Organic compound and organic electroluminescent element using same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent element using the same. The present invention relates to an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, light-emitting ability, and the like, and an organic electroluminescent element having improved characteristics such as light-emitting efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers.

Description

Technical Field

[0001] The present invention relates to a novel organic compound and an organic electroluminescent element using the same. More specifically, the present invention relates to an organic compound having excellent electron injection and transport capabilities, heat resistance, electrochemical stability, etc., and an organic electroluminescent element having improved characteristics such as luminous efficiency, driving voltage, and life by including the compound in one or more organic layers. Background Art

[0002] When a voltage is applied between two electrodes in an organic electroluminescent element (hereinafter referred to as an "organic EL element"), holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons transition to the ground state, light is emitted. The materials used in the organic layer can be categorized by their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0003] Luminescent materials can be categorized into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials for more natural colors, based on their luminescent color. Furthermore, a host / dopant system can be used as a luminescent material to increase luminous efficiency through increased color purity and energy transfer.

[0004] Dopant materials can be categorized as fluorescent dopants using organic substances and phosphorescent dopants using metal complexes containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically increase luminous efficiency by up to four times compared to fluorescence, research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Anthracene derivatives have been reported as materials for light-emitting layers. Among light-emitting layer materials, Ir-containing metal complexes such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which offer advantages in improving efficiency, have been used as blue, green, and red dopants, and 4,4-dicarbazolybiphenyl (CBP) has been used as a phosphorescent host material.

[0006] However, while conventional organic layer materials have advantages in terms of luminescence properties, they have low glass transition temperatures and very poor thermal stability, making them unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, there is a demand for the development of organic layer materials with superior performance. Summary of the Invention

[0007] Technical issues

[0008] The purpose of the present invention is to provide a novel compound having excellent electron injection and transport capabilities, heat resistance, electrochemical stability, etc., which can be used as an organic layer material of an organic electroluminescent element, specifically an electron transport layer material or an electron transport auxiliary layer material.

[0009] Another object of the present invention is to provide an organic electroluminescent device comprising the novel compound, which has low driving voltage, high luminous efficiency, excellent electrical stability, and improved life.

[0010] Solutions to Problems

[0011] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0012] [Chemical Formula 1]

[0013]

[0014] (In the above chemical formula 1,

[0015] X1 to X3 are the same as or different from each other and are each independently N or C(R4), but at least two of X1 to X3 are N,

[0016] R1 and R2 are the same or different and are independently selected from deuterium, halogen, cyano, nitro, amino, C3-C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 and a heteroaryl group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring,

[0017] Ar1 is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei,

[0018] n is an integer from 0 to 5,

[0019] L1 is a single bond or selected from C1 to C 60 Alkylene, C6~C 60 and heteroarylene groups having an atomic nucleus number of 5 to 60,

[0020] Y1 is selected from the group consisting of O, S, C(R5)(R6) and N(R7),

[0021] Y2 is a single bond or is selected from O, S, C(R8)(R9) and N(R 10 ),

[0022] a is an integer from 0 to 7,

[0023] R3 to R 10 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring,

[0024] The cycloalkyl, heterocycloalkyl, aryl, heteroaryl and condensed ring of the above R1 and R2, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine and heteroarylamine of the above Ar1, the alkylene, arylene and heteroarylene groups of the above L1, and the above R3 to R 10 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amine group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the above-mentioned substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other).

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

[0026] According to one example, the organic layer containing the compound may be at least one selected from the group consisting of an electron transport layer and an electron transport assisting layer.

[0027] Effects of the Invention

[0028] The compounds of the present invention exhibit excellent electron transport, heat resistance, carrier transport, and luminescence properties, and therefore can be used as organic layer materials in organic electroluminescent devices. In particular, when the compounds of the present invention are used as electron transport layer materials or electron transport auxiliary layer materials, organic electroluminescent devices can be produced that exhibit superior luminescence performance, low driving voltage, high efficiency, and long life compared to conventional materials. Furthermore, full-color display panels with improved performance and life can be manufactured.

[0029] The effects of the present invention are not limited to the above-exemplified contents, and this specification includes more various effects. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 This is a cross-sectional view schematically showing the organic electroluminescent element according to the first embodiment of the present invention.

[0031] Figure 2 This is a cross-sectional view schematically showing an organic electroluminescent element according to a second embodiment of the present invention.

[0032] Figure 3 This is a cross-sectional view schematically showing an organic electroluminescent element according to a third embodiment of the present invention.

[0033] <Description of symbols>

[0034] 100: anode, 200: cathode,

[0035] 300: organic layer, 310: hole injection layer,

[0036] 320: hole transport layer, 330: light emitting layer,

[0037] 340: electron transport layer, 350: electron injection layer,

[0038] 360: Electron transport auxiliary layer. DETAILED DESCRIPTION

[0039] Hereinafter, the present invention will be described.

[0040] <New Compounds>

[0041] The novel compound of the present invention is represented by the above chemical formula 1, in which the dibenzo part is directly or through a linking group bonded to the nitrogen-containing heteroaromatic ring, and a phenyl group is introduced (substituted) on the above nitrogen-containing heteroaromatic ring, and two substituents are introduced (substituted) on such a phenyl group, but based on the above nitrogen-containing heteroaromatic ring, the substituents are introduced into the meta position and the para position, respectively. Such a compound of the present invention has excellent thermal stability, carrier transport ability (e.g., electron transport ability) and luminescence ability, and can be used as an organic layer material capable of realizing the characteristics of an organic electroluminescent element, such as high efficiency, long life, and low driving voltage characteristics of the element, in particular an electron transport layer material or an electron transport auxiliary layer.

[0042] Generally, in an organic electroluminescent element, if the injection of electrons from the electron transport layer to the light-emitting layer becomes faster, the life of the element tends to be shortened. This is a phenomenon that occurs when the area where excitons are formed in the light-emitting layer is locally concentrated. In order to solve this problem, the electron injection rate must be adjusted. However, if the electron injection rate is simply slowed down, the efficiency of the blue organic electroluminescent element will decrease. Therefore, it is necessary to adjust the electron transport capacity to form excitons uniformly over the entire area of the light-emitting layer while keeping the injection rate of electrons injected into the light-emitting layer fast. To this end, the dibenzo part in the compound represented by Chemical Formula 1 of the present invention is combined directly or through a connecting group with the nitrogen-containing heteroaromatic ring. In addition, a phenyl group is introduced (substituted) on the above-mentioned nitrogen-containing heteroaromatic ring, and two substituents are introduced (substituted) on such a phenyl group, and the substituents are introduced (substituted) to the meta position and the para position respectively based on the above-mentioned nitrogen-containing heteroaromatic ring. That is, when the nitrogen-containing heteroaromatic ring is located at position 1 of the above-mentioned phenyl group, the above-mentioned two substituents are located at positions 3 and 4 of the above-mentioned phenyl group, respectively. In such a compound of the present invention, the above-mentioned dibenzo part is a fluorene part, a dibenzo-p-dioxin (oxanthrene) part, etc., which can improve the conductivity. In addition, the nitrogen-containing heteroaromatic ring is a 6-membered (member) heteroaromatic ring containing 2 or 3 nitrogen (N), including pyrimidine, triazine, etc. Such a nitrogen-containing heteroaromatic ring is an electron-withdrawing group (EWG) with strong electron-withdrawing properties, which can increase the electron migration speed and improve the electron transport capacity. In addition, since the 3rd and 4th positions of the phenyl group bound to the nitrogen-containing heteroaromatic ring are substituted by substituents, respectively, the stability of the molecule and the electron transport speed of the material can be improved. Therefore, the compound of the present invention has a LUMO energy that allows electrons to be easily injected into the light-emitting layer, and the electron transport capacity is improved due to the combination of the dibenzo part and the phenyl group substituted by two substituents, thereby achieving high efficiency and long life characteristics of the element compared to previous electron transport layer materials. In addition, the compound of the present invention is centered on a phenyl group that is combined with a nitrogen-containing heteroaromatic ring as an electron-withdrawing group (EWG) and introduces a substituent (e.g., an aryl group) in the para position, thereby extending the conjugation (conjugation) length of the molecule to improve the stability of the molecule. In addition, by introducing a substituent (e.g., an aryl group) in the meta position with the above-mentioned phenyl group as the center, the intermolecular length can be adjusted according to the aryl group, thereby easily adjusting the electron transfer speed. In addition, the compound of the present invention is excellent in chemical stability by combining a nitrogen-containing heteroaromatic ring as an electron-withdrawing group (EWG) with a benzene ring substituted with two substituents (e.g., terphenyl, etc.), and has excellent thermal stability due to a high glass transition temperature (Tg). Not only that, the compound of the present invention can have physicochemical properties that are more suitable for electron injection and electron transfer due to the nitrogen-containing heteroaromatic ring.

[0043] In addition, the compound represented by Chemical Formula 1 of the present invention has a triplet energy higher than that of the light-emitting layer, so that the excitons (exciton) generated in the light-emitting layer can be prevented from diffusing (migrating) to the adjacent electron transport layer or hole transport layer. Therefore, the compound of the present invention can increase the number of excitons that contribute to luminescence in the light-emitting layer to improve the luminous efficiency of the element, and can improve the durability and stability of the element to effectively extend the life of the element. In addition, the organic electroluminescent element using the compound of the present invention can achieve low voltage drive, thereby improving life.

[0044] As described above, when the compound represented by Chemical Formula 1 of the present invention is used as an organic layer material of an organic electroluminescent element, specifically as a light-emitting layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, a luminescent auxiliary layer material, an electron transport auxiliary layer material, a life-improving layer material, and more specifically as an electron transport layer material or an electron transport auxiliary layer material, the performance and life characteristics of the organic electroluminescent element can be greatly improved. Such an organic electroluminescent element can ultimately maximize the performance of a full-color organic light-emitting panel.

[0045] In the compound represented by Chemical Formula 1, X1 to X3 are identical or different and are each independently N or C(R4), but at least two of X1 to X3 are N. The ring containing X1 to X3 is a type of nitrogen (N)-containing heteroaromatic ring, and is a monocyclic heteroaryl group containing two or three nitrogen atoms (e.g., an azinyl group). Therefore, the compound of Chemical Formula 1 of the present invention can exhibit superior electron-withdrawing properties, facilitating electron injection and transport.

[0046] According to one example, the ring moiety containing X1 to X3 It can be selected from the group consisting of the following parts Az-1 to Az-3.

[0047]

[0048] In the above sections Az-1 to Az-3,

[0049] * refers to the part forming a bond with Chemical Formula 1,

[0050] Ar1, R1, R2 and R4 are each the same as defined in the above Chemical Formula 1.

[0051] The above R4 are the same or different and can be independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups with 5 to 60 atomic nuclei, or condensed with adjacent groups (R4-Ar1, R4-R1, R4-L1, etc.) to form a condensed ring, specifically, R4 can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aromatic groups, heteroaryl groups with 5 to 60 atomic nuclei, and C6~C 60 A group composed of arylamine groups.

[0052] In this case, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring of R4 can be independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60Arylamine, C6~C 60 The substituted or unsubstituted one or more substituents are selected from the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, or the above substituents are condensed with adjacent groups to form a condensed ring, specifically, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0053] In the compound represented by the above chemical formula 1, R1 and R2 are the same or different and are independently selected from deuterium (D), halogen, cyano (-CN), nitro, amino, C3-C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 A group consisting of an aromatic group with 5 to 60 atomic nuclei and a heteroaromatic group with 5 to 60 atomic nuclei, or a condensed ring formed by condensing with adjacent groups (for example, R1-R2, a benzene ring formed by combining R1 and R1, and a benzene ring formed by combining R2 and R2). 30 or a condensed heteroaromatic ring having 5 to 30 atomic nuclei containing one or more heteroatoms (e.g., N, O, S, Se, etc.).

[0054] In this case, the cycloalkyl, heterocycloalkyl, aryl, heteroaryl and condensed ring of R1 and R2 are each independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The substituted or unsubstituted one or more substituents (R) in the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, or condensed with adjacent groups (e.g., RR, R-R1, R-R2) to form a condensed ring, specifically, each independently selected from deuterium, halogen, cyano, C1 to C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The group consisting of arylamine groups may be substituted or unsubstituted with one or more substituents (R), or the above-mentioned substituents (R) are condensed with adjacent groups (for example: RR, R-R1) to form a condensed ring. When there are multiple substituents, they are the same or different from each other.

[0055] According to one example, R1 and R2 are the same or different and can be independently selected from C6 to C 30 A group consisting of an aryl group (for example, phenylene, biphenylene, terphenylene, naphthalene, anthracene, phenanthrene, etc.) and a heteroaryl group having 5 to 30 atomic nuclei (for example, pyridine, pyrimidine, triazine, dibenzofuran, dibenzothiophene, dibenzofuran, etc.), or a condensed ring formed by condensing with an adjacent group (for example, R1-R2, a benzene ring formed by combining R1 and R1, and a benzene ring formed by combining R2 and R2), wherein the aryl and heteroaryl groups of R1 and R2 are independently selected from deuterium, halogen, cyano, C1-C 20 Alkyl, C3~C 20 Cycloalkyl, heterocycloalkyl with 3 to 20 nuclei, C6~C 30 aryl, heteroaryl with 5 to 30 atomic nuclei, C1~C 20 Alkylsilyl, C6~C 30 Aryl silyl and C6~C 30 The group consisting of arylamine groups may be substituted or unsubstituted with one or more substituents (R), or the above-mentioned substituents (R) are condensed with adjacent groups (for example: RR, R-R1) to form a condensed ring. When there are multiple substituents, they are the same or different from each other.

[0056] Depending on R1 and R2, the compound represented by the above Chemical Formula 1 may be a compound represented by the following Chemical Formula 2 or 3. However, the present invention is not limited thereto.

[0057] [Chemical Formula 2]

[0058]

[0059] In the above chemical formulas 2 and 3,

[0060] X1 to X3, Ar1, n, L1, Y1, Y2, a and R3 are each the same as defined in the above Chemical Formula 1,

[0061] b1 and b2 are each an integer from 0 to 5,

[0062] X4 to X9 are the same or different from each other and are each independently N or C (R 17 ), but at least any one of X4 to X9 may be N; specifically, at least any one of X4 to X6 may be N, and the rest may be C (R 17 ), or at least one of X7 to X9 may be N, and the rest may be C(R 17 ),

[0063] R 11 to R 17 The same or different from each other, each independently can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or an adjacent group (for example: R 11 -R 11 、R 11 -R 12 、R 12 -R 12 、R 11 - adjacent benzene ring, R 12 - adjacent benzene ring, R 13 -R17 、R 14 -R 17 、R 15 -R 17 、R 16 -R 17 etc.) to form a condensed ring, specifically, each independently selected from deuterium, halogen, cyano, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aromatic groups, heteroaryl groups with 5 to 60 atomic nuclei, and C6~C 60 or with adjacent groups (e.g. R 11 -R 11 、R 11 -R 12 、R 12 -R 12 、R 11 - adjacent benzene ring, R 12 - adjacent benzene ring, R 13 -R 17 、R 14 -R 17 、R 15 -R 17 、R 16 -R 17 etc.) condense to form a condensed ring,

[0064] The above R 13 to R 17 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amine group is substituted or unsubstituted with one or more substituents (R) in the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, or the substituents (R) are substituted or unsubstituted with adjacent groups (e.g., RR, RR 13 , RR 14 , RR 15 , RR 16 etc.) to form a condensed ring, specifically, each independently selected from deuterium, halogen, cyano, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The arylamine group is composed of one or more substituents (R) substituted or unsubstituted, or the substituents (R) are combined with adjacent groups (for example: RR, RR 13 , RR 14 , RR 15 , RR 16 When there are multiple substituents, they may be the same as or different from each other.

[0065] According to one example, the above The part may be selected from the group consisting of the following parts Mo1-1 to Mo1-21, but is not limited thereto.

[0066]

[0067]

[0068]

[0069] In the above sections Mo1-1 to Mo1-21,

[0070] * refers to the part forming a bond with Chemical Formula 1,

[0071] c1 and c2 are each 0 or 1, but 1≤c1+c2≤2,

[0072] c3 and c4 are each an integer from 0 to 5, but 1≤c3+c4≤10,

[0073] c5 is an integer from 0 to 11,

[0074] c6 is an integer from 0 to 5,

[0075] c7 is an integer from 0 to 4,

[0076] c8 is an integer from 0 to 2,

[0077] c9 is an integer from 0 to 9,

[0078] c10 and c11 are each 0 or 1,

[0079] One or more R are the same or different and are independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei,

[0080] Z1 is O or S,

[0081] Z3 and Z4 are single bonds or O or S, but excluding the case where Z3 and Z4 are single bonds at the same time,

[0082] Z5 and Z6 are single bonds or O or S, but excluding the case where Z5 and Z6 are single bonds at the same time,

[0083] Z7 and Z8 are single bonds or O or S, but excluding the case where Z7 and Z8 are single bonds at the same time,

[0084] Ring Cy1 and ring Cy2 are the same or different and are each independently C6 to C 30 A condensed aromatic ring or a condensed heteroaromatic ring having 5 to 30 atomic nuclei,

[0085] X4 to X6 are the same or different from each other and are each independently N or C(R 17 ), but at least one of X4 to X6 is N,

[0086] X7 to X9 are the same as or different from each other and are each independently N or C(R 17 ), but at least one of X7 to X9 is N,

[0087] Z9 is O or S,

[0088] R 13 to R 17 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring,

[0089] The above R 13 to R 17 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The substituted or unsubstituted one or more substituents (R) selected from the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, or the above substituents (R) are condensed with adjacent groups to form a condensed ring, specifically, each independently selected from deuterium, halogen, cyano, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The arylamine group is substituted or unsubstituted with one or more substituents (R), or the substituents (R) are condensed with adjacent groups to form a condensed ring. When there are multiple substituents, they are the same or different.

[0090] According to another example, the above The moiety may be selected from the group consisting of the following moieties Mo2-1 to Mo2-61, but is not limited thereto.

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] In the above parts Mo2-1 to Mo2-61,

[0098] * refers to the part forming a bond with Chemical Formula 1,

[0099] d1 and d2 are each 0 or 1, but 1≤d1+d2≤2,

[0100] AK is C1~C 10The alkyl group may be selected from the group consisting of a methyl group, an ethyl group, a propyl group and a butyl group.

[0101] Ring Cy1 and ring Cy2 are each the same as defined in the above sections Mo1-1 to Mo1-21, specifically, they are the same as or different from each other, and each independently can be C6 to C 20 A condensed aromatic ring or a condensed heteroaromatic ring having 5 to 20 atomic nuclei.

[0102] The hydrogen of the above-mentioned parts Mo2-1 to Mo2-61 can be selected from deuterium (D), halogen, nitro, C1~C 12 Alkyl, C6~C 10 The aryl group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 10 atomic nuclei and a heteroaryl group having 5 to 10 atomic nuclei.

[0103] In the compound represented by the above chemical formula 1, Ar1 can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, specifically, can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aromatic groups, heteroaryl groups with 5 to 60 atomic nuclei, and C6~C 60 A group composed of arylamine groups.

[0104] In this case, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine and heteroarylamine groups of Ar1 can be independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The substituted or unsubstituted one or more substituents are selected from the group consisting of (aryl) (heteroaryl) amine groups and heteroarylamine groups having 5 to 60 atomic nuclei, or the above substituents are condensed with adjacent groups to form a condensed ring, specifically, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The group consisting of the arylamino groups may be substituted or unsubstituted by one or more substituents. When there are multiple substituents, they may be the same as or different from each other.

[0105] According to one example, the above Ar1 is C6~C 30 The aryl group of Ar1 can be selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C60 Aryl silyl and C6~C 60 The group consisting of the arylamino groups may be substituted or unsubstituted by one or more substituents. When there are multiple substituents, they may be the same as or different from each other.

[0106] According to another example, Ar1 can be selected from the group consisting of the following substituents S1 to S25. However, the present invention is not limited thereto.

[0107]

[0108]

[0109] In the above substituents S1 to S25,

[0110] * indicates a portion forming a bond with Chemical Formula 1.

[0111] The hydrogen of the above substituents S1 to S25 can be selected from deuterium (D), halogen, nitro, C1-C 12 Alkyl, C6~C 10 The aryl group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 10 atomic nuclei and a heteroaryl group having 5 to 10 atomic nuclei.

[0112] In the compound represented by the above Chemical Formula 1, n may be an integer from 0 to 5, specifically, an integer from 1 to 4.

[0113] When n is 0, L1 refers to a direct bond (single bond). On the other hand, when n is an integer from 1 to 5, L1 is a divalent linker group, which can be selected from C1 to C 60 Alkylene, C6~C 60 The group consisting of an arylene group and a heteroarylene group having an atomic nucleus number of 5 to 60, specifically, can be selected from C1 to C 18 Alkylene, C6~C 18 and a heteroarylene group having an atomic nucleus number of 5 to 18. Plural L1s may be the same as or different from each other.

[0114] The alkylene, arylene and heteroarylene groups of L1 are each independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl) amino group and a heteroaryl amino group having 5 to 60 atomic nuclei, or the above-mentioned substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0115] According to one example, one or more L1 are the same or different from each other, and each independently can be a single bond or a C6-C 18 arylene group.

[0116] According to another example, one or more L1 are the same or different from each other, and each independently can be a single bond or a group consisting of phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, triphenylene, fluorenylene and combinations thereof. The hydrogen of phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, triphenylene and fluorenylene can be selected from deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1~C 12 Alkyl, C6~C 10 The aryl group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 10 atomic nuclei and a heteroaryl group having 5 to 10 atomic nuclei.

[0117] In another example, L1 can be a single bond or a group selected from the following linking groups L1-1 to L1-3, but is not limited thereto.

[0118]

[0119] In the above-mentioned linking groups L1-1 to L1-3,

[0120] * refers to the part forming a bond with Chemical Formula 1,

[0121] d is an integer from 0 to 4,

[0122] Multiple R's are the same or different from each other.

[0123] R can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The group consisting of (aryl) (heteroaryl) amine groups and heteroaryl amine groups having 5 to 60 atomic nuclei, specifically, deuterium, halogen, cyano, nitro, amino, C1 to C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 A group composed of arylamine groups.

[0124] In the compound represented by the above chemical formula 1, Y1 is selected from the group consisting of O, S, C(R5)(R6) and N(R7), and Y2 is a single bond or selected from the group consisting of O, S, C(R8)(R9) and N(R 10 ). In this case, Y1 and Y2 are the same or different. Such a ring portion containing Y1 and Y2 is a dibenzo moiety. Depending on the difference between Y1 and Y2, the dibenzo moiety can be a monovalent dibenzofuranyl group, a monovalent dibenzothiophene group, a monovalent fluorenyl group, a monovalent carbazolyl group, a monovalent dibenzo-p-dioxin group (oxanhrene), a monovalent xanthene group (xanthene), a monovalent dihydroanthracenyl group, etc.

[0125] In addition, in the compound represented by the above Chemical Formula 1, a may be an integer from 0 to 7, specifically, an integer from 0 to 4.

[0126] When a is 0, it means that hydrogen is not replaced by a substituent R3. On the other hand, when a is an integer from 1 to 7, it means that hydrogen is replaced by a substituent R3. Multiple R3s may be the same or different.

[0127] The above R3, R5 to R 10The same or different groups may be independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with adjacent groups (for example: R3-R3, R5-R6, R8-R9) to form a condensed ring, specifically, independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 or condenses with adjacent groups (e.g., R3-R3, R5-R6, R8-R9) to form a condensed ring.

[0128] At this time, the above R3, R5 to R 10 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl) amino group and a heteroaryl amino group having 5 to 60 atomic nuclei, or the above-mentioned substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0129] According to one example, the above The moiety may be selected from the group consisting of the following moieties Mo3-1 to Mo3-17, but is not limited thereto.

[0130]

[0131]

[0132]

[0133] Among the above parts Mo3-1 to Mo3-17,

[0134] * refers to the part forming a bond with Chemical Formula 1,

[0135] Y1, a and R3 are each the same as defined in the above chemical formula 1,

[0136] CyA and CyB are the same or different from each other and are independently selected from C6 to C 30 A group consisting of a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 atomic nuclei,

[0137] a1 is an integer from 0 to 5,

[0138] a2 is an integer from 0 to 3,

[0139] e is an integer from 0 to 8,

[0140] e1 is an integer from 0 to 6,

[0141] e2 is an integer from 0 to 4,

[0142] R is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei,

[0143] The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB are each independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amino groups and heteroarylamino groups having 5 to 60 atomic nuclei. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0144] According to another example, the above The moiety may be selected from the group consisting of the following moieties Mo4-1 to Mo4-71, but is not limited thereto.

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] In the above parts Mo4-1 to Mo4-71,

[0152] * refers to the part forming a bond with Chemical Formula 1,

[0153] CyA and CyB are the same or different from each other and are independently selected from C6 to C 30 A group consisting of a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 atomic nuclei,

[0154] The condensed aromatic rings of CyA and CyB are independently selected from deuterium (D), halogen, cyano, C1-C 40 Alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0155] In addition, the hydrogen of the above-mentioned parts Mo4-1 to Mo4-71 can be selected from deuterium (D), halogen, cyano, C1-C 40 Alkyl, C1~C 40 Halogenated alkyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl groups (e.g., phenyl, biphenyl, etc.), heteroaryl groups with 5 to 60 atomic nuclei (e.g., carbazolyl, phenoxazine, dibenzo-p-dioxin, etc.), C1-C 40 Alkylsilyl (eg methylsilyl), C6~C 60 Aryl silyl (eg phenyl silyl, etc.) and C6~C 60The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0156] Depending on the above Y1, Y2, L1, R1 and R2, the compound represented by the above Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 4 to 37. However, the present invention is not limited thereto.

[0157] [Chemical Formula 4]

[0158]

[0159] [Chemical Formula 5]

[0160]

[0161] [Chemical Formula 6]

[0162]

[0163] [Chemical Formula 7]

[0164]

[0165] [Chemical Formula 8]

[0166]

[0167] [Chemical Formula 9]

[0168]

[0169] [Chemical Formula 10]

[0170]

[0171] [Chemical Formula 11]

[0172]

[0173] [Chemical Formula 12]

[0174]

[0175] [Chemical Formula 13]

[0176]

[0177] [Chemical Formula 14]

[0178]

[0179] [Chemical Formula 15]

[0180]

[0181] [Chemical Formula 16]

[0182]

[0183] [Chemical Formula 17]

[0184]

[0185] [Chemical Formula 18]

[0186]

[0187] [Chemical Formula 19]

[0188]

[0189] [Chemical Formula 20]

[0190]

[0191] [Chemical Formula 21]

[0192]

[0193] [Chemical Formula 22]

[0194]

[0195] [Chemical Formula 23]

[0196]

[0197] [Chemical Formula 24]

[0198]

[0199] [Chemical Formula 25]

[0200]

[0201] [Chemical Formula 26]

[0202]

[0203] [Chemical Formula 27]

[0204]

[0205] [Chemical Formula 28]

[0206]

[0207] [Chemical Formula 29]

[0208]

[0209] [Chemical formula 30]

[0210]

[0211] [Chemical Formula 31]

[0212]

[0213] [Chemical Formula 32]

[0214]

[0215] [Chemical Formula 33]

[0216]

[0217] [Chemical Formula 34]

[0218]

[0219] [Chemical Formula 35]

[0220]

[0221] [Chemical Formula 36]

[0222]

[0223] [Chemical Formula 37]

[0224]

[0225] In the above chemical formulas 4 to 37,

[0226] X1 to X3, Y1, Ar1, n, a, and R3 are each the same as those defined in the above Chemical Formula 1.

[0227] b1 and b2 are each an integer from 0 to 5,

[0228] a1 is an integer from 0 to 5,

[0229] a2 is an integer from 0 to 3,

[0230] e is an integer from 0 to 8,

[0231] e1 is an integer from 0 to 6,

[0232] e2 is an integer from 0 to 4,

[0233] X4 to X9 are the same or different from each other and are each independently N or C(R 17 ), but at least one of X4 to X9 is N,

[0234] CyA and CyB are the same or different from each other and are independently selected from C6 to C 30 A group consisting of a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 atomic nuclei,

[0235] R 11 to R 17 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring,

[0236] R is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei,

[0237] The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB and the R 13 to R 16 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the above-mentioned substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0238] The compound represented by Chemical Formula 1 of the present invention described above can be further embodied as the following compounds 1 to 142, but is not limited thereto.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] In the present invention, "alkyl" means a monovalent substituent derived from a linear 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, isopentyl, and hexyl.

[0247] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, and 2-butenyl, but are not limited thereto.

[0248] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0249] 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 groups include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantyl.

[0250] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with a heteroatom such as N, O, S, or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholinyl and piperazinyl.

[0251] In the present invention, "aryl" means 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, it also includes forms in which two or more rings are simply attached (pendant) or condensed. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, and anthracenyl.

[0252] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having an atomic number of 5 to 60. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, it may also include a form in which two or more rings are simply attached to each other (pendant) or condensed, and further include a form condensed with an aryl group. Examples of such heteroaryl groups include six-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-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, but are not limited thereto.

[0253] In the present invention, "alkoxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms and may have a linear, branched, or cyclic structure. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, and pentoxy.

[0254] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, where R is an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthyloxy, and diphenoxy.

[0255] In the present invention, "alkylsilyl" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only monoalkylsilyl groups but also dialkylsilyl groups and trialkylsilyl groups. Furthermore, "arylsilyl" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms, and includes not only monoarylsilyl groups but also polyarylsilyl groups such as diarylsilyl groups and triarylsilyl groups.

[0256] In the present invention, an "alkylboryl group" means a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and an "arylboryl group" means a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0257] In the present invention, "alkylphosphinyl" means a phosphinyl group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only monoalkylphosphinyl groups but also dialkylphosphinyl groups. In addition, in the present invention, "arylphosphinyl" means a phosphinyl group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, and includes not only monoarylphosphinyl groups but also diarylphosphinyl groups.

[0258] In the present invention, the "arylamine group" means an amine group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only a monoarylamine group but also a diarylamine group.

[0259] In the present invention, the "heteroarylamine group" means an amine group substituted with a heteroaryl group having 5 to 60 atomic nuclei, and includes not only a monoheteroarylamine group but also a diheteroarylamine group.

[0260] In the present invention, the (aryl)(heteroaryl)amino group means an amino group substituted with an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 5 to 60 atomic nuclei.

[0261] In the present invention, "condensed ring" means 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 atomic nuclei, a condensed heteroaromatic ring having 5 to 60 atomic nuclei, a C3-C 60 spiro ring or the combination thereof.

[0262] In the present invention, "nuclear number" means the number of ring atoms constituting a ring structure, and the nucleus may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine means 6, including the 5 C atoms and 1 N atoms constituting the pyridine ring.

[0263] <Organic Electroluminescent Element>

[0264] In another aspect, the present invention provides an organic electroluminescent device (hereinafter referred to as “organic EL device”) comprising the compound represented by the above Chemical Formula 1.

[0265] Specifically, if Figures 1 to 3 As shown, the organic electroluminescent element of the present invention includes an anode 100, a cathode 200, and one or more organic layers 300 interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes the compound represented by Chemical Formula 1. In this case, the above compounds can be used alone or in combination of two or more.

[0266] The one or more organic layers 300 may include one or more of a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport layer 340, and an electron injection layer 350, and may optionally further include an electron transport auxiliary layer 360. In this case, at least one organic layer 300 includes the compound represented by Chemical Formula 1. Specifically, the organic layer including the compound represented by Chemical Formula 1 may be the electron transport layer 340 or the electron transport auxiliary layer 360.

[0267] According to one example, the above-mentioned one or more organic 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 optionally, may further include an electron transport auxiliary layer. The above-mentioned electron transport layer includes the compound represented by the above-mentioned chemical formula 1. At this time, the compound represented by the above-mentioned chemical formula 1 is included in the organic electroluminescent element as an electron transport layer substance. In such an organic electroluminescent element, due to the compound of the above-mentioned chemical formula 1, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer, and quickly migrate from the electron transport layer to the light-emitting layer, so that the binding force between the holes and electrons in the light-emitting layer is strong. Therefore, the organic electroluminescent element of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above-mentioned chemical formula 1 has excellent thermal stability and electrochemical stability, thereby improving the performance of the organic electroluminescent element.

[0268] The compound of Chemical Formula 1 can be used alone or mixed with electron transport layer materials known in the art.

[0269] 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 generally known in the art. As non-limiting examples of usable electron transport materials, there are oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (for example: Alq3, tris (8-hydroxyquinoline) -aluminum (tris (8-quinolinolato) -aluminium)), gallium complexes (for example: Gaq'2OPiv, Gaq'2OAc, 2 (Gaq'2)), etc. They can be used alone or in combination of two or more.

[0270] In the present invention, when the compound of Chemical Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0271] According to another example, the above-mentioned one or more organic layers include 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 the compound represented by the above-mentioned chemical formula 1. At this time, the compound represented by the above-mentioned chemical formula 1 is included in the organic electroluminescent element as an electron transport auxiliary layer substance. The compound represented by the above-mentioned chemical formula 1 has a high triplet energy. Therefore, in the case of including the compound of the above-mentioned chemical formula 1 as an electron transport auxiliary layer substance, the efficiency of the organic electroluminescent element can be improved due to the triplet-triplet fusion (TTF) effect. In addition, the compound of the above-mentioned chemical formula 1 can prevent the 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 that contribute to light emission in the light-emitting layer increases, thereby improving the luminous efficiency of the element, and the durability and stability of the element are improved, thereby effectively increasing the life of the element.

[0272] The compound of Chemical Formula 1 can be used alone or mixed with electron transport auxiliary layer materials known in the art.

[0273] In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 includes electron transport substances generally known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc., but is not limited thereto.

[0274] The structure of the organic electroluminescent element of the present invention is not particularly limited. For example, an anode 100, one or more organic layers 300, and a cathode 200 may be sequentially stacked on a substrate (see FIG. Figures 1 to 3 Furthermore, although not shown in the figure, an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.

[0275] According to one example, Figure 1 As shown, the organic electroluminescent element 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 stacked on a substrate. Figure 2 As shown, an electron injection layer 350 may be provided between the electron transport layer 340 and the cathode 200. In addition, an electron transport auxiliary layer 360 (see Figure 3 ).

[0276] In the organic electroluminescent element of the present invention, at least one layer of the organic layer 300 [for example, the electron transport layer 340 or the electron transport auxiliary layer 360] contains the compound represented by the above chemical formula 1. In addition, the organic layer and the electrode can be formed and manufactured using materials and methods known in the art.

[0277] The organic layer may be formed by vacuum deposition or solution coating, such as spin coating, dip coating, doctor blade coating, inkjet printing, or thermal transfer, but is not limited thereto.

[0278] The substrate that can be used in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like.

[0279] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited to these.

[0280] In addition, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin or lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0281] The hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and common materials known in the art can be used.

[0282] Hereinafter, the present invention will be described in detail by way of examples, which are as follows. However, the following examples are merely illustrative of the present invention and the present invention is not limited thereto.

[0283] [Preparation Example 1]-Synthesis of Compound Sub-1

[0284]

[0285] 60.0 g (198.6 mmol) of 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine, 54.4 g (198.6 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 6.88 g (5.9 mmol) of Pd(PPh3)4, and 82.3 g (595.7 mmol) of K2CO3 were added to 600 ml of toluene, 150 ml of EtOH, and 150 ml of H2O and heated under reflux with stirring for 6 hours. After the reaction was terminated, the organic layer was extracted with dichloromethane and MgSO4 was added, and the water was removed and filtered. After filtration, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using acetone. The solid was filtered out and washed with acetone, and then dried in an oven to obtain 81.3 g of compound Sub-1 (yield 82.6%).

[0286] Mass: [(M+H) + ]:467

[0287] [Preparation Example 2]-Synthesis of Compound Sub-2

[0288]

[0289] 93.2 g of compound Sub-2 (yield 81.1%) was obtained by the same method as in Preparation Example 1, except that 70.0 g (231.7 mmol) of 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine, 63.5 g (231.7 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 8.0 g (6.9 mmol) of Pd(PPh3)4, 96.1 g (695.0 mmol) of K2CO3, 700 ml of toluene, 175 ml of EtOH, and 175 ml of H2O were used instead of the substances used in Preparation Example 1.

[0290] Mass: [(M+H) + ]:497

[0291] [Preparation Example 3]-Synthesis of Compound Sub-3

[0292]

[0293] 89.9 g of compound Sub-3 (yield 78.2%) was obtained using the same method as Preparation Example 1, except that 70.0 g (232.4 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine, 63.72 g (232.4 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 8.1 g (6.9 mmol) of Pd(PPh3)4, 96.4 g (697.3 mmol) of K2CO3, 700 ml of toluene, 175 ml of EtOH, and 175 ml of H2O were used instead of the substances used in Preparation Example 1.

[0294] Mass: [(M+H) + ]:496

[0295] [Preparation Example 4]-Synthesis of Compound Sub-4

[0296]

[0297] 98.3 g of compound Sub-4 (yield 85.4%) was obtained using the same method as in Preparation Example 1, except that 70.0 g (232.4 mmol) of 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine, 63.72 g (232.4 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 8.1 g (6.9 mmol) of Pd(PPh3)4, 96.4 g (697.3 mmol) of K2CO3, 700 ml of toluene, 175 ml of EtOH, and 175 ml of H2O were used instead of the substances used in Preparation Example 1.

[0298] Mass: [(M+H) + ]:496

[0299] [Preparation Example 5]-Synthesis of Compound Sub-5

[0300]

[0301] 80.7 g of compound Sub-5 (yield 70.2%) was obtained using the same method as Preparation Example 1, except that 70.0 g (231.7 mmol) of 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine, 63.5 g (231.7 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 8.0 g (6.9 mmol) of Pd(PPh3)4, 96.1 g (695.0 mmol) of K2CO3, 700 ml of toluene, 175 ml of EtOH, and 175 ml of H2O were used instead of the substances used in Preparation Example 1.

[0302] Mass: [(M+H) + ]:497

[0303] [Preparation Example 6]-Synthesis of Compound Sub-6

[0304]

[0305] 60.4 g of compound Sub-6 (yield 77.9%) was obtained by the same method as in Preparation Example 1, except that 50.0 g (142.4 mmol) of 4-chloro-6-(3-chlorophenyl)-2-(naphthalene-2-yl)pyrimidine, 39.0 g (142.4 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 4.9 g (4.3 mmol) of Pd(PPh3)4, 59.0 g (427.1 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 1.

[0306] Mass: [(M+H) + ]:546

[0307] [Preparation Example 7]-Synthesis of Compound Sub-7

[0308]

[0309] 50.0 g (142.4 mmol) of 4-chloro-6-(3-chlorophenyl)-2-(naphthalen-1-yl)pyrimidine, 39.0 g (142.4 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 4.9 g (4.3 mmol) of Pd(PPh3)4, 59.0 g (427.1 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 1. 52.1 g of compound Sub-7 (yield 67.2%) was obtained using the same method as Preparation Example 1.

[0310] Mass: [(M+H) + ]:546

[0311] [Preparation Example 8]-Synthesis of Compound Sub-8

[0312]

[0313] 40.0 g (106.0 mmol) of 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(3-chlorophenyl)pyrimidine, 29.0 g (106.0 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 3.7 g (3.2 mmol) of Pd(PPh3)4, 43.9 g (318.1 mmol) of K2CO3, 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O were used instead of the substances used in Preparation Example 1. 43.4 g of compound Sub-8 (yield 71.7%) was obtained using the same method as Preparation Example 1.

[0314] Mass: [(M+H) + ]:572

[0315] [Preparation Example 9]-Synthesis of Compound Sub-9

[0316]

[0317] 53.4 g of compound Sub-9 (yield 88.2%) was obtained by the same method as in Preparation Example 1, except that 40.0 g (106.0 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-(3-chlorophenyl)pyrimidine, 29.0 g (106.0 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 3.7 g (3.2 mmol) of Pd(PPh3)4, 43.9 g (318.1 mmol) of K2CO3, 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O were used instead of the substances used in Preparation Example 1.

[0318] Mass: [(M+H) + ]:572

[0319] [Preparation Example 10]

[0320] <Step 1> Synthesis of 2-chloro-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine

[0321]

[0322] 45.0 g (199.0 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 43.0 g (149.3 mmol) of (3-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid, 6.9 g (5.9 mmol) of Pd(PPh3)4, and 82.5 g (597.2 mmol) of K2CO3 were added to 600 ml of toluene, 150 ml of EtOH, and 150 ml of H2O, and heated under reflux with stirring for 6 hours. After the reaction was completed, the organic layer was extracted with dichloromethane, MgSO4 was added, the water was removed, and the mixture was filtered. After filtration, the solvent in the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered and washed with methanol, and then dried in an oven to obtain 33.8 g of 2-chloro-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 39.2%).

[0323] Mass: [(M+H) + ]:435

[0324] <Step 2> 2-(2-chloro-[1,1'-biphenyl]-4-yl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6- Synthesis of Phenyl-1,3,5-Triazine

[0325]

[0326] 33.8 (78.0 mmol) of 2-chloro-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 18.1 g (78.0 mmol) of (2-chloro-[1,1'-biphenyl]-4-yl)boronic acid, 2.7 g (2.3 mmol) of Pd(PPh3)4, 32.4 g (234.1 mmol) of K 2CO3, 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O were used instead of the substances used in Preparation Example 1. The same method as Preparation Example 1 was used to obtain 38.4 g of 2-(2-chloro-[1,1'-biphenyl]-4-yl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 83.9%).

[0327] Mass: [(M+H) + ]:587

[0328] <Step 3> Synthesis of Compound Core-1

[0329]

[0330] 38.4 g (65.5 mmol) of 2-(2-chloro-[1,1'-biphenyl]-4-yl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 21.6 g (85.1 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.4 g (1.9 mmol) of Pd(dppf)Cl2, 19.3 g (196.4 mmol) of KOAc, and 1.9 g (3.9 mmol) of Xphos were added to 400 ml of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was completed, the organic layer was extracted with dichloromethane, MgSO4 was added, the water was removed, and the mixture was filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and solidified using methanol. The solid was filtered, washed with methanol, and then dried in an oven to obtain 31.2 g of compound Core-1 (yield 70.4%).

[0331] Mass: [(M+H) + ]:678

[0332] [Preparation Example 11]

[0333] <Step 1> 2-chloro-4-(3-chlorophenyl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-1,3,5-triazine Synthesis

[0334]

[0335] 30.6 g of 2-chloro-4-(3-chlorophenyl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-1,3,5-triazine (yield 34.1%) was obtained by the same method as in step 1 of Preparation Example 10, except that 50.0 g (191.9 mmol) of 2,4-dichloro-6-(3-chlorophenyl)-1,3,5-triazine, 41.5 g (143.9 mmol) of (3-(dibenzo[b,d]furan-2-yl)phenyl)boric acid, 6.7 g (5.8 mmol) of Pd(PPh3)4, 79.6 g (575.8 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 10.

[0336] Mass: [(M+H) + ]:469

[0337] <Step 2>2-([1,1':2',1 ” -terphenyl]-4'-yl)-4-(3-chlorophenyl)-6-(3-(dibenzo[b,d]furo Synthesis of (pyran-2-yl)phenyl)-1,3,5-triazine

[0338]

[0339] 30.6g (65.4mmol) of 2-chloro-4-(3-chlorophenyl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-1,3,5-triazine, 17.9g (65.4mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 2.3g (1.9mmol) of Pd(PPh3)4, 27.1g (196.3mmol) of ) K2CO3, 400ml of toluene, 100ml of EtOH, and 100ml of H2O were used instead of the substances used in Preparation Example 1. Otherwise, 35.6g of 2-(2-chloro-[1,1'-biphenyl]-4-yl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 82.1%) was obtained using the same method as Preparation Example 1.

[0340] Mass: [(M+H) + ]:663

[0341] <Step 3> Synthesis of Compound Core-2

[0342]

[0343] 25.6 g of compound Core-2 (yield 63.2%) was obtained by the same method as in Step 3 of Preparation Example 10, except that 35.6 g (53.7 mmol) of 2-(2-chloro-[1,1'-biphenyl]-4-yl)-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 17.7 g (69.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.2 g (1.6 mmol) of Pd(dppf)Cl2, 15.8 g (161.2 mmol) of KOAc, 1.5 g (3.2 mmol) of Xphos, and 400 ml of 1,4-dioxane were used instead of the substances used in Preparation Example 10.

[0344] Mass: [(M+H) + ]:754

[0345] [Preparation Example 12]

[0346] <Step 1> 2-chloro-4-(3-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine synthesis

[0347]

[0348] 35.1 g of 2-chloro-4-(3-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 33.9%) was obtained by the same method as in step 1 of Preparation Example 10, except that 50.0 g (221.2 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 53.5 g (165.9 mmol) of (3-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)boric acid, 7.7 g (6.6 mmol) of Pd(PPh3)4, 91.7 g (663.5 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 10.

[0349] Mass: [(M+H) + ]:469

[0350] <Step 2>2-([1,1':2',1 ” -terphenyl]-4'-yl)-4-(3-chloro-5-(dibenzo[b,d]furan-2-yl) benzene Synthesis of 6-phenyl-1,3,5-triazine

[0351]

[0352] 35.1 g (74.9 mmol) of 2-chloro-4-(3-chloro-5-(dibenzo[b, d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 20.6 g (74.9 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 2.6 g (2.3 mmol) of Pd(PPh3)4, 31.1 g (224.9 mmol) of K2 CO3, 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O were used instead of the substances used in Preparation Example 1. The same method as Preparation Example 1 was used to obtain 38.9 g of 2-([1,1':2',1"-terphenyl]-4'-yl)-4-(3-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 78.4%).

[0353] Mass: [(M+H) + ]:663

[0354] <Step 3> Synthesis of Compound Core-3

[0355]

[0356] 29.3 g of compound Core-3 (yield 66.2%) was obtained by the same method as in Step 3 of Preparation Example 10, except that 38.9 g (58.8 mmol) of 2-([1,1':2',1"-terphenyl]-4'-yl)-4-(3-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 19.4 g (76.4 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.3 g (1.8 mmol) of Pd(dppf)Cl2, 17.3 g (176.4 mmol) of KOAc, 1.7 g (3.5 mmol) of Xphos, and 400 ml of 1,4-dioxane were used instead of the substances used in Preparation Example 10.

[0357] Mass: [(M+H) + ]:754

[0358] [Preparation Example 13]

[0359] <Step 1> 2-chloro-4-(2-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine synthesis

[0360]

[0361] 30.9 g of 2-chloro-4-(2-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 29.8%) was obtained by the same method as in step 1 of Preparation Example 10, except that 50.0 g (221.2 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 53.5 g (165.9 mmol) of (2-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)boric acid, 7.7 g (6.6 mmol) of Pd(PPh3)4, 91.7 g (663.5 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 10.

[0362] Mass: [(M+H) + ]:469

[0363] <Step 2>2-([1,1':2',1 ” -terphenyl]-4'-yl)-4-(2-chloro-5-(dibenzo[b,d]furan-2-yl) Synthesis of 6-phenyl-1,3,5-triazine

[0364]

[0365] 30.9 g (65.9 mmol) of 2-chloro-4-(2-chloro-5-(dibenzo[b, d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 20.6 g (65.9 mmol) of [1,1':2',1"-terphenyl]-4'-ylboronic acid, 2.3 g (2.0 mmol) of Pd(PPh3)4, 27.3 g (197.7 mmol) of K 2CO3, 300 ml of toluene, 75 ml of EtOH, and 75 ml of H2O were used instead of the substances used in Preparation Example 1. The same method as Preparation Example 1 was used to obtain 32.8 g of 2-([1,1':2',1"-terphenyl]-4'-yl)-4-(2-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine (yield 75.1%).

[0366] Mass: [(M+H) + ]:663

[0367] <Step 3> Synthesis of Compound Core-4

[0368]

[0369] 22.8 g of compound Core-4 (yield 61.1%) was obtained by the same method as in Step 3 of Preparation Example 10, except that 32.8 g (49.5 mmol) of 2-([1,1':2',1"-terphenyl]-4'-yl)-4-(2-chloro-5-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine, 16.3 g (64.4 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.1 g (1.5 mmol) of Pd(dppf)Cl2, 14.6 g (148.5 mmol) of KOAc, 1.4 g (3.0 mmol) of Xphos, and 300 ml of 1,4-dioxane were used instead of the substances used in Preparation Example 10.

[0370] Mass: [(M+H) + ]:754

[0371] [Preparation Example 14]

[0372] <Step 1> Synthesis of 4-chloro-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine

[0373]

[0374] 32.2 g of 4-chloro-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine (yield 33.5%) was obtained by the same method as in step 1 of Preparation Example 10, except that 50.0 g (221.2 mmol) of 4,6-dichloro-2-phenylpyrimidine, 48.0 g (166.6 mmol) of (3-(dibenzo[b,d]furan-2-yl)phenyl)boric acid, 7.7 g (6.7 mmol) of Pd(PPh3)4, 92.1 g (666.5 mmol) of K2CO3, 500 ml of toluene, 125 ml of EtOH, and 125 ml of H2O were used instead of the substances used in Preparation Example 1.

[0375] Mass: [(M+H) + ]:434

[0376] <Step 2> 4-(2-chloro-[1,1'-biphenyl]-4-yl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2- Synthesis of Phenylpyrimidine

[0377]

[0378] 32.2 g (74.4 mmol) of 4-chloro-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine, 17.3 g (74.4 mmol) of (2-chloro-[1,1'-biphenyl]-4-yl)boric acid, 2.6 g (2.2 mmol) of Pd(PPh3)4, 30.8 g (223.1 mmol) of K2CO3, 300 ml of toluene, 75 ml of EtOH, and 75 ml of H2O were used instead of the substances used in Preparation Example 1. 34.2 g of 4-(2-chloro-[1,1'-biphenyl]-4-yl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine was obtained using the same method as Preparation Example 1 (yield 78.7%).

[0379] Mass: [(M+H) + ]:586

[0380] <Step 3> Synthesis of Compound Core-5

[0381]

[0382] 28.1 g of compound Core-5 (yield 70.9%) was obtained by the same method as in Step 3 of Preparation Example 10, except that 34.2 g (58.5 mmol) of 4-(2-chloro-[1,1'-biphenyl]-4-yl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine, 19.3 g (76.1 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.3 g (1.8 mmol) of Pd(dppf)Cl2, 17.2 g (175.6 mmol) of KOAc, 1.7 g (3.5 mmol) of Xphos, and 300 ml of 1,4-dioxane were used instead of the substances used in Preparation Example 10.

[0383] Mass: [(M+H) + ]:677

[0384] [Synthesis Example 1] Synthesis of Compound 5

[0385]

[0386] 12.0 g (1 eq, 24.2 mmol) of compound Sub-1 from [Preparation Example 1], 8.1 g (1.05 eq, 25.4 mmol) of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.7 mmol) of Pd(OAc)2, 23.6 g (3.0 eq, 72.6 mmol) of Cs2CO3, and 0.7 g (0.06 eq, 1.5 mmol) of Xphos were added to 150 ml of toluene, 37.5 ml of EtOH, and 37.5 ml of H2O, and the mixture was heated under reflux and reacted for 4 hours. After the reaction was completed, the organic layer was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the mixture was subjected to column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 11.1 g of Compound 5 (yield 70.2%).

[0387] Mass: [(M+H) + ]:655

[0388] [Synthesis Example 2] Synthesis of Compound 11

[0389]

[0390] The same process as in [Synthesis Example 1] was carried out except that 13.0 g (1 eq, 26.2 mmol) of compound Sub-2 of [Preparation Example 2], 10.9 g (1.05 eq, 27.5 mmol) of 2-(9,9-dimethyl-5-phenyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 25.6 g (3.0 eq, 78.6 mmol) of Cs2CO3, 0.7 g (0.06 eq, 1.6 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1, thereby obtaining 15.9 g of compound 11 (yield 83.3%).

[0391] Mass: [(M+H) + ]:731

[0392] [Synthesis Example 3] Synthesis of Compound 18

[0393]

[0394] The same process as in [Synthesis Example 1] was carried out except that 17.0 g (1 eq, 34.3 mmol) of compound Sub-3 of [Preparation Example 3], 10.9 g (1.05 eq, 36.1 mmol) of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 1.0 mmol) of Pd(OAc)2, 33.6 g (3.0 eq, 103.0 mmol) of Cs2CO3, 1.0 g (0.06 eq, 2.1 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1, thereby obtaining 17.7 g of compound 18 (yield 78.9%).

[0395] Mass: [(M+H) + ]:654

[0396] [Synthesis Example 4] Synthesis of Compound 19

[0397]

[0398] 12.0 g (1 eq, 24.2 mmol) of compound Sub-3 of [Preparation Example 3], 9.2 g (1.05 eq, 25.5 mmol) of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluorene]-4'-yl)-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.7 mmol) of Pd(OAc)2, 23.7 g (3.0 eq, 72.7 mmol) of Cs2CO3, 0.7 g (0.06 eq, 1.4 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 13.9 g of compound 19 (yield 82.5%).

[0399] Mass: [(M+H) + ]:694

[0400] [Synthesis Example 5] Synthesis of Compound 29

[0401]

[0402] 14.0 g (1 eq, 28.3 mmol) of compound Sub-4 of [Preparation Example 4], 10.7 g (1.05 eq, 29.7 mmol) of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluorene]-4'-yl)-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 27.6 g (3.0 eq, 84.8 mmol) of Cs2CO3, 0.8 g (0.06 eq, 1.7 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 17.3 g of compound 29 (yield 88.3%).

[0403] Mass: [(M+H) + ]:694

[0404] [Synthesis Example 6] Synthesis of Compound 32

[0405]

[0406] 15.0 g (1 eq, 30.3 mmol) of compound Sub-4 of [Preparation Example 4], 11.8 g (1.05 eq, 31.8 mmol) of 2-(7,7-dimethyl-7H-benzo[c]fluoren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 29.6 g (3.0 eq, 90.9 mmol) of Cs2CO3, 0.9 g (0.06 eq, 1.8 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 16.6 g of compound 32 (yield 77.9%).

[0407] Mass: [(M+H) + ]:704

[0408] [Synthesis Example 7] Synthesis of Compound 33

[0409]

[0410] 10.0 g (1 eq, 20.2 mmol) of compound Sub-3 of [Preparation Example 3], 9.3 g (1.05 eq, 21.2 mmol) of 4,4,5,5-tetramethyl-2-(3-(spiro[cyclohexane-1,9'-fluorene]-4'-yl)phenyl)-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.6 mmol) of Pd(OAc)2, 19.7 g (3.0 eq, 72.7 mmol) of Cs2CO3, 0.6 g (0.06 eq, 1.2 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 11.1 g of compound 33 (yield 71.1%).

[0411] Mass: [(M+H) + ]:770

[0412] [Synthesis Example 8] Synthesis of Compound 51

[0413]

[0414] 15.0 g (1 eq, 30.2 mmol) of compound Sub-5 of [Preparation Example 5], 11.4 g (1.05 eq, 31.7 mmol) of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluorene]-2'-yl)-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 29.6 g (3.0 eq, 90.7 mmol) of Cs2CO3, 0.8 g (0.06 eq, 1.8 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out except that the above was carried out to obtain 14.6 g of compound 51 (yield 69.8%).

[0415] Mass: [(M+H) + ]:695

[0416] [Synthesis Example 9] Synthesis of Compound 67

[0417]

[0418] 13.0 g (1 eq, 23.8 mmol) of compound Sub-6 of [Preparation Example 6], 9.0 g (1.05 eq, 25.0 mmol) of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluorene]-4'-yl)-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.7 mmol) of Pd(OAc)2, 23.3 g (3.0 eq, 71.5 mmol) of Cs2CO3, 0.7 g (0.06 eq, 1.4 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 14.0 g of compound 67 (yield 79.3%).

[0419] Mass: [(M+H) + ]:744

[0420] [Synthesis Example 10] Synthesis of Compound 68

[0421]

[0422] The same process as in [Synthesis Example 1] was carried out except that 15.0 g (1 eq, 27.5 mmol) of compound Sub-6 of [Preparation Example 6], 9.2 g (1.05 eq, 28.9 mmol) of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 26.9 g (3.0 eq, 82.6 mmol) of Cs2CO3, 0.8 g (0.06 eq, 1.6 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1, thereby obtaining 14.5 g of compound 68 (yield 75.2%).

[0423] Mass: [(M+H) + ]:704

[0424] [Synthesis Example 11] Synthesis of Compound 70

[0425]

[0426] 15.0 g (1 eq, 27.5 mmol) of compound Sub-7 of [Preparation Example 7], 9.2 g (1.05 eq, 28.9 mmol) of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 26.9 g (3.0 eq, 82.6 mmol) of Cs2CO3, 0.8 g (0.06 eq, 1.6 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out except that the above was carried out to obtain 10.4 g of compound 70 (yield 53.9%).

[0427] Mass: [(M+H) + ]:704

[0428] [Synthesis Example 12] Synthesis of Compound 71

[0429]

[0430] 15.0 g (1 eq, 26.3 mmol) of compound Sub-8 of [Preparation Example 8], 9.9 g (1.05 eq, 27.6 mmol) of 4,4,5,5-tetramethyl-2-(spiro[cyclohexane-1,9'-fluorene]-4'-yl)-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 25.7 g (3.0 eq, 78.8 mmol) of Cs2CO3, 0.7 g (0.06 eq, 1.6 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 16.4 g of compound 71 (yield 81.2%).

[0431] Mass: [(M+H) + ]:770

[0432] [Synthesis Example 13] Synthesis of Compound 72

[0433]

[0434] 10.0 g (1 eq, 18.3 mmol) of compound Sub-6 of [Preparation Example 6], 5.7 g (1.05 eq, 19.3 mmol) of 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.5 mmol) of Pd(OAc)2, 17.9 g (3.0 eq, 55.0 mmol) of Cs2CO3, 0.5 g (0.06 eq, 1.1 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out, thereby obtaining 11.0 g of compound 72 (yield 88.9%).

[0435] Mass: [(M+H) + ]:678

[0436] [Synthesis Example 14] Synthesis of Compound 74

[0437]

[0438] 10.0 g (1 eq, 18.3 mmol) of compound Sub-6 of [Preparation Example 6], 6.2 g (1.05 eq, 19.3 mmol) of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.5 mmol) of Pd(OAc)2, 17.9 g (3.0 eq, 55.0 mmol) of Cs2CO3, 0.5 g (0.06 eq, 1.1 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out except that the above was carried out to obtain 8.5 g of compound 74 (yield 65.9%).

[0439] Mass: [(M+H) + ]:704

[0440] [Synthesis Example 15] Synthesis of Compound 76

[0441]

[0442] 14.0 g (1 eq, 24.5 mmol) of compound Sub-9 of [Preparation Example 9], 7.6 g (1.05 eq, 25.8 mmol) of 2-(dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.03 eq, 0.7 mmol) of Pd(OAc)2, 23.9 g (3.0 eq, 73.5 mmol) of Cs2CO3, 0.7 g (0.06 eq, 1.5 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 1. The same process as [Synthesis Example 1] was carried out except that the above was performed to obtain 14.9 g of compound 76 (yield 86.3%).

[0443] Mass: [(M+H) + ]:704

[0444] [Synthesis Example 16] Synthesis of Compound 97

[0445]

[0446] 15.0 g (1.0 eq, 22.1 mmol) of compound Core-1 from [Preparation Example 10], 5.9 g (1.0 eq, 22.1 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.8 g (0.7 mmol) of Pd(PPh3)4, and 9.2 g (66.4 mmol) of K2CO3 were added to 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O, stirred under reflux, and reacted for 4 hours. After the reaction was completed, the solid was cooled to room temperature, filtered, and washed with toluene and acetone. The solid was added to 1,2-dichlorobenzene, dissolved by boiling, filtered through silica, and washed with hot 1,2-dichlorobenzene to remove the catalyst and base. The filtrate was concentrated, recrystallized with 1,2-dichlorobenzene, and then filtered. Thereafter, recrystallization was repeated once, thereby obtaining 14.1 g of Compound 97 (yield 81.2%).

[0447] Mass: [(M+H) + ]:784

[0448] [Synthesis Example 17] Synthesis of Compound 99

[0449]

[0450] 15.0 g (1.0 eq, 19.9 mmol) of compound Core-2 of [Preparation Example 11], 5.9 g (1.0 eq, 19.9 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.7 g (0.6 mmol) of Pd(PPh3)4, 8.3 g (59.7 mmol) of K2CO3, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. Otherwise, the same process as [Synthesis Example 16] was carried out to obtain 13.3 g of compound 99 (yield 77.9%).

[0451] Mass: [(M+H) + ]:860

[0452] [Synthesis Example 18] Synthesis of Compound 102

[0453]

[0454] 15.0 g (1.0 eq, 19.9 mmol) of compound Core-3 of [Preparation Example 12], 5.9 g (1.0 eq, 19.9 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.7 g (0.6 mmol) of Pd(PPh3)4, 8.3 g (59.7 mmol) of K2CO3, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. Otherwise, the same process as [Synthesis Example 16] was carried out to obtain 15.3 g of compound 102 (yield 89.2%).

[0455] Mass: [(M+H) + ]:860

[0456] [Synthesis Example 19] Synthesis of Compound 103

[0457]

[0458] 15.0 g (1.0 eq, 19.9 mmol) of compound Core-4 of [Preparation Example 13], 5.9 g (1.0 eq, 19.9 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.7 g (0.6 mmol) of Pd(PPh3)4, 8.3 g (59.7 mmol) of K2CO3, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. Otherwise, the same process as [Synthesis Example 16] was carried out to obtain 11.9 g of compound 103 (yield 69.3%).

[0459] Mass: [(M+H) + ]:860

[0460] [Synthesis Example 20] Synthesis of Compound 105

[0461]

[0462] 15.0 g (1.0 eq, 22.2 mmol) of compound Core-5 of [Preparation Example 14], 5.9 g (1.0 eq, 22.2 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.8 g (0.7 mmol) of Pd(PPh3)4, 9.2 g (66.5 mmol) of K2CO3, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. Otherwise, the same process as [Synthesis Example 16] was carried out to obtain 15.2 g of compound 105 (yield 87.9%).

[0463] Mass: [(M+H) + ]:783

[0464] [Synthesis Example 21] Synthesis of Compound 109

[0465]

[0466] 7.0 g (1 eq, 14.1 mmol) of compound Sub-3 of [Preparation Example 3], 5.5 g (1.05 eq, 14.8 mmol) of 2-(3-(dibenzo[b,d]furan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.4 mmol) of Pd(OAc)2, 13.8 g (3.0 eq, 42.4 mmol) of Cs2CO3, 0.4 g (0.06 eq, 0.8 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. The same process as [Synthesis Example 1] was carried out except that the above was carried out to obtain 7.7 g of compound 109 (yield 77.9%).

[0467] Mass: [(M+H) + ]:704

[0468] [Synthesis Example 22] Synthesis of Compound 125

[0469]

[0470] 10.0 g (1 eq, 20.2 mmol) of compound Sub-5 of [Preparation Example 5], 6.8 g (1.05 eq, 21.2 mmol) of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.1 g (0.03 eq, 0.6 mmol) of Pd(OAc)2, 19.7 g (3.0 eq, 60.5 mmol) of Cs2CO3, 0.6 g (0.06 eq, 1.2 mmol) of Xphos, 200 ml of toluene, 50 ml of EtOH, and 50 ml of H2O were used instead of the substances used in Synthesis Example 16. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 9.9 g of compound 125 (yield 75.4%).

[0471] Mass: [(M+H) + ]:655

[0472] [Example 1] Preparation of blue organic electroluminescent element

[0473] Compound 1 was purified to high purity by sublimation according to a commonly known method, and then a blue organic electroluminescent device was prepared as follows.

[0474] First, we will A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water wash, 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, Hwashintech). Afterwards, the substrate was cleaned with UV light for 5 minutes and then transferred to a vacuum evaporator.

[0475] On the ITO transparent electrode prepared as above, HT-1+2% HAT-CN was used. / HT-1 / HT-2 / BH+2%BD / ET-2 / Compound 1:LiQ=1:1 / LiF / Al The organic electroluminescent device was fabricated by sequentially stacking the layers. The structures of the compounds HT-1, HAT-CN, HT-2, BH, BD, ET-2, and LiQ used in this process are shown below.

[0476]

[0477] [Examples 2 to 5] Preparation of blue organic electroluminescent elements

[0478] A blue organic electroluminescent device was produced in the same manner as in Example 1 except that the substances listed in Table 1 below were used instead of Compound 1 used as the electron transport layer substance in Example 1.

[0479] [Comparative Example 1] Preparation of a blue organic electroluminescent element

[0480] A blue organic electroluminescent device was produced in the same manner as in Example 1 except that Compound ET-1 was deposited to a thickness of 30 nm instead of Compound 1 used as the electron transport layer material in Example 1.

[0481] At this time, the structure of ET-1 used is as follows.

[0482]

[0483] [Evaluation Example 1]

[0484] The current density of 10 mA / cm was measured for each of the blue organic electroluminescent devices prepared in Examples 1 to 5 and Comparative Example 1. 2 The driving voltage, lifespan (T95), current efficiency and luminescence peak under the conditions are shown in Table 1 below.

[0485] [Table 1]

[0486]

[0487] As can be seen from Table 1 above, the blue organic electroluminescent elements of Examples 1 to 5 using the compounds of the present invention as electron transport layer materials show excellent performance in terms of driving voltage, luminescence peak and current efficiency compared with the blue organic electroluminescent element of Comparative Example 1 using the conventional ET-1 for the electron transport layer.

[0488] [Example 6] Production of blue organic electroluminescent element

[0489] Compound 1 was purified to high purity by sublimation according to a commonly known method, and then a blue organic electroluminescent device was prepared as follows.

[0490] First, we will A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water wash, 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, Hwashintech). Afterwards, the substrate was cleaned with UV light for 5 minutes and then transferred to a vacuum evaporator.

[0491] On the ITO transparent electrode prepared as above, HT-1+2% HAT-CN was used. / HT-1 / HT-2 / BH+2%BD / Compound 1 / ET-1:LiQ=1:1 / LiF / Al The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2, and LiQ used in this process are the same as those described in Example 1, and ET-1 is the same as that described in Comparative Example 1, so its description is omitted.

[0492] [Examples 7 to 22] Production of blue organic electroluminescent elements

[0493] A blue organic electroluminescent device was produced in the same manner as in Example 6 except that the substances listed in Table 2 below were used instead of Compound 1 used as the electron transport assisting layer substance in Example 6.

[0494] [Comparative Examples 2 to 5] Production of Blue Organic Electroluminescent Elements

[0495] by A blue organic electroluminescent device was produced in the same manner as in Example 6, except that compounds ET-2 to ET-5 were respectively deposited instead of Compound 1 used as the electron-transport assisting layer material in Example 6. The structures of ET-2, ET-3, ET-4, and ET-5 used in this case are as follows.

[0496]

[0497] [Evaluation Example 2]

[0498] The current density of the organic electroluminescent devices manufactured in Examples 6 to 22 and Comparative Example 2 was measured at 10 mA / cm 2 The driving voltage, luminescence wavelength, lifespan, current efficiency, and luminescence wavelength under the conditions are shown in Table 2 below.

[0499] [Table 2]

[0500]

[0501] As shown in Table 2, the blue organic electroluminescent elements of Examples 6 to 22 containing the compounds of the present invention as electron transport assisting layer materials exhibited superior performance in current efficiency and driving voltage compared to the organic electroluminescent elements of Comparative Examples 2 to 5.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, X1 to X3 are the same as or different from each other and are each independently N or C(R4), but at least two of X1 to X3 are N, R1 and R2 are the same or different and are independently selected from deuterium, halogen, cyano, nitro, amino, C3-C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 and a heteroaryl group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring, Ar1 is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, n is an integer from 0 to 5, L1 is a single bond or selected from C1 to C 60 Alkylene, C6~C 60 and heteroarylene groups having an atomic nucleus number of 5 to 60, Y1 is selected from the group consisting of O, S, C(R5)(R6) and N(R7), Y2 is a single bond or is selected from O, S, C(R8)(R9) and N(R 10 ), a is an integer from 0 to 7, R3 to R 10 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring, The cycloalkyl, heterocycloalkyl, aryl, heteroaryl and condensed ring of R1 and R2, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine and heteroarylamine of Ar1, the alkylene, arylene and heteroarylene of L1, and the R3 to R 10 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2 or 3: [Chemical Formula 2] [Chemical Formula 3] In the chemical formulas 2 and 3, X1 to X3, Ar1, n, L1, Y1, Y2, a and R3 are each the same as defined in claim 1, b1 and b2 are each an integer from 0 to 5, X4 to X9 are the same or different from each other and are each independently N or C(R 17 ), but at least one of X4 to X9 is N, R 11 to R 17 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring, The R 13 to R 17 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

3. The compound according to claim 1, The moiety is selected from the group consisting of the following moieties Mo1-1 to Mo1-21: In the parts Mo1-1 to Mo1-21, c1 and c2 are each 0 or 1, but 1≤c1+c2≤2, c3 and c4 are each an integer from 0 to 5, but 1≤c3+c4≤10, c5 is an integer from 0 to 11, c6 is an integer from 0 to 5, c7 is an integer from 0 to 4, c8 is an integer from 0 to 2, c9 is an integer from 0 to 9, c10 and c11 are each 0 or 1, One or more R are the same or different and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, Z1 is O or S, Z3 and Z4 are single bonds or O or S, but excluding the case where Z3 and Z4 are single bonds at the same time, Z5 and Z6 are single bonds or O or S, but excluding the case where Z5 and Z6 are single bonds at the same time, Z7 and Z8 are single bonds or O or S, but excluding the case where Z7 and Z8 are single bonds at the same time, Ring Cy1 and ring Cy2 are the same or different and are each independently C6 to C 30 A condensed aromatic ring or a condensed heteroaromatic ring having 5 to 30 atomic nuclei, X4 to X6 are the same or different from each other and are each independently N or C(R 17 ), but at least one of X4 to X6 is N, X7 to X9 are the same as or different from each other and are each independently N or C(R 17 ), but at least one of X7 to X9 is N, Z9 is O or S, R 13 to R 17 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring, The R 13 to R 17 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

4. The compound according to claim 1, wherein L1 is a single bond or is selected from the group consisting of the following linking groups L1-1 to L1-3: In the linking groups L1-1 to L1-3, d is an integer from 0 to 4, R is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The group consisting of (aryl)(heteroaryl)amine groups and heteroarylamine groups having 5 to 60 atomic nuclei.

5. The compound according to claim 1, The moiety is selected from the group consisting of the following moieties Mo3-1 to Mo3-17: In the parts Mo3-1 to Mo3-17, Y1, a and R3 are each the same as defined in claim 1, CyA and CyB are the same or different from each other and are independently selected from C6 to C 30 A group consisting of a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 atomic nuclei, a1 is an integer from 0 to 5, a2 is an integer from 0 to 3, e is an integer from 0 to 8, e1 is an integer from 0 to 6, e2 is an integer from 0 to 4, R is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB are independently selected from deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The present invention may be substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amine groups and heteroarylamine groups having 5 to 60 atomic nuclei. In this case, when there are multiple substituents, they may be the same as or different from each other.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 37: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [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] [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] In the chemical formulas 4 to 37, X1 to X3, Y1, Ar1, n, a, and R3 are each the same as defined in claim 1, b1 and b2 are each an integer from 0 to 5, a1 is an integer from 0 to 5, a2 is an integer from 0 to 3, e is an integer from 0 to 8, e1 is an integer from 0 to 6, e2 is an integer from 0 to 4, X4 to X9 are the same or different from each other and are each independently N or C(R 17 ), but at least one of X4 to X9 is N, CyA and CyB are the same or different from each other and are independently selected from C6 to C 30 A group consisting of a condensed aromatic ring and a condensed heteroaromatic ring having 5 to 30 atomic nuclei, R 11 to R 17 The same or different from each other, each independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl) (heteroaryl) amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or condensed with an adjacent group to form a condensed ring, R is selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 A group consisting of an (aryl)(heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, The condensed aromatic ring and condensed heteroaromatic ring of CyA and CyB and the R 13 to R 16 The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide, arylamine, (aryl)(heteroaryl)amine, heteroarylamine and condensed ring are each independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkylsilyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Arylamine, C6~C 60 The amino group may be substituted or unsubstituted with one or more substituents selected from the group consisting of an (aryl) (heteroaryl)amine group and a heteroarylamine group having 5 to 60 atomic nuclei, or the substituents are condensed with adjacent groups to form a condensed ring. In this case, when there are multiple substituents, they may be the same as or different from each other.

7. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is selected from the group consisting of the following compounds 1 to 142:

8. An organic electroluminescent element comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode. At least one of the one or more organic layers comprises the compound according to any one of claims 1 to 7. 9 . The organic electroluminescent device according to claim 8 , wherein the organic layer containing the compound is an electron transport layer or an electron transport auxiliary layer.

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