Organic compound and organic electroluminescent device comprising same

Abstract

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

Description

Organic compounds and organic electroluminescent devices containing the same

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

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

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

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

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

[0006] The present invention aims to provide a novel compound having improved electron injection and transport capabilities and excellent thermal stability, which can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer material or an electron transport auxiliary layer material.

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

[0008] To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1:

[0009]

[0010] (In the above chemical formula 1,

[0011] Rings Cy1 and Cy2 are the same or different from each other and are each independently selected from the group consisting of a 6-membered monocyclic heteroaromatic ring containing 1 to 2 nitrogen atoms and a 9 to 30-membered polycyclic heteroaromatic ring containing 1 to 4 nitrogen atoms,

[0012] a and b are integers from 0 to 4, respectively,

[0013] Ar1 and Ar2 are the same or different and are hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxy 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0014] Q1 is deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl 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 40Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0015] c is an integer from 0 to 4,

[0016] d is an integer from 0 to 3,

[0017] R1 and R2 are the same or different, and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0018] n is an integer from 0 to 3,

[0019] L1 is a single bond, or C1~C 20 alkylene group, C2~C 40 Alkenylene group, C6~C 30Selected from the group consisting of an arylene group, a heteroarylene group having 5 to 30 nuclear atoms, and a divalent ether group (-O-),

[0020] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1, Ar2, Q1, R1 and R2, and the alkylene group, alkenylene group, arylene group and heteroarylene group of the above L1 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0021] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0022] For example, the organic layer including the organic compound may be an electron transport layer and / or an electron transport auxiliary layer.

[0023] The compound of the present invention can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc. In particular, when the compound of the present invention is used as at least one of an electron transport layer material and an electron transport auxiliary layer material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be manufactured, and further, a full-color display panel with improved performance and lifespan can also be manufactured.

[0024] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0025] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0026] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0027] <Explanation of symbols>

[0028] 100: positive, 200: negative,

[0029] 300: Organic layer, 310: Hole injection layer,

[0030] 320: hole transport layer, 330: light emitting layer,

[0031] 340: electron transport layer, 350: electron injection layer,

[0032] 360: Electron transport auxiliary layer

[0033] Hereinafter, the present invention will be described.

[0034] <New organic compounds>

[0035] The compound according to the present invention has a basic structure including a biphenylene moiety; a first nitrogen-containing heteroaromatic ring bonded to one benzene ring of the biphenylene moiety; a specific substituent (e.g., a phenyl group, etc.) bonded to one benzene ring of the biphenylene moiety at an ortho-position with respect to the first nitrogen-containing heteroaromatic ring; and a second nitrogen-containing heteroaromatic ring bonded directly or via a linker group (e.g., a phenyl group, etc.) to the other benzene ring of the biphenylene moiety, and is represented by the above chemical formula 1. The compound of the present invention represented by the above chemical formula 1 has excellent electron injection and transport ability, electrochemical stability, thermal stability, etc., and can be used as a high-efficiency organic layer material, particularly an electron transport layer material and an electron transport auxiliary layer material.

[0036] Specifically, in the compound represented by the above chemical formula 1, the first and second nitrogen-containing heteroaromatic rings are a 6-membered monocyclic heteroaromatic ring containing 1 to 2 nitrogens (N), or a 9 to 30-membered polycyclic heteroaromatic ring containing 1 to 4 nitrogens, which may be an electron-withdrawing group (EWG) with high electron absorption. The compound of the present invention containing the first and second nitrogen-containing heteroaromatic ring groups has a shallow LUMO energy level, thereby improving electron mobility and thus exhibiting excellent electron transport properties. Therefore, when the compound according to the present invention is applied as a material for an electron transport layer or an electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light-emitting layer, and as a result, the driving voltage of the device can be lowered, and high efficiency and long life characteristics can be realized.

[0037] In addition, a specific substituent (Q) such as a phenyl group is introduced at the ortho-position to the benzene ring based on the first nitrogen-containing heteroaromatic ring. That is, the first nitrogen-containing heteroaromatic ring group and the specific substituent are introduced at positions 1 and 2 of the benzene ring, respectively. Accordingly, as the dihedral angle between the first nitrogen-containing heteroaromatic ring and the specific substituent increases, charge transport characteristics (e.g., electron transport characteristics) are enhanced, so that the compound of the present invention can be used as a low-voltage, high-efficiency electron transport layer material.

[0038] In addition, the compound of the present invention can significantly increase its molecular weight by introducing various substituents (e.g., alkyl group, aryl group, heteroaryl group, etc.) into the first and second nitrogen-containing heteroaromatic rings, thereby increasing the glass transition temperature and improving thermal safety and electrochemical stability.

[0039] As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron transport ability, thermal stability, electrochemical stability, etc., and thus can be used as an organic layer material of an organic electroluminescent device, specifically, an emission layer material, an electron transport layer / injection layer material, an electron transport auxiliary layer material, and more specifically, an electron transport layer material, an electron transport auxiliary layer material. In addition, an organic electroluminescent device including the compound of the chemical formula 1 can have significantly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

[0040]

[0041] In the chemical formula 1 according to the present invention, rings Cy1 and Cy2 are a type of electron-withdrawing group (EWG) with high electron absorption among nitrogen-containing heteroaromatic rings, which can improve electron mobility and thus electron transport properties of the compound. In particular, ring Cy1 is bonded to the benzene ring in an ortho-position based on a specific substituent (Q1). As a result, the compound of the present invention has enhanced electron transport properties and can be used as an electron transport layer material or an electron transport auxiliary layer material of an organic electroluminescent device. These rings Cy1 and Cy2 are the same as or different from each other, and are each independently selected from the group consisting of a 6-membered monocyclic heteroaromatic ring containing 1 to 2 nitrogens (e.g., a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group) and a 9 to 30-membered polycyclic heteroaromatic ring containing 1 to 4 nitrogens (e.g., a quinoline group, an isoquinoline group, a pyrazine group, a quinoxaline group, a quinazoline group, a cinnoline, a phthalazine, a benzofuro-pyridine group, etc.). In this case, the polycyclic heteroaromatic ring may additionally contain a heteroatom other than nitrogen (N) (e.g., O, S, Se, etc.). In addition, multiple rings within the polycyclic heteroaromatic ring may be the same as or different from each other.

[0042] In chemical formula 1 according to the present invention, a and b are each an integer from 0 to 4, and specifically an integer from 0 to 2.

[0043] Here, when a is 0, it means that hydrogen is not substituted with the substituent Ar1, and when b is 0, it means that hydrogen is not substituted with the substituent Ar2. On the other hand, when a is an integer from 1 to 4, it means that hydrogen is substituted with the substituent Ar1, and when b is an integer from 1 to 4, it means that hydrogen is substituted with the substituent Ar2. At this time, a plurality of Ar1s are the same or different from each other, and a plurality of Ar2s are the same or different from each other.

[0044] Ar1 and Ar2 are the same or different and are hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0045] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C40 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0046] Specifically, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0047] More specifically, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently at least one selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, carbazole group and fluorene group. It may be substituted or unsubstituted with a substituent. If there are multiple substituents, they may be the same or different.

[0048] According to these rings Cy1, Cy2, Ar1 and Ar2, the compound represented by the above chemical formula 1 and The moieties may be identical or different and may be independently represented by any one of the following chemical formulae H1 to H5, but are not limited thereto.

[0049] [Chemical formula H1]

[0050]

[0051] [Chemical formula H2]

[0052]

[0053] [Chemical formula H3]

[0054]

[0055] [Chemical formula H4]

[0056]

[0057] [Chemical formula H5]

[0058]

[0059] In the above chemical formulas H1 to H5,

[0060] X1 to X5 are the same or different from each other, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different from each other;

[0061] X6 to X9 are the same or different from each other, and are each independently selected from the group consisting of N or C(Ar4), provided that at least one of X6 to X9 is N, and in this case, one carbon of C(Ar4) other than N can be connected to the above chemical formula 1, and a plurality of C(Ar4) are the same or different from each other;

[0062] X 10 Inland X 13 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 Inland X 13 At least one of them is N, wherein the plurality of C(Ar5) are the same or different;

[0063] Y1 is O, S or C(Ar6)(Ar7),

[0064] X 14 Inland X 17 are identical or different from each other, and each is independently N or C(Ar8), and only X 14 Inland X 17 At least one of them is N, wherein the plurality of C(Ar8) are the same or different;

[0065] X 18 Inland X 21 are identical or different from each other, and each is independently N or C(Ar9), and only X 18 Inland X 21 At least one of them is N, wherein the plurality of C(Ar9) are the same or different;

[0066] e is an integer from 0 to 3,

[0067] f is an integer from 0 to 7,

[0068] Ar3 to Ar9 and R are the same or different and each independently represent hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., Ar3-Ar3, Ar4-Ar4, Ar5-Ar5, Ar6-Ar7, Ar8-Ar8, Ar9-Ar9, RR, etc.) to form a condensed ring, and specifically, each independently comprises deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30is selected from the group consisting of arylamine groups, or can form a condensed ring by condensation with adjacent groups (e.g., Ar3-Ar3, Ar4-Ar4, Ar5-Ar5, Ar6-Ar7, Ar8-Ar8, Ar9-Ar9, RR, etc.);

[0069] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 to Ar9 and R are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other. Here, the condensed ring is C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 fused aromatic ring), fused heteroaromatic ring having 5 to 60 members (specifically, fused heteroaromatic ring having 5 to 30 members), C3 to C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0070] According to another example, the above and The moieties may be identical or different and may be independently selected from the group consisting of the following moieties Mo1-1 to Mo1-38, but are not limited thereto.

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] In the above moiety Mo1-1,

[0077] X1, X2, X3 and X5 are the same or different and are each independently N or C(Ar3), wherein one or two of X1, X2, X3 and X5 are N,

[0078] In the above moiety Mo1-2,

[0079] X1 and X5 are the same or different, and are each independently N or C(Ar3), wherein one or two of X1 and X5 are N,

[0080] In the above moieties Mo1-3,

[0081] X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X2 and X5 are N,

[0082] In the above moieties Mo1-4, Mo1-8 and Mo1-12,

[0083] X1, X4 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X4 and X5 are N,

[0084] In the above moieties Mo1-5, Mo1-9 and Mo1-13,

[0085] X1, X2 and X5 are the same or different and are each independently N or C(Ar3), wherein one or two of X1, X2 and X5 are N,

[0086] In the above moieties Mo1-6, Mo1-7, Mo1-10, Mo1-11, Mo1-14 and Mo1-15,

[0087] X3, X4 and X5 are the same or different and are each independently N or C(Ar3), wherein one or two of X3, X4 and X5 are N,

[0088] In the above moieties Mo1-2, Mo1-3, Mo1-8 to Mo1-11,

[0089] Ring Cy3 is C6~C 30 is a condensed aromatic ring,

[0090] In the above moieties Mo1-4 to Mo1-11,

[0091] Z1 is selected from the group consisting of O, S, C(R3)(R4) and oxo group (=O),

[0092] In the above moieties Mo1-12 to Mo1-15,

[0093] Z2 is selected from the group consisting of O, S, C(R5)(R6) and oxo group (=O),

[0094] In the above moiety Mo1-16,

[0095] X1, X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X2 and X5 are N,

[0096] In the above moiety Mo1-17,

[0097] X1, X4 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X4 and X5 are N,

[0098] In the above moiety Mo1-18,

[0099] X3, X4 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X3, X4 and X5 are N,

[0100] In the above moieties Mo1-16 to Mo1-18,

[0101] X 22 Inland X 25 are identical or different from each other, and each independently represents N or C(Ar 10 ) and at this time X 22 Inland X 25 At least one of them is N,

[0102] In the above moieties Mo1-19, Mo1-22 and Mo1-24,

[0103] X1, X2 and X3 are the same or different from each other, and are each independently N or C(Ar3), wherein one of X1, X2 and X3 is N,

[0104] In the above moieties Mo1-20 and Mo1-23,

[0105] X1, X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one of X1, X2 and X5 is N,

[0106] In the above moiety Mo1-21,

[0107] X1, X4 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one of X1, X4 and X5 is N,

[0108] In the above moieties Mo1-23 and Mo1-24,

[0109] X 26 Inland X 29 are identical or different from each other, and each independently represents N or C(Ar 11 ) and at this time X 26 Inland X 29 At least one of them is N,

[0110] In the above moiety Mo1-25,

[0111] X6, X7 and X9 are the same or different and are each independently N or C(Ar4), wherein at least one of X6, X7 and X9 is N,

[0112] In the above moieties Mo1-26, Mo1-28 and Mo1-29,

[0113] X6, X8 and X9 are the same or different and are each independently N or C(Ar4), wherein at least one of X6, X8 and X9 is N,

[0114] In the above moiety Mo1-27,

[0115] X7, X8 and X9 are the same or different and are each independently N or C(Ar4), wherein at least one of X7, X8 and X9 is N,

[0116] In the above moiety Mo1-29,

[0117] X 30 Inland X 33are identical or different from each other, and each independently represents N or C(Ar 12 ) and at this time X 30 Inland X 33 At least one of them is N,

[0118] In the above moieties Mo1-30 and Mo1-31,

[0119] X 10 and X 13 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 and X 13 At least one of them is N,

[0120] In the above moiety Mo1-32,

[0121] X 34 Inland X 41 are identical or different from each other, and each independently represents N or C(Ar 13 ) and,

[0122] In the above moiety Mo1-33,

[0123] X 10 and X 11 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 and X 11 At least one of them is N,

[0124] In the above moieties Mo1-34 to Mo1-37,

[0125] X 14 Inland X 17 are identical or different from each other, and each is independently N or C(Ar8), and only X 14 Inland X 17 At least one of them is N,

[0126] In the above moiety Mo1-36,

[0127] Ak1 and Ak2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40Alkyl 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 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

[0128] In the above moiety Mo1-37,

[0129] Z3 is selected from the group consisting of O, S, C(R7)(R8) and oxo group (=O),

[0130] In the above moiety Mo1-38,

[0131] X 18 and X 21 are identical or different from each other, and each is independently N or C(Ar9), and only X 10 and X 11 At least one of them is N,

[0132] d is an integer from 0 to 3,

[0133] Ar3 to Ar 13 , R3 to R8 and R are the same or different from each other, are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), 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 40Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., Ar3-Ar3, Ar4-Ar4, Ar5-Ar5, Ar6-Ar7, Ar8-Ar8, Ar9-Ar9, R3-R4, R5-R6, R7-R8, RR, etc.) to form a condensed ring, and specifically, each independently comprises deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 is selected from the group consisting of arylamine groups, or can form a condensed ring by condensation with adjacent groups (e.g., Ar3-Ar3, Ar4-Ar4, Ar5-Ar5, Ar6-Ar7, Ar8-Ar8, Ar9-Ar9, R3-R4, R5-R6, R7-R8, RR, etc.);

[0134] The above Ar3 to Ar 13 , R3 to R8 and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of R are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 60Aryl group of , heteroaryl group having 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other.

[0135] According to another example, the above and The moieties may be identical or different and may be independently selected from the group consisting of the following moieties Mo2-1 to Mo2-72, but are not limited thereto.

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] In the above moieties Mo2-1 to Mo2-72,

[0144] * indicates the part that is combined with chemical formula 1,

[0145] Ar3, Z1, Ar4 and Z3 are as defined in the above moieties Mo1-1 to Mo1-38, respectively,

[0146] f is an integer from 0 to 2.

[0147] The above moieties Mo2-1 to Mo2-72 are deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups and heteroaryl groups having 5 to 10 nuclear atoms.

[0148] The compound represented by chemical formula 1 according to the present invention may be a compound represented by any one of the following chemical formulas 2 to 6, depending on the aforementioned ring Cy1, but is not limited thereto.

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] In the above chemical formulas 2 to 6,

[0155] Rings Cy2, Q1, b, c, d, R1, R2, Ar2, n and L1 are each as defined in the above chemical formula 1,

[0156] X1 to X 21 , Y1, e, f, Ar3 to Ar9 and R are as defined in the chemical formulas H1 to H5 described above, respectively.

[0157] The compound represented by chemical formula 1 according to the present invention may be a compound represented by any one of the following chemical formulas 7 to 26, depending on the bonding position between the benzene ring bonded to Q1 and the adjacent benzene ring, but is not limited thereto.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] In the above chemical formulas 7 to 26,

[0179] Rings Cy2, Q1, b, c, d, R1, R2, Ar2, n and L1 are each as defined in the above chemical formula 1,

[0180] X1 to X 21 , Y1, e, f, Ar3 to Ar9 and R are as defined in the chemical formulas H1 to H5 described above, respectively.

[0181] In the chemical formula 1 according to the present invention, Q1 is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0182] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Q1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other.

[0183] For example, Q1 may be selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, an anthracenyl group, an anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, and a phenanthrolinyl group, which are selected from the group consisting of deuterium (D), Halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups and heteroaryl groups having 5 to 10 nuclear atoms.

[0184] For example, Q1 may be selected from the group consisting of deuterium (D), a cyano group (-CN), and the following substituents S1-1 to S1-44, but is not limited thereto.

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] In the above substituents S1-1 to S1-44,

[0192] Y2, Y3, and Y4 are each independently O, S, C(R9)(R 10 ), N(R 11 ) and sulfonyl group (-S(=O)2-),

[0193] A1 to A4 are identical or different, and each independently represents N or C(R 12 ) and at least one of A1 to A4 is N,

[0194] Y5 and Y6 are identical or different and are independently O, S, C(R 13 )(R 14 ) and N(R 15 ) is selected from the group consisting of,

[0195] Y7 is O, S, C(R 16 )(R 17 ) and N(R 18 ) is selected from the group consisting of,

[0196] Ring Cy4 is present or absent, and when ring Cy4 is present, ring Cy4 is C6~C 18 It is a condensed ring, specifically C6~C 18 It may be a condensed aromatic ring,

[0197] g is an integer from 0 to 5, specifically an integer from 0 to 3,

[0198] h is an integer from 0 to 4, specifically an integer from 0 to 2,

[0199] i is an integer from 0 to 7, specifically an integer from 0 to 3,

[0200] j is 0 or 1,

[0201] k is an integer from 0 to 8, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0202] l is an integer from 0 to 6, specifically an integer from 0 to 3,

[0203] m is an integer from 0 to 9, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0204] Multiple R's are the same or different from each other,

[0205] R9 to R 18 and R are the same or different, and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 selected from the group consisting of arylamine groups, or adjacent groups (e.g. R9-R 10 , R 12 -R 12 , R 13 -R 14 , R 16 -R 17 , RR, etc.) to form a condensed ring, and specifically, each independently comprises deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 is selected from the group consisting of arylamine groups, or adjacent groups (e.g. R9-R 10 , R 12 -R 12 , R 13 -R 14 , R 16 -R 17 , RR, etc.) can be condensed to form a condensed ring. Here, the condensed ring is C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 fused aromatic ring), fused heteroaromatic ring having 5 to 60 members (specifically, fused heteroaromatic ring having 5 to 30 members), C3 to C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0206] In chemical formula 1 according to the present invention, c is an integer from 0 to 4, specifically an integer from 0 to 2, and d is an integer from 0 to 3, specifically an integer from 0 to 2.

[0207] Here, when c is 0, it means that hydrogen is not substituted with the substituent R1, and when d is 0, it means that hydrogen is not substituted with the substituent R2. On the other hand, when c is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R1, and when d is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R2. At this time, a plurality of R1s are the same or different from each other, and a plurality of R2s are the same or different from each other.

[0208] R1 and R2 are the same or different, and each independently represent hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, and specifically, each independently comprises deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups.

[0209] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of R1 and R2 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other.

[0210] In one embodiment, R1 is the same as or different from Q1 and may be selected from the group consisting of hydrogen, deuterium (D), cyano group (-CN), and the substituents S1-1 to S1-44, but is not limited thereto.

[0211] In chemical formula 1 according to the present invention, n is an integer from 0 to 3, and can be specifically 0 or 1.

[0212] Here, when n is 0, it means that L1 is a single bond (direct bond). On the other hand, when n is an integer from 1 to 3, L1 is a divalent linker group, C1~C 20 alkylene group, C2~C 40 Alkenylene group, C6~C 30 Selected from the group consisting of an arylene group, a heteroarylene group having 5 to 30 nuclear atoms, and a divalent ether group (-O-), specifically C1~C 12 alkylene group, C2~C 12 Alkenylene group, C6~C 18 It can be selected from the group consisting of an arylene group, a heteroarylene group having 5 to 18 nuclear atoms, and a divalent ether group (-O-). Here, multiple L1s may be the same or different from each other.

[0213] At this time, the alkylene group, alkenylene group, arylene group and heteroarylene group of the above L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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 of C1~C40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other.

[0214] In one embodiment, the L1 may be a single bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a fluorene group, a divalent ether group (-O-), and a combination thereof. Here, the phenylene group, the biphenylene group, the terphenylene group, the naphthalene group, the phenanthrene group, the triphenylene group, and the fluorene group may be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 10 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0215] In another example, L1 may be, but is not limited to, a single bond, a divalent ether group (-O-), or a linker group represented by the following chemical formula L. In this case, multiple L1s are the same or different.

[0216] [chemical formula L]

[0217]

[0218] In the above chemical formula L,

[0219] h is an integer from 0 to 4,

[0220] Multiple R's are the same or different from each other,

[0221] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups (e.g., RR) to form a condensed ring, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups.

[0222] Depending on the binding position of L1 described above, it may be a compound represented by any one of the following chemical formulas 27 to 38 represented by chemical formula 1 according to the present invention, but is not limited thereto.

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] In the above chemical formulas 27 to 38,

[0236] Rings Cy2, Q1, b, c, d, R1, R2, Ar2, n and L1 are each as defined in the above chemical formula 1,

[0237] X1 to X5 are the same or different from each other, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different from each other;

[0238] Ar3 is hydrogen, deuterium (D), halogen (e.g. -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), 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, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., Ar3-Ar3) to form a condensed ring, each independently selected from deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 is selected from the group consisting of arylamine groups, or can form a condensed ring by condensation with an adjacent group (e.g., Ar3-Ar3, etc.);

[0239] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they are the same or different from each other. Here, the condensed ring is C3~C60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 fused aromatic ring), fused heteroaromatic ring having 5 to 60 members (specifically, fused heteroaromatic ring having 5 to 30 members), C3 to C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0240] The compound represented by chemical formula 1 according to the present invention may be a compound represented by any one of the following chemical formulas 39 to 50, depending on the types of rings Cy1 and Cy2, the bonding position between the benzene ring to which Q1 is bonded and its adjacent benzene ring, and the type and bonding position of L1, but is not limited thereto.

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253] In the above chemical formulas 39 to 50,

[0254] Rings Cy2, Q1, c, d, R1, R2, and n are each as defined in the above chemical formula 1,

[0255] A plurality of X1~X5-containing ring moieties are the same or different from each other, and X1 to X5 in each X1~X5-containing ring moiety are the same or different from each other, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different from each other,

[0256] Ar3 is as defined in the above chemical formulas 27 to 38.

[0257] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 180 below, but is not limited thereto.

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264] In the present invention, the "number of nuclear atoms" refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, P, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0265] 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.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] 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, preferably 1 to 3 carbons in the ring, 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. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0270] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 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.

[0271] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0272] 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 such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0273] 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.

[0274] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl.

[0275] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0276] In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboron group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0277] In the present invention, “alkylphosphinyl group” means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.

[0278] In addition, in the present invention, “arylphosphinyl group” means a phosphine group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0279] In the present invention, “arylphosphine oxide group” means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0280] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamine.

[0281] In the present invention, the "condensed ring" is a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclear atoms, a condensed heteroaromatic ring having 5 to 60 nuclear atoms, C3~C 60 It means a spyro ring or a combination thereof. Here, the nuclear atomic number means the number of atoms forming the ring, i.e. the number of ring atoms.

[0282]

[0283] Organic electroluminescent devices

[0284] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0285] Specifically, the organic electroluminescent device according to the present invention includes an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, as illustrated in FIGS. 1 to 3, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

[0286] The organic layer (300) of one or more layers may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport auxiliary layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layers (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be at least one of an electron transport layer (340) and an electron transport auxiliary layer (360).

[0287] According to an example, the organic material layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound of the above chemical formula 1, and can also move quickly from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0288] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0289] In the present invention, 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 the electron transport material that can be used include an oxazole compound, an isoxazole compound, a triazole compound, an isothiazole compound, an oxadiazole compound, a thiadiazole compound, a perylene compound, and an aluminum complex (e.g., Alq). 3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or in combination of two or more.

[0290] 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.

[0291] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound of the chemical formula 1 has a high triplet energy. Therefore, when the compound of the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer 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 of the device can be efficiently increased.

[0292] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer auxiliary layer material known in the art.

[0293] In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and heterocyclic derivatives containing nitrogen, but is not limited thereto.

[0294] The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 to 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0295] According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer (350) may be positioned between the electron transport layer (340) and the cathode (200). In addition, an electron transport auxiliary layer (360) may be positioned between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0296] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the light-emitting layer (330), the electron transport layer (340), or the electron transport auxiliary layer (360)] includes a compound represented by the chemical formula 1.

[0297] 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.

[0298] The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0299] Examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, 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.

[0300] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0301] In addition, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and conventional materials known in the art can be used.

[0302]

[0303] 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.

[0304] [Synthesis Example 1] Synthesis of Compound 1

[0305]

[0306] 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (5.10 g, 10 mmol), 4-(4-bromophenyl)-2,6-diphenylpyrimidine (3.87 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100 ℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 1 (2.83 g, yield 41%) was obtained using column chromatography.

[0307] Mass: [(M+H) + ] : 690

[0308]

[0309] [Synthesis Example 2] Synthesis of Compound 2

[0310]

[0311] 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (5.10 g, 10 mmol), 4-(5-chloro-[1,1'-biphenyl]-2-yl)-2,6-diphenylpyrimidine (4.18 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 2 (3.22 g, yield 42%) was obtained using column chromatography.

[0312] Mass: [(M+H) + ] : 766

[0313]

[0314] [Synthesis Example 3] Synthesis of Compound 3

[0315] <Step 1> Synthesis of 2-(5-chloro-[1,1'-biphenyl]-2-yl)-3,5,6-triphenylpyrazine

[0316]

[0317] 2-Bromo-3,5,6-triphenylpyrazine (3.87 g, 10 mmol), (5-chloro-[1,1'-biphenyl]-2-yl)boronic acid (2.32 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, the compound 2-(5-chloro-[1,1'-biphenyl]-2-yl)-3,5,6-triphenylpyrazine (2.12 g, yield 43%) was obtained using column chromatography.

[0318] Mass: [(M+H) + ] : 495

[0319] <Step 2> Synthesis of compound 3

[0320]

[0321] 2-(5-chloro-[1,1'-biphenyl]-2-yl)-3,5,6-triphenylpyrazine (4.95 g, 10 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (4.33 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 3 (3.29 g, yield 43%) was obtained using column chromatography.

[0322] Mass: [(M+H) + ] : 765

[0323]

[0324] [Synthesis Example 4] Synthesis of Compound 4

[0325] <Step 1> Synthesis of 4-([1,1'-biphenyl]-4-yl)-6-(4-chloro-2-(naphthalen-2-yl)phenyl)-2-phenylpyrimidine

[0326]

[0327] 4-([1,1'-biphenyl]-4-yl)-6-(2-bromo-4-chlorophenyl)-2-phenylpyrimidine (4.97 g, 10 mmol), naphthalen-2-ylboronic acid (1.71 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-([1,1'-biphenyl]-4-yl)-6-(4-chloro-2-(naphthalen-2-yl)phenyl)-2-phenylpyrimidine (2.39 g, yield 44%) was obtained using column chromatography.

[0328] Mass: [(M+H) + ] : 545

[0329] <Step 2> Synthesis of 4-([1,1'-biphenyl]-4-yl)-6-(2-(naphthalen-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-phenylpyrimidine

[0330]

[0331] 4-([1,1'-biphenyl]-4-yl)-6-(4-chloro-2-(naphthalen-2-yl)phenyl)-2-phenylpyrimidine (5.45 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (5.07 g, 20 mmol), Pd(dppf)Cl2 (0.36 g, 0.5 mmol), X-Phos (0.47 g, 1 mmol), KOAc (1.96 g, 20 mmol) were added to 100 ml of 1,4-Dioxane and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-([1,1'-biphenyl]-4-yl)-6-(2-(naphthalen-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-phenylpyrimidine (2.80 g, yield 44%) was obtained using column chromatography.

[0332] Mass: [(M+H) + ] : 636

[0333] <Step 3> Synthesis of compound 4

[0334]

[0335] 4-([1,1'-biphenyl]-4-yl)-6-(2-(naphthalen-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-phenylpyrimidine (6.36 g, 10 mmol), 4-(4-bromophenyl-2,3,5,6-d4)-2,6-diphenylpyrimidine (3.91 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 4 (3.61 g, yield 44%) was obtained using column chromatography.

[0336] Mass: [(M+H) + ] : 821

[0337]

[0338] [Synthesis Example 5] Synthesis of Compound 5

[0339] <Step 1> Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(5-chloro-2-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenylpyrimidine

[0340]

[0341] 2-([1,1'-biphenyl]-4-yl)-4-(2-bromo-5-chlorophenyl)-6-phenylpyrimidine (4.97 g, 10 mmol), dibenzo[b,d]furan-4-ylboronic acid (2.12 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 2-([1,1'-biphenyl]-4-yl)-4-(5-chloro-2-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenylpyrimidine (2.63 g, yield 45%) was obtained using column chromatography.

[0342] Mass: [(M+H) + ] : 585

[0343] <Step 2> Synthesis of compound 5

[0344]

[0345] 2-([1,1'-biphenyl]-4-yl)-4-(5-chloro-2-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenylpyrimidine (5.85 g, 10 mmol), 2,6-diphenyl-4-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)pyridine (5.09 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 5 (4.19 g, yield 45%) was obtained using column chromatography.

[0346] Mass: [(M+H) + ] : 932

[0347]

[0348] [Synthesis Example 6] Synthesis of Compound 6

[0349]

[0350] 4-([1,1'-biphenyl]-2-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-2-yl)pyrimidine (6.62 g, 10 mmol), 2-(3-bromophenyl)-4,6-bis(3,4,5-trimethylphenyl)pyrimidine (4.71 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 6 (4.26 g, yield 46%) was obtained using column chromatography.

[0351] Mass: [(M+H) + ] : 927

[0352]

[0353] [Synthesis Example 7] Synthesis of Compound 7

[0354] <Step 1> Synthesis of 2'-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-4'-chloro-[1,1'-biphenyl]-4-carbonitrile

[0355]

[0356] 4-([1,1'-biphenyl]-3-yl)-6-(2-bromo-5-chlorophenyl)-2-phenylpyrimidine (4.97 g, 10 mmol), (4-cyanophenyl)boronic acid (1.46 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 2'-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-4'-chloro-[1,1'-biphenyl]-4-carbonitrile (2.44 g, yield 47%) was obtained using column chromatography.

[0357] Mass: [(M+H) + ] : 520

[0358] <Step 2> Synthesis of compound 7

[0359]

[0360] 2'-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-4'-chloro-[1,1'-biphenyl]-4-carbonitrile (5.20 g, 10 mmol), 4,6-di([1,1'-biphenyl]-2-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (5.86 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 7 (4.43 g, yield 47%) was obtained using column chromatography.

[0361] Mass: [(M+H) + ] : 944

[0362]

[0363] [Synthesis Example 8] Synthesis of Compound 8

[0364]

[0365] 4-(5-chloro-2-(pyridin-3-yl)phenyl)-2,6-diphenylpyrimidine (4.19 g, 10 mmol), (4-(6-phenylpyridazin-3-yl)phenyl)boronic acid (2.76 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 8 (2.95 g, yield 48%) was obtained using column chromatography.

[0366] Mass: [(M+H) + ] : 615

[0367]

[0368] [Synthesis Example 9] Synthesis of Compound 9

[0369] <Step 1> Synthesis of 4-(2,4-dichlorophenyl)-2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-6-phenylpyridine

[0370]

[0371] 2-(4-bromophenyl)-4-(2,4-dichlorophenyl)-6-phenylpyridine (4.55 g, 10 mmol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.38 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-(2,4-dichlorophenyl)-2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-6-phenylpyridine (2.78 g, yield 49%) was obtained using column chromatography.

[0372] Mass: [(M+H) + ] : 568

[0373] <Step 2> Synthesis of compound 9

[0374]

[0375] 4-(2,4-dichlorophenyl)-2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-6-phenylpyridine (5.68 g, 10 mmol), (4-(pyridin-2-yl)phenyl)boronic acid (3.98 g, 20 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 9 (3.94 g, yield 49%) was obtained using column chromatography.

[0376] Mass: [(M+H) + ] : 806

[0377]

[0378] [Synthesis Example 10] Synthesis of Compound 10

[0379] <Step 1> Synthesis of 4-(4'-chloro-3'-(2-phenyl-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-2-phenylbenzofuro[3,2-d]pyrimidine

[0380]

[0381] 4-(5-bromo-2-chlorophenyl)-2-phenyl-6-(4-(trifluoromethyl)phenyl)pyrimidine (4.89 g, 10 mmol), (2-(2-phenylbenzofuro[3,2-d]pyrimidin-4-yl)phenyl)boronic acid (3.66 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-(4'-chloro-3'-(2-phenyl-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-2-phenylbenzofuro[3,2-d]pyrimidine (3.65 g, yield 50%) was obtained using column chromatography.

[0382] Mass: [(M+H) + ] : 731

[0383] <Step 2> Synthesis of compound 10

[0384]

[0385] 4-(4'-chloro-3'-(2-phenyl-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-2-phenylbenzofuro[3,2-d]pyrimidine (7.31 g, 10 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid (2.87 g, 20 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 10 (4.69 g, yield 50%) was obtained using column chromatography.

[0386] Mass: [(M+H) + ] : 938

[0387]

[0388] [Synthesis Example 11] Synthesis of Compound 11

[0389]

[0390] 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (5.10 g, 10 mmol), 4-(3-bromophenyl)-2,6-diphenylpyrimidine (3.87 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 11 (2.83 g, yield 41%) was obtained using column chromatography.

[0391] Mass: [(M+H) + ] : 690

[0392]

[0393] [Synthesis Example 12] Synthesis of Compound 12

[0394]

[0395] 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (5.10 g, 10 mmol), 4-(4-chloro-[1,1'-biphenyl]-2-yl)-2,6-diphenylpyrimidine (4.18 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 12 (3.22 g, yield 42%) was obtained using column chromatography.

[0396] Mass: [(M+H) + ] : 766

[0397]

[0398] [Synthesis Example 13] Synthesis of Compound 13

[0399]

[0400] 4-([1,1'-biphenyl]-4-yl)-2-(4-chloro-[1,1'-biphenyl]-2-yl)-6-(dibenzo[b,d]furan-3-yl)pyrimidine (5.85 g, 10 mmol), (3-(4-phenylquinazolin-2-yl)phenyl)boronic acid (3.26 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 13 (3.57 g, yield 43%) was obtained using column chromatography.

[0401] Mass: [(M+H) + ] : 830

[0402]

[0403] [Synthesis Example 14] Synthesis of Compound 14

[0404] <Step 1> Synthesis of 4-(2-bromo-6-chlorophenyl)-2,6-diphenylpyrimidine

[0405]

[0406] 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10 mmol), (2-bromo-6-chlorophenyl)boronic acid (2.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, the compound 4-(2-bromo-6-chlorophenyl)-2,6-diphenylpyrimidine (1.85 g, yield 44%) was obtained using column chromatography.

[0407] Mass: [(M+H) + ] : 421

[0408] <Step 2> Synthesis of 4-(2-chloro-6-(spiro[fluorene-9,9'-xanthen]-2-yl)phenyl)-2,6-diphenylpyrimidine

[0409]

[0410] 4-(2-bromo-6-chlorophenyl)-2,6-diphenylpyrimidine (4.21 g, 10 mmol), spiro[fluorene-9,9'-xanthen]-2-ylboronic acid (3.76 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-(2-chloro-6-(spiro[fluorene-9,9'-xanthen]-2-yl)phenyl)-2,6-diphenylpyrimidine (2.96 g, yield 44%) was obtained using column chromatography.

[0411] Mass: [(M+H) + ] : 673

[0412] <Step 3> Synthesis of compound 14

[0413]

[0414] 4-(2-chloro-6-(spiro[fluorene-9,9'-xanthen]-2-yl)phenyl)-2,6-diphenylpyrimidine (6.73 g, 10 mmol), (4-(1,10-phenanthrolin-2-yl)phenyl)boronic acid (3.00 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound 14 (3.92 g, yield 44%) was obtained using column chromatography.

[0415] Mass: [(M+H) + ] : 893

[0416]

[0417] [Synthesis Example 15] Synthesis of Compound 15

[0418] <Step 1> Synthesis of 2-(4-(2-bromo-3-chlorophenyl)pyridin-2-yl)-4,6-diphenyl-1,3,5-triazine

[0419]

[0420] 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine (3.89 g, 10 mmol), (2-bromo-3-chlorophenyl)boronic acid (2.35 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 2-(4-(2-bromo-3-chlorophenyl)pyridin-2-yl)-4,6-diphenyl-1,3,5-triazine (2.24 g, yield 45%) was obtained using column chromatography.

[0421] Mass: [(M+H) + ] : 499

[0422] <Step 2> Synthesis of 2-(2'-chloro-6'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)pyridin-4-yl)-[1,1'-biphenyl]-3-yl)-1-phenyl-1H-benzo[d]imidazole

[0423]

[0424] 2-(4-(2-bromo-3-chlorophenyl)pyridin-2-yl)-4,6-diphenyl-1,3,5-triazine (4.99 g, 10 mmol), (3-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid (3.14 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 2-(2'-chloro-6'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)pyridin-4-yl)-[1,1'-biphenyl]-3-yl)-1-phenyl-1H-benzo[d]imidazole (3.10 g, yield 45%) was obtained using column chromatography.

[0425] Mass: [(M+H) + ] : 689

[0426] <Step 3> Synthesis of compound 15

[0427]

[0428] 2-(2'-chloro-6'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)pyridin-4-yl)-[1,1'-biphenyl]-3-yl)-1-phenyl-1H-benzo[d]imidazole (6.89 g, 10 mmol), 4-([1,1'-biphenyl]-4-yl)-6-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (5.86 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol) and Cs2CO3 (6.51 g, 20 mmol) in 1,4-Dioxane 100. The mixture was added to 25 ml of H2O and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 15 (5.01 g, yield 45%) was obtained using column chromatography.

[0429] Mass: [(M+H) + ] : 1113

[0430]

[0431] [Synthesis Example 16] Synthesis of Compound 16

[0432] <Step 1> Synthesis of 4-(4'-chloro-3'-(2-phenyl-6-(4-(pyridin-2-yl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-2,6-di(naphthalen-1-yl)pyridine-3,5-dicarbonitrile

[0433]

[0434] 4-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-phenyl-6-(4-(pyridin-2-yl)phenyl)pyrimidine (5.45 g, 10 mmol), 4-(4-bromophenyl)-2,6-di(naphthalen-1-yl)pyridine-3,5-dicarbonitrile (5.36 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-(4'-chloro-3'-(2-phenyl-6-(4-(pyridin-2-yl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-2,6-di(naphthalen-1-yl)pyridine-3,5-dicarbonitrile (4.02 g, yield 46%) was obtained using column chromatography.

[0435] Mass: [(M+H) + ] : 875

[0436] <Step 2> Synthesis of compound 16

[0437]

[0438] 4-(4'-chloro-3'-(2-phenyl-6-(4-(pyridin-2-yl)phenyl)pyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-2,6-di(naphthalen-1-yl)pyridine-3,5-dicarbonitrile (8.75 g, 10 mmol), benzofuro[3,2-b]pyridin-3-ylboronic acid (2.13 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 16 (4.63 g, yield 46%) was obtained using column chromatography.

[0439] Mass: [(M+H) + ] : 1008

[0440]

[0441] [Synthesis Example 17] Synthesis of Compound 17

[0442] <Step 1> Synthesis of 3-(4'-chloro-3'-(6-phenylpyridin-3-yl)-[1,1'-biphenyl]-2-yl)-2,6-dimethylpyridine

[0443]

[0444] 5-(5-bromo-2-chlorophenyl)-2-phenylpyridine (3.44 g, 10 mmol), (2-(2,6-dimethylpyridin-3-yl)phenyl)boronic acid (2.27 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 3-(4'-chloro-3'-(6-phenylpyridin-3-yl)-[1,1'-biphenyl]-2-yl)-2,6-dimethylpyridine (2.10 g, yield 47%) was obtained using column chromatography.

[0445] Mass: [(M+H) + ] : 446

[0446] <Step 2> Synthesis of compound 17

[0447]

[0448] 3-(4'-chloro-3'-(6-phenylpyridin-3-yl)-[1,1'-biphenyl]-2-yl)-2,6-dimethylpyridine (4.46 g, 10 mmol), triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 17 (3.51 g, yield 47%) was obtained using column chromatography.

[0449] Mass: [(M+H) + ] : 747

[0450]

[0451] [Synthesis Example 18] Synthesis of Compound 18

[0452] <Step 1> Synthesis of (4'-(4-(3-chlorophenyl)-[2,2'-bipyridin]-6-yl)-[1,1'-biphenyl]-4-yl)diphenylphosphine oxide

[0453]

[0454] 6-(4-bromophenyl)-4-(3-chlorophenyl)-2,2'-bipyridine (4.21 g, 10 mmol), (4-(diphenylphosphoryl)phenyl)boronic acid (3.22 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound (4'-(4-(3-chlorophenyl)-[2,2'-bipyridin]-6-yl)-[1,1'-biphenyl]-4-yl)diphenylphosphine oxide (2.97 g, yield 48%) was obtained using column chromatography.

[0455] Mass: [(M+H) + ] : 619

[0456] <Step 2> Synthesis of compound 18

[0457]

[0458] (4'-(4-(3-chlorophenyl)-[2,2'-bipyridin]-6-yl)-[1,1'-biphenyl]-4-yl)diphenylphosphine oxide (6.19 g, 10 mmol), phenyl(2'-(pyridin-2-yl)-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)methanone (4.61 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 18 (4.40 g, yield 48%) was obtained using column chromatography.

[0459] Mass: [(M+H) + ] : 918

[0460]

[0461] [Synthesis Example 19] Synthesis of Compound 19

[0462] <Step 1> Synthesis of 3'-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)-4'-chloro-N,N-diphenyl-[1,1'-biphenyl]-4-amine

[0463]

[0464] 2-([1,1'-biphenyl]-3-yl)-4-(5-bromo-2-chlorophenyl)-6-phenylpyrimidine (4.97 g, 10 mmol), (4-(diphenylamino)phenyl)boronic acid (2.89 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 3'-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)-4'-chloro-N,N-diphenyl-[1,1'-biphenyl]-4-amine (3.24 g, yield 49%) was obtained using column chromatography.

[0465] Mass: [(M+H) + ] : 662

[0466] <Step 2> Synthesis of compound 19

[0467]

[0468] 3'-(2-([1,1'-biphenyl]-3-yl)-6-phenylpyrimidin-4-yl)-4'-chloro-N,N-diphenyl-[1,1'-biphenyl]-4-amine (6.62 g, 10 mmol), 4-(benzo[b]naphtho[1,2-d]thiophen-9-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)pyrimidine (6.66 g, 10 mmol), Pd(OAc)2(0.22 g, 1 mmol), It was added to 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 19 (5.71 g, yield 49%) was obtained using column chromatography.

[0469] Mass: [(M+H) + ] : 1166

[0470]

[0471] [Synthesis Example 20] Synthesis of Compound 20

[0472] <Step 1> Synthesis of 5-(3'-chloro-4'-(5-(dibenzo[b,e][1,4]dioxin-2-yl)-6-phenylpyridin-2-yl)-[1,1'-biphenyl]-4-yl)pyrazine-2,3-dicarbonitrile

[0473]

[0474] 6-(4-bromo-2-chlorophenyl)-3-(dibenzo[b,e][1,4]dioxin-2-yl)-2-phenylpyridine (5.26 g, 10 mmol), (4-(5,6-dicyanopyrazin-2-yl)phenyl)boronic acid (2.50 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 5-(3'-chloro-4'-(5-(dibenzo[b,e][1,4]dioxin-2-yl)-6-phenylpyridin-2-yl)-[1,1'-biphenyl]-4-yl)pyrazine-2,3-dicarbonitrile (3.26 g, yield 50%) was obtained using column chromatography.

[0475] Mass: [(M+H) + ] : 652

[0476] <Step 2> Synthesis of compound 20

[0477]

[0478] 5-(3'-chloro-4'-(5-(dibenzo[b,e][1,4]dioxin-2-yl)-6-phenylpyridin-2-yl)-[1,1'-biphenyl]-4-yl)pyrazine-2,3-dicarbonitrile (6.52 g, 10 mmol), (5,5-dioxidodibenzo[b,d]thiophen-3-yl)boronic acid (2.60 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), X-Phos (0.95 g, 2 mmol), Cs2CO3 (6.51 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound 20 (4.15 g, yield 50%) was obtained using column chromatography.

[0479] Mass: [(M+H) + ] : 831

[0480]

[0481] [Example 1] Fabrication of a blue organic electroluminescent device

[0482] Compound 1 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 according to the following process.

[0483] 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.

[0484] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / compound 1 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used are as follows.

[0485]

[0486]

[0487] [Examples 2 to 20] Preparation of blue organic electroluminescent devices

[0488] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 used as an electron transport auxiliary layer material in Example 1.

[0489]

[0490] [Comparative Examples 1 to 3] Manufacturing of blue organic electroluminescent devices

[0491] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds HB1, HB2, and HB3 were used instead of the compound 1 used as the electron transport auxiliary layer material in Example 1. At this time, the structures of HB1, HB2, and HB3 used are as follows.

[0492]

[0493]

[0494] [Evaluation Example 1]

[0495] For the organic electroluminescent devices manufactured in Examples 1 to 20 and Comparative Examples 1 to 3, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0496] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 14.0 45 47.9 Example 2 24.7 45 76.5 Example 3 34.0 45 5 6.9 Example 4 44.1 45 6 6.8 Example 5 54.2 45 76.6 Example 6 64.3 45 8 6.6 Example 7 74.5 45 5 7.8 Example 8 85.0 45 6 7.5 Example 9 95.0 45 8 7.2 Example 10 10 4.8 45 36.1 Example 11 ... 14144.54546.6Embodiment 15154.94577.0Embodiment 16164.14567.2Embodiment 17174.34526.4Embodiment 18184.54577.6Embodiment 19194.74596.0Embodiment 20204.94586.1Comparative Example 1HB15.14585.8Comparative Example 2HB25.34555.2Comparative Example 3HB35.44525.1

[0497] From the above Table 1, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 20 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 1 to 3, respectively.

[0498]

[0499] [Example 21] Fabrication of a blue organic electroluminescent device

[0500] Compound 1 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 according to the following process.

[0501] 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.

[0502] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / HB (5 nm) / compound 1 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, HB, and Liq used are as follows, respectively.

[0503]

[0504]

[0505] [Examples 21 to 40] Preparation of blue organic electroluminescent devices

[0506] A blue organic electroluminescent device was manufactured in the same manner as in Example 21, except that the compounds shown in Table 2 below were used instead of Compound 1 used as an electron transport layer material in Example 21.

[0507]

[0508] [Comparative Examples 4 to 6] Manufacturing of blue organic electroluminescent devices

[0509] A blue organic electroluminescent device was manufactured in the same manner as in Example 21, except that compounds ET1, ET2, and ET3 were used instead of compound 1 used as an electron transport layer material in Example 21. The structures of ET1, ET2, and ET3 used here are as follows.

[0510]

[0511]

[0512] [Evaluation Example 2]

[0513] For the organic electroluminescent devices manufactured in Examples 21 to 40 and Comparative Examples 4 to 6, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0514] Sample Electron Transport Layer Material Driving Voltage (V) Peak Luminescence (nm) Current Efficiency (cd / A) Example 2114.14557.2 Example 2224.24577.4 Example 2334.84526.5 Example 2444.74536.8 Example 2554.64556.9 Example 2664.64566.8 Example 2774.44557.1 Example 2885.14527.4 Example 2995.04597.4 Example 30105.04596.9 Example 31114.74556.9 Example 32124.14586.2 Example 33134.44537.0 Example 34144.94526.8 Example 35154.94546.5 Example 36164.14567.3 Example 37174.04546.3 Example 38184.44587.8 Example 39194.94556.5 Example 40205.14577.1 Comparative Example 4ET15.24575.9 Comparative Example 5ET25.44505.4 Comparative Example 6ET35.54525.5

[0515] From Table 2 above, it was confirmed that the organic light-emitting devices manufactured in Examples 21 to 40 were superior to the driving voltage, light emission peak, and current efficiency of the organic light-emitting devices manufactured in Comparative Examples 4 to 6, respectively.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, Rings Cy1 and Cy2 are the same or different from each other and are each independently selected from the group consisting of a 6-membered monocyclic heteroaromatic ring containing 1 to 2 nitrogens and a 9 to 30-membered polycyclic heteroaromatic ring containing 1 to 4 nitrogens, a and b are each integers from 0 to 4, Ar1 and Ar2 are the same or different from each other and are hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, Q1 is deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, c is an integer from 0 to 4, d is an integer from 0 to 3, R1 and R2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, n is an integer from 0 to 3, L1 is a single bond, or C1~C 20 Alkylene group, C2~C 40 Alkenylene group, C6~C 30 is selected from the group consisting of an arylene group, a heteroarylene group having 5 to 30 nuclear atoms, and a divalent ether group (-O-), The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1, Ar2, Q1, R1 and R2, and the alkylene group, alkenylene group, arylene group and heteroarylene group of the above L1 are each independently selected from deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

2. In paragraph 1, Above and The compound wherein the moieties are identical or different and are each independently a moiety represented by one of the following chemical formulas H1 to H5: [Chemical formula H1] [chemical formula H2] [chemical formula H3] [Chemical formula H4] [Chemical formula H5] (In the above chemical formulas H1 to H5, X1 to X5 are the same or different, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different; X6 to X9 are the same or different, and are each independently selected from the group consisting of N or C(Ar4), provided that at least one of X6 to X9 is N, wherein one carbon among C(Ar4) other than N can be connected to the chemical formula 1, and a plurality of C(Ar4) are the same or different; X 10 Inland X 13 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 Inland X 13 At least one of them is N, wherein the plurality of C(Ar5) are the same or different; Y1 is O, S or C(Ar6)(Ar7), X 14 Inland X 17 are identical or different from each other, and each is independently N or C(Ar8), and only X 14 Inland X 17 At least one of them is N, wherein the plurality of C(Ar8) are the same or different; X 18 Inland X 21 are identical or different from each other, and each is independently N or C(Ar9), and only X 18 Inland X 21 At least one of them is N, wherein the plurality of C(Ar9) are the same or different; e is an integer from 0 to 3, f is an integer from 0 to 7, Ar3 to Ar9 and R are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 to Ar9 and R are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

3. In paragraph 1, Above and A compound wherein the moieties are identical or different and are each independently selected from the group consisting of the following moieties Mo1-1 to Mo1-38: (In the above moiety Mo1-1, X1, X2, X3 and X5 are the same or different from each other and are each independently N or C(Ar3), wherein one or two of X1, X2, X3 and X5 are N, In the above moiety Mo1-2, X1 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1 and X5 are N, In the above moieties Mo1-3, X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X2 and X5 are N, In the above moieties Mo1-4, Mo1-8 and Mo1-12, X1, X4 and X5 are the same or different from each other and are each independently N or C(Ar3), wherein one or two of X1, X4 and X5 are N, In the above moieties Mo1-5, Mo1-9 and Mo1-13, X1, X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X2 and X5 are N, In the above moieties Mo1-6, Mo1-7, Mo1-10, Mo1-11, Mo1-14 and Mo1-15, X3, X4 and X5 are the same or different and are each independently N or C(Ar3), wherein one or two of X3, X4 and X5 are N, In the above moieties Mo1-2, Mo1-3, Mo1-8 to Mo1-11, Ring Cy3 is C6~C 30 is a condensed aromatic ring, In the above moieties Mo1-4 to Mo1-11, Z1 is selected from the group consisting of O, S, C(R3)(R4) and oxo group (=O), In the above moieties Mo1-12 to Mo1-15, Z2 is selected from the group consisting of O, S, C(R5)(R6) and oxo group (=O), In the above moiety Mo1-16, X1, X2 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X2 and X5 are N, In the above moiety Mo1-17, X1, X4 and X5 are the same or different from each other, and are each independently N or C(Ar3), wherein one or two of X1, X4 and X5 are N, In the above moiety Mo1-18, X3, X4 and X5 are the same or different from each other and are each independently N or C(Ar3), wherein one or two of X3, X4 and X5 are N, In the above moieties Mo1-16 to Mo1-18, X 22 Inland X 25 are identical or different from each other, and each independently represents N or C(Ar 10 ) and at this time X 22 Inland X 25 At least one of them is N, In the above moieties Mo1-19, Mo1-22 and Mo1-24, X1, X2 and X3 are the same or different from each other, and are each independently N or C(Ar3), wherein one of X1, X2 and X3 is N, In the above moieties Mo1-20 and Mo1-23, X1, X2 and X5 are the same or different from each other and are each independently N or C(Ar3), wherein one of X1, X2 and X5 is N, In the above moiety Mo1-21, X1, X4 and X5 are the same or different from each other and are each independently N or C(Ar3), wherein one of X1, X4 and X5 is N, In the above moieties Mo1-23 and Mo1-24, X 26 Inland X 29 are identical or different from each other, and each independently represents N or C(Ar 11 ) and at this time X 26 Inland X 29 At least one of them is N, In the above moiety Mo1-25, X6, X7 and X9 are the same or different from each other and are each independently N or C(Ar4), wherein at least one of X6, X7 and X9 is N, In the above moieties Mo1-26, Mo1-28 and Mo1-29, X6, X8 and X9 are the same or different from each other and are each independently N or C(Ar4), wherein at least one of X6, X8 and X9 is N, In the above moiety Mo1-27, X7, X8 and X9 are the same or different from each other and are each independently N or C(Ar4), wherein at least one of X7, X8 and X9 is N, In the above moiety Mo1-29, X 30 Inland X 33 are identical or different from each other, and each independently represents N or C(Ar 12 ) and at this time X 30 Inland X 33 At least one of them is N, In the above moieties Mo1-30 and Mo1-31, X 10 and X 13 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 and X 13 At least one of them is N, In the above moiety Mo1-32, X 34 Inland X 41 are identical or different from each other, and each independently represents N or C(Ar 13 ) and, In the above moiety Mo1-33, X 10 and X 11 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 and X 11 At least one of them is N, In the above moieties Mo1-34 to Mo1-37, X 14 Inland X 17 are identical or different from each other, and each is independently N or C(Ar8), and only X 14 Inland X 17 At least one of them is N, In the above moiety Mo1-36, Ak1 and Ak2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, In the above moiety Mo1-37, Z3 is selected from the group consisting of O, S, C(R7)(R8) and oxo group (=O), In the above moiety Mo1-38, X 18 and X 21 are identical or different from each other, and each is independently N or C(Ar9), and only X 10 and X 11 At least one of them is N, d is an integer from 0 to 3, Ar3 to Ar 13 , R3 to R8 and R are the same or different from each other, are the same or different from each other, and are each independently hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with an adjacent group to form a condensed ring, The above Ar3 to Ar 13 , R3 to R8 and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of R are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

4. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 6: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] (In the above chemical formulas 2 to 6, Rings Cy2, Q1, b, c, d, R1, R2, Ar2, n and L1 are each as defined in Article 1, X1 to X5 are the same or different, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different; X6 to X9 are the same or different and are each independently selected from the group consisting of N or C(Ar4), provided that at least one of X6 to X9 is N, and wherein a plurality of C(Ar4)s are the same or different; X 10 Inland X 13 are identical or different from each other, and each is independently N or C(Ar5), and only X 10 Inland X 13 At least one of them is N, wherein the plurality of C(Ar5) are the same or different; Y1 is O, S or C(Ar6)(Ar7), X 14 Inland X 17 are identical or different from each other, and each is independently N or C(Ar8), and only X 14 Inland X 17 At least one of them is N, wherein the plurality of C(Ar8) are the same or different; X 18 Inland X 21 are identical or different from each other, and each is independently N or C(Ar9), and only X 18 Inland X 21 At least one of them is N, wherein the plurality of C(Ar9) are the same or different; e is an integer from 0 to 3, f is an integer from 0 to 7, Ar3 to Ar9 and R are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 to Ar9 and R are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

5. In paragraph 4, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 7 to 26: [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [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] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] (In the chemical formulas 7 to 26 above, Ring Cy2, Q1, b, c, d, R1, R2, Ar2, n, L1, X1 to X 21 , Y1, e, f, Ar3 to Ar9 and R are each as defined in Article 4).

6. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 27 to 38: [Chemical Formula 27] [Chemical formula 28] [Chemical Formula 29] [Chemical formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical formula 36] [Chemical Formula 37] [Chemical formula 38] (In the above chemical formulas 27 to 38, Rings Cy2, Q1, b, c, d, R1, R2, Ar2, n and L1 are each as defined in Article 1, X1 to X5 are the same or different, and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different; Ar3 is hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

7. In paragraph 1, Q1 is selected from the group consisting of deuterium (D), a cyano group (-CN), and the following substituents S1-1 to S1-44, A compound wherein R1 is the same as or different from Q1 and is independently selected from the group consisting of hydrogen, deuterium (D), a cyano group (-CN), and the following substituents S1-1 to S1-44: (In the above substituents S1-1 to S1-44, Y2, Y3, and Y4 are each independently O, S, C(R9)(R 10 ), N(R 11 ) and sulfonyl group (-S(=O)2-), A1 to A4 are identical or different from each other, and each independently represents N or C(R 12 ) and at least one of A1 to A4 is N, Y5 and Y6 are identical or different from each other, and are each independently O, S, C(R 13 )(R 14 ) and N(R 15 ) is selected from the group consisting of, Y7 is O, S, C(R 16 )(R 17 ) and N(R 18 ) is selected from the group consisting of, Ring Cy4 is present or absent, and when ring Cy4 is present, ring Cy4 is C6~C 18 is a condensation ring, g is an integer from 0 to 5, h is an integer from 0 to 4, i is an integer from 0 to 7, j is 0 or 1, k is an integer from 0 to 8, l is an integer from 0 to 6, m is an integer from 0 to 9, Multiple R's are identical or different from each other, R9 to R 18 and R are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring).

8. In paragraph 1, The compound wherein the above L1 is a single bond, or a divalent ether group (-O-) or a linker group represented by the following chemical formula L: [chemical formula L] (In the above chemical formula L, h is an integer from 0 to 4, Multiple R's are identical or different from each other, R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring).

9. In paragraph 1, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 39 to 50: [Chemical Formula 39] [Chemical formula 40] [Chemical Formula 41] [Chemical formula 42] [Chemical formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical formula 46] [Chemical Formula 47] [Chemical formula 48] [Chemical Formula 49] [Chemical formula 50] (In the above chemical formulas 39 to 50, Rings Cy2, Q1, c, d, R1, R2, and n are each as defined in Article 1, A plurality of X1 to X5-containing ring moieties are the same or different from each other, and X1 to X5 in each X1 to X5-containing ring moiety are the same or different from each other and are each independently N or C(Ar3), provided that at most two of X1 to X5 are N, and in this case, a plurality of C(Ar3) are the same or different from each other; Ar3 is hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar3 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

10. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 180 below: .

11. Anode; cathode; comprising at least one organic layer interposed between the anode and cathode, An organic electroluminescent device, wherein at least one of the organic layers of the above one or more layers comprises an organic compound as described in any one of claims 1 to 10.

12. In paragraph 11, An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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