Organic compound and organic electroluminescent device using same

Abstract

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

Description

Organic compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0005] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0006] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0007] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0008]

[0009] The present invention aims to provide a novel organic compound that can be applied to organic electroluminescent devices and exhibits excellent hole, electron injection and transport capabilities, and luminescence capabilities.

[0010] In addition, another objective of the present invention is to provide an organic electroluminescent device comprising the novel organic compound described above, which exhibits a low driving voltage and high luminous efficiency and has an improved lifespan.

[0011]

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

[0013] [Chemical Formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] A plurality of Xs are identical or different from one another, and each is independently CR5 or N, provided that at least two of the plurality of Xs are N,

[0017] Ar1 and R5 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei,

[0018] L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei,

[0019] m and n are each independently integers from 0 to 3, and

[0020] R1 to R4, and R 11 to R 14 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group;

[0021] a to c, e to g are each independently integers from 0 to 5, and

[0022] d and h are each independently integers from 0 to 4, and

[0023] The arylene group and heteroarylene group of L1 to L2 above; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group of Ar1 and R5 above; The above R1~R 4, R 11 ~R 14The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, wherein if there are multiple substituents, they may be identical or different from each other.

[0024] However, the compound represented by the above chemical formula 1 has an asymmetric structure based on the X-containing ring.

[0025] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0026] Here, the organic layer comprising the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a 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 material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0027]

[0028] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0029] In particular, when a compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional electron transport materials.

[0030] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0031] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0032]

[0033] The present invention will be described in detail below.

[0034] <New Organic Compounds>

[0035] According to the present invention, a compound represented by Formula 1 comprises two silane moietyes (e.g., tetraphenylsilane) centered around a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) and has a basic skeletal structure in which they are directly connected or connected through a separate linker (e.g., L1-L2), wherein the two silane moietyes have an asymmetric structure centered around the azine group.

[0036] Specifically, the compound of Chemical Formula 1 contains two silane moiety groups with electron donor (EDG) characteristics and a nitrogen-containing aromatic ring (e.g., pyrimidine, triazine), which is a type of electron-withdrawing (EWG) group with high electron absorption. By introducing an azine group, which is a functional group with strong electron-withdrawing ability (EWG), the electron mobility is improved, thereby enabling the device to possess physicochemical properties more suitable for electron injection and electron transport. When the compound of Chemical Formula 1 described above is applied as a material for an electron transport layer or an electron transport auxiliary layer, electrons from the cathode can be effectively accepted, allowing for smooth electron transfer to the light-emitting layer. Consequently, this enables a reduction in the driving voltage of the device, leading to high efficiency and a long lifespan. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0037] In addition, the two silane moiety (e.g., tetraphenylsilane) included in the compound of Chemical Formula 1 above has excellent electron accepting ability because all three hydrogens of the silyl group are substituted with an aryl-phenyl group or a heteroaryl-phenyl group. Furthermore, by including silicon instead of carbon, the electrical conductivity is enhanced in addition to the electron donor properties of the existing aryl groups, thereby further enhancing the electron donor properties and enabling a synergy effect in terms of electron transport.

[0038] Furthermore, since the above silane-based moiety is formed as a bulky substituent in a form where conjugation is discontinued, it possesses a wide energy bandgap and a high excited triplet energy level, and accordingly, it can exhibit excellent electron transport capacity not only in fluorescent luminescence but also in phosphorescent materials.

[0039] In addition, the two silane moiety types have a high triplet energy (T1) value through steric hindrance, so they can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. Furthermore, the number of excitons contributing to light emission within the light-emitting layer can be increased, thereby improving the luminous efficiency of the device and enhancing the durability and stability of the device, which can efficiently increase the lifespan of the device.

[0040] In addition, when silane groups are used on both sides centered around an argin group which is an EWG, the glass transition temperature (Tg) is low relative to the molecular weight, which may lead to thermal stability issues. In contrast, the present invention introduces a multi-aryl moiety on at least one or both sides of two silane moietys, thereby overcoming the low glass transition temperature (Tg) of conventional silane-containing compounds and securing a glass transition temperature (Tg) of 120°C or higher to solve thermal stability problems. Additionally, since mobility can be controlled, it is easy to achieve charge balance.

[0041] Furthermore, the compound represented by Chemical Formula 1 above forms an asymmetric structure in terms of molecular structure based on an argin group (e.g., an X-containing ring). Specifically, the asymmetric structure can be achieved by having two silane moietyes asymmetrically bonded around an argin group, asymmetrically bonded around a linker (e.g., L1-L2), having different types of linkers, controlling the number of linkers differently, and / or having different types of at least one substituent connected to the two silane moietyes. Such an asymmetric structure allows for the control of intermolecular packing density, which facilitates electron transport and exhibits characteristics such as low driving voltage, high efficiency, and long lifespan. The excellent electron transport capability of the compound having the aforementioned structure enables high efficiency and rapid mobility in organic electroluminescent devices, and facilitates the control of HOMO and LUMO energy levels depending on the direction or position of the substituents. Therefore, an organic electroluminescent device using the above compound can exhibit high electron transport capability.

[0042] Meanwhile, the red and green light-emitting layers of organic electroluminescent devices utilize phosphorescent materials, and their technological maturity is currently high. In contrast, the blue light-emitting layer consists of fluorescent and phosphorescent materials; however, the fluorescent material requires performance improvement, and the blue phosphorescent material is still under development, resulting in a high barrier to entry. In other words, while the blue light-emitting layer has great potential for development, the technical difficulty is relatively high, which limits the ability to improve the performance (e.g., driving voltage, efficiency, lifespan, etc.) of blue organic light-emitting devices equipped with it. Accordingly, in the present invention, the compound of Chemical Formula 1 can be applied as an electron transport layer (ETL) or an electron transport auxiliary layer material in addition to the light-emitting layer (EML). Thus, there is an advantage in that the performance of the light-emitting layer, specifically the blue light-emitting layer, and the performance of the organic electroluminescent device equipped with it can be improved by changing the material of the electron transport layer or the electron transport auxiliary layer used as a common layer in the organic electroluminescent device.

[0043] According to the present invention, a compound represented by Formula 1 comprises a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) with excellent electron transport capacity and EWG characteristics, and two silane moietyes (e.g., tetraphenylsilane), and has a basic skeletal structure in which they are directly connected or connected through separate linkers (e.g., L1 to L2), and is characterized by having an asymmetric structure with respect to the nitrogen-containing heteroaromatic ring.

[0044] For example, the above compound can form an asymmetric structure by satisfying at least one of the following conditions (i) to (iv).

[0045] (i) the above R1~R4 containing silane groups and the above R 11 ~R 14 The contained silane groups are asymmetrically bonded to each other based on the X-containing ring.

[0046] (ii) the above R1~R4 containing silane groups and the above R11 ~R 14 The contained silane groups are asymmetrically coupled with each other with respect to the linkers L1 and L2. In this case, L1 and L2 are each non-single linkers, and n and m are each integers greater than or equal to 1.

[0047] (iii) Linkers L1 and L2 are different from each other, where n and m are integers greater than or equal to 1.

[0048] (iv) The number of linkers, n and m, are different, and L1 and L2 are each non-single linkers.

[0049] In Formula 1 according to the present invention, the nitrogen-containing heterocyclic ring (e.g., X-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. In one example of a nitrogen-containing heteroaromatic ring, X may be identical or different from each other, and each may independently be CR5 or N, provided that at least two of the plurality of Xs contain N. By including a heterocyclic ring containing two to three nitrogen atoms in this way, superior electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

[0050] Here, R5 are identical or different from each other and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple R5s, the multiple R5s may be identical or different from each other. Specifically, R5 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0051] For example, a nitrogen-containing heterocyclic ring (e.g., a ring containing X) may be further specified by any one selected from the following structural formulas. However, it is not limited thereto.

[0052]

[0053] In the above formula,

[0054] * indicates the part connected to the above chemical formula 1, and

[0055] Ar1 is as defined in Chemical Formula 1.

[0056] In the above nitrogen-containing heterocyclic rings (e.g., X-containing rings), Ar1 can be substituted as various substituents. Ar1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar1 is C1~C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 The alkyl group, aryl group, heteroaryl group and arylsilyl group of Ar1 are each independently selected from the group consisting of arylsilyl groups, wherein the alkyl group, aryl group, heteroaryl group and arylsilyl group of Ar1 are each independently deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0057] For example, Ar1 may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0058]

[0059]

[0060]

[0061] In the above formula,

[0062] * indicates the part connected to the above chemical formula 1, and

[0063] R 21 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, at least one substituent known in the art (e.g., identical to the R5 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0064] In the compound represented by Formula 1 according to the present invention, two silane moietyes are included on both sides of the nitrogen-containing heteroaromatic ring (e.g., a ring containing azine, X). These two silane moietyes form a structure that is asymmetrically bonded with respect to the nitrogen-containing heteroaromatic ring (e.g., a ring containing azine, X).

[0065] These two silane moietyes have excellent electron acceptance capabilities because all three hydrogens of the silyl group are substituted with either an aryl group-phenyl group or a heteroaryl group-phenyl group. In addition, by including silicon instead of carbon, electrical conductivity is enhanced in addition to the electron donor properties of the existing aryl groups, further improving electron donor properties and thereby enabling a synergy effect in terms of electron transport.

[0066] In addition, since silane moiety is formed as a bulky substituent with discontinued conjugation, it possesses a wide energy bandgap and a high excited triplet energy level, thereby enabling excellent electron transport capacity not only in fluorescence but also in phosphorescent materials.

[0067] R1 to R4 introduced into the two silane-based moiety above, and R 11 to R 14 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or may form a condensation ring by combining with any adjacent group. Specifically, R1 to R4, and R 11 to R 14 are identical or different from each other, and each independently hydrogen, deuterium (D), cyano group, halogen, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0068] The above R1 to R4, and R 11 to R 14 The number of substituents is not particularly limited. For example, a to c and e to g are each independently integers from 0 to 5, and d and h are each independently integers from 0 to 4. Specifically, a to h are each integers from 0 to 3. Here, if a is 0, R1 is a hydrogen, and if a is 1 to 5, R1 may have the aforementioned substituents excluding hydrogen. Also, R2~R4, R 11 ~R 14 The same can be applied to b~h as well.

[0069] In the compound represented by Formula 1 according to the present invention, a nitrogen-containing heteroaromatic ring (e.g., azine, X-containing ring) and two silane moietyes may be directly bonded or bonded through separate linkers (L1-L2). When separate linkers (L1-L2) exist between the nitrogen-containing heteroaromatic ring and the two silane moietyes, the HOMO region is expanded to provide a benefit to the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO. In addition, by controlling the bonding position between the silane moiety and the linker, additional steric hindrance of the molecular structure can be generated, thereby inducing delocalization of LUMO orbitals and allowing for the control of LUMO values ​​suitable for an electron transport layer or an electron transport auxiliary layer.

[0070] These linkers (L1-L2) may be conventional divalent group linkers known in the art. Specifically, L1 and L2 may be identical or different from each other, and each may independently be a single bond or C6~C 24 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei.

[0071] m and n are integers from 0 to 3. Here, when n is 0, L1 is a single bond (direct bond), and when n is 1 to 3, it may have one or more selected from the group consisting of the aforementioned arylene group and heteroarylene group. Also, m and L2 may be applied in the same way. In this case, if there are multiple L1 or L2, the multiple L1 and L2 may be identical or different from each other.

[0072] Specific examples of the above arylene group linker include phenylene, biphenylene, naphthylene, anthracenylene, indenylene, or pyrantrenylene groups. More specifically, it is preferable that it be a phenylene group or a biphenylene group. In addition, specific examples of heteroarylene group linkers include pyrrole moiety, furan moiety, thiophene moiety, pyridine moiety, pyrimidine moiety, pyrazine moiety, triazine moiety, dibenzofuran moiety, dibenzothiophene moiety, dibenzoselenophenone moiety, carbazolilene group, thiophenylene group, indolylene group, furinilene group, quinolinylene group, pyrroleylene group, imidazolilene group, oxazolilene group, or thiazolilene group.

[0073] For example, L1 and L2 may be identical or different from each other, and each may be independently a single bond or embodied in any one selected from the following structural formulas. However, this is not limited thereto.

[0074]

[0075] In the above formula,

[0076] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R5 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0077] In the aforementioned Chemical Formula 1, the arylene group and heteroarylene group of L1 to L2; and Ar1 and R1 to R 5, R 11 ~R 14 The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0078] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 2 to 5 below, depending on the type of nitrogen-containing heteroaromatic ring (e.g., X-containing ring). However, it is not limited thereto.

[0079] [Chemical Formula 2]

[0080]

[0081] [Chemical Formula 3]

[0082]

[0083] [Chemical Formula 4]

[0084]

[0085] [Chemical Formula 5]

[0086]

[0087] In the above formula,

[0088] Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each defined in Chemical Formula 1.

[0089] The compound represented by Formula 1 according to the present invention can form an asymmetric structure by asymmetrically bonding two silane moietyes connected to a nitrogen-containing heteroaromatic ring.

[0090] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 6 to 11 below, depending on the bonding positions of the two silane moieties connected to the azinum group. However, it is not limited thereto.

[0091] [Chemical Formula 6]

[0092]

[0093] [Chemical Formula 7]

[0094]

[0095] [Chemical Formula 8]

[0096]

[0097] [Chemical Formula 9]

[0098]

[0099] [Chemical Formula 10]

[0100]

[0101] [Chemical Formula 11]

[0102]

[0103] In the above formula,

[0104] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14, a, b, c, d, e, f, g, h, m, and n are each defined in Chemical Formula 1.

[0105] For a preferred specific example, the compound represented by the above chemical formulas 6 to 11 is R1 to R4, R 11 ~R 14 And according to a~h, it can be further embodied in any one of the following chemical formulas 6A to 11A.

[0106] [Chemical Formula 6A]

[0107]

[0108] [Chemical Formula 7A]

[0109]

[0110] [Chemical Formula 8A]

[0111]

[0112] [Chemical Formula 9A]

[0113]

[0114] [Chemical Formula 10A]

[0115]

[0116] [Chemical Formula 11A]

[0117]

[0118] In the above formula,

[0119] X, Ar1, L1~L2, m and n are each defined in Chemical Formula 1.

[0120] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 12 to 15 below depending on the number of linkers. However, it is not limited thereto.

[0121] [Chemical Formula 12]

[0122]

[0123] [Chemical Formula 13]

[0124]

[0125] [Chemical Formula 14]

[0126]

[0127] [Chemical Formula 15]

[0128]

[0129] In the above formula,

[0130] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in Chemical Formula 1, provided that cases where m and n are each 0 are excluded.

[0131] In a preferred specific example, the compound represented by the chemical formulas 12 to 15 is R1 to R4, R 11 ~R 14 And according to a~h, it can be further embodied in any one of the following chemical formulas 12A to 15A.

[0132] [Chemical Formula 12A]

[0133]

[0134]

[0135] [Chemical Formula 13A]

[0136]

[0137] [Chemical Formula 14A]

[0138]

[0139] [Chemical Formula 15A]

[0140]

[0141] In the above formula,

[0142] X, Ar1, L1~L2, m and n are each defined as in Chemical Formula 1, provided that cases where m and n are each 0 are excluded.

[0143] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 16 to 24 below, depending on the type of linker (e.g., L1-L2). However, it is not limited thereto.

[0144] [Chemical Formula 16]

[0145]

[0146] [Chemical Formula 17]

[0147]

[0148] [Chemical Formula 18]

[0149]

[0150] [Chemical Formula 19]

[0151]

[0152] [Chemical Formula 20]

[0153]

[0154] [Chemical Formula 21]

[0155]

[0156] [Chemical Formula 22]

[0157]

[0158] [Chemical Formula 23]

[0159]

[0160] [Chemical Formula 24]

[0161]

[0162] In the above formula,

[0163] X, Ar1, R 1~ R4, R 11 ~R 14, a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and

[0164] Y1 and Y2 are identical or different from each other, and each independently O, S, NR 31 , and CR 32 R 33 It is selected from a group consisting of,

[0165] R 31 to R 33 They are identical or different from each other, and each independently hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei,

[0166] Rings A1 and A2 are identical or different from each other and are each independently condensed polycyclic aromatic rings having 8 to 18 carbon atoms.

[0167] In a preferred specific example, the compound represented by the chemical formulas 16 to 24 is R1 to R4, R 11 ~R 14 And according to a~h, it can be further embodied in any one of the following chemical formulas 16A to 24A.

[0168] [Chemical Formula 16A]

[0169]

[0170] [Chemical Formula 17A]

[0171]

[0172] [Chemical Formula 18A]

[0173]

[0174] [Chemical Formula 19A]

[0175]

[0176] [Chemical Formula 20A]

[0177]

[0178] [Chemical Formula 21A]

[0179]

[0180] [Chemical Formula 22A]

[0181]

[0182] [Chemical Formula 23A]

[0183]

[0184] [Chemical Formula 24A]

[0185]

[0186] In the above formula,

[0187] X, Ar1, m, and n are each as defined in Chemical Formula 1, and

[0188] Y1~Y2 and rings A1~A2 are each as defined in chemical formulas 16 to 24.

[0189] For example, one specific example is the above chemical formula 16. and They may be identical or different from each other, and each may be independently selected from the following structural formulas.

[0190]

[0191]

[0192] In the above formula,

[0193] * indicates the part connected to the above chemical formula 16.

[0194] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 25 to 29 below, depending on the type of Ar1 introduced into the nitrogen-containing heteroaromatic ring (e.g., X-containing ring) which is an azine group. However, it is not limited thereto.

[0195] [Chemical Formula 25]

[0196]

[0197] [Chemical Formula 26]

[0198]

[0199] [Chemical Formula 27]

[0200]

[0201] [Chemical Formula 28]

[0202]

[0203] [Chemical Formula 29]

[0204]

[0205] In the above formula,

[0206] X, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and

[0207] Ring B is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms, and

[0208] Ring C is a cycloalkyl group or an adamantane group having 3 to 12 carbon atoms, and

[0209] Z1 is O, S, NR 41 , and CR 42 R 43 It is selected from a group composed of,

[0210] Z2 is N, and

[0211] R 41 to R 43 Each independently consists of hydrogen, deuterium, and C1~C 20 alkyl group of, C6~C 20 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 20 nuclei,

[0212] o is an integer from 1 to 3.

[0213] As a preferred specific example, the compound represented by the chemical formulas 25 to 29 is R1 to R4, R11 ~R 14 And according to a~h, it can be further embodied in any one of the following chemical formulas 25A to 29A.

[0214] [Chemical Formula 25A]

[0215]

[0216] [Chemical Formula 26A]

[0217]

[0218] [Chemical Formula 27A]

[0219]

[0220] [Chemical Formula 28A]

[0221]

[0222] [Chemical Formula 29A]

[0223]

[0224] In the above formula,

[0225] X, R 1~ R4, m, and n are each as defined in Chemical Formula 1, and

[0226] Rings B, C, Z1, Z2, and o are each defined in chemical formulas 25 to 29.

[0227] As another preferred specific example, the compound represented by Chemical Formulas 26 to 29 above may be further embodied in any one of Chemical Formulas 30 to 39 below.

[0228] [Chemical Formula 30]

[0229]

[0230] [Chemical Formula 31]

[0231]

[0232] [Chemical Formula 32]

[0233]

[0234] [Chemical Formula 33]

[0235]

[0236] [Chemical Formula 34]

[0237]

[0238] [Chemical Formula 35]

[0239]

[0240] [Chemical Formula 36]

[0241]

[0242] [Chemical Formula 37]

[0243]

[0244] [Chemical Formula 38]

[0245]

[0246] [Chemical Formula 39]

[0247]

[0248] In the above formula,

[0249] X, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and

[0250] R 41 to R 43 Each is as defined in Chemical Formulas 26 to 29. In addition, at least one substituent known in the art (e.g., identical to the R5 definition) that is not indicated in the aforementioned structural formulas may be substituted.

[0251] Meanwhile, the compound represented by Formula 1 according to the present invention can form an asymmetric structure by differently controlling the bonding positions between the two silane moiety and the linker (e.g., L1-L2), and the type and / or number of linkers connected to the two silane moiety. At this time, the two silane moiety connected to the nitrogen-containing heteroaromatic ring may be structured such that they are symmetrically bonded to each other, but are not limited thereto.

[0252] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 40 to 45 below, depending on the number of linkers (e.g., m, n) connected to two silane moiety. However, it is not limited thereto.

[0253] [Chemical Formula 40]

[0254]

[0255] [Chemical Formula 41]

[0256]

[0257] [Chemical Formula 42]

[0258]

[0259] [Chemical Formula 43]

[0260]

[0261] [Chemical Formula 44]

[0262]

[0263] [Chemical Formula 45]

[0264]

[0265] In the above formula,

[0266] X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Chemical Formula 1, and

[0267] m and n are integers from 1 to 3, respectively, provided that m and n are different from each other in chemical formulas 43 to 45.

[0268] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 46 to 48 below, depending on the bonding position of the linker (e.g., L1-L2) connected to the two silane moiety. However, it is not limited thereto.

[0269] [Chemical Formula 46]

[0270]

[0271] [Chemical Formula 47]

[0272]

[0273] [Chemical Formula 48]

[0274]

[0275] In the above formula,

[0276] X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Chemical Formula 1, and

[0277] m and n are integers from 1 to 3, respectively, and

[0278] The above and Each is independently selected from the following structural formulas, but is distinct from one another, and

[0279]

[0280]

[0281] In the above formula,

[0282] * indicates a region connected to the above chemical formulas 46 to 48.

[0283] In another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 49 to 51 below, depending on the type of linker (e.g., L1-L2) connected to the two silane moiety. However, it is not limited thereto.

[0284] [Chemical Formula 49]

[0285]

[0286] [Chemical Formula 50]

[0287]

[0288] [Chemical Formula 51]

[0289]

[0290] In the above formula,

[0291] X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Chemical Formula 1, and

[0292] L1 and L2 are each independently single bonds, or are selected from the following structural formulas, but are different from each other,

[0293]

[0294] In the above formula,

[0295] * indicates a region connected to the above chemical formulas 49 to 51.

[0296] The compound represented by Formula 1 according to the present invention described above may be further embodied as a compound represented by any one of the compounds 1 to 210 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0305] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0306] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0307] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0308] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply attached (penant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0309] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0310] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0311] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0312] In the present invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0313] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0314] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0315] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0316] In the present invention, "condensed ring" refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0317]

[0318] Electron Transport Layer Material

[0319] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0320] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0321] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0322] Electron transport layer materials that can be mixed with the compound of Formula 1 above include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used individually or in combination of two or more types.

[0323] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0324]

[0325] Electron Transport Auxiliary Layer Material

[0326] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0327] The above electron transport auxiliary layer is positioned between the light-emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0328] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport materials known in the art. Preferably, it is used alone.

[0329] Electron transport materials that can be mixed with the compound of Chemical Formula 1 above include electron transport materials commonly known in the art. Examples may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0330] In the present invention, when the compound of Formula 1 and the electron transport material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0331]

[0332] Organic Electroluminescent Device

[0333] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0334] Specifically, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0335] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising 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 lifespan improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0336] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0337] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0338] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, the light-emitting layer, more preferably, the phosphorescent host may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0339] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0340] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more of the aforementioned organic layers include a compound represented by Chemical Formula 1.

[0341] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0342] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0343] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0344] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0345] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0346]

[0347] The present invention will be explained in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0348]

[0349] [Preparation Example 1-16]

[0350] [Preparation Example 1] Synthesis of (4'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid

[0351]

[0352] 50 g (320 mmol) of (3-chlorophenyl)boronic acid, 133.8 g (352 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 418.49 g (15.99 mmol) of Pd(PPh3), and 88.39 g (639.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 127.6 g (yield 87.4%) of compound SM1.

[0353] Mass : [(M+H) + ] : 456

[0354]

[0355] [Preparation Example 2] Synthesis of (4'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)boronic acid

[0356]

[0357] 50 g (320 mmol) of (4-chlorophenyl)boronic acid, 133.8 g (352 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 418.49 g (15.99 mmol) of Pd(PPh3), and 88.39 g (639.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 110.14 g (yield 75.5%) of compound SM2.

[0358] Mass : [(M+H) + ] : 456

[0359]

[0360] [Preparation Example 3] Synthesis of (2'-(triphenylsilyl)-[1,1'-biphenyl]-2-yl)boronic acid

[0361]

[0362] 50 g (320 mmol) of (2-chlorophenyl)boronic acid, 133.8 g (352 mmol) of (2-(triphenylsilyl)phenyl)boronic acid, 418.49 g (15.99 mmol) of Pd(PPh3), and 88.39 g (639.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 89.6 g (yield 61.4%) of compound SM3.

[0363] Mass : [(M+H) + ] : 456

[0364]

[0365] [Preparation Example 4] Synthesis of (3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid

[0366]

[0367] 50 g (320 mmol) of (3-chlorophenyl)boronic acid, 133.8 g (352 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 418.49 g (15.99 mmol) of Pd(PPh3), and 88.39 g (639.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 99.8 g (yield 68.4%) of compound SM4.

[0368] Mass : [(M+H) + ] : 456

[0369]

[0370] [Preparation Example 5] Synthesis of (4''-(triphenylsilyl)-[1,1':4',1''-terphenyl]-3-yl)boronic acid

[0371]

[0372] 50 g (215.1 mmol) of (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid, 90 g (236.6 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 412.4 g (10.75 mmol) of Pd(PPh3), and 59.5 g (430.2 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 89.8 g (yield 78.4%) of compound SM5.

[0373] Mass : [(M+H) + ] : 533

[0374]

[0375] [Preparation Example 6] Synthesis of (4''-(triphenylsilyl)-[1,1':3',1''-terphenyl]-4-yl)boronic acid

[0376]

[0377] 50 g (215.1 mmol) of (3'-chloro-[1,1'-biphenyl]-4-yl)boronic acid, 90 g (236.6 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 412.4 g (10.75 mmol) of Pd(PPh3), and 59.5 g (430.2 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 86.9 g (yield 75.9%) of compound SM6.

[0378] Mass : [(M+H) + ] : 533

[0379]

[0380] [Preparation Example 7] Synthesis of 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

[0381]

[0382] 50 g (184.8 mmol) of 2-bromo-4-chloro-6-phenyl-1,3,5-triazine, 77.3 g (203.3 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 410.7 g (9.24 mmol) of Pd(PPh3), and 51.1 g (369.7 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 75.3 g (yield 77.4%) of compound SM7.

[0383] Mass : [(M+H) + ] : 526

[0384]

[0385] [Preparation Example 8] Synthesis of 2-chloro-4-(9,9-dimethyl-9H-fluoren-1-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

[0386]

[0387] 50 g (129.3 mmol) of 2-bromo-4-chloro-6-(9,9-dimethyl-9H-fluoren-1-yl)-1,3,5-triazine, 54.1 g (142.2 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 47.48 g (6.47 mmol) of Pd(PPh3), and 35.7 g (258.6 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 69.85 g (yield 84.1%) of compound SM8.

[0388] Mass : [(M+H) + ] : 642

[0389]

[0390] [Preparation Example 9] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

[0391]

[0392] 50 g (144.3 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-bromo-6-chloro-1,3,5-triazine, 60.4 g (158.7 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 48.34 g (7.21 mmol) of Pd(PPh3), and 39.9 g (288.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 75.97 g (yield 87.5%) of compound SM9.

[0393] Mass : [(M+H) + ] : 602

[0394]

[0395] [Preparation Example 10] Synthesis of 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

[0396]

[0397] 50 g (144.3 mmol) of 2-([1,1'-biphenyl]-3-yl)-4-bromo-6-chloro-1,3,5-triazine, 60.4 g (158.7 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 48.34 g (7.21 mmol) of Pd(PPh3), and 39.9 g (288.5 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 64.8 g (yield 74.6%) of compound SM10.

[0398] Mass : [(M+H) + ] : 602

[0399]

[0400] [Preparation Example 11] Synthesis of 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole

[0401]

[0402] 50 g (139 mmol) of 9-(4-bromo-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole, 58.2 g (152.9 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 48.04 g (6.95 mmol) of Pd(PPh3), and 38.4 g (278.1 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 57.8 g (yield 67.6%) of compound SM11.

[0403] Mass : [(M+H) + ] : 615

[0404]

[0405] [Preparation Example 12] Synthesis of 2-chloro-4-phenyl-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine

[0406]

[0407] 50 g (184.8 mmol) of 2-bromo-4-chloro-6-phenyl-1,3,5-triazine, 77.3 g (203.3 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 410.7 g (9.24 mmol) of Pd(PPh3), and 51.1 g (369.7 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 76.7 g (yield 78.9%) of compound SM12.

[0408] Mass : [(M+H) + ] : 526

[0409]

[0410] [Preparation Example 13] Synthesis of 2-chloro-4-phenyl-6-(3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine

[0411]

[0412] 50 g (184.8 mmol) of 2-bromo-4-chloro-6-phenyl-1,3,5-triazine, 92.8 g (203.3 mmol) of compound SM4, 410.7 g (9.24 mmol) of Pd(PPh3), and 51.1 g (369.7 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 81.2 g (yield 72.9%) of compound SM13.

[0413] Mass : [(M+H) + ] : 602

[0414]

[0415] [Preparation Example 14] Synthesis of 4-chloro-2-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)pyrimidine

[0416]

[0417] 50 g (156.5 mmol) of 4-bromo-6-chloro-2-(naphthalen-2-yl)pyrimidine, 65.5 g (172.1 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 49.05 g (7.82 mmol) of Pd(PPh3), and 43.2 g (312.9 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 73.4 g (yield 81.6%) of compound SM14.

[0418] Mass : [(M+H) + ] : 575

[0419]

[0420] [Preparation Example 15] Synthesis of 2-chloro-4-phenyl-6-(4''-(triphenylsilyl)-[1,1':3',1''-terphenyl]-4-yl)-1,3,5-triazine

[0421]

[0422] 50 g (184.8 mmol) of 2-bromo-4-chloro-6-phenyl-1,3,5-triazine, 108.3 g (203.3 mmol) of compound SM 6, 410.7 g (9.24 mmol) of Pd(PPh3), and 51.1 g (369.7 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 89.4 g (yield 71.3%) of compound SM 15.

[0423] Mass : [(M+H) + ] : 678

[0424]

[0425] [Preparation Example 16] Synthesis of 4-chloro-2-phenyl-6-(3-(triphenylsilyl)phenyl)pyrimidine

[0426]

[0427] 50 g (185.5 mmol) of 4-bromo-6-chloro-2-phenylpyrimidine, 77.6 g (204.1 mmol) of (3-(triphenylsilyl)phenyl)boronic acid, 410.7 g (9.28 mmol) of Pd(PPh3), and 51.3 g (371.0 mmol) of K2CO3 were added to 500 ml of Tol, 125 ml of EtOH, and 125 ml of H2O, and heated and stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 70.57 g (yield 72.44%) of compound SM16.

[0428] Mass : [(M+H) + ] : 525

[0429]

[0430] [Synthesized Example 1-13]

[0431] [Synthesization Example 1] Synthesis of Compound 1

[0432]

[0433] 20 g (38.01 mmol) of compound SM 7, 15.9 g (41.82 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 42.20 g (1.90 mmol) of Pd(PPh3), and 10.51 g (76.03 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 28.4 g (yield 90.5%) of compound 1.

[0434] Mass : [(M+H) + ] : 826

[0435]

[0436] [Synthesization Example 2] Synthesis of Compound 7

[0437]

[0438] 20 g (31.14 mmol) of compound SM 8, 13.03 g (34.25 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 41.80 g (1.56 mmol) of Pd(PPh3), and 8.61 g (62.28 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 24.7 g (yield 84.1%) of compound 7.

[0439] Mass : [(M+H) + ] : 942

[0440]

[0441] [Synthesization Example 3] Synthesis of Compound 10

[0442]

[0443] 20 g (33.21 mmol) of compound SM 9, 13.9 g (36.53 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 41.92 g (1.66 mmol) of Pd(PPh3), and 9.18 g (66.42 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 26.1 g (yield 87.2%) of compound 10.

[0444] Mass : [(M+H) + ] : 902

[0445]

[0446] [Synthesization Example 4] Synthesis of Compound 13

[0447]

[0448] 20 g (33.21 mmol) of compound SM 10, 13.9 g (36.53 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 41.92 g (1.66 mmol) of Pd(PPh3), and 9.18 g (66.42 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 22.5 g (yield 75.2%) of compound 13.

[0449] Mass : [(M+H) + ] : 902

[0450]

[0451] [Synthesization Example 5] Synthesis of Compound 22

[0452]

[0453] 20 g (32.51 mmol) of compound SM 11, 13.6 g (35.76 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 41.88 g (1.63 mmol) of Pd(PPh3), and 8.99 g (65.02 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 24.2 g (yield 81.3%) of compound 22.

[0454] Mass : [(M+H) + ] : 915

[0455]

[0456] [Synthesization Example 6] Synthesis of Compound 26

[0457]

[0458] 20 g (38.01 mmol) of compound SM 12, 19.1 g (41.82 mmol) of compound SM 1, 42.20 g (1.90 mmol) of Pd(PPh3), and 10.5 g (76.03 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 26.9 g (yield 78.3%) of compound 26.

[0459] Mass : [(M+H) + ] : 902

[0460]

[0461] [Synthesization Example 7] Synthesis of Compound 36

[0462]

[0463] 20 g (38.01 mmol) of compound SM 7, 19.1 g (41.82 mmol) of compound SM 2, 42.20 g (1.90 mmol) of Pd(PPh3), and 10.5 g (76.03 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 28.7 g (yield 83.8%) of compound 36.

[0464] Mass : [(M+H) + ] : 902

[0465]

[0466] [Synthesization Example 8] Synthesis of Compound 64

[0467]

[0468] 20 g (33.21 mmol) of compound SM 13, 16.67 g (36.53 mmol) of compound SM 3, 41.92 g (1.66 mmol) of Pd(PPh3), and 9.18 g (66.42 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 21.6 g (yield 66.4%) of compound 64.

[0469] Mass : [(M+H) + ] : 978

[0470]

[0471] [Synthesization Example 9] Synthesis of Compound 105

[0472]

[0473] 20 g (32.51 mmol) of compound SM 11, 16.3 g (35.76 mmol) of compound SM 2, 41.88 g (1.63 mmol) of Pd(PPh3), and 8.99 g (65.02 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 26.2 g (yield 81.3%) of compound 105.

[0474] Mass : [(M+H) + ] : 991

[0475]

[0476] [Synthesization Example 10] Synthesis of Compound 113

[0477]

[0478] 20 g (32.51 mmol) of compound SM 11, 16.3 g (35.76 mmol) of compound SM 1, 41.88 g (1.63 mmol) of Pd(PPh3), and 8.99 g (65.02 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 24.9 g (yield 77.4%) of compound 113.

[0479] Mass : [(M+H) + ] : 991

[0480]

[0481] [Synthesization Example 11] Synthesis of Compound 121

[0482]

[0483] 20 g (38.1 mmol) of compound SM 16, 15.9 g (41.90 mmol) of (4-(triphenylsilyl)phenyl)boronic acid, 42.20 g (1.90 mmol) of Pd(PPh3), and 10.5 g (76.2 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 27.8 g (yield 88.5%) of compound 121.

[0484] Mass : [(M+H) + ] : 825

[0485]

[0486] [Synthesization Example 12] Synthesis of Compound 149

[0487]

[0488] 20 g (38.09 mmol) of compound SM 12, 19.1 g (41.9 mmol) of compound SM 4, 42.20 g (1.90 mmol) of Pd(PPh3), and 10.53 g (76.17 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 23.5 g (yield 68.4%) of compound 149.

[0489] Mass : [(M+H) + ] : 901

[0490]

[0491] [Synthesization Example 13] Synthesis of Compound 155

[0492]

[0493] 20 g (34.59 mmol) of compound SM 14, 17.4 g (38.05 mmol) of compound SM 4, 42.00 g (1.73 mmol) of Pd(PPh3), and 9.56 g (69.18 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 26.3 g (yield 79.8%) of compound 155.

[0494] Mass : [(M+H) + ] : 951

[0495]

[0496] [Synthesization Example 14] Synthesis of Compound 181

[0497]

[0498] 20 g (29.5 mmol) of compound SM 15, 17.3 g (32.4 mmol) of compound SM 5, 41.70 g (1.47 mmol) of Pd(PPh3), and 8.15 g (59.0 mmol) of K2CO3 were added to 200 ml of Tol, 50 ml of EtOH, and 50 ml of H2O and heated and stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with toluene, water was removed by adding MgSO4, and the mixture was filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure and purified by column chromatography using dichloromethane and hexane; the solid was then filtered and dried to obtain 21.7 g (yield 65.1%) of compound 181.

[0499] Mass : [(M+H) + ] : 1130

[0500]

[0501] [Example 1] Fabrication of a blue organic electroluminescent device (electron transport layer)

[0502] Compound 1 synthesized in the above synthesis example was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was fabricated according to the following process.

[0503] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0504] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / compound 1 (electron transport layer material) + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0505]

[0506] [Examples 2 to 14] Fabrication of Blue Organic Electroluminescent Devices

[0507] A blue organic electroluminescent device was fabricated by performing the same procedure as Example 1 above, except that each compound listed in Table 1 below was used instead of Compound 1 used as the electron transport layer material.

[0508]

[0509] [Comparative Examples 1 to 4] Preparation of Blue Organic Electroluminescent Devices

[0510] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that Alq3, BT-1, BT-2, and BT-3 were used instead of Compound 1 as the electron transport layer material.

[0511] The structures of HI, HAT-CN6, EB, BH, BD, Liq, Alq3, BT-1, BT-2, and BT-3 used in the above examples and comparative examples are as follows.

[0512]

[0513]

[0514] [Evaluation Example 1]

[0515] For the organic electroluminescent devices prepared in Examples 1 to 14 and Comparative Examples 1 to 4, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0516] Sample Electron Transport Layer Material Driving Voltage (V) Luminous Peak (nm) Current Efficiency (cd / A) Example 1 13.14548.0 Example 2 73.24557.6 Example 3 10 3.34557.9 Example 4 13 3.34547.8 Example 5 22 3.14558.0 Example 6 26 3.64557.7 Example 7 36 3.54547.8 Example 8 64 3.64557.8 Example 9 105 3.44557.9 Example 10 113 3.54548.1 Example 1 12 13.34557.7 Example 12 149 3.44547.7 Example 13 155 3.54567.9 Example 141813.74547.5 Comparative Example 1 Alq34.54555.8 Comparative Example 2 BT-14.34576.6 Comparative Example 3 BT-24.14567.0 Comparative Example 4 BT-33.94556.9

[0517] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 14, which used the compound according to the present invention as the electron transport layer material, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to Comparative Example 1, which used conventional Alq3 as the electron transport layer material; and Comparative Examples 2 to 4, which used compounds BT-1 to BT-3, which include an argin group and two arylsilyl groups, wherein the two arylsilyl groups are symmetrically bonded with respect to the argin group, as the electron transport layer material.

[0518]

[0519] [Examples 15 to 28] Fabrication of blue organic electroluminescent devices (electron transport auxiliary layer)

[0520] After purifying the compound synthesized in the above synthesis example to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was fabricated according to the following process.

[0521] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0522] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / electron transport auxiliary layer material of Table 2 below (5 nm) / ET + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0523] The structure of the compound ET used at this time is as follows.

[0524]

[0525]

[0526] [Comparative Example 5]

[0527] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 15 above, except that no electron transport auxiliary layer material was used and the thickness of the electron transport layer was changed to 35 nm.

[0528]

[0529] [Comparative Examples 6 to 8] Preparation of blue organic electroluminescent devices

[0530] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 15, except that BT-1, BT-2, and BT-3 were used instead of Compound 1 as the electron transport auxiliary layer material.

[0531] At this time, the structures of compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, BT-1, BT-2, and BT-3 used in Examples 15-28 and Comparative Examples 5-8 are the same as those in Example 1.

[0532]

[0533] [Evaluation Example 1]

[0534] For the organic electroluminescent devices prepared in Examples 15 to 28 and Comparative Examples 5 to 8, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0535] Sample Electron Transport Assisted Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 15 13.14548.0 Example 16 73.24558.0 Example 17 103.34548.2 Example 18 133.44547.8 Example 19 223.24558.0 Example 20 263.24558.0 Example 21 363.34558.1 Example 22 643.44557.9 Example 23 1053.24548.2 Example 24 1133.34548.3 Example 25 1213.24548.2 Example 26 1493.34557.9 Example 271553.54548.4 Example 281813.74557.9 Comparative Example 5-4.64565.7 Comparative Example 6BT-14.14566.8 Comparative Example 7BT-24.24556.7 Comparative Example 8BT-33.84557.2

[0536] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 15 to 28, which used the compound according to the present invention as the electron transport auxiliary layer material, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to Comparative Example 5, which did not include an electron transport auxiliary layer; and Comparative Examples 6 to 8, which used the compound BT-1 to BT-3, which included an argin group and two arylsilyl groups, wherein the two arylsilyl groups were symmetrically bonded with respect to the argin group, as the electron transport auxiliary layer material.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A plurality of Xs are identical or different from one another, and each is independently CR5 or N, provided that at least two of the plurality of Xs are N, Ar1 and R5 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, L1 and L2 are identical or different from each other, and each is independently a single bond, or C6~C 24 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 24 nuclei, m and n are each independently integers from 0 to 3, and R1 to R4, and R 11 to R 14 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, or can form a condensation ring by combining with any adjacent group; a to c, e to g are each independently integers from 0 to 5, and d and h are each independently integers from 0 to 4, and The arylene group and heteroarylene group of L1 to L2 above; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group of Ar1 and R5 above; The above R1~R 4, R 11 ~R 14 The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, heteroarylamine group, and condensation ring are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, wherein if there are multiple substituents, they may be identical or different from each other. However, the compound represented by the above chemical formula 1 has an asymmetric structure based on the X-containing ring.

2. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound that satisfies at least one of the following conditions (i) to (iv): (i) the above R1~R4 containing silane groups and the above R 11 ~R 14 The contained silane group is asymmetrically bonded with respect to the X-containing ring; (ii) the above R1~R4 containing silane groups and the above R 11 ~R 14 The contained silane groups are asymmetrically bonded with respect to L1 and L2; (iii) L1 and L2 are different; (iv) n and m are different.

3. In Paragraph 1, The above X-containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates the part connected to the above chemical formula 1, and Ar1 is as defined in Paragraph 1.

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

5. In Paragraph 1, Ar1 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 21 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

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

7. In Paragraph 1, R1 to R4, and R 11 to R 14 are identical or different from each other, and each independently hydrogen, deuterium (D), cyano group, halogen, C1~C 40 alkyl group of, C3~C 40 cycloalkyl group of, C6~C 60 A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

8. In Paragraph 1, The compound represented by the above Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2 to 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above formula, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1.

9. In Paragraph 1, The silane groups containing R1 to R4 of the above chemical formula 1 and R 11 ~R 14 A compound in which the contained silane groups are asymmetrically bonded to each other based on the X-containing ring.

10. In Paragraph 9, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 6 to 11: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] In the above formula, X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1.

11. In Paragraph 9, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 12 to 15: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] In the above formula, X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m and n are each as defined in paragraph 1, provided that cases where m and n are each 0 are excluded.

12. In Paragraph 9, The compound represented by the above Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 16 to 24: [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] In the above formula, X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and Y1 and Y2 are identical or different from each other, and each independently O, S, NR 31 , and CR 32 R 33 It is selected from a group consisting of, R 31 to R 33 They are identical or different from each other, and each independently hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, Rings A1 and A2 are identical or different from each other and are each independently condensed polycyclic aromatic rings having 8 to 18 carbon atoms.

13. In Paragraph 9, The compound represented by the above Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 25 to 29: [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] In the above formula, X, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, h, m, and n are each as defined in Chemical Formula 1, and Ring B is a condensed polycyclic aromatic ring having 8 to 18 carbon atoms, and Ring C is a cycloalkyl group or an adamantane group having 3 to 12 carbon atoms, and Z1 is O, S, NR 41 , and CR 42 R 43 It is selected from a group composed of, Z2 is N, and R 41 to R 43 Each independently consists of hydrogen, deuterium, and C1~C 20 alkyl group of, C6~C 20 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 20 nuclei, o is an integer from 1 to 3.

14. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 40 to 45: [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] In the above formula, X, Ar1, L1~L2, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Paragraph 1, and m and n are integers from 1 to 3, respectively, provided that m and n are different from each other in chemical formulas 43 to 45.

15. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 46 to 48: [Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] In the above formula, X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Paragraph 1, and m and n are integers from 1 to 3, respectively, and The above and Each is independently selected from the following structural formulas, but is distinct from one another, and In the above formula, * indicates a region connected to the above chemical formulas 46 to 48.

16. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 49 to 51: [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 51] In the above formula, X, Ar1, R 1~ R4, R 11 ~R 14 , a, b, c, d, e, f, g, and h are each as defined in Paragraph 1, and L1 and L2 are each independently single bonds, or are selected from the following structural formulas, but are different from each other, In the above formula, * indicates a region connected to the above chemical formulas 49 to 51.

17. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 210.

18. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound that is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

19. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound described in any one of claims 1 to 18.

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

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