Organic light-emitting compound and organic electroluminescent device using same

Abstract

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

Description

Organic luminescent compounds and organic electroluminescent devices using the same

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

[0002]

[0003] Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices led to the blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic electroluminescent device with a layered structure divided into functional layers, a hole layer and an emission layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has been made by introducing characteristic organic layers within the device, which has led to the development of specialized materials used for this.

[0004] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified according to their function, such as luminescent materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0005] The light-emitting layer materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials according to the emission color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. In addition, a host / dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. The 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. The development of such phosphorescent materials is focusing on not only phosphorescent dopants but also phosphorescent host materials because it can theoretically improve luminous efficiency by up to four times compared to fluorescence. Currently, NPB, BCP, Alq3, etc. are widely known as materials used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as luminescent materials. Among the phosphorescent materials, Ir-containing metal complex compounds, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are used as blue, green, and red dopant materials, especially those with significant advantages in terms of efficiency enhancement among luminescent materials. To date, CBP has demonstrated excellent properties as a phosphorescent host material.

[0006] However, while conventional luminescent materials offer advantages in terms of luminescence properties, their low glass transition temperatures and poor thermal stability make them unsatisfactory in terms of lifespan in organic electroluminescent devices. Therefore, the development of luminescent materials with superior performance is urgently needed.

[0007]

[0008] The present invention has been devised to solve the above-mentioned problems, and more specifically, it is a technical task to provide a novel compound having excellent heat resistance, carrier transport ability, etc., which can be used as an organic layer material of an organic electroluminescent device, specifically, a light-emitting layer material, a life-span improving layer material, a light-emitting auxiliary layer material, an electron transport layer material, and / or an electron transport auxiliary layer material.

[0009] In addition, another technical task of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan, including the novel compound.

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

[0011]

[0012] To achieve the above purpose, 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] R1 to R3 are the same or different and each independently represent 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups, provided that at least one of R1 to R3 is a moiety represented by the following chemical formula 1A,

[0017] a and b are each independently an integer from 0 to 3, c is an integer from 0 to 2,

[0018] [Chemical Formula 1A]

[0019]

[0020] In the above chemical formula 1A,

[0021] X1 to X 10 are identical or different from each other, and each is independently N or C(R4), and only X1 to X 10 At least one of them is N,

[0022] R4 is 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups, and when there are multiple R4s, the multiple R4s are the same or different from each other,

[0023] L1 and L2 are the same or different, and each independently represents a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0024] m and n are each independently integers from 0 to 3,

[0025] Ar1 is hydrogen, deuterium, halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the arylamine group of,

[0026] The arylene group and heteroarylene group of the above L1 to L2, and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above Ar1, R1 to R4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0027] 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.

[0028] Here, the organic layer including the compound represented by the 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 life-span improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by the 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.

[0029]

[0030] As one embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0031] In particular, when the compound represented by the chemical formula 1 of the present invention is used as a phosphorescent host, charge generation layer (CGL), electron transport layer, or 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 host materials or electron transport materials.

[0032] Accordingly, the organic electroluminescent device including the compound of the above chemical formula 1 can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0033] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0034]

[0035] Hereinafter, the present invention will be described in detail.

[0036] <New organic compounds>

[0037] The present invention provides a novel compound having excellent thermal stability, carrier transport ability, and luminescence ability.

[0038] According to the present invention, a compound represented by chemical formula 1 is structurally characterized by including a fluorene moiety (Core) and a phenanthroline moiety having at least one nitrogen-containing heterocycle introduced at the 9th carbon position, and forming a basic skeleton in which these are directly bonded or connected through at least one linker (e.g., L1 to L2).

[0039] Specifically, the compound represented by the above chemical formula 1 has a higher glass transition temperature (Tg) than a conventional fluorene compound in which a hydrogen or methyl group is introduced at the 9th carbon position by including a fluorene moiety in which at least one nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position, and thus can exhibit superior performance in terms of durability and lifespan characteristics of the device, and also exhibits superior performance in terms of electron transport ability than a conventional fluorene compound in which two phenyl groups are introduced at the 9th carbon position.

[0040] In addition, since the phenanthroline moiety can form a gap state by binding with a metal such as an alkali metal or alkaline earth metal (e.g., Li, Yb, etc.), which is a dopant of an N-type charge generation layer, the electron transfer characteristics to the electron transport layer can be improved when applied as an N-type charge generation layer (CGL) material, and at the same time, since it has strong electron withdrawing group (EWG) characteristics, it can be used as an electron transport layer material of an organic electroluminescent device. Accordingly, when the compound of Chemical Formula 1, in which a fluorene moiety having a nitrogen-containing heteroaromatic ring introduced therein and a phenanthroline moiety are bonded, is used as at least one of an electron transport layer material and an N-type charge generation layer material of an organic electroluminescent device, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, and long lifespan characteristics compared to the prior art can be manufactured, and further, a full-color display panel having improved performance, durability, and lifespan can also be manufactured.

[0041] Furthermore, since the compound of the above chemical formula 1 has a higher triplet energy than the light-emitting layer, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Accordingly, the number of excitons contributing to light emission increases, so that the light-emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan characteristics of the device can be efficiently increased. In addition, the excellent electron transport ability of the compound represented by the above chemical formula 1 can have high efficiency and fast mobility in an organic electroluminescent device, and it is easy to control the HOMO and LUMO energy levels depending on the direction or position of the substituent.

[0042] As described above, when the compound represented by the chemical formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably an emitting layer material (a blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, or a life-span improvement layer material, the performance and life-span characteristics of the organic electroluminescent device can be significantly improved. In particular, when the compound of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect in terms of the efficiency, driving voltage, and life-span characteristics of the device can be expected. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0043] According to the present invention, the compound represented by chemical formula 1 is a fluorene moiety core (Core, X1~X) in which at least one nitrogen-containing heterocycle is introduced at the 9th carbon position. 10 It includes a phenanthroline moiety (R1~R3 ​​containing ring) and a phenanthroline moiety (R1~R3 ​​containing ring), and these are directly bonded or bonded through at least one linker (e.g., L1~L2) to form a basic skeleton.

[0044] In the compound represented by the above chemical formula 1, the phenanthroline moiety (R1-R3 containing ring) is a phenanthrene containing two nitrogen atoms. Since this phenanthroline moiety is a strong electron withdrawing group (EWG), it exhibits excellent electron transport ability, and furthermore, it has binding properties with metals due to the electron-rich nitrogen and aromatic ring. Accordingly, it can be combined with a metal such as an alkali metal or alkaline earth metal (e.g., Li, Yb, etc.), which is a dopant of a charge generation layer (CGL), especially an N-type charge generation layer, to enhance the electron transport properties as an electron transport layer material.

[0045] In the phenanthroline moiety, R1 to R3 can be substituted with various substituents. R1 to R3 are the same or different, and each independently represent 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60is selected from the group consisting of arylamine groups, and at least one of R1 to R3 has a moiety represented by the following chemical formula 1A. Specifically, R1 to R3 are the same or different from each other, and each independently represent hydrogen, deuterium (D), halogen, cyano group, C1~C 40 Alkyl group of C1~C 40 Alkylphosphine oxide group, C6~C 60 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0046] Here, a and b are each independently an integer from 0 to 3, and c is an integer from 0 to 2. When a is 0, R1 is hydrogen, and when a is 1 to 3, R1 may have the aforementioned substituents other than hydrogen. The same may be applied to b and c.

[0047] For example, R1 to R3 may be the same or different from each other, and may each be independently selected from the following structural formulas, but are not limited thereto.

[0048]

[0049] In the above formula,

[0050] * indicates a part connected to the above chemical formula 1,

[0051] R5 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is selected from the group consisting of an aryl group of , and a heteroaryl group having 5 to 18 nuclear atoms. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definitions of R1 to R3) may be substituted.

[0052] In the compound represented by chemical formula 1 according to the present invention, at least one of R1 to R3 of the phenanthroline moiety has a fluorene-based moiety represented by chemical formula 1A below.

[0053] The moiety of this formula 1A is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen, for example, a fluorene-based moiety (Core, X1~X) in which a nitrogen-containing heteroaromatic ring is substituted at the 9th carbon position. 10 (containing ring). The above nitrogen-containing heterocycle (e.g., X1~X) 10 As an example of a compound containing X1 to X 10 are identical or different from each other, and each is independently N or C(R4), and only X1 to X 10 At least one of them is N. By including a heteroaromatic ring containing at least one nitrogen, it exhibits better electron absorption properties, which is advantageous for electron injection and transport.

[0054] Here, R4 is 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups, and when R4 is plural, the plurality of R4 are the same or different from each other.

[0055] For example, the nitrogen-containing heteroaromatic ring, for example, a ring moiety containing X1 to X5, and X6 to X 10 The ring moieties contained therein may be identical or different, and each may be any one selected from the following structural formulas, but are not limited thereto.

[0056]

[0057] In the above formula,

[0058] * indicates a part connected to the above chemical formula 1A,

[0059] A plurality of R4s are the same or different, and are each independently selected from the group consisting of hydrogen, an alkyl group, an aryl group, and a heteroaryl group.

[0060] A preferred specific example is the fluorene moiety (e.g., X1 to X 10 The containing ring) may be any one selected from the following structural formulas, but is not limited thereto.

[0061]

[0062]

[0063] In the above formula,

[0064] * indicates a part connected to the above chemical formula 1,

[0065] Ar1, L1, L2, m and n are each as defined in Chemical Formula 1. In addition, although not specifically indicated, at least one substituent known in the art (e.g., the same as the R1 to R3 definitions) may be substituted, although not indicated in the structural formula described above.

[0066] In the above fluorene moiety, Ar1 can be substituted with various substituents. Such Ar1 can be hydrogen, deuterium, halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 can be selected from the arylamine group of. Specifically, Ar1 is hydrogen, deuterium (D), halogen, cyano group, C1~C 40 Alkyl group of C1~C 40 Alkylphosphine oxide group, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, and may be the same as the specific examples of R1 to R3 described above.

[0067] In the compound represented by the chemical formula 1 according to the present invention, a fluorene moiety core (Core, X1~X) into which a nitrogen-containing heteroaromatic ring containing at least one nitrogen is introduced 10 The phenanthroline moiety (R1-R3 containing ring) and the fluorene core and Ar1 can be directly bonded or connected via a separate linker (e.g., L1-L2). When a linker is present in this way, the HOMO region is expanded, which benefits the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate HOMO-LUMO overlap. In addition, the stability of the molecule can be increased.

[0068] The linker (e.g., L1~L2) is not particularly limited and may be a linker of a common divalent group known in the art. Specifically, L1 and L2 are the same or different from each other, and each independently represents a single bond, or C6~C 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. More specifically, L1 and L2 are each independently C6~C 12 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 12 nuclear atoms. Here, the number of linkers (m, n) is an integer from 0 to 3. Here, when m is 0, L1 corresponds to a single bond, and when m is 1 to 3, L1 may have the above-mentioned substituents except for the single bond. The same can be applied to n. At this time, a plurality of L1 and L2 may be the same or different from each other.

[0069] Specific examples of the above arylene linker include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, an indoylene group, a purinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolilene group, a thiazolilene group, a pyridinylene group, a pyrimidinylene group, etc. More specifically, a phenylene group or a biphenylene group is preferable. In addition, specific examples of heteroarylene linkers include a pyrrole moiety, a furan moiety, a thiophene moiety, a pyridine moiety, a pyrimidine moiety, a pyrazine moiety, a triazine moiety, a dibenzofuran moiety, a dibenzothiophene moiety, and / or a dibenzoselenophenone moiety.

[0070] For example, L1 and L2 may be the same or different from each other, and may each independently be a single bond or a linking group selected from the following structural formulas.

[0071]

[0072] In the above formula,

[0073] * indicates a part connected to the above chemical formula 1,

[0074] R6 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definition of R1 to R3) may be substituted.

[0075] In the above-described chemical formula 1, the arylene group and heteroarylene group of L1 to L2, and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of Ar1, R1 to R4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0076] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as the following chemical formula 2 or chemical formula 3 depending on the binding position of phenanthroline. However, the present invention is not limited thereto.

[0077] [Chemical Formula 2]

[0078]

[0079] [Chemical Formula 3]

[0080]

[0081] For example, the compound represented by the above chemical formula 2 can be further specified by any one of the following chemical formulas 2A to 2C, and the compound represented by the above chemical formula 3 can be further specified by the following chemical formula 3A.

[0082] [Chemical Formula 2A]

[0083]

[0084] [Chemical Formula 2B]

[0085]

[0086] [Chemical Formula 2C]

[0087]

[0088] [Chemical Formula 3A]

[0089]

[0090] X1~X 10 , Ar1, R1~R3, L1~L2, m, and n are each as defined in chemical formula 1.

[0091] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 comprises a fluorene moiety (e.g., X1 to X) in which at least one nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position. 10 Depending on the bonding position between the ring containing the phenanthroline / linker (e.g., L1), it can be further specified as one of the following chemical formulae 4 to 7. However, it is not limited thereto.

[0092] [Chemical Formula 4]

[0093]

[0094] [Chemical Formula 5]

[0095]

[0096] [Chemical Formula 6]

[0097]

[0098] [Chemical Formula 7]

[0099]

[0100] In the above chemical formulas 4 to 7,

[0101] X1~X 10 , Ar1, R1~R3, L1~L2, m, and n are each as defined in Article 1.

[0102] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 comprises a fluorene moiety (e.g., X1 to X) in which at least one nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position. 10 Depending on the bonding position between the ring containing the compound and Ar1 / linker (e.g., L2), it can be further specified as one of the following chemical formulas 8 to 11. However, it is not limited thereto.

[0103] [Chemical Formula 8]

[0104]

[0105] [Chemical Formula 9]

[0106]

[0107] [Chemical Formula 10]

[0108]

[0109] [Chemical Formula 11]

[0110]

[0111] In the above chemical formulas 8 to 11,

[0112] X1~X 10 , Ar1, R1~R3, L1~L2, m, and n are each as defined in chemical formula 1.

[0113] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 12 to 21, depending on the bonding position of the substituents (e.g., R1 to R3) introduced to phenanthroline. However, the present invention is not limited thereto.

[0114] [Chemical Formula 12]

[0115]

[0116] [Chemical Formula 13]

[0117]

[0118] [Chemical Formula 14]

[0119]

[0120] [Chemical Formula 15]

[0121]

[0122] [Chemical Formula 16]

[0123]

[0124] [Chemical Formula 17]

[0125]

[0126] [Chemical Formula 18]

[0127]

[0128] [Chemical Formula 19]

[0129]

[0130] [Chemical Formula 20]

[0131]

[0132] [Chemical Formula 21]

[0133]

[0134] In the above chemical formulas 12 to 21,

[0135] X1~X 10 , Ar1, R1~R3, L1~L2, m, and n are each as defined in chemical formula 1.

[0136] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 22 to 25, depending on the type of substituent (e.g., R1 to R3) introduced into phenanthroline. However, the present invention is not limited thereto.

[0137] [Chemical Formula 22]

[0138]

[0139] [Chemical Formula 23]

[0140]

[0141] [Chemical Formula 24]

[0142]

[0143] [Chemical Formula 25]

[0144]

[0145] In the above chemical formulas 22 to 25,

[0146] Z1 to Z3 are the same or different from each other, and each independently represents N or C(R 11), and at least one of Z1 to Z3 is N. Specifically, it includes 1 to 3 Ns, and more specifically, it may include 2 to 3 Ns. In this way, when a heterocycle containing 2 to 3 nitrogens is included, the excellent electron absorption properties can be further increased.

[0147] R 11 Each independently represents 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring, and the R 11 In this case, multiple R 11 are identical or different from each other. Specifically, R 11 are each independently hydrogen, deuterium, C1~C 40 Alkyl group of C6~C 60 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0148] Ar2 and Ar3 are the same or different from each other, and are each independently hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, specifically C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0149] Y is O or S,

[0150] Ring A is an aromatic condensed polycyclic group having 10 to 30 carbon atoms, which is a common divalent group known in the art, and can be specifically selected from a naphthalene group, a phenalene group, an anthracene group, a fluoranthene group, a triphenylene group, a phenanthrene group, a pyrene group, a chrysene group, and a perylene group.

[0151] o is an integer from 1 to 3,

[0152] X1~X 10 , Ar1, R1, R3, L1~L2, m, and n are each as defined in chemical formula 1.

[0153] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 comprises a fluorene moiety (e.g., X1 to X) bonded to a nitrogen-containing heterocycle at the 9th carbon position. 10 Depending on the type of substituent (e.g., Ar1) substituted in the ring containing the compound, it can be further specified as one of the following chemical formulas 26 to 29. However, it is not limited thereto.

[0154] [Chemical Formula 26]

[0155]

[0156] [Chemical Formula 27]

[0157]

[0158] [Chemical Formula 28]

[0159]

[0160] [Chemical Formula 29]

[0161]

[0162] In the above chemical formulas 26 to 29,

[0163] Z1 to Z3 are the same or different from each other, and each independently represents N or C(R 11 ), and at least one of Z1 to Z3 is N. Specifically, it includes 1 to 3 Ns, and more specifically, it may include 2 to 3 Ns. In this way, when a heterocycle containing 2 to 3 nitrogens is included, the excellent electron absorption properties can be further increased.

[0164] R 11 Each independently represents 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C1~C 40 Alkylphosphine group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group, and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring, and the R 11 In this case, multiple R 11are identical or different from each other. Specifically, R 11 are each independently hydrogen, deuterium, C1~C 40 Alkyl group of C6~C 60 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0165] Ar2 and Ar3 are the same or different from each other, and are each independently hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 aryl group, and heteroaryl having 5 to 60 nuclear atoms, specifically C6~C 60 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0166] Y is O or S,

[0167] Ring A is an aromatic condensed polycyclic group having 10 to 30 carbon atoms of a common divalent group known in the art, and may be specifically selected from a naphthalene group, a phenalene group, an anthracene group, a fluoranthene group, a triphenylene group, a phenanthrene group, a pyrene group, a chrysene group, and a perylene group.

[0168] o is an integer from 1 to 3,

[0169] X1~X 10 , R1~R3, L1~L2, m, and n are each as defined in chemical formula 1.

[0170] The compound represented by the chemical formula 1 of the present invention described above can be further specified as the compounds exemplified below, for example, compounds represented by 1 to 324. However, the compound represented by the chemical formula 1 of the present invention is not limited to those exemplified below.

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched 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.

[0185] In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0186] In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0187] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0188] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form 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.

[0189] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0190] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl 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, and pentoxy.

[0191] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms.

[0192] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0193] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom in the ring, preferably 1 to 3 carbon atom(s), is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0194] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 40 carbon atoms.

[0195] In the present invention, “fused ring” means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0196]

[0197] Electron transport layer material

[0198] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0199] The above electron transport layer (ETL) plays a role in moving electrons injected from the cathode to an adjacent layer, specifically, the light-emitting layer.

[0200] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

[0201] The electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of electron transport materials that can be used include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3(tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.

[0202] In the present invention, when the compound of the above chemical formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately controlled within a range known in the art.

[0203]

[0204] <Electron transport auxiliary layer material>

[0205] In addition, the present invention provides an electron transport auxiliary layer comprising a compound represented by the above chemical formula 1.

[0206] 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.

[0207] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport auxiliary layer material known in the art. It is preferably used alone.

[0208] The electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer material may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a nitrogen-containing heterocyclic derivative, and the like.

[0209] In the present invention, when the compound of the above chemical formula 1 and the electron transport auxiliary layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0210]

[0211] Electron injection layer material

[0212] The present invention provides an electron injection layer comprising a compound represented by the above chemical formula 1.

[0213] The compound represented by the above chemical formula 1 can be used alone as an electron injection layer (EIL) material, or can be mixed with an electron injection layer material known in the art.

[0214] The electron injection layer material that can be mixed with the compound of the above chemical formula 1 is not particularly limited as long as it is a material that easily injects electrons and has high electron mobility, and any electron injection layer material commonly used in the art can be used without limitation. In this case, the materials forming the electron transport layer and the electron injection layer may be the same or different from each other.

[0215] Non-limiting examples of usable electron-injecting materials include anthracene derivatives, heteroaromatic compounds, alkali metal complexes, etc. Specifically, there are LiF, Li2O, BaO, NaCl, CsF; lanthanide metals such as Yb; or halogenated metals such as RbCl, RbI, etc., which may be used alone or in combination of two or more.

[0216] In the present invention, when the compound of the above chemical formula 1 and the electron injection layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately controlled within a range known in the art.

[0217] The electron injection layer and electron transport layer according to the present invention may each be co-deposited with an n-type dopant to facilitate electron injection from the cathode. In this case, the n-type dopant may be any alkali metal complex known in the art without limitation, and examples thereof include alkali metals, alkaline earth metals, or rare earth metals.

[0218]

[0219] Charge generation layer

[0220] In addition, the present invention provides a charge generation layer, more specifically, an N-type charge generation layer, comprising a compound represented by the chemical formula 1.

[0221] A charge generation layer (CGL) is a layer that separates adjacent light-emitting stacks without directly contacting the two electrodes (e.g., anode and cathode) in an organic light-emitting device having multiple light-emitting stacks. The CGL is positioned between two adjacent light-emitting stacks, and acts as a cathode by generating electrons for one light-emitting stack, and acts as an anode by generating holes for the other light-emitting stack.

[0222] The compound represented by the above chemical formula 1 can be used alone as a charge generation layer material, more specifically, as an N-type charge generation layer material, or can be used in combination with charge generation layer materials known in the art. It is preferably used alone.

[0223] The charge generation layer material used in combination with the compound according to the present invention may be any material that can be used as a charge generation layer (CGL) material without limitation. In addition, the material for the charge generation layer may be formed by doping with a conventional n-type material and / or p-type material known in the art.

[0224] When the compound of the above chemical formula 1 and a conventional charge generation layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0225]

[0226] Organic electroluminescent devices

[0227] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by the chemical formula 1 according to the present invention.

[0228] Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compound may be used alone or in a mixture of two or more.

[0229] The organic layer of one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a charge generation layer, and / or a life-span improvement layer, and more specifically, it is preferably an electron transport layer, an electron transport auxiliary layer, an electron injection layer, and an n-type charge generation layer.

[0230] The light-emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and may include the compound of the above chemical formula 1 as the host material. In addition, the light-emitting layer of the present invention may include a known compound in the art other than the compound of the above chemical formula 1 as the host.

[0231] When the compound represented by the above chemical formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound represented by the above chemical formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light-emitting layer having high efficiency.

[0232] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially laminated. At this time, at least one of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by the chemical formula 1, and preferably, at least one of the electron transport layer, the electron transport auxiliary layer, and / or the electron injection layer may include a compound represented by the chemical formula 1. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.

[0233] 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.

[0234] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers described above includes a compound represented by the chemical formula 1.

[0235] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0236] The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, etc. can be used.

[0237] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0238] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0239] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

[0240] In another embodiment of the present invention, the organic electroluminescent device may have a plurality of light-emitting stacks including at least one light-emitting layer.

[0241] The plurality of light-emitting layers included in the light-emitting stack may be light-emitting layers that each emit light of a different color, or light-emitting layers that emit light of the same color. That is, the light-emitting color may vary depending on the material that constitutes the light-emitting layer. For example, the plurality of light-emitting stacks may include materials that emit light of blue, green, red, yellow, white, etc., and may be formed using a phosphorescent or fluorescent material. In this case, the colors exhibited by each light-emitting layer may be complementary to each other. In addition, the color may be selected as a combination of colors that can emit white light. Each of the light-emitting layers may include phosphorescent dopants or fluorescent dopants corresponding to the selected color, respectively.

[0242] More specifically, the organic electroluminescent device further comprises a plurality of light-emitting layer stacks including at least one light-emitting layer; and a charge generation layer (CGL) disposed between adjacent stacks of the plurality of light-emitting layer stacks, wherein the charge generation layer may be an N-type charge generation layer including the compound.

[0243] Such a charge generation layer may further include a material that can be used as a charge generation layer (CGL) material known in the art. In addition, a material for use as a charge generation layer may be formed by doping with a conventional n-type material and / or p-type material known in the art.

[0244] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0245]

[0246] [Preparation Example 1] Synthesis of 2-chloro-9-phenyl-1,10-phenanthroline (A01)

[0247]

[0248] Bromobenzene (21.9 g, 139.8 mmol) was dissolved in 450 mL of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (67.1 mL of 2.5 M in hexane, 167.7 mmol) was slowly added dropwise. After stirring at -78°C for 1 hour, 2-chloro-1,10-phenanthroline (30.0 g, 139.8 mmol) was added, reacted for 3 hours, and quenched with NH4Cl solution at room temperature. The mixture was extracted with methylene chloride and washed with brine. The washed organic layer was concentrated, dissolved in 450 mL of methylene chloride, MnO2 (48.6 g, 559.0 mmol) was added, and heated and refluxed for 12 hours. After the reaction was completed, the MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and then crystallized with acetone and MeOH to obtain 2-chloro-9-phenyl-1,10-phenanthroline (37.0 g, 127.2 mmol, yield 91%).

[0249] Mass: [(M+H)+]: 292

[0250]

[0251] [Preparation Example 2] Synthesis of 2-chloro-9-(naphthalen-2-yl)-1,10-phenanthroline (A02)

[0252]

[0253] 2-Bromonaphthalene (28.9 g, 139.8 mmol) was dissolved in 450 mL of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (67.1 mL of 2.5 M in hexane, 167.7 mmol) was slowly added dropwise. The mixture was stirred for 1 hour at -78°C, 2-chloro-1,10-phenanthroline (30.0 g, 139.8 mmol) was added, and the reaction was allowed to proceed for 3 hours. The reaction was then quenched with NH4Cl solution at room temperature. The mixture was extracted with methylene chloride and washed with brine. The washed organic layer was concentrated, dissolved in 450 mL of methylene chloride, and MnO2 (48.6 g, 559.0 mmol) was added. The mixture was heated and refluxed for 12 hours. After the reaction was completed, the MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and then crystallized with acetone and MeOH to obtain 2-chloro-9-(naphthalen-2-yl)-1,10-phenanthroline (42.9 g, 125.8 mmol, yield 90%).

[0254] Mass: [(M+H)+]: 342

[0255]

[0256] [Preparation Example 3] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-chloro-1,10-phenanthroline (A03)

[0257]

[0258] 3-Bromo-1,1'-biphenyl (32.6 g, 139.8 mmol) was dissolved in 450 mL of anhydrous THF, cooled to -78°C under a nitrogen atmosphere, and n-BuLi (67.1 mL of 2.5 M in hexane, 167.7 mmol) was slowly added dropwise. The mixture was stirred for 1 hour at -78°C, 2-chloro-1,10-phenanthroline (30.0 g, 139.8 mmol) was added, and the reaction was allowed to proceed for 3 hours. The reaction was terminated with NH4Cl solution at room temperature. The mixture was extracted with methylene chloride and washed with brine. After concentrating the washed organic layer, it was dissolved in 450 ml of methylene chloride, and MnO2 (48.6 g, 559.0 mmol) was added, followed by heating and reflux stirring for 12 hours. When the reaction was complete, the MnO2 was removed by filtration, washed with water, and the organic layer was concentrated and then crystallized with acetone and MeOH to obtain 2-([1,1'-biphenyl]-3-yl)-9-chloro-1,10-phenanthroline (45.6 g, 368 mmol, yield 89%).

[0259] Mass: [(M+H)+]: 368

[0260]

[0261] [Preparation Example 4] Synthesis of 2-(3-chlorophenyl)-9-phenyl-1,10-phenanthroline (A04)

[0262]

[0263] A01 (30.0 g, 103.2 mmol) synthesized by the method of Preparation Example 1 and (3-chlorophenyl)boronic acid (16.1 g, 103.2 mmol), Pd(PPh3)4 (3.6 g, 3.1 mmol), K2CO3 (42.8 g, 309.5 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-9-phenyl-1,10-phenanthroline (28.8 g, 78.4 mmol, yield 76%).

[0264] Mass: [(M+H)+]: 368

[0265]

[0266] [Preparation Example 5] Synthesis of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline (A05)

[0267]

[0268] A01 (30.0 g, 103.2 mmol) synthesized by the method of Preparation Example 1 and (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (24.0 g, 103.2 mmol), Pd(PPh3)4 (3.6 g, 3.1 mmol), K2CO3 (42.8 g, 309.5 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline (36.6 g, 82.5 mmol, yield 80%).

[0269] Mass: [(M+H)+]: 444

[0270]

[0271] [Preparation Example 6] Synthesis of 2-(3-chlorophenyl)-9-(naphthalen-2-yl)-1,10-phenanthroline (A06)

[0272]

[0273] A02 (30.0 g, 88.0 mmol) synthesized by the method of Preparation Example 2 and (3-chlorophenyl) boronic acid (13.8 g, 88.0 mmol), Pd(PPh3)4 (3.1 g, 2.6 mmol), K2CO3 (36.5 g, 264.1 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-9-(naphthalen-2-yl)-1,10-phenanthroline (29.7 g, 71.3 mmol, yield 81%).

[0274] Mass: [(M+H)+]: 418

[0275]

[0276] [Preparation Example 7] Synthesis of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (A07)

[0277]

[0278] A02 (30.0 g, 88.0 mmol) synthesized by the method of Preparation Example 2 and (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (20.5 g, 88.0 mmol), Pd(PPh3)4 (3.1 g, 2.6 mmol), and K2CO3 (36.5 g, 264.1 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (36.9 g, 74.8 mmol, yield 85%).

[0279] Mass: [(M+H)+]: 494

[0280]

[0281] [Preparation Example 8] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(3-chlorophenyl)-1,10-phenanthroline (A08)

[0282]

[0283] A03 (30.0 g, 81.8 mmol) synthesized by the method of Preparation Example 3 and (3-chlorophenyl)boronic acid (12.8 g, 81.8 mmol), Pd(PPh3)4 (2.8 g, 2.5 mmol), K2CO3 (33.9 g, 245.3 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-9-(3-chlorophenyl)-1,10-phenanthroline (27.5 g, 62.2 mmol, yield 76%).

[0284] Mass: [(M+H)+]: 444

[0285]

[0286] [Preparation Example 9] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(3'-chloro-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline ( A09 )

[0287]

[0288] A03 (30.0 g, 81.8 mmol) synthesized by the method of Preparation Example 3 and (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (19.0 g, 81.8 mmol), Pd(PPh3)4 (2.8 g, 2.5 mmol), and K2CO3 (33.9 g, 245.3 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-9-(3'-chloro-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (33.5 g, 64.6 mmol, yield 79%).

[0289] Mass: [(M+H)+]: 520

[0290]

[0291] [Preparation Example 10] Synthesis of 2-(3-chlorophenyl)-1,10-phenanthroline (A10)

[0292]

[0293] 2-chloro-1,10-phenanthroline (30.0 g, 139.8 mmol), (3-chlorophenyl) boronic acid (21.9 g, 139.8 mmol), Pd(PPh3)4 (4.8 g, 4.2 mmol), K2CO3 (57.9 g, 419.3 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3-chlorophenyl)-1,10-phenanthroline (32.1 g, 110.4 mmol, yield 79%).

[0294] Mass: [(M+H)+]: 292

[0295]

[0296] [Preparation Example 11] Synthesis of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (A11)

[0297]

[0298] 2-chloro-1,10-phenanthroline (30.0 g, 139.8 mmol) and (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (32.5 g, 139.8 mmol), Pd(PPh3)4 (4.8 g, 4.2 mmol), and K2CO3 (57.9 g, 419.3 mmol) were added to 360 ml of toluene, 60 ml of ETOH, and 60 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (42.0 g, 114.6 mmol, yield 82%).

[0299] Mass: [(M+H)+]: 368

[0300]

[0301] [Preparation Example 12] Synthesis of 3-(2-chloro-9-phenyl-9H-fluoren-9-yl)pyridine ( B01-1 )

[0302]

[0303] 2-Bromo-4'-chloro-1,1'-biphenyl (30.0 g, 112.1 mmol) was added to 350 ml of anhydrous THF, cooled to -78℃ under a nitrogen atmosphere, and n-BuLi (53.8 mL of 2.5 M in hexane, 134.6 mmol) was slowly added dropwise and reacted for 1 hour. Afterwards, the reacted mixture was added dropwise to a mixture of phenyl(pyridin-3-yl)methanone (20.5 g, 112.1 mmol) (THF, 100 ml, -78℃), stirred at room temperature for 4 hours, quenched with NH4Cl solution, extracted with methylene chloride, and the organic layer was washed with water and concentrated to obtain B01-2. This was dissolved again in 300 ml of HOAc, and a catalytic amount of H2SO4 was added, followed by heating and refluxing for 5 hours. Afterwards, the solid product was filtered, washed with 1 M sodium hydroxide aqueous solution, and filtered to obtain the target compound 3-(2-chloro-9-phenyl-9H-fluoren-9-yl)pyridine (27.8 g, 78.5 mmol, yield 70%).

[0304] Mass: [(M+H)+] :355

[0305]

[0306] [Preparation Example 13] Synthesis of 3,3'-(2-chloro-9H-fluorene-9,9-diyl)dipyridine (B02-1)

[0307]

[0308] 2-Bromo-4'-chloro-1,1'-biphenyl (30.0 g, 112.1 mmol) was added to 350 ml of anhydrous THF, cooled to -78℃ under a nitrogen atmosphere, and n-BuLi (53.8 ml of 2.5 M in hexane, 134.6 mmol) was slowly added dropwise and reacted for 1 hour. Afterwards, the reacted mixture was added dropwise to a mixture of Di(pyridin-3-yl)methanone (20.7 g, 112.1 mmol) (THF, 100 ml, -78℃), stirred at room temperature for 4 hours, quenched with NH4Cl solution, extracted with methylene chloride, and the organic layer was washed with water and concentrated to obtain B02-2. This was dissolved again in 300 ml of HOAc, and a catalytic amount of H2SO4 was added, followed by heating and refluxing for 5 hours. Afterwards, the solid product was filtered, washed with 1 M sodium hydroxide aqueous solution, and filtered to obtain the target compound 3,3'-(2-chloro-9H-fluorene-9,9-diyl)dipyridine (27.9 g, 78.5 mmol, yield 70%).

[0309] Mass: [(M+H)+]: 356

[0310]

[0311] [Preparation Example 14] Synthesis of 3-(3-chloro-9-phenyl-9H-fluoren-9-yl)pyridine (B03-1)

[0312]

[0313] 2-Bromo-3'-chloro-1,1'-biphenyl (30.0 g, 112.1 mmol) was added to 350 ml of anhydrous THF, cooled to -78℃ under a nitrogen atmosphere, and n-BuLi (53.8 ml of 2.5 M in hexane, 134.6 mmol) was slowly added dropwise and reacted for 1 hour. Afterwards, the reacted mixture was added dropwise to a mixture of phenyl(pyridin-3-yl)methanone (20.5 g, 112.1 mmol) (THF, 100 ml, -78℃), stirred at room temperature for 4 hours, quenched with NH4Cl solution, extracted with methylene chloride, and the organic layer was washed with water and concentrated to obtain B03-2. This was dissolved again in 300 ml of HOAc, and a catalytic amount of H2SO4 was added, followed by heating and refluxing for 5 hours. Afterwards, the solid product was filtered, washed with 1 M sodium hydroxide aqueous solution, and filtered to obtain the target compound 3-(3-chloro-9-phenyl-9H-fluoren-9-yl)pyridine (27.4 g, 77.4 mmol, yield 69%).

[0314] Mass: [(M+H)+] :355

[0315]

[0316] [Preparation Example 15] Synthesis of 3-(4-chloro-9-phenyl-9H-fluoren-9-yl)pyridine (B04-1)

[0317]

[0318] 2-Bromo-2'-chloro-1,1'-biphenyl (30.0 g, 112.1 mmol) was added to 350 ml of anhydrous THF, cooled to -78℃ under a nitrogen atmosphere, and n-BuLi (53.8 ml of 2.5 M in hexane, 134.6 mmol) was slowly added dropwise and reacted for 1 hour. Afterwards, the reacted mixture was added dropwise to a mixture of phenyl(pyridin-3-yl)methanone (20.5 g, 112.1 mmol) (THF, 100 ml, -78℃), stirred at room temperature for 4 hours, quenched with NH4Cl solution, extracted with methylene chloride, and the organic layer was washed with water and concentrated to obtain B04-2. This was dissolved again in 300 ml of HOAc, and a catalytic amount of H2SO4 was added, followed by heating and refluxing for 5 hours. Afterwards, the solid product was filtered, washed with 1 M sodium hydroxide aqueous solution, and filtered to obtain the target compound 3-(4-chloro-9-phenyl-9H-fluoren-9-yl)pyridine (28.2 g, 79.6 mmol, yield 71%).

[0319] Mass: [(M+H)+]: 355

[0320]

[0321] [Preparation Example 16] Synthesis of 3-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (B01)

[0322]

[0323] B01-1 (30 g, 84.8 mmol), bis(pinacolato) diboron (28.0 g, 110.2 mmol), Pd(dppf)Cl2 (1.9 g, 2.5 mmol), X-Phos (2.4 g, 5.1 mmol), and KOAc (16.6 g, 169.6 mmol) synthesized by the method of Preparation Example 12 were added to 300 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 3-(9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (31.3 g, 70.4 mmol, yield 83%).

[0324] Mass: [(M+H) + ] :446

[0325]

[0326] [Preparation Example 17] Synthesis of 3,3'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-9,9-diyl)dipyridine ( B02 )

[0327]

[0328] B02-1 (30 g, 84.5 mmol), bis(pinacolato) diboron (27.9 g, 109.9 mmol), Pd(dppf)Cl2 (1.9 g, 2.5 mmol), X-Phos (2.4 g, 5.1 mmol), and KOAc (16.6 g, 169.1 mmol) synthesized by the method of Preparation Example 13 were added to 300 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 3,3'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-9,9-diyl)dipyridine (30.6 g, 68.5 mmol, yield 81%).

[0329] Mass: [(M+H) + ] :447

[0330]

[0331] [Preparation Example 18] Synthesis of 3-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (B03)

[0332]

[0333] B03-1 (30 g, 84.8 mmol), bis(pinacolato) diboron (28.0 g, 110.2 mmol), Pd(dppf)Cl2 (1.9 g, 2.5 mmol), X-Phos (2.4 g, 5.1 mmol), and KOAc (16.6 g, 169.6 mmol) synthesized by the method of Preparation Example 14 were added to 300 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 3-(9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (31.3 g, 70.4 mmol, yield 83%).

[0334] Mass: [(M+H) + ] :446

[0335]

[0336] [Preparation Example 19] Synthesis of 3-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (B04)

[0337]

[0338] B04-1 (30 g, 84.8 mmol), bis(pinacolato) diboron (28.1 g, 110.2 mmol), Pd(dppf)Cl2 (1.9 g, 2.5 mmol), X-Phos (2.4 g, 5.1 mmol), and KOAc (16.6 g, 169.6 mmol) synthesized by the method of Preparation Example 15 were added to 300 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, KOAc was removed by filtration, the organic layer was concentrated, and then crystallized with acetone and MeOH to obtain 3-(9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-yl)pyridine (32.1 g, 72.1 mmol, yield 85%).

[0339] Mass: [(M+H) + ] :446

[0340]

[0341] [Synthesis Example 1] Synthesis of 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (010)

[0342]

[0343] A01 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1 and B01 (23.0 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (23.7 g, 41.3 mmol, yield 80%).

[0344] Mass: [(M+H)+]: 575

[0345]

[0346] [Synthesis Example 2] Synthesis of 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-9-phenyl-1,10-phenanthroline (011)

[0347]

[0348] A01 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1 and B02 (23.0 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) synthesized by the method of Preparation Example 12 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-9-phenyl-1,10-phenanthroline (21.1 g, 36.6 mmol, yield 71%).

[0349] Mass: [(M+H)+]: 576

[0350]

[0351] [Synthesis Example 3] Synthesis of 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (012)

[0352]

[0353] A01 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1 and B03 (23.0 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (22.5 g, 39.2 mmol, yield 76%).

[0354] Mass: [(M+H)+]: 575

[0355]

[0356] [Synthesis Example 4] Synthesis of 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-4-yl)-1,10-phenanthroline (014)

[0357]

[0358] A01 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 1 and B04 (23.0 g, 51.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol), and K2CO3 (21.4 g, 154.8 mmol) synthesized by the method of Preparation Example 19 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-phenyl-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-4-yl)-1,10-phenanthroline (22.8 , 39.7 mmol, yield 77%).

[0359] Mass: [(M+H)+]: 575

[0360]

[0361] [Synthesis Example 5] Synthesis of 2-phenyl-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (020)

[0362]

[0363] A04 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4 and B01 (18.2 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-phenyl-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (20.2 g, 31.1 mmol, yield 76%).

[0364] Mass: [(M+H)+]: 651

[0365]

[0366] [Synthesis Example 6] Synthesis of 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-9-phenyl-1,10-phenanthroline (021)

[0367]

[0368] A04 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4 and B02 (18.3 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-9-phenyl-1,10-phenanthroline (19.7 g, 30.3 mmol, yield 74%).

[0369] Mass: [(M+H)+]: 652

[0370]

[0371] [Synthesis Example 7] Synthesis of 2-phenyl-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (022)

[0372]

[0373] A04 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 4 and B03 (18.2 g, 40.9 mmol) and Cs2CO3 (26.6 g, 81.8 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-phenyl-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (20.7 g, 31.9 mmol, yield 78%).

[0374] Mass: [(M+H)+]: 651

[0375]

[0376] [Synthesis Example 8] Synthesis of 2-phenyl-9-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (032)

[0377]

[0378] A05 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 5 and B01 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.0 mmol) and X-Phos (1.0 g, 2.0 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-phenyl-9-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (19.7 g, 27.1 mmol, yield 80%).

[0379] Mass: [(M+H)+]: 727

[0380]

[0381] [Synthetic Example 9] Synthesis of 2-(3'-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline (033)

[0382]

[0383] A05 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 5 and B02 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.0 mmol) and X-Phos (1.0 g, 2.0 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3'-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-9-phenyl-1,10-phenanthroline (18.2 g, 25.1 mmol, yield 74%).

[0384] Mass: [(M+H)+]: 728

[0385]

[0386] [Synthesis Example 10] Synthesis of 2-phenyl-9-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (034)

[0387]

[0388] A05 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 5 and B03 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.0 mmol) and X-Phos (1.0 g, 2.0 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-phenyl-9-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (18.9 g, 26.1 mmol, yield 77%).

[0389] Mass: [(M+H)+]: 727

[0390]

[0391] [Synthesis Example 11] Synthesis of 2-(naphthalen-2-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (076)

[0392]

[0393] A02 (15.0 g, 44.0 mmol) synthesized by the method of Preparation Example 2 and B01 (19.6 g, 44.0 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.2 g, 132.0 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(naphthalen-2-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (22.2 g, 35.7 mmol, yield 81%).

[0394] Mass: [(M+H)+]: 625

[0395]

[0396] [Synthesis Example 12] Synthesis of 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (077)

[0397]

[0398] A02 (15.0 g, 44.0 mmol) synthesized by the method of Preparation Example 2 and B02 (19.6 g, 44.0 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.2 g, 132.0 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-9-(naphthalen-2-yl)-1,10-phenanthroline (22.3 g, 35.7 mmol, yield 81%).

[0399] Mass: [(M+H)+]: 626

[0400]

[0401] [Synthesis Example 13] Synthesis of 2-(naphthalen-2-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (078)

[0402]

[0403] A02 (15.0 g, 44.0 mmol) synthesized by the method of Preparation Example 2 and B03 (19.6 g, 44.0 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), and K2CO3 (18.2 g, 132.0 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(naphthalen-2-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (22.0 g, 35.2 mmol, yield 80%).

[0404] Mass: [(M+H)+]: 625

[0405]

[0406] [Synthesis Example 14] Synthesis of 2-(naphthalen-2-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (080)

[0407]

[0408] A06 (15.0 g, 36.0 mmol) synthesized by the method of Preparation Example 6 and B01 (16.0 g, 36.0 mmol) and Cs2CO3 (23.4 g, 72.0 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.1 mmol) and X-Phos (1.0 g, 2.2 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(naphthalen-2-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (19.9 g, 28.4 mmol, yield 79%).

[0409] Mass: [(M+H)+]: 701

[0410]

[0411] [Synthetic Example 15] Synthesis of 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-9-(naphthalen-2-yl)-1,10-phenanthroline (081)

[0412]

[0413] A06 (15.0 g, 36.0 mmol) synthesized by the method of Preparation Example 6 and B02 (16.1 g, 36.0 mmol) and Cs2CO3 (23.4 g, 72.0 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.1 mmol) and X-Phos (1.0 g, 2.2 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-9-(naphthalen-2-yl)-1,10-phenanthroline (20.2 g, 28.8 mmol, yield 80%).

[0414] Mass: [(M+H)+]: 702

[0415]

[0416] [Synthesis Example 16] Synthesis of 2-(naphthalen-2-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (082)

[0417]

[0418] A06 (15.0 g, 36.0 mmol) synthesized by the method of Preparation Example 6 and B03 (16.0 g, 36.0 mmol) and Cs2CO3 (23.4 g, 72.0 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.1 mmol) and X-Phos (1.0 g, 2.2 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(naphthalen-2-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (20.9 g, 29.9 mmol, yield 83%).

[0419] Mass: [(M+H)+]: 701

[0420]

[0421] [Synthetic Example 17] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (112)

[0422]

[0423] A03 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 3 and B01 (18.2 g, 40.9 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (17.0 g, 122.7 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (21.5 g, 33.1 mmol, yield 81%).

[0424] Mass: [(M+H)+]: 651

[0425]

[0426] [Synthetic Example 18] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (113)

[0427]

[0428] A03 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 3 and B02 (18.3 g, 40.9 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (17.0 g, 122.7 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-9-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (19.7 g, 30.3 mmol, yield 74%).

[0429] Mass: [(M+H)+]: 651

[0430]

[0431] [Synthetic Example 19] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (114)

[0432]

[0433] A03 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 3 and B03 (18.2 g, 40.9 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), and K2CO3 (17.0 g, 122.7 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, extraction was performed with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-3-yl)-9-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (20.5 g, 31.5 mmol, yield 77%).

[0434] Mass: [(M+H)+]: 651

[0435]

[0436] [Synthetic Example 20] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (116)

[0437]

[0438] A08 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 8 and B01 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.0 mmol) and X-Phos (1.0 g, 2.0 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-([1,1'-biphenyl]-3-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (18.4 g, 25.4 mmol, yield 75%).

[0439] Mass: [(M+H)+]: 727

[0440]

[0441] [Synthetic Example 21] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (117)

[0442]

[0443] A08 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 8 and B02 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 17 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.2 g, 1.0 mmol) and X-Phos (1.0 g, 2.0 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-([1,1'-biphenyl]-3-yl)-9-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (19.7 g, 27.1 mmol, yield 80%).

[0444] Mass: [(M+H)+]: 728

[0445]

[0446] [Synthetic Example 22] Synthesis of 2-([1,1'-biphenyl]-3-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (118)

[0447]

[0448] A08 (15.0 g, 33.9 mmol) synthesized by the method of Preparation Example 8 and B03 (15.1 g, 33.9 mmol) and Cs2CO3 (22.1 g, 67.7 mmol) synthesized by the method of Preparation Example 18 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (g, mmol) and X-Phos (g, mmol) were added and heated under active stirring for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-([1,1'-biphenyl]-3-yl)-9-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (20.6 g, 28.4 mmol, yield 84%).

[0449] Mass: [(M+H)+]: 727

[0450]

[0451] [Synthesis Example 23] Synthesis of 2-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (211)

[0452]

[0453] 2-chloro-1,10-phenanthroline (15.0 g, 69.9 mmol) and B01 (31.1 g, 69.9 mmol) synthesized by the method of Preparation Example 16, Pd(PPh3)4 (2.4 g, 2.1 mmol), K2CO3 (29.0 g, 209.6 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (26.8 g, 53.8 mmol, yield 77%).

[0454] Mass: [(M+H)+]: 499

[0455]

[0456] [Synthesis Example 24] Synthesis of 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (216)

[0457]

[0458] 2-chloro-1,10-phenanthroline (15.0 g, 69.9 mmol) and B02 (31.2 g, 69.9 mmol) synthesized by the method of Preparation Example 17, Pd(PPh3)4 (2.4 g, 2.1 mmol), K2CO3 (29.0 g, 209.6 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and the mixture was heated and refluxed for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-1,10-phenanthroline (28.2 g, 56.6 mmol, yield 81%).

[0459] Mass: [(M+H)+]: 500

[0460]

[0461] [Synthesis Example 25] Synthesis of 2-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (219)

[0462]

[0463] 2-chloro-1,10-phenanthroline (15.0 g, 69.9 mmol) and B03 (31.1 g, 69.9 mmol) synthesized by the method of Preparation Example 18, Pd(PPh3)4 (2.4 g, 2.1 mmol), K2CO3 (29.0 g, 209.6 mmol) were added to 180 ml of toluene, 30 ml of ETOH, and 30 ml of water, and the mixture was heated and stirred under reflux for 2 hours. After completion of the reaction, the mixture was extracted with methylene chloride, and the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-1,10-phenanthroline (28.9 g, 58.0 mmol, yield 83%).

[0464] Mass: [(M+H)+]: 499

[0465]

[0466] [Synthesis Example 26] Synthesis of 2-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (227)

[0467]

[0468] A10 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 10 and B01 (23.0 g, 51.6 mmol) synthesized by the method of Preparation Example 16 Cs2CO3 (33.6 g, 103.2 mmol) were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.5 mmol) and X-Phos (1.5 g, 3.1 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (24.9 g, 43.3 mmol, yield 84%).

[0469] Mass: [(M+H)+]: 575

[0470]

[0471] [Synthetic Example 27] Synthesis of 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (228)

[0472]

[0473] A10 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 10 and B02 (23.0 g, 51.6 mmol) synthesized by the method of Preparation Example 17 Cs2CO3 (33.6 g, 103.2 mmol) were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.5 mmol) and X-Phos (1.5 g, 3.1 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)phenyl)-1,10-phenanthroline (24.3 g, 42.3 mmol, yield 82%).

[0474] Mass: [(M+H)+]: 576

[0475]

[0476] [Synthesis Example 28] Synthesis of 2-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (229)

[0477]

[0478] A10 (15.0 g, 51.6 mmol) synthesized by the method of Preparation Example 10 and B03 (23.0 g, 51.6 mmol) synthesized by the method of Preparation Example 18 Cs2CO3 (33.6 g, 103.2 mmol) were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.5 mmol) and X-Phos (1.5 g, 3.1 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)phenyl)-1,10-phenanthroline (24.0 g, 41.8 mmol, yield 81%).

[0479] Mass: [(M+H)+]: 575

[0480]

[0481] [Synthetic Example 29] Synthesis of 2-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (239)

[0482]

[0483] A11 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 11 and B01 (18.2 g, 40.9 mmol) synthesized by the method of Preparation Example 16 were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW. Then, Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (21.0 g, 32.3 mmol, yield 79%).

[0484] Mass: [(M+H)+]: 651

[0485]

[0486] [Synthesis Example 30] Synthesis of 2-(3'-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (240)

[0487]

[0488] A11 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 11 and B02 (18.3 g, 40.9 mmol) synthesized by the method of Preparation Example 17 Cs2CO3 (26.6 g, 81.8 mmol) were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3'-(9,9-di(pyridin-3-yl)-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (21.3 g, 32.7 mmol, yield 80%).

[0489] Mass: [(M+H)+]: 652

[0490]

[0491] [Synthesis Example 31] Synthesis of 2-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (241)

[0492]

[0493] A11 (15.0 g, 40.9 mmol) synthesized by the method of Preparation Example 11 and B03 (18.2 g, 40.9 mmol) synthesized by the method of Preparation Example 18 Cs2CO3 (26.6 g, 81.8 mmol) were added to 180 ml of toluene, 30 ml of EtOH, and 30 ml of DIW, and then Pd(OAc)2 (0.3 g, 1.2 mmol) and X-Phos (1.2 g, 2.5 mmol) were added and heated and stirred under active current for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and the solid was filtered. The filtered solid was purified by column chromatography to produce 2-(3'-(9-phenyl-9-(pyridin-3-yl)-9H-fluoren-3-yl)-[1,1'-biphenyl]-3-yl)-1,10-phenanthroline (21.8 g, 33.5 mmol, yield 82%).

[0494] Mass: [(M+H)+] :651

[0495]

[0496] [Example 1] Fabrication of a blue organic electroluminescent device

[0497] Compound 010 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

[0498] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0499] On the ITO transparent electrode prepared as described above, compounds 1 and 2 were co-deposited at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, then compound 1 was deposited on top of the hole injection layer to form a hole transport layer having a thickness of 1400 Å, then compound 3 was deposited on top of the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and compounds 4 and 5 were co-deposited at a weight ratio of 98:2 to form a light emitting layer having a thickness of 200 Å. Afterwards, compound 6 was deposited on the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then compound 010 and compound 7 were co-deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then Al was deposited on the electron injection layer to form a cathode with a thickness of 1000 Å, thereby manufacturing the blue organic electroluminescent device of Example 1.

[0500] The structures of compounds 1 to 7 used at this time are as follows.

[0501]

[0502]

[0503] [Examples 2 to 31] Fabrication of blue organic electroluminescent devices

[0504] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds described in Table 1 below was used instead of Compound 010, which was used as an electron transport layer material in Example 1.

[0505]

[0506] [Comparative Examples 1 to 5] Fabrication of blue organic electroluminescent devices

[0507] Blue organic electroluminescent devices of Comparative Examples 1 to 5 were manufactured in the same manner as in Example 1, except that Compounds A to E were used instead of Compound 010, which was used as an electron transport layer material in Example 1.

[0508]

[0509]

[0510] [Evaluation Example 1]

[0511] For the blue organic electroluminescent devices manufactured in Examples 1 to 31 and Comparative Examples 1 to 5, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0512] Sample Electron Transport Layer Driving Voltage (V) Current Efficiency (cd / A) Lifetime (h) Example 1 Compound 0103.87.9328 Example 2 Compound 0114.08.1320 Example 3 Compound 0123.98.0317 Example 4 Compound 0144.08.1298 Example 5 Compound 0204.18.3285 Example 6 Compound 0213.78.2312 Example 7 Compound 0223.88.4326 Example 8 Compound 0323.97.9250 Example 9 Compound 0334.08.2380 Example 10 Compound 0344.08.3376 Example Compound 11 0763.88.5298 Example 12 Compound 0773.98.3330 Example 13 Compound 0783.98.9330 Example 14 Compound 0803.89.0319 Example 15 Compound 0813.98.9300 Example 16 Compound 0823.78.9318 Example 17 Compound 1123.68.8308 Example 18 Compound 1133.78.7304 Example 19 Compound 1143.98.7302 Example 20 Compound 1163.88.7299 Example 21 Compound 1173.88.8300 Example 22 Compound 1183.98.6312 Example 23 Compound 2113.98.6322 Example 24 Compound 2163.98.1310 Example 25 Compound 2194.08.6309 Example 26 Compound 2273.98.6308 Example 27 Compound 2283.98.8298 Example 28 Compound 2293.88.9299 Example 29 Compound 2393.88.9300 Example 30 Compound 2403.98.9305 Example 31 Compound 2413.88.8302 Comparative Example 1 Compound A4.56.7210 Comparative Example 2 Compound Comparative Example 3 Compound B4.56.8220 Comparative Example 4 Compound C4.76.7180 Comparative Example 4 Compound D4.96.8165 Comparative Example 5 Compound E4.76.2150

[0513] As shown in Table 1 above, the blue organic electroluminescent devices of Examples 1 to 31, which used the compounds of the present invention, in which a core structure in which a nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position of a fluorene moiety and a phenanthroline moiety are combined, as electron transport layer materials, were found to exhibit superior performance in terms of driving voltage, emission peak, current efficiency, and device lifespan compared to the blue organic electroluminescent devices of Comparative Examples 1 to 2, in which a control compound (e.g., A to B) not including a phenanthroline moiety is used as an electron transport layer material; and the blue organic electroluminescent devices of Comparative Examples 3 to 5, in which a control compound (e.g., C to E) not including a fluorene moiety in which a nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position is used as an electron transport layer material.

[0514]

[0515] [Example 32] Fabrication of an organic electroluminescent device

[0516] Compound 010 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

[0517] First, a glass substrate coated with a 1500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV light and transferred to a vacuum deposition machine.

[0518] On the ITO transparent electrode prepared as above, compounds 1 and 2 were co-deposited at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, then compound 1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å, then compound 3 was deposited on the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and compounds 4 and 5 were co-deposited at a weight ratio of 98:2 to form a light-emitting layer having a thickness of 200 Å. Thereafter, compound 8 was deposited on the light-emitting layer to a thickness of 150 Å to form an electron transport region, and compound 010 was deposited on the electron transport region to a thickness of 50 Å with 2% Li to form an N-type charge generation layer (CGL). Compound 2 was deposited on an N-type charge generation layer to a thickness of 50 Å to form a P-type charge generation layer (CGL), and compounds 1 and 2 were co-deposited on the P-type charge generation layer at a weight ratio of 98:2 to form a hole injection layer to a thickness of 100 Å. Then, compound 1 was deposited on the hole injection layer to form a hole transport layer to a thickness of 350 Å. Then, compound 3 was deposited on the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and then compounds 4 and 5 were co-deposited on the P-type charge generation layer at a weight ratio of 98:2 to form a light-emitting layer to a thickness of 200 Å. Afterwards, compound 6 was deposited on the light-emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, then compounds 7 and 8 were deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then Al was deposited on the electron injection layer to form a cathode with a thickness of 1000 Å, thereby manufacturing an organic electroluminescent device.

[0519] At this time, the structures of compounds 1 to 7 used are the same as in Example 1, and the structure of compound 8 is as follows.

[0520]

[0521]

[0522] [Examples 33 to 62] Fabrication of organic electroluminescent devices

[0523] An organic electroluminescent device was manufactured in the same manner as in Example 32, except that each compound in Table 2 was used instead of compound 010 used as the N-type charge generation layer material in Example 32.

[0524]

[0525] [Comparative Examples 6 to 10] Fabrication of Organic Electroluminescent Devices

[0526] Organic electroluminescent devices of Comparative Examples 6 to 10 were manufactured in the same manner as in Example 32, except that Compounds A to E were used instead of Compound 010, which was used as a charge generation layer material.

[0527] Compounds A to E used at this time are the same as Comparative Examples 1 to 5.

[0528]

[0529] [Evaluation Example 2]

[0530] For the organic electroluminescent devices manufactured in Examples 32 to 62 and Comparative Examples 6 to 10, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0531] SampleN-type charge generation layerDrive voltage(V)Current efficiency(cd / A)Lifespan(h)Example 32Compound 0108.015.9320Example 33Compound 0118.015.8350Example 34Compound 0128.015.5351Example 35Compound 0148.115.5351Example 36Compound 0207.715.6349Example 37Compound 0217.515.6340Example 38Compound 0227.615.6340Example 39Compound 0327.515.7352Example 40Compound 0337.815.4351Example 41Compound 0347.915.5355 Example 42 Compound 0767.915.6333 Example 43 Compound 0777.615.8340 Example 44 Compound 0787.615.9332 Example 45 Compound 0807.716.0331 Example 46 Compound 0817.815.9334 Example 47 Compound 0827.715.5310 Example 48 Compound 1127.915.7306 Example 49 Compound 1137.815.8306 Example 50 Compound 1147.815.8305 Example 51 Compound 1167.715.6311 Example 52 Compound 1177.515.6316 Example 53 Compound 1187.615.9318 Example 54 Compound 2117.715.8321 Example 55 Compound 2167.815.9323 Example 56 Compound 2197.815.9321 Example 57 Compound 2277.615.6333 Example 58 Compound 2287.615.4310 Example 59 Compound 2297.815.9355 Example 60 Compound 2397.815.8298 Example 61 Compound 2407.615.3298 Example 62 Compound 2418.815.4330 Comparative Example 6 Compound A8.914.1150 Comparative Example 7 Compound B8.714.2160 Comparative Example 8 Compound C8.814.0160 Comparative Example 9 Compound D8.914.0162 Comparative Example 10 Compound E9.012.0172

[0532]

[0533] As shown in Table 2 above, the blue organic electroluminescent devices of Examples 32 to 62 using the compound of the present invention, in which a core structure in which a nitrogen-containing heteroaromatic ring is introduced at the 9th carbon position of a fluorene moiety and a phenanthroline moiety are combined, as an N-type charge generation layer (CGL) material, are comparable to the blue organic electroluminescent devices of Comparative Examples 5 to 6 using control compounds (e.g., A to B) not including a phenanthroline moiety as an N-type charge generation layer (CGL) material; And, compared to the blue organic electroluminescent devices of Comparative Examples 8 to 10 using control compounds (e.g., C to E) that do not contain a fluorene moiety with a nitrogen-containing heteroaromatic ring introduced at the 9th carbon position as an N-type charge generation layer (CGL) material, it was found that the devices exhibited superior performance in terms of driving voltage, emission peak, current efficiency, and device lifespan.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 Inland R 3 are identical or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 3 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group of , and C 6 ~C 60 is selected from the group consisting of arylamine groups, and only R 1 Inland R 3 At least one of them is a moiety represented by the following chemical formula 1A, a and b are each independently an integer from 0 to 3, c is an integer from 0 to 2, [Chemical Formula 1A] In the above chemical formula 1A, X 1 Inland X 10 are identical or different from each other, and each independently represents N or C(R 4 ) and only X 1 Inland X 10 At least one of them is N, R 4 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 3 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group of , and C 6 ~C 60 is selected from the group consisting of arylamine groups, and the R 4 If there are multiple R's, there are multiple R's 4 are identical or different from each other, L 1 and L 2 are identical or different from each other, and each independently represents a single bond, or C 6 ~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, m and n are each independently integers from 0 to 3, Ar 1 Silver hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 is selected from the arylamine group of , Above L 1 Inside L 2 Arylene group and heteroarylene group of Ar, 1 , R 1 Inland R 4 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylsilyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they may be the same or different from each other.

2. In paragraph 1, Above X 1 Inland X 5 A ring moiety containing the above X 6 Inland X 10 A compound wherein the ring moieties are the same or different from each other and are each selected from the following structural formulas: In the above formula, * indicates a part connected to the chemical formula 2 above, Multiple R's 4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, an alkyl group, an aryl group, and a heteroaryl group.

3. In paragraph 1, Above X 1 Inland X 10 The ring moiety is a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the chemical formula 1 above, Ar 1 , L 1 , L 2 , m and n are as defined in Article 1, respectively.

4. In paragraph 1, R 1 Inland R 3 , and Ar 1 are identical or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, C 1 ~C 40 Alkyl group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

5. In paragraph 1, R 1 Inland R 3 , and Ar 1 are identical or different from each other, and each independently selected from the following structural formulae: In the above formula, * indicates a part connected to the chemical formula 1 above, R 5 is hydrogen, deuterium (D), C 1 ~C 40 Alkyl group of C 6 ~C 60 It is selected from the group consisting of an aryl group of and a heteroaryl group having 5 to 18 nuclear atoms.

6. In paragraph 1, L 1 and L 2 are identical or different from each other, and each independently represents a single bond or a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the chemical formula 1 above, R 6 is hydrogen, deuterium (D), C 1 ~C 40 Alkyl group of C 6 ~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms.

7. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 2 or chemical formula 3: [Chemical formula 2] [Chemical Formula 3] In the above chemical formula 2 or 3, X 1 ~X 10 , Ar 1 , R 1 ~R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

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 4 to 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] In the above chemical formulas 4 to 7, X 1 ~X 10 , Ar 1 , R 1 ~R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 8 to 11: [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] In the above chemical formulas 8 to 11, X 1 ~X 10 , Ar 1 , R 1 ~R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

10. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 12 to 21: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical formula 20] [Chemical Formula 21] In the above chemical formulas 12 to 21, X 1 ~X 10 , Ar 1 , R 1 ~R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

11. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 22 to 25: [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] In the above chemical formulas 22 to 25, Z 1 Inland Z 3 are identical or different from each other, and each independently represents N or C(R 11 ) and only Z 1 Inland Z 3 At least one of them is N, R 11 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 3 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group of , and C 6 ~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring, and the R 11 In this case, multiple R 11 are identical or different from each other, Ar 2 and Ar 3 are identical or different from each other, and each independently represents hydrogen, deuterium (D), and C. 1 ~C 40 Alkyl group of C 6 ~C 60 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, Y is O or S, Ring A is a divalent aromatic condensed polycyclic group, o is an integer from 1 to 3, X 1 ~X 10 , Ar 1 , R 1 , R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

12. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 26 to 29: [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] In the above chemical formulas 26 to 29, Z 1 Inland Z 3 are identical or different from each other, and each independently represents N or C(R 11 ) and only Z 1 Inland Z 3 At least one of them is N, R 11 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 3 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 1 ~C 40 Alkylphosphine group of C 6 ~C 60 Arylphosphine group of C 1 ~C 40 Alkylphosphine oxide group of C 6 ~C 60 Arylphosphine oxide group of , and C 6 ~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring, and the R 11 In this case, multiple R 11 are identical or different from each other, Ar 2 and Ar 3 are identical or different from each other, and each independently represents hydrogen, deuterium (D), and C. 1 ~C 40 Alkyl group of C 6 ~C 60 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, Y is O or S, Ring A is a divalent aromatic condensed polycyclic group, o is an integer from 1 to 3, X 1 ~X 10 , R 1 ~R 3 , L 1 ~L 2 , m, and n are as defined in Article 1, respectively.

13. 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 324.

14. In paragraph 1, The compound represented by the above chemical formula 1 is a compound used as at least one material selected from the group consisting of a light-emitting layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, and an N-type charge generation layer.

15. 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 14.

16. In paragraph 15, An organic electroluminescent device, wherein the organic layer containing the compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a life-span improving layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer.

17. In paragraph 15, The above organic electroluminescent device, a plurality of light-emitting layer stacks comprising at least one light-emitting layer; and It further includes a charge generation layer disposed between adjacent stacks among the plurality of light-emitting layer stacks; An organic electroluminescent device, wherein the charge generation layer comprises the compound.

18. In paragraph 17, An organic electroluminescent device, wherein the charge generation layer comprising the above compound is an N-type charge generation layer.

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