Organic compound and organic electroluminescent device using 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 that exhibits excellent electron transport ability, heat resistance, carrier transport capability, and luminescence, and an organic electroluminescent device in which the organic compound is included in one or more organic layers, thereby improving properties such as emission efficiency, driving voltage, and lifespan.

Description

Organic compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound 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 into the organic layer 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] Luminescent materials can be categorized into blue, green, and red luminescent materials based on their luminescent color, as well as yellow and orange luminescent materials for better natural color reproduction. Furthermore, host / dopant systems can be used as luminescent materials to enhance color purity and luminescence efficiency through energy transfer.

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

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

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

[0007] The present invention aims to provide a novel compound having excellent electron injection and transport ability, thermal stability, carrier transport ability, luminescence ability, etc., and which can be used as an organic layer material of an organic electroluminescent device, specifically, as a luminescent layer material, a life-span improving layer material, a luminescent auxiliary layer material, an electron transport layer material or an electron transport auxiliary layer material, and more specifically, as an electron transport layer material or an electron transport auxiliary layer material.

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

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

[0010]

[0011] (In the above chemical formula 1,

[0012] Z1 to Z3 are the same or different, and are each independently N or C(Ar3), provided that at least two of Z1 to Z3 are N;

[0013] 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,

[0014] L1 is a linker group represented by the following chemical formula L1-1 or L1-2,

[0015] [Chemical formula L1-1]

[0016]

[0017] [Chemical formula L1-2]

[0018]

[0019] In the above chemical formulas L1-1 and L1-2,

[0020] The dotted lines indicate the presence or absence of each ring.

[0021] Cy1 to Cy3 are the same or different, and each is a six-membered aromatic ring.

[0022] a, c, d, and e are each integers from 0 to 6,

[0023] b is an integer from 0 to 5.

[0024] 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 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups to form a condensed ring,

[0025] X1 is O, S, C(Ar4)(Ar5), N(Ar6) and is selected from the group consisting of;

[0026] Ar3 to Ar8 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, nitro, amino, hydroxyl, 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~C40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups 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, arylamine group and condensed ring of the above Ar1 to Ar8 and R1 to R5 are each independently each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, 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 a compound represented by the aforementioned chemical formula 1.

[0029] In one example, the organic layer containing the compound may be an electron transport layer or an electron transport auxiliary layer.

[0030] Since the compound of the present invention has excellent electron transport ability, electrochemical stability, thermal stability, etc., it can be used as an organic layer material of an organic electroluminescent device. In particular, when the compound of the present invention is used as an electron transport layer material or an electron transport auxiliary layer material, it is possible to manufacture an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, and long lifespan characteristics compared to conventional materials, and further, it is possible to manufacture a full-color display panel with improved performance and lifespan.

[0031] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0032] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0033] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0034] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0035] <Explanation of symbols>

[0036] 100: anode, 200: cathode,

[0037] 300: Organic layer, 310: Hole injection layer,

[0038] 320: hole transport layer, 330: light emitting layer,

[0039] 340: electron transport layer, 350: electron injection layer,

[0040] 360: Electron transport auxiliary layer

[0041] Hereinafter, the present invention will be described.

[0042] <New organic compounds>

[0043] The present invention is a compound represented by the above chemical formula 1, which has excellent electron injection and transport ability, electrochemical stability, thermal stability, carrier transport ability, and luminescence ability, and can be used as a high-efficiency organic layer material, particularly an electron transport layer material or an electron transport auxiliary layer material.

[0044] Specifically, the organic compound according to the present invention has a structure in which a nitrogen-containing heteroaromatic ring (Z1 to Z3-containing ring) moiety and a dibenzo moiety (X1-containing ring moiety) are connected via a terphenylene group, which is a linker group (L1).

[0045] However, in the present invention, the terphenylene group, which is the linker group (L1), may itself contain an ortho-bond, or may link a nitrogen-containing heteroaromatic ring moiety to the first benzene ring of the terphenylene group in an ortho-bond position, or may link a dibenzo moiety to the third benzene ring of the terphenylene group in an ortho-bond position. Specifically, the terphenylene group, which is the linker group (L1), may be an ortho-terphenylene group (e.g., a linker group of chemical formula L-1). Alternatively, the nitrogen-containing heteroaromatic ring moiety may be bonded to the 2nd carbon position of the first benzene ring of the terphenylene group, which is ortho-positioned based on the central (second) benzene ring of the terphenylene group, or the dibenzo moiety may be bonded to the 2nd carbon position of the third benzene ring of the terphenylene group, which is ortho-positioned based on the central (second) benzene ring of the terphenylene group. That is, the portion that is connected to another moiety may be a terphenylene group (e.g., a linker group of chemical formula L-2) that is an ortho-bonding position based on the central (second) benzene ring. In this way, in the compound of the present invention, the nitrogen-containing heteroaromatic ring moiety and the dibenzo moiety may be connected by at least one ortho-bonding centered on the terphenylene group, which is the linker group (L1). As a result, the compound of the present invention may induce delocalization of the LUMO orbital, thereby improving the electron transport property. In addition, the compound of the present invention can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer by maximizing steric hindrance and inducing an increase in triplet energy, thereby increasing the number of excitons contributing to light emission, thereby improving the light-emitting efficiency of the device, and enhancing the durability and electrochemical stability of the device, thereby efficiently increasing the lifespan of the device. In addition, an organic electroluminescent device to which the compound of the present invention is applied can realize low-voltage operation.

[0046] In addition, the compound of the present invention can improve the stability of the molecule because the electron donating ability of the dibenzo moiety can be improved through the effect of increasing electron density by introducing an electron donating group (EDG) with weak electron donating ability, such as a phenyl group, at the end of the dibenzo moiety.

[0047] In addition, the compound of the present invention can significantly increase its molecular weight by introducing various substituents (e.g., alkyl group, aryl group, heteroaryl group, etc.) into the nitrogen-containing heteroaromatic ring moiety, thereby increasing the glass transition temperature and improving thermal safety and electrochemical stability.

[0048] As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron transport ability, thermal stability, electrochemical stability, etc., and can be applied as an organic layer material of an organic electroluminescent device, preferably an emitting layer material (a blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, a life-span improvement layer material, an electron transport auxiliary layer material, and more preferably an electron transport layer material or an electron transport auxiliary layer material. In this case, the performance and life-span characteristics of the organic electroluminescent device can be greatly improved, and the performance of a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also be maximized.

[0049]

[0050] In the chemical formula 1 according to the present invention, Z1 to Z3 are the same or different, and are each independently N or C(Ar3), provided that at least two of Z1 to Z3 are N. The Z1 to Z3-containing ring moiety is a type of nitrogen-containing heteroaromatic ring, and may be a monocyclic nitrogen-containing heteroaryl group (e.g., an azine group) containing at least two nitrogen atoms. In this way, by including a heteroaromatic ring moiety containing 2 to 3 nitrogens, the compound of the chemical formula 1 according to the present invention may exhibit better electron absorption properties, which may be advantageous for electron injection and transport.

[0051] According to an example, the Z1 to Z3-containing ring moiety ( The moiety) may be any one of the following moieties Az1-1 to Az1-3, but is not limited thereto.

[0052]

[0053] In the above moieties Az-1 to Az-3,

[0054] * is a part connected to the above chemical formula 1,

[0055] Ar1, Ar2 and Ar3 are each as defined in the above chemical formula 1.

[0056] In another example, Z1 to Z3 can all be N. That is, the Z1 to Z3-containing ring moiety can be the moiety Az-3.

[0057] In the above chemical formula 1, Ar1 and Ar2 are the same or different from each other, and each independently represents C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 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~C60 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, specifically C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0058] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~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, 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.

[0059] In one example, Ar1 and Ar2 are the same or different from each other, and each independently represent deuterium (D), 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, an anthryl group, a pyrenyl group, a pyridyl, 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, It can be selected from the group consisting of a phenanthrolinyl group and a carbazolyl group.

[0060] 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 S1-1 to S1-10, but are not limited thereto.

[0061]

[0062] In the above substituents S1-1 to S1-10,

[0063] X2 is O, S, C(Ar9)(Ar 10 ), Si(Ar 11 )(Ar 12 ) and N(Ar 13 ) is selected from the group consisting of,

[0064] Ar9 to Ar 13 are identical or different from each other, and each independently represents deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 selected from the group consisting of arylamine groups, or adjacent groups (e.g. R8-R9, R 10 -R 11 , R8-R, R 10 -R, R 12 -R) to form a condensed ring, and specifically, each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group having 5 to 60 nuclear atoms, C6~C30 Arylphosphine oxide group and C6~C 30 is selected from the group consisting of an arylamine group, or can form a condensed ring by condensation with an adjacent group, and more specifically, is selected from the group consisting of a deuterium (D), a cyano group (-CN), 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 and a naphthyl group, or can form a condensed ring by condensation with an adjacent group,

[0065] f is an integer from 0 to 5,

[0066] g is an integer from 0 to 4,

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

[0068] i is an integer from 0 to 6,

[0069] j is an integer from 0 to 9,

[0070] k is an integer from 0 to 8,

[0071] Multiple R's are the same or different from each other,

[0072] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 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), 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 may be selected from the group consisting of arylamine groups. 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.

[0073] 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 S1 to S26, but are not limited thereto.

[0074]

[0075]

[0076] In the above chemical formula 1, Ar3 is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups (e.g., Ar3-Ar1, Ar3-Ar2, etc.) to form a condensed ring, and specifically, each group is selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~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 selected from the group consisting of arylamine groups, or may be condensed with adjacent groups (e.g., Ar3-Ar1, Ar3-Ar2, etc.) 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.

[0077] For example, Ar3 is hydrogen, deuterium (D), cyano group (-CN), 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.

[0078] According to another example, Ar3 can be selected from the group consisting of hydrogen, deuterium (D), cyano group (-CN), and the substituents S1-1 to S1-10.

[0079] In another example, Ar3 may be hydrogen or may be selected from the group consisting of substituents S1 to S26.

[0080] In the chemical formula 1 according to the present invention, the above-described nitrogen-containing heteroaromatic ring moiety is connected to a dibenzo moiety via a linker group (L1). At this time, the linker group (L1) connects the nitrogen-containing heteroaromatic ring moiety and the dibenzo moiety with at least one ortho-bond around it, and may be a linker group represented by the chemical formula L1-1 or L1-2. For example, the linker group (L1) may be an ortho-terpenylene group. Alternatively, the linker group (L1) may be a terphenylene group in which the portion connected to another moiety is an ortho-bond position based on the central (second) benzene ring. Specifically, the nitrogen-containing heteroaromatic ring moiety may be bonded to the 2nd position of the first benzene ring of the terphenylene group, which is ortho-positioned based on the central (second) benzene ring of the terphenylene group, or the dibenzo moiety may be bonded to the 2nd position of the third benzene ring of the terphenylene group, which is ortho-positioned based on the central (second) benzene ring of the terphenylene group. For example, the nitrogen-containing heteroaromatic ring moiety and the dibenzo moiety may be bonded to each other with the terphenylene group as the center in (i) an ortho-(meta or para)-(meta or para) bond, (ii) a (meta or para)-(meta or para)-ortho bond, (iii) an ortho-(meta or para)-ortho bond, or (iv) a (ortho-meta or para)-ortho-(ortho-meta or para) bond.

[0081] In the linker group represented by the above chemical formula L1-1 or L1-2, the dotted line indicates the presence or absence of each ring, and Cy1 to Cy3 are aromatic rings condensed with a benzene ring, which are the same or different from each other, and each is a 6-membered aromatic ring. When each of Cy1 to Cy3 is present, the linker group can contain naphthalene.

[0082] In the linker group represented by the above chemical formula L1-1 or L1-2, c, d and e are each an integer of 0 to 6, specifically, each may be an integer of 0 to 3, and more specifically, may be 0 or 1.

[0083] Here, when c is 0, it means that hydrogen is not substituted with the substituent R3, when d is 0, it means that hydrogen is not substituted with the substituent R4, and when e is 0, it means that hydrogen is not substituted with the substituent R3. On the other hand, when c is an integer from 1 to 6, it means that hydrogen is not substituted with the substituent R3, when d is an integer from 1 to 6, it means that hydrogen is not substituted with the substituent R4, and when e is 1 to 6, it means that hydrogen is not substituted with the substituent R5.

[0084] At this time, multiple R3s are the same or different from each other, multiple R4s are the same or different from each other, and multiple R5s are the same or different from each other.

[0085] The above R3 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), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups (e.g. R3-R3, R4-R4, R5-R5, R3-R4, R4-R5, etc.) to form a condensed ring, and specifically hydrogen, deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C3~C 20 Cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclear atoms, C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0086] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of R3 to R5 are each independently independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C60 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.

[0087] For example, the L1 may be a linker group represented by any one of the following chemical formulas L2-1 to L2-5, but is not limited thereto.

[0088] [Chemical formula L2-1]

[0089]

[0090] [Chemical formula L2-2]

[0091]

[0092] [Chemical formula L2-3]

[0093]

[0094] [Chemical formula L2-4]

[0095]

[0096] [Chemical formula L2-5]

[0097]

[0098] In the above chemical formulas L2-1 to L2-5,

[0099] * is a part connected to the above chemical formula 1,

[0100] Cy1 to Cy3, c, d, e, R3 to R4 are each as defined in the above chemical formula 1.

[0101] Depending on the bonding relationship within the aforementioned linker group (L1), the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 20. However, the present invention is not limited thereto.

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] In the above chemical formulas 2 to 20,

[0122] Z1 to Z3, X1, Ar1, Ar2, dotted line, Cy1 to Cy3, a, b, c, d, e, R1 to R5 are each as defined in the above chemical formula 1.

[0123] In the chemical formula 1 according to the present invention, X1 is O, S, C(Ar4)(Ar5), N(Ar6) and is selected from the group consisting of. These X1-containing ring moieties are a type of dibenzo moieties, and depending on X1, they are dibenzofuran moieties (X1= O), dibenzothiophene moieties (X1= S), fluorene moieties [X1= C(Ar4)(Ar5)], carbazole moieties [X1= N(Ar6)] or phenanthrene moieties (X1= ) may be.

[0124] In the above chemical formula 1, Ar4 to Ar8 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 (e.g., Ar4-Ar5, Ar4-R1, Ar6-R1, Ar7-Ar8, Ar7-R1, etc.) 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 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 or may be selected from the group consisting of arylamine groups, or may be condensed with adjacent groups (e.g., Ar4-Ar5, Ar4-R1, Ar6-R1, Ar7-Ar8, Ar7-R1, etc.) 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.

[0125] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above Ar4 to Ar8 are each independently 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 40Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, 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.

[0126] For example, the X1-containing ring moiety ( The moiety) may be a moiety selected from the group consisting of the following moieties Mo1-1 to Mo1-10, but is not limited thereto.

[0127]

[0128] In the above moieties Mo1-1 to Mo1-10,

[0129] * is a part connected to the above chemical formula 1,

[0130] a is an integer from 0 to 6, specifically an integer from 0 to 2, and more specifically 0 or 1,

[0131] Multiple R1s are identical or different from each other,

[0132] R1 is as defined in the above chemical formula 1.

[0133] In another example, the X1-containing ring moiety may be a moiety selected from the group consisting of, but not limited to, the following moieties Mo2-1 to Mo2-10.

[0134]

[0135] In the above moieties Mo2-1 to Mo2-10,

[0136] * is a part connected to the above chemical formula 1.

[0137] In the chemical formula 1 according to the present invention, a is an integer from 0 to 6, specifically an integer from 0 to 3, and more specifically an integer of 0 or 1, and b is an integer from 0 to 5, specifically an integer from 0 to 3, and more specifically an integer of 0 or 1.

[0138] Here, when a is 0, it means that hydrogen is not substituted with the substituent R1, and when b is 0, it means that hydrogen is not substituted with the substituent R2. On the other hand, when a is an integer from 1 to 6, it means that hydrogen is not substituted with the substituent R1, and when b is an integer from 1 to 5, it means that hydrogen is not substituted with the substituent R2.

[0139] At this time, multiple R1s are identical or different from each other, and multiple R2s are identical or different from each other.

[0140] The above R1 and R2 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), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups (e.g. R1-R1, R2-R2, R1-R2, etc.) to form a condensed ring, and specifically hydrogen, deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C3~C 20 Cycloalkyl group, heterocycloalkyl group having 3 to 20 nuclear atoms, C6~C 30 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0141] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of R1 and R2 are each independently independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each 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 30It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0142] Depending on the bonding relationship of the two moieties centered on the aforementioned L1 and the presence or absence of Cy1 to Cy3 in L1, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 21 to 115. However, the present invention is not limited thereto.

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238] In the above chemical formulas 2 to 115,

[0239] Z1 to Z3, Ar1, Ar2, Cy1 to Cy3, c, d, e, R3 to R5 are each as defined in the above chemical formula 1,

[0240] c1, d1 and e1 are each integers from 0 to 4, specifically, they can each be integers from 0 to 2, and more specifically, they can each be 0 or 1.

[0241] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 252 below, but is not limited thereto.

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] 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.

[0256] 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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0262] 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.

[0263] 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.

[0264] 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.

[0265] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] In the present invention, “arylphosphine oxide group” means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0270] 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.

[0271] 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.

[0272]

[0273] Organic electroluminescent devices

[0274] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0275] 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.

[0276] The organic layer (300) of one or more layers above may include at least one of a hole injection layer (310), a hole transport layer (320), a light emitting layer (330), an electron transport layer (340), and an electron injection layer (350), and optionally may additionally include at least one of an electron transport auxiliary layer (360) and a hole transport auxiliary layer (not shown). At this time, at least one organic layer (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be an electron transport layer (340) or an electron transport auxiliary layer (360).

[0277] According to an example, the organic layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include at least one of an electron transport auxiliary layer and a hole transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound of the above chemical formula 1, and can also move quickly from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0278] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0279] In the present invention, the electron transport layer material that can be mixed with the compound of the above chemical formula 1 may be an electron transport material or n-type dopant commonly known in the art. Non-limiting examples of the electron transport material that can be used in the present invention include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, and aluminum complexes (e.g., Alq). 3,tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more. Examples of n-type dopants usable in the present invention may be metals (e.g., alkali metals or alkaline earth metals) or complexes of the above metals, and specifically, may be LiQ (Lithium Quinolate), etc.

[0280] 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.

[0281] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. In this case, the compound represented by the chemical formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. The compound represented by the chemical formula 1 has a high triplet energy. Therefore, when the compound of the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer increases, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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).

[0286] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the electron transport layer (340)] includes a compound represented by the chemical formula 1.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] 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.

[0291] In addition, the hole injection layer, hole transport layer, light emitting layer, electron injection layer, and hole transport auxiliary layer are not particularly limited, and conventional materials known in the art can be used.

[0292]

[0293] 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.

[0294] [Preparation Example 1] Synthesis of TC-1

[0295]

[0296] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-1 (9.2 g, yield 60%).

[0297] 1H-NMR: δ 8.36(d, 4H), 7.96(d, 2H), 7.71(d, 1H), 7.61~7.60(m, 3H), 7.50(t, 6H), 7.38(t, 2H), 7.25(d, 4H)

[0298] Mass: [(M+H)+] : 497

[0299]

[0300] [Preparation Example 2] Synthesis of TC-2

[0301]

[0302] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-2 (8.9 g, yield 58%).

[0303] 1H-NMR: δ 8.36(d, 4H), 8.10(d, 2H), 7.96~7.94(m, 3H), 7.73(t, 1H), 7.62~7.50(m, 12H)

[0304] Mass: [(M+H)+] : 497

[0305]

[0306] [Preparation Example 3] Synthesis of TC-3

[0307]

[0308] 2-([1,1'-biphenyl]-3-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-3 (8.7 g, yield 59%).

[0309] 1H-NMR: δ 8.38 (d, 1H), 8.36 (d, 2H), 8.10 (d, 2H), 7.96 - 7.94 (m, 4H), 7.75 - 7.73 (m, 4H), 7.62 - 7.60 (m, 7H), 7.50 - 7.41 (m, 6H)

[0310] Mass: [(M+H)+] : 573

[0311]

[0312] [Preparation Example 4] Synthesis of TC-4

[0313]

[0314] 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenylpyrimidine (12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-4 (8.3 g, yield 56%).

[0315] 1H-NMR: δ 8.23(s, 1H), 7.96~7.94(m, 7H), 7,75~7.71(m, 5H), 7.61~7.38(m, 12H), 7.25(2, 2H)~

[0316] Mass: [(M+H)+] : 572

[0317]

[0318] [Preparation Example 5] Synthesis of TC-5

[0319]

[0320] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (2'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-5 (8.9 g, yield 58%).

[0321] 1H-NMR: δ 8.40(d, 1H), 8.36(d, 4H), 7.96~7.94(m, 3H), 7.73(t, 1H), 7.71(d, 1H), 7.61~7.60(m, 4H), 7.50(m, 6H), 7.38(t, 2H)

[0322] Mass: [(M+H)+] : 497

[0323]

[0324] [Preparation Example 6] Synthesis of TC-6

[0325]

[0326] 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (3'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-6 (8.6 g, yield 58%).

[0327] 1H-NMR: δ 8.38 (d, 1H), 8.36 (d, 2H), 7.96 - 7.94 (m, 6H), 7.75 - 7.73 (m, 3H), 7.60 - 7.61 (m, 3H), 7.50 - 7.41 (m, 9H), 7.25 (d, 2H)

[0328] Mass: [(M+H)+] : 573

[0329]

[0330] [Preparation Example 7] Synthesis of TC-7

[0331]

[0332] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 30.9 mmol), (4'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (7.2 g, 30.9 mmol), Pd(PPh3)4 (1.1 g, 0.9 mmol), and K2CO3 (8.5 g, 61.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-7 (9.2 g, yield 60%).

[0333] 1H-NMR: δ 8.38(d, 1H), 8.36(d, 4H), 7.96(d, 2H), 7.94(s, 1H), 7.78~7.73(m, 3H), 7.62~7.60(m, 5H), 7.50(m, 6H)

[0334] Mass: [(M+H)+] : 497

[0335]

[0336] [Preparation Example 8] Synthesis of TC-8

[0337]

[0338] 2-(5-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (2'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (6.0 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-8 (8.2 g, yield 55%).

[0339] 1H-NMR: δ 8.36(d, 4H), 8.04(s, 1H), 7.75~7.71(m, 3H), 7.61(d, 1H), 7.50~7.38(m, 11H), 7.25(d,4H)

[0340] Mass: [(M+H)+] : 573

[0341]

[0342] [Preparation Example 9] Synthesis of TC-9

[0343]

[0344] 2-(2'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (12.0 g, 25.9 mmol), (4-chloronaphthalen-2-yl)boronic acid (5.3 g, 25.9 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain TC-9 (8.1 g, yield 57%).

[0345] 1H-NMR: δ 8.36(d, 4H), 8.32(d, 1H), 8.11(d, 1H), 7.96~7.92(m, 5H), 7.60~7.50(m, 11H), 7.25(d, 2H)

[0346] Mass: [(M+H)+] : 547

[0347]

[0348] [Synthesis Example 1] Synthesis of Compound 1

[0349]

[0350] TC-1 (5.0 g, 10.1 mmol), (9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)boronic acid (3.2 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 1 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (3.2 g, yield 44%).

[0351] Mass: [(M+H)+] : 731

[0352]

[0353] [Synthesis Example 2] Synthesis of Compound 21

[0354]

[0355] TC-2 (5.0 g, 10.1 mmol), (6,9,9-triphenyl-9H-fluoren-2-yl)boronic acid (4.4 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 2 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 21 (4.0 g, yield 46%).

[0356] Mass: [(M+H)+] : 855

[0357]

[0358] [Synthesis Example 3] Synthesis of Compound 30

[0359]

[0360] TC-3 (5.0 g, 8.7 mmol), (9,9-dimethyl-4-phenyl-9H-fluoren-2-yl)boronic acid (2.7 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 3 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 30 (2.9 g, yield 41%).

[0361] Mass: [(M+H)+] : 807

[0362]

[0363] [Synthesis Example 4] Synthesis of Compound 58

[0364]

[0365] TC-4 (5.0 g, 8.7 mmol), (9,9-dimethyl-5-phenyl-9H-fluoren-3-yl)boronic acid (2.7 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 4 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 58 (3.0 g, yield 41%).

[0366] Mass: [(M+H)+] : 806

[0367]

[0368] [Synthesis Example 5] Synthesis of Compound 67

[0369]

[0370] TC-5 (5.0 g, 10.1 mmol), (9,9-dimethyl-8-phenyl-9H-fluoren-2-yl)boronic acid (3.2 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 5 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 67 (3.2 g, yield 44%).

[0371] Mass: [(M+H)+] : 731

[0372]

[0373] [Synthesis Example 6] Synthesis of Compound 81

[0374]

[0375] TC-6 (5.0 g, 8.7 mmol), (9,9-dimethyl-4-phenyl-9H-fluoren-2-yl)boronic acid (2.7 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 6 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 81 (3.4 g, yield 48%).

[0376] Mass: [(M+H)+] : 807

[0377]

[0378] [Synthesis Example 7] Synthesis of Compound 83

[0379]

[0380] TC-7 (5.0 g, 10.1 mmol), (7-phenylphenanthren-2-yl)boronic acid (3.0 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 7 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 83 (3.2 g, yield 45%).

[0381] Mass: [(M+H)+] : 715

[0382]

[0383] [Synthesis Example 8] Synthesis of Compound 85

[0384]

[0385] TC-1 (5.0 g, 10.1 mmol), (7-phenyldibenzo[b,d]furan-4-yl)boronic acid (2.9 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 1 were added to 80 ml of dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 85 (3.3 g, yield 46%).

[0386] Mass: [(M+H)+] : 705

[0387]

[0388] [Synthesis Example 9] Synthesis of Compound 142

[0389]

[0390] TC-4 (5.0 g, 8.7 mmol), (9-phenyldibenzo[b,d]furan-2-yl)boronic acid (2.5 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 4 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 142 (3.2 g, yield 47%).

[0391] Mass: [(M+H)+] : 780

[0392]

[0393] [Synthesis Example 10] Synthesis of Compound 165

[0394]

[0395] TC-6 (5.0 g, 8.7 mmol), (6,9-diphenyl-9H-carbazol-2-yl)boronic acid (3.2 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 6 were added to 80 ml of dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 165 (3.4 g, yield 45%).

[0396] Mass: [(M+H)+] : 856

[0397]

[0398] [Synthesis Example 11] Synthesis of Compound 167

[0399]

[0400] TC-7 (5.0 g, 10.1 mmol), (6-phenyldibenzo[b,d]thiophen-4-yl)boronic acid (3.1 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.6 g, 20.2 mmol) obtained in Preparation Example 7 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 167 (3.1 g, yield 43%).

[0401] Mass: [(M+H)+] : 721

[0402]

[0403] [Synthesis Example 12] Synthesis of Compound 223

[0404]

[0405] TC-8 (5.0 g, 8.7 mmol), (9,9-dimethyl-8-phenyl-9H-fluoren-2-yl)boronic acid (2.7 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) obtained in Preparation Example 8 were added to 80 ml of Dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 223 (3.0 g, yield 43%).

[0406] Mass: [(M+H)+] : 806

[0407]

[0408] [Synthesis Example 13] Synthesis of Compound 250

[0409]

[0410] TC-9 (5.0 g, 9.2 mmol), (4-phenyldibenzo[b,d]furan-2-yl)boronic acid (2.6 g, 9.2 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (6.0 g, 18.3 mmol) obtained in Preparation Example 9 were added to 80 ml of dioxane and 20 ml of H2O, and heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 250 (2.6 g, yield 38%).

[0411] Mass: [(M+H)+] : 755

[0412]

[0413] [Example 1] Fabrication of a blue organic electroluminescent device

[0414] Compound 1 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following process.

[0415] 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.

[0416] 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 + 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 as follows.

[0417]

[0418]

[0419] [Examples 2 to 4] Preparation of blue organic electroluminescent devices

[0420] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the electron transport layer materials in Table 1 were used instead of Compound 1 used as the electron transport layer material in Example 1.

[0421]

[0422] [Comparative Examples 1 to 7] Manufacturing of blue organic electroluminescent devices

[0423] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3 and TP-1 to TP-6 ​​were used instead of Compound 1 used as an electron transport layer material in Example 1. At this time, the structures of Alq3 and TP-1 to TP-6 ​​used are as follows.

[0424]

[0425]

[0426] [Evaluation Example 1]

[0427] For the organic electroluminescent devices manufactured in Examples 1 to 13 and Comparative Examples 1 to 7, 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.

[0428] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 13.44547.0 Example 2 Compound 213.34557.1 Example 3 Compound 303.24537.0 Example 4 Compound 583.44547.1 Example 5 Compound 673.24546.9 Example 6 Compound 813.34536.8 Example 7 Compound 833.44557.0 Example 8 Compound 853.54557.0 Example 9 Compound 1423.34547.1 Example 10 Compound 1653.24547.0 Example 11 Compound 1673.24557.0 Example 12 Compound 2233.34536.9 Example 13 Compound 2503.24547.1 Comparative Example 1 Alq 34.64575.1 Comparative Example 2 TP-14.04586.0 Comparative Example 3 TP-24.14576.1 Comparative Example 4 TP-34.64566.1 Comparative Example 5 TP-44.04576.0 Comparative Example 6 TP-54.14576.0 Comparative Example 7 TP-64.64576.1

[0429] From Table 1 above, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 13 were superior to the organic light-emitting devices manufactured in Comparative Examples 1 to 7 in terms of driving voltage, light emission peak, and current efficiency.

[0430] [Example 14] Fabrication of a blue organic electroluminescent device

[0431] 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.

[0432] 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.

[0433] 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) (30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used are as follows.

[0434]

[0435]

[0436]

[0437] [Examples 15 to 26]

[0438] A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that the electron transport auxiliary layer materials in Table 2 were used instead of compound 1 used as the electron transport auxiliary layer material in Example 14.

[0439]

[0440] [Comparative Example 8]

[0441] A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that compound 1, which was used as an electron transport auxiliary layer material in Example 14, was not used.

[0442]

[0443] [Comparative Examples 9 to 14] Manufacturing of blue organic electroluminescent devices

[0444] A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that TP-1 to TP-6 ​​were used instead of Compound 1, which was used as an electron transport auxiliary layer material in Example 14. The structures of TP-1 to TP-6 ​​used here are as follows, respectively.

[0445]

[0446]

[0447] [Evaluation Example 1]

[0448] For the organic electroluminescent devices manufactured in Examples 14 to 26 and Comparative Examples 8 to 14, 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.

[0449] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 14 Compound 13.14557.4 Example 15 Compound 213.24547.3 Example 16 Compound 303.14547.4 Example 17 Compound 583.14557.5 Example 18 Compound 673.24557.4 Example 19 Compound 813.14547.3 Example 20 Compound 833.24557.4 Example 21 Compound 853.34557.3 Example 22 Compound 1423.34547.3 Example 23 Compound 1653.24557.4 Example 24 Compound 1673.24557.3 Example 25 Compound 2233.24547.3 Example 26 Compound 2503.14547.2 Comparative Example 8-4.64565.6 Comparative Example 9TP-13.84556.0 Comparative Example 10TP-24.14566.1 Comparative Example 11TP-34.54566.1 Comparative Example 12TP-44.04566.1 Comparative Example 13TP-53.94566.1 Comparative Example 14TP-64.54566.0

[0450] From Table 2 above, it was confirmed that the organic light-emitting devices manufactured in Examples 14 to 26 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 8 to 14, respectively.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] (In the above chemical formula 1, Z 1 Inland Z 3 are identical or different from each other, and each independently represents N or C(Ar 3 ) and only Z 1 Inland Z 3 At least two of them are N; Ar 1 and Ar 2 are identical or different from each other, and each is independently C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 6 ~C 60 Arylphosphine group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 is selected from the group consisting of arylamine groups, L 1 is a linker group represented by the following chemical formula L1-1 or L1-2, [Chemical formula L1-1] [Chemical formula L1-2] In the above chemical formulas L1-1 and L1-2, The dotted lines indicate the presence or absence of each ring. Cy 1 Inland Cy 3 are identical or different from each other, each being a six-membered aromatic ring, a, c, d, and e are each integers from 0 to 6, b is an integer from 0 to 5. R 1 Inland R 5 are identical or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 6 ~C 60 Arylphosphine group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, X 1 는 O, S, C(Ar 4 )(The 5 ), N(Ar 6 ) 및 is selected from the group consisting of; Ar 3 Inland Ar 8 are identical or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 6 ~C 60 Arylphosphine group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~C 60 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, Above Ar 1 Inland Ar 8 and R 1 Inland R 5 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 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C 1 ~C 40 Alkyl group of C 2 ~C 40 Alkenyl group of C 2 ~C 40 Alkynyl group of C 3 ~C 40 A cycloalkyl group of , a heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C 1 ~C 40 Alkyloxy group of C 6 ~C 60 Aryloxy group of C 1 ~C 40 Alkylsilyl group of C 6 ~C 60 Arylsilyl group of C 1 ~C 40 Alkylboron group of C 6 ~C 60 Aryl boron group, C 6 ~C 60 Arylphosphine group of C 6 ~C 60 Arylphosphine oxide group and C 6 ~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, L 1 A compound which is a linker group represented by any one of the following chemical formulas L2-1 to L2-5: [Chemical formula L2-1] [Chemical formula L2-2] [Chemical formula L2-3] [Chemical formula L2-4] [Chemical formula L2-5] (In the above chemical formulas L2-1 to L2-5, Dotted line, Cy 1 Inland Cy 3 , c, d, e, R 3 Inland R 4 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 20: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical formula 20] (In the above chemical formulas 2 to 20, Z 1 Inland Z 3 , X 1 , Ar 1 , Ar 2 , dotted line, Cy 1 Inland Cy 3 , a, b, c, d, e, R 1 Inland R 5 are each as defined in Article 1).

4. In paragraph 1, The chemical formula 1 above A compound wherein the moiety is a moiety selected from the group consisting of the following moieties Mo1-1 to Mo1-10: (In the above moieties Mo1-1 to Mo1-10, a and R 1 are each as defined in Article 1) 5. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 21 to 115: [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical formula 29] [Chemical formula 30] [Chemical Formula 31] [Chemical formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical formula 36] [Chemical Formula 37] [Chemical formula 38] [Chemical Formula 39] [Chemical formula 40] [Chemical Formula 41] [Chemical formula 42] [Chemical formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical formula 47] [Chemical formula 48] [Chemical Formula 49] [Chemical formula 50] [Chemical Formula 51] [Chemical formula 52] [Chemical formula 53] [Chemical Formula 54] [Chemical formula 55] [Chemical formula 56] [Chemical formula 57] [Chemical formula 58] [Chemical formula 59] [Chemical formula 60] [Chemical formula 61] [Chemical formula 62] [Chemical formula 63] [Chemical formula 64] [Chemical formula 65] [Chemical formula 66] [Chemical formula 67] [Chemical formula 68] [Chemical formula 69] [Chemical formula 70] [Chemical formula 71] [Chemical formula 72] [Chemical formula 73] [Chemical formula 74] [Chemical formula 75] [Chemical formula 76] [Chemical formula 77] [Chemical formula 78] [Chemical formula 79] [Chemical formula 80] [Chemical formula 81] [Chemical formula 82] [Chemical formula 83] [Chemical formula 84] [Chemical formula 85] [Chemical formula 86] [Chemical formula 87] [Chemical formula 88] [Chemical formula 89] [Chemical formula 90] [Chemical formula 91] [Chemical formula 92] [Chemical formula 93] [Chemical formula 94] [Chemical formula 95] [Chemical formula 96] [Chemical formula 97] [Chemical formula 98] [Chemical formula 99] [Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 102] [Chemical Formula 103] [Chemical Formula 104] [Chemical Formula 105] [Chemical formula 106] [Chemical Formula 107] [Chemical Formula 108] [Chemical Formula 109] [Chemical formula 110] [Chemical formula 111] [Chemical formula 112] [Chemical formula 113] [Chemical Formula 114] [Chemical formula 115] (In chemical formulas 2 to 115, Z 1 Inland Z 3 , Ar 1 , Ar 2 , Cy 1 Inland Cy 3 , c, d, e, R 3 Inland R 5 are as defined in Article 1, respectively, c1, d1, and e1 are integers from 0 to 4, respectively).

6. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 252 below: .

7. Anode; cathode; comprising at least one organic layer interposed between the anode and the cathode, An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises a compound according to any one of claims 1 to 6.

8. In paragraph 7, An organic electroluminescent device, wherein the organic layer containing the above compound is an electron transport layer or an electron transport auxiliary layer.

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