Organic compound and organic electroluminescent device comprising same

Abstract

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

Description

Organic compounds and organic electroluminescent devices containing the same

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

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

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

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

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

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

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

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

[0009]

[0010] (In the above chemical formula 1,

[0011] One of X1 and X2 is N, and the other is C(Ar3),

[0012] Ar1 and Ar2 are the same or different, and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0013] Ar3 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0014] n is an integer from 0 to 3.

[0015] L1 is a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0016] A is a substituent represented by the following chemical formula A1 or A2,

[0017] [Chemical Formula A1]

[0018]

[0019] [Chemical Formula A2]

[0020]

[0021] In the above chemical formulas A1 and A2,

[0022] * is a portion that is combined with the above chemical formula 1,

[0023] a, b1 and d are integers from 0 to 4, respectively,

[0024] b and d1 are integers from 0 to 3, respectively.

[0025] c and e are integers from 0 to 5, respectively.

[0026] R1 to R5 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, nitro, amino, hydroxy, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups to form a condensed ring,

[0027] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 to Ar3, 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, arylphosphine oxide group, arylamine group and condensed ring of the above R1 to R5 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, Amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0028] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0029] For example, the organic layer including the organic compound may be an electron transport layer and / or an electron transport auxiliary layer.

[0030] The compound of the present invention can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport and injection capabilities, heat resistance, electrochemical stability, etc. In particular, when the compound of the present invention is used as at least one of an electron transport layer material and an electron transport auxiliary layer material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be manufactured, and further, a full-color display panel with improved performance and lifespan can also be manufactured.

[0031] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0032] Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0033] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0034] <Explanation of symbols>

[0035] 100: positive, 200: negative,

[0036] 300: Organic layer, 310: Hole injection layer,

[0037] 320: hole transport layer, 330: light emitting layer,

[0038] 340: electron transport layer, 350: electron injection layer,

[0039] 360: Electron transport auxiliary layer

[0040] Hereinafter, the present invention will be described.

[0041] <New organic compounds>

[0042] The compound according to the present invention has a structure in which a moiety of a W structure in which ortho-phenylene groups are repeatedly bonded and a pyrimidine moiety are bonded directly or through a linker group (e.g., a phenylene group, a naphthalene group), and is represented by the above chemical formula 1. The compound according to the present invention provides a novel compound that can realize the characteristics of an organic electroluminescent device, such as high efficiency, long life, and low driving voltage characteristics of the device, by having excellent electron injection and transport ability, electrochemical stability, thermal stability, etc.

[0043] Specifically, in the compound represented by Chemical Formula 1 according to the present invention, the moiety having a W structure is a substituent having a W shape by repeatedly bonding five ortho-phenylene groups, and may be represented by Chemical Formula A1 or A2. Such a moiety having a W structure has a bulky structure compared to a substituent having a linear structure by repeatedly bonding meta-phenylene groups or para-phenylene groups. Therefore, the compound of the present invention containing a moiety having a W structure has a higher triplet energy (T1) compared to a compound containing a moiety in which meta-phenylene groups or para-phenylene groups are repeatedly bonded. For this reason, the compound of the present invention can block extra exciton coming from the light-emitting layer, and therefore, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, the efficiency of an organic electroluminescent device can be improved.

[0044] In addition, as described above, the moiety of the W structure is composed of a series of phenyl groups, and thus can further improve the thermal stability of the compound compared to moieties containing an aryl group such as fluorene or a cycloaryl group. Therefore, the compound of the present invention can improve the heat resistance of an organic electroluminescent device, thereby extending the life of the device.

[0045] In addition, in the compound represented by Chemical Formula 1 according to the present invention, the pyrimidine moiety is directly bonded to the moiety of the W structure, or bonded via a linker group such as a phenylene group. Since this pyrimidine moiety is an electron withdrawing group (EWG) with strong electron absorption, the compound of the present invention has a shallow LUMO energy level. Therefore, since the compound of the present invention has excellent electron transport and injection properties, it can be applied as an organic layer material of an organic electroluminescent device, particularly, a material of an electron transport layer or an electron transport auxiliary layer. In this case, 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.

[0046] As described above, the compound represented by the chemical formula 1 according to the present invention has excellent electron injection and transport capabilities, thermal stability, electrochemical stability, etc. Therefore, the compound of the present invention can be used as an organic layer of an organic electroluminescent device, preferably as an electron transport layer / injection layer material, an electron transport auxiliary layer material, and more preferably as an electron transport layer material, an electron transport auxiliary layer material. An organic electroluminescent device including the compound of the present invention 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.

[0047] In the chemical formula 1 according to the present invention, one of X1 and X2 is N, and the other is C(Ar3). Such X1 and X2-containing ring moiety ( The moiety) is a pyrimidine group and may be the following moiety Mo1-1 or Mo1-2.

[0048]

[0049] In the above moieties Mo1-1 and Mo1-2,

[0050] * indicates a site that is combined with the above chemical formula 1,

[0051] Ar1 to Ar3 are each as defined in the above chemical formula 1.

[0052] According to the above-mentioned X1 and X2, 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.

[0053]

[0054]

[0055]

[0056]

[0057] In the above chemical formulas 2 to 5,

[0058] n, L1, Ar1 to Ar3, a, b, b1, c, d, d1, e and R1 to R5 are each as defined in the above chemical formula 1.

[0059] In the chemical formula 1 according to the present invention, Ar1 and Ar2 are the same or different from each other, and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60is selected from the group consisting of arylamine groups, and specifically, each independently C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 may be selected from the group consisting of arylamine groups, and more specifically, each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, a fluorenyl group, anthracenyl group, anthryl group, a pyrenyl group, a pyridyl group, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a triazinyl, a phenoxathienyl, an indolizinyl, an indolyl, a purinyl, a quinolyl, a benzothiazole, a dibenzofuran group, a dibenzothiophene group, a phenanthrolinyl group, It can be selected from the group consisting of carbazolyl groups.

[0060] Ar3 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups, and more specifically, hydrogen, deuterium (D), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, dibenzofuran group, dibenzothiophene group, It can be selected from the group consisting of a phenanthrolinyl group and a carbazolyl group.

[0061] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 to Ar3 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~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, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0062] According to an example, Ar1 and Ar2 may be the same as or different from each other, and may be independently selected from the group consisting of the following substituents S1-1 to S1-18, but are not limited thereto.

[0063]

[0064]

[0065] In the above substituents S1-1 to S1-18,

[0066] f is an integer from 0 to 5, specifically an integer from 0 to 2,

[0067] g is an integer from 0 to 4, specifically an integer from 0 to 2,

[0068] h is an integer from 0 to 7, specifically an integer from 0 to 3,

[0069] i is an integer from 0 to 6, specifically an integer from 0 to 3,

[0070] j is an integer from 0 to 9, specifically an integer from 0 to 3,

[0071] k is an integer from 0 to 8, specifically an integer from 0 to 3,

[0072] l is an integer from 0 to 3, specifically an integer from 0 to 3,

[0073] Ar4 and Ar5 are the same or different, and are each independently C1~C 12 Alkyl group and C6~C 18 is selected from the group consisting of aryl groups, and specifically may be selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenylenyl group, a phenanthryl group, and a fluorenyl group,

[0074] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 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~C60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups, and more specifically, it can be selected from the group consisting of hydrogen, 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, and fluorene group.

[0075] According to another example, Ar1 and Ar2 may be the same as or different from each other, and may be independently selected from the group consisting of the following substituents S2-1 to S2-29, but are not limited thereto.

[0076]

[0077]

[0078]

[0079]

[0080] In the above substituents S2-1 to S2-29,

[0081] * is a site that is bonded to the X1, X2-ring moiety of the above chemical formula 1,

[0082] f1 is an integer from 1 to 5, specifically an integer from 1 to 2,

[0083] f2 is an integer from 0 to 5, specifically an integer from 1 to 2,

[0084] g1 is an integer from 0 to 4, specifically an integer from 1 to 2,

[0085] However, f2+g1≠0.

[0086] In the chemical formula 1 according to the present invention, n is an integer from 0 to 3. 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 3, L1 is a divalent linker group, C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. Specifically, L1 is a single bond, or C6~C 18 It may be an arylene group. Here, multiple L1s may be the same or different from each other.

[0087] 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), 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~C40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0088] In one embodiment, the L1 may be a single bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a fluorene group, and a combination thereof. Here, the hydrogen of the phenylene group, the biphenylene group, the terphenylene group, the naphthalene group, the phenanthrene group, the triphenylene group, and the fluorene group may be deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 10 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0089] According to another example, the L1 may be a single bond or may be, but is not limited to, the linker group L1-1 or L1-2.

[0090]

[0091] In the above linker groups L1-1 and L1-2,

[0092] o is an integer from 0 to 4, specifically an integer from 0 to 2,

[0093] p is an integer from 0 to 6, specifically an integer from 0 to 3,

[0094] Multiple R's are the same or different from each other,

[0095] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylamine groups, and more specifically, it can be selected from the group consisting of hydrogen, 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, and fluorene group.

[0096] According to another example, the L1 may be a single bond or may be selected from the group consisting of linker groups L2-1 to L2-8, but is not limited thereto.

[0097]

[0098] In the above linker groups L2-1 to L2-9,

[0099] * means a part that is combined with the above chemical formula 1,

[0100] o, p and R are as defined in the linker groups L1-1 and L1-2, respectively.

[0101] In the chemical formula 1 according to the present invention, A is a substituent having a bulky structure through repeated bonding of ortho-phenylene groups, and is a substituent represented by the chemical formula A1 or A2. The compound of the present invention containing such a substituent has a higher triplet energy (T1) than a compound having a linear structure through repeated bonding of meta-phenylene groups or para-phenylene groups. Therefore, since the electron transport layer or electron transport auxiliary layer of the compound of the present invention can block extra excitons coming from the light-emitting layer, the efficiency of the organic electroluminescent device can be improved.

[0102] In the above chemical formulas A1 and A2, a, b1 and d are each integers from 0 to 4, b and d1 are each integers from 0 to 3, and c and e are each integers from 0 to 5.

[0103] Here, when a, b, b1, c, d, d1, and e are each 0, it means that hydrogen is not substituted with each substituent (e.g., R1, R2, R3, R4, R5). On the other hand, when a, b1, and d are each integers of 1 to 4, b and d1 are each integers of 1 to 3, and c and e are each integers of 1 to 5, it means that hydrogen is substituted with each substituent (e.g., R1, R2, R3, R4, R5). At this time, a plurality of R1s are the same or different from each other, a plurality of R2s are the same or different from each other, a plurality of R3s are the same or different from each other, a plurality of R4s are the same or different from each other, and a plurality of R5s are the same or different from each other.

[0104] The above R1 to R5 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60Selected from the group consisting of arylamine groups, or condensed with adjacent groups to form a condensed ring, and specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 or may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, or may be condensed with adjacent groups (e.g., R1-R1, R1-R2, R1-R3, R1-R1, R2-R2, R2-R4, R2-R5, R3-R3, R3-R4, R4-R4, R4-R5, R5-R5) to form a condensed ring. Here, the condensed ring is C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 fused aromatic ring), fused heteroaromatic ring having 5 to 60 members (specifically, fused heteroaromatic ring having 5 to 30 members), C3 to C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0105] More specifically, the above R1 to R5 are the same or different from each other, and each independently represents deuterium (D), a cyano group, and C6~C 30 or may be selected from the group consisting of aryl groups, or may be condensed with adjacent groups (e.g., R1-R1, R1-R2, R1-R3, R1-R1, R2-R2, R2-R4, R2-R5, R3-R3, R3-R4, R4-R4, R4-R5, R5-R5) to form a condensed ring.

[0106] More specifically, R1 to R5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), a cyano group (-CN), a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group, or may be condensed with adjacent groups (e.g., R1-R1, R1-R2, R1-R3, R1-R1, R2-R2, R2-R4, R2-R5, R3-R3, R3-R4, R4-R4, R4-R5, R5-R5) to form a condensed ring.

[0107] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above R1 to R5 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 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 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, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0108] For example, the above A may be selected from the group consisting of the following substituents A3-1 to A3-10, but is not limited thereto.

[0109]

[0110]

[0111] In the above substituents A3-1 to A3-10,

[0112] a, b1 and d are each integers from 0 to 4, specifically, each integer from 0 to 2,

[0113] b and d1 are each integers from 0 to 3, specifically, they are each integers from 0 to 2,

[0114] c and e are each integers from 0 to 5, specifically, each integer from 0 to 2,

[0115] However, a+b+c+d+e≠0, and a+b1+c+d1+e≠0,

[0116] CN is a cyano group,

[0117] DB is selected from the group consisting of a dibenzofuranyl group, a dibenzothiophenyl group and a fluorenyl group, wherein the hydrogen atoms of the dibenzofuranyl group, the dibenzothiophenyl group and the fluorenyl group may each be independently substituted or unsubstituted with a deuterium (D) or a cyano group,

[0118] Cy1 to Cy4 are present or absent, and when Cy1 to Cy4 are present, they are the same or different, and each independently C6~C 30 A condensed aromatic ring or a condensed heteroaromatic ring having 5 to 30 nuclear atoms,

[0119] However, at least one of Cy1 to Cy4 is present. Here, Cy1 to Cy4 each represent a condensed ring condensed to a benzene ring in a substituent of chemical formula A1 or A2.

[0120] For example, in the above substituents A3-1 to A3-10, when Cy1 to Cy4 are present, they may be the same as or different from each other, and may be independently selected from the group consisting of the following condensed rings Cy1-1 to Cy1-9, but are not limited thereto.

[0121]

[0122] In the above condensed rings Cy1-1 to Cy1-9,

[0123] The dotted line indicates the site of condensation to the benzene ring in the substituent of chemical formula A1 or A2.

[0124] 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 6 to 13, depending on X1, X2, L1, and A described above, but is not limited thereto.

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] In the above chemical formulas 6 to 13,

[0134] n, Ar1, Ar2, a, b, b1, c, d, d1, e and R1 to R5 are each as defined in the above chemical formula 1.

[0135] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 200 below, but is not limited thereto.

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] In the present invention, the "number of nuclear atoms" refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons in the ring, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0150] 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.

[0151] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0156] 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.

[0157] 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.

[0158] In addition, in the present invention, “arylphosphinyl group” means a phosphine group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0159] In the present invention, “arylphosphine oxide group” means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphine oxide groups.

[0160] 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.

[0161] 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.

[0162]

[0163] Organic electroluminescent devices

[0164] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0165] 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.

[0166] The organic layer (300) of one or more layers may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport auxiliary layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layers (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be at least one of an electron transport layer (340) and an electron transport auxiliary layer (360).

[0167] According to an example, the organic material layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound of the above chemical formula 1, and can also move quickly from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0168] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0169] In the present invention, the electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of the electron transport material that can be used include an oxazole compound, an isoxazole compound, a triazole compound, an isothiazole compound, an oxadiazole compound, a thiadiazole compound, a perylene compound, and an aluminum complex (e.g., Alq). 3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or in combination of two or more.

[0170] 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.

[0171] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound of the chemical formula 1 has a high triplet energy. Therefore, when the compound of the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer increases, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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).

[0176] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the light-emitting layer (330), the electron transport layer (340), or the electron transport auxiliary layer (360)] includes a compound represented by the chemical formula 1.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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.

[0181] In addition, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and conventional materials known in the art can be used.

[0182]

[0183] 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.

[0184] [Preparation Example 1] Synthesis of 2-(4-chloronaphthalen-1-yl)-4,6-diphenylpyrimidine

[0185]

[0186] 2-chloro-4,6-diphenylpyrimidine 30.0g(112.47mmol), (4-chloronaphthalen-1-yl)boronic acid 25.54g(123.72mmol), Pd(PPh3) 46.50g(5.62mmol), K2CO3 31.09g(224.95mmol) were added to 1,4-dioxane 450ml and H2O 150ml, and the mixture was heated and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 31.1 g (yield 70.38%) of the target compound of Preparation Example 1.

[0187] 1H-NMR: δ 8.95(d, 1H), 8.26(d, 1H), 8.23(s, 1H), 7.96(d, 1H), 7.94(d, 4H), 7.73(d, 1H), 7.61(t, 1H), 7.57(t, 1H), 7.55(d, 4H), 7.49(t, 2H)

[0188] Mass: [(M+H) + ] : 393

[0189]

[0190] [Preparation Example 2] Synthesis of 2-(5-chloronaphthalen-2-yl)-4,6-diphenylpyrimidine

[0191]

[0192] 2-chloro-4,6-diphenylpyrimidine 30.0g(112.47mmol), (5-chloronaphthalen-2-yl)boronic acid 25.54g(123.72mmol), Pd(PPh3) 46.50g(5.62mmol), K2CO3 31.09g(224.95mmol) were added to 1,4-dioxane 450ml and H2O 150ml, and heated and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 31.7 g (yield 71.73%) of the target compound of Preparation Example 2.

[0193] 1H-NMR: δ 8.73(d, 1H), 8.23(s, 1H), 8.19(d, 1H), 8.16(d, 1H), 8.03(d, 1H), 7.94(d, 4H), 7.55(t, 4H), 7.49(t, 2H), 7.54(d, 1H), 7.34(t, 1H)

[0194] Mass: [(M+H) + ] : 393

[0195]

[0196] [Preparation Example 3] Synthesis of 4-(5-chloronaphthalen-1-yl)-2,6-diphenylpyrimidine

[0197]

[0198] 4-chloro-2,6-diphenylpyrimidine 30.0 g (112.47 mmol), (5-chloronaphthalen-1-yl)boronic acid 25.54 g (123.72 mmol), Pd(PPh3) 46.50 g (5.62 mmol), and K2CO3 31.09 g (224.95 mmol) were added to 1,4-dioxane 450 ml and H2O 150 ml, and the mixture was heated and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 33.3 g (yield 75.36%) of the target compound of Preparation Example 3.

[0199] 1H-NMR: δ 8.85(d, 1H), 8.36(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.13(d, 1H), 8.10(t, 1H), 7.94(d, 2H), 7.54(m, 3H), 7.49(m, 4H), 7.34(t, 1H)

[0200] Mass: [(M+H) + ] : 393

[0201]

[0202] [Preparation Example 4] Synthesis of 4-(4-chloronaphthalen-2-yl)-2,6-diphenylpyrimidine

[0203]

[0204] 4-chloro-2,6-diphenylpyrimidine 30.0g(112.47mmol), (4-chloronaphthalen-2-yl)boronic acid 25.54g(123.72mmol), Pd(PPh3) 46.50g(5.62mmol), K2CO3 31.09g(224.95mmol) were added to 1,4-dioxane 450ml and H2O 150ml, and the mixture was heated and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 32.8 g (yield 74.22%) of the target compound of Preparation Example 4.

[0205] 1H-NMR: δ 8.35(d, 2H), 8.26(d, 1H), 8.23(s, 1H), 8.13(d, 1H), 8.06(s, 1H), 7.94(d, 2H), 7.88(s, 1H), 7.55(m, 4H), 7.49(m, 4H)

[0206] Mass: [(M+H) + ] : 393

[0207]

[0208] [Preparation Example 5] Synthesis of 4-(5-chloronaphthalen-2-yl)-2,6-diphenylpyrimidine

[0209]

[0210] 4-chloro-2,6-diphenylpyrimidine 30.0g(112.47mmol), (5-chloronaphthalen-2-yl)boronic acid 25.54g(123.72mmol), Pd(PPh3) 46.50g(5.62mmol), K2CO3 31.09g(224.95mmol) were added to 1,4-dioxane 450ml and H2O 150ml and heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 31.1 g (yield 70.38%) of the target compound of Preparation Example 5.

[0211] 1H-NMR: δ 8.73(d,1H), 8.35(d, 2H), 8.19(d, 1H), 8.16(s, 1H), 8.06(s, 1H), 8.03(d, 1H), 7.94(d, 2H), 7.88(s, 1H), 7.54(m, 3H), 7.49(m, 4H)

[0212] Mass: [(M+H) + ] : 393

[0213]

[0214] [Preparation Example 6] Synthesis of 4-(3-chloronaphthalen-1-yl)-2,6-diphenylpyrimidine

[0215]

[0216] 4-chloro-2,6-diphenylpyrimidine 30.0g(112.47mmol), (3-chloronaphthalen-1-yl)boronic acid 25.54g(123.72mmol), Pd(PPh3) 46.50g(5.62mmol), K2CO3 31.09g(224.95mmol) were added to 1,4-dioxane 450ml and H2O 150ml, and the mixture was heated and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 32.5 g (yield 73.55%) of the target compound of Preparation Example 6.

[0217] 1H-NMR: δ 8.87(s,1H), 8.35(d, 2H), 8.23(s, 1H), 8.15(d, 1H), 7.94(d, 2H), 7.90(s, 1H), 7.82(s, 1H), 7.54(m, 3H), 7.49(m, 5H)

[0218] Mass: [(M+H) + ] : 393

[0219]

[0220] [Synthesis Example 1] Synthesis of Compound 1

[0221]

[0222] 2-chloro-4,6-diphenylpyrimidine 8.0 g (29.99 mmol), [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-3'''-ylboronic acid 14.07 g (32.99 mmol), Pd(PPh3) 41.73 g (1.50 mmol), and K2CO3 8.29 g (59.99 mmol) were added to 120 ml of 1,4-dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 14.7 g (yield 79.82%) of compound 1.

[0223] 1H-NMR: δ 8.23(s,1H), 8.06(d, 2H), 7.94(m, 8H), 7.83(t, 1H), 7.79(d, 2H), 7.65(d, 2H), 7.60(t, 4H), 7.55(t, 6H), 7.49(t, 2H), 7.46(t, 2H), 7.41(t, 2H)

[0224] Mass: [(M+H) + ] : 613

[0225]

[0226] [Synthesis Example 2] Synthesis of Compound 5

[0227]

[0228] 4-chloro-2,6-diphenylpyrimidine 6.0g(22.49mmol), [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'''-ylboronic acid 10.55g(24.74mmol), Pd(PPh3) 41.30g(1.12mmol), K2CO3 6.22g(44.99mmol) were added to 1,4-dioxane 90ml and H2O 30ml, and the mixture was heated and refluxed for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 9.8 g of compound 5 (yield 70.37%).

[0229] 1H-NMR: δ 8.40(d,1H), 8.35(d,2H), 8.23(s, 1H), 8.15(s, 1H), 8.13(s, 1H), 7.96(d, 4H), 7.94(d, 2H), 7.79(d, 4H), 7.60(t, 4H), 7.55(t, 2H), 7.49(m, 4H), 7.46(t, 4H), 7.41(t, 2H)

[0230] Mass: [(M+H) + ] : 613

[0231]

[0232] [Synthesis Example 3] Synthesis of Compound 7

[0233]

[0234] 4-chloro-2,6-diphenylpyrimidine 6.0g(22.49mmol), [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-ylboronic acid 10.55g(24.74mmol), Pd(PPh3) 41.30g(1.12mmol), K2CO3 6.22g(44.99mmol) were added to 1,4-dioxane 90ml and H2O 30ml, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.4 g (yield 75.45%) of compound 7.

[0235] 1H-NMR: δ 8.40(s,1H), 8.35(d,2H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 4H), 7.94(d, 2H), 7.79(d, 4H), 7.60(t, 4H), 7.55(t, 2H), 7.49(m, 4H), 7.46(t, 4H), 7.41(t, 2H)

[0236] Mass: [(M+H) + ] : 613

[0237]

[0238] [Synthesis Example 4] Synthesis of Compound 11

[0239]

[0240] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine 8.0 g (23.34 mmol), [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'''-ylboronic acid 10.94 g (25.67 mmol), Pd(PPh3) 41.35 g (1.17 mmol), K2CO3 6.45 g (46.67 mmol) were added to 120 ml of 1,4-dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.3 g (yield 64.07%) of compound 11.

[0241] 1H-NMR: δ 8.40(d, 1H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 6H), 7.94(d, 2H), 7.79(d, 4H), 7.75(d, 2H), 7.60(t, 4H), 7.55(t, 2H), 7.49(d, 3H), 7.46(t, 4H), 7.41(t, 3H), 7.25(d, 2H)

[0242] Mass: [(M+H) + ] : 689

[0243]

[0244] [Synthesis Example 5] Synthesis of Compound 12

[0245]

[0246] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine 8.0 g (23.34 mmol), [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-ylboronic acid 10.94 g (25.67 mmol), Pd(PPh3) 41.35 g (1.17 mmol), K2CO3 6.45 g (46.67 mmol) were added to 120 ml of 1,4-dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 9.8 g of compound 12 (yield 68.53%).

[0247] 1H-NMR: δ 8.40(d,1H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H),

[0248] 7.96(d, 6H), 7.94(d, 2H), 7.79(d, 4H), 7.75(d, 2H), 7.60(t, 4H), 7.55(t, 2H), 7.49(d, 3H), 7.46(t, 4H), 7.41(t, 3H), 7.25(d, 2H)

[0249] Mass: [(M+H) + ] : 613

[0250]

[0251] [Synthesis Example 6] Synthesis of Compound 17

[0252]

[0253] 6.0 g (22.49 mmol) of 2-chloro-4,6-diphenylpyrimidine, 12.43 g (24.74 mmol) of (2''-([1,1'-biphenyl]-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-yl)boronic acid, 1.30 g (1.12 mmol) of Pd(PPh3)4, and 6.22 g (44.99 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.4 g (yield 67.11%) of compound 17.

[0254] 1H-NMR: δ 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 6H), 7.94(d, 4H), 7.79(d, 4H), 7.60(t, 4H), 7.55(t, 4H), 7.49(d, 2H), 7.46(t, 4H), 7.41(t, 2H), 7.35(d, 1H), 7.25(d, 2H)

[0255] Mass: [(M+H) + ] : 689

[0256]

[0257] [Synthesis Example 7] Synthesis of Compound 23

[0258]

[0259] 6.0 g (22.49 mmol) of 4-chloro-2,6-diphenylpyrimidine, 12.43 g (24.74 mmol) of (2''-([1,1'-biphenyl]-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-yl)boronic acid, 1.30 g (1.12 mmol) of Pd(PPh3) and 6.22 g (44.99 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O and heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO4 and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.8 g (yield 69.69%) of compound 23.

[0260] 1H-NMR: δ 8.35(d, 2H), 8.30(d, 2H), 8.23(d, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 4H), 7.94(d, 2H), 7.85(d, 2H), 7.79(d, 4H), 7.60(t, 4H), 7.55(t, 2H), 7.49(m, 4H), 7.46(t, 4H), 7.41(t, 2H), 7.35(d, 1H)

[0261] Mass: [(M+H) + ] : 689

[0262]

[0263] [Synthesis Example 8] Synthesis of Compound 35

[0264]

[0265] 6.0 g (17.50 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 9.67 g (19.25 mmol) of (2''-([1,1'-biphenyl]-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-yl)boronic acid, 1.01 g (0.88 mmol) of Pd(PPh3)4, and 4.84 g (35.00 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 9.9 g of compound 35 (yield 73.94%).

[0266] 1H-NMR: δ 8.30(d, 2H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 6H), 7.94(d, 2H), 7.85(d, 2H), 7.79(d, 4H), 7.75(d, 2H), 7.60(t, 4H), 7.55(t, 2H), 7.49(d, 3H), 7.46(t, 4H), 7.41(t, 3H), 7.35(d, 1H), 7.25(d, 2H)

[0267] Mass: [(M+H) + ] : 765

[0268]

[0269] [Synthesis Example 9] Synthesis of Compound 75

[0270]

[0271] 6.0 g (15.27 mmol) of the compound of Preparation Example 1, 7.16 g (16.80 mmol) of [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-ylboronic acid, 40.88 g (0.76 mmol) of Pd(PPh3), and 4.22 g (30.54 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 6.8 g of compound 75 (yield 60.26%).

[0272] 1H-NMR: δ 9.02(d, 1H), 8.95(d, 1H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 8.06(d, 1H), 7.96(d, 4H), 7.94(d, 4H), 7.79(d, 4H), 7.84(d, 1H), 7.60(t, 4H), 7.55(m, 5H), 7.49(t, 2H), 7.46(m, 5H), 7.41(t, 2H), 7.35(d, 1H)

[0273] Mass: [(M+H) + ] : 739

[0274]

[0275] [Synthesis Example 10] Synthesis of Compound 119

[0276]

[0277] 2-chloro-4,6-diphenylpyrimidine 6.0g(22.49mmol), (4-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'''-yl)boronic acid 11.17g(24.74mmol), Pd(PPh3) 41.30g(1.12mmol), K2CO3 6.22g(44.99mmol) were added to 1,4-dioxane 90ml and H2O 30ml, and heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 9.4 g (yield 65.52%) of compound 119.

[0278] 1H-NMR: δ 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 8.06(d, 1H), 7.96(d, 4H), 7.94(d, 4H), 7.79(d, 2H), 7.84(d, 4H), 7.60(t, 4H), 7.55(d, 4H), 7.49(t, 2H), 7.46(t, 2H), 7.41(t, 2H)

[0279] Mass: [(M+H) + ] : 638

[0280]

[0281] [Synthesis Example 11] Synthesis of Compound 122

[0282]

[0283] 6.0 g (22.49 mol) of 4-chloro-2,6-diphenylpyrimidine, 11.17 g (24.74 mmol) of (5'-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)boronic acid, 11.17 g (24.74 mmol) of Pd(PPh3)4, and 6.22 g (44.99 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.1 g (yield 70.40%) of compound 122.

[0284] 1H-NMR: δ 8.40(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.15(d, 1H), 8.14(d, 1H), 8.13(s, 1H), 8.04(s, 1H), 7.96(d, 2H), 7.94(d, 2H), 7.92(d, 1H), 7.79(d, 4H), 7.60(t, 2H), 7.55(t, 2H), 7.49(m, 4H), 7.46(t, 4H), 7.41(t, 2H)

[0285] Mass: [(M+H) + ] : 638

[0286]

[0287] [Synthesis Example 12] Synthesis of Compound 125

[0288]

[0289] 6.0 g (17.5 mol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine, 8.69 g (19.25 mmol) of (3-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'''-yl)boronic acid, 1.01 g (0.88 mmol) of Pd(PPh3)4, and 4.84 g (35.00 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 8.8 g (yield 70.43%) of compound 125.

[0290] 1H-NMR: δ 8.40(d, 1H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 8.02(d, 1H), 7.96(d, 6H), 7.94(d, 2H), 7.85(s, 1H), 7.79(d, 3H), 7.75(d, 2H), 7.72(t, 1H), 7.60(t, 4H), 7.55(t, 2H), 7.49(t, 3H), 7.46(t, 2H), 7.41(t, 2H), 7.25(d, 2H)

[0291] Mass: [(M+H) + ] : 714

[0292]

[0293] [Synthesis Example 13] Synthesis of Compound 131

[0294]

[0295] 6.0 g (17.50 mol) of 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine, 10.15 g (19.25 mmol) of (2''-(5-cyano-[1,1'-biphenyl]-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4'''-yl)boronic acid, 1.01 g (0.88 mmol) of Pd(PPh3)4, and 4.84 g (35.00 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 10.0 g (yield 72.33%) of compound 131.

[0296] 1H-NMR: δ 8.30(d, 2H), 8.23(s, 1H), 8.15(d, 1H), 8.14(d, 1H), 8.13(s, 1H), 8.04(s, 1H), 7.96(d, 4H), 7.94(d, 2H), 7.92(d, 1H), 7.85(d, 2H), 7.79(d, 4H), 7.75(d, 2H), 7.60(t, 2H), 7.55(t, 2H), 7.49(t, 3H), 7.46(t, 4H), 7.41(t, 3H), 7.35(d, 1H), 7.25(d, 2H)

[0297] Mass: [(M+H) + ] : 790

[0298]

[0299] [Synthesis Example 14] Synthesis of Compound 134

[0300]

[0301] 6.0 g (15.27 mol) of the compound of Preparation Example 2, 7.58 g (16.80 mmol) of (3-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'-yl)boronic acid, 40.88 g (0.76 mmol) of Pd(PPh3), and 4.22 g (30.54 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 7.9 g (yield 67.72%) of compound 134.

[0302] 1H-NMR: δ 8.50(d, 1H), 8.29(d, 1H), 8.23(s, 2H), 8.15(d, 1H), 8.13(s, 1H), 8.09(d, 1H), 8.02(d, 2H), 7.96(d, 4H), 7.94(d, 4H), 7.85(s, 1H), 7.79(d, 3H), 7.77(t, 1H), 7.72(t, 1H), 7.60(t, 4H), 7.55(t, 4H), 7.49(t, 2H), 7.46(t, 2H), 7.41(t, 1H), 7.35(d, 1H)

[0303] Mass: [(M+H) + ] : 764

[0304]

[0305] [Synthesis Example 15] Synthesis of Compound 138

[0306]

[0307] 6.0 g (15.27 mol) of the compound of Preparation Example 3, 7.58 g (16.80 mmol) of (4''''-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'-yl)boronic acid, 40.88 g (0.76 mmol) of Pd(PPh3), and 4.22 g (30.54 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 8.1 g (yield 69.43%) of compound 138.

[0308] 1H-NMR: δ 9.06(d, 1H), 8.90(d, 1H), 8.50(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.97(m, 5H), 7.94(m, 3H), 7.85(d, 4H), 7.79(d, 2H), 7.77(t, 1H), 7.60(t, 4H), 7.55(t, 2H), 7.49(m, 4H), 7.46(t, 2H), 7.41(t, 1H), 7.35(d, 1H)

[0309] Mass: [(M+H) + ] : 764

[0310]

[0311] [Synthesis Example 16] Synthesis of Compound 140

[0312]

[0313] 6.0 g (15.27 mol) of the compound of Preparation Example 4, 7.58 g (16.80 mmol) of (2-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'''-yl)boronic acid, 40.88 g (0.76 mmol) of Pd(PPh3), and 4.22 g (30.54 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 8.1 g (yield 70.28%) of compound 140.

[0314] 1H-NMR: δ 8.95(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.20(d, 1H), 8.15(d, 1H), 8.13(s, 2H), 7.96(d, 4H), 7.94(m, 3H), 7.79(m, 4H), 7.73(t, 1H), 7.71(s, 1H), 7.60(t, 4H), 7.55(t, 2H), 7.52(t, 1H), 7.49(m, 4H), 7.46(t, 2H), 7.41(t, 1H), 7.39(t, 1H), 7.35(d, 1H)

[0315] Mass: [(M+H) + ] : 764

[0316]

[0317] [Synthesis Example 17] Synthesis of Compound 141

[0318]

[0319] 6.0 g (15.27 mol) of the compound of Preparation Example 5, 7.58 g (16.80 mmol) of (4''''-cyano-[1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4'-yl)boronic acid, 40.88 g (0.76 mmol) of Pd(PPh3), and 4.22 g (30.54 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 8.9 g (yield 76.29%) of compound 141.

[0320] 1H-NMR: δ 8.50(d, 1H), 8.35(d, 2H), 8.29(d, 1H), 8.23(s, 2H), 8.15(d, 1H), 8.13(s, 1H), 8.09(d, 1H), 8.03(d, 1H), 7.96(d, 4H), 7.94(d, 2H), 7.84(d, 4H), 7.79(d, 2H), 7.77(t, 1H), 7.60(t, 4H), 7.55(t, 2H), 7.50(m, 4H), 7.46(t, 2H), 7.41(t, 1H), 7.35(d, 1H)

[0321] Mass: [(M+H) + ] : 764

[0322]

[0323] [Synthesis Example 18] Synthesis of Compound 142

[0324]

[0325] 2-chloro-4,6-diphenylpyrimidine 6.0g (22.49 mol), [1,1':2',1'':2'',1''':2''',1'''':4'''',1'''''-sexiphenyl]-3'''-ylboronic acid 12.43g (24.74 mmol), Pd(PPh3)41.30g (1.12 mmol), K2CO36.22g (44.99 mmol) were added to 1,4-dioxane 90ml and H2O 30ml, and the mixture was heated and refluxed for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, then MgSO4 was added to remove moisture, and then filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 11.9 g (yield 76.79%) of compound 142.

[0326] 1H-NMR: δ 8.23(s, 1H), 8.06(d, 2H), 7.96(d, 4H), 7.94(d, 4H), 7.84(d, 1H), 7.79(d, 2H), 7.75(d, 2H), 7.60(t, 4H), 7.55(t, 4H), 7.49(d, 4H), 7.46(t, 2H), 7.41(t, 2H), 7.25(d, 4H)

[0327] Mass: [(M+H) + ] : 689

[0328]

[0329] [Synthesis Example 19] Synthesis of Compound 158

[0330]

[0331] 2-(3-chlorophenyl)-4,6-diphenylpyrimidine 6.0 g (17.50 mol), (6''-([1,1'-biphenyl]-2-yl)-[1,1':2',1'':3'',1'''-quaterphenyl]-4'''-yl)boronic acid 9.67 g (19.25 mmol), Pd(OAc)2 0.12 g (0.53 mmol), Xphos 0.5 g (1.05 mmol), Cs2CO3 11.40 g (35.00 mmol) were added to 80 ml of toluene, 20 ml of EtOH, and 20 ml of H2O, and heated under reflux for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtration, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 9.3 g of compound 158 (yield 69.47%).

[0332] 1H-NMR: δ 8.38(d, 1H), 8.23(s, 1H), 8.15(d, 1H), 8.13(s, 1H), 7.96(d, 4H), 7.94(d, 5H), 7.79(d, 4H), 7.73(d, 1H), 7.60(m, 5H), 7.55(t, 4H), 7.49(t, 2H), 7.46(t, 4H), 7.41(t, 2H), 7.35(d, 1H), 7.25(d, 4H)

[0333] Mass: [(M+H) + ] : 765

[0334]

[0335] [Synthesis Example 20] Synthesis of Compound 188

[0336]

[0337] 6.0 g (15.06 mmol) of the compound of Preparation Example 6, 7.06 g (16.57 mmol) of [1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-ylboronic acid, 40.87 g (0.75 mmol) of Pd(PPh3), and 4.16 g (30.13 mmol) of K2CO3 were added to 90 ml of 1,4-dioxane and 30 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and then MgSO4 was added to remove moisture and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 7.0 g of compound 188 (yield 62.88%).

[0338] 1H-NMR: δ 9.03(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.14(m, 4H), 7.96(d, 4H), 7.94(d, 2H), 7.82(s, 1H), 7.79(d, 4H), 7.60(m, 5H), 7.55(m, 3H), 7.49(m, 4H), 7.46(t, 4H), 7.41(t, 2H), 7.35(d, 1H)

[0339] Mass: [(M+H) + ] : 739

[0340]

[0341] [Example 1] Fabrication of a blue organic electroluminescent device

[0342] Compound 119 synthesized in Synthesis Example 10 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following process.

[0343] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0344] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / compound 119 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. The structures of HI, HAT-CN6, EB, BH, BD, and Liq used here are as follows, respectively.

[0345]

[0346]

[0347] [Examples 2 to 10] Preparation of blue organic electroluminescent devices

[0348] 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 119 used as an electron transport layer material in Example 1.

[0349]

[0350] [Comparative Examples 1 to 6] Manufacturing of blue organic electroluminescent devices

[0351] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3, HB-1, HB-2, HB-3, ET-1, and ET-2 were used instead of compound 119 used as an electron transport layer material in Example 1.

[0352] At this time, the structures of Alq3, HB-1, HB-2, HB-3, ET-1, and ET-2 used are as follows, respectively.

[0353]

[0354]

[0355] [Evaluation Example 1]

[0356] For the organic electroluminescent devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 6, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0357] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 1193.94547.0 Example 2 Compound 1223.84547.2 Example 3 Compound 1253.94537.0 Example 4 Compound 1313.64547.6 Example 5 Compound 1343.74547.6 Example 6 Compound 1383.54537.8 Example 7 Compound 1403.64557.8 Example 8 Compound 1413.44558.0 Example 9 Compound 1423.94547.0 Example 10 Compound 1583.84547.2 Comparative Example 1Alq35.04575.8Comparative Example 2HB-14.84556.0Comparative Example 3HB-24.84566.2Comparative Example 4HB-34.64556.2Comparative Example 5ET-14.44546.4Comparative Example 6ET-24.24556.6

[0358] As shown in Table 1, it was confirmed that the organic electroluminescent devices of Examples 1 to 10 had superior driving voltage, luminescence peak, and current efficiency compared to the organic electroluminescent devices of Comparative Examples 1 to 6, respectively.

[0359]

[0360] [Example 11] Fabrication of a blue organic electroluminescent device

[0361] Compound 1 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 according to the following process.

[0362] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0363] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / Compound 1 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, and Liq used are the same as those described in Example 1, and the structure of ET is as follows.

[0364]

[0365]

[0366] [Examples 12 to 20] Preparation of blue organic electroluminescent devices

[0367] A blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that each compound described in Table 2 below was used instead of Compound 1 used as an electron transport auxiliary layer material in Example 11.

[0368]

[0369] [Comparative Example 7]

[0370] A blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that compound 1, which was used as an electron transport auxiliary layer material in Example 11, was not used.

[0371]

[0372] [Comparative Examples 8 to 12] Manufacturing of blue organic electroluminescent devices

[0373] A blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that HB-1, HB-2, HB-3, ET-1, and ET-2 were used instead of compound 1 used as an electron transport auxiliary layer material in Example 11. The structures of HB-1, HB-2, HB-3, ET-1, and ET-2 used here are the same as those described in Comparative Example 1.

[0374]

[0375] [Evaluation Example 2]

[0376] For the organic electroluminescent devices manufactured in Examples 11 to 20 and Comparative Examples 7 to 12, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0377] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 11 Compound 13.74547.5 Example 12 Compound 53.64547.6 Example 13 Compound 73.64557.6 Example 14 Compound 113.84557.3 Example 15 Compound 123.74547.4 Example 16 Compound 173.64557.6 Example 17 Compound 233.64557.5 Example 18 Compound 353.54547.7 Example 19 Compound 753.34557.9 Example 20 Compound 1883.74557.6 Comparative Example 7-5.04565.8Comparative Example 8HB-14.44576.4Comparative Example 9HB-24.24566.6Comparative Example 10HB-34.04556.8Comparative Example 11ET-14.74566.0Comparative Example 12ET-24.64556.2

[0378] As shown in Table 2, it was confirmed that the organic electroluminescent devices of Examples 11 to 20 had superior driving voltage, luminescence peak, and current efficiency compared to the organic electroluminescent devices of Comparative Examples 7 to 12, respectively.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, One of X1 and X2 is N, and the other is C(Ar3), Ar1 and Ar2 are the same or different from each other, and are each independently C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, Ar3 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, n is an integer from 0 to 3, L1 is a single bond, or C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, A is a substituent represented by the following chemical formula A1 or A2, [Chemical Formula A1] [Chemical Formula A2] In the above chemical formulas A1 and A2, * is a part that is combined with the above chemical formula 1, a, b1 and d are each integers from 0 to 4, b and d1 are integers from 0 to 3, respectively. c and e are integers from 0 to 5, respectively. R1 to R5 are the same or different and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 to Ar3, 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, arylphosphine oxide group, arylamine group and condensed ring of the above R1 to R5 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, Amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (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 chemical formula 1 above The moiety is a compound of the following moiety Mo1-1 or Mo1-2: (In the above moieties Mo1-1 and Mo1-2, Ar1 to Ar3 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 2 to 5: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] (In the above chemical formulas 2 to 5, n, L1, Ar1 to Ar3, a, b, b1, c, d, d1, e and R1 to R5 are each as defined in Article 1).

4. In paragraph 1, A compound wherein the above Ar1 and Ar2 are the same or different from each other and are each independently selected from the group consisting of the following substituents S1-1 to S1-18: (In the above substituents S1-1 to S1-18, f is an integer from 0 to 5, g is an integer from 0 to 4, h is an integer from 0 to 7, i is an integer from 0 to 6, j is an integer from 0 to 9, k is an integer from 0 to 8, l is an integer from 0 to 3, Ar4 and Ar5 are the same or different from each other, and are each independently C1~C 12 Alkyl group and C6~C 18 is selected from the group consisting of aryl groups, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

5. In paragraph 1, wherein the above L1 is a single bond, or a compound of the following linker group L1-1 or L1-2: (In the above linkers L1-1 and L1-2, o is an integer from 0 to 4, p is an integer from 0 to 6, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (selected from the group consisting of arylamine groups).

6. In paragraph 1, A compound wherein A is selected from the group consisting of the following substituents A3-1 to A3-10: (In the above substituents A3-1 to A3-10, a, b1 and d are each integers from 0 to 4, b and d1 are integers from 0 to 3, respectively. c and e are integers from 0 to 5, respectively. However, a+b+c+d+e≠0, and a+b1+c+d1+e≠0, CN is cyano group, DB is selected from the group consisting of a dibenzofuranyl group, a dibenzothiophenyl group and a fluorenyl group, wherein the hydrogens of the dibenzofuranyl group, the dibenzothiophenyl group and the fluorenyl group may each be independently substituted or unsubstituted with a deuterium (D) or a cyano group, Cy1 to Cy4 are present or absent, and when Cy1 to Cy4 are present, they are each independently C6~C 30 A condensed aromatic ring or a condensed heteroaromatic ring having 5 to 30 nuclear atoms, However, at least one of Cy1 to Cy4 is present).

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 6 to 13: [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] (In the above chemical formulas 6 to 13, n, Ar1, Ar2, a, b, b1, c, d, d1, e and R1 to R5 are each as defined in Article 1).

8. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 200 below: .

9. Anode; cathode; comprising at least one organic layer interposed between the anode and cathode, An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises an organic compound according to any one of claims 1 to 8.

10. In paragraph 9, An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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