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 transportability, lumminescence ability, and the like; and an organic electroluminescent device having improved characteristics in terms of luminescence efficiency, driving voltage, lifespan, and the like due to inclusion of the organic compound in one or more organic material layers.

Description

Organic compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic compound having excellent electron transport 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, as a luminescent layer material, a life-span improving layer material, a luminescent auxiliary layer material, an electron transport layer material or an electron transport auxiliary layer material, and more specifically, as an electron transport layer material or an electron transport auxiliary layer material.

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

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

[0010]

[0011] (In the above chemical formula 1,

[0012] EWG stands for electron withdrawing group;

[0013] L1 and L2 are the same or different, and each independently represents a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 3 to 18 nuclear atoms;

[0014] a is an integer from 3 to 5,

[0015] A plurality of Ar1s are the same or different from each other, and each independently represents a phenylene group or a naphthalene group,

[0016] However, at most two of the plurality of Ar1s are selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group and a 2,3-naphthalene group having an ortho-bond, wherein the ortho-bonds are discontinuous;

[0017] Ring Cy1 is present or absent, and when ring Cy1 is present, ring Cy1 is a six-membered fused aromatic ring;

[0018] Moiety When bonded in an ortho-position to a moiety, b is an integer from 0 to 3, Ar2 is a phenylene group or a naphthalene group, Ar3 is a phenyl group or a naphthyl group, provided that among at least one Ar2, the Ar2 closest to the ring Cy1-condensed benzene ring is selected from the group consisting of a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group and a 2,4-naphthalene group having a meta- or para-bond;

[0019] Moiety When bonded to a moiety in a meta- or para-position, b is an integer of 1 to 3, Ar2 is a phenylene group or a naphthalene group, Ar3 is a phenyl group or a naphthyl group, provided that at least one of the one or more Ar2s is selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group and a 2,3-naphthalene group having an ortho-bond;

[0020] c is 0 or 1,

[0021] d is an integer from 0 to 2,

[0022] However, 0≤ b+d ≤ 3;

[0023] Moiety is Moiety or is bonded in the ortho-position to the moiety, Ar4 is a phenylene group or a naphthalene group, and Ar5 is a phenyl group or a naphthyl group;

[0024] e is an integer from 0 to 5,

[0025] R1 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 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,

[0026] The arylene group and heteroarylene group of the above L1 and L2, the phenylene group and naphthalene group of the above Ar1, Ar2 and Ar4, and the phenyl group or naphthyl group of the above Ar3 and Ar5 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, 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).

[0027] 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.

[0028] In one example, the organic layer containing the compound may be an electron transport layer or an electron transport auxiliary layer.

[0029] 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.

[0030] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

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

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

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

[0034] <Explanation of symbols>

[0035] 100: anode, 200: cathode,

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

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

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

[0039] 360: Electron transport auxiliary layer

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

[0041] <New organic compounds>

[0042] The present invention provides a compound having a basic structure comprising: a first moiety composed of 3 to 5 phenylene groups and / or naphthalene groups, wherein the first moiety has at most 2 discontinuous ortho-bonds; an EWG bonded directly or via a linker group to one side of the core; and a second moiety bonded directly or via a linker group to the other side of the core, wherein the second moiety has at most 2 discontinuous ortho-bonds and is composed of 3 to 5 phenylene groups and / or naphthalene groups, and is represented by the above chemical formula 1. The compound of the present invention has excellent electron injection and transport ability, electrochemical stability, thermal stability, carrier transport ability, and luminescence ability, and thus can be used as a high-efficiency organic layer material, particularly an electron transport layer material or an electron transport auxiliary layer material.

[0043] In the compound according to the present invention, the first moiety and the second moiety are both composed of 3 to 5 phenylene groups and / or naphthalene groups, and have at most 2 non-consecutive ortho-bonds. Specifically, the first moiety and the second moiety are composed of 3 to 5 phenylene groups and / or naphthalene groups, of which at most 2 may be selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group, or a 2,3-naphthalene group having ortho-bonds. In this way, since the first and second moieties have at most 2 ortho-bonds, the compound of the present invention has a relatively shallow LUMO energy level, a wide band gap, and a high triplet energy (T1) value, so that the electron injection and transport properties of the compound can be improved. Therefore, when the compound of the present invention is applied to an electron transport layer or an electron transport auxiliary layer of an organic electroluminescent device, the driving voltage as well as the current efficiency of the device can be improved.

[0044] In addition, in the present invention, a 1,2-phenylene group (or a 1,2-naphthalene group or a 2,3-naphthalene group) having an ortho-bond and a 1,2-phenylene group (or a 1,2-naphthalene group or a 2,3-naphthalene group) having an ortho-bond are not connected continuously, but are connected via a meta-bond or a para-bond. In this way, the compound of the present invention has a moiety in which the first and second moieties have at most two discontinuous ortho-bonds, so that, compared to a compound having a moiety in which all 4 to 5 aryl groups (e.g., phenylene groups, naphthalene groups) are connected via ortho-bonds, the HOMO region between the ortho-bonds is strengthened, thereby increasing the electron injection characteristics and dipole moment of the molecule, thereby also increasing the carrier mobility.

[0045] In addition, since the compound of the present invention is mainly composed of 3 to 5 phenylene groups and / or naphthalene groups, the compound has excellent structural stability and thermal stability.

[0046] In addition, since the compound represented by Chemical Formula 1 of the present invention has a high triplet energy as described above, 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 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. Most of the developed materials exhibit physical characteristics that allow for low-voltage operation, thereby improving the lifespan.

[0047] As described above, the compound represented by the chemical formula 1 of the present invention has excellent electron transport ability, thermal stability, electrochemical stability, etc., and can be applied as an organic layer material of an organic electroluminescent device, preferably an emitting layer material (a blue, green, and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, an emitting auxiliary layer material, a life-span improvement layer material, an electron transport auxiliary layer material, and more preferably an electron transport layer material or an electron transport auxiliary layer material. In this case, the performance and life-span characteristics of the organic electroluminescent device can be greatly improved, and the performance of a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also be maximized.

[0048] In the compound represented by chemical formula 1 according to the present invention, EWG is an electron withdrawing group, which is a functional group having a Hammett's substituent constant (σ) greater than 0.

[0049] Examples of such EWGs may include, but are not limited to, those selected from the group consisting of the following substituents EWG1 to EWG10.

[0050]

[0051] In the above substituents EWG1 to EWG10,

[0052] * indicates the part that is combined with chemical formula 1.

[0053] X1 to X3 are the same or different from each other, and are each independently N or C(R8), provided that at least one of X1 to X3 is N,

[0054] Y1 is O or S,

[0055] X4 and X5 are the same or different, and each independently represents N or C(R9), provided that at least one of X4 and X5 is N,

[0056] X6 and X7 are the same or different, and each independently represents N or C(R10 ) and at least one of X6 and X7 is N,

[0057] R2 to R 10 are identical 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 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group of , heteroaryl group of 5 to 18 nuclear atoms and C6~C 18 It may be selected from the group consisting of arylamine groups, and more specifically, it may be selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, and specifically, it may be a phenyl group or a naphthyl group.

[0058] Specifically, R2 to R 10are the same or different from each other, and each independently can 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.

[0059] For example, the EWG may be selected from the group consisting of the following substituents EWG1-1 to EWG10-3, but is not limited thereto.

[0060]

[0061]

[0062]

[0063] In the above substituents EWG1-1 to EWG10-3,

[0064] * indicates the part that is combined with chemical formula 1.

[0065] Y1 is O or S.

[0066] The hydrogens of the above substituents EWG1-1 to EWG10-3 are each deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 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.

[0067] In the chemical formula 1 according to the present invention, L1 and L2 are the same or different from each other, and each independently represents a single bond (direct bond), or C6~C 18Selected from the group consisting of an arylene group and a heteroarylene group having 3 to 18 nuclear atoms, and specifically each is a single bond, or C6~C 18 It can be selected from the group consisting of arylene groups.

[0068] At this time, the arylene group and heteroarylene group of L1 and L2 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 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 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.

[0069] In one embodiment, L1 and L2 are the same as or different from each other, and can each independently be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a divalent naphthalene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent carbazole group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent fluorene group, and combinations thereof. Here, the hydrogen of the phenylene group, biphenylene group, terphenylene group, divalent naphthalene group, divalent phenanthrene group, divalent triphenylene group, divalent carbazole group, divalent dibenzofuran group, divalent dibenzothiophene group, and divalent fluorene group is each replaced by deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1~C 12 Alkyl group of C6~C 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.

[0070] In another example, L1 and L2 may be the same or different, and may each independently be a single bond or a linker group represented by the following chemical formula L, but is not limited thereto.

[0071] [Chemical formula L]

[0072]

[0073] In the above chemical formula L,

[0074] * indicates the part that is combined with chemical formula 1.

[0075] n is an integer from 1 to 4, specifically an integer from 1 to 3,

[0076] i is an integer from 0 to 4, specifically 0 or 1,

[0077] Multiple R's are the same or different from each other,

[0078] 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, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups.

[0079] According to another example, L1 may be a single bond, or a divalent linker group having a meta- or para-bond, such as a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group or a 2,4-naphthalene group, when one or more of the adjacent Ar1s are 1,2-phenylene groups, 1,2-naphthalene groups and 2,3-naphthalene groups having an ortho-bond.

[0080] According to another example, L2 may be a single bond, or a divalent linker group having a meta- or para-bond, such as a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group or a 2,4-naphthalene group, when one or more of the adjacent Ar1s are 1,2-phenylene groups, 1,2-naphthalene groups and 2,3-naphthalene groups having an ortho-bond.

[0081] In the chemical formula 1 according to the present invention, a is an integer of 3 to 5, and a plurality of Ar1s are the same or different from each other, and are each independently a phenylene group or a naphthalene group. However, at most two of the plurality of Ar1s are selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group, and a 2,3-naphthalene group having an ortho-bond, wherein the ortho-bonds are discontinuous.

[0082] As an example, the above The moiety may be, but is not limited to, a moiety represented by the following chemical formula A.

[0083] [Chemical Formula A]

[0084]

[0085] In the above chemical formula A,

[0086] * indicates the part that is combined with chemical formula 1.

[0087] Rings Q1 to Q3 are each present or non-existent, and when rings Q1 to Q3 are each present, rings Q1 to Q3 are each a 6-membered condensed aromatic ring condensed to a benzene ring,

[0088] The moiety binds at the meta- or para-position,

[0089] f and g are 0 or 1, respectively,

[0090] Ar6 and Ar7 are the same or different, and each independently represents a phenylene group or a naphthalene group,

[0091] The plurality of h are each an integer from 0 to 6, specifically, each can be an integer from 0 to 3, and more specifically, each can be 0 or 1,

[0092] Multiple R are the same or different, 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 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, and specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It can be selected from the group consisting of arylamine groups,

[0093] The phenylene group and naphthalene group of the above Ar6 and Ar7 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 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0094] In the above chemical formula A, a plurality of R's are the same or different from each other, and can each independently 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.

[0095] According to an example, the moiety represented by the above chemical formula A may be a moiety represented by any one of the following chemical formulas A1 to A5, but is not limited thereto.

[0096] [Chemical Formula A1]

[0097]

[0098] [Chemical Formula A2]

[0099]

[0100] [Chemical Formula A3]

[0101]

[0102] [Chemical Formula A4]

[0103]

[0104] [Chemical Formula A5]

[0105]

[0106] In the above chemical formulas A1 to A5,

[0107] * indicates the part that is combined with chemical formula 1.

[0108] Rings Q1 to Q3, multiple h, and multiple R are each as defined in the above chemical formula A,

[0109] Rings Q4 and Q5 are each present or absent, and when rings Q1 to Q5 are each present, rings Q1 to Q5 are each a 6-membered fused aromatic ring. Here, the 6-membered fused aromatic ring is a ring fused to a benzene ring.

[0110] According to another example, the moiety represented by the above chemical formula A may be selected from the group consisting of the following moieties Mo1-1 to mo1-70, but is not limited thereto.

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] In the above moieties Mo1-1 to Mo1-70,

[0124] * indicates the part that is combined with chemical formula 1.

[0125] Plural h and plural R are as defined in the above chemical formulas A1 to A5, respectively,

[0126] The plurality of h1s are each an integer from 0 to 4, and specifically, each can be an integer from 0 to 2,

[0127] Rings Q1 to Q5 are the same or different, and each is a 6-membered fused aromatic ring.

[0128] The above chemical formula 1 according to the present invention In the moiety, ring Cy1 is either present or absent. If ring Cy1 is present, ring Cy1 is a six-membered fused aromatic ring fused to a benzene ring.

[0129] In this way, depending on the presence or absence of ring Cy1, The moiety may be the following moiety Mo2-1 or Mo2-2.

[0130]

[0131] In the above moieties Mo2-1 and Mo2-2,

[0132] * indicates the part that is combined with chemical formula 1.

[0133] b, c, d, and e are each as defined in the above chemical formula 1,

[0134] e1 is an integer from 0 to 3, specifically 0 or 1.

[0135] In the chemical formula 1 according to the present invention, e is an integer from 0 to 5. Here, when e is 0, it means that hydrogen is non-substituted with the substituent R1. On the other hand, when e is an integer from 1 to 5, it means that hydrogen is substituted with the substituent R1, and in this case, multiple R1s are the same or different from each other.

[0136] R1 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 40Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, and specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It can be selected from the group consisting of arylamine groups.

[0137] For example, R1 can 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.

[0138] In the chemical formula 1 according to the present invention, Moiety When bonded in the ortho-position to the moiety, b is an integer from 0 to 3, Ar2 is a phenylene group or a naphthalene group, and Ar3 is a phenyl group or a naphthyl group. However, among one or more Ar2, the Ar2 closest to the ring Cy1-condensed benzene ring is selected from the group consisting of a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group, and a 2,4-naphthalene group having a meta- or para-bond.

[0139] one side, Moiety When bonded to the moiety in the meta- or para-position, b is an integer of 1 to 3, Ar2 is a phenylene group or a naphthalene group, and Ar3 is a phenyl group or a naphthyl group. However, at least one of the one or more Ar2 is selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group, and a 2,3-naphthalene group having an ortho-bond.

[0140] In chemical formula 1 according to the present invention, c is 0 or 1, d is an integer from 0 to 2, provided that 0≤ b+d≤ 3,

[0141] Moiety is Moiety or It is bonded in the ortho-position to the moiety, Ar4 is a phenylene group or a naphthalene group, and Ar5 is a phenyl group or a naphthyl group.

[0142] According to these b, c, d, Ar2, Ar3, Ar4 and A5, The moiety may be a moiety represented by any one of the following chemical formulae B1 to B3, but is not limited thereto.

[0143] [Chemical Formula B1]

[0144]

[0145] [Chemical Formula B2]

[0146]

[0147] [Chemical Formula B3]

[0148]

[0149] In the above chemical formulas B1 to B3,

[0150] * indicates the part that is combined with chemical formula 1.

[0151] Rings Cy1, e, and R1 are each as defined in the above chemical formula 1,

[0152] When rings Cy2 to Cy5 are each present or absent, and when rings Cy2 to Cy5 are each present, rings Cy2 to Cy5 are each a 6-membered condensed aromatic ring;

[0153] The plurality of h are each an integer from 0 to 6, specifically, each can be an integer from 0 to 3, and more specifically, each can be 0 or 1,

[0154] Multiple R are the same or different, 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 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, and specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It can be selected from the group consisting of arylamine groups, and more specifically, it can 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.

[0155] As mentioned above Moieties and Depending on the moiety, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 19, but is not limited thereto.

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] In the above chemical formulas 2 to 19,

[0175] EWG, L1, L2, ring Cy1, e and R1 are each as defined in the above chemical formula 1,

[0176] Rings Q1 to Q3 are each present or non-existent, and when rings Q1 to Q3 are each present, rings Q1 to Q3 are each a 6-membered condensed aromatic ring,

[0177] f and g are 0 or 1, respectively,

[0178] Ar6 and Ar7 are the same or different, and each independently represents a phenylene group or a naphthalene group,

[0179] Rings Cy2 to Cy5 are each present or absent, and when rings Cy2 to Cy5 are each present, rings Cy2 to Cy5 are each a 6-membered condensed aromatic ring;

[0180] The plurality of h are each integers from 0 to 6,

[0181] Multiple R are the same or different, 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 40Alkyl 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, and specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It can be selected from the group consisting of arylamine groups,

[0182] The phenylene group and naphthalene group of the above Ar6 and Ar7 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~C40 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, specifically deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 12 Alkyl group of C6~C 18 Aryl group, heteroaryl group having 5 to 18 nuclear atoms and C6~C 18 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0183] For example, in the above chemical formulae 2, 3, 8, 9, 14 and 15, L1 may be bonded to an adjacent ring Q1-fused aromatic ring in a meta- or para-position with respect to the ring Q2-fused aromatic ring.

[0184] As another example, in the chemical formulae 2 to 7, L2 may be a single bond or a divalent linker group having a meta- or para-bond, such as a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group, or a 2,4-naphthalene group.

[0185] As another example, in the above chemical formulae 8 to 13, L2 may be bonded to an adjacent ring Cy1-fused aromatic ring in the meta- or para-position to the ring Cy2-fused aromatic ring or the ring Cy3-fused aromatic ring.

[0186] The compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 20 to 37, but is not limited thereto.

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] In the above chemical formulas 20 to 37,

[0206] L1, L2, ring Cy1, e and R1 are each as defined in the above chemical formula 1,

[0207] Rings Q1 to Q3, f, g, Ar6, Ar 7,Rings Cy2 to Cy5, h, and R are each as defined in the above chemical formulas 2 to 19,

[0208] X1 to X3 are the same or different from each other, and are each independently N or C(R8), provided that at least one of X1 to X3 is N, and specifically, two to three of X1 to X3 may be N;

[0209] R2 and R3 are the same or different, and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups.

[0210] For example, in the above chemical formulae 20, 21, 26, 27, 32 and 33, L1 may be a single bond or may be bonded to an adjacent ring Q1-fused aromatic ring in a meta- or para-position with respect to the ring Q2-fused aromatic ring.

[0211] As another example, in the chemical formulas 20 to 25, L2 may be a single bond or a divalent linker group having a meta- or para-bond, such as a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group, or a 2,4-naphthalene group.

[0212] As another example, in the above chemical formulae 26 to 31, L2 may be bonded to a single bond or to an adjacent ring Cy1-fused aromatic ring in the meta- or para-position to a ring Cy2-fused aromatic ring or a ring Cy3-fused aromatic ring.

[0213] The compound represented by the above-mentioned chemical formula 1 can be further specified as compounds 1 to 207 below, but is not limited thereto.

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] 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.

[0224] 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.

[0225] 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.

[0226] 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.

[0227] 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.

[0228] 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.

[0229] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0230] 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.

[0231] 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.

[0232] 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.

[0233] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240]

[0241] Organic electroluminescent devices

[0242] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0243] 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.

[0244] 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).

[0245] 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.

[0246] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0247] In the present invention, the electron transport layer material that can be mixed with the compound of the above chemical formula 1 may be an electron transport material or n-type dopant commonly known in the art. Non-limiting examples of the electron transport material that can be used in the present invention include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, and aluminum complexes (e.g., Alq). 3,tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more. Examples of n-type dopants usable in the present invention may be metals (e.g., alkali metals or alkaline earth metals) or complexes of the above metals, and specifically, may be LiQ (Lithium Quinolate), etc.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] 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).

[0254] 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.

[0255] 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.

[0256] 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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260]

[0261] 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.

[0262] [Synthesis Example 1] Synthesis of Compound 1

[0263]

[0264] [Synthesis Example 1-1] Synthesis of SC-1

[0265] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 25.8 mmol), (3'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (6.0 g, 25.8 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.5 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-1 (7.7 g, yield 60%).

[0266] 1H-NMR: δ 8.36(d, 4H), 7.90~7.60(m, 6H), 7.55(t, 4H), 7.50~7.45(m, 8H), 7.96(d, 1H)

[0267] Mass: [(M+H) + ] : 497

[0268] [Synthesis Example 1-2] Synthesis of Compound 1

[0269] Compound SC-1 (5.0 g, 10.1 mmol), [1,1'-biphenyl]-2-ylboronic acid (2.0 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) synthesized in Synthesis Example 1-1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 1 (2.7 g, yield 43%).

[0270] Mass: [(M+H) + ] : 615

[0271]

[0272] [Synthesis Example 2] Synthesis of Compound 2

[0273]

[0274] [Synthesis Example 2-1] Synthesis of SC-2

[0275] 4-([1,1'-biphenyl]-3-yl)-6-(3-bromophenyl)-2-phenylpyrimidine (10.0 g, 21.6 mmol), (3'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (5.0 g, 21.6 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), and K2CO3 (6.0 g, 43.2 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-2 (7.2 g, yield 58%).

[0276] 1H-NMR: δ 8.36 (d, 2H), 8.28 (s, 1H), 7.96 - 7.94 (m, 7H), 7.73 - 7.71 (m, 4H), 7.62 - 7.59 (m, 4H), 7.55 - 7.40 (m, 9H)

[0277] Mass: [(M+H) + ] : 572

[0278] [Synthesis Example 2-2] Synthesis of Compound 2

[0279] Compound SC-2 (5.0 g, 8.8 mmol), [1,1'-biphenyl]-2-ylboronic acid (1.7 g, 8.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized in Synthesis Example 2-1 were added to 80 ml of Dioxane and 20 ml of H2O, and stirred under reflux while heating for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 2 (2.8 g, yield 46%).

[0280] Mass: [(M+H) + ] : 690

[0281]

[0282] [Synthesis Example 3] Synthesis of Compound 23

[0283]

[0284] Compound SC-1 (5.0 g, 10.1 mmol), [1,1'-biphenyl]-2-ylboronic acid (2.8 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) synthesized in Synthesis Example 1-1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 23 (3.0 g, yield 44%).

[0285] Mass: [(M+H) + ] : 682

[0286]

[0287] [Synthesis Example 4] Synthesis of Compound 26

[0288]

[0289] [Synthesis Example 4-1] Synthesis of SC-3

[0290] 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10.0 g, 27.9 mmol), (3''-chloro-[1,1':2',1''-terphenyl]-3-yl)boronic acid (8.6 g, 27.9 mmol), Pd(PPh3)4 (1.0 g, 0.8 mmol), and K2CO3 (7.7 g, 55.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain SC-3 (10.3 g, yield 63%).

[0291] 1H-NMR: δ 8.36(d, 3H), 8.03~7.94(m, 6H), 7.82~7.73(m, 3H), 7.60~7.31(m, 12H)

[0292] Mass: [(M+H) + ] : 587

[0293] [Synthesis Example 4-2] Synthesis of Compound 26

[0294] Compound SC-3 (5.0 g, 8.5 mmol) synthesized in Synthesis Example 4-1, [1,1':2',1''-terphenyl]-4-ylboronic acid (2.3 g, 8.5 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.2 g, 0.5 mmol), Cs2CO3 (5.6 g, 17.1 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 26 (3.0 g, yield 45%).

[0295] Mass: [(M+H) + ] : 781

[0296]

[0297] [Synthesis Example 5] Synthesis of Compound 54

[0298]

[0299] [Synthesis Example 5-1] Synthesis of SC-4

[0300] 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 25.8 mmol), (3''-chloro-[1,1':2',1''-terphenyl]-3-yl)boronic acid (7.9 g, 25.8 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.5 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-4 (9.0 g, yield 61%).

[0301] 1H-NMR: δ 8.36(d, 4H), 7.97~7.94(m, 6H), 7.73(t, 1H), 7.60(m, 3H), 7.50~7.48(m, 8H), 7.61(d, 1H), 7.27(d, 2H)

[0302] Mass: [(M+H) + ] : 573

[0303] [Synthesis Example 5-2] Synthesis of Compound 54

[0304] Compound SC-4 (5.0 g, 8.7 mmol) synthesized in Synthetic Example 5-1, [1,1':2',1''-terphenyl]-3'-ylboronic acid (2.4 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), Cs2CO3 (5.7 g, 17.5 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 54 (3.2 g, yield 48%).

[0305] Mass: [(M+H) + ] : 767

[0306]

[0307] [Synthesis Example 6] Synthesis of Compound 71

[0308]

[0309] [Synthesis Example 6-1] Synthesis of SC-5

[0310] 2-(4-bromo-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 21.6 mmol), (3'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (5.0 g, 21.6 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), and K2CO3 (6.0 g, 43.1 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-5 (7.8 g, yield 63%).

[0311] 1H-NMR: δ 8.36(d, 4H), 8.15~8.13(m, 2H), 7.97~7.96(m, 3H), 7.79(d, 2H), 7.60(t, 2H), 7.50~7.40(m, 12H)

[0312] Mass: [(M+H) + ] :573

[0313] [Synthesis Example 6-2] Synthesis of Compound 71

[0314] Compound SC-5 (5.0 g, 8.7 mmol), [1,1'-biphenyl]-2-ylboronic acid (1.7 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized in Synthesis Example 6-1 were added to 80 ml of Dioxane and 20 ml of H2O, and stirred under reflux while heating for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 71 (2.7 g, yield 45%).

[0315] Mass: [(M+H) + ] : 691

[0316]

[0317] [Synthesis Example 7] Synthesis of Compound 75

[0318]

[0319] [Synthesis Example 7-1] Synthesis of SC-6

[0320] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 25.8 mmol), (2-(4-chloronaphthalen-1-yl)phenyl)boronic acid (7.3 g, 25.8 mmol), Pd(PPh3)4 (0.9 g, 0.8 mmol), and K2CO3 (7.1 g, 51.5 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain SC-6 (8.3 g, yield 59%).

[0321] 1H-NMR: δ 8.93(d, 1H), 8.36(d, 4H), 8.31(d, 1H), 7.96(d, 4H), 7.55~7.40(m, 12H), 7.25(d, 2H)

[0322] Mass: [(M+H) + ] : 547

[0323] [Synthesis Example 7-2] Synthesis of Compound 75

[0324] Compound SC-6 (5.0 g, 9.2 mmol), [1,1'-biphenyl]-2-ylboronic acid (1.8 g, 9.2 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized in Synthetic Example 7-1 were added to 80 ml of Dioxane and 20 ml of H2O, and stirred under reflux while heating for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 75 (2.9 g, yield 47%).

[0325] Mass: [(M+H) + ] : 665

[0326]

[0327] [Synthesis Example 8] Synthesis of Compound 98

[0328]

[0329] Compound SC-1 (5.0 g, 10.1 mmol) synthesized in Synthetic Example 1-1, (3'-phenyl-[1,1':2',1''-terphenyl]-3-yl)boronic acid (3.5 g, 10.1 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), Cs2CO3 (5.7 g, 17.5 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 98 (3.6 g, yield 46%).

[0330] Mass: [(M+H) + ] : 767

[0331]

[0332] [Synthesis Example 9] Synthesis of Compound 122

[0333]

[0334] [Synthesis Example 9-1] Synthesis of SC-7

[0335] 2-(3-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 22.8 mmol), (3''-chloro-[1,1':2',1''-terphenyl]-4-yl)boronic acid (7.0 g, 22.8 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (6.3 g, 45.7 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-7 (8.8 g, yield 62%).

[0336] 1H-NMR: δ 9.03(d, 1H), 8.36(d, 4H), 8.14~8.13(m, 2H), 7.97~7.96(m, 3H), 7.82(s, 1H), 7.60~7.48(m, 12H), 7.39(d, 1H), 7.25(d, 4H)

[0337] Mass: [(M+H) + ] : 623

[0338] [Synthesis Example 9-2] Synthesis of Compound 122

[0339] Compound SC-7 (5.0 g, 8.0 mmol) synthesized in Synthetic Example 9-1, [1,1':2',1''-terphenyl]-3'-ylboronic acid (2.2 g, 8.0 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), Cs2CO3 (5.7 g, 17.5 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 122 (3.2 g, yield 48%).

[0340] Mass: [(M+H) + ] : 817

[0341]

[0342] [Synthesis Example 10] Synthesis of Compound 129

[0343]

[0344] Compound SC-4 (5.0 g, 8.7 mmol), (3,4-diphenylnaphthalen-1-yl)boronic acid (2.8 g, 8.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.5 mmol), and Cs2CO3 (5.7 g, 17.5 mmol) synthesized in Synthesis Example 5-1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 129 (3.6 g, yield 51%).

[0345] Mass: [(M+H) + ] : 817

[0346]

[0347] [Synthesis Example 11] Synthesis of Compound 144

[0348]

[0349] [Synthesis Example 11-1] Synthesis of SC-8

[0350] 4-(4-bromophenyl)-2-phenylbenzofuro[3,2-d]pyrimidine (10.0 g, 24.9 mmol), (4'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (5.8 g, 24.9 mmol), Pd(PPh3)4 (0.9 g, 0.7 mmol), and K2CO3 (6.9 g, 49.9 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-8 (7.6 g, yield 60%).

[0351] 1H-NMR: δ 8.35~8.30(m, 4H), 7.96(d, 2H), 7.62~7.50(m, 11H), 7.36(t, 1H), 7.25~7.22(m, 3H)

[0352] Mass: [(M+H) + ] : 510

[0353] [Synthesis Example 11-2] Synthesis of Compound 144

[0354] Compound SC-8 (5.0 g, 9.8 mmol), [1,1'-biphenyl]-2-ylboronic acid (1.9 g, 9.8 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.4 g, 19.6 mmol) synthesized in Synthetic Example 11-1 were added to 80 ml of Dioxane and 20 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 144 (3.1 g, yield 50%).

[0355] Mass: [(M+H) + ] : 628

[0356]

[0357] [Synthesis Example 12] Synthesis of Compound 163

[0358]

[0359] [Synthesis Example 12-1] Synthesis of SC-9

[0360] 4-(3-bromophenyl)-2-phenylquinazoline (10.0 g, 27.7 mmol), (3'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (6.4 g, 27.7 mmol), Pd(PPh3)4 (1.0 g, 0.8 mmol), and K2CO3 (7.7 g, 55.4 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-9 (7.7 g, yield 59%).

[0361] 1H-NMR: δ 8.35 (d, 2H), 8.13 (d, 1H), 7.96 - 7.90 (m, 5H), 7.83 - 7.81 (m, 2H), 7.60 - 7.48 (m, 10H)

[0362] Mass: [(M+H) + ] : 470

[0363] [Synthesis Example 12-2] Synthesis of Compound 163

[0364] Compound SC-9 (5.0 g, 10.7 mmol) synthesized in Synthetic Example 12-1, [1,1':2',1''-terphenyl]-3-ylboronic acid (2.9 g, 10.7 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), Cs2CO3 (6.9 g, 21.3 mmol) were added to 80 ml of dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 163 (3.5 g, yield 49%).

[0365] Mass: [(M+H) + ] : 664

[0366]

[0367] [Synthesis Example 13] Synthesis of Compound 173

[0368]

[0369] [Synthesis Example 13-1] Synthesis of SC-10

[0370] 4-(4-bromophenyl)-2-phenylbenzo[4,5]thieno[2,3-d]pyrimidine (10.0 g, 24.0 mmol), (4'-chloro-[1,1'-biphenyl]-2-yl)boronic acid (5.6 g, 24.0 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and K2CO3 (6.6 g, 48.0 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-10 (7.7 g, yield 61%).

[0371] 1H-NMR: δ 8.45(d, 1H), 8.36(d, 2H), 8.30(d, 2H), 7.96~7.93(m, 3H), 7.78(d, 2H), 7.62~7.49(m, 9H), 7.25(d, 2H)

[0372] Mass: [(M+H) + ] : 526

[0373] [Synthesis Example 13-2] Synthesis of Compound 173

[0374] Compound SC-10 (5.0 g, 9.5 mmol), [1,1':2',1''-terphenyl]-3-ylboronic acid (2.6 g, 9.5 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.2 g, 19.0 mmol) synthesized in Synthetic Example 13-1 were added to 80 ml of Dioxane and 20 ml of H2O, and stirred under reflux while heating for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 173 (3.4 g, yield 50%).

[0375] Mass: [(M+H)+ ] : 720

[0376]

[0377] [Synthesis Example 14] Synthesis of Compound 191

[0378]

[0379] [Synthesis Example 14-1] Synthesis of SC-11

[0380] 2-(3-bromophenyl)-4-phenylquinazoline (10.0 g, 27.7 mmol), (3''-chloro-[1,1':2',1''-terphenyl]-4-yl)boronic acid (8.5 g, 27.7 mmol), Pd(PPh3)4 (1.0 g, 0.8 mmol), and K2CO3 (7.7 g, 55.4 mmol) were added to 160 ml of dioxane and 40 ml of H2O, and the mixture was heated and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound SC-11 (9.1 g, yield 60%).

[0381] 1H-NMR: δ 8.38(d, 1H), 8.13(d, 1H), 7.96~7.94(m, 4H), 7.80~7.48(m, 15H), 7.25(d, 4H)

[0382] Mass: [(M+H) + ] : 546

[0383] [Synthesis Example 14-2] Synthesis of Compound 191

[0384] Compound SC-11 (5.0 g, 9.2 mmol), [1,1':2',1''-terphenyl]-3'-ylboronic acid (2.5 g, 9.2 mmol), Pd(OAc)2 (0.1 g, 0.3 mmol), XPhos (0.3 g, 0.6 mmol), and Cs2CO3 (6.0 g, 18.3 mmol) synthesized in Synthetic Example 14-1 were added to 80 ml of Dioxane and 20 ml of H2O, and stirred under reflux for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the resulting solid was filtered to remove the solution and dried in an oven. The dried solid was purified by column chromatography to obtain compound 191 (3.2 g, yield 47%).

[0385] Mass: [(M+H) + ] : 740

[0386]

[0387] [Example 1] Fabrication of a blue organic electroluminescent device

[0388] After the compound 1 synthesized in the above Synthesis Example 1 was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the following process.

[0389] 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.

[0390] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / Compound 1 + Liq (1:1)(30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, and Liq used are as follows, respectively.

[0391]

[0392]

[0393] [Examples 2 to 14] Preparation of blue organic electroluminescent devices

[0394] 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 1 used as an electron transport layer material in Example 1.

[0395]

[0396] [Comparative Examples 1 to 4] Manufacturing of blue organic electroluminescent devices

[0397] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq3, compounds CC-1, CC-2, and CC-3 were used instead of compound 1 used as an electron transport layer material in Example 1. At this time, the structures of Alq3, compounds CC-1, CC-2, and CC-3 used are as follows, respectively.

[0398]

[0399]

[0400] [Evaluation Example 1]

[0401] For the organic electroluminescent devices manufactured in Examples 1 to 14 and Comparative Examples 1 to 4, 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.

[0402] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 13.34557.0 Example 2 Compound 23.44547.0 Example 3 Compound 233.24557.1 Example 4 Compound 263.24547.2 Example 5 Compound 543.34547.1 Example 6 Compound 713.24547.2 Example 7 Compound 753.24537.1 Example 8 Compound 983.34557.0 Example 9 Compound 1223.44547.1 Example 10 Compound 1293.24547.0 Example 11 Compound 1443.34557.0 Example 12 Compound 1633.14547.2 Example 13 Compound 1733.34547.1 Example 14 Compound 1913.14557.0 Comparative Example 1 Alq 34.64575.3 Comparative Example 2 CC-13.94596.1 Comparative Example 3 CC-23.84556.2 Comparative Example 4 CC-33.84556.0

[0403] From the above Table 1, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 14 had superior driving voltage, emission peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 1 to 4.

[0404]

[0405] [Example 15] Fabrication of a blue organic electroluminescent device

[0406] Compound 1 synthesized in the above Synthesis Example 1 was purified by high purity sublimation using a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following process.

[0407] 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.

[0408] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / Compound 1 (5 nm) / ET + Liq (1:1)(30 nm) / LiF (1 nm) / Al (100 nm) in that order. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used are as follows.

[0409]

[0410]

[0411]

[0412] [Examples 16 to 28] Preparation of blue organic electroluminescent devices

[0413] A blue organic electroluminescent device was manufactured in the same manner as in Example 15, except that each of the compounds described in Table 2 below was used instead of Compound 1 used as an electron transport auxiliary layer material in Example 15.

[0414]

[0415] [Comparative Example 5]

[0416] A blue organic electroluminescent device was manufactured in the same manner as in Example 15, except that compound 1, which was used as an electron transport auxiliary layer material in Example 15, was not used.

[0417]

[0418] [Comparative Examples 6 to 8] Manufacturing of blue organic electroluminescent devices

[0419] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that CC-1, CC-2, and CC-3 were used instead of Compound 1 used as an electron transport auxiliary layer material in Example 15. The structures of CC-1, CC-2, and CC-3 used here are as follows, respectively.

[0420]

[0421]

[0422] [Evaluation Example 2]

[0423] For the organic electroluminescent devices manufactured in Examples 15 to 28 and Comparative Examples 5 to 8, 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.

[0424] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 15 Compound 13.14547.3 Example 16 Compound 23.04557.2 Example 17 Compound 233.14557.3 Example 18 Compound 263.14557.3 Example 19 Compound 543.04547.4 Example 20 Compound 713.24557.2 Example 21 Compound 753.14547.1 Example 22 Compound 983.14547.2 Example 23 Compound 1223.24557.2 Example 24 Compound 1293.14557.1 Example Compound 25 1443.0 4547.3 Example 26 Compound 16 33.1 4547.2 Example 27 Compound 17 33.2 4557.1 Example 28 Compound 19 13.3 4547.3 Comparative Example 5-4.6 4566.0 Comparative Example 6 CC-13.8 4556.3 Comparative Example 7 CC-23.9 4566.3 Comparative Example 8 CC-33.7 4566.3

[0425] From Table 2 above, it was confirmed that the organic light-emitting devices manufactured in Examples 15 to 28 had superior driving voltage, luminescence peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Examples 5 to 8.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] (In the above chemical formula 1, EWG stands for electron withdrawing group; L 1 and L 2 are identical or different from each other, and each independently represents a single bond, or C 6 ~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 3 to 18 nuclear atoms; a is an integer between 3 and 5, Multiple Ar 1 are identical or different from each other, and each independently represents a phenylene group or a naphthalene group, Just multiple Ar 1 At most two of them are selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group and a 2,3-naphthalene group having ortho-linkages, wherein the ortho-linkages are discontinuous; Ring Cy1 is present or absent, and when ring Cy1 is present, ring Cy1 is a six-membered fused aromatic ring; Moiety When bonded ortho-position to a moiety, b is an integer from 0 to 3, and Ar 2 is a phenylene group or a naphthalene group, and Ar 3 is a phenyl group or a naphthyl group, and only 1 or more Ar 2 Ar, which is closest to the Cy1-condensed benzene ring in the middle ring 2 is selected from the group consisting of a 1,3-phenylene group, a 1,4-phenylene group, a 1,3-naphthalene group, a 1,4-naphthalene group and a 2,4-naphthalene group having a meta- or para-bond; Moiety When bonded to a moiety in the meta- or para-position, b is an integer from 1 to 3, and Ar 2 is a phenylene group or a naphthalene group, and Ar 3 is a phenyl group or a naphthyl group, and only 1 or more Ar 2 At least one of them is selected from the group consisting of a 1,2-phenylene group, a 1,2-naphthalene group and a 2,3-naphthalene group having an ortho-bond; c is 0 or 1, d is an integer from 0 to 2, However, 0≤ b+d ≤ 3; Moiety is Moiety or Ortho-position bonded to the moiety, Ar 4 is a phenylene group or a naphthalene group, and Ar 5 is a phenyl group or a naphthyl group; e is an integer from 0 to 5, R 1 Silver hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, 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 is selected from the group consisting of arylamine groups, Above L 1 and L 2 Arylene group and heteroarylene group of Ar, 1 , Ar 2 and Ar 4 Phenylene and naphthalene groups, Ar 3 and Ar 5 The phenyl or naphthyl group of each is 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 above EWG is a compound selected from the group consisting of the following substituents EWG1 to EWG10: (In the above substitutes EWG1 to EWG10, X 1 Inland X 3 are identical or different from each other, and each independently represents N or C(R 8 ) and only X 1 Inland X 3 At least one of them is N, Y 1 is O or S, X 4 and X 5 are identical or different from each other, and each independently represents N or C(R 9 ) and only X 4 and X 5 At least one of them is N, X 6 and X 7 are identical or different from each other, and each independently represents N or C(R 10 ) and only X 6 and X 7 At least one of them is N, R 2 Inland R 10 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).

3. In paragraph 1, Above The moiety is a compound represented by the following chemical formula A: [Chemical Formula A] (In the above chemical formula A, Rings Q1 to Q3 are each present or non-existent, and when rings Q1 to Q3 are each present, rings Q1 to Q3 are each a 6-membered condensed aromatic ring, The moiety binds at the meta- or para-position, f and g are 0 or 1, respectively, Ar 6 and Ar 7 are identical or different from each other, and each independently represents a phenylene group or a naphthalene group, The plural h are each integers from 0 to 6, Multiple R's are the same or different and each independently represents 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 is selected from the group consisting of arylamine groups, Above Ar 6 and Ar 7 The phenylene group and naphthalene group 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).

4. In paragraph 3, A compound in which the moiety represented by the above chemical formula A is a moiety represented by any one of the following chemical formulas A1 to A5: [Chemical Formula A1] [Chemical Formula A2] [Chemical Formula A3] [Chemical Formula A4] [Chemical Formula A5] (In the above chemical formulas A1 to A5, Rings Q1 to Q5 are each present or non-existent, and when rings Q1 to Q5 are each present, rings Q1 to Q5 are each a 6-membered condensed aromatic ring, The plural h are each integers from 0 to 6, Multiple R's are the same or different and each independently represents 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).

5. In paragraph 1, Above A compound, wherein the moiety is a moiety represented by any one of the following chemical formulae B1 to B3: [Chemical Formula B1] [Chemical formula B2] [Chemical formula B3] (In the above chemical formulas B1 to B3, Ring Cy1, e, R 1 are as defined in Article 1, respectively, Rings Cy2 to Cy5 are present or absent, and when each of rings Cy2 to Cy5 is present, each of rings Cy2 to Cy5 is a 6-membered condensed aromatic ring, The plural h are each integers from 0 to 6, Multiple R's are the same or different and each independently represents 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).

6. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 2 to 19: [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] (In the above chemical formulas 2 to 19, EWG, L 1 , L 2 , ring Cy1, e and R 1 are as defined in Article 1, respectively, Rings Q1 to Q3 are each present or non-existent, and when rings Q1 to Q3 are each present, rings Q1 to Q3 are each a 6-membered condensed aromatic ring, f and g are 0 or 1, respectively, Ar 6 and Ar 7 are identical or different from each other, and each independently represents a phenylene group or a naphthalene group, Rings Cy2 to Cy5 are each present or absent, and when rings Cy2 to Cy5 are each present, rings Cy2 to Cy5 are each a 6-membered fused aromatic ring; The plural h are each integers from 0 to 6, Multiple R's are the same or different and each independently represents 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 is selected from the group consisting of arylamine groups, Above Ar 6 and Ar 7 The phenylene group and naphthalene group 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).

7. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 20 to 37: [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] [Chemical formula 30] [Chemical Formula 31] [Chemical formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical formula 36] [Chemical Formula 37] (In the above chemical formulas 20 to 37, L 1 , L 2 , ring Cy1, e and R 1 are as defined in Article 1, respectively, X 1 Inland X 3 are identical or different from each other, and each independently represents N or C(R 8 ) and only X 1 Inland X 3 At least one of them is N, R 2 and R 3 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 is selected from the group consisting of arylamine groups, Rings Q1 to Q3 are each present or non-existent, and when rings Q1 to Q3 are each present, rings Q1 to Q3 are each a 6-membered condensed aromatic ring, f and g are 0 or 1, respectively, Ar 6 and Ar 7 are identical or different from each other, and each independently represents a phenylene group or a naphthalene group, Rings Cy2 to Cy5 are each present or non-existent, and when rings Cy2 to Cy5 are each present, rings Cy2 to Cy5 are each a 6-membered condensed aromatic ring, The plural h are each integers from 0 to 6, Multiple R's are the same or different and each independently represents 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 is selected from the group consisting of arylamine groups, Above Ar 6 and Ar 7 The phenylene group and naphthalene group 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).

8. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 207 below: .

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

10. In paragraph 9, 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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