Organic compound and organic electroluminescent device using same

Abstract

The present invention relates to a novel compound having excellent carrier transport capability, light emission capability, and thermal stability, and an organic electroluminescent device having improved characteristics such as light emission efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers, and to an organic electroluminescent device.

Description

Technical Field

[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 and an organic electroluminescent device. The compound has excellent electron transport capability, and the organic electroluminescent device improves the luminous efficiency, driving voltage, life and other characteristics by including the compound in more than one organic layer. Background Art

[0002] Starting from Bernanose's observation of organic thin film luminescence in the 1950s, the research on organic electroluminescent devices using blue electroluminescence of anthracene single crystals developed in 1965, and Tang proposed an organic electroluminescent device with a stacked structure of functional layers divided into a hole layer and a light-emitting layer in 1987. Then, in order to prepare high-efficiency and long-life organic electroluminescent devices, it developed into a form of introducing various characteristic organic layers into the device, thereby developing special substances for this purpose.

[0003] For an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground state, light is emitted. In this case, the substances used as the organic layer can be divided into luminescent substances, hole injection substances, hole transport substances, electron transport substances, electron injection substances, etc. according to their functions.

[0004] The light-emitting layer materials of organic electroluminescent devices can be divided into blue, green, and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting substances are also used as light-emitting materials to achieve better natural colors. In addition, in order to increase the color purity and the luminous efficiency through energy transfer, a host / dopant system can be used as a light-emitting material. The above-mentioned doping substances can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Compared with fluorescence, the development of such phosphorescent materials can theoretically increase the luminous efficiency by up to 4 times, so not only phosphorescent dopants, but also phosphorescent host materials have attracted much attention. So far, it is well known that NPB, BCP, Alq3, etc. are substances used in hole injection layers, hole transport layers, hole group faults, and electron transport layers, and as light-emitting substances, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, metal coordination compounds containing Ir, such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc., are used as phosphorescent materials that have great advantages in improving efficiency among luminescent materials as blue, green, and red doping materials. So far, CBP has shown excellent properties as a phosphorescent host material.

[0005] However, existing luminescent materials have advantages in luminescent properties, but due to low glass transition temperature and very poor thermal stability, they cannot achieve a satisfactory level in terms of the life of organic electroluminescent devices. Therefore, it is necessary to develop luminescent materials with excellent properties. Summary of the invention

[0006] Technical issues

[0007] The present invention can be applied to organic electroluminescent devices, and the technical problem is to provide a novel organic compound with excellent hole and electron injection and transport capabilities, luminescence capabilities, etc.

[0008] And, another technical problem of the present invention is to provide an organic electroluminescent device with improved lifespan, which exhibits low driving voltage and high luminous efficiency by including the above-mentioned novel organic compound.

[0009] Other objects and advantages of the present invention can be explained in more detail through the following detailed description of the invention and the scope of protection of the invention.

[0010] Technical Solution

[0011] In order to achieve the above object, the present invention provides a compound as shown in the following Chemical Formula 1.

[0012] Chemical formula 1:

[0013]

[0014] In the above chemical formula 1,

[0015] Multiple Xs are the same as or different from each other and are each independently CR5 or N, but at least 2 of the multiple Xs are N,

[0016] Ar1 is selected from C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The group consisting of arylheteroarylamine groups and heteroarylamine groups having 5 to 60 nuclear atoms,

[0017] Y is O, S or NR4,

[0018] Ring A and Ring B are the same or different from each other, and are each independently C5 to C5 containing or not containing heteroatoms. 18 A monocyclic or polycyclic hydrocarbon ring group, but at least one of the rings A and B is C 10 ~C 18 A polycyclic hydrocarbon ring group,

[0019] R2 to R3 are the same or different from each other and are independently selected from deuterium, C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The group consisting of aryl heteroaryl amine groups and heteroaryl amine groups having 5 to 60 nuclear atoms, or they can combine with adjacent groups to form a condensed ring;

[0020] R4 to R5 are the same or different from each other and are independently selected from hydrogen, deuterium, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The group consisting of aryl heteroaryl amine groups and heteroaryl amine groups having 5 to 60 nuclear atoms;

[0021] L can be selected from C6~C 18 The group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0022] R1 is selected from C6~C 60 The group consisting of an aryl group, an arylsilyl group and a heteroaryl group having 5 to 60 nuclear atoms,

[0023] m is an integer greater than or equal to 1, n is an integer from 0 to 3,

[0024] a is an integer from 0 to 2, b is an integer from 0 to 4,

[0025] The arylene group and heteroarylene group of L; the aryl group, heteroaryl group and arylsilyl group of R1; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboryl group, arylboryl group, arylphosphino group, arylphosphine oxide group and arylamine group of R2 to R5 and Ar1 can be independently selected from hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Aromatic amine group, C5~C 60 and heteroarylamine groups having 5 to 60 nuclear atoms, in which case, when there are a plurality of such substituents, they may be the same as or different from each other,

[0026] However, the total number of carbon atoms contained in the ring containing Y, which may be substituted or unsubstituted, is at least 16.

[0027] Furthermore, the present invention provides an organic electroluminescent device, which includes an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers contains the compound shown in the above chemical formula 1.

[0028] The organic layer containing the compound shown in the above chemical formula 1 can 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 improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound shown in chemical formula 1 can be included as a material of at least one of the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0029] Effects of the Invention

[0030] According to an embodiment of the present invention, since the compound represented by the above Chemical Formula 1 has excellent electron transport capability, luminescence capability, heat resistance, etc., it can be used as an organic layer material of an organic electroluminescent device.

[0031] In particular, when the compound of the present invention as shown in Chemical Formula 1 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 existing host materials or electron transport materials.

[0032] Therefore, the organic electroluminescent device including the compound represented by the above Chemical Formula 1 can be significantly improved in terms of excellent luminescent properties, low driving voltage, long life and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0033] The effects of the present invention are not limited to the contents of the above examples, and more various effects are included in this specification. DETAILED DESCRIPTION

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

[0035] <New organic compounds>

[0036] The invention provides a novel aromatic compound having excellent thermal stability, carrier transport capability, luminescence capability and the like.

[0037] Specifically, the novel organic compound of the present invention is a cyclic compound having multiple aromatic groups and non-shared electron pairs, for example, including a dibenzo / carbazole part, and is combined with an electron withdrawing group (EWG) having excellent electron transporting ability to form a basic skeleton.

[0038] The compound of this structure as shown in Chemical Formula 1 is centered on an azine group (e.g., triazine, pyrimidine, etc.) as one of the EWG groups, which replaces a cyclic compound having a non-shared electron pair and a plurality of aromatic groups, resulting in an increase in the electron density of the EWG having electron transport capability in the structure, thereby further improving the electron transport capability compared to the existing known material structure, thereby showing an effect of increasing efficiency. In addition, due to the rigid chemical structure of the cyclic compound such as a dibenzo- or carbazole-type cyclic compound combined with the EWG, it has an excellent high glass transition temperature (Tg) and thermal stability.

[0039] Moreover, the compound shown in the above chemical formula 1 forms a polycyclic structure by fusing the cyclic compound and the aromatic group combined with the EWG, so that the electrical stability of the molecule can be increased, thereby making the device have a higher device life than the prior art. Generally, when the cyclic compound with electron-donating ability is directly combined with the EWG, the HOMO and LUMO orbits are mainly formed in the cyclic compound and are concentratedly electrically damaged, so the possibility of reducing the life of the device is high. In order to solve this problem, in the present invention, the stability of the molecule can be significantly increased by having a heterocyclic structure (for example, a ring containing Y) of a cyclic compound and an aromatic group fused with an electron-donating ability such as a dibenzo part. In addition, in order to increase the electron transfer rate, by introducing triazines or pyrimidines as functional groups with strong electron-withdrawing ability, it is possible to have physical and chemical properties that are more suitable for electron injection and electron transport.

[0040] Furthermore, the compound shown in Chemical Formula 1 of the present invention has a higher triplet energy than the light-emitting layer, so that the excitons generated in the light-emitting layer can be prevented from diffusing (transferring) to the adjacent electron transport layer or hole transport layer. Therefore, the luminous efficiency of the device can be improved by increasing the number of excitons that contribute to luminescence in the light-emitting layer, and the life of the device can be effectively increased by improving the durability and stability of the device. Most of the developed materials can be driven at low voltage, and therefore exhibit physical properties with improved lifespan.

[0041] As described above, when the compound of the present invention as shown in Chemical Formula 1 is used as an organic material layer of an organic electroluminescent device, preferably a light-emitting layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer material, a luminescent auxiliary layer material, and a life improvement layer material, the performance and life characteristics of the organic electroluminescent device can be significantly improved. Such an organic electroluminescent device can ultimately maximize the performance of a full-color organic light-emitting panel.

[0042] The compound represented by Chemical Formula 1 of the present invention forms a basic skeleton by combining a cyclic compound condensed with an electron withdrawing group (EWG) having excellent electron transporting ability and a plurality of aromatic groups.

[0043] The compound of the present invention as shown in Chemical Formula 1 is formed by combining an electron withdrawing group (EWG) having excellent electron transport ability such as a nitrogen-containing heterocycle (e.g., a ring containing X) with a cyclic compound (e.g., a ring containing Y) and multiple aromatic groups (e.g., a ring containing R1) to form a basic skeleton.

[0044] The nitrogen-containing heterocyclic ring (e.g., a ring containing X) is a monocyclic nitrogen-containing heteroaryl group containing at least two nitrogen atoms. As an embodiment of the nitrogen-containing heteroaryl ring (e.g., a ring containing X), multiple Xs are the same or different from each other, and each is independently N or CR5, but at least 2 of the multiple Xs are N. As a specific example, the multiple Xs contain 2 to 3 Ns, preferably 3 Ns. As described above, by containing a heterocyclic ring containing 2 to 3 nitrogen atoms, a more excellent electron-withdrawing property is exhibited, which is beneficial to electron injection and transport.

[0045] Wherein, R5 can be selected from hydrogen, deuterium, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 and heteroarylamine groups having 5 to 60 nuclear atoms. Specifically, R5 is preferably selected from the group consisting of hydrogen, deuterium, C1 to C 40 Alkyl, C6~C 60 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0046] As a specific example, the compound represented by Chemical Formula 1 including the nitrogen-containing heterocyclic ring (ring containing X) can be specifically represented by Chemical Formulas 2 to 5 below.

[0047] Chemical formula 2:

[0048]

[0049] Chemical formula 3:

[0050]

[0051] Chemical formula 4:

[0052]

[0053] Chemical formula 5:

[0054]

[0055] In the above formula,

[0056] A, B, Y, L, R1 to R3, Ar1, a, b, m and n are respectively defined as in Chemical Formula 1.

[0057] In the nitrogen-containing heterocyclic ring (ring containing X) of the present invention, the ring containing Y as a ring compound and Ar1 may be substituted as various substituents. Such Ar1 may be selected from C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 Ar1 can be selected from the group consisting of C6 to C 60 and heteroaryl groups having 5 to 60 nuclear atoms, more specifically, preferably C6 to C 18 The aryl group and the heteroaryl group having 5 to 18 nuclear atoms.

[0058] A specific example of Ar1 is as shown in the following structural formula.

[0059]

[0060] In the above formula,

[0061] * indicates a site of connection with the above Chemical Formula 1.

[0062] Also, the ring compound introduced into the nitrogen-containing heterocyclic ring (ring containing X) may be represented by the ring containing Y of Chemical Formula 1, specifically a fused polycyclic heterocyclic structure in which a dibenzo / carbazole moiety is fused with a conventional aromatic group.

[0063] As a specific example, in the ring containing Y, Y is O, S or NR4.

[0064] Wherein, R4 can be selected from hydrogen, deuterium, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 Specifically, R4 is preferably selected from the group consisting of C6 to C 30 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

[0065] Furthermore, ring A and ring B may be the same or different from each other, and may be independently C5 to C6 containing or not containing heteroatoms. 18 However, at least one of the above rings A and B has C 10 ~C 18 The ring A and the ring B may be independently a condensed or fused polycyclic hydrocarbon ring or a nitrogen-containing ring known in the art, for example, a polycyclic alicyclic ring, a polycyclic heteroalicyclic ring, a polycyclic aromatic ring or a polycyclic heteroaromatic ring. Preferably, it may be a polycyclic aromatic ring having 10 to 18 carbon atoms or a polycyclic heteroaromatic ring containing heteroatoms having 10 to 12 nuclear atoms. The heteroatoms may be N, O or S.

[0066] R2 and R3 are the same or different from each other and are independently selected from deuterium, C1-C 40Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The present invention is preferably selected from the group consisting of aryl heteroaryl amine groups and heteroaryl amine groups having 5 to 60 nuclear atoms, or they can be combined with adjacent groups to form a conventional monocyclic or polycyclic condensed ring. Specifically, R2 and R3 are preferably each independently selected from C6 to C 60 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

[0067] a is an integer from 0 to 2, and b is an integer from 0 to 4. When a is 0, ring A is not substituted with a substituent and hydrogen exists, and when a is 1 or 2, ring A may have the above-mentioned substituents other than hydrogen. Similarly, when b is 0, ring B has hydrogen, and when b is 1 or 2, ring B may have the above-mentioned substituents.

[0068] However, the ring containing Y may be substituted or unsubstituted by a substituent described below, and as described above, the total number of carbon atoms contained in the substituted and / or unsubstituted ring containing Y is at least 16. Specifically, it may contain 16 to 24 carbon atoms.

[0069] As a specific example of the present invention, the ring containing Y can be further embodied as any one selected from the following structural formulas. However, it is not limited thereto.

[0070]

[0071] * indicates the site of connection with the above chemical formula 1,

[0072] Rings D are the same as or different from each other and are each independently a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom,

[0073] Y, R2, R3, a and b are as defined in Chemical Formula 1, respectively.

[0074] A specific example of the ring containing Y is as shown in the following structural formula.

[0075]

[0076]

[0077]

[0078] In the above formula,

[0079] R4 is as defined in claim 1. Also, although not shown in the above structural formula, it may be substituted with at least one substituent known in the art (for example, the same as the definition of R2 to R3).

[0080] In the compounds of the present invention, the phenyl group substituting the multiple aryl groups (R1) is directly bonded to the nitrogen-containing heterocyclic ring (e.g., the ring containing X) (n=0) or connected through a separate linker (e.g., L). As described above, when the linker (L) is present, the HOMO-LUMO distribution can be facilitated by expanding the HOMO region, and the charge transfer efficiency can be improved by appropriate overlap of HOMO-LUMO.

[0081] The linker (eg, L) is not particularly limited and can be a conventional divalent group linker known in the art. Specifically, L can be selected from C6 to C 18 More specifically, they can be independently selected from the group consisting of C6-C12 arylene groups and heteroarylene groups having 5 to 12 nuclear atoms.

[0082] Specific examples of the above-mentioned arylene linker and heteroarylene linker include phenylene, biphenylene, naphthylene, anthrylene, indenylene, pyranylene, carbazolylene, thienylene, indolylene, purinylene, quinolylene, pyrrolylene, imidazolylene, oxazolylene, thiazolylene, pyridylene, pyrimidylene, dibenzofuran moiety, dibenzothiophene moiety and / or diphenylselenophenophenone moiety. As a further specific example of the above-mentioned linker, phenylene and biphenylene are preferred.

[0083] The compound of the present invention as shown in Chemical Formula 1 includes a plurality of aryl / heteroaryl groups (eg, a ring containing R1) on one side of a nitrogen-containing heterocyclic ring (eg, a ring containing X).

[0084] Specifically, R1 can be selected from C6~C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, and C6 to C 60The number (m) of the introduced aryl / heteroaryl / arylsilyl groups may be an integer greater than 1, and preferably, may be 1 to 5.

[0085] As a specific example, R1 is selected from C6 to C 30 aryl, heteroaryl having 5 to 30 nuclear atoms, and C6 to C 60 wherein m is an integer from 2 to 5, and (R1) is substituted or unsubstituted with a substituent. m The total number of carbon atoms contained in is at least 18. More specifically, R1 is C6 to C 18 Aryl or C6~C 24 wherein m is an integer of 3 to 5, and the total number of carbon atoms contained in R1 which may be substituted or unsubstituted by a substituent described below may be 18 to 36 carbon atoms.

[0086] In the above chemical formula 1, the arylene group and heteroarylene group of L; the aryl group, heteroaryl group and arylsilyl group of R1; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboryl group, arylboryl group, arylphosphine group, arylphosphine oxide group and arylamine group of R2 to R5 and Ar1 can be independently selected from hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Aromatic amine group, C5~C 60 The substituent may be substituted with one or more substituents selected from the group consisting of an arylheteroarylamine group and a heteroarylamine group having 5 to 60 nuclear atoms. In this case, when a plurality of the substituents are present, they may be the same as or different from each other.

[0087] According to one embodiment of the present invention, according to the type of the linker (L) and the cyclic compound having a non-shared electron pair (ring containing Y), specifically, the dibenzo / carbazole part, the compound shown in the above Chemical Formula 1 can be further specified as any one of the following Chemical Formulas 6 to 13. However, it is not limited thereto.

[0088] Chemical formula 6:

[0089]

[0090] Chemical formula 7:

[0091]

[0092] Chemical formula 8:

[0093]

[0094] Chemical formula 9:

[0095] Chemical formula 10:

[0096] Chemical formula 11:

[0097]

[0098] Chemical formula 12:

[0099]

[0100] Chemical formula 13:

[0101]

[0102] In the above formula,

[0103] Ring D is a monocyclic or polycyclic hydrocarbon ring group which may contain heteroatoms,

[0104] X, Y, R1 to R3, Ar1, a, b, m and n are as defined in Chemical Formula 1, respectively.

[0105] The compounds shown in the above chemical formulas 9 to 11 have a structure in which a polycyclic condensed ring (e.g., D) is arranged adjacent to an azinyl group, and in the compounds shown in chemical formulas 6 to 8, the polycyclic condensed ring (e.g., D) is arranged at a relatively far position from the azinyl group. As described above, when the condensed ring is not adjacent to the azinyl group, the LUMO region is mainly distributed in the azinyl group and does not diffuse uniformly to the condensed ring, thereby exhibiting a fast electron transport capability. Moreover, compared with non-condensed compounds, the conjugation length is increased, so the life of the device can be improved by improving molecular stability.

[0106] According to another embodiment of the present invention, the compound shown in the above Chemical Formula 1 can be further specified as any one of the following Chemical Formulas 14 to 25 according to the number of the multiple aromatic groups (R1) introduced into the molecule and their binding sites. However, it is not limited thereto.

[0107] Chemical formula 14:

[0108]

[0109] Chemical formula 15:

[0110]

[0111] Chemical formula 16:

[0112]

[0113] Chemical formula 17:

[0114] Chemical formula 18:

[0115] Chemical formula 19:

[0116] Chemical formula 20:

[0117] Chemical formula 21:

[0118] Chemical formula 22:

[0119] Chemical formula 23:

[0120] Chemical formula 24:

[0121]

[0122] Chemical formula 25:

[0123]

[0124] In the above formula,

[0125] X, Y, A, B, Ar1, L, R1-R3, a, b and n are respectively defined as in Chemical Formula 1.

[0126] The compound represented by Chemical Formula 1 of the present invention described above can be further embodied as the compounds exemplified below, for example, compounds represented by 1 to 108. However, the compound represented by Chemical Formula 1 of the present invention is not limited to the compounds exemplified below.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and may include, but is not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc.

[0135] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. For example, it may include vinyl, allyl, isopropenyl, 2-butenyl, etc., but is not limited thereto.

[0136] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. For example, it may include ethynyl, 2-propynyl, etc., but is not limited thereto.

[0137] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 40 carbon atoms. In addition, it may also include a form in which two or more rings are simply attached (pendant) or fused to each other. Examples of such aryl groups may include phenyl, naphthyl, phenanthrenyl, anthracenyl, etc., but are not limited thereto.

[0138] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S or Se. In addition, it may include a form in which two or more rings are simply attached (pendant) or fused to each other, and further, it may include a form fused with an aromatic group. Examples of such heteroaryl groups include 6-membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings, such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0139] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and the above R refers to an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, diphenoxy, etc., but are not limited thereto.

[0140] In the present invention, "alkoxy" is a monovalent substituent represented by R'O-, wherein R' refers to an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, and the like.

[0141] In the present invention, "arylamine" refers to an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0142] 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 cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

[0143] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 core atoms, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyls include morpholine, piperazine, etc., but are not limited thereto.

[0144] In the present invention, an "alkylsilyl group" refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and an "arylsilyl group" refers to a silyl group substituted by an aryl group having 5 to 40 carbon atoms.

[0145] In the present invention, the "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring or a combination thereof.

[0146] <Electron Transport Layer Materials>

[0147] The present invention provides an electron transport layer, which comprises the compound shown in the above chemical formula 1.

[0148] The electron transport layer (ETL) plays a role of transferring electrons injected from the cathode to an adjacent layer, specifically, a light-emitting layer.

[0149] The compound as shown in the above Chemical Formula 1 can be used alone as an electron transport layer (ETL) material, or can be mixed with an electron transport layer material known in the art, preferably used alone.

[0150] The electron transport layer material that can be mixed with the compound of the above chemical formula 1 includes electron transport substances generally known in the art. Non-limiting examples of electron transport substances that can be used include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (for example: Alq3 (tris (8-hydroxyquinoline) -aluminum (tris (8-quinolinolato) -aluminium), BAlq, SAlq, Almq3), gallium complexes (for example: Gaq'2OPiv, Gaq'2OAc, 2 (Gaq'2)), etc. They can be used alone or mixed with two or more.

[0151] In the present invention, when the compound of the above Chemical Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within a range known in the art.

[0152] <Electron Transport Assisting Layer Materials>

[0153] Furthermore, the present invention provides an electron transport auxiliary layer, which includes the compound shown in the above Chemical Formula 1.

[0154] The electron transport layer is disposed between the light emitting layer and the electron transport layer, and plays a role in preventing excitons or holes generated in the light emitting layer from diffusing to the electron transport layer.

[0155] The compound as shown in the above Chemical Formula 1 can be used alone as an electron transport auxiliary layer material, or can be mixed with an electron transport layer material known in the art, preferably used alone.

[0156] The electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 includes electron transport substances generally known in the art. For example, the electron transport auxiliary layer can include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (eg, BCP), nitrogen-containing heterocyclic derivatives, and the like.

[0157] In the present invention, when the compound of the above Chemical Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within a range known in the art.

[0158] <Organic electroluminescent device>

[0159] On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device), which comprises the compound represented by Chemical Formula 1 of the present invention.

[0160] Specifically, the present invention is an organic electroluminescent device, which includes an anode, a cathode, and one or more organic layers between the anode and the cathode, and at least one of the one or more organic layers contains a compound as shown in the above chemical formula 1. In this case, the above compounds can be used alone or in combination of two or more.

[0161] The above-mentioned one or more organic layers may be any one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a life-improving layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic layer comprises the compound shown in the above chemical formula 1. Specifically, preferably, the organic layer comprising the compound of the above chemical formula 1 is a light-emitting layer (more specifically, a phosphorescent light-emitting main material), an electron transport layer, and an electron transport auxiliary layer.

[0162] The light-emitting layer of the organic electroluminescent device of the present invention comprises a host material and a dopant material, and in this case, the compound of the above Chemical Formula 1 may be included as the host material. In addition, the light-emitting layer of the present invention may comprise a compound known in the art other than the compound of the above Chemical Formula 1 as the host material.

[0163] When the compound shown in the above chemical formula 1 is included as the light-emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device can be improved because the binding force between holes and electrons in the light-emitting layer is improved. Specifically, preferably, the compound shown in the above chemical formula 1 is included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or doping material. In particular, preferably, the compound shown in the chemical formula 1 of the present invention is a green phosphorescent exciplex N-type host material with a high-efficiency light-emitting layer.

[0164] The structure of the organic electroluminescent device of the present invention is not particularly limited, and may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent 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 luminescence auxiliary layer, the luminescent layer, the electron transport layer, and the electron injection layer may contain a compound as shown in the above chemical formula 1, preferably, the luminescent layer, more preferably, the phosphorescent host may contain a compound as shown in the above chemical formula 1. On the other hand, an electron injection layer may be further stacked on the electron transport layer.

[0165] 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.

[0166] Except that at least one of the organic layers contains the compound represented by the chemical formula 1, the organic electroluminescent device of the present invention can be prepared by forming the organic layers and electrodes using materials and methods known in the art.

[0167] The organic layer may be formed by vacuum deposition or solution coating, examples of which include spin coating, dip coating, tape casting, inkjet printing, thermal transfer, etc., but are not limited thereto.

[0168] The substrate used in preparing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, a sheet, etc. can be used.

[0169] Furthermore, the anode material may be any anode material known in the art without limitation. For example, it may include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; 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, etc., but not limited thereto.

[0170] Furthermore, the cathode material may be any cathode material known in the art without limitation, for example, may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof, and multilayer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0171] Furthermore, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.

[0172] Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are only for illustrating the present invention, and the present invention is not limited to the following examples.

[0173] Preparation Example 1

[0174] Step 1: 3'-chloro-5'-phenyl-1,1':2',1"-terphenyl Synthesis of terphenyl

[0175]

[0176] 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 placed in 970 ml of THF and 240 ml of H2O and heated under reflux with stirring for 6 hours. After the reaction was completed, it was extracted with dichloromethane, MgSO4 was added to remove moisture and filtered. After filtration, the solvent of 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.

[0177] Mass:[(M+H) + ]:341

[0178] Step 2: Synthesis of Core1

[0179]

[0180] 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',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) 5,5,5',5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) and 5.4g (6.7mmol) of Pd(dppf)Cl2, 65.3g (665.4mmol) of KOAc and 6.3g (13.3mmol) of Xphos were placed in 750ml of 1,4-dioxane and heated under reflux for 12 hours. After the reaction was completed, it was extracted with dichloromethane, MgSO4 was added to remove moisture and filtered. After filtration, the solvent of 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 72.7g (yield 75.8%) of Core1.

[0181] Mass:[(M+H) + ]:433

[0182] Preparation Example 2

[0183] Step 1: 5'-chloro-5"-phenyl-1,1':3',1":3",1"'-quadrphenyl Synthesis of 1':3',1":3",1"'-quaterphenyl)

[0184]

[0185] 50 g (186.9 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 54.4 g (205.6 mmol) of [1,1':3',1"-terphenyl]-5'-ylboronic acid acid), 6.5 g (5.6 mmol) of Pd(PPh3)4 and 77.5 g (560.6 mmol) of K2CO3 were put into 700 ml of THF and 175 ml of H2O, and 64.1 g (yield 82.3%) of 5'-chloro-5"-phenyl-1,1':3',1":3",1"'-quaterphenyl was obtained by the same method as step 1 of preparation example 1.

[0186] Mass:[(M+H) + ]:417

[0187] Step 2: Synthesis of Core2

[0188]

[0189] 64.1 g (153.7 mmol) of 5'-chloro-5"-phenyl-1,1':3',1":3",1"'-quaterphenyl, 50.8 g (199.9 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)), 3.8 g (4.6 mmol) of Pd(dppf)Cl2, 45.3 g (461.2 mmol) of KOAc and 4.4 g (9.2 mmol) of Xphos were put into 600 ml of 1,4-dioxane, and 68.9 g (yield 88.1%) of Core2 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0190] Mass:[(M+H) + ]:508

[0191] Preparation Example 3

[0192] Step 1: 4'-chloro-6'-phenyl-1,1':2',1":3",1"'-quadrphenyl Synthesis of 1':2',1":3",1"'-quaterphenyl)

[0193]

[0194] 60 g (142.9 mmol) of 2'-bromo-5'-chloro-1,1':3',1":3",1"'-quaterphenyl, 19.2 g (157.2 mmol) of phenylboronic acid, 5.0 g (4.3 mmol) of Pd(PPh3)4 and 59.3 g (428.8 mmol) of K2CO3 was placed in 600 ml of THF and 150 ml of H2O, and 39.3 g (yield: 65.9%) of 4'-chloro-6'-phenyl-1,1':2',1":3",1"'-quaterphenyl was obtained by the same method as in Step 1 of Preparation Example 1.

[0195] Mass:[(M+H) + ]:417

[0196] Step 2: Synthesis of Core3

[0197]

[0198] 39.3 g (94.3 mmol) of 4'-chloro-6'-phenyl-1,1':2',1":3",1"'-quaterphenyl, 31.1 g (122.5 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) '-octamethyl-2,2'-bi(1,3,2-dioxaborolane)), 2.3 g (2.8 mmol) of Pd(dppf)Cl2, 27.8 g (282.8 mmol) of KOAc and 2.7 g (5.7 mmol) of Xphos were put into 400 ml of 1,4-dioxane, and 36.8 g (yield 76.7%) of Core3 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0199] Mass:[(M+H) + ]:508

[0200] Preparation Example 4

[0201] Step 1: Synthesis of Core4

[0202]

[0203] 50.0 g (146.7 mmol) of 5'-chloro-3'-phenyl-1,1':2',1"-terphenyl, 48.4 g (190.7 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) thyl-2,2'-bi(1,3,2-dioxaborolane), 3.6 g (4.4 mmol) of Pd(dppf)Cl2, 43.2 g (440.1 mmol) of KOAc and 4.2 g (8.8 mmol) of Xphos were put into 500 ml of 1,4-dioxane, and 51.12 g (yield 80.6%) of Core4 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0204] Mass:[(M+H) + ]:433

[0205] Preparation Example 5

[0206] Step 1: Synthesis of Core5

[0207]

[0208] 50.0 g (144.6 mmol) of 3'-chloro-5'-phenyl-1,1':2',1"-terphenyl-2,3,4,5,6-d5 and 47.7 g (187.9 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) were added. ',5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)), 3.5g (4.3mmol) of Pd(dppf)Cl2, 42.6g (433.7mmol) of KOAc, and 4.1g (8.7mmol) of Xphos were put into 500ml of 1,4-dioxane (1,4-dioxane), and 31.7g (yield 50.2%) of Core5 was obtained by the same method as the Core1 synthesis method in Preparation Example 1.

[0209] Mass:[(M+H) + ]:438

[0210] Preparation Example 6

[0211] Step 1: 9-(3-chloro-5-(naphthalen-2-yl)phenyl)phenanthrene Synthesis of phenyl)phenanthrene

[0212]

[0213] 55 g (149.6 mmol) of 9-(3-bromo-5-chlorophenyl)phenanthrene, 28.3 g (164.6 mmol) of naphthalen-2-ylboronic acid, 5.2 g (4.5 mmol) of Pd(PPh3)4 and 62.0 g (448.8 mmol) of K2CO3 were placed in 600 ml of THF and 150 ml of H2O, and 42.3 g (yield: 68.2%) of 9-(3-chloro-5-(naphthalen-2-yl)phenyl)phenanthrene was obtained by the same method as in Step 1 of Preparation Example 1.

[0214] Mass:[(M+H) + ]:415

[0215] Step 2: Synthesis of Core6

[0216]

[0217] 42.3 g (101.9 mmol) of 9-(3-chloro-5-(naphthalen-2-yl)phenyl)phenanthrene, 33.7 g (132.5 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) amethyl-2,2'-bi(1,3,2-dioxaborolane)), 2.5 g (4.7 mmol) of Pd(dppf)Cl2, 30.0 g (305.8 mmol) of KOAc and 2.9 g (9.5 mmol) of Xphos were put into 450 ml of 1,4-dioxane, and 31.6 g (yield 61.2%) of Core6 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0218] Mass:[(M+H) + ]:506

[0219] Preparation Example 7

[0220] Step 1: 5'-chloro-1,1':3',1":3",1"'-quadrphenyl Synthesis of quaterphenyl

[0221]

[0222] 70 g (261.6 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 54.4 g (274.7 mmol) of [1,1'-biphenyl]-3-ylboronic acid, 9.1 g (7.8 mmol) of Pd(PPh3)4 and 108.5 g (784.9 mmol) of K2CO3 were placed in 870 ml of THF and 220 ml of H2O, and 74.1 g (yield 83.1%) of 5'-chloro-1,1':3',1":3",1"'-quaterphenyl was obtained by the same method as in Step 1 of Preparation Example 1.

[0223] Mass:[(M+H) + ]:341

[0224] Step 2: Synthesis of Core7

[0225]

[0226] 74.1 g (221.7 mmol) of 5'-chloro-1,1':3',1":3",1"'-quaterphenyl, 71.8 g (282.6 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) thyl-2,2'-bi(1,3,2-dioxaborolane), 5.3 g (6.5 mmol) of Pd(dppf)Cl2, 64.0 g (652.2 mmol) of KOAc and 6.2 g (13.0 mmol) of Xphos were put into 750 ml of 1,4-dioxane, and 77.2 g (yield: 77.1%) of Core7 was obtained by the same method as the synthesis method of Core1 in Preparation Example 1.

[0227] Mass:[(M+H) + ]:433

[0228] Preparation Example 8

[0229] Step 1: 5'-chloro-1,1':3',1":4",1"'-quadrphenyl Synthesis of quaterphenyl

[0230]

[0231] 70 g (261.6 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 57.0 g (287.8 mmol) of [1,1'-biphenyl]-4-ylboronic acid, 9.1 g (7.8 mmol) of Pd(PPh3)4 and 108.5 g (784.9 mmol) of K2CO3 were placed in 700 ml of THF and 185 ml of H2O, and 82.1 g (yield 92.1%) of 5'-chloro-1,1':3',1":4",1"'-quaterphenyl was obtained by the same method as in Step 1 of Preparation Example 1.

[0232] Mass:[(M+H) +]:341

[0233] Step 2: Synthesis of Core8

[0234]

[0235] 82.1 g (220.9 mmol) of 5'-chloro-1,1':3',1":4",1"'-quaterphenyl, 79.5 g (313.1 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) thyl-2,2'-bi(1,3,2-dioxaborolane), 5.9 g (7.2 mmol) of Pd(dppf)Cl2, 70.9 g (722.6 mmol) of KOAc and 6.9 g (14.4 mmol) of Xphos were put into 750 ml of 1,4-dioxane, and 91.2 g (yield 87.6%) of Core8 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0236] Preparation Example 9

[0237] Step 1: 2-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)naphthalene Synthesis of terphenyl]-4-yl)naphthalene)

[0238]

[0239] 70 g (261.6 mmol) of 3-bromo-5-chloro-1,1'-biphenyl, 71.4 g (287.8 mmol) of (4-(naphthalen-2-yl)phenyl)boronic acid, 9.1 g (7.8 mmol) of Pd(PPh3)4 and 108.5 g (784.9 mmol) of K2CO3 were placed in 870 ml of THF and 220 ml of H2O, and 88.8 g (yield 86.8%) of 2-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)naphthalene was obtained by the same method as in Step 1 of Preparation Example 1.

[0240] Mass:[(M+H) +]:391

[0241] Step 2: Synthesis of Core9

[0242]

[0243] 88.8 g (227.2 mmol) of 2-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)naphthalene, 75.0 g (381.4 mmol) of 4,4,4',4',5,5,5',5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) 5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)), 5.6 g (6.8 mmol) of Pd(dppf)Cl2, 66.9 g (681.5 mmol) of KOAc, and 6.5 g (13.6 mmol) of Xphos were put into 800 ml of 1,4-dioxane, and 94.5 g (yield 82.1%) of Core9 was obtained by the same method as the Core1 synthesis method of Preparation Example 1.

[0244] Mass:[(M+H) + ]:433

[0245] Synthesis Example 1: Synthesis of Compound 1

[0246]

[0247] 15.0 g (1 eq, 31.0 mmol) of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine, 14.1 g (1.05 eq, 32.5 mmol) of Core 1 of Preparation Example 1, 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 30.3 g (3.0 eq, 93.0 mmol) of Cs2CO3 and 0.9 g (0.06 eq, 1.9 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 18.6 g (yield 78.2%) of compound 1.

[0248] Mass:[(M+H) + ]:753

[0249] Synthesis Example 2: Synthesis of Compound 3

[0250]

[0251] 17.0 g (1 eq, 41.8 mmol) of 4-chloro-6-(naphtho[2,1-b]benzofuran-8-yl)-2-phenylpyrimidine, 22.3 g (1.05 eq, 43.9 mmol) of Core 2 of Preparation Example 2, 2.1 g (0.05 eq, 1.3 mmol) of Pd(PPh3)4 and 17.3 g (3.0 eq, 125.4 mmol) of K2CO3 were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added for filtration. The solvent of the filtered organic layer was removed, and then the organic layer was purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 22.4 g (yield: 71.1%) of Compound 3.

[0252] Mass:[(M+H) + ]:753

[0253] Synthesis Example 3: Synthesis of Compound 6

[0254]

[0255] 10.0 g (1 eq, 18.7 mmol) of 2-(4-chlorophenyl)-4-(phenanthro[3,2-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine, 10.0 g (1.05 eq, 19.7 mmol) of Core 2 of Preparation Example 2, 0.1 g (0.03 eq, 0.56 mmol) of Pd(OAc)2, 18.3 g (3.0 eq, 56.2 mmol) of Cs2CO3 and 0.5 g (0.06 eq, 1.1 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 13.5 g (yield 81.9%) of compound 6.

[0256] Mass:[(M+H) + ]:881

[0257] Synthesis Example 4: Synthesis of Compound 10

[0258]

[0259] 10.0 g (1 eq, 14.0 mmol) of 2-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)-4-phenyl-6-(4-phenylnaphtho[2,3-b]benzofuran-1-yl)-1,3,5-triazine, 2.9 g (1.05 eq, 14.74 mmol) of [1,1'-biphenyl]-2-ylboronic acid acid), 0.1g (0.03eq, 0.42mmol) of Pd (OAc) 2, 13.7g (3.0eq, 42.1mmol) of Cs 2 CO 3 and 0.4g (0.06eq, 0.8mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH, and 50ml of H 2 O and heated under reflux for 4 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO 4. The solvent of the organic layer after filtration was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 4.4g (yield of 38.2%) of compound 10.

[0260] Mass:[(M+H) + ]:831

[0261] Synthesis Example 5: Synthesis of Compound 11

[0262]

[0263] The same process was carried out with the remaining reagents in the same equivalent ratio as in the above Synthesis Example 1, except that 15.0 g (35.1 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-triazine. The same process was carried out with the remaining reagents in the same equivalent ratio as in the above Synthesis Example 1, to obtain 22.9 g (yield 86.3%) of Compound 11.

[0264] Mass:[(M+H) + ]:754

[0265] Synthesis Example 6: Synthesis of Compound 23

[0266]

[0267] 12.0 g (1 eq, 21.4 mmol) of 2-(4-chlorophenyl)-4-phenyl-6-(8-phenylnaphtho[2,1-b]benzofuran-10-yl)-1,3,5-triazine, 6.2 g (1.05 eq, 22.5 mmol) of [1,1':3',1"-terphenyl]-5'-ylboronic acid acid), 0.1g (0.03eq, 0.64mmol) of Pd(OAc)2, 20.9g (3.0eq, 64.3mmol) of Cs2CO3 and 0.6g (0.06eq, 1.3mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH, and 50ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from monochlorobenzene to obtain 13.9g (yield of 85.8%) of compound 23.

[0268] Mass:[(M+H) + ]:755

[0269] Synthesis Example 7: Synthesis of Compound 27

[0270]

[0271] 13.0 g (1 eq, 26.9 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenylpyrimidine, 14.4 g (1.05 eq, 28.3 mmol) of Core 3 of Preparation Example 3, 0.2 g (0.03 eq, 0.81 mmol) of Pd(OAc)2, 26.3 g (3.0 eq, 80.8 mmol) of Cs2CO3 and 0.8 g (0.06 eq, 1.6 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H2O and heated under reflux for 6 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered after adding MgSO4. The solvent of the filtered organic layer was removed, and then the organic layer was purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 16.8 g (yield 75.2%) of Compound 16.

[0272] Mass:[(M+H) + ]:829

[0273] Synthesis Example 8: Synthesis of Compound 28

[0274]

[0275] 20.0 g (1 eq, 34.8 mmol) of 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine 15.8g (1.05eq, 36.5mmol) of Core 4 of Preparation Example 4, 0.2g (0.03eq, 1.0mmol) of Pd (OAc) 2, 34.0g (3.0eq, 104.3mmol) of Cs 2 CO 3 and 1.0g (0.06eq, 2.1mmol) of Xphos were placed in 300ml of toluene, 75ml of EtOH and 75ml of H 2 O and heated under reflux for 6 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO 4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 17.9g (yield 61.1%) of compound 28.

[0276] Mass:[(M+H) + ]:845

[0277] Synthesis Example 9: Synthesis of Compound 37

[0278]

[0279] 10.0 g (1 eq, 20.7 mmol) of 2-(3-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1,3,5-triazine, 9.2 g (1.05 eq, 21.7 mmol) of (4',5'-diphenyl-[1,1':2',1"-terphenyl]-3'-yl)boronic acid acid), 0.1g (0.03eq, 0.62mmol) of Pd(OAc)2, 20.2g (3.0eq, 61.9mmol) of Cs2CO3 and 0.6g (0.06eq, 1.2mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH, and 50ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene to obtain 6.7g (yield 38.9%) of compound 37.

[0280] Mass:[(M+H) + ]:831

[0281] Synthesis Example 10: Synthesis of Compound 38

[0282]

[0283] 25.0 g (1 eq, 51.7 mmol) of 2-(3-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1,3,5-triazine, 23.7 g (1.05 eq, 54.7 mmol) of Core 5 of Preparation Example 5, 0.4 g (0.03 eq, 1.6 mmol) of Pd(OAc)2, 50.5 g (3.0 eq, 155.0 mmol) of Cs2CO3 and 1.5 g (0.06 eq, 3.1 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH and 75 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 31.3 g (yield 79.9%) of compound 38.

[0284] Mass:[(M+H) + ]:759

[0285] Synthesis Example 11: Synthesis of Compound 39

[0286]

[0287] The reaction mixture was prepared by mixing 10.0 g (17.8 mmol) of 2-(4-chlorophenyl)-4-(4-phenylnaphtho[2,3-b]benzofuran-1-yl)-6-(pyridin-2-yl)-1,3,5-triazine instead of 2-(4-chlorophenyl)-4-(4-phenylnaphtho[2,3-b]benzofuran-1-yl)-6-(pyridin-2-yl)-1,3,5-triazine. Except for (4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine, the remaining reagents were subjected to the same process in the same equivalent ratio as in Synthesis Example 1 to obtain 13.1 g (yield 88.3%) of compound 39.

[0288] Mass:[(M+H) + ]:832

[0289] Synthesis Example 12: Synthesis of Compound 41

[0290]

[0291] 15.0 g (1 eq, 31.1 mmol) of 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-9-yl)-2-phenylpyrimidine, 14.1 g (1.05 eq, 32.6 mmol) of Core 8 of Preparation Example 8, 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 30.4 g (3.0 eq, 93.2 mmol) of Cs2CO3 and 0.9 g (0.06 eq, 1.9 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH and 75 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added for filtration. The solvent of the filtered organic layer was removed, and then the organic layer was purified by column chromatography using dichloromethane and hexane, and then recrystallized from dichlorobenzene to obtain 19.7 g (yield: 84.2%) of Compound 41.

[0292] Mass:[(M+H) + ]:754

[0293] Synthesis Example 13: Synthesis of Compound 45

[0294]

[0295] 20.0 g (1 eq, 36.4 mmol) of 4-(3-chlorophenyl)-6-(dinaphtho[2,1-b:1',2'-d]thiophen-6-yl)-2-phenylpyrimidin e, 19.4 g (1.05 eq, 38.3 mmol) of Core 6 of Preparation Example 6, 0.3 g (0.03 eq, 1.1 mmol) of Pd(OAc) 2, 35.6 g (3.0 eq, 109.3 mmol) of Cs 2 CO 3 and 1.0 g (0.06 eq, 2.2 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH and 75 ml of H 2 O and heated under reflux for 6 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 19.4 g (yield 59.7%) of compound 45.

[0296] Mass:[(M+H) + ]:893

[0297] Synthesis Example 14: Synthesis of Compound 48

[0298]

[0299] 15.0 g (1 eq, 31.1 mmol) of 4-(3-chlorophenyl)-6-(naphtho[1,2-b]benzofuran-10-yl)-2-phenylpyrimidine, 14.1 g (1.05 eq, 32.6 mmol) of Core 1 of Preparation Example 1, 0.2 g (0.03 eq, 0.9 mmol) of Pd(OAc)2, 30.4 g (3.0 eq, 93.2 mmol) of Cs2CO3 and 0.9 g (0.06 eq, 1.9 mmol) of Xphos were placed in 300 ml of toluene, 75 ml of EtOH and 75 ml of H2O and heated under reflux for 6 hours to react. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added for filtration. The solvent of the filtered organic layer was removed, and then the organic layer was purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene to obtain 19.2 g (yield: 82.1%) of Compound 48.

[0300] Mass:[(M+H) + ]:754

[0301] Synthesis Example 15: Synthesis of Compound 50

[0302]

[0303] The same process was carried out with the remaining reagents in the same equivalent ratio as in Synthesis Example 1, except that 15.0 g (26.9 mmol) of 3-(4-(3-chlorophenyl)-6-phenylpyrimidin-2-yl)-5-phenyl-5H-benzo[b]carbazole was used instead of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine. The same process was carried out with the same equivalent ratio as in Synthesis Example 1 to obtain 17.1 g (yield 76.7%) of Compound 50.

[0304] Mass:[(M+H) + ]:829

[0305] Synthesis Example 16: Synthesis of Compound 51

[0306]

[0307] The same process was carried out with the remaining reagents in the same equivalent ratio as in Synthesis Example 1, except that 15.0 g (28.1 mmol) of 2-(4-chlorophenyl)-4-(phenanthro[9,10-b]benzofuran-12-yl)-6-phenylpyrimidine was used instead of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine. The same process was carried out with the remaining reagents in the same equivalent ratio as in Synthesis Example 1 to obtain 20.9 g (yield: 92.3%) of Compound 51.

[0308] Mass:[(M+H) + ]:804

[0309] Synthesis Example 17: Synthesis of Compound 54

[0310]

[0311] 16.0 g (1 eq, 26.3 mmol) of 5-(4-(4-chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-7-phenyl-7H-dibenzo[c,g]carbazole, 11.9 g (1.05 eq, 27.6 mmol) of Core 7 of Preparation Example 7, 0.2 g (0.03 eq, 0.8 mmol) of Pd(OAc)2, 25.7 g (3.0 eq, 78.8 mmol) of Cs2CO3 and 0.7 g (0.06 eq, 1.6 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H2O and heated under reflux for 8 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then the mixture was purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 15.3 g (yield 66.3%) of compound 50.

[0312] Mass:[(M+H) + ]:879

[0313] Synthesis Example 18: Synthesis of Compound 57

[0314]

[0315] 13.0 g (1 eq, 24.3 mmol) of 2-(4-chlorophenyl)-4-(dinaphtho[1,2-b:1',2'-d]furan-12-yl)-6-phenyl-1,3,5-triazine, 7.0 g (1.05 eq, 25.6 mmol) of [1,1':3',1"-terphenyl]-5'-ylboronic acid Acid), 0.2g (0.03eq, 0.7mmol) of Pd (OAc) 2, 23.8g (3.0eq, 73.0mmol) of Cs 2CO 3 and 0.7g (0.06eq, 1.5mmol) of Xphos were placed in 400ml of toluene (Toluene), 100ml of EtOH, and 100ml of H 2 O and heated under reflux for 8 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO 4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 15.7g (yield of 88.8%) of compound 57.

[0316] Mass:[(M+H) + ]:729

[0317] Synthesis Example 19: Synthesis of Compound 59

[0318]

[0319] 10.0 g (1 eq, 17.9 mmol) of 2-([1,1'-biphenyl]-3-yl)-4-(4-chlorophenyl)-6-(naphtho[2,3-b]benzofuran-1-yl)-1,3,5-triazine, 5.1 g (1.05 eq, 18.7 mmol) of [1,1':3',1"-terphenyl]-5'-ylboronic acid Acid), 0.1g (0.03eq, 0.5mmol) of Pd(OAc)2, 17.5g (3.0eq, 53.6mmol) of Cs2CO3 and 0.5g (0.06eq, 1.1mmol) of Xphos were placed in 300ml of toluene (Toluene), 75ml of EtOH, and 75ml of H2O and heated under reflux for 8 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 8.8g (yield of 65.7%) of compound 59.

[0320] Mass:[(M+H) + ]:755

[0321] Synthesis Example 20: Synthesis of Compound 67

[0322]

[0323] 20.0 g (1 eq, 49.2 mmol) of 4-chloro-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine, 22.3 g (1.05 eq, 51.6 mmol) of Core 8 of Preparation Example 8, 2.1 g (0.05 eq, 2.5 mmol) of Pd(PPh3)4 and 20.4 g (3.0 eq, 147.5 mmol) of K2CO3 were placed in 300 ml of toluene, 75 ml of EtOH and 75 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, extraction was performed with dichloromethane, and MgSO4 was added for filtration. The solvent of the filtered organic layer was removed, and then the organic layer was purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 28.2 g (yield 84.8%) of Compound 67.

[0324] Mass:[(M+H) + ]:677

[0325] Synthesis Example 21: Synthesis of Compound 72

[0326]

[0327] 20.0 g (1 eq, 41.4 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenylpyrimidine, 11.9 g (1.05 eq, 43.5 mmol) of [1,1':3',1"-terphenyl]-5'-ylboronic acid Acid), 0.3g (0.03eq, 1.2mmol) of Pd (OAc) 2, 40.5g (3.0eq, 124.2mmol) of Cs 2 CO 3 and 1.2g (0.06eq, 2.5mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH, and 50ml of H 2 O and heated under reflux for 8 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO 4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 22.9g (yield of 81.9%) of compound 72.

[0328] Mass:[(M+H) + ]:677

[0329] Synthesis Example 22: Synthesis of Compound 76

[0330]

[0331] Except that 15.0 g (35.1 mmol) of 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine was used instead of 5-(4-(4-chlorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-7-phenyl-7H-dibenzo[c,g]carbazole, the remaining reagents were subjected to the same process in the same equivalent ratio as in Synthesis Example 9 to obtain 23.6 g (yield 75.8%) of Compound 76.

[0332] Mass:[(M+H) + ]:753

[0333] Synthesis Example 23: Synthesis of Compound 80

[0334]

[0335] 10.0 g (1 eq, 20.7 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenylpyrimidine, 11.1 g (1.05 eq, 21.7 mmol) of 2-([1,1':3',1":3",1"':4"',1""-pentaphenyl]-5"-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1,1':3',1":3",1"':4"',1""-quinquephenyl]-5"-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane), 0.1g (0.03eq, 0.62mmol) of Pd(OAc)2, 20.2g (3.0eq, 62.1mmol) of Cs2CO3 and 0.6g (0.06eq, 1.2mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH and 50ml of H2O and heated under reflux for 7 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from monochlorobenzene to obtain 12.7g (yield 74.4%) of compound 80.

[0336] Mass:[(M+H) + ]:830

[0337] Synthesis Example 24: Synthesis of Compound 81

[0338]

[0339] The same process was carried out with the remaining reagents in the same equivalent ratio as in Synthesis Example 6 except that 15.0 g (31.0 mmol) of 2-(4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenyl-1,3,5-triazine was used instead of 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine. 19.2 g (yield 82.2%).

[0340] Mass:[(M+H) + ]:755

[0341] Synthesis Example 25: Synthesis of Compound 82

[0342]

[0343] 17.0 g (1 eq, 29.5 mmol) of 2-(3-chlorophenyl)-4-phenyl-6-(11-phenylbenzo[b]naphtho[1,2-d]thiophen-8-yl)-1,3,5-triazine, 14 0.9 g (1.05 eq, 31.0 mmol) of Core 9 of Preparation Example 9, 0.9 g (0.03 eq, 0.89 mmol) of Pd (OAc) 2, 28.8 g (3.0 eq, 74.1 mmol) of Cs 2 CO 3 and 0.8 g (0.06 eq, 1.8 mmol) of Xphos were placed in 200 ml of toluene, 50 ml of EtOH and 50 ml of H 2 O and heated under reflux for 7 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO 4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from toluene acetone to obtain 16.3 g (yield of 61.8%) of compound 82.

[0344] Mass:[(M+H) + ]:896

[0345] Synthesis Example 26: Synthesis of Compound 83

[0346]

[0347] 10.0 g (1 eq, 20.7 mmol) of 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-9-yl)-2-phenylpyrimidine, 9.9 g (1.05 eq, 21.7 mmol) of (5-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)boronic acid Acid), 0.1g (0.03eq, 0.62mmol) of Pd(OAc)2, 20.2g (3.0eq, 62.1mmol) of Cs2CO3 and 0.6g (0.06eq, 1.2mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH, and 50ml of H2O and heated under reflux for 7 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from dichlorobenzene to obtain 9.9g (yield of 62.1%) of compound 83.

[0348] Mass:[(M+H) + ]:768

[0349] Synthesis Example 27: Synthesis of Compound 84

[0350]

[0351] 12.0 g (1 eq, 24.8 mmol) of 2-(4-chlorophenyl)-4-(naphtho[2,3-b]benzofuran-3-yl)-6-phenyl-1,3,5-triazine, 11.3 g (1.05 eq, 26.0 mmol) of Core 8 of Preparation Example 8, 0.2 g (0.03 eq, 0.74 mmol) of Pd(OAc)2, 24.2 g (3.0 eq, 74.4 mmol) of Cs2CO3 and 0.7 g (0.06 eq, 1.5 mmol) of Xphos were placed in 400 ml of toluene, 100 ml of EtOH and 100 ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added and filtered, the solvent of the filtered organic layer was removed, and then the mixture was purified by column chromatography using dichloromethane and hexane, and then recrystallized from dichlorobenzene to obtain 17.1 g (yield 91.2%) of Compound 84.

[0352] Mass:[(M+H) + ]:755

[0353] Synthesis Example 28: Synthesis of Compound 89

[0354]

[0355] 10.0 g (1 eq, 15.7 mmol) of 2-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6-phenylpyrimidine, 4.5 g (1.05 eq, 16.5 mmol) of [1,1':3',1"-terphenyl]-4'-ylboronic acid acid), 0.1g (0.03eq, 0.47mmol) of Pd(OAc)2, 15.4g (3.0eq, 47.2mmol) of Cs2CO3 and 0.4g (0.06eq, 0.9mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH and 50ml of H2O and heated under reflux for 6 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from dichlorobenzene to obtain 5.9g (yield 44.9%) of compound 89.

[0356] Mass:[(M+H) + ]:830

[0357] Synthesis Example 29: Synthesis of Compound 94

[0358]

[0359] 10.0 g (1 eq, 20.7 mmol) of 4-(3-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine, 9.5 g (1.05 eq, 21.7 mmol) of 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1"-terphenyl]-4'-yl-2,3,4,5,6-d5)-1,3,2-dioxaborolane ,5-tetramethyl-2-(5'-phenyl-[1,1':2',1"-terphenyl]-4'-yl-2,3,4,5,6-d5)-1,3,2-dioxaborolane), 0.1g (0.03eq, 0.62mmol) of Pd(OAc)2, 20.2g (3.0eq, 62.1mmol) of Cs2CO3 and 0.6g (0.06eq, 1.2mmol) of Xphos were placed in 200ml of toluene (Toluene), 50ml of EtOH and 50ml of H2O and heated under reflux for 6 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then purified by column chromatography using dichloromethane and hexane, and then recrystallized from monochlorobenzene to obtain 14.0g (yield 89.3%) of compound 94.

[0360] Mass:[(M+H) + ]:759

[0361] Synthesis Example 30: Synthesis of Compound 95

[0362]

[0363] 13.0 g (1 eq, 31.9 mmol) of 4-chloro-6-(naphtho[2,1-b]benzofuran-10-yl)-2-phenylpyrimidine, 14.7 g (1.05 eq, 33.6 mmol) of 2-([1,1':3',1":4",1"'-quadrphenyl]-5'-yl-2,3,4,5,6-d5)-4,4,5,5-tetramethyl-1,3,2-dioxopyran Borane (2-([1,1':3',1":4",1"'-quaterphenyl]-5'-yl-2,3,4,5,6-d5)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane), 1.8g (0.05eq, 1.6mmol) of Pd(PPh3)4 and 13.2g (3.0eq, 95.8mmol) of K2CO3 were placed in 200ml of toluene, 50ml of EtOH and 50ml of H2O and heated under reflux for 4 hours to react. After the reaction was completed, it was extracted with dichloromethane and filtered by adding MgSO4. The solvent of the filtered organic layer was removed, and then it was purified by column chromatography using dichloromethane and hexane, and then recrystallized from monochlorobenzene to obtain 18.8g (yield 86.4%) of compound 95.

[0364] Mass:[(M+H) + ]:683

[0365] Example 1 to Example 10: Preparation of blue organic electroluminescent device

[0366] The compound synthesized in the above synthesis example was purified to high purity by sublimation by a generally known method, and then a blue organic electroluminescent device was prepared as follows.

[0367] First, use distilled water to ultrasonically clean the After washing with distilled water, ultrasonic cleaning with isopropyl alcohol, acetone, methanol and other solvents and drying, the substrate was transferred to a UV-ozone (OZONE) cleaning machine (Power sonic405, HWASHIN TECH), and then the substrate was cleaned with UV for 5 minutes and transferred to a vacuum evaporation machine.

[0368] On the ITO transparent electrode prepared as above, HT-1+2% HAT-CN BD / Compounds 1, 3, 11, 27, 41, 57, 59, 81, 83, 84: LiQ = 1:1 The layers are stacked sequentially to prepare an organic electroluminescent device.

[0369] In this case, the structures of the compounds HT-1, HAT-CN, HT-2, BH, BD, ET-1, ET-2 and LiQ used are as follows.

[0370]

[0371]

[0372] Comparative Example 1: Preparation of a blue organic electroluminescent device

[0373] A blue organic electroluminescent device was prepared in the same manner as in Example 1, except that Alq3 was evaporated to a thickness of 30 nm instead of Compound 1 as the electron transport layer material.

[0374] Evaluation Example 1

[0375] The blue organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Example 1 were measured at 10 mA / cm 2 The driving voltage, current efficiency and luminescence peak at a current density of , are shown in the following Table 1.

[0376] Table 1

[0377]

[0378]

[0379] As shown in Table 1 above, it can be seen that compared with the blue organic electroluminescent device of Comparative Example 1 in which the existing ET-1 is used for the electron transport layer, the blue organic electroluminescent devices of Examples 1 to 10 using the compounds of the present invention as electron transport layer materials show excellent performance in terms of driving voltage, luminescence peak and current efficiency.

[0380] Example 11 to Example 28: Preparation of blue organic electroluminescent device

[0381] The compound synthesized in the above synthesis example was purified to high purity by sublimation by a generally known method, and then a blue organic electroluminescent device was prepared as follows.

[0382] Ultrasonic cleaning of the coating with a thickness of After washing with distilled water, ultrasonic cleaning with isopropyl alcohol, acetone, methanol and other solvents and drying, the substrate was transferred to a UV-ozone (OZONE) cleaning machine (Power sonic 405, HWASHIN TECH), and then the substrate was cleaned with UV for 5 minutes and transferred to a vacuum evaporation machine.

[0383] On the ITO transparent electrode prepared as above, HT-1+2% HAT-CN BD / Compounds 6, 10, 23, 27, 37-39, 48, 51, 54, 57, 67, 72, 80-81, 89, 94-95 The organic electroluminescent devices of Examples 11 to 28 were prepared by sequential stacking.

[0384] Comparative Examples 2 to 4: Preparation of Blue Organic Electroluminescent Devices

[0385] The blue organic electroluminescent devices of Comparative Examples 2 to 4 were prepared in the same manner as in Example 11, except that Compounds ET-2 to ET-4 were used instead of Compound 6 as the electron transport auxiliary layer material.

[0386] In this case, the structures of ET-2, ET-3, and ET-4 used are as follows.

[0387]

[0388] Evaluation Example 2

[0389] The organic electroluminescent devices prepared in Examples 11 to 28 and Comparative Examples 2 to 5 were measured at 10 mA / cm 2 The driving voltage, emission wavelength, current efficiency, and emission wavelength at a current density of are shown in the following Table 2.

[0390] Table 2

[0391]

[0392]

[0393] As shown in Table 2 above, it can be seen that compared with the organic electroluminescent devices of Comparative Examples 2 to 4, the blue organic electroluminescent devices of Examples 11 to 28 containing the compounds of the present invention as electron transport auxiliary layer materials show excellent performance in current efficiency and driving voltage.

Claims

1. A compound as shown in the following chemical formula 1, characterized in that: Chemical formula 1: In the above chemical formula 1, Multiple Xs are the same as or different from each other and are each independently CR5 or N, but at least 2 of the multiple Xs are N, Ar1 is selected from C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 and heteroarylamine groups having 5 to 60 nuclear atoms, Y is O, S or NR4, Ring A and Ring B are the same or different from each other, and are each independently C5 to C5 containing or not containing heteroatoms. 18 A monocyclic or polycyclic hydrocarbon ring group, but at least one of the rings A and B is C 10 ~C 18 A polycyclic hydrocarbon ring group, R2 to R3 are the same or different from each other and are independently selected from deuterium, C1 to C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The group consisting of aryl heteroaryl amine groups and heteroaryl amine groups having 5 to 60 nuclear atoms, or they can combine with adjacent groups to form a condensed ring; R4 to R5 are the same or different from each other and are independently selected from hydrogen, deuterium, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C3~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Monoaryl phosphinyl, C6~C 60 Diarylphosphinyl, C6~C 60 Aromatic amine group, C5~C 60 The group consisting of aryl heteroaryl amine groups and heteroaryl amine groups having 5 to 60 nuclear atoms; L can be selected from C6~C 18 The group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, R1 is selected from C6~C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, and C6 to C 60 In the group consisting of arylsilyl groups, m is an integer greater than or equal to 1, n is an integer from 0 to 3, a is an integer from 0 to 2, b is an integer from 0 to 4, The arylene group and heteroarylene group of L; the aryl group, heteroaryl group and arylsilyl group of R1; and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboryl group, arylboryl group, arylphosphino group, arylphosphine oxide group and arylamine group of R2 to R5 and Ar1 can be independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclear atoms, C6 to C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1 to C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 Aryl phosphine oxide group, C6~C 60 Aromatic amine group, C5~C 60 and heteroarylamine groups having 5 to 60 nuclear atoms, in which case, when there are a plurality of such substituents, they may be the same as or different from each other, However, the total number of carbon atoms contained in the ring containing Y, which may be substituted or unsubstituted, is at least 16.

2. The compound according to claim 1, characterized in that R1 is selected from C6~C 30 aryl, heteroaryl having 5 to 30 nuclear atoms, and C6 to C 30 In the group consisting of arylsilyl groups, m is an integer from 1 to 5, (R1) substituted or unsubstituted m The total number of carbon atoms contained in is at least 18.

3. The compound according to claim 1, characterized in that The ring containing Y is selected from the group of substituents shown in the following chemical formula: In the above formula, * indicates the site of connection with the above chemical formula 1, Rings D are the same as or different from each other and are each independently a monocyclic or polycyclic hydrocarbon ring group containing or not containing a heteroatom, Y, R2, R3, a and b are as defined in claim 1.

4. The compound according to claim 1, characterized in that The ring containing Y is selected from the group of substituents shown in the following chemical formula: In the above formula, * indicates the site of connection with the above chemical formula 1, R4 is as defined in claim 1.

5. The compound according to claim 1, characterized in that The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 2 to 5: Chemical formula 2: Chemical formula 3: Chemical formula 4: Chemical formula 5: In the above formula, * indicates the site of connection with the above chemical formula 1, A, B, Y, L, R1-R3, Ar1, a, b, m and n are respectively defined as in claim 1.

6. The compound according to claim 1, characterized in that Ar1 and R2 to R3 are the same or different from each other and are independently selected from C6 to C 60 The group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms, R4 is selected from C6~C 30 The present invention is a group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.

7. The compound according to claim 1, characterized in that Ar1 is selected from the group consisting of substituents shown in the following chemical formula:

8. The compound according to claim 1, characterized in that The compound represented by the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 6 to 13: Chemical formula 6: Chemical formula 7: Chemical formula 8: Chemical formula 9: Chemical formula 10: Chemical formula 11: Chemical formula 12: Chemical formula 13: In the above formula, Ring D is a monocyclic or polycyclic hydrocarbon ring group which may contain heteroatoms, X, Y, R1-R3, Ar1, a, b, m and n are respectively as defined in claim 1.

9. The compound according to claim 1, characterized in that The compound represented by the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 14 to 25: 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, X, Y, A, B, Ar1, L, R1-R3, a, b and n are respectively defined as in claim 1.

10. The compound according to claim 1, characterized in that The compound represented by the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1 to 108:

11. The compound according to claim 1, characterized in that The compound shown in the above chemical formula 1 is a material for a light-emitting layer, an electron transport layer or an electron transport auxiliary layer.

12. An organic electroluminescent device, characterized in that: The invention comprises an anode, a cathode and one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound according to any one of claims 1 to 11.

13. The organic electroluminescent device according to claim 12, characterized in that: The organic layer containing the above 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-improving layer, an electron transport layer and an electron transport auxiliary layer.

14. The organic electroluminescent device according to claim 13, characterized in that: The above compound is contained as a material of at least one of a phosphorescent host material of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

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