Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to: a novel compound having excellent carrier transport ability, light-emitting ability and thermal stability; and an organic electroluminescent device comprising same in one or more organic layers, and thus the present invention has improved properties of luminous efficiency, driving voltage, lifespan and the like.

Description

Organic compounds and organic electroluminescent devices using the same

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

[0002]

[0003] Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices led to the blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic electroluminescent device with a layered structure divided into functional layers, a hole layer and an emission layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, development has been made by introducing characteristic organic layers within the device, which has led to the development of specialized materials used for this.

[0004] In organic electroluminescent devices, when a voltage is applied between two electrodes, holes are injected 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 according to their function, such as luminescent materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0005] The light-emitting layer materials of organic electroluminescent devices can be classified into blue, green, and red light-emitting materials according to the emission color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. In addition, a host / dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. The 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. The development of such phosphorescent materials is focusing on not only phosphorescent dopants but also phosphorescent host materials because it can theoretically improve luminous efficiency by up to four times compared to fluorescence. Currently, NPB, BCP, Alq3, etc. are widely known as materials used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as luminescent materials. Among the phosphorescent materials, Ir-containing metal complex compounds, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are used as blue, green, and red dopant materials, especially those with significant advantages in terms of efficiency enhancement among luminescent materials. To date, CBP has demonstrated excellent properties as a phosphorescent host material.

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

[0007]

[0008] [Prior Art Literature]

[0009] Republic of Korea Publication Patent No. 10-2020-0103052

[0010]

[0011] The present invention can be applied to organic electroluminescent devices, and the purpose of the present invention is to provide a novel organic compound having excellent hole and electron injection and transport capabilities, luminescence capabilities, etc.

[0012] In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and an improved lifespan, including the novel organic compound.

[0013]

[0014] To achieve the above-mentioned purpose, the present invention provides a compound represented by the following chemical formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] A plurality of Xs are identical or different and are each independently CR5 or N, provided that at least two of the plurality of Xs are N,

[0019] R1 is C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group of C6~C 60 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring,

[0020] a is an integer greater than or equal to 1, and when a is greater than or equal to 2, multiple R1s are the same or different from each other.

[0021] L1 and L2 are the same or different and are each independently C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0022] m is an integer from 1 to 3, n is an integer from 0 to 3,

[0023] Ar2 is hydrogen, deuterium (D), 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, C3~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, C6~C 60 Arylamine group, C5~C 60 Selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms,

[0024] Ar1 is a moiety represented by the following chemical formula 2,

[0025] [Chemical Formula 2]

[0026]

[0027] In the above chemical formula 2,

[0028] * is connected to chemical formula 1,

[0029] Y is O, S or NR4,

[0030] Ring A and ring B are the same or different from each other, and each independently contains or does not contain a heteroatom C5~C 18 It is a monocyclic or polycyclic hydrocarbon ring group,

[0031] R2 to R5 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~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, C6~C 60 Arylamine group, C5~C 60 is selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring;

[0032] b is an integer from 0 to 3, c is an integer from 0 to 4,

[0033] The arylene group, heteroarylene group of the above L1~L2; the aryl group, heteroaryl group of the above R1, 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 R2~R5 and Ar2 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 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 60Aryloxy 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, C6~C 60 Arylamine group, 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 nuclear atoms, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0034] 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.

[0035] Here, the organic layer including the compound represented by the 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 life-span improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by the 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.

[0036]

[0037] As one embodiment of the present invention, the compound represented by the above chemical formula 1 can be used as an organic layer material of an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0038] In particular, when the compound represented by the chemical formula 1 of the present invention is used as a phosphorescent host, electron transport layer, or electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long life characteristics compared to conventional host materials or electron transport materials.

[0039] Accordingly, the organic electroluminescent device including the compound of the above chemical formula 1 can be significantly improved in aspects such as excellent luminescence performance, low driving voltage, long life, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0040] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0041]

[0042] Hereinafter, the present invention will be described in detail.

[0043] <New organic compounds>

[0044] The present invention provides a novel aryl compound having excellent thermal stability, carrier transport ability, and luminescence ability.

[0045] Specifically, the novel organic compound according to the present invention comprises a plurality of aryl groups; and a ring compound having an unshared electron pair, such as a dibenzo / carbazole moiety, to which a nitrogen-containing heteroaromatic ring (e.g., azine) as an electron withdrawing group (EWG) having excellent electron transport ability is bonded to form a basic skeleton, and has a structure that essentially includes a linker (e.g., L1) between the nitrogen-containing heteroaromatic ring and the dibenzo / carbazole moiety.

[0046] The compound represented by the above chemical formula 1 essentially includes a linker (L1), preferably an arylene group, between a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring) having EWG characteristics and a cyclic compound (e.g., Ar1, chemical formula 2), so that the conjugation length is relatively increased compared to a compound having the same structure but not including a linker and directly bonded, thereby increasing the stability of the molecule and allowing for a higher device lifetime than the prior art. In addition, since the linker (L1) is essentially included, mobility control is easy. For example, when a naphthylene linker is introduced, the effect of lowering mobility can be exerted. In addition, as the ortho position of the linker increases, steric hindrance is maximized, thereby increasing the triplet energy (T1), gathering excitons toward the host of the emitting layer, and improving the efficiency and lifetime characteristics of the device through exciton blocking. In addition, when another azine group with different EWG characteristics from a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring) is introduced as an additional substituent, the device characteristics can be further improved by having a shallow LUMO.

[0047] In addition, the compound of the above chemical formula 1 increases the electron density of EWG, which has a structural electron transport ability, by substituting a nitrogen-containing heteroaromatic ring (e.g., triazine, pyrimidine, etc.) having an unshared electron pair on EWG with a number of aryl groups, and thus the electron transport ability is further improved compared to the existing known material structure, resulting in an effect of increased efficiency. In addition, it has a rigid chemical structure due to the ring compound bonded to EWG, and is excellent in terms of high glass transition temperature (Tg) and thermal stability. In addition, by introducing an azine group, which is a functional group with strong electron withdrawing ability (EWG), to improve the electron transfer rate, it can have physicochemical properties more suitable for electron injection and electron transport.

[0048] And since the compound represented by Chemical Formula 1 of the present invention has high triplet energy, 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.

[0049] As described above, when the compound represented by the chemical formula 1 of the present invention is applied as an organic layer material of an organic electroluminescent device, preferably as 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, or a life-span improvement layer material, the performance and life-span characteristics of the organic electroluminescent device can be significantly improved. As a result, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0050] According to the present invention, a compound represented by Chemical Formula 1 comprises a plurality of aryl groups (e.g., R1), a nitrogen-containing heteroaromatic ring having electron withdrawing group (EWG) characteristics with excellent electron transport ability (e.g., an X-containing ring), and a ring compound having an unshared electron pair (e.g., a dibenzo / carbazole moiety, e.g., a Y-containing ring of Chemical Formula 2), and has a basic skeletal structure in which the nitrogen-containing heteroaromatic ring and the dibenzo / carbazole moiety are connected via a linker (e.g., L1).

[0051] The above nitrogen-containing heteroaromatic ring (e.g., X-containing ring) may be a monocyclic or polycyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms, and a monocyclic nitrogen-containing heteroaryl group is particularly preferred.

[0052] In one embodiment of such nitrogen-containing heteroaromatic rings (e.g., X-containing rings), a plurality of Xs are the same or different, and are each independently N or CR5, provided that at least two of the plurality of Xs are N. In a specific example, the plurality of Xs contain 2 to 3 Ns, preferably 3 Ns. By including a heterocycle containing 2 to 3 nitrogens in this way, better electron absorption properties are exhibited, which is advantageous for electron injection and transport.

[0053] Here, R5 is hydrogen, deuterium, 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, C3~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, C6~C 60 Arylamine group, C5~C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring. Specifically, R5 is hydrogen, deuterium, C1~C 40 Alkyl group of C6~C 40 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms.

[0054] For example, the nitrogen-containing heteroaromatic ring (e.g., X-containing ring) may be further specified as one selected from the following structural formulas, but is not limited thereto.

[0055]

[0056] In the above formula,

[0057] * indicates a part connected to the above chemical formula 1,

[0058] Ar1~Ar2, R5, L1, and m are each as defined in chemical formula 1.

[0059] In the above nitrogen-containing heterocycle (e.g., a ring containing X1 to X3), Ar1 and Ar2 are substituted with various substituents. These Ar1 and Ar2 may be the same or different from each other, and it is preferable that Ar1 and Ar2 are different. Either of the above Ar1 and Ar2 is a dibenzo / carbazole moiety, and specifically, Ar1 is a Y-containing ring which is a ring compound having a lone pair of electrons represented by the following chemical formula 2.

[0060] [Chemical Formula 2]

[0061]

[0062] In the above chemical formula 2,

[0063] * is connected to chemical formula 1,

[0064] Y is O, S or NR4,

[0065] Ring A and ring B are the same or different from each other, and each independently contains or does not contain a heteroatom C5~C 18It may be a monocyclic or polycyclic hydrocarbon ring group. These rings A and B may each be a condensed or fused monocyclic or polycyclic hydrocarbon ring or nitrogen-containing ring known in the art, and may be, for example, a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring. Preferably, it may be a monocyclic or polycyclic aromatic ring having 6 to 12 carbon atoms, or a monocyclic or polycyclic heteroaromatic ring having 5 to 12 nuclear atoms containing a heteroatom. Here, the heteroatom may be N, O, or S.

[0066] R2 to R4 are the same or different and each independently represent 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 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, C3~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, C6~C 60 Arylamine group, C5~C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring of a conventional monocyclic or polycyclic form. Specifically, R2 to R4 are each independently C6~C 60is selected from the group consisting of an aryl group of C6~C and a heteroaryl group having 5 to 60 nuclear atoms, more specifically 40 It is preferably selected from the group consisting of an aryl group and a heteroaryl group having 5 to 40 nuclear atoms.

[0067]

[0068] b is an integer from 0 to 3, and c is an integer from 0 to 4. Here, when b is 0, ring A is unsubstituted and hydrogen is present, and when b is 1 or 2, ring A may have the aforementioned substituents except hydrogen. Similarly, when c is 0, hydrogen is present in ring B, and when c is 1 or 2, ring B may have the aforementioned substituents.

[0069] However, the above-mentioned Y-containing ring may be substituted or unsubstituted with a substituent described below, and the total number of carbon atoms contained in the Y-containing ring substituted and / or unsubstituted in this way includes at least 8 or more. Specifically, it may include 8 to 24 carbon atoms, and more specifically, 16 to 24 carbon atoms.

[0070] For example, the ring compound represented by the above chemical formula 2 (e.g., Y-containing ring, Ar1) can be further specified as one selected from the structural formulas below. However, it is not limited thereto.

[0071]

[0072]

[0073] In the above formula,

[0074] * indicates a part connected to the above chemical formula 1,

[0075] Ring D is the same or different from each other, and each independently represents a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom,

[0076] Y, R 2,R3, b and c are each as defined in chemical formula 2.

[0077] As a preferred specific example, the ring compound represented by the above chemical formula 2 (e.g., Y-containing ring, Ar1) can be further specified as one selected from the following structural formulas.

[0078]

[0079]

[0080]

[0081]

[0082] In the above formula,

[0083] * indicates a part connected to the above chemical formula 1,

[0084] R4 is as defined in Chemical Formula 2. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definitions of R2 to R5) may be substituted.

[0085] Ar2 substituted in the above nitrogen-containing heteroaromatic ring (e.g., X-containing ring) is hydrogen, deuterium, 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 60can be selected from the arylamine group of. Specifically, Ar2 is C6~C 40 Selected from the group consisting of aryl group and heteroaryl group having 5 to 40 nuclear atoms, more specifically C6~C 20 It is preferable to select from an aryl group and a heteroaryl group having 5 to 20 nuclear atoms.

[0086] For example, Ar2 may be further specified as one selected from the structural formula below, but is not limited thereto.

[0087]

[0088] In the above formula,

[0089] * indicates a part connected to the above chemical formula 1,

[0090] R 11 Silver hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definition of R2 to R5) may be substituted.

[0091] The compound of formula 1 according to the present invention essentially comprises a phenyl group substituted with a plurality of aryl groups (R1), a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring), and a ring compound having a lone pair of electrons (e.g., a Y-containing ring), wherein the nitrogen-containing heteroaromatic ring (e.g., an X-containing ring) and the ring compound having a lone pair of electrons (e.g., a Y-containing ring) are connected by a non-single-bonded linker (e.g., L1) positioned therebetween. Accordingly, the compound of formula 1 is structurally and effectively differentiated from conventional compounds in which a nitrogen-containing heteroaromatic ring and a dibenzo / carbazole-based ring compound are directly bonded. Specifically, when a non-single-bonded linker (e.g., L1) is essentially included, the HOMO region can be expanded to provide an advantage in the HOMO-LUMO distribution, and charge transfer efficiency can be increased through appropriate HOMO-LUMO overlap. In addition, the conjugation length is relatively increased, which increases the stability of the molecule, and thus, the device can have long-life characteristics compared to conventional compounds, and mobility control is easy. In addition, as the ortho position of the linker increases, it induces maximization of steric hindrance, which increases the triplet energy (T1), gathers excitons toward the host of the emitting layer, and improves the efficiency and life characteristics of the device through exciton blocking.

[0092] Meanwhile, in the compound of the above chemical formula 1, the phenyl group substituted with the aryl group (R1) and the nitrogen-containing heteroaromatic ring (e.g., X-containing ring) may be directly bonded (e.g., n=0) or connected through a separate linker (e.g., L2).

[0093] Specifically, L1 and L2 are not particularly limited and may be linkers of common divalent groups known in the art. Specifically, L is C6~C 18It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms. More specifically, each independently C6~C 12 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 12 nuclear atoms.

[0094] Here, the number of linkers L1 and L2, i.e., m, is an integer from 1 to 3, and n is an integer from 0 to 3. For example, if n is 0, it corresponds to a single bond (direct bond), so L2 is a single bond. In addition, if m and n are 1 to 3, the remaining substituents excluding the single bond in the above-mentioned linker definition may be present, and multiple L1s and L2s may be the same or different from each other.

[0095] Specific examples of the above arylene linker and heteroarylene linker include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, an indoylene group, a purinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolyl group, a thiazolyl group, a pyridinylene group, a pyrimidinylene group, a dibenzofuran-based moiety, a dibenzothiophene-based moiety, and / or a dibenzoselenophenone-based moiety. More specifically, a phenylene group, a biphenylene group, or a terphenylene group is preferable.

[0096] For example, L1 to L2 may be the same or different from each other, and may each be a linking group independently selected from the following structural formula.

[0097]

[0098] In the above formula,

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

[0100] R 12 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms. In addition, although not shown in the structural formula described above, at least one substituent known in the art (e.g., the same as the definition of R2 to R5) may be substituted.

[0101] The compound of formula 1 according to the present invention comprises a plurality of aryl groups (e.g., an R1-containing ring) on ​​one side of a nitrogen-containing heterocycle (e.g., an X-containing ring), specifically on the other side of a dibenzo / carbazole moiety based on the long axis of the molecule.

[0102] R1 is C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group of C6~C 60 , and a heteroaryl group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring, and the alkyl group, cycloalkyl group, aryl group, and heteroaryl group of R1 are each independently C1 to C 40 Alkyl group of C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms. At this time, the number of R1, i.e., a, is an integer of 1 or more, preferably 1 to 5. When a is 2 or more, multiple R1s may be the same or different from each other.

[0103] For example, R1 is C6~C 30 , and a heteroaryl group having 5 to 30 nuclear atoms, or may be a condensed ring formed by combining with an adjacent group, and a is an integer of 2 to 5, and (R1) substituted or unsubstituted with a substituent a The total number of carbon atoms contained in may include at least 18 or more. More specifically, R1 is C6~C18 is an aryl group, a is an integer of 3 to 5, and the total number of carbon atoms contained in R1, which is unsubstituted or substituted with a substituent described below, may include 18 to 36 carbon atoms.

[0104] In the above-mentioned chemical formula 1, the arylene group, heteroarylene group of L1~L2; the aryl group, heteroaryl group of R1, 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 R2~R5 and Ar2 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 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, C6~C 60 Arylamine group, 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 nuclear atoms, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0105] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 3 to 6 depending on the type of nitrogen-containing heteroaromatic ring (e.g., X-containing ring). However, the present invention is not limited thereto.

[0106] [Chemical Formula 3]

[0107]

[0108] [Chemical Formula 4]

[0109]

[0110] [Chemical Formula 5]

[0111]

[0112] [Chemical Formula 6]

[0113]

[0114] In the above formula,

[0115] A, B, Y, Ar2, L1-L2, R1~R3, a~c, m and n are each as defined in chemical formula 1.

[0116] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 may be further specified as one of the following chemical formulas 7 to 15, depending on the type of the ring moiety (e.g., Y-containing ring) having a non-shared electron pair. However, the present invention is not limited thereto.

[0117] [Chemical Formula 7]

[0118]

[0119] [Chemical Formula 8]

[0120]

[0121] [Chemical Formula 9]

[0122]

[0123] [Chemical Formula 10]

[0124]

[0125] [Chemical Formula 11]

[0126]

[0127] [Chemical Formula 12]

[0128]

[0129] [Chemical Formula 13]

[0130]

[0131] [Chemical Formula 14]

[0132]

[0133] [Chemical Formula 15]

[0134]

[0135] In the above formula,

[0136] Ring D is a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom,

[0137] X, Y, Ar2, L1-L2, R1~R3, a~c, m and n are each as defined in chemical formula 1.

[0138] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 16 to 18, depending on the type of L1 linker positioned between the nitrogen-containing heteroaromatic ring (e.g., X-containing ring) and the ring moiety (e.g., Y-containing ring). However, the present invention is not limited thereto.

[0139] [Chemical Formula 16]

[0140]

[0141] [Chemical Formula 17]

[0142]

[0143] [Chemical Formula 18]

[0144]

[0145] In the above formula,

[0146] Z is O or S,

[0147] Ring E is an aromatic condensed polycyclic group having 10 to 30 carbon atoms of a common divalent group known in the art, and can be specifically selected from a naphthalene group, a phenalene group, an anthracene group, a fluoranthene group, a triphenylene group, a phenanthrene group, a pyrene group, a chrysene group, and a perylene group.

[0148] A, B, X, Y, Ar2, L2, R1~R3, a~c, m and n are each as defined in chemical formula 1.

[0149] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as the following chemical formula 19 or chemical formula 20 depending on the types of L1 and L2 linkers. However, the present invention is not limited thereto.

[0150] [Chemical Formula 19]

[0151]

[0152] [Chemical Formula 20]

[0153]

[0154] In the above formula,

[0155] n is an integer from 1 to 3,

[0156] A, B, X, Y, Ar2, R1~R3, a~c, and m are each as defined in chemical formula 1.

[0157] According to another embodiment of the present invention, the compound represented by the above chemical formula 1 can be further specified as one of the following chemical formulas 21 to 32 depending on the type of number and position of R1. However, the present invention is not limited thereto.

[0158] [Chemical Formula 21]

[0159]

[0160] [Chemical Formula 22]

[0161]

[0162] [Chemical Formula 23]

[0163]

[0164] [Chemical Formula 24]

[0165]

[0166] [Chemical Formula 25]

[0167]

[0168] [Chemical Formula 26]

[0169]

[0170] [Chemical Formula 27]

[0171]

[0172] [Chemical Formula 28]

[0173]

[0174] [Chemical Formula 29]

[0175]

[0176] [Chemical Formula 30]

[0177]

[0178] [Chemical Formula 31]

[0179]

[0180] [Chemical Formula 32]

[0181]

[0182] In the above formula,

[0183] Ring D is a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom,

[0184] A, B, X, Y, Ar2, L1~L2, R1~R3, b~c, m and n are each as defined in Chemical Formula 1, and when there are multiple R1s, the multiple R1s may be the same or different.

[0185] The compound represented by the chemical formula 1 of the present invention described above can be further specified as the compounds exemplified below, for example, compounds represented by 1 to 120. However, the compound represented by the chemical formula 1 of the present invention is not limited to those exemplified below.

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] In the present invention, the "number of nuclear atoms" refers to the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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.

[0199] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom selected from the group consisting of N, O, S, and 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.

[0200] 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.

[0201] 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 alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0202] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms.

[0203] 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.

[0204] 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 in the ring, preferably 1 to 3 carbon atom(s), 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.

[0205] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 40 carbon atoms.

[0206] In the present invention, “fused ring” means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0207]

[0208] Electron transport layer material

[0209] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0210] The above electron transport layer (ETL) plays a role in moving electrons injected from the cathode to an adjacent layer, specifically, the light-emitting layer.

[0211] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.

[0212] The electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. Non-limiting examples of electron transport materials that can be used include oxazole compounds, isoxazole 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 alone or in combination of two or more.

[0213] 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.

[0214]

[0215] <Electron transport auxiliary layer material>

[0216] In addition, the present invention provides an electron transport auxiliary layer comprising a compound represented by the above chemical formula 1.

[0217] The 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.

[0218] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport auxiliary layer material known in the art. It is preferably used alone.

[0219] The electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes an electron transport material commonly known in the art. For example, the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a heterocyclic derivative containing nitrogen, etc.

[0220] In the present invention, when the compound of the above chemical formula 1 and the electron transport auxiliary layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0221]

[0222] Organic electroluminescent devices

[0223] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by the chemical formula 1 according to the present invention.

[0224] Specifically, the present invention is 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. At this time, the compound may be used alone or in a mixture of two or more.

[0225] The organic layer above one or more layers may be at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-span improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers includes a compound represented by the chemical formula 1. Specifically, it is preferable that the organic layer including the compound of the chemical formula 1 is a light-emitting layer (more specifically, a phosphorescent host material), an electron transport layer, and an electron transport auxiliary layer.

[0226] The light-emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and may include the compound of the above chemical formula 1 as the host material. In addition, the light-emitting layer of the present invention may include a known compound in the art other than the compound of the above chemical formula 1 as the host.

[0227] When the compound represented by the above chemical formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the bonding force between holes and electrons in the light-emitting layer increases, thereby improving the efficiency (luminescent efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, the compound represented by the above chemical formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by the chemical formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light-emitting layer having high efficiency.

[0228] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have 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 laminated. At this time, at least one 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 the chemical formula 1, and preferably, the light-emitting layer, and more preferably, the phosphorescent host, may include a compound represented by the chemical formula 1. Meanwhile, an electron injection layer may be additionally laminated on the electron transport layer.

[0229] 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.

[0230] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers described above includes a compound represented by the chemical formula 1.

[0231] 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.

[0232] The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet, etc. can be used.

[0233] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0234] In addition, the cathode material may be any cathode material known in the art without limitation. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0235] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and conventional materials known in the art can be used without limitation.

[0236]

[0237] 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.

[0238] [Preparation Example 1]

[0239] <Step 1> Synthesis of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl

[0240]

[0241] 100 g (290.9 mmol) of 2'-bromo-6'-chloro-1,1':4',1''-terphenyl, 37.3 g (305.5 mmol) of phenylboronic acid, 10.1 g (8.7 mmol) of Pd(PPh3)4, and 120.6 g (872.98 mmol) of K2CO3 were added to 970 ml of THF and 240 ml of H2O, and heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO4, and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 75.6 g (yield 76.3%) of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl.

[0242] 1 H-NMR: δ 8.25 (s, 1H), 8.02 (s, 1H), 7.79 (d, 2H), 7.75 (d, 2H), 7.64 (d, 2H), 7.49 (t, 2H), 7.46 (t, 4H), 7.41 (t, 3H).

[0243] Mass: [(M+H) + ] : 341

[0244] <Step 2> Synthesis of Core1

[0245]

[0246] 75.6 g (221.7 mmol) of 3'-chloro-5'-phenyl-1,1':2',1''-terphenyl, 73.2 g (288.3 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 36.1 g (6.7 mmol) of Pd2(dba), 65.3 g (665.4 mmol) of KOAc, and 6.3 g (13.3 mmol) of Xphos were added to 750 ml of 1,4-Dioxane and heated under reflux for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over MgSO4, and filtered. After filtering, the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and then solidified using methanol. The solid was filtered, washed with methanol, and dried in an oven to obtain 72.7 g of Core1 (yield 75.8%).

[0247] 1 H-NMR: δ 8.25 (s, 1H), 8.02 (s, 1H), 7.79 (d, 2H), 7.75 (d, 2H), 7.64 (d, 2H), 7.49 (t, 2H), 7.46 (t, 4H), 7.41 (t, 3H), 1.2(s, 12H).

[0248] Mass: [(M+H) + ] : 433

[0249]

[0250] [Preparation Example 2]

[0251] <Step 1> Synthesis of 5'-chloro-3'-phenyl-1,1':2',1'':3'',1'''-quaterphenyl

[0252]

[0253] 100 g (291.0 mmol) of 2'-bromo-5'-chloro-1,1':3',1''-terphenyl, 60.5 g (305.6 mmol) of [1,1'-biphenyl]-3-ylboronic acid, 10.1 g (8.7 mmol) of Pd(PPh3)4, and 120.7 g (873.0 mmol) of K2CO3 were added to 870 ml of THF and 220 ml of H2O, and 89.4 g (yield 73.7%) of 5'-chloro-3'-phenyl-1,1':2',1'':3'',1'''-quaterphenyl was obtained using the same method as in Step 1 of Preparation Example 1.

[0254] 1 H-NMR: δ 8.26 (s, 2H), 7.80 (d, 4H), 7.95 (s, 1H), 7.76 (d, 2H), 7.74 (t, 1H), 7.62 (d, 2H), 7.50 (t, 2H), 7.46 (t, 4H), 7.41(t, 3H).

[0255] Mass: [(M+H) + ] : 416

[0256] <Step 2> Synthesis of Core2

[0257]

[0258] 89.4 g (214.4 mmol) of 5'-chloro-3'-phenyl-1,1':2',1'':3'',1'''-quaterphenyl, 70.8 g (278.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 35.9 g (6.4 mmol) of Pd2(dba), 63.1 g (643.2 mmol) of KOAc, and 6.1 g (12.9 mmol) of Xphos were added to 750 ml of 1,4-Dioxane, and 85.4 g (yield 78.3%) of Core2 was obtained using the same method as the Core1 synthesis method of Preparation Example 1.

[0259] 1 H-NMR: δ 8.26 (s, 2H), 7.80 (d, 4H), 7.95 (s, 1H), 7.76 (d, 2H), 7.74 (t, 1H), 7.62 (d, 2H), 7.50 (t, 2H), 7.46 (t, 4H), 7.41(t, 3H), 1.2(s, 12H).

[0260] Mass: [(M+H) + ] : 508

[0261]

[0262] [Preparation Example 3]

[0263] <Step 1> Synthesis of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl

[0264]

[0265] 70 g (261.6 mmol) of 2'-bromo-5'-chloro-1,1':3',1''-terphenyl, 54.4 g (274.7 mmol) of phenylboronic acid, 49.1 g (7.8 mmol) of Pd(PPh3), and 108.5 g (784.9 mmol) of K2CO3 were added to 870 ml of THF and 220 ml of H2O, and 47.5 g (yield 68.4%) of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl was obtained using the same method as in Step 1 of Preparation Example 1.

[0266] 1 H-NMR: δ 8.26 (s, 2H), 7.79 (d, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.46 (t, 4H), 7.41 (t, 3H).

[0267] Mass: [(M+H) + ] : 341

[0268] <Step 2> Synthesis of Core3

[0269]

[0270] 47.5 g (139.3 mmol) of 5'-chloro-3'-phenyl-1,1':2',1''-terphenyl, 45.9 g (181.1 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 33.8 g (4.2 mmol) of Pd2(dba), 41.0 g (417.9 mmol) of KOAc, and 4.0 g (8.3 mmol) of Xphos were added to 470 ml of 1,4-Dioxane, and 45.25 g (yield 75.1%) of Core3 was obtained using the same method as the Core1 synthesis method of Preparation Example 1.

[0271] 1 H-NMR: δ 8.26 (s, 2H), 7.79 (d, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.46 (t, 4H), 7.41 (t, 3H), 1.2(s, 12H).

[0272] Mass: [(M+H) + ] : 433

[0273]

[0274] [Preparation Example 4]

[0275] <Step 1> Synthesis of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl

[0276]

[0277] 60 g (224.3 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 46.6 g (235.5 mmol) of [1,1'-biphenyl]-3-ylboronic acid, 47.8 g (6.7 mmol) of Pd(PPh3), and 93.0 g (672.8 mmol) of K2CO3 were added to 490 ml of THF and 125 ml of H2O, and 59.4 g (yield 77.7%) of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl was obtained using the same method as in Step 1 of Preparation Example 1.

[0278] 1H-NMR: δ 8.07 (s, 2H), 7.95 (s, 1H), 7.82 (s, 1H), 7.76 (d, 4H), 7.73 (t, 1H), 7.62 (d, 2H), 7.50 (t, 4H), 7.41 (t, 2H).

[0279] Mass: [(M+H) + ] : 340

[0280] <Step 2> Synthesis of Core4

[0281]

[0282] 59.4 g (174.3 mmol) of 5'-chloro-1,1':3',1'':3'',1'''-quaterphenyl, 57.5 g (226.6 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 34.8 g (5.3 mmol) of Pd2(dba), 51.3 g (522.8 mmol) of KOAc, and 5.0 g (10.5 mmol) of Xphos were added to 430 ml of 1,4-Dioxane, and 65.8 g (87.3% yield) of Core4 was obtained using the same method as the Core1 synthesis method of Preparation Example 1.

[0283] 1H-NMR: δ 8.07 (s, 2H), 7.95 (s, 1H), 7.82 (s, 1H), 7.76 (d, 4H), 7.73 (t, 1H), 7.62 (d, 2H), 7.50 (t, 4H), 7.41(t, 2H), 1.2(s, 12H).

[0284] Mass: [(M+H) + ] : 432

[0285]

[0286] [Preparation Example 5]

[0287] <Step 1> Synthesis of Core5

[0288]

[0289] 70 g (171.2 mmol) of 5'-chloro-3'-phenyl-4''-(trifluoromethyl)-1,1':2',1''-terphenyl, 56.5 g (222.6 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 34.7 g (5.1 mmol) of Pd2(dba), 50.4 g (513.6 mmol) of KOAc, and 4.9 g (10.3 mmol) of Xphos were added to 700 ml of 1,4-Dioxane, and 68.4 g (yield 79.8%) of Core5 was obtained using the same method as the Core1 synthesis method of Preparation Example 1.

[0290] 1H-NMR: δ 7.96 (s, 2H), 7.79 (d, 4H), 7.66 (d, 2H), 7.46 (t, 4H), 7.41 (t, 2H), 7.31 (d, 2H), 1.2(s, 12H).

[0291] Mass: [(M+H) + ] : 500

[0292]

[0293] [Preparation Example 6]

[0294] <Step 1> Synthesis of 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan

[0295]

[0296] 50 g (186.9 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 41.6 g (196.2 mmol) of dibenzo[b,d]furan-3-ylboronic acid, 46.5 g (5.6 mmol) of Pd(PPh3), and 77.5 g (560.6 mmol) of K2CO3 were added to 625 ml of THF and 155 ml of H2O, and 56.4 g (85.1% yield) of 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan was obtained using the same method as in Step 1 of Preparation Example 1.

[0297] 1H-NMR: δ 8.07(s, 2H), 8.03 (d, 1H), 7.82 (d, 2H), 7.98 (d, 1H) 7.75 (m, 3H), 7.54 (d, 1H), 7.49 (t, 2H), 7.39 (m, 2H), 7.31 (t, 1H).

[0298] Mass: [(M+H) + ] : 355

[0299] <Step 2> Synthesis of Core6

[0300]

[0301] 56.4 g (159.0 mmol) of 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b,d]furan, 52.5 g (206.7 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 34.4 g (4.7 mmol) of Pd2(dba), 46.8 g (477.1 mmol) of KOAc, and 4.5 g (9.5 mmol) of Xphos were added to 530 ml of 1,4-Dioxane, and 56.7 g (yield 79.9%) of Core6 was obtained using the same method as the Core1 synthesis method of Preparation Example 1.

[0302] 1H-NMR: δ 8.07(s, 2H), 8.03 (d, 1H), 7.82 (d, 2H), 7.98 (d, 1H) 7.75 (m, 3H), 7.54 (d, 1H), 7.49 (t, 2H), 7.39 (m, 2H), 7.31 (t, 1H) 1.2(s, 12H).

[0303] Mass: [(M+H) + ] : 447

[0304]

[0305] [Synthesis Example 1] Synthesis of Compound 1

[0306]

[0307] 15.0 g (1eq, 29.5mmol) of 4-(4-chlorophenyl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine, 13.4 g (1.05eq, 30.9 mmol) of Core3 from [Preparation Example 3], 20.2 g (0.03eq, 0.9 mmol) of Pd(OAc), 28.8 g (3.0eq, 88.2 mmol) of Cs2CO3, and 0.8 g (0.06eq, 1.8 mmol) of Xphos were added to 100ml of toluene, 25ml of EtOH, and 25ml of H2O, and heated under reflux for 12 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 15.8 g (yield 68.8%) of compound 1.

[0308] Mass: [(M+H) + ] : 779

[0309]

[0310] [Synthesis Example 2] Synthesis of Compound 2

[0311]

[0312] 15.0 g (1eq, 29.5mmol) of 4-(3-chlorophenyl)-6-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-phenylpyrimidine, 11.0 g (1.05eq, 30.9mmol) of 2-([1,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 20.2 g (0.03eq, 0.9 mmol) of Pd(OAc), 28.8 g (3.0eq, 88.2 mmol) of Cs2CO3, and 0.8 g (0.06eq, 1.8 mmol) of Xphos were added to 100ml of toluene, 25ml of EtOH, and 25ml of H2O, and the mixture was heated and refluxed for 12 hours to react. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 12.7 g of compound 2 (yield 61.3%).

[0313] Mass: [(M+H) + ] : 703

[0314]

[0315] [Synthesis Example 3] Synthesis of Compound 3

[0316]

[0317] 15.0 g (25.6 mmol) of 4-(3-chlorophenyl)-2-phenyl-6-(4-(1-phenyldibenzo[b,d]furan-4-yl)phenyl)pyrimidine, 11.6 g (1.05 eq, 26.9 mmol) of Core1 from [Preparation Example 1], 20.2 g (0.03 eq, 0.8 mmol) of Pd(OAc), 25.1 g (3.0 eq, 76.9 mmol) of Cs2CO3, and 0.8 g (0.06 eq, 1.5 mmol) of Xphos were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and the mixture was heated under reflux for 12 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 12.7 g (yield 57.9%) of compound 3.

[0318] Mass: [(M+H) + ] : 855

[0319]

[0320] [Synthesis Example 4] Synthesis of Compound 12

[0321]

[0322] 15.0 g (26.8 mmol) of 2-(4-chlorophenyl)-4-(4-(naphtho[2,1-b]benzofuran-8-yl)phenyl)-6-phenyl-1,3,5-triazine, 12.2 g (1.05 eq, 28.1 mmol) of Core1 of [Preparation Example 1], 20.2 g (0.03 eq, 0.8 mmol) of Pd(OAc), 26.2 g (3.0 eq, 80.3 mmol) of Cs2CO3, and 0.8 g (0.06 eq, 1.6 mmol) of Xphos were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and the mixture was heated and refluxed for 12 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 18.5 g (yield 83.2%) of compound 12.

[0323] Mass: [(M+H) + ] : 830

[0324]

[0325] [Synthesis Example 5] Synthesis of Compound 16

[0326]

[0327] 4'-(4-(4-(benzo[b]naphtho[2,1-d]thiophen-9-yl)phenyl)-6-(3-chlorophenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile 10.0 g (1eq, 14.8 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 4.25 g (1.05eq, 15.5 mmol), Pd(OAc)20.1 g (0.03eq, 0.44 mmol), Cs2CO3 14.43 g (3.0eq, 44.3 mmol), Xphos 0.42 Add g (0.06eq, 0.9 mmol) to 130ml of Toluene, 30ml of EtOH, and 30ml of H2O. The reaction was carried out by heating and refluxing for 8 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 5.7 g (yield 44.3%) of compound 16.

[0328] Mass: [(M+H) + ] : 871

[0329]

[0330] [Synthesis Example 6] Synthesis of Compound 20

[0331]

[0332] 4-(3-chlorophenyl)-2-(4-(9-(naphthalen-1-yl)dibenzo[b,d]furan-3-yl)phenyl)-6-phenylpyrimidine 15.0 g (1eq, 23.6 mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3'''-(trifluoromethyl)-[1,1':3',1'':3'',1'''-quaterphenyl]-3-carbonitrile 13.0 g (1.05eq, 24.8 mmol), Pd(OAc)20.16 g (0.03eq, 0.7 mmol), CsCO3 23.1 g (3.0eq, 70.8 mmol), Xphos 0.68 g (0.06eq, 1.43 mmol) was added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and heated and refluxed for 8 hours to react. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 12.1 g (yield 51.3%) of compound 20.

[0333] Mass: [(M+H) + ] : 988

[0334]

[0335] [Synthesis Example 7] Synthesis of Compound 23

[0336]

[0337] 2-(3-(4-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-3-yl)phenyl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine 15.8 g (1eq, 23.9 mmol), 2-([1,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 8.94 g (1.05eq, 25.1 mmol), Pd(OAc)20.16 g (0.03eq, 0.7 mmol), Cs2CO323.4 g (3.0eq, 71.7 mmol) and 0.68 g (0.06eq, 1.43 mmol) of Xphos were mixed with 100ml of Toluene and EtOH. 25 ml of the compound was added to 25 ml of H2O and heated under reflux for 8 hours to react. After completion of the reaction, it was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 13.4 g of compound 23 (yield 65.5%).

[0338] Mass: [(M+H) + ] : 856

[0339]

[0340] [Synthesis Example 8] Synthesis of Compound 25

[0341]

[0342] 15.0 g (1eq, 28.0 mmol) of 4-(7-(4-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)dibenzo[b,d]furan-3-yl)benzonitrile, 14.97 g (1.05eq, 29.4 mmol) of Core2 from [Preparation Example 2], 40.97 g (0.03eq, 0.8 mmol) of Pd(pph3), and 11.6 g (3.0eq, 84.1 mmol) of K2CO3 were added to 105 ml of 1,4dioxane and 35 ml of H2O, and the mixture was heated under reflux for 6 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 15.5 g (yield 62.7%) of compound 25.

[0343] Mass: [(M+H) + ] : 881

[0344]

[0345] [Synthesis Example 9] Synthesis of Compound 28

[0346]

[0347] 4-(4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)phenyl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidin 15.0 g(1eq, 23.03 mmol), Core3 10.5 g(1.05eq, 24.19 mmol) of [Preparation Example 3], Pd(OAc) 20.16 g(0.03eq, 0.7 mmol), Cs2CO3 22.5 g(3.0eq, 69.1 mmol), Xphos 0.66 g(0.06eq, 1.4 mmol) were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and reacted by heating and refluxing for 8 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 16.25 g (yield 76.6%) of compound 28.

[0348] Mass: [(M+H) + ] : 921.17

[0349]

[0350] [Synthesis Example 10] Synthesis of Compound 36

[0351]

[0352] 2-(3-(benzo[b]naphtho[1,2-d]thiophen-5-yl)phenyl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 15.0 g(26.1 mmol), Core4 13.7 g(1.05eq, 27.3 mmol) of [Preparation Example 4], Pd(OAc) 20.2 g(0.03eq, 0.8 mmol), Cs2CO3 25.5 g(3.0eq, 78.1 mmol), Xphos 0.7 g(0.06eq, 1.6 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and the mixture was heated under reflux for 8 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 16.4 g (yield 68.91%) of compound 36.

[0353] Mass: [(M+H) + ] : 914

[0354]

[0355] [Synthesis Example 11] Synthesis of Compound 37

[0356]

[0357] 9-(2'-(4-(3-chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)naphtho[2,1-b]benzofuran-5-ylium 15.0 g (23.6 mmol), Core1 10.7 g (1.05 eq, 24.8 mmol) of [Preparation Example 1], Pd(OAc) 20.2 g (0.03 eq, 0.7 mmol), Cs2CO3 23.1 g (3.0 eq, 70.8 mmol), Xphos 0.7 g (0.06 eq, 1.4 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted by heating and refluxing for 12 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 14.8 g (yield 69.16%) of compound 37.

[0358] Mass: [(M+H) + ] : 906

[0359]

[0360] [Synthesis Example 12] Synthesis of Compound 49

[0361]

[0362] 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-(3-(naphtho[2,1-b]benzofuran-5-yl)phenyl)pyrimidine 15.0 g(1eq, 21.1 mmol), [[1,1':3',1''-terphenyl]-5'-ylboronic acid 6.1 g(1.05eq, 22.1 mmol), Pd(OAc) 20.14 g(0.03eq, 0.6 mmol), Cs2CO3 20.6 g(3.0eq, 63.3 mmol), Xphos 0.6 g(0.06eq, 1.8 mmol) were added to 130 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and heated under reflux for 10 hours. The reaction was carried out by stirring. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtering was performed. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 12.4 g (yield 64.9%) of compound 49.

[0363] Mass: [(M+H) + ] : 905.

[0364]

[0365] [Synthesis Example 13] Synthesis of Compound 50

[0366]

[0367] 2-(4-(4-(3-chlorophenyl)-6-phenylpyrimidin-2-yl)phenyl)-5-phenyl-5H-benzo[b]carbazole 15.0 g(23.65 mmol) ), Core1 10.7 g(1.05eq, 24.8 mmol) of [Preparation Example 1], Pd(OAc) 20.2 g(0.03eq, 0.7 mmol), Cs2CO3 23.1 g(3.0eq, 70.8 mmol), Xphos 0.7 g(0.06eq, 1.4 mmol) were added to 100 ml of toluene, 25 ml of EtOH, and 25 ml of H2O, and reacted by heating and refluxing for 12 hours. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 12.4 g (yield 57.9%) of compound 50.

[0368] Mass: [(M+H) + ] : 904

[0369]

[0370] [Synthesis Example 14] Synthesis of Compound 65

[0371]

[0372] 15.0 g (24.6 mmol) of 4-(4-chloronaphthalen-1-yl)-6-(3-(naphtho[1,2-b]benzofuran-10-yl)phenyl)-2-phenylpyrimidine, 11.2 g (1.05 eq, 25.9 mmol) of Core5 of [Preparation Example 5], 20.17 g (0.03 eq, 0.7 mmol) of Pd(OAc), 24.1 g (3.0 eq, 73.9 mmol) of Cs2CO3, and 0.7 g (0.06 eq, 1.5 mmol) of Xphos were added to 130 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and the mixture was heated under reflux for 8 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 14.4 g of compound 65 (yield 66.5%).

[0373] Mass: [(M+H) + ] : 879

[0374]

[0375] [Synthesis Example 15] Synthesis of Compound 67

[0376]

[0377] 2-(4-chlorophenyl)-4-(3-(7,8-diphenyldibenzo[b,d]furan-3-yl)phenyl)-6-phenylpyrimidine 15.0 g(22.7 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 6.53 g(1.05eq, 23.8 mmol), Pd(OAc) 20.15 g(0.03eq, 0.7 mmol), Cs2CO3 21.6 g(3.0eq, 68.1 mmol), Xphos 0.7 g(0.06eq, 1.4 mmol) were added to 130 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and heated under reflux for 10 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 13.5 g of compound 67 (yield 69.6%).

[0378] Mass: [(M+H) + ] : 855

[0379]

[0380] [Synthesis Example 16] Synthesis of Compound 77

[0381]

[0382] 15 g (26.8 mmol) of 2-(4-chlorophenyl)-4-(3-(naphtho[1,2-b]benzofuran-9-yl)phenyl)-6-phenyl-1,3,5-triazine, 12.2 g (1.05 eq, 28.1 mmol) of Core3 from [Preparation Example 3], 20.18 g (0.03 eq, 0.8 mmol) of Pd(OAc), 26.2 g (3.0 eq, 80.4 mmol) of Cs2CO3, and 0.77 g (0.06 eq, 1.6 mmol) of Xphos were added to 120 ml of toluene, 30 ml of EtOH, and 30 ml of H2O, and the mixture was heated under reflux for 8 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 17.2 g of compound 77 (yield 77.4%).

[0383] Mass: [(M+H) + ] : 830

[0384]

[0385] [Synthesis Example 17] Synthesis of Compound 79

[0386]

[0387] 15.0 g (1eq, 26.8 mmol) of 4-(4-chlorophenyl)-6-(3-(naphtho[2,1-b]benzofuran-10-yl)phenyl)-2-phenylpyrimidine, 12.6 g (1.05eq, 28.2 mmol) of Core6 from [Preparation Example 6], 20.22 g (0.03eq, 0.8 mmol) of Pd(OAc), 26.2 g (3.0eq, 80.5 mmol) of Cs2CO3, and 0.8 g (0.06eq, 1.6 mmol) of Xphos were added to 150 ml of toluene, 40 ml of EtOH, and 40 ml of H2O, and the mixture was heated under reflux for 10 hours to react. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 15.7 g (yield 69.4%) of compound 79.

[0388] Mass: [(M+H) + ] : 843

[0389]

[0390] [Synthesis Example 18] Synthesis of Compound 82

[0391]

[0392] 15.0 g (1eq, 26.8 mmol) of 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-(naphtho[2,1-b]benzofuran-10-yl)pyrimidine, 12.2 g (1.05eq, 28.2 mmol) of 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane, 40.93 g (0.03eq, 0.8 mmol) of Pd(pph3), and 11.1 g (3.0eq, 80.5 mmol) of K2CO3 were added to 105 ml of 1,4dioxane and 35 ml of H2O, and the mixture was heated and refluxed for 5 hours to react. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 14.9 g (yield 66.98%) of compound 82.

[0393] Mass: [(M+H) + ] : 829

[0394]

[0395] [Synthesis Example 19] Synthesis of Compound 83

[0396]

[0397] 15.0 g (1eq, 29.4 mmol) of 2-chloro-4-phenyl-6-(4-(1-phenyldibenzo[b,d]furan-3-yl)phenyl)-1,3,5-triazine, 18.0 g (1.05eq, 30.9 mmol) of 5'-phenyl-3'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)-[1,1':2',1''-terphenyl]-3-carbonitrile, 1.02 g (0.03eq, 0.9 mmol) of Pd(pph3), and 12.2 g (3.0eq, 88.2 mmol) of K2CO3 were added to 105 ml of 1,4dioxane and 35 ml of H2O, and the mixture was heated and refluxed for 6 hours to react. After completion of the reaction, extraction was performed with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallization was performed with toluene acetone to obtain 17.5 g (yield 63.9%) of compound 83.

[0398] Mass: [(M+H) + ] : 931

[0399]

[0400] [Synthesis Example 20] Synthesis of Compound 91

[0401]

[0402] 2-([1,1'-biphenyl]-2-yl)-4-(4-chlorophenyl)-6-(4-(3-phenyldibenzo[b,d]furan-2-yl)phenyl)-1,3,5-triazine 15g (22.7 mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':3',1''-terphenyl]-4-carbonitrile 9.1 g (1.05eq, 23.8 mmol), Pd(OAc)20.15 g (0.03eq, 0.7 mmol), Cs2CO322.1 g (3.0eq, 67.9 mmol) and 0.65 g (0.06eq, 1.4 mmol) of Xphos were added to 120ml of Toluene and EtOH. 30 ml of the resulting mixture was added to 30 ml of H2O and refluxed for 8 hours to allow the reaction to proceed. After completion of the reaction, it was extracted with dichloromethane, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane, and then recrystallized with toluene acetone to obtain 13.7 g of compound 91 (yield 68.6%).

[0403] Mass: [(M+H) + ] : 881

[0404]

[0405] [Reference example]

[0406] The structures of compounds HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2, ET-3, ET-4 and LiQ used in the present examples and comparative examples are as follows.

[0407]

[0408]

[0409]

[0410]

[0411] [Examples 1 to 10] Fabrication of blue fluorescent organic electroluminescent devices

[0412] After each compound synthesized in the above synthetic example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured as follows.

[0413] 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.

[0414] On the ITO transparent electrode prepared as above, HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / ET-1 (50 Å) / each compound of Compounds 12 to 91 in Table 1 below: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) were stacked in that order to fabricate an organic electroluminescent device.

[0415]

[0416] [Comparative Example 1] Fabrication of a Blue Fluorescent Organic Electroluminescent Device

[0417] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET-2 was used instead of compound 1 as the electron transport layer material.

[0418]

[0419] [Comparative Example 2] Fabrication of a Blue Fluorescent Organic Electroluminescent Device

[0420] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET-3 was used instead of compound 12 as the electron transport layer material.

[0421]

[0422] [Comparative Example 3] Fabrication of a Blue Fluorescent Organic Electroluminescent Device

[0423] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET-4 was used instead of compound 12 as the electron transport layer material.

[0424]

[0425] [Evaluation Example 1]

[0426] For each of the blue organic electroluminescent devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 3, the driving voltage, current efficiency, and luminescence peak at a current density of 10 mA / cm2 were measured, and the results are shown in Table 1 below.

[0427] Sample Electron Transport Layer Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 1 Compound 124.14627.3 Example 2 Compound 164.24596.9 Example 3 Compound 204.34616.6 Example 4 Compound 254.34606.6 Example 5 Compound 364.04597.6 Example 6 Compound 494.04587.5 Example 7 Compound 504.54596.4 Example 8 Compound 674.44616.2 Example 9 Compound 834.24587.3 Example 10 Compound 914.24607.2 Comparative Example 1ET-24.84605.8Comparative example 2ET-35.04585.4Comparative example 3ET-44.84605.5

[0428] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 10 using the compounds according to the present invention as electron transport layer materials exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 3 using ET-2 to ET-4, which do not include the composition of the present invention, as electron transport layer materials.

[0429]

[0430] [Examples 11 to 30] Fabrication of blue fluorescent organic electroluminescent devices

[0431] After each compound synthesized in the above synthetic example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured as follows.

[0432] A glass substrate coated with a 1500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0433] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HT-1 + 2% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / BH + 2% BD (200 Å) / compounds 1 to 91 (50 Å) in Table 2 below / ET: LiQ = 1:1 (300 Å) / LiF (10 Å) / Al (1000 Å) in that order.

[0434] The structures of the compounds HT-1, HT-2, HAT-CN, BH, BD, and Liq used at this time are each the same as those described in the reference examples, and the structure of ET is as follows.

[0435]

[0436]

[0437] [Comparative Example 4] Fabrication of a blue fluorescent organic electroluminescent device

[0438] A blue organic electroluminescent device of Comparative Example 4 was manufactured in the same manner as in Example 11, except that ET-1 was used instead of compound 1 as the electron transport auxiliary layer material.

[0439]

[0440] [Comparative Example 5] Fabrication of a blue fluorescent organic electroluminescent device

[0441] A blue organic electroluminescent device of Comparative Example 5 was manufactured in the same manner as in Example 11, except that ET-2 was used instead of compound 1 as the electron transport auxiliary layer material.

[0442]

[0443] [Comparative Example 6] Fabrication of a blue fluorescent organic electroluminescent device

[0444] A blue organic electroluminescent device of Comparative Example 6 was manufactured in the same manner as in Example 11, except that ET-3 was used instead of compound 1 as the electron transport auxiliary layer material.

[0445]

[0446] [Comparative Example 7] Fabrication of a blue fluorescent organic electroluminescent device

[0447] A blue organic electroluminescent device of Comparative Example 7 was manufactured in the same manner as in Example 11, except that ET-4 was used instead of compound 1 as the electron transport auxiliary layer material.

[0448]

[0449] [Evaluation Example 2]

[0450] For the organic electroluminescent devices manufactured in Examples 11 to 30 and Comparative Examples 4 to 7, the driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0451] Sample Electron Transport Auxiliary Layer Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 11 Compound 14.04607.0 Example 12 Compound 24.04597.0 Example 13 Compound 34.14616.8 Example 14 Compound 123.84607.4 Example 15 Compound 164.24606.8 Example 16 Compound 204.14606.9 Example 17 Compound 234.24606.6 Example 18 Compound 254.24596.8 Example 19 Compound 284.34616.7 Example 20 Compound 364.24596.9 Example 21 Compound 374.04616.9 Example 22 Compound 493.94617.1 Example 23 Compound 504.04607.0 Example 24 Compound 654.24586.7 Example 25 Compound 673.94617.3 Example 26 Compound 774.14626.7 Example 27 Compound 793.94617.2 Example 28 Compound 824.04596.7 Example 29 Compound 834.24606.9 Example 30 Compound 914.14606.8 Comparative Example 4ET-14.94616.0 Comparative Example 5ET-24.64606.2 Comparative Example 6ET-34.84605.8Comparative example 7ET-44.84606.0

[0452] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 11 to 30 including the compound according to the present invention as an electron transport auxiliary layer material exhibited superior performance in terms of current efficiency and driving voltage compared to the blue organic electroluminescent devices of Comparative Examples 4 to 7 using ET-1 to ET-4, which do not include the composition of the present invention, as an electron transport auxiliary layer material, respectively.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The plurality of Xs are identical or different, and are each independently CR5 or N, provided that at least two of the plurality of Xs are N, R1 is C1~C 40 Alkyl group of C3~C 40 Cycloalkyl group of C6~C 60 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, or may be combined with any adjacent group to form a condensed ring, a is an integer greater than or equal to 1, and when a is greater than or equal to 2, multiple R1s are identical or different. L1 and L2 are identical or different, and are each independently C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, m is an integer from 1 to 3, n is an integer from 0 to 3, Ar2 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , 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 C3~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, C6~C 60Arylamine group of C5~C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, Ar1 is a moiety represented by the following chemical formula 2, [Chemical formula 2] In the above chemical formula 2, * is connected to chemical formula 1, Y is O, S or NR4, Ring A and ring B are the same or different from each other, and each independently contains or does not contain a heteroatom C5~C 18 It is a monocyclic or polycyclic hydrocarbon ring group, R2 to R5 are the same or different and each independently represents 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 of , 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 C3~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, C6~C 60 Arylamine group of C5~C 60 is selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, or can form a condensed ring by combining with any adjacent group; b is an integer from 0 to 3, c is an integer from 0 to 4, The arylene group, heteroarylene group of the above L1~L2; the aryl group, heteroaryl group of the above R1, 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 R2~R5 and Ar2 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 of, 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, C6~C 60 Arylamine group of C5~C 60 The compound may be substituted with at least one substituent selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms, and when there are multiple substituents, they may be the same or different from each other.

2. In paragraph 1, R1 is C6~C 30 is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, a is an integer from 1 to 5, and when a is 2 to 5, multiple R1s are the same or different from each other. (R1) substituted or unsubstituted with a substituent a A compound containing at least 18 total carbon atoms.

3. In paragraph 1, The above Y-containing ring is a compound selected from a group of substituents represented by the following chemical formula: In the above formula, * indicates a part connected to the chemical formula 1 above, Ring D is the same or different from each other, and each independently represents a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom, Y, R 2, R3, b and c are as defined in paragraph 1, respectively.

4. In paragraph 1, The above Y-containing ring is a compound selected from a group of substituents represented by the following chemical formula: In the above formula, * indicates a part connected to the chemical formula 1 above, R4 is as defined in paragraph 1.

5. In paragraph 1, The above X-containing ring is a compound selected from the group of substituents represented by the following structural formula: In the above formula, * indicates a part connected to the chemical formula 1 above, Ar1~Ar2, R5, L1, and m are each as defined in Article 1.

6. In paragraph 1, Ar2 is C6~C 60A compound selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

7. In paragraph 1, Ar2 is a compound selected from a group of substituents represented by the following chemical formula. In the above formula, * indicates a part connected to the chemical formula 1 above, R 11 Silver hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms.

8. In paragraph 1, L1 and L2 are the same or different from each other, and are each independently a compound selected from the following structural formulas: In the above formula, * indicates a part connected to the chemical formula 1 above, R 12 is hydrogen, deuterium (D), C1~C 40 Alkyl group of C6~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclear atoms.

9. In paragraph 1, The compound represented by the chemical formula 1 above is a compound represented by any one of the following chemical formulas 3 to 6: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] In the above formula, A, B, Y, Ar2, L1-L2, R1~R3, a~c, m and n are each as defined in Article 1.

10. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 7 to 15: [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] In the above formula, Ring D is a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom, X, Y, Ar2, L1-L2, R1~R3, a~c, m and n are as defined in Article 1, respectively.

11. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 16 to 18: [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] In the above formula, Z is O or S, Ring E is a divalent aromatic condensed polycyclic group, A, B, X, Y, Ar2, L2, R1~R3, a~c, m and n are each as defined in Article 1.

12. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 19 or chemical formula 20: [Chemical Formula 19] [Chemical formula 20] In the above formula, n is an integer from 1 to 3, A, B, X, Y, Ar2, R1~R3, a~c, and m are each as defined in Article 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 21 to 32: [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] In the above formula, Ring D is a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom, A, B, X, Y, Ar2, L1~L2, R1~R3, b~c, m and n are each as defined in Article 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 120.

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 15.

17. In paragraph 16, An organic electroluminescent device, wherein the organic layer including the compound is 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 life-span improvement layer, an electron transport layer, and an electron transport auxiliary layer.

18. In paragraph 16, An organic electroluminescent device in which the compound is included as at least one material among a phosphorescent host material of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

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