (4.4 mmol, 0.04 eq), and 21.9 g of KOAc (222.3 mmol, 2 eq) were added to 750 mL of 1,4-dioxane and stirred under reflux for 4 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 118-iii, ((3-chlorophenyl)diphenyl(4-(4,5,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (44.2 g, yield 80%). Mass:[(M+H)] + ]:496.91 NMR ( 1 H):σ=7.85(2H, d), 7.55(1H, s), 7.46-7.32(15H, m), 1.20(12H, s)

[0216] [Synthesis Example 34-2] Synthesis of Compound 118-ii 44.2 g of (3-chlorophenyl)diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (88.9 mmol, 1 eq), 31.0 g of 5-chloro-2-(naphthalene-2-yl)-3-phenylpyrazine (97.8 mmol, 1.1 eq), 3.1 g of Pd (PPh3)4 (2.7 mmol, 0.03 eq), and 24.6 g of K2CO3 (177.8 mmol, 2 eq) were placed in 650 ml of toluene, 180 ml of EtOH, and 180 ml of H2O, and the mixture was stirred under heating and reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted by adding methylmol. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 118-ii, 5-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-2-(naphthalene-2-yl)-3-phenylpyrazine (38.2 g, yield 66%). Mass: [(M+H)] + ]: 651.28 NMR ( 1 H): σ= 9.02(1H, d), 8.79(1H, s), 8.54(1H, d), 8.43(2H, d), 8.10-8.00(5H, m), 7.69(2H, d), 7.61-7.32(19H, m).

[0217] [Synthesis Example 34-3] Synthesis of Compound 118-i 38.2 g (58.7 mmol, 1 eq) of 5-(4-((3-chlorophenyl)diphenylsilyl)phenyl)-2-(naphthalene-2-yl)-3-phenylpyrazine and 17.9 g (70.4 mmol, 1.2 eq) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 2.1 g (2.9 mmol, 0.04 eq) of PdCl2(dppf), 5.6 g (11.7 mmol, 0.2 eq) of Xphos, and 13.9 g (140.8 mmol, 2 eq) of KOAc were added to 550 ml of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was complete, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated and then adsorbed onto silica gel and purified by column chromatography to obtain compound 118-i, 5-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2-(naphthalene-2-yl)-3-phenylpyrazine (33.1 g, yield 76%). Mass: [(M+H)] + ]: 742.80 NMR ( 1 H) : σ= 9.02(1H, s), 8.79(1H, s),8.54(1H, d), 8.43(2H, d), 8.10-8.00(5H,m), 7.85(1H, d), 7.69(2H) m), 7.46-7.32(14H, m), 1.20(12H, s)

[0218] [Synthesis Example 34-4] Synthesis of Compound 118 33.1 g of 5-(4-(diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silyl)phenyl)-2-(naphthalene-2-yl)-3-phenylpyrazine (44.6 mmol, 1 eq) and 13.1 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (intermediate A) (49.1 mmol, 1.1 eq), 1.5 g of Pd(PPh3)4 (1.3 mmol, 0.03 eq), and 12.3 g of K2CO3 (89.2 mmol, 2 eq) were placed in 500 ml of toluene, 140 ml of EtOH, and 140 ml of H2O, and the mixture was heated under reflux and stirred for 8 hours. After the reaction was complete, the precipitated solid was deactivated with a sufficient amount of water, filtered, and washed with plenty of water and MeOH. Next, the compound was adsorbed onto silica gel and purified by column chromatography. After concentration, the mixture was stirred with a small amount of EA and hexane, and the resulting solid was filtered to obtain compound 118 (target compound B), a white solid (29.1 g, yield 77%). Mass: [(M+H)] + ]: 848.10

[0219] [Reference example] The structures of compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3 E-1, E-2, E-3, E-4, and E-5 used in Examples 1 to 66 and Comparative Examples 1 to 12 are as follows.

[0220] [ka]

[0221] [Examples 1-34] Fabrication of blue organic electroluminescent elements After purifying the compound synthesized in the above synthesis example to high purity using a conventional method, a blue organic electroluminescent element was fabricated using it as an electron transport layer material according to the following procedure.

[0222] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, Fascintec). The substrate was then cleaned with UV light for 5 minutes and transferred to a vacuum deposition machine.

[0223] An organic electroluminescent device was fabricated by stacking layers in the following order on the ITO transparent electrode prepared as described above: HI+2%HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH+2%BD (20 nm) / electron transport layer material from Table 1 + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm).

[0224] [Comparative Examples 1-6] Manufacturing of Blue Organic Electroluminescent Elements The blue organic electroluminescent elements of Comparative Examples 1 to 6 were fabricated in the same manner as in Example 1, except that Alq3, E-1, E-2, E-3, E-4, and E-5 were used instead of compound 1 as the electron transport layer material.

[0225] [Evaluation Example 1] For the organic electroluminescent elements manufactured in Examples 1-34 and Comparative Examples 1-6, the current density was 10 mA / cm². 2 The driving voltage, emission wavelength, and current efficiency were measured, and the results are shown in Table 5 below.

[0226] [Table 5] JPEG2026530485000074.jpg93112

[0227] As shown in Table 1 above, the organic electroluminescent elements of Examples 1 to 34, which used the compound according to the present invention as the electron transport layer material, were found to be significantly superior to the blue organic electroluminescent elements of Comparative Examples 1 to 6, which used conventional Alq3 and compounds E-1 to E-4 that do not contain the essential components of the present invention as the electron transport layer material.

[0228] [Examples 35-68] Fabrication of a blue organic electroluminescent device After purifying the compound synthesized in the above synthesis example to high purity using a conventional method, a blue organic electroluminescent element was fabricated using it as an electron transport auxiliary layer material according to the following process.

[0229] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, Fascintec). The substrate was then cleaned with UV light for 5 minutes and transferred to a vacuum deposition machine.

[0230] An organic electroluminescent device was fabricated by stacking the following layers on the ITO transparent electrode prepared as described above: HI+2%HAT-CN6 (10nm) / HI (140nm) / EB (5nm) / BH+2%BD (20nm) / electron transport auxiliary layer material from Table 1 (5nm) / ET+Liq (1:1) (30nm) / LiF (1nm) / Al (100nm).

[0231] [Comparative Examples 7-12] Manufacturing of Blue Organic Electroluminescent Devices The blue organic electroluminescent elements of Comparative Examples 7 to 12 were fabricated in the same manner as in Example 35, except that the electron transport auxiliary layer was omitted or compounds E-1 to E-5 were used instead of compound 1 as the electron transport auxiliary layer material.

[0232] [Evaluation Example 2] Evaluation Example: Driving Voltage Measurement For the organic electroluminescent elements manufactured in Examples 35-68 and Comparative Examples 7-12, the current density was 10 mA / cm². 2 The driving voltage, emission wavelength, and current efficiency were measured, and the results are shown in Table 6 below.

[0233] [Table 6] JPEG2026530485000076.jpg92123

[0234] As shown in Table 6 above, the organic electroluminescent elements of Examples 35 to 68, which used the compounds according to the present invention as electron transport auxiliary layer materials, were found to be superior in terms of driving voltage, light emission peak, and current efficiency compared to the organic electroluminescent elements of Comparative Examples 7 to 12, which used conventional E-1 to E-5 compounds as electron transport auxiliary layer materials that either did not contain an electron transport auxiliary layer or did not contain the essential components of the present invention.

[0235] As can be seen from the results in Tables 5 and 6 above, when the silane compound according to the present invention is used as an electron transport layer material, an improvement in the device's driving voltage is obtained, and furthermore, when the compound is used as an electron transport auxiliary layer material, the efficiency of the device is significantly improved.

[0236] More specifically, the compounds according to the present invention, in which triazine and pyrazine are substituted as dual EWG units, were found to exhibit superior properties compared to compounds ET-1 to ET-5 used as comparative examples.

[0237] As an example, it was confirmed that the device of the example containing a compound having dual EWG groups on both sides of a silyl group according to the present invention exhibits superior driving voltage characteristics compared to the devices of Comparative Examples 2-4 and 8-10, which use compounds E-1 to E-3 as electron transport layer / electron transport auxiliary layer materials. This is presumed to be because conventional materials E-1 to E-3 have an EWG group on one side of a silyl group consisting of an SP3 orbital, while the other side is substituted with an arylene group, which increases the molecular size but does not increase electron mobility, and therefore does not have appropriate electron mobility.

[0238] On the other hand, Comparative Examples 5 and 11, which used an E-4 compound having two triazines as dual EWG groups on both sides of a silyl group as an electron transport layer / electron transport auxiliary layer material, exhibited similar drive voltage characteristics to the devices of the present invention, but their efficiency characteristics were not sufficient. This is because the compound of the present invention, with its silyl group flanked by two different dual EWG groups, such as triazine and pyrazine, has a structural asymmetry resulting in a high triplet (T1) energy level. This, combined with the low voltage characteristics of pyrazine, effectively lowers the drive voltage of the device and further increases the strong electron-withdrawing properties of the azine group, significantly improving the device's high-efficiency characteristics. In particular, because the compound of the present invention has an asymmetric structure, it does not have a crystallization temperature (Tc) in its thermal properties, which is advantageous in terms of processability.

[0239] Furthermore, a comparison of Comparative Examples 2 and 6, and Comparative Examples 8 and 12, which used compounds E-1 and E-5 as electron transport layer / electron transport auxiliary layer materials, revealed that while increasing the number of intramolecular silyl groups can improve the efficiency characteristics of the device, it also increases the volume of the structure, hindering electron flow and resulting in an unfavorable driving voltage.

[0240] Furthermore, a comparison of Comparative Examples 8-10 and 12, which use compounds E-1-E-3 and E-5 as electron transport auxiliary layer materials, revealed that while the properties of the silyl group are useful in improving the efficiency characteristics of the device as an electron transport auxiliary layer, they are disadvantageous in terms of driving voltage. In Comparative Example 11, which uses compound E-4 as the electron transport auxiliary layer material, the symmetrical structure due to the two triazines results in a triplet energy level and unstable thermal properties. This is judged to result in a lower overall efficiency of the device compared to the effect of improving the driving voltage of the device.

Claims

1. The compound represented by the following chemical formula 1: 【Chemistry 1】 (In the above chemical formula 1, Ar 1 to Ar 3 are the same as or different from each other, and are each independently hydrogen, deuterium (D), C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 arylphosphine oxide group and C 6 to C 60 arylamine group, selected from the group consisting of the foregoing, and a case where at least two or more of Ar 1 to Ar 3 are hydrogen is excluded, X １ ~X ５ These are either identical or different from each other, and each is independent of C(R). １ ) or N, however X １ ~X ５ At least two of them are N, R 1 If there are multiple R 1 These are identical or different from each other, and independently of each other, hydrogen, deuterium (D), halogen, cyano group, nitro group, and C 1 ~C 40 alkyl group, C 2 ~C 40 The alkenyl group, C 2 ~C 40 The alkynyl group, C 3 ~C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C 6 ~C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~C 40 The alkyloxy group, C 6 ~C 60 The aryloxy group, C 3 ~C 40 The alkylsilyl group, C 6 ~C 60 The arylsilyl group, C 1 ~C 40 alkylboron group, C 6 ~C 60 The arylboron group, C 6 ~C 60 The arylphosphine group, C 6 ~C 60 The arylphosphine oxide group and C 6 ~C 60 Selected from the group consisting of arylamine groups, in this case, multiple R 1 Two of them are B 1 and B 2 It is expressed as, A 1 to A 2 and B 1 to B 2 are the same as or different from each other, and are each independently hydrogen, deuterium (D), C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkylboron group, C 6 to C 60 arylboron group, C 6 to C 60 arylphosphine group, C 6 to C 60 arylphosphine oxide group and C 6 to C 60 arylamine group, selected from the group consisting of L １ and L ２ They are either identical or different from each other, independent of each other, and are single-bonded or C ６ ~C １８ Selected from the group consisting of arylene groups and heteroarylene groups with 5 to 18 nuclear atoms, d and e are each independent integers between 0 and 4. Said L １ ~L ２ Arylene groups and heteroarylene groups, and the Ar １ ~Ar ３ , R １、 A １ ~A ２ , B １～ B ２ The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, phosphine group, phosphine oxide group, and arylamine group are each independently deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 alkyl group, C 2 ~C 40 The alkenyl group, C 2 ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C 6 ~C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 ~C 40 The alkyloxy group, C 6 ~C 60 The aryloxyl group, C 1 ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C 1 ~C 40 alkylboron group, C 6 ~C 60 The arylboron group, C 6 ~C 60 The arylphosphine group, C 6 ~C 60 The arylphosphine oxide group and C 6 ~C 60 It can be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, if there are multiple substituents, they may be the same or different from one another.

2. The aforementioned X １ ~X ５ The compound according to claim 1, wherein the contained ring is selected from any of the following structural formulas: 【Chemistry 2】 (In the above formula, * indicates the linkage site with chemical formula 1, R １ , B １ and B ２ (These are the same as the definitions in Claim 1.)

3. A １～ A ２ and B １ ~B ２ They are either identical or different from each other, and each is independent of C ６ ~C ６０ The compound according to claim 1, selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

4. A 1 ~A 2 and B 1 ~B 2 The compounds according to claim 1, which are identical or different from each other and are independently selected from the following structural formulas: 【Transformation 3】 【change】 (In the above formula, * indicates the linkage site with chemical formula 1, R 2 It consists of hydrogen, deuterium (D), and C. 1 ~C 40 alkyl group, C 6 ~C 60 (Selected from the group consisting of aryl groups and heteroarylene groups with 5 to 18 nuclear atoms.)

5. Ar １ ~Ar ３ These are either identical or different from each other, and each is independently hydrogen, deuterium (D), and C. １ ~C ４０ alkyl group, C ６ ~C ６０ Selected from the group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclear atoms, where Ar １ ~Ar ３ The compound according to claim 1, which is excluded if at least two of the elements are hydrogen.

6. Ar １ ~Ar ３ The compounds according to claim 1, which are identical or different from each other and are independently selected from the following structural formulas: 【Chemistry 4】 (In the above formula, * indicates the linkage site with chemical formula 1, R 3 It consists of hydrogen, deuterium (D), and C. 1 ~C 40 alkyl group, C 6 ~C 60 (Selected from the group consisting of aryl groups and heteroarylene groups with 5 to 18 nuclear atoms.)

7. L １ and L ２ The compounds according to claim 1, which are identical or different from each other and are independently selected from the following structural formulas: 【Transformation 5】 (In the above formula, * indicates the linkage site with chemical formula 1.

8. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by the following chemical formula 2. 【Transformation 6】 (In the above formula, X 1 ~X 5 Ar 1 ~Ar 3 A 1 ~A 2 B 1 ~B 2 d and e are defined as in claim 1, respectively.

9. The above formula (2) 【Transformation 7】 The compounds according to claim 8, which are identical or different from each other and are independently selected from the following structural formulas: 【Transformation 8】 (In the above formula, * indicates the linkage site with chemical formula 2.

10. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any of the following chemical formulas 3 to 5: 【Chemistry 9】 (In the above formula, X 1 ~X 5 Ar 1 ~Ar 3 , A 1 ~A 2 , B 1 ~B 2 d and e are defined as in claim 1, respectively.

11. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any one of the following chemical formulas 6a to 6l: 【Chemistry 10】 【change】 【change】 【change】 【change】 (In the above formula, Ar 1 ~Ar 3 , A 1 ~A 2 B 1 ~B 2 , R 1 , and d are defined as in Claim 1, respectively.

12. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any one of the following chemical formulas 7 to 9: 【Chemistry 11】 【change】 (In the above formula, X 1 ~X 5 Ar 1 ~Ar 3 , A 1 ~A 2 B 1 ~B 2 d and e are defined as in claim 1, respectively.

13. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any one of the following chemical formulas 10a to 10l: 【Chemistry 12】 【change】 【change】 【change】 【change】 (In the above formula, X 1 ~X 5 Ar 1 ~Ar 3 , A 1 ~A 2 B 1 ~B 2 , and e are defined as in Claim 1, respectively.

14. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any one of the following chemical formulas 11 to 14: 【Chemistry 13】 【change】 (In the above formula, Ar 1 ~Ar 3 , A 1 ~A 2 B 1 ~B 2 d and e are defined as in claim 1, respectively.

15. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any one of the following chemical formulas 15 to 18: 【Chemistry 14】 【change】 (In the above formula, X 1 ~X 5 Ar 1 ~Ar 3 , A 1 ~A 2 B 1 ~B 2 , L 1 ~L 2 d and e are as defined in claim 1, respectively, except Ar 1 ~Ar 3 (If it is hydrogen, it is excluded.)

16. The compound represented by the aforementioned chemical formula 1 is the compound according to claim 1, which is represented by any of the following chemical formulas 1 to 128. 【Chemistry 15】 【change】 【change】 【change】 【change】 【change】 【change】

17. The compound according to claim 1, wherein the compound represented by chemical formula 1 is a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, or an electron transport auxiliary layer material.

18. An organic electroluminescent element comprising a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers contains a compound according to any one of claims 1 to 17.

19. The organic electroluminescent element according to claim 18, wherein the organic layer containing the compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a life-improving layer, an electron transport layer, and an electron transport auxiliary layer.

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