Organic light-emitting compound and organic electroluminescent element using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport capability, light-emitting performance and thermal stability; and an organic electroluminescent element comprising the novel compound in one or more organic layers and thus having enhanced luminous efficiency, driving voltage and lifespan.

Description

Organic light-emitting compounds and organic electroluminescent devices using the same

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more specifically, to a compound having excellent electron transport capability and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

[0002]

[0003] In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0005] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0006] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0007] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0008] [Prior Art Literature]

[0009] [Patent Literature]

[0010] Republic of Korea Published Patent No. 10-2024-0056433

[0011]

[0012] The present invention aims to provide a novel compound that has excellent heat resistance, carrier transport capacity, luminescence capacity, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, a lifespan improvement layer material, a light-emitting auxiliary layer material, or an electron transport layer material.

[0013] In addition, the present invention also aims to provide an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and an improved lifespan.

[0014]

[0015] To achieve the above objective, the present invention provides a compound represented by the following chemical formula 1.

[0016] [Chemical Formula 1]

[0017]

[0018] In the above chemical formula 1,

[0019] Z are identical or different from each other, each independently CR2 or N, provided that at least one of the plurality of Zs is N,

[0020] Ar1 and Ar2 are identical or different from each other, and each independently C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei,

[0021] L is a single bond, or an alkylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, or C6 to C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei,

[0022] n is an integer from 0 to 3, and

[0023] X is a moiety selected from the group of substituents represented by the following structural formula, and

[0024]

[0025] In the above formula,

[0026] * indicates the part connected to the above chemical formula 1, and

[0027] R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei;

[0028] m is an integer from 0 to 5, and

[0029] The alkylene group, cycloalkylene group, arylene group, and heteroarylene group of L; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of Ar1~Ar2 and R1~R2 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0030] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0031] Here, the organic layer comprising the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0032]

[0033] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0034] In particular, when a compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional electron transport materials.

[0035] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0036] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0037]

[0038] The present invention will be described in detail below.

[0039] <New Organic Compounds>

[0040] The present invention provides a novel compound that exhibits excellent electron transport capacity, luminescence capacity, and thermal stability, thereby enabling the device to demonstrate low voltage, high luminescence efficiency, and long lifespan characteristics.

[0041] According to the present invention, the compound represented by Formula 1 essentially comprises a nitrogen-containing heteroaromatic ring (e.g., azine, Z-containing ring) having an electron withdrawing group (EWG) and a naphthalene moiety connected by two phenyl groups, and has a basic skeletal structure in which they are directly connected or connected through a separate linker (e.g., L).

[0042] Specifically, the compound of Chemical Formula 1 above can control the steric hindrance in the molecular structure of organic materials by utilizing two phenyl groups bonded to naphthalene.

[0043] In other words, to be used as a material for an electron transport layer or an electron transport auxiliary layer of an OLED, a wide bandgap and a low LUMO value suitable for it are required. In the present invention, two bonding positions suitable for such a structure have been discovered, and the LUMO value suitable for the electron transport layer or electron transport auxiliary layer can be controlled by inducing delocalization of LUMO orbitals, and the triplet energy (T1) can be increased through maximized steric hindrance, and excitons can be gathered toward the host side, and device efficiency and lifespan can be increased through exciton blocking. For example, a naphthalene moiety with two phenyl groups bonded can have the following four structures, and different steric hindrances can be exhibited depending on these structures.

[0044]

[0045] As mentioned above, if steric hindrance is too strong, the stress applied to the molecular structure of the organic material increases, which can lead to structural collapse; conversely, if steric hindrance is too weak, steric bonds do not form in the molecular structure, resulting in a degradation of properties.

[0046] In addition, introducing an additional aryl group (e.g., phenyl group) to the end of the naphthalene moiety adds an electron-donating unit, which serves to increase the stability of the bonded EWG. Consequently, electron-donating is enhanced, which can further increase the stability of the molecule.

[0047] As described above, when the compound represented by Formula 1 of the present invention is applied as an organic layer material, preferably a light-emitting layer material (a blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a light-emitting auxiliary layer material, or a lifespan improvement layer material of an organic electroluminescent device, the performance and lifespan characteristics of the organic electroluminescent device can be improved. In particular, when the compound of the present invention is utilized as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect can be expected in terms of the efficiency, driving voltage, and lifespan characteristics of the device. Consequently, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0048] According to the present invention, the compound represented by Formula 1 has a basic skeletal structure in which a nitrogen-containing heteroaromatic ring (e.g., azine, Z-containing ring) with excellent electron transport capacity and EWG characteristics is directly connected to a naphthalene moiety in which two phenyl groups are connected, or connected through a separate linker (e.g., L).

[0049] The above nitrogen-containing heterocyclic ring (e.g., Z-containing ring) is a monocyclic nitrogen-containing heteroaryl group containing at least one nitrogen atom. In one example of a nitrogen-containing heteroaromatic ring, Z may be identical or different from each other, and each may independently be CR2 or N, provided that at least one of the plurality of Zs contains N. Preferably, it contains 2 to 3 Ns. By including a heterocyclic ring containing 2 to 3 nitrogens in this way, superior electron absorption characteristics are exhibited, which is advantageous for electron injection and transport.

[0050] Here, R2 are identical or different and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple R2s, the multiple R2s may be identical or different from each other. Specifically, R2 is hydrogen, deuterium (D), C1~C 40 alkyl group of, C6~C 60 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0051] For example, a nitrogen-containing heterocyclic ring (e.g., a Z-containing ring) may be further specified by any one selected from the following structural formulas. However, it is not limited thereto.

[0052]

[0053] In the above formula,

[0054] * indicates the part connected to the above chemical formula 1, and

[0055] Ar1, Ar2, and R2 are each as defined in Chemical Formula 1.

[0056] In the above nitrogen-containing heterocyclic ring (e.g., Z-containing ring), Ar1 and Ar2 may be substituted as various substituents. Ar1 and Ar2 may be identical or different from each other, and each independently C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. Specifically, Ar1 is C6~C 60 It is an aryl group, and Ar2 is C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. More specifically, Ar1 is C6~C 60 It is an aryl group, and Ar2 is C6~C 40 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclei.

[0057] For example, Ar1 may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0058]

[0059] In the above formula,

[0060] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R2 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0061] To give another specific example, Ar2 may be identical to or different from the aforementioned Ar1, and may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0062]

[0063]

[0064] In the above formula,

[0065] * indicates the part connected to the above chemical formula 1, and

[0066] R 11 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In addition, at least one substituent known in the art (e.g., identical to the R2 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0067] In the compound represented by Formula 1 according to the present invention, the other side of the nitrogen-containing heteroaromatic ring (e.g., azine, Z-containing ring) comprises a naphthalene moiety with two phenyl groups attached.

[0068] For example, the naphthalene moiety may be embodied as a specific structure for inducing a predetermined steric hindrance in the molecular structure, and may be embodied as any one selected from the following structural formulas. However, it is not limited thereto.

[0069]

[0070] In the above formula,

[0071] * indicates the part connected to the above chemical formula 1, and

[0072] R1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. If there are multiple R1s, the multiple R1s may be identical or different from each other. Specifically, R1 is deuterium (D), C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, more specifically C6~C 40 It is preferable to select from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclei.

[0073] m is an integer from 0 to 5, more specifically an integer from 0 to 3. Here, when m is 0, R1 is hydrogen, and when m is 1 to 5, R1 may have the aforementioned substituents excluding hydrogen. In this case, to achieve the effect of improving molecular stability by adding an electron-donating unit to the naphthalene moiety, it is preferable to introduce one aryl group (e.g., a phenyl group) as R1.

[0074] For example, a compound of Formula 1 into which a naphthalene moiety is introduced can be represented by Formula 2 or Formula 3 below.

[0075] [Chemical Formula 2]

[0076]

[0077] [Chemical Formula 3]

[0078]

[0079] In the above formula,

[0080] Z, Ar1, Ar2, L, R1, m, and n are each defined in Chemical Formula 1.

[0081] In the compound represented by Formula 1 according to the present invention, a nitrogen-containing heteroaromatic ring (e.g., azine, Z-containing ring) and a naphthalene moiety to which two phenyl groups are bonded may be directly bonded or bonded through a separate linker (L). When a separate linker (L) exists between the nitrogen-containing heteroaromatic ring and the naphthalene moiety in this way, the HOMO region is expanded to provide an advantage in the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate overlap of HOMO-LUMO. In addition, by controlling the bonding position between the naphthalene moiety and the linker, additional steric hindrance of the molecular structure can be generated, thereby inducing delocalization of LUMO orbitals and allowing for the control of LUMO values ​​suitable for an electron transport layer or an electron transport auxiliary layer.

[0082] Such linkers (L) may be conventional divalent group linkers known in the art. Specifically, L is a single bond, or an alkylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, or a C6 to C6 group. 18 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei.

[0083] n is an integer from 0 to 3. Here, when n is 0, L is a single bond (direct bond), and when n is 1 to 3, it may have one or more selected from the group consisting of the aforementioned alkylene group, cycloalkylene group, arylene group, and heteroarylene group. In this case, when L is multiple, the multiple L may be identical or different from each other.

[0084] Specific examples of the above arylene group linker include phenylene, biphenylene, naphthylene, anthracenylene, indenylene, or pyrantrenylene groups. More specifically, it is preferable that it be a phenylene group or a biphenylene group. In addition, specific examples of heteroarylene group linkers include pyrrole moiety, furan moiety, thiophene moiety, pyridine moiety, pyrimidine moiety, pyrazine moiety, triazine moiety, dibenzofuran moiety, dibenzothiophene moiety, dibenzoselenophenone moiety, carbazolilene group, thiophenylene group, indolylene group, furinilene group, quinolinylene group, pyrroleylene group, imidazolilene group, oxazolilene group, or thiazolilene group.

[0085] For example, L may be a single bond or be embodied in any one selected from the following structural formulas. However, it is not limited thereto.

[0086]

[0087] In the above formula,

[0088] * indicates a portion connected to the above chemical formula 1. In addition, at least one substituent known in the art (e.g., identical to the R2 definition) that is not indicated in the aforementioned structural formula may be substituted.

[0089] In the aforementioned Chemical Formula 1, the alkylene group, cycloalkylene group, arylene group, heteroarylene group of L; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of Ar1~Ar2 and R1~R2 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group of, C2~C 40 alkynyl group, C3~C 40cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

[0090] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be embodied by Chemical Formula 4 below depending on the type of linker (e.g., L).

[0091] [Chemical Formula 4]

[0092]

[0093] In the above formula,

[0094] Z, Ar1, Ar2, X, and n are each defined in Chemical Formula 1.

[0095] For example, one specific example is the above chemical formula 4. It can be selected from the following structural formulas.

[0096]

[0097]

[0098] In the above formula,

[0099] * indicates the part connected to the above chemical formula 4.

[0100] According to another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 5 to 25 below, depending on the number of linkers (e.g., L) connected to a nitrogen-containing heterocyclic ring (e.g., Z-containing ring) and a naphthalene moiety (e.g., X-containing ring) and their bonding positions. However, it is not limited thereto.

[0101] [Chemical Formula 5]

[0102]

[0103] [Chemical Formula 6]

[0104]

[0105] [Chemical Formula 7]

[0106]

[0107] [Chemical Formula 8]

[0108]

[0109] [Chemical Formula 9]

[0110]

[0111] [Chemical Formula 10]

[0112]

[0113] [Chemical Formula 11]

[0114]

[0115] [Chemical Formula 12]

[0116]

[0117] [Chemical Formula 13]

[0118]

[0119] [Chemical Formula 14]

[0120]

[0121] [Chemical Formula 15]

[0122]

[0123] [Chemical Formula 16]

[0124]

[0125] [Chemical Formula 17]

[0126]

[0127] [Chemical Formula 18]

[0128]

[0129] [Chemical Formula 19]

[0130]

[0131] [Chemical Formula 20]

[0132]

[0133] [Chemical Formula 21]

[0134]

[0135] [Chemical Formula 22]

[0136]

[0137] [Chemical Formula 23]

[0138]

[0139] [Chemical Formula 24]

[0140]

[0141] [Chemical Formula 25]

[0142]

[0143] In the above formula,

[0144] Z, Ar1, Ar2, and X are each as defined in Chemical Formula 1.

[0145] For example, in one embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 26 to 37 below, depending on the type of nitrogen-containing heteroaromatic ring (e.g., Z-containing ring) and naphthalene moiety. However, it is not limited thereto.

[0146] [Chemical Formula 26]

[0147]

[0148] [Chemical Formula 27]

[0149]

[0150] [Chemical Formula 28]

[0151]

[0152] [Chemical Formula 29]

[0153]

[0154] [Chemical Formula 30]

[0155]

[0156] [Chemical Formula 31]

[0157]

[0158] [Chemical Formula 32]

[0159]

[0160] [Chemical Formula 33]

[0161]

[0162] [Chemical Formula 34]

[0163]

[0164] [Chemical Formula 35]

[0165]

[0166] [Chemical Formula 36]

[0167]

[0168] [Chemical Formula 37]

[0169]

[0170] In the above formula,

[0171] Ar1, Ar2, L, R1, m, and n are each defined in Chemical Formula 1.

[0172] According to another embodiment of the present invention, the compound represented by Formula 1 may be further embodied in any one of Formulas 38 to 43 below, depending on the type of substituent Ar1 to Ar2 introduced into a nitrogen-containing heteroaromatic ring (e.g., a Z-containing ring). However, it is not limited thereto.

[0173] [Chemical Formula 38]

[0174]

[0175] [Chemical Formula 39]

[0176]

[0177] [Chemical Formula 40]

[0178]

[0179] [Chemical Formula 41]

[0180]

[0181] [Chemical Formula 42]

[0182]

[0183] [Chemical Formula 43]

[0184]

[0185] In the above formula,

[0186] Y is O or S,

[0187] R 12 is hydrogen or C6~C 20 It is Arilgi of, and

[0188] Ring A may be a single-ring or polycyclic hydrocarbon ring group containing or not containing one or more heteroatoms as conventionally known in the art, and may be condensed, fused, cross-linked, or spirocyclically bonded to an adjacent other ring (e.g., core structure). For example, Ring A may be selected from the group consisting of a single-ring or polycyclic alicyclic ring, a single-ring or polycyclic heteroalicyclic ring, a single-ring or polycyclic aromatic ring, or a single-ring or polycyclic heteroaromatic ring. Specifically, Ring A may be C6 to C 24 It is an aromatic ring, or a heteroaromatic ring with 5 to 24 nuclei, more specifically C6~C 18 It is preferable that it be an aromatic ring, or a heteroaromatic ring with 5 to 18 nuclei.

[0189] o and p are identical or different from each other, and each is independently an integer from 1 to 3, and

[0190] Z, L, R1, m, and n are each defined in Chemical Formula 1.

[0191] The compounds represented by the aforementioned chemical formulas 38 to 43 may be further embodied in any one of the following chemical formulas 38a to 43a depending on the type of linker (e.g., L).

[0192] [Chemical Formula 38a]

[0193]

[0194] [Chemical Formula 39a]

[0195]

[0196] [Chemical Formula 40a]

[0197]

[0198] [Chemical Formula 41a]

[0199]

[0200] [Chemical Formula 42a]

[0201]

[0202] [Chemical Formula 43a]

[0203]

[0204] In the above formula,

[0205] Rings A, Z, o, and p are each as defined in chemical formulas 38 to 43, and

[0206] R1, m, and n are each as defined in Chemical Formula 1. Here, The joint position according to the number of can be applied in the same way as described above.

[0207] The compound represented by Formula 1 according to the present invention described above may be further specified as a compound represented by any one of compounds 1 to 160 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] In the present invention, "number of nuclei" refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0217] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0218] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0219] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0220] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply penantated or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0221] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0222] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0223] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0224] In the present invention, "arylamine" means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0225] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0226] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0227] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0228] In the present invention, "condensed ring" refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0229]

[0230] Electron Transport Layer Material

[0231] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0232] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0233] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0234] Electron transport layer materials that can be mixed with the compound of Formula 1 above include electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used individually or in combination of two or more types.

[0235] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0236]

[0237] Electron Transport Auxiliary Layer Material

[0238] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0239] The above electron transport auxiliary layer is positioned between the light-emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0240] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport auxiliary layer materials known in the art. Preferably, it is used alone.

[0241] The electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 above includes electron transport materials that are commonly known in the art. For example, the electron transport materials mixed with the electron transport auxiliary layer material may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0242] In the present invention, when the compound of Formula 1 and the electron transport assisting layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0243]

[0244] Organic Electroluminescent Device

[0245] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0246] Specifically, the present invention relates to 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 Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0247] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising the compound of Chemical Formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifespan improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0248] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0249] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0250] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, the light-emitting layer, more preferably, the phosphorescent host may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0251] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0252] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more of the aforementioned organic layers comprise a compound represented by Chemical Formula 1.

[0253] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0254] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0255] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0256] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0257] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0258]

[0259] The present invention will be explained in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0260]

[0261] [Preparation Examples 1 ~ 6]

[0262] [Preparation Example 1] Synthesis of PN-1

[0263] <Step 1> Synthesis of 1-bromo-2-chlorobenzene

[0264]

[0265] (8-phenylnaphthalen-1-yl)boronic acid (40.0 g, 161.3 mmol), 1-bromo-2-chlorobenzene (30.8 g, 161.3 mmol), Pd(PPh3)4 (5.6 g, 4.8 mmol), and K2CO3 (44.6 g, 322.6 mmol) were added to a mixed solvent of 400 ml of dioxane and 80 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain the compound 1-(2-chlorophenyl)-8-phenylnaphthalene (35.7 g, yield 70%).

[0266] 1H-NMR: δ 8.43 (d, 2H), 8.14 (d, 2H), 7.79-7.61 (m, 6H), 7.46-7.38 (m, 5H)

[0267] Mass: [(M+H)+] : 316

[0268] <Step 2> Synthesis of PN-1

[0269]

[0270] 1-(2-chlorophenyl)-8-phenylnaphthalene (35.7 g, 113.0 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (28.7 g, 113.0 mmol), Pd(dppf)Cl2 (4.1 g, 5.6 mmol), and KOAc (22.2 g, 225.9 mmol) were added to 600 ml of Dioxane and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound PN-1 (33.9 g, yield 44%).

[0271] 1H-NMR: δ 8.43(d, 2H), 8.14(d, 2H), 7.94-7.68(m, 6H), 7.63-7.56(m, 5H), 1,20(s, 12H)

[0272] Mass: [(M+H)+] : 407

[0273]

[0274] [Preparation Example 2] Synthesis of PN-2

[0275] <Step 1> Synthesis of 1-(3-chlorophenyl)-8-phenylnaphthalene

[0276]

[0277] Compound 1-(3-chlorophenyl)-8-phenylnaphthalene (34.7 g, yield 68%) was obtained in the same manner as Step 1 of Preparation Example 1, except that 1-bromo-3-chlorobenzene was used instead of compound 1-bromo-2-chlorobenzene.

[0278] 1H-NMR: δ 8.43(d, 2H), 8.14(d, 2H), 7.97(s, 1H), 7.79(d, 2H), 7.64(t, 2H), 7.48-7.39(m, 6H)

[0279] Mass: [(M+H)+] : 316

[0280] <Step 2> Synthesis of PN-2

[0281]

[0282] Compound PN-2 (32.4 g, yield 42%) was obtained in the same manner as Step 2 of Preparation Example 1, except that 1-(3-chlorophenyl)-8-phenylnaphthalene was used instead of compound 1-(2-chlorophenyl)-8-phenylnaphthalene.

[0283] 1H-NMR: δ 8.43(d, 2H), 8.14(d, 2H), 7.80-7.78(m, 3H), 7.64(t, 2H), 7.50-7.41(m, 6H), 1.20(s, 12H)

[0284] Mass: [(M+H)+] : 407

[0285]

[0286] [Preparation Example 3] Synthesis of PN-3

[0287] <Step 1> Synthesis of 1-(4-chlorophenyl)-8-phenylnaphthalene

[0288]

[0289] Compound 1-(4-chlorophenyl)-8-phenylnaphthalene (35.2 g, yield 69%) was obtained in the same manner as Step 1 of Preparation Example 1, except that 1-bromo-4-chlorobenzene was used instead of compound 1-bromo-2-chlorobenzene.

[0290] 1H-NMR: δ 8.43 (d, 2H), 8.14 (d, 2H), 7.79-7.78 (m, 4H), 7.64-7.62 (m, 4H), 7.46-7.41 (m, 3H)

[0291] Mass: [(M+H)+] : 316

[0292] <Step 2> Synthesis of PN-3

[0293]

[0294] Compound PN-3 (30.8 g, yield 40%) was obtained in the same manner as Step 2 of Preparation Example 1, except that 1-(4-chlorophenyl)-8-phenylnaphthalene was used instead of compound 1-(2-chlorophenyl)-8-phenylnaphthalene.

[0295] 1H-NMR: δ 8.43(d, 2H), 8.14(d, 2H), 7.79(d, 2H), 7.75(d, 2H), 7.66-7.64(m, 4H), 7.45-7.41(m, 3H), 1.20(s, 12H)

[0296] Mass: [(M+H)+] : 407

[0297]

[0298] [Preparation Example 4] Synthesis of PN-4

[0299] <Step 1> Synthesis of 7-(2-chlorophenyl)-1-phenylnaphthalene

[0300]

[0301] Compound 7-(2-chlorophenyl)-1-phenylnaphthalene (34.1 g, yield 67%) was obtained in the same manner as Step 1 of Preparation Example 1, except that (8-phenylnaphthalen-2-yl)boronic acid was used instead of compound (8-phenylnaphthalen-1-yl)boronic acid.

[0302] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.02(s, 1H), 7.78-7.61(m, 6H), 7.46-7.38(m, 4H)

[0303] Mass: [(M+H)+] : 316

[0304] <Step 2> Synthesis of PN-4

[0305]

[0306] Compound PN-4 (31.6 g, yield 41%) was obtained in the same manner as Step 2 of Preparation Example 1, except that 7-(2-chlorophenyl)-1-phenylnaphthalene was used instead of compound 1-(2-chlorophenyl)-8-phenylnaphthalene.

[0307] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.02(s, 1H), 7.80-7.60(m, 6H), 7.48-7.38(m, 4H), 1.20(s, 12H)

[0308] Mass: [(M+H)+] : 407

[0309]

[0310] [Preparation Example 5] Synthesis of PN-5

[0311] <Step 1> Synthesis of 7-(3-chlorophenyl)-1-phenylnaphthalene

[0312]

[0313] Compound 7-(3-chlorophenyl)-1-phenylnaphthalene (35.2 g, yield 69%) was obtained in the same manner as in Step 1 of Preparation Example 4, except that 1-bromo-3-chlorobenzene was used instead of compound 1-bromo-2-chlorobenzene.

[0314] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.02(s, 1H), 7.97(s, 1H), 7.79-7.78(m, 3H), 7.63(d, 1H), 7.48-7.39(m, 6H)

[0315] Mass: [(M+H)+] : 316

[0316] <Step 2> Synthesis of PN-5

[0317]

[0318] Compound PN-5 (32.4 g, yield 42%) was obtained in the same manner as Step 2 of Preparation Example 1, except that 7-(3-chlorophenyl)-1-phenylnaphthalene was used instead of compound 1-(2-chlorophenyl)-8-phenylnaphthalene.

[0319] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.02(s, 1H), 7.83-7.76(m, 4H), 7.63(d, 1H), 7.50-7.38(m, 6H), 1.20(s, 12H)

[0320] Mass: [(M+H)+] : 407

[0321]

[0322] [Preparation Example 6] Synthesis of PN-6

[0323] <Step 1> Synthesis of 7-(4-chlorophenyl)-1-phenylnaphthalene

[0324]

[0325] Compound 7-(4-chlorophenyl)-1-phenylnaphthalene (33.6 g, yield 66%) was obtained in the same manner as in Step 1 of Preparation Example 4, except that 1-bromo-4-chlorobenzene was used instead of compound 1-bromo-2-chlorobenzene.

[0326] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.10(d, 2H), 8.02(s, 1H), 7.79-7.78(m, 4H), 7.63-7.62(m, 3H), 7.46-7.41(m, 3H)

[0327] Mass: [(M+H)+] : 316

[0328] <Step 2> Synthesis of PN-6

[0329]

[0330] Compound PN-6 (29.3 g, yield 38%) was obtained in the same manner as Step 2 of Preparation Example 1, except that 7-(4-chlorophenyl)-1-phenylnaphthalene was used instead of compound 1-(2-chlorophenyl)-8-phenylnaphthalene.

[0331] 1H-NMR: δ 8.52(d, 1H), 8.42(d, 1H), 8.15(d, 1H), 8.02(s, 1H), 7.82-7.78(m, 6H), 7.63-7.62(m, 3H), 7.46-7.41(m, 3H), 1.20(s, 12H)

[0332] Mass: [(M+H)+] : 407

[0333]

[0334] [Synthesized Examples 1 ~ 12]

[0335] [Synthesization Example 1] Synthesis of Compound 1

[0336]

[0337] PN-1 (5.0 g, 12.3 mmol), 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.8 g, 12.3 mmol), Pd(PPh3)4 (0.4 g, 0.4 mmol), and K2CO3 (3.4 g, 24.6 mmol) were added to a mixed solvent of 50 ml of dioxane and 10 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 1 (3.9 g, yield 48%).

[0338] Mass: [(M+H)+] : 665

[0339]

[0340] [Synthesization Example 2] Synthesis of Compound 14

[0341]

[0342] PN-2 (5.0 g, 12.3 mmol), 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (5.2 g, 12.3 mmol), Pd(OAc)2 (0.1 g, 0.4 mmol), XPhos (0.4 g, 0.7 mmol), and Cs2CO3 (8.0 g, 24.6 mmol) were added to 50 ml of Dioxane and 10 ml of H2O, and heated and refluxed for 3 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 14 (4.4 g, yield 48%).

[0343] Mass: [(M+H)+] : 665

[0344]

[0345] [Synthesization Example 3] Synthesis of Compound 18

[0346]

[0347] PN-3 (5.0 g, 12.3 mmol), 2-(4'-chloro-[1,1'-biphenyl]-2-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (6.3 g, 12.3 mmol), Pd(OAc)2 (0.1 g, 0.4 mmol), XPhos (0.4 g, 0.7 mmol), and Cs2CO3 (8.0 g, 24.6 mmol) were added to 50 ml of Dioxane and 10 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 18 (4.3 g, yield 46%).

[0348] Mass: [(M+H)+] : 755

[0349]

[0350] [Synthesization Example 4] Synthesis of Compound 44

[0351]

[0352] PN-4 (5.0 g, 12.3 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.8 g, 12.3 mmol), Pd(PPh3)4 (0.4 g, 0.4 mmol), and K2CO3 (3.4 g, 24.6 mmol) were added to a mixed solvent of 50 ml of dioxane and 10 ml of H2O and reacted for 3 hours under heating and reflux stirring. After the reaction was complete, the compounds were inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain compound 44 (3.7 g, yield 45%).

[0353] Mass: [(M+H)+] : 589

[0354]

[0355] [Synthesization Example 5] Synthesis of Compound 54

[0356]

[0357] PN-5 (5.0 g, 12.3 mmol), 2-([1,1'-biphenyl]-4-yl)-4-(3'-chloro-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine (6.1 g, 12.3 mmol), Pd(OAc)2 (0.1 g, 0.4 mmol), XPhos (0.4 g, 0.7 mmol), and Cs2CO3 (8.0 g, 24.6 mmol) were added to 50 ml of Dioxane and 10 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 54 (3.9 g, yield 43%).

[0358] Mass: [(M+H)+] : 741

[0359]

[0360] [Synthesization Example 6] Synthesis of Compound 76

[0361]

[0362] PN-6 (5.0 g, 12.3 mmol), 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (6.1 g, 12.3 mmol), Pd(OAc)2 (0.1 g, 0.4 mmol), XPhos (0.4 g, 0.7 mmol), and Cs2CO3 (8.0 g, 24.6 mmol) were added to 50 ml of Dioxane and 10 ml of H2O, and heated and stirred under reflux for 3 hours. After the reaction was complete, the mixture was inactivated with a sufficient amount of water, the resulting solid was filtered to remove the solution, and then dried in an oven. The dried solid was purified by column chromatography to obtain Compound 76 (4.1 g, yield 45%).

[0363] Mass: [(M+H)+] : 741

[0364]

[0365] [Synthesization Example 7] Synthesis of Compound 81

[0366]

[0367] Compound 81 (3.7 g, yield 45%) was obtained by the same method as in Synthesis Example 1, except that 4-(2-bromophenyl)-2,6-diphenylpyrimidine was used instead of compound 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

[0368] Mass: [(M+H)+] : 588

[0369]

[0370] [Synthesization Example 8] Synthesis of Compound 82

[0371]

[0372] Compound 82 (4.0 g, yield 44%) was obtained by the same method as in Synthesis Example 2 above, except that 4-([1,1'-biphenyl]-4-yl)-6-(2-chlorophenyl)-2-phenylpyrimidine was used instead of compound 2-(3'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine.

[0373] Mass: [(M+H)+] : 664

[0374]

[0375] [Synthesization Example 9] Synthesis of Compound 110

[0376]

[0377] Compound 110 (4.2 g, yield 46%) was obtained by the same method as in Synthesis Example 3 above, except that 2-(2'-chloro-[1,1'-biphenyl]-2-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of compound 2-(2'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenylpyrimidine.

[0378] Mass: [(M+H)+] : 664

[0379]

[0380] [Synthesization Example 10] Synthesis of Compound 121

[0381]

[0382] Compound 121 (3.4 g, yield 42%) was obtained by the same method as in Synthesis Example 4, except that 4-(2-bromophenyl)-2,6-diphenylpyrimidine was used instead of compound 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

[0383] Mass: [(M+H)+] : 588

[0384]

[0385] [Synthesization Example 11] Synthesis of Compound 131

[0386]

[0387] Compound 131 (3.7 g, yield 40%) was obtained by the same method as in Synthesis Example 5 above, except that 4,6-di([1,1'-biphenyl]-4-yl)-2-(2'-chloro-[1,1'-biphenyl]-2-yl)pyrimidine was used instead of compound 2-([1,1'-biphenyl]-4-yl)-4-(3'-chloro-[1,1'-biphenyl]-2-yl)6-phenyl-1,3,5-triazine.

[0388] Mass: [(M+H)+] : 817

[0389]

[0390] [Synthesization Example 12] Synthesis of Compound 147

[0391]

[0392] Compound 147 (4.0 g, yield 44%) was obtained by the same method as in Synthesis Example 6 above, except that 2-([1,1'-biphenyl]-2-yl)-4-(4'-chloro-[1,1'-biphenyl]-3-yl)-6-phenylpyrimidine was used instead of compound 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0393] Mass: [(M+H)+] : 740

[0394]

[0395] [Examples 1 to 12] Fabrication of Blue Organic Electroluminescent Devices

[0396] After purifying the compound synthesized in the above synthesis example to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was fabricated according to the following process.

[0397] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0398] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / electron transport layer material of Table 1 + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0399]

[0400] [Comparative Examples 1 to 5] Preparation of Blue Organic Electroluminescent Devices

[0401] Blue organic electroluminescent devices of Comparative Examples 1 to 5 were fabricated by performing the same procedure as in Example 1, except that Alq3, DC-1 to DC-4 were used instead of Compound 1 as the electron transport layer material.

[0402] The structures of compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, DC-1 to DC-4 used in the above examples and comparative examples are as follows.

[0403]

[0404]

[0405]

[0406] [Evaluation Example 1]

[0407] For the organic electroluminescent devices prepared in Examples 1 to 12 and Comparative Examples 1 to 5, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0408] Sample Electron Transport Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 13.44557.9 Example 2 Compound 143.34558.1 Example 3 Compound 183.44548.0 Example 4 Compound 443.34557.9 Example 5 Compound 543.44567.9 Example 6 Compound 763.44547.9 Example 7 Compound 813.34558.0 Example 8 Compound 823.44548.0 Example 9 Compound 1103.54547.9 Example 10 Compound 1213.44558.0 Example 11 Compound Example 12 Compound 1313.44547.9 Comparative Example 1473.34558.0 Comparative Example 1 Alq3 4.64575.6 Comparative Example 2 DC-1 4.24586.8 Comparative Example 3 DC-2 4.14576.9 Comparative Example 4 DC-3 4.24566.7 Comparative Example 5 DC-4 4.14576.9

[0409] As shown in Table 1 above, it can be confirmed that the blue organic electroluminescent devices of Examples 1 to 12, which use a compound according to the present invention as an electron transport layer material, are superior in terms of driving voltage, emission peak, and current efficiency compared to the organic light-emitting devices manufactured in Comparative Example 1, which uses conventional Alq3 as an electron transport layer material; and Comparative Examples 2 to 5, which use a compound not containing the composition of the present invention as an electron transport layer material.

[0410]

[0411] [Examples 13 to 24] Fabrication of Blue Organic Electroluminescent Devices

[0412] After purifying the compound synthesized in the above synthesis example to high purity through sublimation using a commonly known method, a blue organic electroluminescent device was fabricated according to the following process.

[0413] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0414] An organic electroluminescent device was fabricated by stacking HI + 2% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / electron transport auxiliary layer material of Table 1 (5 nm) / ET + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the ITO transparent electrode prepared as above.

[0415]

[0416] [Comparative Example 6]

[0417] A blue organic electroluminescent device of Comparative Example 6 was fabricated by performing the same procedure as in Example 13, except that no electron transport auxiliary layer material was used.

[0418]

[0419] [Comparative Examples 7 to 10] Preparation of blue organic electroluminescent devices

[0420] Blue organic electroluminescent devices of Comparative Examples 7 to 10 were fabricated by performing the same procedure as in Example 13, except that DC-1 to DC-4 were used instead of Compound 1 as the electron transport auxiliary layer material.

[0421] The structures of the compounds HI, HAT-CN6, EB, BH, BD, Liq, Alq3, and DC-1 to DC-4 used at this time are as specified in the aforementioned Examples 1 to 12. In addition, the structure of compound ET is as follows.

[0422]

[0423]

[0424] [Evaluation Example 2]

[0425] For the organic electroluminescent devices prepared in Examples 13 to 24 and Comparative Examples 6 to 10, respectively, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0426] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 13 Compound 13.14548.1 Example 14 Compound 143.24558.2 Example 15 Compound 183.34558.1 Example 16 Compound 443.14548.1 Example 17 Compound 543.24558.1 Example 18 Compound 763.34548.2 Example 19 Compound 813.14558.1 Example 20 Compound 823.24548.2 Example 21 Compound 1103.24548.2 Example 22 Compound 1213.34558.1 Example 23 Compound 1313.34558.1 Example 24 Compound 1473.24548.1 Comparative Example 6-4.64566.3 Comparative Example 7 DC-14.04566.9 Comparative Example 8 DC-24.04567.1 Comparative Example 9 DC-34.04566.9 Comparative Example 10 DC-44.04567.0

[0427] As shown in Table 2 above, it was confirmed that the blue organic electroluminescent device of Examples 13 to 24, which uses a compound according to the present invention as an electron transport auxiliary layer material, is superior to the organic electroluminescent device of Comparative Example 6, which does not include an electron transport auxiliary layer, and Comparative Examples 7 to 10, which uses a compound not including the composition of the present invention as an electron transport auxiliary layer material, in terms of the driving voltage, emission peak, and current efficiency of the device.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, Z are identical or different from each other, each independently CR2 or N, provided that at least one of the plurality of Zs is N, Ar1 and Ar2 are identical or different from each other, and each independently C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, L is a single bond, or an alkylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, or C6 to C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei, n is an integer from 0 to 3, and X is a moiety selected from the group of substituents represented by the following structural formula, and In the above formula, * indicates the part connected to the above chemical formula 1, and R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C3~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 Selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei; m is an integer from 0 to 5, and The alkylene group, cycloalkylene group, arylene group, heteroarylene group of the above L; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of the above Ar1~Ar2 and R1~R2 are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei, and in the case where there are multiple substituents, they may be identical or different from each other.

2. In Paragraph 1, The above Z-containing ring is a compound selected from the group of substituents represented by the following chemical formula: In the above formula, * indicates the part connected to the above chemical formula 1, and Ar1, Ar2, and R2 are each as defined in Paragraph 1.

3. In Paragraph 1, The above Ar1 is C6~C 60 It is Arilgi of, and The above Ar2 is C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

4. In Paragraph 1, Ar1 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1.

5. In Paragraph 1, Ar2 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1, and R 11 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

6. In Paragraph 1, L is a compound in which the bond is a single bond or is selected from any one of the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 1.

7. In Paragraph 1, R1 is deuterium (D), C1~C 40 alkyl group of, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, A compound in which m is an integer from 0 to 3.

8. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 2 or 3: [Chemical Formula 2] [Chemical Formula 3] In the above formula, Z, Ar1, Ar2, L, R1, m, and n are each as defined in Paragraph 1.

9. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 4: [Chemical Formula 4] In the above formula, Z, Ar1, Ar2, X and n are each as defined in Paragraph 1.

10. In Paragraph 9, of the above chemical formula 4 is a compound selected from the following structural formulas: In the above formula, * indicates the part connected to the above chemical formula 4.

11. In Paragraph 1, A compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 5 to 25: [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] In the above formula, Z, Ar1, Ar2, and X are each as defined in Paragraph 1.

12. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 26 to 37: [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 formula, Ar1, Ar2, L, R1, m, and n are each as defined in Paragraph 1.

13. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 38 to 43: [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] In the above formula, Y is O or S, R 12 is hydrogen or C6~C 20 It is Arilgi of, and Ring A is a monocyclic or polycyclic hydrocarbon ring that may or may not contain heteroatoms, and o and p are identical or different from each other, and each is independently an integer from 1 to 3, and Z, L, R1, m, and n are each as defined in Paragraph 1.

14. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 1 to 160.

15. In Paragraph 1, The compound represented by the above chemical formula 1 is a compound that is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer.

16. 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 described in any one of claims 1 to 17.

17. In Paragraph 16, An organic electroluminescent device in which the organic layer containing the above compound is selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, and an electron transport auxiliary layer.

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