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 exhibiting excellent electron injection and transport ability and thermal stability and an organic electroluminescent device comprising same in one or more organic material layers thereof, thereby exhibiting improved properties such as luminous efficiency, driving voltage, lifespan, etc.

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 containing the same, and more specifically, to an organic compound having excellent characteristics such as electron injection and transport capacity, luminescence capacity, electrical stability, and thermal stability, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002] In an organic electroluminescent 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 light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0003] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0004] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

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

[0006] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0007] The present invention aims to provide a novel organic compound that can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, a lifespan improvement layer material, a light-emitting auxiliary layer material, an electron transport layer material or an electron transport auxiliary layer material, more specifically as an electron transport layer material or an electron transport auxiliary layer material, due to its excellent heat resistance, carrier transport capacity, electron injection and transport capacity, and light emission capacity.

[0008] In addition, the present invention aims to provide an organic electroluminescent device comprising the aforementioned organic compound that has a low driving voltage, high luminous efficiency, and an improved lifespan.

[0009] To achieve the above-mentioned objectives, 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 identical or different from each other, and each is independently N or C(R1), provided that at least two of Z1 to Z3 are N,

[0013] A is a substituent represented by the following chemical formula A1-1 or A1-2, and

[0014] [Chemical Formula A1-1]

[0015]

[0016] [Chemical Formula A1-2]

[0017]

[0018] In the above chemical formulas A1-1 and A1-2,

[0019] a is an integer from 0 to 3, and

[0020] b, c, and e are each integers from 0 to 5, and

[0021] d is an integer from 0 to 4, and

[0022] x, y, and z are integers from 0 to 3, respectively, and

[0023] R1 to R6 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40 alkylphosphine group of, C6~C 60arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0024] n is an integer from 0 to 4, and

[0025] Multiple L1s are identical or different from each other, and

[0026] L1 is a single bond, or C1~C 40 alkylene group of, C3~C 40 cycloalkylene group of, C6~C 30 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclei,

[0027] m is an integer from 1 to 9, and

[0028] Ar1 and Ar2 are identical or different from each other, and each independently contains deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40 alkylphosphine group of, C6~C 60 arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60Selected from the group consisting of arylamine groups,

[0029] The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, phosphine groups, alkylphosphine groups, arylphosphine groups, phosphine oxide groups, alkylphosphine oxide groups, arylphosphine oxide groups, and arylamine groups of R1 to R6 and Ar1 and Ar2, and the alkylene groups, cycloalkylene groups, arylene groups, and heteroarylene groups of L1 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other).

[0030] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0031] For example, the organic layer containing the above organic compound may be an electron transport layer, an electron transport auxiliary layer, or both.

[0032] The compound of the present invention can be used as an organic layer material for an organic electroluminescent device because it exhibits excellent electron transport and injection capabilities, heat resistance, luminescence, and electrochemical stability. In particular, when the compound of the present invention is used as at least one of an electron transport layer material and an electron transport auxiliary layer material, an organic electroluminescent device having superior luminescence performance, low driving voltage, high efficiency, fast mobility, and long lifespan characteristics compared to conventional materials can be manufactured, and furthermore, a full-color display panel with improved performance and lifespan can also be manufactured.

[0033] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0034] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0035] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0036] FIG. 3 is a schematic cross-sectional view of an organic electroluminescent device according to a third embodiment of the present invention.

[0037] <Explanation of Symbols>

[0038] 100: Anode, 200: Cathode,

[0039] 300: Organic layer, 310: Hole injection layer,

[0040] 320: Hole transport layer, 330: Emitting layer,

[0041] 340: Electron transport layer, 350: Electron injection layer,

[0042] 360: Electron transport auxiliary layer

[0043] The present invention will be described below.

[0044] <New Organic Compounds>

[0045] The organic compound according to the present invention comprises a phenanthrene moiety substituted with at least one substituent (e.g., phenyl group, naphthyl group, etc.); a six-membered nitrogen-containing heteroaromatic ring moiety bonded directly or via a linker group to one side of the phenanthrene moiety; and three or more phenyl group-containing moietys bonded to the other side of the nitrogen-containing heteroaromatic ring moiety, wherein the phenyl group-containing moiety comprises at least one ortho-bond, and is represented by Chemical Formula 1. Such a compound has excellent heat resistance, carrier transport capacity (particularly electron injection and transport capacity), luminescence capacity, electrochemical stability, etc., and can realize characteristics of an organic electroluminescent device, such as high efficiency, long lifespan, and low driving voltage characteristics of the device.

[0046] In the organic compound according to the present invention, a phenanthrene moiety and a nitrogen-containing heteroaromatic ring moiety are bonded to both sides of the molecule directly or through a linker group. In this case, the phenanthrene moiety is an electron-donating group (EDG) with high electron-donating properties, and the nitrogen-containing heteroaromatic ring moiety is an electron-withdrawing group (EWG) with high electron-absorbing properties.

[0047] The compounds of the present invention exhibit excellent thermal stability as well as excellent structural stability due to the phenanthrene moiety. These phenanthrene moietys are substituted with substituents (Ar2) such as phenyl groups, biphenyl groups, and naphthyl groups. As a result, the steric hindrance of the structure of the compounds of the present invention is maximized, thereby inducing delocalization of orbitals. Additionally, the compounds of the present invention have a moiety containing three or more phenyl groups (hereinafter referred to as the 'phenyl group-containing moiety') bonded to the other side of the nitrogen-containing heteroaromatic ring moiety. The phenyl group-containing moiety is formed by the bonding of m phenyl groups (3 ≤ m, specifically 3 ≤ m ≤ 10, more specifically 3 ≤ m ≤ 5) and has at least one ortho-bond (e.g., 1,2-phenylene group). As such phenyl group-containing moiety is bonded to nitrogen-containing heteroaromatic ring moiety, the compound of the present invention may be further induced to delocalize orbitals due to strong steric hindrance caused by ortho-bonding within the phenyl group-containing moiety. Therefore, since the compound of the present invention has a LUMO energy level of less than about 2 eV (specifically, 1.5 to 1.95, more specifically about 1.8 to 1.9), it can transport electrons to an adjacent organic layer (e.g., emissive layer) and thus can be used as a material for an electron transport layer or an electron transport auxiliary layer.

[0048] In addition, the compound of the present invention can induce an increase in triplet energy (T1) through maximized steric hindrance. Therefore, when the compound of the present invention is applied to an organic layer of an organic electroluminescent device (particularly an electron transport layer or an electron transport auxiliary layer), excitons are attracted toward the host of the emitting layer, and consequently, the movement (diffusion) of excitons is blocked, thereby improving the efficiency and lifespan of the device.

[0049] In addition, since the compound of the present invention has a wider band gap and a higher triplet energy (T1) level compared to the case having a non-substituted phenanthrene moiety, it can achieve a low driving voltage, high efficiency, and long lifespan of the device even when applied as an electron transport layer or electron transport auxiliary layer material of a blue fluorescent organic electroluminescent device.

[0050] As described above, the compound represented by Formula 1 of the present invention has excellent electron injection and transport capabilities, thermal stability, and electrochemical stability, and can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, an electron transport layer / injection layer material, an electron transport auxiliary layer material, more specifically as an electron transport layer material or an electron transport auxiliary layer material. In addition, the performance and lifespan characteristics of an organic electroluminescent device containing the compound of Formula 1 can be significantly 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.

[0051]

[0052] In the compound represented by Formula 1 according to the present invention, the nitrogen-containing heteroaromatic ring moiety (Z1 to Z3-containing moiety) contains 2 to 3 nitrogen (N) atoms and is an electron-withdrawing group (EWG) with excellent electron transport capability. In the nitrogen-containing heteroaromatic ring moiety, Z1 to Z3 may be identical or different from each other and are each independently N or C (R1), provided that at least two of Z1 to Z3 are N. Due to this nitrogen-containing heteroaromatic ring moiety, the compound of the present invention exhibits excellent electron absorption characteristics, which is advantageous for electron injection and transport.

[0053] For example, the above Z1 to Z3-containing moiety ( The moiety may be selected from the group consisting of the following moiety Az1-1 to Az1-4.

[0054]

[0055] In the above moiety Az1-1 to Az1-4,

[0056] * represents the site that combines with the above chemical formula 1, and

[0057] A and Ar1 are each as defined in Chemical Formula 1 above.

[0058] According to the aforementioned Z1 to Z3, the compound represented by Chemical Formula 1 may be an organic compound represented by any one of the following Chemical Formulas 2 to 9, but is not limited thereto.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] In the above chemical formulas 2 to 9,

[0068] a, b, c, d, e, x, y, z, R2 to R6, n, L1, m. Ar1 and Ar2 are each as defined in Chemical Formula 1 above.

[0069] A moiety (A) containing at least three phenyl groups is directly bonded to one side of the aforementioned nitrogen-containing heteroaromatic ring moiety. The phenyl group-containing moiety (A) is formed by m phenyl groups bonded together (3 ≤ m, specifically 3 ≤ m ≤ 10, more specifically 3 ≤ m ≤ 5) and has at least one ortho-bond. For example, the phenyl group-containing moiety (A) may be a 1,2-phenylene group in which at least one of the m phenyl groups has an ortho-bond. According to one example, the phenyl group-containing moiety is a moiety containing an o-terphenyl group, an o-quaterphenyl group, or a phenyl-o-terphenyl group, specifically a substituent represented by the formula A1-1 or A1-2. Phenyl group-containing moiety having such ortho-bonds can cause strong steric hindrance in the compound of the present invention, inducing orbital delocalization and controlling the LUMO energy level to less than about 2 eV. In this case, the LUMO energy level is expressed as an absolute value.

[0070] In the above chemical formulas A1-1 and A1-2, x, y, and z are each integers from 0 to 3, specifically 0 or 1.

[0071] Also, in the above chemical formulas A1-1 and A1-2, a is an integer from 0 to 3, b, c, and e are each integers from 0 to 5, and d is an integer from 0 to 4.

[0072] Here, if a is 0, it means that the hydrogen is not substituted with substituent R2; if b is 0, it means that the hydrogen is not substituted with substituent R3; if c is 0, it means that the hydrogen is not substituted with substituent R4; if d is 0, it means that the hydrogen is not substituted with substituent R5; and if e is 0, it means that the hydrogen is not substituted with substituent R6. Meanwhile, if a is an integer from 1 to 3, it means that the hydrogen is substituted with substituent R2; if b is an integer from 1 to 5, it means that the hydrogen is substituted with substituent R3; if c is an integer from 1 to 5, it means that the hydrogen is substituted with substituent R4; if d is an integer from 1 to 4, it means that the hydrogen is substituted with substituent R5; and if e is an integer from 1 to 5, it means that the hydrogen is substituted with substituent R6. In this case, the plurality of R2, plurality of R3, plurality of R4, plurality of R5, and plurality of R6 are identical or different from each other.

[0073] R1 to R6 are identical or different from one another, and each independently 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40alkylphosphine group of, C6~C 60 arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, specifically each independently hydrogen, deuterium (D), C1~C 20 alkyl group of, C6~C 30 aryl group, heteroaryl group with 5 to 30 nuclei, C6~C 30 The arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamines, and more specifically, each independently selected from the group consisting of hydrogen, deuterium (D), phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, benzothiazole group, dibenzofuran group, dibenzothiophen group, phenanthrolinyl group and carbazole group.

[0074] According to one example, R1 to R6 are identical or different from each other, and each independently hydrogen or C6~C 30 It can be an aryl group (e.g., phenyl group, biphenyl group, etc.).

[0075] 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, phosphine group, alkylphosphine group, arylphosphine group, phosphine oxide group, alkylphosphine oxide group, arylphosphine oxide group, and arylamine group of the above R1 to R6 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, specifically, 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 20 alkyl group of, C6~C 30 aryl groups, C6 to C with 5 to 30 nuclei 30 The 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 identical or different from each other.

[0076] According to one example, A may be a substituent represented by any one of the following chemical formulas A2-1 to A2-7. However, it is not limited thereto.

[0077]

[0078] In the above chemical formulas A2-1 to A2-7,

[0079] * is the site that binds to the above chemical formula 1, and

[0080] a1 is an integer from 1 to 3, and specifically, a1 can be 1,

[0081] d1 is an integer from 1 to 4, and specifically, d1 can be 1 or 2, and

[0082] x1, y1 and z1 are each integers from 1 to 3, and specifically can be 1.

[0083] According to another example, A may be selected from the group consisting of the following substituents A3-1 to A3-32, provided, but not limited thereto.

[0084]

[0085]

[0086]

[0087]

[0088] In the above substituents A3-1 to A3-32,

[0089] * is the site that is bonded to the above chemical formula 1.

[0090] In the compound represented by Formula 1 according to the present invention, n is an integer from 0 to 4, specifically an integer from 0 to 2.

[0091] Here, when n is 0, it means that L1 is a single link (direct link). On the other hand, when n is an integer from 1 to 4, L1 is a divalent linker, and C1~C 40 alkylene group of, C3~C 40 cycloalkylene group of, C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclei, specifically C1~C 20 alkylene group of, C3~C 20 cycloalkylene group of, C6~C 30 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclei, and more specifically C1~C 12 alkylene group of, C3~C 12 cycloalkylene group of, C6~C 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei. Here, a plurality of L1s may be identical or different from each other.

[0092] At this time, the alkylene group, cycloalkylene group, arylene group, and heteroarylene group of 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, specifically, 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 20 alkyl group of, C6~C 30 aryl group of, C2~C 30 heteroaryl group of, C6~C 30 The 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 identical or different from each other.

[0093] According to one example, the L1 may be a single bond or be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, and combinations thereof. Here, the phenylene group, the biphenylene group, and the terphenylene group are each independently deuterium (D), a halogen (e.g., -F, -Cl, -Br, -I, etc.), a 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 nuclei. Here, multiple L1s may be identical or different from each other.

[0094] According to another example, n is an integer from 1 to 4, and L1 may be the following linker L1-1. In this case, multiple L1s may be identical or different from each other.

[0095]

[0096] In the above linker L1-1,

[0097] f is an integer from 0 to 4, and specifically can be an integer from 0 to 2, and

[0098] 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, specifically deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano groups (-CN), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group of, C6~C 30 It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, more specifically C6~C 30 It can be an aryl group (e.g., phenyl group, biphenyl group, etc.).

[0099] Depending on the aforementioned L1 and its bonding position, the compound represented by Chemical Formula 1 may be an organic compound represented by Chemical Formula 10 or 11 below, but is not limited thereto.

[0100]

[0101]

[0102] In the above chemical formulas 10 and 11,

[0103] A, Z1 to Z3, n, m, Ar1 and Ar2 are each as defined in Chemical Formula 1 above, and

[0104] f is an integer from 0 to 4, and specifically can be an integer from 0 to 2, and

[0105] 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, specifically deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano groups (-CN), C1~C 20 alkyl group of, C3~C 20 cycloalkyl group of, C6~C 30 It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclei, more specifically C6~C 30 It can be an aryl group (e.g., phenyl group, biphenyl group, etc.).

[0106] In the compound represented by Formula 1 according to the present invention, m is an integer from 1 to 9, specifically an integer from 1 to 3, and more specifically 1. In this case, a plurality of Ar2 are identical or different from each other.

[0107] Ar1 and Ar2 are identical or different from each other and each independently contains 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40 alkylphosphine group of, C6~C 60 arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, specifically each independently deuterium (D), C1~C 20 alkyl group of, C6~C 30 aryl group, heteroaryl group with 5–30 nuclei, C6–C 30 The arylphosphine oxide group and C6~C 30It can be selected from the group consisting of arylamines, and more specifically, each independently selected from the group consisting of deuterium (D), phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, phenoxathienyl group, indolizinyl group, indolyl group, purinyl group, quinolyl group, benzothiazole group, dibenzofuran group, dibenzothiophen group, phenanthrolinyl group and carbazole group.

[0108] 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, phosphine group, alkylphosphine group, arylphosphine group, phosphine oxide group, alkylphosphine oxide group, arylphosphine oxide group, and arylamine 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 of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, specifically, 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 20 alkyl group of, C3~C 40 cycloalkyl group of, C6~C 30 aryl group of, C2~C 30 heteroaryl group of, C6~C 30 The 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 identical or different from each other.

[0109] According to one example, m is 1, Ar1 and Ar2 are identical or different from each other, and each independently C6~C 30 The aryl group of may be an aryl group, and the aryl groups of Ar1 and Ar2 are each independently deuterium (D) and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups. In this case, if there are multiple substituents, they may be identical or different from each other.

[0110] According to another example, m is 1, and Ar2 may be selected from the group consisting of a phenyl group, a biphenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a triphenylenyl group. In this case, the phenyl group, biphenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, and triphenylenyl group of Ar2 are deuterium (D) and C6~C 30It may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups. If there are multiple substituents, they may be identical or different from each other.

[0111] According to the aforementioned Ar2, the compound represented by Chemical Formula 1 may be an organic compound represented by any one of Chemical Formulas 12 to 15 below, but is not limited thereto.

[0112]

[0113]

[0114]

[0115]

[0116] In the above chemical formulas 12 to 15,

[0117] a, b, c, d, e, x, y, z, R2 to R6, Z1 to Z3, n, L1, and Ar1 are each as defined in the above Chemical Formula 1, and

[0118] g is 0 or 1.

[0119] According to the aforementioned A and Ar2, the compound represented by Chemical Formula 1 may be an organic compound represented by any one of the following Chemical Formulas 16 to 29, but is not limited thereto.

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In the above chemical formulas 16 to 29,

[0135] Z1 to Z3, n, L1 and Ar1 are each as defined in Chemical Formula 1 above, and

[0136] g is 0 or 1.

[0137] According to the aforementioned A, Z1 to Z3, L1 and Ar2, the compound represented by Chemical Formula 1 may be an organic compound represented by any one of the following Chemical Formulas 30 to 85, but is not limited thereto.

[0138]

[0139]

[0140]

[0141]

[0142]

[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] In the above chemical formulas 30 to 85,

[0195] n and Ar1 are each as defined in the above Chemical Formula 1, and

[0196] f and R are as defined in the above chemical formulas 10 and 11, and

[0197] g is 0 or 1.

[0198] The compound represented by Chemical Formula 1 of the present invention described above may be embodied in the following compounds 1 to 160, but is not limited thereto.

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0208] In the present invention, "alkyl group" refers to a monovalent substituent derived from a straight-chain or side-chain 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.

[0209] In the present invention, "alkenyl group" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0210] In the present invention, "alkynyl group" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0211] In the present invention, "cycloalkyl group" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0212] In the present invention, "heterocycloalkyl group" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholine and piperazine. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0213] In the present invention, "aryl group" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply pendent or condensed may also be included. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0214] In the present invention, "heteroaryl group" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply penant or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, quinazolinyl group, phenanthrolinyl group, and phenanthridyl group; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0215] In the present invention, "alkyloxy group" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0216] In the present invention, "aryloxy group" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such arylsoxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0217] In the present invention, "alkylsilyl group" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyls.

[0218] Also, "arylsilyl group" means a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes polyarylsilyls such as mono-, as well as di- and tri-arylsilyls.

[0219] In the present invention, "alkylboron group" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboron group" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0220] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups.

[0221] In addition, in the present invention, "arylphosphinyl group" refers to a phosphine group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0222] In the present invention, "arylphosphine oxide group" refers to a phosphine oxide group substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0223] In the present invention, "arylamine group" refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamines.

[0224] In the present invention, "condensed ring" refers to 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 nuclei, a condensed heteroaromatic ring having 5 to 60 nuclei, C3~C 60 It refers to a spyro ring or a combination thereof. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the number of ring atoms.

[0225]

[0226] Organic Electroluminescent Device

[0227] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter referred to as an 'organic EL device') comprising a compound represented by the aforementioned chemical formula 1.

[0228] Specifically, the organic electroluminescent device according to the present invention comprises, as illustrated in FIGS. 1 to 3, an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1. At this time, the compound may be used alone or two or more may be used in combination.

[0229] The above-mentioned organic layer (300) may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport assist layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layer (300) comprises a compound represented by the above-mentioned chemical formula 1. Specifically, the organic layer comprising the compound of the above-mentioned chemical formula 1 may be at least one of the electron transport layer (340) and the electron transport assist layer (360).

[0230] According to one example, the above-described organic layer comprises a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer, and may optionally further comprise an electron transport assisting layer. The electron transport layer comprises a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons are easily injected from the cathode or electron injection layer to the electron transport layer due to the compound of Chemical Formula 1, and can also move rapidly from the electron transport layer to the emitting layer, resulting in a high coupling force between holes and electrons in the emitting layer. Therefore, the organic electroluminescent device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. Furthermore, the compound of Chemical Formula 1 has excellent thermal stability and electrochemical stability, which can improve the performance of the organic electroluminescent device.

[0231] The compound of Formula 1 as described above may be used alone or in combination with electron transport layer materials known in the art.

[0232] In the present invention, electron transport layer materials that can be mixed with the compound of Formula 1 include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq 3, Examples include tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used individually or in combination of two or more types.

[0233] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0234] According to another example, the above-described organic layer comprises a hole injection layer, a hole transport layer, an emissive layer, an electron transport assist layer, an electron transport layer, and an electron injection layer, wherein the electron transport assist layer comprises a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included in the organic electroluminescent device as an electron transport assist layer material. In this case, the compound of Chemical Formula 1 has a high triplet energy. For this reason, when the compound of Chemical Formula 1 is included as an electron transport assist layer material, the efficiency of the organic electroluminescent device can be increased due to the triplet-triplet fusion (TTF) effect. In addition, the compound of Chemical Formula 1 can prevent excitons or holes generated in the emissive layer from diffusing into the electron transport layer adjacent to the emissive layer. Therefore, the number of excitons contributing to light emission within the emissive layer increases, thereby improving the luminous efficiency of the device, and the durability and stability of the device are enhanced, thereby efficiently increasing the lifespan of the device.

[0235] The compound of Formula 1 as described above may be used alone or in combination with electron transport layer auxiliary layer materials known in the art.

[0236] In the present invention, electron transport auxiliary layer materials that can be mixed with the compound of Formula 1 include electron transport materials commonly known in the field, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives, but are not limited thereto.

[0237] 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 stacked on a substrate (see FIGS. 1 to 3). In addition, although not shown, the structure may have an insulating layer or an adhesive layer inserted at the interface between the electrode and the organic layer.

[0238] According to one 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 stacked on a substrate, as shown in FIG. 1. Optionally, as shown in FIG. 2, an electron injection layer (350) may be located between the electron transport layer (340) and the cathode (200). Additionally, an electron transport auxiliary layer (360) may be located between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0239] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., a light-emitting layer (330), an electron transport layer (340), or an electron transport auxiliary layer (360)] comprises a compound represented by the chemical formula 1.

[0240] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0241] The substrates usable in the present invention are not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0242] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0243] Also, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0244] In addition, the hole injection layer, hole transport layer, light-emitting layer, and electron injection layer are not particularly limited, and ordinary materials known in the industry may be used.

[0245]

[0246] The present invention will be explained in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0247] [Preparation Example 1] Synthesis of ST-1

[0248]

[0249] 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine (40.0 g, 132.5 mmol), [1,1':2',1''-terphenyl]-3'-ylboronic acid (36.3 g, 132.5 mmol), Pd(PPh3)4 (4.6 g, 4.0 mmol), and K2CO3 (36.6 g, 264.9 mmol) were added to a mixed solvent of 400 ml of dioxane and 80 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound ST-1 (42.8 g, yield 65%).

[0250] 1H-NMR: δ 8.36(d, 2H), 8.06(d, 2H), 7.93(t, 1H), 7.80-7.41(m, 17H)

[0251] Mass: [(M+H)+] : 497

[0252]

[0253] [Preparation Example 2] Synthesis of ST-2

[0254]

[0255] Compound ST-2 (43.4 g, yield 66%) was obtained by performing the same procedure as in Preparation Example 1, except that 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of the compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine used in Preparation Example 1, and (6'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)boronic acid was used instead of the compound [1,1':2',1''-terphenyl]-3'-ylboronic acid.

[0256] 1H-NMR: δ 8.36(d, 2H), 8.25(s, 2H), 8.16(d, 1H), 7.97(s, 1H), 7.79(d, 2H), 7.65-7.41(m, 18H)

[0257] Mass: [(M+H)+] : 573

[0258]

[0259] [Preparation Example 3] Synthesis of ST-3

[0260]

[0261] Compound ST-3 (44.1 g, yield 67%) was obtained by performing the same procedure as in Preparation Example 1, except that 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine was used instead of the compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine used in Preparation Example 1, and [1,1':2',1'':2'',1'''-quaterphenyl]-4-ylboronic acid was used instead of the compound [1,1':2',1''-terphenyl]-3'-ylboronic acid.

[0262] 1H-NMR: δ 8.36(d, 2H), 8.25(d, 2H), 7.96(d, 6H), 7.79(d, 2H), 7.60-7.41(m, 12H), 7.25(d, 2H)

[0263] Mass: [(M+H)+] : 573

[0264]

[0265] [Preparation Example 4] Synthesis of ST-4

[0266]

[0267] Compound ST-4 (42.8 g, yield 65%) was obtained by performing the same procedure as in Preparation Example 1, except that 4-chloro-2-(2-chlorophenyl)-6-phenylpyrimidine was used instead of the compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine used in Preparation Example 1, and [1,1':2',1''-terphenyl]-4'-ylboronic acid was used instead of the compound [1,1':2',1''-terphenyl]-3'-ylboronic acid.

[0268] 1H-NMR: δ 8.40(d, 1H), 8.23(s, 1H), 8.15-8.13(m, 2H), 7.94(d, 2H), 7.79(d, 4H), 7.71(d, 1H), 7.55-7.38(m, 12H)

[0269] Mass: [(M+H)+] : 496

[0270]

[0271] [Preparation Example 5] Synthesis of ST-5

[0272]

[0273] Compound ST-5 (40.8g, yield 62%) was obtained by performing the same procedure as in Preparation Example 1, except that 2-chloro-4-(3-chlorophenyl)-6-phenylpyrimidine was used instead of the compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine used in Preparation Example 1, and (6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)boronic acid was used instead of the compound [1,1':2',1''-terphenyl]-3'-ylboronic acid.

[0274] 1H-NMR: δ 8.23 ​​(s, 3H), 7.97-7.94 (m, 3H), 7.79-7.72 (m, 7H), 7.55-7.41 (m, 14H)

[0275] Mass: [(M+H)+] : 572

[0276]

[0277] [Preparation Example 6] Synthesis of ST-6

[0278]

[0279] Compound ST-6 (41.1 g, yield 62%) was obtained by performing the same procedure as in Preparation Example 1, except that 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine was used instead of the compound 2-chloro-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine used in Preparation Example 1, and [1,1':2',1''-terphenyl]-3'-ylboronic acid was used instead of the compound [1,1':2',1'':3'',1'''-quaterphenyl]-3-ylboronic acid.

[0280] 1H-NMR: δ 8.35 (d, 2H), 8.23 ​​(s, 1H), 7.97-7.94 (m, 7H), 7.75-7.73 (m, 4H), 7.60-7.41 (m, 13H)

[0281] Mass: [(M+H)+] : 572

[0282]

[0283] [Synthesization Example 1] Synthesis of Compound 5

[0284]

[0285] Compound ST-1 (5.0 g, 10.1 mmol) obtained in Preparation Example 1, (1-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) were added to 50 ml of Dioxane and 10 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 5 (3.2 g, yield 44%).

[0286] Mass: [(M+H)+] : 715

[0287]

[0288] [Synthesization Example 2] Synthesis of Compound 12

[0289]

[0290] Compound 12 (3.0 g, yield 41%) was obtained by performing the same procedure as in Synthesis Example 1, except that (5-phenylphenanthren-3-yl)boronic acid was used instead of (1-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 1.

[0291] Mass: [(M+H)+] : 715

[0292]

[0293] [Synthesization Example 3] Synthesis of Compound 19

[0294]

[0295] Compound 19 (3.1g, yield 43%) was obtained by performing the same procedure as in Synthesis Example 1, except that compound ST-2 obtained in Preparation Example 2 was used instead of compound ST-1 used in Synthesis Example 1, and (8-phenylphenanthren-1-yl)boronic acid was used instead of compound (1-phenylphenanthren-2-yl)boronic acid.

[0296] Mass: [(M+H)+] : 791

[0297]

[0298] [Synthesization Example 4] Synthesis of Compound 42

[0299]

[0300] Compound 42 (2.9 g, yield 40%) was obtained by performing the same procedure as in Synthesis Example 3, except that (10-phenylphenanthren-4-yl)boronic acid was used instead of (8-phenylphenanthren-1-yl)boronic acid used in Synthesis Example 3.

[0301] Mass: [(M+H)+] : 791

[0302]

[0303] [Synthesization Example 5] Synthesis of Compound 43

[0304]

[0305] Compound 43 (3.1g, yield 43%) was obtained by performing the same procedure as in Synthesis Example 1, except that compound ST-3 obtained in Preparation Example 3 was used instead of compound ST-1 used in Synthesis Example 1, and (8-phenylphenanthren-2-yl)boronic acid was used instead of compound (1-phenylphenanthren-2-yl)boronic acid.

[0306] Mass: [(M+H)+] : 791

[0307]

[0308] [Synthesization Example 6] Synthesis of Compound 44

[0309]

[0310] Compound 44 (3.0 g, yield 41%) was obtained by performing the same procedure as in Synthesis Example 5, except that (6-phenylphenanthren-4-yl)boronic acid was used instead of (8-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 5.

[0311] Mass: [(M+H)+] : 791

[0312]

[0313] [Synthesization Example 7] Synthesis of Compound 46

[0314]

[0315] Compound 46 (2.8g, yield 39%) was obtained by performing the same procedure as in Synthesis Example 1, except that (2-(10-phenylphenanthren-2-yl)phenyl)boronic acid was used instead of (1-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 1.

[0316] Mass: [(M+H)+] : 791

[0317]

[0318] [Synthesization Example 8] Synthesis of Compound 62

[0319]

[0320] Compound 62 (3.0 g, yield 41%) was obtained by performing the same procedure as in Synthesis Example 3, except that (3-(3-phenylphenanthren-2-yl)phenyl)boronic acid was used instead of (8-phenylphenanthren-1-yl)boronic acid used in Synthesis Example 3.

[0321] Mass: [(M+H)+] : 867

[0322]

[0323] [Synthesization Example 9] Synthesis of Compound 71

[0324]

[0325] Compound 71 (3.0 g, yield 41%) was obtained by performing the same procedure as in Synthesis Example 5, except that (2-(4-phenylphenanthren-3-yl)phenyl)boronic acid was used instead of (8-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 5.

[0326] Mass: [(M+H)+] : 867

[0327]

[0328] [Synthesization Example 10] Synthesis of Compound 85

[0329]

[0330] Compound 85 (2.7g, yield 38%) was obtained by performing the same procedure as in Synthesis Example 1, except that compound ST-4 obtained in Preparation Example 4 was used instead of compound ST-1 used in Synthesis Example 1, and (1-phenylphenanthren-2-yl)boronic acid was used instead of compound (1-phenylphenanthren-2-yl)boronic acid.

[0331] Mass: [(M+H)+] : 714

[0332]

[0333] [Synthesization Example 11] Synthesis of Compound 92

[0334]

[0335] Compound 92 (2.8g, yield 39%) was obtained by performing the same procedure as in Synthesis Example 10, except that (5-phenylphenanthren-3-yl)boronic acid was used instead of (1-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 10.

[0336] Mass: [(M+H)+] : 714

[0337]

[0338] [Synthesization Example 12] Synthesis of Compound 99

[0339]

[0340] Compound 99 (2.7g, yield 38%) was obtained by performing the same procedure as in Synthesis Example 1, except that compound ST-5 obtained in Preparation Example 5 was used instead of compound ST-1 used in Synthesis Example 1, and (8-phenylphenanthren-1-yl)boronic acid was used instead of compound (1-phenylphenanthren-2-yl)boronic acid.

[0341] Mass: [(M+H)+] : 790

[0342]

[0343] [Synthesization Example 13] Synthesis of Compound 122

[0344]

[0345] Compound 122 (2.5 g, yield 35%) was obtained by performing the same procedure as in Synthesis Example 12, except that (10-phenylphenanthren-4-yl)boronic acid was used instead of (8-phenylphenanthren-1-yl)boronic acid used in Synthesis Example 12.

[0346] Mass: [(M+H)+] : 790

[0347]

[0348] [Synthesization Example 14] Synthesis of Compound 123

[0349]

[0350] Compound 123 (2.7g, yield 38%) was obtained by performing the same procedure as in Synthesis Example 1, except that compound ST-6 obtained in Preparation Example 6 was used instead of compound ST-1 used in Synthesis Example 1, and (8-phenylphenanthren-2-yl)boronic acid was used instead of compound (1-phenylphenanthren-2-yl)boronic acid.

[0351] Mass: [(M+H)+] : 790

[0352]

[0353] [Synthesization Example 15] Synthesis of Compound 124

[0354]

[0355] Compound 124 (2.7 g, yield 37%) was obtained by performing the same procedure as in Synthesis Example 14, except that (6-phenylphenanthren-4-yl)boronic acid was used instead of (8-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 14.

[0356] Mass: [(M+H)+] : 790

[0357]

[0358] [Synthesization Example 16] Synthesis of Compound 126

[0359]

[0360] Compound 126 (2.8g, yield 39%) was obtained by performing the same procedure as in Synthesis Example 10, except that (2-(10-phenylphenanthren-2-yl)phenyl)boronic acid was used instead of (1-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 10.

[0361] Mass: [(M+H)+] : 790

[0362]

[0363] [Synthesization Example 17] Synthesis of Compound 142

[0364]

[0365] Compound 142 (2.5 g, yield 35%) was obtained by performing the same procedure as in Synthesis Example 12, except that (3-(3-phenylphenanthren-2-yl)phenyl)boronic acid was used instead of (8-phenylphenanthren-1-yl)boronic acid used in Synthesis Example 12.

[0366] Mass: [(M+H)+] : 866

[0367]

[0368] [Synthesization Example 18] Synthesis of Compound 151

[0369]

[0370] Compound 151 (2.7 g, yield 37%) was obtained by performing the same procedure as in Synthesis Example 14, except that (2-(4-phenylphenanthren-3-yl)phenyl)boronic acid was used instead of (8-phenylphenanthren-2-yl)boronic acid used in Synthesis Example 14.

[0371] Mass: [(M+H)+] : 866

[0372]

[0373] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0374] Compound 5 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was fabricated according to the following process.

[0375] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0376] An organic electroluminescent device was fabricated 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 5 + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above. The structures of the compounds HI, HAT-CN6, EB, BH, BD, and Liq used at this time are as follows.

[0377]

[0378]

[0379] [Examples 2 to 18] Preparation of Blue Organic Electroluminescent Devices

[0380] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 5, which was used as the electron transport layer material in Example 1.

[0381]

[0382] [Comparative Examples 1 to 10] Preparation of blue organic electroluminescent devices

[0383] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that Alq3 and compounds PN-1 to PN-9 were used instead of compound 5, which was used as the electron transport layer material in Example 1. The structures of Alq3 and compounds PN-1 to PN-9 used at this time are as follows.

[0384]

[0385]

[0386] [Evaluation Example 1]

[0387] For the organic electroluminescent devices prepared in Examples 1 to 18 and Comparative Examples 1 to 10, respectively, 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.

[0388] Sample Electron Transport Layer Material Driving Voltage (V) Luminance Peak (nm) Current Efficiency (cd / A) Example 1 Compound 53.34547.8 Example 2 Compound 123.44558.0 Example 3 Compound 193.34548.0 Example 4 Compound 423.34557.9 Example 5 Compound 433.44547.8 Example 6 Compound 443.44548.0 Example 7 Compound 463.44557.9 Example 8 Compound 623.34548.0 Example 9 Compound 713.44547.9 Example 10 Compound 853.34557.8 Example 11 Compound 923.34547.8 Example 12 Compound 993.54547.9 Example 13 Compound 1223.44557.9 Example 14 Compound 1233.44558.0 Example 15 Compound 1243.54547.9 Example 16 Compound 1263.44558.0 Example 17 Compound 1423.44547.9 Example 18 Compound 1513.34558.0 Comparative Example 1 Alq34.64575.6 Comparative Example 2 PN-14.34586.9 Comparative Example 3 PN-24.24576.8 Comparative Example 4 PN-34.24566.8 Comparative Example 5PN-44.34576.8 Comparative Example 6PN-54.24586.9 Comparative Example 7PN-64.34566.8 Comparative Example 8PN-74.44566.7 Comparative Example 9PN-84.24566.8 Comparative Example 10PN-94.34576.7

[0389] As shown in Table 1, it was confirmed that the organic light-emitting devices prepared in Examples 1 to 18 had superior driving voltage, emission peak, and current efficiency compared to the organic light-emitting devices prepared in Comparative Examples 1 to 10.

[0390]

[0391] [Example 19] Fabrication of a Blue Organic Electroluminescent Device

[0392] Compound 5 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and then a blue organic electroluminescent device was fabricated according to the following process.

[0393] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0394] An organic electroluminescent device was fabricated 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 5 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above. The structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used at this time are as follows.

[0395]

[0396]

[0397] [Examples 20 to 36] Preparation of Blue Organic Electroluminescent Devices

[0398] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 19, except that the compounds listed in Table 2 below were used instead of Compound 5, which was used as the electron transport auxiliary layer material in Example 19.

[0399]

[0400] [Comparative Example 11] Preparation of a blue organic electroluminescent device

[0401] A blue organic electroluminescent device was fabricated in the same manner as in Example 19, except that compound 5, which was used as the electron transport auxiliary layer material in Example 19, was not used, and the electron transport layer [ET + Liq (1:1 weight ratio)] was formed to a thickness of 35 nm instead of 30 nm.

[0402]

[0403] [Comparative Examples 12 to 20] Preparation of a blue organic electroluminescent device

[0404] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 19, except that compounds PN-1 to PN-9 were used respectively instead of compound 5, which was used as the electron transport auxiliary layer material in Example 19. The structures of compounds PN-1 to PN-9 used at this time are the same as those described in Comparative Examples 1 to 10.

[0405]

[0406] [Evaluation Example 2]

[0407] For the organic electroluminescent devices prepared in Examples 19 to 36 and Comparative Examples 11 to 20, respectively, 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.

[0408] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 19 Compound 53.24558.1 Example 20 Compound 123.14548.1 Example 21 Compound 193.24548.0 Example 22 Compound 423.34558.2 Example 23 Compound 433.24558.2 Example 24 Compound 443.24548.1 Example 25 Compound 463.34558.2 Example 26 Compound 623.14548.1 Example 27 Compound 713.24558.0 Example 28 Compound 853.24548.1 Example 29 Compound 923.34558.0 Example 30 Compound 993.24548.0 Example 31 Compound 1223.24548.1 Example 32 Compound 1233.34558.0 Example 33 Compound 1243.24548.1 Example 34 Compound 1263.14548.1 Example 35 Compound 1423.34558.0 Example 36 Compound 1513.24548.0 Comparative Example 11 -4.64566.3 Comparative Example 12 PN -14.14576.8 Comparative Example 13 PN -24.04576.9 Comparative Example 14 PN -34.04566.8 Comparative Example 15PN-44.14566.9 Comparative Example 16PN-54.24566.9 Comparative Example 17PN-64.14576.8 Comparative Example 18PN-74.14576.9 Comparative Example 19PN-84.14586.9 Comparative Example 20PN-94.24576.8

[0409] As shown in Table 2, it was confirmed that the organic light-emitting devices prepared in Examples 19 to 36 had superior driving voltage, emission peak, and current efficiency compared to the organic light-emitting devices prepared in Comparative Examples 11 to 20.

Claims

1. Organic compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, Z1 to Z3 are identical or different from each other, and each is independently N or C(R1), provided that at least two of Z1 to Z3 are N, A is a substituent represented by the following chemical formula A1-1 or A1-2, and [Chemical Formula A1-1] [Chemical Formula A1-2] In the above chemical formulas A1-1 and A1-2, a is an integer from 0 to 3, and b, c, and e are each integers from 0 to 5, and d is an integer from 0 to 4, and x, y, and z are integers from 0 to 3, respectively, and R1 to R6 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40 alkylphosphine group of, C6~C 60 arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, n is an integer from 0 to 4, and Multiple L1s are identical or different from each other, and L1 is a single bond, or C1~C 40 alkylene group of, C3~C 40 cycloalkylene group of, C6~C 30 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclei, m is an integer from 1 to 9, and Ar1 and Ar2 are identical or different from each other, and each independently contains deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine group, C1~C 40 alkylphosphine group of, C6~C 60 arylphosphine group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, phosphine groups, alkylphosphine groups, arylphosphine groups, phosphine oxide groups, alkylphosphine oxide groups, arylphosphine oxide groups, and arylamine groups of R1 to R6, Ar1, and Ar2, and the alkylene groups, cycloalkylene groups, arylene groups, and heteroarylene groups of L1 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl 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 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other).

2. In Paragraph 1, A is an organic compound that is a substituent represented by any one of the chemical formulas A2-1 to A2-7: (in the above chemical formulas A2-1 to A2-7, * is the site that binds to the above chemical formula 1, and a1 is an integer from 1 to 3, and d1 is an integer from 1 to 4, and x1, y1, and z1 are each integers from 1 to 3).

3. In Paragraph 1, The above Organic compound, wherein the moiety is selected from the group consisting of the following moiety Az1-1 to Az1-4: (In the above moiety Az1-1 to Az1-4, A and Ar1 are each as defined in Paragraph 1).

4. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 2 to 9: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] (In the above chemical formulas 2 to 9, a, b, c, d, e, x, y, z, R2 to R6, n, L1, m, Ar1 and Ar2 are each as defined in Paragraph 1).

5. In Paragraph 1, n is an integer from 1 to 4, and Multiple L1s are identical or different from each other, and L1 is an organic compound in which the following linker group L1-1 is: (In the above linker L1-1, f is an integer from 0 to 4, and R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 (Selected from the group consisting of arylamine groups).

6. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by the following chemical formula 10 or 11: [Chemical Formula 10] [Chemical Formula 11] (In the above chemical formulas 10 and 11, A, Z1 to Z3, n, m, Ar1 and Ar2 are each as defined in Paragraph 1, and f is an integer from 0 to 4, and R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 (Selected from the group consisting of arylamine groups).

7. In Paragraph 1, m is 1 and, Ar1 and Ar2 are identical or different from each other, and each independently C6~C 60 The aryl group of, organic compound.

8. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 12 to 15: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] (In the above chemical formulas 12 to 15, a, b, c, d, e, x, y, z, R2 to R6, Z1 to Z3, n, L1 and Ar1 are each as defined in claim 1, and g is 0 or 1).

9. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 16 to 29: [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] (In the above chemical formulas 16 to 29, Z1 to Z3, n, L1 and Ar1 are each as defined in Paragraph 1, and g is 0 or 1).

10. In Paragraph 1, An organic compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 30 to 85: [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] (In the above chemical formulas 30 to 85, n and Ar1 are each as defined in Paragraph 1, and f is an integer from 0 to 4, and R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, g is 0 or 1).

11. In Paragraph 1, The compound represented by the above chemical formula 1 is an organic compound selected from the group consisting of the following compounds 1 to 160: .

12. Anode; cathode; comprising one or more organic layers interposed between the anode and the cathode, and An organic electroluminescent device comprising at least one of the above one or more organic layers, wherein the organic compound described in any one of claims 1 to 11.

13. In Paragraph 12, An organic electroluminescent device in which the organic layer containing the above organic compound is an electron transport layer or an electron transport auxiliary layer.

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