Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to a novel compound and an organic electroluminescent device using same and, more specifically, to: an organic compound having excellent electron transport ability, heat resistance, carrier transport ability, luminescence performance, and the like; and an organic electroluminescent device including the organic compound in at least one organic layer and thus having improved characteristics in terms of luminous efficiency, driving voltage, lifespan, and the like.

Description

Organic compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic compound having excellent electron transport capability 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 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, 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] X1 is selected from the group consisting of O, S and N(R6),

[0013] Z1 to Z3 are the same or different from each other, and are each independently N or C(R7), provided that at least two of Z1 to Z3 are N,

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

[0015] L1 is a single bond, or C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms,

[0016] Ar1 and Ar2 are the same or different, and each independently represents 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 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

[0017] a, b, c and e are each integers from 0 to 4,

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

[0019] R1 to R7 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 60Aryl 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 a group to form a condensed ring,

[0020] The arylene group and heteroarylene group of the above L1, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group and heteroaryl group of the above Ar1 and Ar2, 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 R7 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 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0021] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the aforementioned chemical formula 1.

[0022] In one example, the organic layer containing the compound may be an electron transport layer or an electron transport auxiliary layer.

[0023] 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.

[0024] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0025] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0026] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0027] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0028] <Explanation of symbols>

[0029] 100: anode, 200: cathode,

[0030] 300: Organic layer, 310: Hole injection layer,

[0031] 320: hole transport layer, 330: light emitting layer,

[0032] 340: electron transport layer, 350: electron injection layer,

[0033] 360: Electron transport auxiliary layer

[0034] Hereinafter, the present invention will be described.

[0035] <New organic compounds>

[0036] The present invention provides a novel organic compound that can be used as a high-efficiency organic layer material, particularly an electron transport layer material and an electron transport auxiliary layer material, due to its excellent electron injection and transport ability, electrochemical stability, thermal stability, carrier transport ability, and luminescence ability.

[0037] Specifically, the organic compound according to the present invention has a structure in which a heteroaromatic ring moiety containing 2 to 3 nitrogen (N) atoms is directly bonded to a spiro moiety or bonded via a linker group (e.g., a phenylene group, a biphenylene group, a naphthalene group, etc.), and is represented by the chemical formula 1.

[0038] In conventional organic devices, especially those using a blue fluorescent emitting layer, the maximum amount of excitons must be generated in a narrow region to increase the efficiency of the device. However, in phosphorescent devices, even if excitons are densely packed, device efficiency may decrease due to reasons such as triplet-triplet annihilation (TTA). On the other hand, in fluorescent devices, since the TTA phenomenon contributes to the generation of excitons in the S1 state, the electron transport layer must have fast electron transport and injection capabilities in order to utilize the T1 energy in the emitting layer. Therefore, in the present invention, by containing a spiro moiety such as a highly conductive spiro[annulene-xanthene] moiety, a spiro[annulene-thioxanthene] moiety, or a spiro[annulene-acridine] moiety, the electron transport and injection capabilities of the compound can be enhanced. In addition, the compound of the present invention can improve the lifespan of a device by inducing the formation of an appropriate light-emitting region within a light-emitting layer by controlling electron transport ability by increasing the bulkiness of the molecule due to the structure of the spiro moiety.

[0039] In the compound represented by the above chemical formula 1, the heteroaromatic ring moiety contains 2 to 3 nitrogens (N) and is an electron withdrawing group (EWG) with excellent electron transport ability. By bonding this heteroaromatic ring moiety to a highly conductive spiro moiety, high electron mobility can be induced, and thus the compound of the present invention can have physicochemical properties more suitable for electron injection and electron transport.

[0040] In addition, since the compound represented by the chemical formula 1 of the present invention has a higher triplet energy than the light-emitting layer, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, the number of excitons contributing to light emission increases, so that the light-emitting efficiency of the device can be improved, and the durability and electrochemical stability of the device can be improved, so that the lifespan of the device can be efficiently increased. In addition, the organic electroluminescent device to which the compound represented by the chemical formula 1 of the present invention is applied can realize low-voltage operation.

[0041] 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 heteroaromatic ring moiety, thereby increasing its glass transition temperature and improving its thermal safety and electrochemical stability.

[0042] As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron transport ability, thermal stability, electrochemical stability, etc., and thus can be 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 improving 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.

[0043]

[0044] The organic compound represented by the above chemical formula 1 is a compound in which a Z1 to Z3-containing ring moiety is directly bonded to a spiro moiety [e.g., a spiro[annulene-xanthene] moiety, etc.] or through a linker group, as described above, and may be a compound represented by any one of the following chemical formulas 2 to 4 depending on the position at which the Z1 to Z3-containing ring moiety is bonded (introduced), but is not limited thereto.

[0045] [Chemical Formula 2]

[0046]

[0047] [Chemical Formula 3]

[0048]

[0049] [Chemical Formula 4]

[0050]

[0051] In the above chemical formulas 2 to 4,

[0052] X1, Z1 to Z3, n, L1, Ar1, Ar2, a, b, c, d, e and R1 to R5 are each as defined in the above chemical formula 1.

[0053] In the above chemical formula 1, X1 is selected from the group consisting of O, S, and N(R6). Depending on X1, the spiro moiety can be a spiro[annulene-xanthene] moiety, a spiro[annulene-thioxanthene] moiety, or a spiro[annulene-acridine] moiety.

[0054] In the above chemical formula 1, Z1 to Z3 are the same or different, and are each independently N or C(R7), provided that at least two of Z1 to Z3 are N. The Z1 to Z3-containing ring moiety is a type of nitrogen (N)-containing heteroaromatic ring, and is a 6-membered heteroaryl group (e.g., pyrimidine, triazine group) containing at least two nitrogen atoms. Such a 6-membered heteroaryl group (e.g., pyrimidine group, triazine group, etc.) containing at least two nitrogen atoms has better electron withdrawing properties than a pyridine group, and thus lowers the LUMO energy, thereby increasing the electron transport and injection capabilities of the compound. Therefore, the compound of chemical formula 1 according to the present invention containing a heteroaromatic ring containing at least two nitrogen atoms may exhibit better electron absorption properties, and thus be advantageous for electron injection and transport.

[0055] 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.

[0056]

[0057] In the above moieties Az-1 to Az-3,

[0058] * is a part connected to the above chemical formula 1,

[0059] Ar1, Ar2 and R7 are each as defined in the above chemical formula 1.

[0060] 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.

[0061] In the above chemical formula 1, 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 C6~C60 Selected from the group consisting of arylene group and heteroarylene group having 5 to 60 nuclear atoms, specifically C6~C 30 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0062] At this time, the arylene group and heteroarylene group of the above L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~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.

[0063] For example, L1 is a single bond, or C6~C 18 It can be an arylene group of L1, and the arylene group of L1 is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), 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 Aryl group of C1~C 20 Alkylphosphine oxide group, C6~C 30 Arylphosphine oxide group, C6~C 30 It may be 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. Here, multiple L1s may be the same or different from each other.

[0064] According to another example, 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 selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 10 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0065] In another example, the L1 may be a single bond or selected from the group consisting of linker groups L1-1 to L1-8 below. However, the present invention is not limited thereto. Here, multiple L1s may be the same or different from each other.

[0066]

[0067] In the above linker groups L1-1 to L1-8,

[0068] f is an integer from 0 to 4, specifically 0 or 1,

[0069] g is an integer from 0 to 6, specifically 0 or 1,

[0070] Multiple R's are the same or different from each other,

[0071] 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 60Selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, 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.

[0072] For example, R may be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group, carbazole group, and fluorene group.

[0073] In the above chemical formula 1, Ar1 and Ar2 are the same or different from each other, and each independently represents 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, and heteroaryl group having 5 to 60 nuclear atoms, and specifically, each of which is selected from the group consisting of deuterium (D), C1~C 20 Alkyl group of C6~C 30 It can be selected from the group consisting of an aryl group of C6~C and a heteroaryl group having 5 to 30 nuclear atoms, and more specifically, 18 It can be an aryl group.

[0074] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group and heteroaryl group of 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), 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 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.

[0075] In one embodiment, 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.

[0076] 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 S1-11, but are not limited thereto.

[0077]

[0078] In the above substituents S1-1 to S1-11,

[0079] X2 is O, S, C(R8)(R9), Si(R 10 )(R 11 ) and N(R 12 ) is selected from the group consisting of,

[0080] R8 to R 12 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~C40 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~C 30 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,

[0081] h is an integer from 0 to 5,

[0082] i is an integer from 0 to 4,

[0083] j is an integer from 0 to 7,

[0084] k is an integer from 0 to 6,

[0085] i is an integer from 0 to 9,

[0086] m is an integer from 0 to 8,

[0087] o is an integer from 0 to 3,

[0088] Multiple R's are the same or different from each other,

[0089] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, 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 60Condensed 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.

[0090] 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 S41, but are not limited thereto.

[0091]

[0092]

[0093] In the above substituents S1 to S41,

[0094] * means a negative element that is combined with the above chemical formula 1,

[0095] h1 is an integer from 1 to 5, specifically an integer from 1 to 3,

[0096] j1 is an integer from 1 to 7, specifically an integer from 1 to 4, and more specifically 1 or 2,

[0097] Me is a methyl group,

[0098] Et is ethyl group,

[0099] Pr is an n-propyl group or an iso-propyl group,

[0100] Bu is an n-butyl group, an iso-butyl group, or a tert-butyl group.

[0101] In addition, the hydrogen of the above substituents S1 to S41 is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups and heteroaryl groups having 5 to 10 nuclear atoms.

[0102] In the above chemical formula 1, a, b, c, and e are each integers from 0 to 4, and d is an integer from 0 to 3.

[0103] Here, when a is 0, it means that hydrogen is not substituted with the substituent R1, when b is 0, it means that hydrogen is not substituted with the substituent R2, 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 R5. On the other hand, when a is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R1, when b is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R2, when c is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R3, when d is an integer from 1 to 3, it means that hydrogen is substituted with the substituent R4, and when e is an integer from 1 to 4, it means that hydrogen is substituted with the substituent R5.

[0104] 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.

[0105] The above R1 to R7 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 60 A group selected from the group consisting of arylamine groups, or a group collected (e.g., R1-R1, R2-R2, R3-R3, R4-R4, R5-R5, R1-R2, R2-R3, R3-R4, R4-L1, R5-R1, etc.) is condensed 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 An aryl group of C3~C, and a heteroaryl group having 5 to 30 nuclear atoms may be selected from the group consisting of, or may be condensed with a group 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 30fused 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.

[0106] 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 to R7 are each independently each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0107] Depending on the type of L1 mentioned above, the type of Z1 to Z3-containing ring moiety, and the bonding position, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 5 to 10. However, the present invention is not limited thereto.

[0108] [Chemical Formula 5]

[0109]

[0110] [Chemical Formula 6]

[0111]

[0112] [Chemical Formula 7]

[0113]

[0114] [Chemical Formula 8]

[0115]

[0116] [Chemical Formula 9]

[0117]

[0118] [Chemical Formula 10]

[0119]

[0120] In the above chemical formulas 5 to 10,

[0121] X1, n, Ar1, Ar2, a, b, c, d, e, R1 to R5 and R7 are each as defined in the above chemical formula 1,

[0122] f is an integer from 0 to 4, specifically 0 or 1,

[0123] g is an integer from 0 to 6, specifically 0 or 1,

[0124] Multiple R's are the same or different from each other,

[0125] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, 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 30fused 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.

[0126] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 152 below, but is not limited thereto.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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 dibenzofuranyl, dibenzothiophenyl, 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153]

[0154] Organic electroluminescent devices

[0155] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0156] 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.

[0157] 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).

[0158] 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.

[0159] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0160] 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., Alq3). ,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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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).

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] 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.

[0173]

[0174] 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.

[0175] [Preparation Example 1] - Synthesis of Core 1

[0176] <Step 1-1>

[0177]

[0178] 80.0 g (282.1 mmol) of 1-bromo-2-(4-chlorophenoxy)benzene was dissolved in 800 mL of THF, and the internal temperature was cooled to -78 °C using a dry ice acetone bath. Then, 118.5 mL (296.2 mmol) of n-BuLi (1.6 M in hexane) was slowly added dropwise. After reacting at -78 °C for 2 hours, 72.3 g (282.1 mmol) of 9H-tribenzo[a,c,e][7]annulen-9-one was dissolved in 700 mL of THF in another reactor, and then cooled to -78 °C. Afterwards, the reaction solution containing 1-bromo-2-(4-chlorophenoxy)benzene was slowly added dropwise to the reactor containing 9H-tribenzo[a,c,e][7]annulen-9-one using a cannula. Then, the temperature inside the reactor was raised to room temperature and the reaction was carried out for 4 hours. After the reaction was completed, the organic layer was extracted using H2O and ethyl acetate, anhydrous treatment was made with MgSO4, and then filtered. The filtered organic layer was concentrated under reduced pressure and purified by column chromatography to obtain 123.8 g (yield 95.2%) of 9-(2-(4-chlorophenoxy)phenyl)-9H-tribenzo[a,c,e][7]annulen-9-ol.

[0179] <Step 1-2>

[0180]

[0181] Above<Step 1-1> 123.8 g (268.6 mmol) of 9-(2-(4-chlorophenoxy)phenyl)-9H-tribenzo[a,c,e][7]annulen-9-ol, 800 mL of AcOH, and 200 mL of 6N HCl were placed in a reactor and reacted under reflux for 4 hours. After completion of the reaction, the produced solid was filtered and washed with water. The filtered solid was dissolved in MC, anhydrous treated with MgSO4, and filtered again. The filtered organic layer was recrystallized using MC and MeOH, and the solid was filtered and washed with MeOH. The obtained solid was placed in a drying oven and dried for one day to obtain 111.6 g (yield 93.8%) of 2'-chlorospiro[tribenzo[a,c,e][7]annulene-9,9'-xanthene.

[0182] <Step 1-3>

[0183]

[0184] Above<Step 1-2> 2'-chlorospiro[tribenzo[a,c,e][7]annulene-9,9'-xanthene] 111.6 g (262.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 80.0 g (315.1 mmol), obtained from Pd(dppf)Cl2 5.8 g (7.9 mmol), XPhos 12.5 g (26.3 mmol), KOAc 77.3 g (787.8 mmol) and 1,4-Dioxane 1200 ml were added and reacted by refluxing at 110 ℃ for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the organic layer was extracted using H2O and MC. The extracted organic layer was made anhydrous with MgSO4 and filtered. The filtered organic layer was concentrated under reduced pressure and purified by column chromatography to obtain 105.1 g (yield 74.9%) of the target compound, Core 1.

[0185] Mass: [(M+H) + ] : 535

[0186]

[0187] [Preparation Example 2] - Synthesis of Core 2

[0188] <Step 2-1>

[0189]

[0190] Preparation Example 1<Step 1-1> Preparation Example 1 was prepared as described above, except that 80.0 g (259.3 mmol) of 4-(2-bromo-4-chlorophenoxy)benzonitrile was used instead of 1-bromo-2-(4-chlorophenoxy)benzene used in<Step 1-1> The target compound was obtained by performing the same procedure.

[0191] <Step 2-2>

[0192]

[0193] Preparation Example 1<Step 1-2> Instead of 9-(2-(4-chlorophenoxy)phenyl)-9H-tribenzo[a,c,e][7]annulen-9-ol used in<Step 2-1> Except for using the target compound obtained from Preparation Example 1,<Step 1-2> The target compound was obtained by performing the same procedure.

[0194] <Step 2-3>

[0195]

[0196] Preparation Example 1<Step 1-3> Instead of 2'-chlorospiro[tribenzo[a,c,e][7]annulene-9,9'-xanthene] used in<Step 2-2> Except for using the target compound obtained from Preparation Example 1,<Step 1-3> The same procedure was performed to obtain 51.1 g of the target compound, Core 2 (three-step yield: 35.2%).

[0197] Mass: [(M+H) + ] : 560

[0198]

[0199] [Synthesis Example 1] Synthesis of Compound 4

[0200]

[0201]

[0202] 8.0 g (1eq, 19.1 mmol) of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, 10.7 g (1.05eq, 20.0 mmol) of Core 1 of [Preparation Example 1], 20.1 g (0.03eq, 0.6 mmol) of Pd(OAc), 18.6 g (3.0eq, 57.2 mmol) of Cs2CO3, and 0.5 g (0.06eq, 1.1 mmol) of Xphos were added to 100 mL of toluene, 25 mL of EtOH, and 25 mL of H2O, and reacted by heating and refluxing for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene and acetone to obtain 11.4 g (yield 75.8%) of compound 4.

[0203] Mass: [(M+H) + ] : 793

[0204]

[0205] [Synthesis Example 2] Synthesis of Compound 6

[0206]

[0207] Except for using 9.0 g (1 eq, 21.4 mmol) of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as [Synthesis Example 1] was performed to obtain 10.9 g (yield 71.3%) of compound 6.

[0208] Mass: [(M+H) + ] : 717

[0209]

[0210] [Synthesis Example 3] Synthesis of Compound 12

[0211]

[0212] 8.0 g (1 eq, 23.3 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine, 13.1 g (1.05 eq, 24.4 mmol) of Core 1 of [Preparation Example 1], 1.3 g (0.05 eq, 1.2 mmol) of Pd(PPh3), and 9.7 g (3.0 eq, 69.8 mmol) of K2CO3 were added to 100 mL of toluene, 25 mL of EtOH, and 25 mL of H2O, and the mixture was heated under reflux for 4 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the residue was purified by column chromatography using dichloromethane and hexane, and then recrystallized with toluene to obtain 14.5 g (yield 87.2%) of compound 12.

[0213] Mass: [(M+H) + ] : 717

[0214]

[0215] [Synthesis Example 4] Synthesis of Compound 13

[0216]

[0217] Except for using 8.0 g (20.3 mmol) of 2-(2-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 9.0 g (yield 57.9%) of compound 13.

[0218] Mass: [(M+H) + ] : 767

[0219]

[0220] [Synthesis Example 5] Synthesis of Compound 18

[0221]

[0222] Except that 5.0 g (11.9 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 6.0 g (yield 63.3%) of compound 18.

[0223] Mass: [(M+H) + ] : 793

[0224]

[0225] [Synthesis Example 6] Synthesis of Compound 20

[0226]

[0227] Except for using 7.0 g (23.8 mmol) of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same process as [Synthesis Example 1] was performed to obtain 13.1 g (yield 89.8%) of compound 20.

[0228] Mass: [(M+H) + ] : 717

[0229]

[0230] [Synthesis Example 7] Synthesis of Compound 50

[0231]

[0232] Except for using 8.0 g (19.1 mmol) of 4-(3'-chloro-[1,1'-biphenyl]-4-yl)-2,6-diphenylpyrimidine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 12.4 g (81.9% yield) of compound 50.

[0233] Mass: [(M+H) + ] : 792

[0234]

[0235] [Synthesis Example 8] Synthesis of Compound 51

[0236]

[0237] Except for using 8.0 g (19.1 mmol) of 4-(3'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 11.5 g (yield 76.2%) of compound 51.

[0238] Mass: [(M+H) + ] : 792

[0239]

[0240] [Synthesis Example 9] Synthesis of Compound 54

[0241]

[0242] Except for using 8.0 g (19.1 mmol) of 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-2,6-diphenylpyrimidine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same process as [Synthesis Example 1] was performed to obtain 13.6 g (89.9% yield) of compound 54.

[0243] Mass: [(M+H) + ] : 792

[0244]

[0245] [Synthesis Example 10] Synthesis of Compound 57

[0246]

[0247] Except that 8.0 g (19.1 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 13.2 g (87.7% yield) of compound 57.

[0248] Mass: [(M+H) + ] : 792

[0249]

[0250] [Synthesis Example 11] Synthesis of Compound 58

[0251]

[0252] Except that 8.0 g (19.1 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 14.1 g (yield 93.1%) of compound 58.

[0253] Mass: [(M+H) + ] : 792

[0254]

[0255] [Synthesis Example 12] Synthesis of Compound 60

[0256]

[0257] Except that 8.0 g (16.2 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(2'-chloro-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 9.2 g (yield 65.3%) of compound 60.

[0258] Mass: [(M+H) + ] : 868

[0259]

[0260] [Synthesis Example 13] Synthesis of Compound 61

[0261]

[0262] Except that 8.0 g (16.2 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 10.0 g (yield 71.6%) of compound 61.

[0263] Mass: [(M+H) + ] : 868

[0264]

[0265] [Synthesis Example 14] Synthesis of Compound 76

[0266]

[0267] Except that 8.0 g (16.2 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-(3'-chloro-[1,1'-biphenyl]-4-yl)-6-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 9.7 g (yield 69.5%) of compound 76.

[0268] Mass: [(M+H) + ] : 868

[0269]

[0270] [Synthesis Example 15] Synthesis of Compound 81

[0271]

[0272] Except that 8.0 g (16.2 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 8.1 g (yield 57.9%) of compound 81.

[0273] Mass: [(M+H) + ] : 868

[0274]

[0275] [Synthesis Example 16] Synthesis of Compound 87

[0276]

[0277] Except for using 8.0 g (20.4 mmol) of 4-(2-chlorophenyl)-6-(naphthalen-2-yl)-2-phenylpyrimidine instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as in [Synthesis Example 1] was performed to obtain 11.9 g (yield 76.8%) of compound 87.

[0278] Mass: [(M+H) + ] : 766

[0279]

[0280] [Synthesis Example 17] Synthesis of Compound 97

[0281]

[0282] Compound 97 (10.5 g, 65.2% yield) was obtained by performing the same procedure as in [Synthetic Example 3], except that 8.0 g (21.7 mmol) of 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile was used.

[0283] Mass: [(M+H) + ] : 742

[0284]

[0285] [Synthesis Example 18] Synthesis of Compound 98

[0286]

[0287] Except for using 8.0 g (21.7 mmol) of 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], the same procedure as [Synthesis Example 3] was performed to obtain 8.5 g (yield 52.8%) of compound 98.

[0288] Mass: [(M+H) + ] : 742

[0289]

[0290] [Synthesis Example 19] Synthesis of Compound 101

[0291]

[0292] Except that 10.0 g (29.1 mmol) of 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine used in [Synthesis Example 1], and 17.1 g (30.54 mmol) of Core 2 of [Preparation Example 2] was used instead of Core 1, the same procedure as in [Synthesis Example 1] was performed to obtain 14.5 g (yield 67.1%) of compound 101.

[0293] Mass: [(M+H) + ] : 742

[0294]

[0295] [Synthesis Example 20] Synthesis of Compound 103

[0296]

[0297] [Synthesis Example 1] was performed in the same manner as in [Synthesis Example 1], except that 10.0 g (29.1 mmol) of 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and 17.1 g (30.54 mmol) of Core 2 was used instead of Core 1, thereby obtaining 14.3 g (yield 66.3%) of compound 103.

[0298] Mass: [(M+H) + ] : 742

[0299]

[0300] [Example 1] Fabrication of a blue fluorescent organic electroluminescent device

[0301] After high-purity sublimation purification of compound 97 using a commonly known method, a blue organic electroluminescent device was manufactured as follows.

[0302] 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.

[0303] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HT-1 + 2 wt% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / 98 wt% BH + 2 wt% BD (200 Å) / ET-2 (50 Å) / compound 97:LiQ = 1:1 weight ratio (300 Å) / LiF (10 Å) / Al (1000 Å) in that order. At this time, the structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2 and LiQ used are as follows.

[0304]

[0305]

[0306]

[0307]

[0308] [Examples 2 to 4] - Fabrication of blue organic electroluminescent devices

[0309] 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 97 used as the electron transport layer material in Example 1.

[0310]

[0311] [Comparative Example 1] Fabrication of a Blue Fluorescent Organic Electroluminescent Device

[0312] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound ET-1 was used instead of the compound 97 used as the electron transport layer material in Example 1. The structure of the compound ET-1 used here is as follows.

[0313]

[0314]

[0315] [Evaluation Example 1]

[0316] For each blue organic electroluminescent device manufactured in Examples 1 to 4 and Comparative Example 1, the driving voltage, current efficiency, and luminescence peak at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0317] Sample Electron Transport Layer Material Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 1 Compound 974.5 460 6.4 Example 2 Compound 984.6 461 6.3 Example 3 Compound 1014.3 460 6.5 Example 4 Compound 1034.2 460 6.3 Comparative Example 1 ET-14.7 45 95.9

[0318] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 4 using the compound according to the present invention as an electron transport layer material exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 1 using the conventional compound ET-1 in the electron transport layer.

[0319] [Example 5] Fabrication of a blue fluorescent organic electroluminescent device

[0320] After high-purity sublimation purification of compound 4 using a commonly known method, a blue organic electroluminescent device was manufactured as follows.

[0321] A glass substrate coated with a 1500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, 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.

[0322] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HT-1 + 2 wt% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / 98 wt% BH + 2 wt% BD (200 Å) / Compound 4 (50 Å) / ET-1: LiQ = 1:1 weight ratio (300 Å) / LiF (10 Å) / Al (1000 Å) in that order. At this time, the structures of HT-1, HAT-CN, HT-2, BH, BD and LiQ used are the same as those described in Example 1, and ET-1 is the same as those described in Comparative Example 1, and therefore, the description thereof is omitted.

[0323]

[0324] [Examples 5 to 20] - Fabrication of blue organic electroluminescent devices

[0325] A blue organic electroluminescent device was manufactured in the same manner as in Example 5, except that each of the compounds described in Table 2 below was used instead of Compound 4 used as an electron transport auxiliary layer material in Example 5.

[0326]

[0327] [Comparative Examples 2 to 5] Fabrication of Blue Fluorescent Organic Electroluminescent Devices

[0328] A blue organic electroluminescent device was manufactured in the same manner as in Example 5, except that compounds ET-2 to ET-5 were used instead of compound 4 used as an electron transport auxiliary layer material in Example 5. The structures of ET-2, ET-3, ET-4, and ET-5 used here are as follows, respectively.

[0329]

[0330]

[0331] [Evaluation Example 2]

[0332] For the organic electroluminescent devices manufactured in Examples 6 to 20 and Comparative Examples 2 to 5, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0333] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 5 Compound 44.34616.4 Example 6 Compound 64.44606.7 Example 7 Compound 124.74625.9 Example 8 Compound 134.44606.1 Example 9 Compound 184.64586.3 Example 10 Compound 204.24596.7 Example 11 Compound 504.64606.7 Example 12 Compound 514.24605.9 Example 13 Compound 544.54626.2 Example 14 Compound 574.44626.4 Example 15 Compound 584.54616.2 Example 16 Compound 604.54596.3 Example 17 Compound 614.64606.6 Example 18 Compound 764.44596.7 Example 29 Compound 814.34616.2 Example 20 Compound 874.44606.5 Comparative Example 2 ET-24.74615.8 Comparative Example 3 ET-34.84604.9 Comparative Example 4 ET-44.84625.7 Comparative Example 5 ET-55.24605.8

[0334] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 5 to 20 including the compound according to the present invention as an electron transport auxiliary layer material exhibited superior performance in terms of current efficiency and driving voltage compared to the organic electroluminescent devices of Comparative Examples 2 to 5 each using compounds ET-2 to ET-5 as conventional electron transport auxiliary layer materials.

Claims

1. An organic compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, X 1 Silver O, S and N(R 6 ) is selected from the group consisting of, Z 1 Inland Z 3 are identical or different from each other, and each independently represents N or C(R 7 ) and only Z 1 Inland Z 3 At least two of them are N, n is an integer from 0 to 3, L 1 is a single bond, or C 6 ~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, Ar 1 and Ar 2 are identical or different from each other, and each independently represents deuterium (D), 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 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, a, b, c and e are each integers from 0 to 4, d is an integer from 0 to 3, R 1 Inland R 7 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 a group to form a condensed ring, Above L 1 Arylene group and heteroarylene group of Ar 1 and Ar 2 An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group and a heteroaryl group, and the R 1 Inland R 7 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 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, The organic compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 2 to 4: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] (In the above chemical formulas 2 to 4, X 1 , Z 1 Inland Z 3 , n, L 1 , Ar 1 , Ar 2 , a, b, c, d, e and R 1 Inland R 5 are each as defined in Article 1).

3. In paragraph 1, Above L 1 An organic compound, wherein the organic compound is a single bond or is selected from the group consisting of the following linker groups L1-1 to L1-8: (In the above linker groups L1-1 to L1-8, f is an integer from 0 to 4, g 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, 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).

4. In paragraph 1, Above Ar 1 and Ar 2 An organic compound, wherein each of the following substituents S1-1 to S1-11 is identical or different and is independently selected from the group consisting of: (In the above substituents S1-1 to S1-11, X 2 is O, S, C(R 8 )(R 9 ), Si(R 10 )(R 11 ) and N(R 12 ) is selected from the group consisting of, R 8 Inland R 12 are identical or different from each other, and each independently represents 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 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, h is an integer from 0 to 5, i is an integer from 0 to 4, j is an integer from 0 to 7, k is an integer from 0 to 6, i is an integer from 0 to 9, m is an integer from 0 to 8, o is an integer from 0 to 3, Multiple R's are identical or different from each other, R is 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 (selected from the group consisting of arylamine groups).

5. In paragraph 1, The compound represented by the above chemical formula 1 is an organic compound represented by any one of the following chemical formulas 5 to 10: [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] (In the chemical formulas 5 to 10 above, X 1 , n, Ar 1 , Ar 2 , a, b, c, d, e, R 1 Inland R 5 and R 7 are as defined in Article 1, respectively, f is an integer from 0 to 4, g is an integer from 0 to 6, Multiple R's are identical or different from each other, R is 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 (selected from the group consisting of arylamine groups).

6. In paragraph 1, The compound represented by the above chemical formula 1 is an organic compound selected from the group consisting of compounds 1 to 152 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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