Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to a novel compound and an organic electroluminescent device using same and, more specifically, to an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, luminescence ability, and the like and an organic electroluminescent device having improved characteristics in terms of luminescence efficiency, driving voltage, lifespan, and the like by including the organic compound in one or more organic material layers.

Description

Organic compounds and organic electroluminescent devices using the same

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

[0002] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected into the organic layer at the anode, and electrons are injected into the organic layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified according to their function, such as luminescent materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0003] Luminescent materials can be categorized into blue, green, and red luminescent materials based on their luminescent color, as well as yellow and orange luminescent materials for better natural color reproduction. Furthermore, host / dopant systems can be used as luminescent materials to enhance color purity and luminescence efficiency through energy transfer.

[0004] Dopant materials can be divided into fluorescent dopants, which utilize organic materials, and phosphorescent dopants, which utilize metal complexes containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescent materials, and therefore, extensive research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

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

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

[0007] The present invention aims to provide a novel organic compound that has excellent electron transport ability, electrochemical stability, thermal stability, etc. and can be used as an organic layer material of an organic electroluminescent device, specifically, an electron transport layer material and an electron transport auxiliary layer material.

[0008] In addition, the present invention aims to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, excellent electrical stability, and improved lifespan, including the novel compound.

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

[0010]

[0011] (In the above chemical formula 1,

[0012] a is 0 or 1,

[0013] Q1 and Q2 are the same or different, and are independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkylphosphine oxide group and C6~C 60 Selected from the group consisting of arylphosphine oxide groups,

[0014] b is 0 or 1,

[0015] R1 is deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0016] n is an integer from 0 to 5,

[0017] L1 is C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms,

[0018] Ar1 to Ar4 are the same or different from each other, and each independently represents deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0019] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkylphosphine oxide group and arylphosphine oxide group of the above Q1 and Q2, the arylene group and heteroarylene group of the above L1, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group and arylamine group of the above R1, Ar1 to Ar4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0020] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the aforementioned chemical formula 1.

[0021] In one example, the organic layer containing the compound may be an electron transport layer or an electron transport auxiliary layer.

[0022] Since the compound of the present invention has excellent electron transport ability, electrochemical stability, thermal stability, etc., it can be used as an organic layer material of an organic electroluminescent device. In particular, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, it is possible to manufacture an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, and long lifespan characteristics compared to conventional materials, and further, a full-color display panel with improved performance and lifespan can also be manufactured.

[0023] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

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

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

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

[0027] <Explanation of symbols>

[0028] 100: anode, 200: cathode,

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

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

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

[0032] 360: Electron transport auxiliary layer

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

[0034] <New organic compounds>

[0035] The present invention provides a novel organic compound that can be used as a high-efficiency organic layer material, particularly an electron transport layer material or an electron transport auxiliary layer material, due to its excellent electron injection and transport ability, electrochemical stability, thermal stability, etc.

[0036] Specifically, the novel compound according to the present invention has a structure in which two benzene rings substituted with a triazine derivative are bonded directly or through a linker group (e.g., a phenylene group, a biphenylene group, etc.), and a specific substituent (Q1) such as a phenyl group is introduced at the ortho-position based on the triazine derivative to at least one benzene ring, and is represented by the chemical formula 1.

[0037] In the compound represented by the above chemical formula 1, the triazine derivative is an electron-withdrawing group (EWG) with high electron absorption, which can improve electron mobility and thus electron transport properties of the compound. In addition, the triazine derivative also has excellent electrochemical stability. Therefore, when the compound according to the present invention is applied as a material for an electron transport layer or an electron transport auxiliary layer of an organic electroluminescent device, electrons can be smoothly transferred from the cathode (or electron injection layer) to the light-emitting layer, and as a result, the driving voltage of the device can be lowered, and high efficiency and long life characteristics can be realized.

[0038] In addition, by introducing a specific substituent (Q) such as a phenyl group to the 2nd position of the benzene ring based on the triazine derivative, the dihedral angle between the triazine derivative and the specific substituent increases, and accordingly, the charge transport properties (particularly, electron transport properties) are enhanced, so that the compound of the present invention can be used as a low-voltage, high-efficiency electron transport layer material.

[0039] In addition, the compound of the present invention can significantly increase its molecular weight by introducing various substituents (e.g., alkyl group, aryl group, heteroaryl group, etc.) into a triazine derivative, thereby increasing its glass transition temperature and improving its thermal safety and electrochemical stability.

[0040] As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron transport ability, thermal stability, electrochemical stability, etc., and thus can be used as an organic layer material of an organic electroluminescent device, specifically, an emission layer material, an electron transport layer / injection layer material, an electron transport auxiliary layer material, and more specifically, an electron transport layer material, an electron transport auxiliary layer material. In addition, an organic electroluminescent device including the compound of the chemical formula 1 can have significantly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

[0041]

[0042] In the compound represented by chemical formula 1 according to the present invention, a is 0 or 1. Here, when a is 0, it means that hydrogen is non-substituted with substituent Q2, and when a is 1, it means that hydrogen is substituted with substituent Q2.

[0043] In the above chemical formula 1, Q1 and Q2 are the same or different from each other, and each independently represents C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkylphosphine oxide group and C6~C 60 Selected from the group consisting of arylphosphine oxide groups, specifically C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylphosphine oxide groups. For example, Q1 and Q2 are the same or different from each other, and each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, an anthracenyl group, an anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, It can be selected from the group consisting of a dimethylphosphine oxide group and a diphenylphosphine oxide group, which are each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 10 Aryl group of , heteroaryl group with 5 to 10 nuclear atoms, C1 to C 10 Alkylphosphine oxide group and C6~C 20 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0044] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkylphosphine oxide group and arylphosphine oxide group of the above Q1 and Q2 are each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted or unsubstituted with one or more substituents (R) selected from the group consisting of arylamine groups, and specifically, each is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different. According to an example, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkylphosphine oxide group and arylphosphine oxide group of Q1 and Q2 may be independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dimethylphosphine oxide group and diphenylphosphine oxide group.

[0045] In one example, Q1 and Q2 are the same as or different from each other, and can be independently selected from the group consisting of the following substituents S1-1 to S1-12, but are not limited thereto.

[0046]

[0047] In the above substituents S1-1 to S1-12,

[0048] * indicates the part that is combined with chemical formula 1.

[0049] c is an integer from 0 to 5, specifically 0 or 1,

[0050] d is an integer from 0 to 4, specifically 0 or 1,

[0051] e is an integer from 0 to 7, specifically 0 or 1,

[0052] f is an integer from 0 to 9, specifically 0 or 1,

[0053] g is an integer from 0 to 8, specifically 0 or 1,

[0054] Multiple R's are the same or different from each other,

[0055] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamine groups, specifically deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms,

[0056] Z1, Z3 and Z5 are the same or different and are each independently selected from the group consisting of O, S, C(R2)(R3), Si(R4)(R5) and P(=O)(R6),

[0057] Z2, Z4 and Z6 are the same or different and are each independently C or Si,

[0058] R2 to R6 are the same or different, and each independently represent deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, specifically C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group and C6~C 30 It may be selected from the group consisting of arylphosphine oxide groups.

[0059] For example, R2 to R6 are the same or different from each other, and each independently represent a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, anthracenyl group, anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, It can be selected from the group consisting of a carbazolyl group, a dimethylphosphine oxide group and a diphenylphosphine oxide group, each of which is independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 20 Aryl group, heteroaryl group with 5 to 20 nuclear atoms, C1 to C 12 Alkylphosphine oxide group, C6~C 20 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0060] The above substituents S1-9 to S1-12 can be embodied as the following substituents Sb1-1 to Sb1-16, but are not limited thereto.

[0061]

[0062] The above substituents S1-9 to S1-12 can be embodied as the following substituents Sb1-17 to Sb1-35, but are not limited thereto.

[0063]

[0064]

[0065] In the above substituents Sb1-17 to Sb1-35,

[0066] * indicates a part that is combined with chemical formula 1.

[0067] The above substituents Sb1-17 to Sb1-35 are each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 20 Aryl group, heteroaryl group with 5 to 20 nuclear atoms, C1 to C 12 Alkylphosphine oxide group, C6~C 20 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0068] In the above chemical formula 1, b is 0 or 1. Here, when b is 0, it means that hydrogen is non-substituted with the substituent R1, and when b is 1, it means that hydrogen is substituted with the substituent R1.

[0069] R1 is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically C1~C 20 Alkyl group of C6~C 30 Aryl group of, heteroaryl group of 5 to 30 nuclear atoms, C1~C 40 Alkylphosphine oxide group and C6~C 60 It can be selected from the group consisting of arylphosphine oxide groups.

[0070] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group and arylamine group of the above R1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 40 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0071] For example, R1 is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, an anthracenyl group, an anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, a carbazolyl group, a dimethylphosphine oxide group, and It can be selected from the group consisting of diphenylphosphine oxide groups, and these are each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 20 Aryl group, heteroaryl group with 5 to 20 nuclear atoms, C1 to C 12 Alkylphosphine oxide group and C6~C 20It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0072] Depending on the presence or absence of Q1 and R1 and the position of introduction, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 5. However, the present invention is not limited thereto.

[0073]

[0074]

[0075]

[0076]

[0077] In the above chemical formulas 2 to 5,

[0078] Q1, Q2, R1, n, L1 and Ar1 to Ar4 are each as defined in the chemical formula 1 above.

[0079] In addition, depending on the bonding positions of the moieties on both sides centered on linker L1, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 6 to 21. However, the present invention is not limited thereto.

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] In the above chemical formulas 5 to 21,

[0097] a, b, Q1, Q2, R1, n, L1 and Ar1 to Ar4 are each as defined in the chemical formula 1 above.

[0098] In the above chemical formula 1, n is an integer from 0 to 5, and specifically, may be an integer from 0 to 3.

[0099] Here, when n is 0, it means that L1 is a single bond (direct bond), and on the other hand, when n is an integer from 1 to 5, L1 is C6~C 60 Selected from the group consisting of arylene group and heteroarylene group having 5 to 60 nuclear atoms, specifically C6~C 30 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0100] At this time, the arylene group and heteroarylene group of the above L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0101] For example, L1 can be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a divalent naphthalene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent carbazole group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent fluorene group, and combinations thereof. Here, the phenylene group, biphenylene group, terphenylene group, divalent naphthalene group, divalent phenanthrene group, divalent triphenylene group, divalent carbazole group, divalent dibenzofuran group, divalent dibenzothiophene group, and divalent fluorene group are each represented by deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 20 Aryl group, heteroaryl group with 5 to 20 nuclear atoms, C1 to C 12 Alkylphosphine oxide group and C6~C 20 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0102] According to another example, the above The moiety may be a linker group represented by the following chemical formula L.

[0103] [Chemical formula L]

[0104]

[0105] In the above chemical formula L,

[0106] n is an integer from 0 to 4, specifically an integer from 0 to 3,

[0107] h is an integer from 0 to 4, specifically 0 or 1,

[0108] Multiple R's are the same or different from each other,

[0109] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30 may be selected from the group consisting of arylamine groups. In one embodiment, R may be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dimethylphosphine oxide group, and diphenylphosphine oxide group.

[0110] In the above chemical formula 1, Ar1 to Ar4 are the same or different from each other, and each independently represents deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, specifically C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0111] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group and arylamine group of the above Ar1 to Ar4 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 20 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0112] According to an example, Ar1 to Ar4 are the same or different from each other, and each independently represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, anthracenyl group, an anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenoxathienyl group, an indolizinyl group, an indolyl group, a purinyl group, a quinolyl group, a benzothiazole group, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, It can be selected from the group consisting of a carbazolyl group, a dimethylphosphine oxide group, and a diphenylphosphine oxide group.

[0113] According to another example, Ar1 to Ar4 may be the same or different from each other, and may each independently be a substituent selected from the group consisting of the following substituents S2-1 to S2-45, but are not limited thereto.

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] In the above substituents S2-1 to S2-45,

[0120] * indicates a part that is combined with chemical formula 1.

[0121] The above substituents S2-1 to S2-45 are each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 20 Aryl group, heteroaryl group with 5 to 20 nuclear atoms, C1 to C 12 Alkylphosphine oxide group and C1~C 20 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylphosphine oxide groups.

[0122] Depending on the presence or absence of the aforementioned Q2 and R1, their introduction positions, the type of L1, and the bonding positions between the linker group L1 and the moieties on both sides, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 22 to 57. However, the present invention is not limited thereto.

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] In the above chemical formulas 22 to 57,

[0160] Q1, Q2, R1, n, Ar1 to Ar4 are each as defined in the above chemical formula 1,

[0161] h is an integer from 0 to 4,

[0162] Multiple R's are the same or different from each other,

[0163] R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group of , heteroaryl group having 5 to 30 nuclear atoms, C1~C 40 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group and C6~C 30may be selected from the group consisting of arylamine groups. In one embodiment, R may be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dimethylphosphine oxide group, and diphenylphosphine oxide group.

[0164] Specifically, the compound represented by chemical formula 1 according to the present invention may be a compound represented by any one of the following chemical formulas 58 to 93. However, the present invention is not limited thereto.

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In the above chemical formulas 58 to 93,

[0202] Q1, Q2, R1, Ar1 to Ar4 are each as defined in the chemical formula 1 above.

[0203] The compound represented by chemical formula 1 according to the present invention described above can be further specified as compounds 001 to 392 below, but is not limited thereto.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] In the present invention, the "number of nuclear atoms" means the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, P, and Se. For example, the number of nuclear atoms of pyridine means 6, including 5 C and 1 N constituting the pyridine ring.

[0240] In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0241] In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0242] In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0243] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0244] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons in the ring, is substituted with a heteroatom such as N, O, S, P or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0245] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0246] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, P, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, quinazolinyl group, phenanthrolinyl group, phenanthridyl group, dibenzofuran group, and dibenzothiophene group; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0247] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0248] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0249] In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl. In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0250] In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboron group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0251] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups. In addition, "arylphosphinyl group" in the present invention means a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl groups.

[0252] In the present invention, "alkylphosphine oxide group" means a phosphine oxide group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphine oxide groups. In addition, "arylphosphine oxide group" in the present invention means a phosphine oxide group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphine oxide groups.

[0253] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamine.

[0254] In the present invention, “heteroarylamine” means an amine substituted with a heteroaryl having 5 to 60 nuclear atoms, and includes not only mono- but also di-heteroarylamine.

[0255] In the present invention, (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 nuclear atoms. Here, the number of nuclear atoms means the number of atoms forming a ring, i.e., the number of ring atoms.

[0256] In the present invention, the "condensed ring" is a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclear atoms, a condensed heteroaromatic ring having 5 to 60 nuclear atoms, C3~C 60 It means a spyro ring or a combination thereof. Here, the nuclear atomic number means the number of atoms forming the ring, i.e. the number of ring atoms.

[0257]

[0258] Organic electroluminescent devices

[0259] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0260] Specifically, the organic electroluminescent device according to the present invention includes an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, as illustrated in FIGS. 1 to 3, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

[0261] The organic layer (300) of one or more layers above may include at least one 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 optionally may additionally include at least one of an electron transport auxiliary layer (360) and a hole transport auxiliary layer (not shown). At this time, at least one organic layer (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be an electron transport layer (340) or an electron transport auxiliary layer (360).

[0262] According to an example, the organic layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include at least one of an electron transport auxiliary layer and a hole transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound of the above chemical formula 1, and can also move quickly from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0263] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0264] In the present invention, the electron transport layer material that can be mixed with the compound of the above chemical formula 1 may be an electron transport material or n-type dopant commonly known in the art. Non-limiting examples of the electron transport material that can be used in the present invention include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, and aluminum complexes (e.g., Alq). 3,tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more. Examples of n-type dopants usable in the present invention may be metals (e.g., alkali metals or alkaline earth metals) or complexes of the above metals, and specifically, may be LiQ (Lithium Quinolate), etc.

[0265] In the present invention, when the compound of the above chemical formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately controlled within a range known in the art.

[0266] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. In this case, the compound represented by the chemical formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. The compound represented by the chemical formula 1 has a high triplet energy. Therefore, when the compound of the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer increases, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

[0267] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer auxiliary layer material known in the art.

[0268] In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and heterocyclic derivatives containing nitrogen, but is not limited thereto.

[0269] The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 to 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0270] According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer (350) may be positioned between the electron transport layer (340) and the cathode (200). In addition, an electron transport auxiliary layer (360) may be positioned between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0271] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the electron transport layer (340)] includes a compound represented by the chemical formula 1.

[0272] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0273] The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0274] Examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0275] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0276] In addition, the hole injection layer, hole transport layer, light emitting layer, electron injection layer, and hole transport auxiliary layer are not particularly limited, and conventional materials known in the art can be used.

[0277]

[0278] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0279] [Preparation Example 1] Synthesis of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (B01)

[0280]

[0281] 2-(4-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After completion of the reaction, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (19.7 g, 38.6 mmol, yield 81%).

[0282] Mass: [(M+H) + ] :512

[0283]

[0284] [Preparation Example 2] Synthesis of 2-(2-(naphthalen-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (B02)

[0285]

[0286] 2-(5-chloro-2-(naphthalen-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 42.6 mmol), bis(pinacolato)diboron (14.0 g, 55.3 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.6 mmol), and KOAc (8.4 g, 85.1 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-(2-(naphthalen-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (17.9 g, 31.9 mmol, yield 75%).

[0287] Mass: [(M+H) + ] :562

[0288]

[0289] [Preparation Example 3] Synthesis of 2,4-diphenyl-6-(2-(pyridin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (B03)

[0290]

[0291] 2-(5-chloro-2-(pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 47.5 mmol), bis(pinacolato)diboron (15.7 g, 61.8 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.0 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After completion of the reaction, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2,4-diphenyl-6-(2-(pyridin-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (17.5 g, 34.2 mmol, yield 72%).

[0292] Mass: [(M+H) + ] :513

[0293]

[0294] [Preparation Example 4] Synthesis of 2-(2-(dibenzo[b,d]furan-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (B04)

[0295]

[0296] 2-(5-chloro-2-(dibenzo[b,d]furan-4-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 39.2 mmol), bis(pinacolato)diboron (12.9 g, 51.0 mmol), Pd(dppf)Cl2 (0.9 g, 1.2 mmol), X-Phos (1.1 g, 2.4 mmol), KOAc (7.7 g, 78.4 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-(2-(dibenzo[b,d]furan-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (18.4 g, 30.6 mmol, yield 78%).

[0297] Mass: [(M+H) + ] :603

[0298]

[0299] [Preparation Example 5] Synthesis of 2-(2-(dibenzo[b,d]thiophen-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (B05)

[0300]

[0301] 2-(5-chloro-2-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 38.0 mmol), bis(pinacolato)diboron (12.6 g, 49.4 mmol), Pd(dppf)Cl2 (0.8 g, 1.1 mmol), X-Phos (1.1 g, 2.3 mmol), KOAc (7.5 g, 76.0 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-(2-(dibenzo[b,d]thiophen-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (17.4 g, 28.1 mmol, yield 74%).

[0302] Mass: [(M+H) + ] :619

[0303]

[0304] [Preparation Example 6] Synthesis of 2'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (B06)

[0305]

[0306] 3'-(4-(4-chloro-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (20.0 g, 38.4 mmol), bis(pinacolato)diboron (12.7 g, 49.9 mmol), Pd(dppf)Cl2 (0.8 g, 1.2 mmol), X-Phos (1.1 g, 2.3 mmol), KOAc (7.5 g, 76.8 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the product was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (17.4 g, 28.4 mmol, yield 74%).

[0307] Mass: [(M+H) + ] :614

[0308]

[0309] [Preparation Example 7] Synthesis of 3'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (B07)

[0310]

[0311] 3'-(4-(4-chloro-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (20.0 g, 38.4 mmol), bis(pinacolato)diboron (12.7 g, 49.9 mmol), Pd(dppf)Cl2 (0.8 g, 1.2 mmol), X-Phos (1.1 g, 2.3 mmol), KOAc (7.5 g, 76.8 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 3'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (17.6 g, 28.8 mmol, yield 75%).

[0312] Mass: [(M+H) + ] :614

[0313]

[0314] [Preparation Example 8] Synthesis of 4'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (B08)

[0315]

[0316] 4'-(4-(4-chloro-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (20.0 g, 38.4 mmol), bis(pinacolato)diboron (12.7 g, 49.9 mmol), Pd(dppf)Cl2 (0.8 g, 1.2 mmol), X-Phos (1.1 g, 2.3 mmol), KOAc (7.5 g, 76.8 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the product was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 4'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (18.1 g, 29.6 mmol, yield 77%).

[0317] Mass: [(M+H) + ] :614

[0318]

[0319] [Preparation Example 9] Synthesis of 3-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (B09)

[0320]

[0321] 3-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (20.0 g, 36.0 mmol), bis(pinacolato)diboron (11.9 g, 46.8 mmol), Pd(dppf)Cl2 (0.8 g, 1.1 mmol), X-Phos (1.0 g, 2.2 mmol), KOAc (7.1 g, 71.9 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 3-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (17.5 g, 27.0 mmol, yield 75%).

[0322] Mass: [(M+H) + ] :649

[0323]

[0324] [Preparation Example 10] Synthesis of 2-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (B10)

[0325]

[0326] 2-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (20.0 g, 36.0 mmol), bis(pinacolato)diboron (11.9 g, 46.8 mmol), Pd(dppf)Cl2 (0.8 g, 1.1 mmol), X-Phos (1.0 g, 2.2 mmol), KOAc (7.1 g, 71.9 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-methylbenzo[b]phosphindole 5-oxide (17.7 g, 27.3 mmol, yield 76%).

[0327] Mass: [(M+H) + ] :649

[0328]

[0329] [Preparation Example 11] Synthesis of (2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide (B11)

[0330]

[0331] (4'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide (20.0 g, 40.3 mmol), bis(pinacolato)diboron (13.3 g, 52.4 mmol), Pd(dppf)Cl2 (0.9 g, 1.2 mmol), X-Phos (1.2 g, 2.4 mmol), KOAc (7.9 g, 80.7 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain (2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide (17.8 g, 30.2 mmol, yield 75%).

[0332] Mass: [(M+H) + ] :588

[0333]

[0334] [Preparation Example 12] Synthesis of (4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-yl)dimethylphosphine oxide (B12)

[0335]

[0336] (4-(4-chloro-2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)dimethylphosphine oxide (20.0 g, 36.6 mmol), bis(pinacolato)diboron (12.1 g, 47.6 mmol), Pd(dppf)Cl2 (0.8 g, 1.1 mmol), X-Phos (1.0 g, 2.2 mmol), KOAc (7.2 g, 73.3 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain (4-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-yl)dimethylphosphine oxide (17.3 g, 27.1 mmol, yield 74%).

[0337] Mass: [(M+H) + ] :639

[0338]

[0339] [Preparation Example 13] Synthesis of 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (B13)

[0340]

[0341] 2-(5-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 47.6 mmol), bis(pinacolato)diboron (15.7 g, 61.9 mmol), Pd(dppf)Cl2 (1.0 g, 1.4 mmol), X-Phos (1.4 g, 2.9 mmol), and KOAc (9.3 g, 95.3 mmol) were added to 200 ml of 1,4-Dioxane and heated and stirred under reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2,4-diphenyl-6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazine (17.8 g, 34.8 mmol, yield 73%).

[0342] Mass: [(M+H) + ] :512

[0343]

[0344] [Preparation Example 14] Synthesis of 2-(2-(naphthalen-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (B14)

[0345]

[0346] 2-(4-chloro-2-(naphthalen-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (20.0 g, 42.6 mmol), bis(pinacolato)diboron (14.0 g, 55.3 mmol), Pd(dppf)Cl2 (0.9 g, 1.3 mmol), X-Phos (1.2 g, 2.6 mmol), and KOAc (8.4 g, 85.1 mmol) were added to 200 ml of 1,4-Dioxane and stirred under heating and reflux for 6 hours. After the reaction was completed, the mixture was filtered, concentrated to remove the solvent, and purified by column chromatography to obtain 2-(2-(naphthalen-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (17.4 g, 31.1 mmol, yield 73%).

[0347] Mass: [(M+H) + ] :562

[0348]

[0349] [Synthetic Example 1] Synthesis of 6,6'-([1,1':4',1''-terphenyl]-2',3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 002)

[0350]

[0351] Compound B01 (15.0 g, 29.3 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-([1,1':4',1''-terphenyl]-2',3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (14.6 g, 21.1 mmol, yield 72%).

[0352] Mass: [(M+H) + ] :694

[0353]

[0354] [Synthesis Example 2] Synthesis of 6,6'-([1,1':4',1''-terphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 006)

[0355]

[0356] Compound B01 (15.0 g, 29.3 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-([1,1':4',1''-terphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.2 g, 22.0 mmol, yield 75%).

[0357] Mass: [(M+H) + ] :694

[0358]

[0359] [Synthesis Example 3] Synthesis of 6,6'-([1,1':4',1''-terphenyl]-2',4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 010)

[0360]

[0361] Compound B01 (15.0 g, 29.3 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-([1,1':4',1''-terphenyl]-2',4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (14.6 g, 21.1 mmol, yield 72%).

[0362] Mass: [(M+H) + ] :694

[0363]

[0364] [Synthesis Example 4] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-3-yl)-6-phenyl-1,3,5-triazine (Compound 014)

[0365]

[0366] Compound B01 (15.0 g, 29.3 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dried with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-3-yl)-6-phenyl-1,3,5-triazine (18.0 g, 23.5 mmol, yield 80%).

[0367] Mass: [(M+H) + ] :770

[0368]

[0369] [Synthesis Example 5] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 018)

[0370]

[0371] Compound B01 (15.0 g, 29.3 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (13.6 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazine (17.6 g, 22.9 mmol, yield 78%).

[0372] Mass: [(M+H) + ] :770

[0373]

[0374] [Synthesis Example 6] Synthesis of 2-([1,1'-biphenyl]-4-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazine (Compound 019)

[0375]

[0376] Compound B13 (15.0 g, 29.3 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (13.6 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 13 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-([1,1'-biphenyl]-4-yl)-4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazine (17.4 g, 22.6 mmol, yield 77%).

[0377] Mass: [(M+H) + ] :770

[0378]

[0379] [Synthesis Example 7] Synthesis of 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-3-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (Compound 026)

[0380]

[0381] Compound B01 (15.0 g, 29.3 mmol), 2-(3-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (12.9 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-3-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.6 g, 22.3 mmol, yield 76%).

[0382] Mass: [(M+H) + ] :744

[0383]

[0384] [Synthesis Example 8] Synthesis of 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (Compound 030)

[0385]

[0386] Compound B01 (15.0 g, 29.3 mmol), 2-(2-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (12.9 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.8 g, 22.6 mmol, yield 77%).

[0387] Mass: [(M+H) + ] :744

[0388]

[0389] [Synthesis Example 9] Synthesis of 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (Compound 031)

[0390]

[0391] Compound B13 (15.0 g, 29.3 mmol), 2-(2-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (12.9 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 13 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.3 g, 22.0 mmol, yield 75%).

[0392] Mass: [(M+H) + ] :744

[0393]

[0394] [Synthesis Example 10] Synthesis of 2',3''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-1,1':4',1'':4'',1'''-quaterphenyl (Compound 038)

[0395]

[0396] Compound B01 (15.0 g, 29.3 mmol), 2-(4-bromo-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (13.6 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2',3''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-1,1':4',1'':4'',1'''-quaterphenyl (18.0 g, 23.5 mmol, yield 80%).

[0397] Mass: [(M+H) + ] :770

[0398]

[0399] [Synthesis Example 11] Synthesis of 6,6'-([1,1':3',1'':3'',1'''-quaterphenyl]-2',4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 043)

[0400]

[0401] Compound B13 (15.0 g, 29.3 mmol), 2-(2-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (13.6 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 13 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-([1,1':3',1'':3'',1'''-quaterphenyl]-2',4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (17.1 g, 22.3 mmol, yield 76%).

[0402] Mass: [(M+H) + ] :770

[0403]

[0404] [Synthesis Example 12] Synthesis of 6,6'-([1,1':4',1'':4'',1''':4''',1''''-quinquephenyl]-2',3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 050)

[0405]

[0406] Compound B01 (15.0 g, 29.3 mmol), 2-(4-bromo-[1,1':4',1''-terphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (15.9 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-([1,1':4',1'':4'',1''':4''',1''''-quinquephenyl]-2',3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (20.3 g, 24.1 mmol, yield 82%).

[0407] Mass: [(M+H) + ] :846

[0408]

[0409] [Synthetic Example 13] Synthesis of 6,6'-(4-(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 062)

[0410]

[0411] Compound B02 (15.0 g, 26.7 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.4 g, 26.7 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.1 mmol) synthesized in Preparation Example 2 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.3 g, 20.6 mmol, yield 77%).

[0412] Mass: [(M+H) + ] :744

[0413]

[0414] [Synthesis Example 14] Synthesis of 6,6'-(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 066)

[0415]

[0416] Compound B02 (15.0 g, 26.7 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.4 g, 26.7 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.1 mmol) synthesized in Preparation Example 2 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.5 g, 20.8 mmol, yield 78%).

[0417] Mass: [(M+H) + ] :744

[0418]

[0419] [Synthetic Example 15] Synthesis of 6,6'-(3'-(naphthalen-2-yl)-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 067)

[0420]

[0421] Compound B14 (15.0 g, 26.7 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.4 g, 26.7 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.1 mmol) synthesized in Preparation Example 14 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(3'-(naphthalen-2-yl)-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.3 g, 20.6 mmol, yield 77%).

[0422] Mass: [(M+H) + ] :744

[0423]

[0424] [Synthetic Example 16] Synthesis of 6,6'-(4-(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 074)

[0425]

[0426] Compound B02 (15.0 g, 26.7 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.4 g, 26.7 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.1 mmol) synthesized in Preparation Example 2 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (17.9 g, 21.9 mmol, yield 82%).

[0427] Mass: [(M+H) + ] :820

[0428]

[0429] [Synthetic Example 17] Synthesis of 6,6'-(4,4'-di(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 086)

[0430]

[0431] Compound B02 (15.0 g, 26.7 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (13.7 g, 26.7 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (11.1 g, 80.1 mmol) synthesized in Preparation Example 2 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4,4'-di(naphthalen-2-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (18.8 g, 21.6 mmol, yield 81%).

[0432] Mass: [(M+H) + ] :870

[0433]

[0434] [Synthetic Example 18] Synthesis of 6,6'-(4-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 098)

[0435]

[0436] Compound B03 (15.0 g, 29.3 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.8 mmol) synthesized in Preparation Example 3 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (16.5 g, 29.3 mmol, yield 81%).

[0437] Mass: [(M+H) + ] :695

[0438]

[0439] [Synthetic Example 19] Synthesis of 6,6'-(4'-(pyridin-3-yl)-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 102)

[0440]

[0441] Compound B03 (15.0 g, 29.3 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.8 mmol) synthesized in Preparation Example 3 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4'-(pyridin-3-yl)-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (16.0 g, 23.1 mmol, yield 79%).

[0442] Mass: [(M+H) + ] :695

[0443]

[0444] [Synthesis Example 20] Synthesis of 6,6'-(4-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 110)

[0445]

[0446] Compound B03 (15.0 g, 29.3 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.1 g, 87.8 mmol) synthesized in Preparation Example 3 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (16.5 g, 29.3 mmol, yield 81%).

[0447] Mass: [(M+H) + ] : 695

[0448]

[0449] [Synthetic Example 21] Synthesis of 6,6'-(4-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 122)

[0450]

[0451] Compound B04 (15.0 g, 24.9 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8.9 g, 24.9 mmol), Pd(PPh3)4 (0.9 g, 0.7 mmol), and K2CO3 (10.3 g, 74.8 mmol) synthesized in Preparation Example 4 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.8 g, 20.2 mmol, yield 81%).

[0452] Mass: [(M+H) + ] : 784

[0453]

[0454] [Synthetic Example 22] Synthesis of 6,6'-(4-(dibenzo[b,d]furan-4-yl)-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 134)

[0455]

[0456] Compound B04 (15.0 g, 24.9 mmol), 2-(5-bromo-2-(pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (11.6 g, 24.9 mmol), Pd(PPh3)4 (0.9 g, 0.7 mmol), and K2CO3 (10.3 g, 74.8 mmol) synthesized in Preparation Example 4 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 6,6'-(4-(dibenzo[b,d]furan-4-yl)-4'-(pyridin-3-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (15.8 g, 20.2 mmol, yield 81%).

[0457] Mass: [(M+H) + ] : 784

[0458]

[0459] [Synthesis Example 23] Synthesis of 6,6'-(4-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (Compound 158)

[0460]

[0461] Compound B05 (15.0 g, 30.6 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10.9 g, 30.6 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (12.7 g, 91.7 mmol) synthesized in Preparation Example 5 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2 6,6'-(4-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (19.8 g, 24.8 mmol, yield 81%).

[0462] Mass: [(M+H) + ] : 800

[0463]

[0464] [Synthesis Example 24] Synthesis of 2'-(4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 258)

[0465]

[0466] Compound B01 (15.0 g, 29.3 mmol), 2'-(4-(2-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (14.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 1 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2'-(4-(3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (18.6 g, 23.5 mmol, yield 80%).

[0467] Mass: [(M+H) + ] : 795

[0468]

[0469] [Synthetic Example 25] Synthesis of (4'-(4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)formonitrile (Compound 279)

[0470]

[0471] Compound B13 (15.0 g, 29.3 mmol), 4'-(4-(2-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (14.4 g, 29.3 mmol), Pd(PPh3)4 (1.0 g, 0.9 mmol), and K2CO3 (12.2 g, 88.0 mmol) synthesized in Preparation Example 13 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain (4'-(4-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)formonitrile (18.2 g, 22.9 mmol, yield 78%).

[0472] Mass: [(M+H) + ] : 795

[0473]

[0474] [Synthesis Example 26] Synthesis of 2'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 345)

[0475]

[0476] Compound B06 (15.0 g, 24.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.5 g, 24.5 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.2 g, 73.5 mmol) synthesized in Preparation Example 6 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.6 g, 19.6 mmol, yield 80%).

[0477] Mass: [(M+H) + ] : 795

[0478]

[0479] [Synthetic Example 27] Synthesis of 3'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 346)

[0480]

[0481] Compound B07 (15.0 g, 24.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.5 g, 24.5 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.2 g, 73.5 mmol) synthesized in Preparation Example 7 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 3'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.4 g, 19.3 mmol, yield 79%).

[0482] Mass: [(M+H) + ] : 795

[0483]

[0484] [Synthetic Example 28] Synthesis of 4'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (Compound 347)

[0485]

[0486] Compound B08 (15.0 g, 24.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.5 g, 24.5 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (10.2 g, 73.5 mmol) synthesized in Preparation Example 8 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-(3''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-2'-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (15.4 g, 19.3 mmol, yield 79%).

[0487] Mass: [(M+H) + ] : 795

[0488]

[0489] [Synthetic Example 29] Synthesis of 3-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-5-methylbenzo[b]phosphindole 5-oxide (Compound 361)

[0490]

[0491] Compound B09 (15.0 g, 23.2 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.0 g, 23.2 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (9.6 g, 69.5 mmol) synthesized in Preparation Example 9 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 3-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-5-methylbenzo[b]phosphindole 5-oxide (15.4 g, 18.5 mmol, yield 80%).

[0492] Mass: [(M+H) + ] : 830

[0493]

[0494] [Synthesis Example 30] Synthesis of 2-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-5-methylbenzo[b]phosphindole 5-oxide (Compound 362)

[0495]

[0496] Compound B10 (15.0 g, 23.2 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.0 g, 23.2 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (9.6 g, 69.5 mmol) synthesized in Preparation Example 9 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 2-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-5-methylbenzo[b]phosphindole 5-oxide (15.0 g, 18.1 mmol, yield 78%).

[0497] Mass: [(M+H) + ] : 830

[0498]

[0499] [Synthesis Example 31] Synthesis of (2',3''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-yl)dimethylphosphine oxide (Compound 379)

[0500]

[0501] Compound B11 (15.0 g, 25.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.9 g, 25.5 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (10.6 g, 76.7 mmol) synthesized in Preparation Example 11 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain (2',3''-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':4',1''-terphenyl]-4-yl)dimethylphosphine oxide (15.5 g, 20.2 mmol, yield 79%).

[0502] Mass: [(M+H) + ] : 770

[0503]

[0504] [Synthesis Example 32] Synthesis of (4-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)dimethylphosphine oxide (Compound 380)

[0505]

[0506] Compound B12 (15.0 g, 23.5 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.1 g, 23.5 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (9.8 g, 70.6 mmol) synthesized in Preparation Example 12 were added to 150 ml of toluene, 22.5 ml of ethanol, and 22.5 ml of water, and heated and stirred under reflux for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain (4-(3,3'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-yl)dimethylphosphine oxide (15.6 g, 19.1 mmol, yield 81%).

[0507] Mass: [(M+H) + ] : 820

[0508]

[0509] [Example 1] - Fabrication of a blue organic electroluminescent device

[0510] Compound 002 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

[0511] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV light and transferred to a vacuum deposition machine.

[0512] On the ITO transparent electrode prepared as above, compounds A and B were co-deposited at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and then compound A was deposited on the hole injection layer to form a hole transport layer having a thickness of 1400 Å. Subsequently, compound C was deposited at a thickness of 50 Å on the hole transport layer to form a hole transport auxiliary layer, and compounds D and E were co-deposited at a weight ratio of 98:2 to form a light-emitting layer having a thickness of 200 Å. Subsequently, compound F was deposited on the light-emitting layer to form an electron transport auxiliary layer having a thickness of 50 Å, and then compound 002 and compound H were co-deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. Afterwards, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and Al was deposited on the electron injection layer to form a cathode with a thickness of 1000 Å, thereby manufacturing an organic light-emitting device. The structures of compounds A to F and H used here are as follows, respectively.

[0513]

[0514]

[0515]

[0516] [Examples 2 to 32] - Fabrication of blue organic electroluminescent devices

[0517] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds described in Table 1 below was used instead of Compound 002, which was used as an electron transport layer material in Example 1.

[0518]

[0519] [Comparative Examples 1 to 5] - Fabrication of a blue organic electroluminescent device

[0520] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that compounds H to L were used instead of compound 002, which was used as an electron transport layer material in Example 1. At this time, the structures of compounds H to L are as follows, respectively.

[0521]

[0522]

[0523] [Evaluation Example 1]

[0524] For the blue organic electroluminescent devices manufactured in Examples 1 to 32 and Comparative Examples 1 to 5, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0525] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 0023.74548.6 Example 2 Compound 0063.84538.3 Example 3 Compound 0103.84538.4 Example 4 Compound 0143.84548.4 Example 5 Compound 0183.74539.1 Example 6 Compound 0193.64538.9 Example 7 Compound 0263.64529.2 Example 8 Compound 0303.54538.8 Example 9 Compound 0313.64528.7 Example 10 Compound 0383.74519.2 Example 11 Compound 0433.84539.0 Example 12 Compound 0503.74548.9 Example 13 Compound 0623.84539.0 Example 14 Compound 0663.64529.1 Example 15 Compound 0673.54538.7 Example 16 Compound 0743.74558.3 ​​Example 17 Compound 0863.74548.4 Example 18 Compound 0983.74548.4 Example 19 Compound 1023.64539.0 Example 20 Compound 1103.64529.1 Example 21 Compound 1223.74538.5 Example 22 Compound 1343.74538.4 Example 23 Compound 1583.74548.4 Example 24 Compound 2583.54538.8 Example 25 Compound 2793.64528.9 Example 26 Compound 3453.64548.4 Example 27 Compound 3463.74538.4 Example 28 Compound 3473.84558.5 Example 29 Compound 3613.84558.3 ​​Example 30 Compound 3623.74548.3 Example 31 Compound 3793.74568.4 Example 32 Compound 3803.84558.4 Comparative Example Compound 1 H4.2 4567.1 Comparative Example 2 Compound I4.3 4557.0 Comparative Example 3 Compound J4.2 4557.2 Comparative Example 4 Compound K3.9 4567.9 Comparative Example 5 Compound L4.0 4557.8

[0526] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 32 using the compound of Chemical Formula 1 according to the present invention in the electron transport layer exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 5 using compounds H to K in the electron transport layer.

[0527] In addition, the compound of formula 1 according to the present invention is a compound in which two moieties are bonded directly or through a linker: a benzene ring; a triazine derivative bonded to the 1st carbon position of the benzene ring; and a phenyl group bonded (introduced) to the 2nd carbon position of the benzene ring, which is an ortho-position based on the triazine derivative, and the triazine derivative has excellent electron transport ability and electrochemical stability, and the electron density and flow of the compound can be improved by introducing the phenyl group into the triazine derivative at a specific position. The blue organic electroluminescent device of Examples 1 to 22 using the compound of the present invention in the electron transport layer is a blue organic electroluminescent device of Comparative Example 1 using a compound (e.g., Compound H) in the electron transport layer in which two benzene rings substituted only with triazine groups are bonded through a dibenzofuran group, which is a linker group; It was found that the blue organic electroluminescent device of Comparative Example 2, which used a compound in which two triazine groups were bonded via a spirobifluorene group (e.g., Compound I) in the electron transport layer; Comparative Example 3, which used a compound in which two benzene rings substituted only with triazine groups were bonded via an o-terphenyl group (e.g., Compound J) in the electron transport layer; Comparative Example 4, which used a compound in which a first benzene ring substituted with a triazine group and a second benzene ring substituted with a pyrimidine group and a phenyl group at the ortho-position were directly bonded (e.g., Compound K) in the electron hydrogen layer; and Comparative Example 5, which used a compound in which a first benzene ring substituted with a triazine group and a phenyl group at the meta-position and a second benzene ring substituted with a triazine group at the meta-position were directly bonded (e.g., Compound L) in the electron transport layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency.

[0528]

[0529] [Example 33] Fabrication of a blue organic electroluminescent device

[0530] Compound 002 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured as follows.

[0531] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV light and transferred to a vacuum deposition machine.

[0532] On the ITO transparent electrode prepared as above, compounds A and B were co-deposited at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and then compound A was deposited on the hole injection layer to form a hole transport layer having a thickness of 1400 Å. Subsequently, compound C was deposited at a thickness of 50 Å on the hole transport layer to form a hole transport auxiliary layer, and compounds D and E were co-deposited at a weight ratio of 98:2 to form a light-emitting layer having a thickness of 200 Å. Subsequently, compound 002 was deposited on the light-emitting layer to form an electron transport auxiliary layer having a thickness of 50 Å, and then compounds G and compound H were co-deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. Afterwards, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and Al was deposited on the electron injection layer to form a cathode with a thickness of 1000 Å, thereby manufacturing an organic light-emitting device. The structures of compounds A to E, G, and H used here are respectively as follows.

[0533]

[0534]

[0535]

[0536] [Examples 34 to 35] Fabrication of blue organic electroluminescent devices

[0537] A blue organic electroluminescent device was manufactured in the same manner as in Example 33, except that each of the compounds described in Table 2 below was used instead of Compound 002, which was used as an electron transport auxiliary layer material in Example 16.

[0538]

[0539] [Comparative Example 6] Fabrication of a Blue Organic Electroluminescent Device

[0540] A blue organic electroluminescent device was manufactured in the same manner as in Example 33, except that Compound F was used instead of Compound 002 as the electron transport auxiliary layer material. The structure of Compound F used here is as follows.

[0541]

[0542]

[0543] [Evaluation Example 2]

[0544] For the blue organic electroluminescent devices manufactured in Examples 33 to 35 and Comparative Example 6, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0545] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 33 Compound 0023.84557.7 Example 34 Compound 0063.94567.8 Example 35 Compound 0073.84547.7 Comparative Example 6 Compound F4.64566.9

[0546] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 33 to 35 using the compound of the present invention in the electron transport layer exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 6 using compound F in the electron transport auxiliary layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, a is 0 or 1, b is 0 or 1, Q1 and Q2 are identical or different, and are independently selected from C1 to C. 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkylphosphine oxide group and C6~C 60 is selected from the group consisting of arylphosphine oxide groups, R1 is deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, n is an integer from 0 to 5, L1 is C6~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, Ar1 to Ar4 are the same or different from each other, and each independently represents deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkylphosphine oxide group, arylphosphine oxide group of the above Q1 and Q2, the arylene group and heteroarylene group of the above L1, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, alkylphosphine oxide group, arylphosphine oxide group and arylamine group of the above R1, Ar1 to Ar4 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

2. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 5: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] (In the above chemical formulas 2 to 5, Q1, Q2, R1, n, L1, Ar1 to Ar4 are each as defined in Article 1).

3. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 6 to 21: [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] (In the above chemical formulas 5 to 21, a, b, Q1, Q2, R1, n, L1, Ar1 to Ar4 are each as defined in Article 1).

4. In paragraph 1, A compound wherein the above Q1 and Q2 are the same or different and are each independently selected from the group consisting of the following substituents S1-1 to S1-12: (In the above substituents S1-1 to S1-12, c is an integer from 0 to 5, d is an integer from 0 to 4, e is an integer from 0 to 7, f is an integer from 0 to 9, g is an integer from 0 to 8, Multiple R's are identical or different from each other, R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, Z1, Z3 and Z5 are the same or different from each other and are each independently selected from the group consisting of O, S, C(R2)(R3), Si(R4)(R5) and P(=O)(R6), Z2, Z4 and Z6 are the same or different from each other and are each independently C or Si, R2 to R6 are the same or different and each independently represents deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

5. In paragraph 1, Above The moiety is a compound which is a linker group represented by the following chemical formula L: [chemical formula L] (In the above chemical formula L, n is an integer from 0 to 4, h is an integer from 0 to 4, Multiple R's are identical or different from each other, R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

6. In paragraph 1, The compound wherein Ar1 to Ar4 are the same or different from each other and are each independently a substituent selected from the group consisting of the following substituents S2-1 to S2-28: .

7. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 22 to 57: [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] [Chemical formula 38] [Chemical Formula 39] [Chemical formula 40] [Chemical Formula 41] [Chemical formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical formula 46] [Chemical formula 47] [Chemical formula 48] [Chemical Formula 49] [Chemical formula 50] [Chemical Formula 51] [Chemical formula 52] [Chemical formula 53] [Chemical Formula 54] [Chemical formula 55] [Chemical formula 56] [Chemical formula 57] (In the above chemical formulas 22 to 57, Q1, Q2, R1, n, and Ar1 to Ar4 are each as defined in Article 1, h is an integer from 0 to 4, Multiple R's are identical or different from each other, R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C1~C 40 Alkylphosphine oxide group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

8. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 58 to 93: [Chemical formula 58] [Chemical formula 59] [Chemical formula 60] [Chemical formula 61] [Chemical formula 62] [Chemical formula 63] [Chemical formula 64] [Chemical formula 65] [Chemical formula 66] [Chemical formula 67] [Chemical formula 68] [Chemical formula 69] [Chemical formula 70] [Chemical formula 71] [Chemical formula 72] [Chemical formula 73] [Chemical formula 74] [Chemical formula 75] [Chemical formula 76] [Chemical formula 77] [Chemical formula 78] [Chemical formula 79] [Chemical formula 80] [Chemical formula 81] [Chemical formula 82] [Chemical formula 83] [Chemical formula 84] [Chemical formula 85] [Chemical formula 86] [Chemical formula 87] [Chemical formula 88] [Chemical formula 89] [Chemical formula 90] [Chemical formula 91] [Chemical formula 92] [Chemical formula 93] In the above chemical formulas 58 to 93, Q1, Q2, R1, Ar1 to Ar4 are each as defined in the chemical formula 1 above.

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of the following compounds: .

10. Anode; cathode; comprising at least one organic layer interposed between the anode and the cathode, An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises a compound according to any one of claims 1 to 9.

11. In paragraph 10, An organic electroluminescent device, wherein the organic layer containing the above compound is an electron transport layer or an electron transport auxiliary layer.

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