Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using same, and, more specifically, to an organic compound exhibiting excellent electron injection and transport ability and thermal stability, and an organic electroluminescent device comprising same in one or more organic layers, thereby having improved properties such as luminous efficiency, driving voltage and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

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

[0002] In an organic electroluminescent device (hereinafter referred to as an "organic EL device"), when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the materials used in the organic layer can be classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials depending on their function.

[0003] The materials forming the light-emitting layer of an organic EL device can be classified into blue, green, and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. Furthermore, a host / dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. Dopant materials can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescent materials, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

[0004] To date, NPB, BCP, Alq3, etc., which are expressed by the following chemical formulas, are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant / host materials for luminescent materials. In particular, among luminescent materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are used as blue, green, and red dopant materials as phosphorescent materials that have great advantages in terms of improving efficiency. Currently, CBP has shown excellent properties as a phosphorescent host material.

[0005] However, while conventional organic layer materials offer advantages in terms of luminescence characteristics, their low glass transition temperatures and poor thermal stability make them unsatisfactory in terms of lifespan in organic EL devices. Therefore, the development of high-performance organic layer materials is urgently needed.

[0006] The present invention is applicable to organic electroluminescent devices, and aims to provide a novel organic compound having excellent hole and electron injection and transport capabilities, luminescence capabilities, etc.

[0007] 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.

[0008] To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1:

[0009]

[0010] (In the above chemical formula 1,

[0011] X1 to X3 are the same or different, and are each independently N or C(Ar2), provided that two of X1 to X3 are N,

[0012] Ar1 and Ar2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0013] Y1 is O or S,

[0014] n is an integer from 0 to 3,

[0015] Multiple L1s are identical or different from each other,

[0016] L1 is a single bond, or C1~C 60 alkylene group, C6~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms,

[0017] o is an integer from 0 to 5,

[0018] p is 0 or 1,

[0019] q is 0 or 1,

[0020] However, o+p+q≥2,

[0021] a is an integer from 0 to 7,

[0022] b is an integer from 0 to 4,

[0023] c is an integer from 0 to 4,

[0024] d and e are integers from 0 to 5, respectively.

[0025] R1 to R5 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano, nitro, amino, hydroxy, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, or condensed with adjacent groups to form a condensed ring,

[0026] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2, the alkylene group, arylene group and heteroarylene group of the above L1, 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, arylamine group and condensed ring of the above R1 to R5 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, Nitro group, amino group, hydroxy group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

[0027] In addition, the present invention provides an organic electroluminescent device comprising an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the aforementioned organic compound.

[0028] For example, the organic layer including the organic compound may be an electron transport layer and / or an electron transport auxiliary layer.

[0029] 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 and injection ability, luminescence ability, heat resistance, electrochemical stability, etc.

[0030] 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.

[0031] 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.

[0032] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0033] FIG. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to a first embodiment of the present invention.

[0034] FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to a second embodiment of the present invention.

[0035] FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to a third embodiment of the present invention.

[0036] <Explanation of symbols>

[0037] 100: positive, 200: negative,

[0038] 300: Organic layer, 310: Hole injection layer,

[0039] 320: hole transport layer, 330: light emitting layer,

[0040] 340: electron transport layer, 350: electron injection layer,

[0041] 360: Electron transport auxiliary layer

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

[0043] <New organic compounds>

[0044] The compound according to the present invention has a basic skeleton in which a dibenzo moiety and a plurality of aryl moieties are each directly or through a linker group, centered on a pyrimidine moiety, which is an electron withdrawing group (EWG) with excellent electron transport ability, and is represented by the above chemical formula 1. The compound of the present invention represented by the chemical formula 1 has excellent electron injection and transport ability, electrochemical stability, heat resistance, etc., and can be used as an electron transport layer material or an electron transport auxiliary layer material that can improve the high efficiency, long life, and driving voltage characteristics of an organic electroluminescent device.

[0045] Typically, in organic electroluminescent devices, when the injection of electrons from the electron transport layer to the emitting layer becomes faster, the device's lifespan tends to decrease. This phenomenon occurs because the region where excitons are formed in the emitting layer is concentrated on one side. To solve this problem, the electron injection rate is generally adjusted to be slow. However, simply adjusting the electron injection rate to be slow results in a decrease in efficiency in blue devices. To solve this problem, the electron transport capacity must be adjusted so that excitons are formed evenly throughout the emitting layer while maintaining a fast electron injection rate.

[0046] Accordingly, in the present invention, a molecular structure was designed such that a dibenzo moiety and a plurality of aryl moieties are each directly or through a linker group, centered on a pyrimidine moiety, which is an electron withdrawing group (EWG) with excellent electron transport ability.

[0047] Here, the dibenzo moiety (e.g., dibenzofuran, dibenzothiophene) has amphoteric physicochemical properties for both holes and electrons, and has an unshared electron pair with excellent conductivity. In addition, the plurality of aryl moieties contain a terphenyl group, which can control the stability of the molecule and the electron transport rate of the material. By bonding the dibenzo moiety and the plurality of aryl groups to each side of the pyrimidine moiety, the compound of the present invention can structurally increase the electron density of the pyrimidine moiety having electron transport ability, thereby controlling the electron transport ability, and accordingly, the electron transport ability is further improved compared to the structure of existing known materials, and high efficiency and long life of the device can be realized. In addition, the present invention can have physicochemical properties more suitable for electron transport by including a pyrimidine group having a shallower LUMO in order to improve the electron transfer rate and electron injection rate. In addition, by introducing a plurality of aryl moieties on one side of the pyrimidine group, which is an EWG, the compound of the present invention has an electron injection rate controllable, high electrochemical stability, and excellent thermal stability due to a high glass transition temperature (Tg).

[0048] In addition, since the compound represented by Chemical Formula 1 of the present invention has a higher triplet energy than the light-emitting layer, 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]

[0051] The compound represented by chemical formula 1 according to the present invention has a structure including a pyrimidine moiety ('X1 to X3-containing heteroaromatic ring moiety'); a dibenzo group moiety ('Y1-containing ring') directly bonded to one side of the pyrimidine moiety or bonded via a separate linker group; and a plurality of aryl group moieties (a plurality of aryl groups substituted or unsubstituted with R2 to R5) bonded to the other side of the pyrimidine moiety.

[0052] The above pyrimidine moiety is a monocyclic nitrogen-containing heteroaromatic ring containing two nitrogen atoms, wherein X1 to X3 are the same or different and are each independently N or C(Ar2), provided that two of X1 to X3 are N. For example, the above pyrimidine moiety ( The moiety) may be selected from the group consisting of the following moieties Az1-1 to Az1-3. These pyrimidine moieties contain two nitrogens and are electron withdrawing groups (EWGs) with high electron absorption properties, and therefore, the compounds of the present invention exhibit excellent electron absorption properties, which are advantageous for electron injection and transport.

[0053]

[0054] In the above moieties Az1-1 to Az1-3,

[0055] * indicates a part connected to the above chemical formula 1,

[0056] Ar1 and Ar2 are each as defined in the above chemical formula 1.

[0057] In the chemical formula 1 according to the present invention, Ar1 and Ar2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), C1~C 20Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups, and more specifically, it can be selected from the group consisting of hydrogen, deuterium (D), phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, dibenzofuran group, dibenzothiophene group, phenanthrolinyl group, and carbazolyl group.

[0058] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0059] For example, Ar1 may be selected from the group consisting of the following substituents S1-1 to S1-16, but is not limited thereto.

[0060]

[0061] In the above substituents S1-1 to S1-16,

[0062] f is an integer from 0 to 5, specifically an integer from 0 to 2,

[0063] g is an integer from 0 to 4, specifically an integer from 0 to 2,

[0064] h is an integer from 0 to 7, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0065] i is an integer from 0 to 6, specifically an integer from 0 to 3,

[0066] j is an integer from 0 to 9, specifically an integer from 0 to 4, and more specifically an integer from 0 to 2,

[0067] k is an integer from 0 to 11, specifically an integer from 0 to 6, and more specifically an integer from 0 to 3,

[0068] Multiple R's are the same or different from each other,

[0069] R is deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30can be selected from the group consisting of arylamine groups, and more specifically, each independently selected from the group consisting of deuterium (D), cyano group (-CN), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenylenyl group, phenanthryl group, fluorenyl group, anthracenyl group, anthryl group, pyrenyl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, dibenzofuran group, It can be selected from the group consisting of a dibenzothiophene group, a phenanthrolinyl group, and a carbazolyl group.

[0070] In the chemical formula 1 according to the present invention, Y1 is O or S. This Y1-containing ring moiety is a dibenzo moiety having amphoteric physicochemical properties for holes and electrons, for example, a dibenzofuran moiety (Y1 = O) and a dibenzothiophene moiety ((Y1 = S).

[0071] These Y1-containing ring moieties can be directly bonded to the pyrimidine moiety or bonded via a separate linker group. In this case, the pyrimidine moiety can be introduced at various positions of the Y1-containing ring moiety. For example, the pyrimidine moiety can be bonded to the 2nd or 4th position of the Y1-containing ring moiety. In this case, the stability of the molecule can be increased, the compound can be structurally maintained as planar, and can be applied advantageously in terms of mobility.

[0072] According to an example of the present invention, the compound represented by Chemical Formula 1 may be a compound represented by Chemical Formula 2 or 3 below, depending on the bonding position of the Y1-containing ring moiety. However, the present invention is not limited thereto.

[0073]

[0074]

[0075] In the above chemical formulas 2 and 3

[0076] X1 to X3, Ar1, Y1, n, L1, o, p, q, a, b, c, d, e and R1 to R5 are each as defined in the above chemical formula 1.

[0077] In the above Y1-containing ring moiety, R1 may be substituted or unsubstituted with various substituents. If a is 0, the hydrogen of the Y1-containing ring moiety is unsubstituted with the substituent R1. On the other hand, when a is an integer from 1 to 7, specifically an integer from 1 to 4, the hydrogen of the Y1-containing ring moiety is substituted with the substituent R1. At this time, multiple R1s are the same or different from each other.

[0078] R1 is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 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 60Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., R1-R1, etc.) to form a condensed ring. Here, the heteroatom may be N, O, or S. Meanwhile, the condensed ring may be C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 A 5- to 60-membered fused heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered fused heteroaromatic ring), C3~C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0079] Specifically, R1 is hydrogen, deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, or condensed with an adjacent group (e.g., R1-R1) to form a C6~C 30 It can form a condensed aromatic ring or a condensed heteroaromatic ring of 5 to 30 members.

[0080] More specifically, R1 is selected from the group consisting of hydrogen, deuterium (D), cyano group (-CN), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group and fluorene group, or may be condensed with an adjacent group (e.g., R1-R1) to form a 6-18 membered fused aromatic ring or a 6-18 membered fused heteroaromatic ring containing a heteroatom of N, O or S.

[0081] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of the above R1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0082] According to an example, the Y1-containing ring moiety ( The moiety) may be selected from the group consisting of the following moieties Mo1-1 to Mo1-14, depending on the bonding position with L1 or the type of R1. However, it is not limited thereto.

[0083]

[0084]

[0085] In the above moieties Mo1-1 to Mo1-14,

[0086] Y1 is as defined in the above chemical formula 1,

[0087] a1 is an integer from 1 to 4, specifically a1 can be 1 or 2,

[0088] a2 is an integer from 1 to 3, specifically a2 can be 1,

[0089] a3 is an integer of 1 or 2, specifically a3 can be 1,

[0090] Multiple R1s are identical or different from each other,

[0091] R1 is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 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 40Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, and more specifically, it can be selected from the group consisting of a deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group,

[0092] Ring Cy1 is a condensed ring condensed on a benzene ring, and is selected from the group consisting of a 6- to 18-membered condensed aromatic ring and a 5- to 18-membered condensed heteroaromatic ring, and specifically may be selected from the group consisting of the following condensed rings Cy2-1 to Cy2-5.

[0093]

[0094] The above dotted line (---) indicates a portion bonded to the above moieties Mo1-1 to Mo1-14,

[0095] 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 R1, and the aromatic ring and heteroaromatic ring of the above ring Cy1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30and a heteroaryl group having 5 to 30 nuclear atoms, and is unsubstituted or substituted with one or more substituents selected from the group consisting of a deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group. In this case, when there are multiple substituents, they are the same or different from each other.

[0096] The above Y1-containing ring moiety can have various forms depending on the bonding position or type of R1. When R1 is substituted in the above Y1-containing ring moiety, the compound of the above chemical formula 1 not only has a high glass transition temperature, but also has a uniform morphology, thus having high crystallinity and packing density, and thus, thermal stability and electron transport properties can be further improved.

[0097] However, the introduction position of R1 into the Y1-containing ring moiety may vary depending on the bonding position of the Y1-containing ring moiety. For example, The moiety may be selected from the group consisting of the following moieties Mo2-1 to Mo2-95, but is not limited thereto.

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] In the above moieties Mo2-1 to Mo2-95,

[0109] * indicates a site that is combined with the above chemical formula 1,

[0110] Y1 is as defined in the above chemical formula 1,

[0111] Y2 and Y3 are the same or different, and are each independently O or S.

[0112] The aforementioned moieties Mo2-1 to Mo2-95 are each independently deuterium (D). Cyano group, C1~C 12 Alkyl group of C6~C 18 is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 18 nuclear atoms, and specifically, may be independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), cyano group (-CN), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzofuran group, dibenzothiophene group and fluorene group, and in this case, when there are multiple substituents, they are the same or different from each other.

[0113] The above-described Y1-containing ring moiety can be directly bonded to the pyrimidine moiety, or bonded via a separate linker. If n is 0, it means that L1 is a single bond (direct bond). On the other hand, if n is an integer from 1 to 3, L1 is a divalent linker group, C1~C 60 alkylene group, C6~C 60 Selected from the group consisting of arylene group and heteroarylene group having 5 to 60 nuclear atoms, specifically C1~C 30alkylene group, C6~C 30 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 30 nuclear atoms. Here, a plurality of L1s may be the same or different. In this way, when a separate linker exists between the Y1-containing ring moiety and the pyrimidine moiety, the HOMO region can be expanded to provide an advantage in the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through appropriate overlap of the HOMO-LUMO.

[0114] The alkylene group, arylene group and heteroarylene group of the above L1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0115] According to an example, the L1 may be a single bond or may be selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a fluorene group, and a combination thereof, but is not limited thereto. Here, the phenylene group, the biphenylene group, the terphenylene group, the naphthalene group, the phenanthrene group, the triphenylene group, and the fluorene group may be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), C1~C 12 Alkyl group of C6~C 10 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 10 nuclear atoms. Here, a plurality of L1s may be the same or different from each other.

[0116] In another example, L1 may be a single bond or may be selected from the group consisting of linker groups L1-1 to L1-3, and multiple L1s may be the same or different from each other, but is not limited thereto.

[0117]

[0118] In the above linker groups L1-1 to L1-3,

[0119] * is a portion that is combined with the above chemical formula 1,

[0120] Y4 is O, S or C(R6)(R7),

[0121] R6 and R7 are the same or different and each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 selected from the group consisting of arylamine groups, or forming a condensed ring with adjacent groups,

[0122] l is an integer from 0 to 4, specifically an integer from 0 to 2,

[0123] m is an integer from 0 to 6, specifically an integer from 0 to 3,

[0124] Multiple R's are the same or different from each other,

[0125] R is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups, specifically hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It can be selected from the group consisting of arylamine groups, and more specifically, hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, adamantyl group, norbornyl, bicyclo[1.1.0]butyl group, bicyclo[2.2.0]hexyl group, bicyclo[2.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[1.2.1]hexyl group, bicyclo[3.1.0]hexyl group, bicyclo[2.2.2]octyl group, bicyclo[3.1.1]heptyl group, It can be selected from the group consisting of a bicyclo[3.2.1]octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group.

[0126] According to another example, L1 may be a single bond or may be selected from the group consisting of linker groups L2-1 to L2-18, and multiple L1s may be the same or different from each other, but are not limited thereto.

[0127]

[0128]

[0129] In the above linker groups L2-1 to L2-18,

[0130] * is a portion that is combined with the above chemical formula 1,

[0131] l, m and R are as defined in the linker groups L1-1 to L1-3, respectively.

[0132] In the chemical formula 1 according to the present invention, o is an integer from 0 to 5, p is 0 or 1, q is 0 or 1, and provided that o+p+q≥2. Depending on o, p, and q, a plurality of aryl groups containing a terphenyl group are introduced to one side of the pyrimidine moiety. The plurality of aryl groups can control the stability of the compound molecule and the electron transport rate of the material.

[0133] For example, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 4 to 6, depending on o, p, and q. However, the present invention is not limited thereto.

[0134]

[0135]

[0136]

[0137] In the above chemical formulas 4 to 6,

[0138] X1 to X3, Ar1, Y1, n, L1, a, b, c, d, e, and R1 to R5 are each as defined in the above chemical formula 1,

[0139] o1 is an integer from 1 to 5, specifically 1 to 4.

[0140] In the present invention, the plurality of aryl groups bonded to one side of the pyrimidine moiety may be substituted or unsubstituted with various substituents, such as R2 to R5. If b is 0, hydrogen is unsubstituted with substituent R2, if c is 0, hydrogen is unsubstituted with substituent R3, if d is 0, hydrogen is unsubstituted with substituent R4, and if e is 0, hydrogen is unsubstituted with substituent R5. Meanwhile, when b is an integer from 1 to 4, specifically an integer of 1 or 2, hydrogen is substituted with a substituent R2, when c is an integer from 1 to 4, hydrogen is substituted with a substituent R3, when d is an integer from 1 to 5, specifically an integer from 1 to 3, hydrogen is substituted with a substituent R4, and when e is an integer from 1 to 5, specifically an integer from 1 to 3, hydrogen is substituted with a substituent R5. At this time, a plurality of R2s, a plurality of R3s, a plurality of R4s, and a plurality of R5s are the same as or different from each other.

[0141] The above R2 to R5 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or is condensed with adjacent groups (e.g., R2-R2, R3-R3, R4-R4, R5-R5, R2-R3, R3-R4, R4-R5, R1-R5, etc.) to form a condensed ring. Here, the heteroatom may be N, O, or S. Meanwhile, the condensed ring may be C3~C 60 Condensed aliphatic rings (specifically, C3~C 30 condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically, C6~C 30 A 5- to 60-membered fused heteroaromatic ring containing a heteroatom such as N, O or S (specifically, a 5- to 30-membered fused heteroaromatic ring), C3~C 60 It may be at least one selected from the group consisting of spiro rings and combinations thereof.

[0142] Specifically, R2 to R5 are the same or different from each other, and each independently represents hydrogen, deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, or condensed with an adjacent group (e.g., R1-R1) to form a C6~C 30 It can form a condensed aromatic ring or a condensed heteroaromatic ring of 5 to 30 members.

[0143] More specifically, R2 to R5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group, or may be condensed with an adjacent group (e.g., R1-R1) to form a 6- to 18-membered condensed aromatic ring or a 6- to 18-membered condensed heteroaromatic ring containing a heteroatom of N, O, or S.

[0144] At this time, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group and condensed ring of R2 to R5 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1 to C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and specifically, each independently selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxy group (-OH), C1~C 20 Alkyl group of C6~C 30 Aryl group, heteroaryl group with 5 to 30 nuclear atoms, C6~C 30 Arylphosphine oxide group and C6~C 30 It may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups. If there are multiple substituents, they may be the same or different.

[0145] The compound represented by Chemical Formula 1 according to the present invention can be modified in various ways depending on whether R1 is substituted or condensed, and o, p, or q. In one example, the compound represented by Chemical Formula 1 may be a compound represented by any one of the following Chemical Formulas 7 to 21. However, the present invention is not limited thereto.

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] In the above chemical formulas 7 to 21,

[0162] X1 to X3, Ar1, Y1, n, L1, b, c, d, e, and R2 to R5 are each as defined in the above chemical formula 1,

[0163] o1 is an integer from 1 to 5, specifically an integer from 1 to 4,

[0164] a1 is an integer from 1 to 4, specifically 1 or 2,

[0165] a2 is an integer from 1 to 3, specifically 1 or 2,

[0166] Multiple R1s are identical or different from each other,

[0167] R1 is deuterium (D), cyano group (-CN), C1~C 20 Alkyl group of C6~C 30 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, and specifically, it can be selected from the group consisting of deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group,

[0168] Ring Cy1 is a condensed ring condensed on a benzene ring, and is selected from the group consisting of a 6- to 18-membered condensed aromatic ring and a 5- to 18-membered condensed heteroaromatic ring, and specifically may be selected from the group consisting of the following condensed rings Cy2-1 to Cy2-5.

[0169]

[0170] The above dotted line (---) indicates a part that is combined with the chemical formulas 7 to 21,

[0171] The alkyl group, aryl group and heteroaryl group of the above R1 and the aromatic ring and heteroaromatic ring of the above ring Cy1 are each independently deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 20 Alkyl group of C6~C 30 and a heteroaryl group having 5 to 30 nuclear atoms, and is unsubstituted or substituted with one or more substituents selected from the group consisting of a deuterium (D), a cyano group (-CN), a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a fluorene group. In this case, when there are multiple substituents, they are the same or different from each other.

[0172] The compound represented by the chemical formula 1 of the present invention described above can be further specified as compounds 1 to 230 below. However, the compound represented by the chemical formula 1 of the present invention is not limited to those exemplified below.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] 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.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] 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 adamantyl.

[0186] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons in the ring, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0187] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0188] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom such as N, O, S, or Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms means the number of atoms forming the ring, i.e., the number of ring atoms.

[0189] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0190] 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.

[0191] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl.

[0192] In addition, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di-, and tri-arylsilyl.

[0193] In the present invention, “alkylboron group” means a boron group substituted with an alkyl having 1 to 40 carbon atoms, and “arylboron group” means a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0194] In the present invention, “alkylphosphinyl group” means a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl groups.

[0195] In addition, in the present invention, “arylphosphinyl group” means a phosphine group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0196] In the present invention, “arylphosphine oxide group” means a phosphine oxide group substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphine oxide groups.

[0197] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamine.

[0198] In the present invention, the "condensed ring" is a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclear atoms, a condensed heteroaromatic ring having 5 to 60 nuclear atoms, C3~C 60 It means a spyro ring or a combination thereof. Here, the nuclear atomic number means the number of atoms forming the ring, i.e. the number of ring atoms.

[0199]

[0200] Organic electroluminescent devices

[0201] Meanwhile, the present invention provides an organic electroluminescent device (hereinafter, 'organic EL device') comprising a compound represented by the above-described chemical formula 1.

[0202] Specifically, the organic electroluminescent device according to the present invention includes an anode (100), a cathode (200), and one or more organic layers (300) interposed between the anode and the cathode, as illustrated in FIGS. 1 to 3, and at least one of the one or more organic layers includes a compound represented by the chemical formula 1. At this time, the compound may be used alone, or two or more may be mixed and used.

[0203] The organic layer (300) of one or more layers may include one or more of a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport auxiliary layer (360), an electron transport layer (340), and an electron injection layer (350), and at least one of the organic layers (300) includes a compound represented by the chemical formula 1. Specifically, the organic layer including the compound of the chemical formula 1 may be at least one of an electron transport layer (340) and an electron transport auxiliary layer (360).

[0204] According to an example, the organic material layer of one or more layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may optionally further include an electron transport auxiliary layer. The electron transport layer includes a compound represented by the above chemical formula 1. In this case, the compound represented by the above chemical formula 1 is included in the organic electroluminescent device as an electron transport layer material. In such an organic electroluminescent device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound of the above chemical formula 1, and can also move quickly from the electron transport layer to the light emitting layer, so that the binding force between holes and electrons in the light emitting layer is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, brightness, etc. In addition, the compound of the above chemical formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of the organic electroluminescent device.

[0205] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer material known in the art.

[0206] In the present invention, 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 the electron transport material that can be used include an oxazole compound, an isoxazole compound, a triazole compound, an isothiazole compound, an oxadiazole compound, a thiadiazole compound, a perylene compound, and an aluminum complex (e.g., Alq). 3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These can be used alone or in combination of two or more.

[0207] 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.

[0208] According to another example, the organic layer of one or more layers includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer includes a compound represented by the chemical formula 1. At this time, the compound represented by the chemical formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound of the chemical formula 1 has a high triplet energy. Therefore, when the compound of the chemical formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device can be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of the chemical formula 1 can prevent excitons or holes generated in the light emitting layer from diffusing to the electron transport layer adjacent to the light emitting layer. Therefore, the number of excitons contributing to light emission in the light emitting layer increases, so that the light emitting efficiency of the device can be improved, and the durability and stability of the device can be improved, so that the lifespan of the device can be efficiently increased.

[0209] The compound of chemical formula 1 may be used alone or in combination with an electron transport layer auxiliary layer material known in the art.

[0210] In the present invention, the electron transport auxiliary layer material that can be mixed with the compound of the above chemical formula 1 includes electron transport materials commonly known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and heterocyclic derivatives containing nitrogen, but is not limited thereto.

[0211] The structure of the organic electroluminescent device of the present invention described above is not particularly limited, but for example, an anode (100), one or more organic layers (300), and a cathode (200) may be sequentially laminated on a substrate (see FIGS. 1 to 3). In addition, although not shown, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0212] According to an example, the organic electroluminescent device may have a structure in which an anode (100), a hole injection layer (310), a hole transport layer (320), a light-emitting layer (330), an electron transport layer (340), and a cathode (200) are sequentially laminated on a substrate, as illustrated in FIG. 1. Optionally, as illustrated in FIG. 2, an electron injection layer (350) may be positioned between the electron transport layer (340) and the cathode (200). In addition, an electron transport auxiliary layer (360) may be positioned between the light-emitting layer (330) and the electron transport layer (340) (see FIG. 3).

[0213] The organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers (300) [e.g., the light-emitting layer (330), the electron transport layer (340), or the electron transport auxiliary layer (360)] includes a compound represented by the chemical formula 1.

[0214] 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.

[0215] The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0216] Examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0217] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0218] In addition, the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and conventional materials known in the art can be used.

[0219]

[0220] 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.

[0221] [Preparation Example 1] - Synthesis of Compound Core 1

[0222]

[0223] 100 g (332.0 mmol) of 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine, 100.4 g (348.6 mmol) of (6-phenyldibenzo[b,d]furan-2-yl)boronic acid, 419.2 g (16.6 mmol) of Pd(PPh3), and 91.8 g (664.0 mmol) of K2CO3 were added to 600 ml of THF and 300 ml of H2O, and heated and stirred under reflux for 5 hours. After completion of the reaction, the organic layer was extracted with toluene, dried with MgSO4, and filtered. After filtering, the solvent of the organic layer was concentrated under reduced pressure, purified by column chromatography using dichloromethane and hexane, and the solid was filtered and dried to obtain 122.2 g (yield 72.3%) of compound Core 1.

[0224] Mass: [(M+H) + ] : 508

[0225]

[0226] [Preparation Example 2] - Synthesis of Compound Core 2

[0227]

[0228] Except that 100 g (265.1 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(4-chlorophenyl)pyrimidine, 59.0 g (278.3 mmol) of dibenzo[b,d]furan-2-ylboronic acid, 15.3 g (13.3 mmol) of Pd(PPh3), 73.3 g (530.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 134.9 g (yield 76.5%) of compound Core 2.

[0229] Mass: [(M+H) + ] : 508

[0230]

[0231] [Preparation Example 3] - Synthesis of Compound Core 3

[0232]

[0233] Except that 100 g (332.0 mmol) of 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine, 73.9 g (348.6 mmol) of dibenzo[b,d]furan-4-ylboronic acid, 19.2 g (16.6 mmol) of Pd(PPh3), 91.8 g (664.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 116.7 g (yield 81.2%) of compound Core 3.

[0234] Mass: [(M+H) + ] : 432

[0235]

[0236] [Preparation Example 4] - Synthesis of Compound Core 4

[0237]

[0238] Except that 150 g (498.1 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine, 193.6 g (523.0 mmol) of 2-(3-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 428.8 g (24.9 mmol) of Pd(PPh3), 137.7 g (996.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 176.7 g (yield 69.7%) of compound Core 4.

[0239] Mass: [(M+H) + ] : 508

[0240]

[0241] [Preparation Example 5] - Synthesis of Compound Core 5

[0242]

[0243] Except that 100 g (332 mmol) of 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine, 73.9 g (348.6 mmol) of dibenzo[b,d]furan-2-ylboronic acid, 19.2 g (16.6 mmol) of Pd(PPh3), 91.8 g (664.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 123.2 g (yield 85.7%) of compound Core 5.

[0244] Mass: [(M+H) + ] : 432

[0245]

[0246] [Preparation Example 6] - Synthesis of Compound Core 6

[0247]

[0248] Except that 100 g (332 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidin, 73.9 g (348.6 mmol) of dibenzo[b,d]furan-2-ylboronic acid, 19.2 g (16.6 mmol) of Pd(PPh3), 91.8 g (664.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 121.9 g (yield 84.8%) of compound Core 6.

[0249] Mass: [(M+H) + ] : 432

[0250]

[0251] [Preparation Example 7] - Synthesis of Compound Core 7

[0252]

[0253] Except that 100 g (332 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidin, 129.1 g (348.6 mmol) of 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 19.2 g (16.6 mmol) of Pd(PPh3), 91.8 g (664.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 130.3 g (yield 77.1%) of compound Core 7.

[0254] Mass: [(M+H) + ] : 508

[0255]

[0256] [Preparation Example 8] - Synthesis of Compound Core 8

[0257]

[0258] Except that 100 g (265.1 mmol) of 4-chloro-6-(3'-chloro-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine, 59.0 g (278.3 mmol) of dibenzo[b,d]furan-2-ylboronic acid, 15.3 g (13.3 mmol) of Pd(PPh3), 73.3 g (530.1 mmol) of K2CO3, 600 ml of THF, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 96.7 g (yield 71.7%) of compound Core 8.

[0259] Mass: [(M+H) + ] : 508

[0260]

[0261] [Preparation Example 9] - Synthesis of Compound Core 9

[0262] <Step 1> Synthesis of 2-(4''-chloro-[1,1':3',1''-terphenyl]-4-yl)dibenzo[b,d]furan

[0263]

[0264] Except that 110 g (297.1 mmol) of 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 83.5 g (311.9 mmol) of 3-bromo-4'-chloro-1,1'-biphenyl, 17.2 g (14.9 mmol) of Pd(PPh3), 82.1 g (594.2 mmol) of K2CO3, 660 ml of Tol, 330 ml of EtOH, and 330 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 100.4 g (yield 78.4%) of 2-(4''-chloro-[1,1':3',1''-terphenyl]-4-yl)dibenzo[b,d]furan.

[0265] Mass: [(M+H) + ] : 430

[0266] <Step 2> Synthesis of 2-(4''-(dibenzo[b,d]furan-2-yl)-[1,1':3',1''-terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0267]

[0268] <Step 1> 100 g (232 mmol) of 2-(4''-chloro-[1,1':3',1''-terphenyl]-4-yl)dibenzo[b,d]furan synthesized in 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 70.7 g (278 mmol), Pd(dppf)Cl2 8.5 g (12 mmol), KOAc 68.3 g (696 mmol), Xphos 11.1 g (23 mmol) were added to 1000 ml of 1,4-Dioxane and heated under reflux for 6 hours. After completion of the reaction, 1,4-Dioxane was removed by concentration under reduced pressure, and then purified by column chromatography using dichloromethane and hexane, and the solid was filtered to obtain 83.5 g (yield 68.9%) of 2-(4''-(dibenzo[b,d]furan-2-yl)-[1,1':3',1''-terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0269] Mass: [(M+H) + ] : 522

[0270] <Step 3> Synthesis of compound Core 9

[0271]

[0272] Except that instead of the materials used in Preparation Example 1, 45.5 g (151.1 mmol) of 4-chloro-6-(3-chlorophenyl)-2-phenylpyrimidine, 83.0 g (158.6 mmol) of 2-(4''-(dibenzo[b,d]furan-2-yl)-[1,1':3',1''-terphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in <Step 2>, 48.7 g (7.6 mmol) of Pd(PPh3), 41.8 g (302.2 mmol) of K2CO3, 273 ml of Tol, and 136 ml of H2O were used, respectively, and the same procedure as in Preparation Example 1 was carried out. 4-(3-chlorophenyl)-6-(4''-(dibenzo[b,d]furan-2-yl)-[1,1':3',1''-terphenyl]-4-yl)-2-phenylpyrimidine 54.2 g (yield 54.3%) was obtained.

[0273] Mass: [(M+H) + ] : 660

[0274]

[0275] [Preparation Example 10] - Synthesis of Compound Core 10

[0276]

[0277] Except that 100 g (332.0 mmol) of 4-chloro-6-(4-chlorophenyl)-2-phenylpyrimidine, 79.5 g (348.6 mmol) of dibenzo[b,d]thiophen-2-ylboronic acid, 19.2 g (16.6 mmol) of Pd(PPh3), 91.8 g (664.1 mmol) of K2CO3, 600 ml of Tol, and 300 ml of H2O were used instead of the materials used in Preparation Example 1, the same procedure as in Preparation Example 1 was performed to obtain 99.1 g (yield 66.5%) of 4-(4-chlorophenyl)-6-(dibenzo[b,d]thiophen-2-yl)-2-phenylpyrimidine.

[0278] Mass: [(M+H) + ] : 448

[0279]

[0280] [Synthesis Example 1] Synthesis of Compound 1

[0281]

[0282] [Preparation Example 1] Compound Core1 25.0 g (1 eq, 49.0 mmol), 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-3'-carbonitrile 20.6 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 3.0 mmol) were added to 150 ml of toluene, 75 ml of EtOH, and 75 ml of H2O, and reacted by heating and refluxing for 4 hours. After completion of the reaction, the organic layer was extracted with toluene, 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 22.7 g (yield 63.5%) of compound 1.

[0283] Mass: [(M+H) + ] : 727

[0284]

[0285] [Synthesis Example 2] Synthesis of Compound 4

[0286]

[0287] [Preparation Example 2] Compound Core 2 25.0 g (1 eq, 49.1 mmol), 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':3',1''-terphenyl]-2-carbonitrile 20.6 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 3.0 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 4 20.1 g (yield 56.1%).

[0288] Mass: [(M+H) + ] : 727

[0289]

[0290] [Synthesis Example 3] Synthesis of Compound 7

[0291]

[0292] [Preparation Example 3] Compound Core 3 25.0 g (1eq, 57.7 mmol), 2-([1,1':2',1'':2'',1'''-quaterphenyl]-3''-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 27.5 g (1.1eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03eq, 0.17 mmol), Cs2CO3 37.6 g (2.0eq, 115.5 mmol), Xphos 1.7 g (0.6eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain Compound 7 22.9 g (yield 55.9%). Got it.

[0293] Mass: [(M+H) + ] : 702

[0294]

[0295] [Synthesis Example 4] Synthesis of Compound 48

[0296]

[0297] [Preparation Example 4] Compound Core 4 25.0 g (1 eq, 49.1 mmol), 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-4''-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 27.5 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain compound 48 22.9 g (Yield 55.9%) was obtained.

[0298] Mass: [(M+H) + ] : 702

[0299]

[0300] [Synthesis Example 5] Synthesis of Compound 50

[0301]

[0302] [Preparation Example 4] Compound Core 4 25.0 g (1 eq, 49.1 mmol), 2-([1,1':3',1''-terphenyl]-5'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 19.2 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 50 24.9 g (yield 72.2%).

[0303] Mass: [(M+H) + ] : 702

[0304]

[0305] [Synthesis Example 6] Synthesis of Compound 74

[0306]

[0307] [Preparation Example 5] Compound Core 5 25.0 g (1 eq, 57.7 mmol), 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)-1,3,2-dioxaborolane 27.5 g (1.1 eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 75 30.6 g (yield 75.4%).

[0308] Mass: [(M+H) + ] : 702

[0309]

[0310] [Synthesis Example 7] Synthesis of Compound 75

[0311]

[0312] [Preparation Example 5] Compound Core 5 25.0 g (1 eq, 57.7 mmol), 4,4,5,5-tetramethyl-2-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane 27.5 g (1.1 eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 104 24.9 g (yield 61.3%).

[0313] Mass: [(M+H) + ] : 702

[0314]

[0315] [Synthesis Example 8] Synthesis of Compound 104

[0316]

[0317] [Preparation Example 6] Compound Core 6 25.0 g (1 eq, 57.7 mmol), 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane 27.5 g (1.1 eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 104 23.5 g (yield 57.9%).

[0318] Mass: [(M+H) + ] : 702

[0319]

[0320] [Synthesis Example 9] Synthesis of Compound 107

[0321]

[0322] [Preparation Example 6] Compound Core 6 25.0 g (1 eq, 57.7 mmol), 2,4-diphenyl-6-(5'-phenyl-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-3-yl)-1,3,5-triazine 42.2 g (1.1 eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain the compound 107 23.0 g (yield 42.6%) was obtained.

[0323] Mass: [(M+H) + ] : 933

[0324]

[0325] [Synthesis Example 10] Synthesis of Compound 115

[0326]

[0327] [Preparation Example 7] Compound Core 7 25.0 g (1 eq, 49.1 mmol), 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)-1,3,2-dioxaborolane 23.4 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 115 19.9 g (yield 51.9%).

[0328] Mass: [(M+H) +] : 778

[0329]

[0330] [Synthesis Example 11] Synthesis of Compound 120

[0331]

[0332] [Preparation Example 4] Compound Core 4 25.0 g (1 eq, 49.1 mmol), 4,4,5,5-tetramethyl-2-(5'-phenyl-[1,1':2',1''-terphenyl]-3'-yl)-1,3,2-dioxaborolane 23.4 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 120 20.2 g (yield 52.7%).

[0333] Mass: [(M+H) + ] : 778

[0334]

[0335] [Synthesis Example 12] Synthesis of Compound 121

[0336]

[0337] [Preparation Example 4] Compound Core 4 25.0 g (1 eq, 49.1 mmol), 4,4,5,5-tetramethyl-2-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane 23.4 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 121 18.5 g (yield 48.3%).

[0338] Mass: [(M+H) + ] : 778

[0339]

[0340] [Synthesis Example 13] Synthesis of Compound 143

[0341]

[0342] [Preparation Example 8] Compound Core 8 25.0 g (1 eq, 49.1 mmol), 4,4,5,5-tetramethyl-2-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane 23.4 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 121 20.2 g (yield 52.9%).

[0343] Mass: [(M+H) + ] : 778

[0344]

[0345] [Synthesis Example 14] Synthesis of Compound 149

[0346]

[0347] [Preparation Example 5] Compound Core 5 25.0 g (1 eq, 57.7 mmol), 2-(3',5'-diphenyl -[1,1':2',1''-terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 32.3 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 149 18.2 g (yield 40.5%).

[0348] Mass: [(M+H) + ] : 778

[0349]

[0350] [Synthesis Example 15] Synthesis of Compound 154

[0351]

[0352] [Preparation Example 4] Compound Core 4 25.0 g (1 eq, 49.1 mmol), 4,4,5,5-tetramethyl-2-(3',4',5'-triphenyl-[1,1':2',1''-terphenyl]-4-yl)-1,3,2-dioxaborolane 31.6 g (1.1 eq, 54.0 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.15 mmol), Cs2CO3 32.0 g (2.0 eq, 98.2 mmol), Xphos 1.4 g (0.6 eq 2.9 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain Compound 154 18.6 g (yield 40.8%). Got it.

[0353] Mass: [(M+H) + ] : 930

[0354]

[0355] [Synthesis Example 16] Synthesis of Compound 197

[0356]

[0357] [Preparation Example 9] Compound Core 9 25.0 g (1 eq, 37.8 mmol), 4,4,5,5-tetramethyl-2-(6'-phenyl-[1,1':2',1''-terphenyl]-4'-yl)-1,3,2-dioxaborolane 18.0 g (1.1 eq, 41.6 mmol), Pd(OAc) 20.3 g (0.03 eq, 0.11 mmol), Cs2CO3 24.6 g (2.0 eq, 75.6 mmol), Xphos 1.1 g (0.6 eq 2.3 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was performed to obtain Compound 197 15.3 g (yield 43.4%).

[0358] Mass: [(M+H) + ] : 930

[0359]

[0360] [Synthesis Example 17] Synthesis of Compound 209

[0361]

[0362] [Preparation Example 10] Compound Core 10 25.0 g (1 eq, 55.7 mmol), 2,4-diphenyl-6-(4'-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':3',1''-terphenyl]-4-yl)-1,3,5-triazine 40.6 g (1.1 eq, 61.3 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 36.3 g (2.0 eq, 111.4 mmol), Xphos 1.6 g (0.6 eq 3.3 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain the compound 209 21.1 g (yield 39.8%) was obtained.

[0363] Mass: [(M+H) + ] : 949

[0364]

[0365] [Synthesis Example 18] Synthesis of Compound 213

[0366]

[0367] [Preparation Example 3] Compound Core 3 25.0 g (1 eq, 57.7 mmol), (2-(4'-(dimethylphosphoryl)-[1,1':2',1''-terphenyl]-4-yl)-4,5,5-trimethyl-1,3,2-dioxaborolan-4-yl)methylium 27.4 g (1.1 eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 37.6 g (2.0 eq, 115.5 mmol), Xphos 1.7 g (0.6 eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain compound 213 26.5 g (yield) 65.2%) was obtained.

[0368] Mass: [(M+H) + ] : 702

[0369]

[0370] [Synthesis Example 19] Synthesis of Compound 216

[0371]

[0372] [Preparation Example 5] Compound Core 5 25.0 g (1eq, 57.7 mmol), 2-([1,1':2',1'':2'',1'''-quaterphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 27.5 g (1.1eq, 63.5 mmol), Pd(OAc) 20.4 g (0.03eq, 0.17 mmol), Cs2CO3 37.6 g (2.0eq, 115.5 mmol), Xphos 1.7 g (0.6eq 3.5 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain Compound 216 27.8 g (yield 68.4%). Got it.

[0373] Mass: [(M+H) + ] : 702

[0374]

[0375] [Synthesis Example 20] Synthesis of Compound 218

[0376]

[0377] [Preparation Example 10] Compound Core 10 25.0 g (1 eq, 55.7 mmol), 2-([1,1':2',1'':2'',1'''-quaterphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 26.5 g (1.1 eq, 61.3 mmol), Pd(OAc) 20.4 g (0.03 eq, 0.17 mmol), Cs2CO3 36.3 g (2.0 eq, 111.4 mmol), Xphos 1.6 g (0.6 eq 3.3 mmol), Toluene 150 ml, EtOH 75 ml, and H2O 75 ml were used, respectively, and the same procedure as in Synthesis Example 1 was carried out to obtain Compound 218 23.9 g (yield 59.7 %) was obtained.

[0378] Mass: [(M+H) + ] : 718

[0379]

[0380] [Example 1] Fabrication of a blue organic electroluminescent device

[0381] After the compound 1 synthesized in Synthesis Example 1 was purified by sublimation to high purity using a commonly known method, a blue organic electroluminescent device was manufactured as follows.

[0382] 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.

[0383] On the ITO transparent electrode prepared as above, an organic electroluminescent device was fabricated by stacking 98 wt% HT-1 + 2 wt% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / 98 wt% BH + 2 wt% BD (200 Å) / ET-2 (50 Å) / compound 1: LiQ = 1:1 weight ratio (300 Å) / LiF (10 Å) / Al (1000 Å) in that order. The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2 and LiQ used here are as follows.

[0384]

[0385]

[0386] [Examples 2-5] Fabrication of blue organic electroluminescent devices

[0387] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the materials described in Table 1 below were used instead of Compound 1 used as an electron transport layer material in Example 1.

[0388]

[0389] [Comparative Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0390] A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound ET-1 was used instead of Compound 1 used as an electron transport layer material in Example 1. The structure of Compound ET-1 used here is as follows.

[0391]

[0392]

[0393] [Evaluation Example 1]

[0394] For each blue organic electroluminescent device manufactured in Examples 1 to 5 and Comparative Example 1, 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.

[0395] Sample Electron Transport Layer Material Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 1 Compound 14.6 460 6.4 Example 2 Compound 44.2 461 6.2 Example 3 Compound 1074.3 460 6.3 Example 4 Compound 2094.5 459 6.6 Example 5 Compound 2134.4 461 6.4 Comparative Example 1 ET-14.9 460 5.8

[0396] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 5 using the compound according to the present invention as an electron transport layer material exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent device of Comparative Example 1 using a conventional electron transport layer material (compound ET-1) as an electron transport layer.

[0397]

[0398] [Example 6] Fabrication of a blue organic electroluminescent device

[0399] After the synthetic compound 7 was purified by sublimation to a high purity using a conventionally known method, a blue organic electroluminescent device was manufactured as follows.

[0400] 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.

[0401] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking 98 wt% HT-1 + 2 wt% HAT-CN (100 Å) / HT-1 (1400 Å) / HT-2 (50 Å) / 98 wt% BH + 2 wt% BD (200 Å) / Compound 1 (50 Å) / ET-1: LiQ = 1:1 weight ratio (300 Å) / LiF (10 Å) / Al (1000 Å) in that order. The structures of HT-1, HAT-CN, HT-2, BH, BD, ET-2 and LiQ used here are the same as those described in Example 1, and the structure of ET-1 is the same as those described in Comparative Example 1, and therefore, is omitted.

[0402]

[0403] [Examples 7-20] Fabrication of blue organic electroluminescent devices

[0404] A blue organic electroluminescent device was manufactured in the same manner as in Example 6, except that the materials described in Table 2 below were used instead of compound 7 used as the electron transport auxiliary layer material in Example 6.

[0405]

[0406] [Comparative Examples 2-4] Fabrication of Blue Organic Electroluminescent Devices

[0407] A blue organic electroluminescent device was manufactured in the same manner as in Example 6, except that compounds ET-2 to ET-4 were each deposited at 50 Å instead of compound 7 used as an electron transport auxiliary layer material in Example 6. The structures of compounds ET-2, ET-3, and ET-4 used here are as follows.

[0408]

[0409]

[0410] [Evaluation Example 2]

[0411] For the organic electroluminescent devices manufactured in Examples 6 to 20 and Comparative Examples 2 to 4, 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.

[0412] Sample Electron Transport Auxiliary Layer Material Driving Voltage (V) EL Peak (nm) Current Efficiency (cd / A) Example 6 Compound 74.34616.4 Example 7 Compound 484.24606.5 Example 8 Compound 504.44616.7 Example 9 Compound 744.34626.9 Example 10 Compound 754.24597.0 Example 11 Compound 1044.44586.6 Example 12 Compound 1154.14626.8 Example 13 Compound 1204.24636.3 Example 14 Compound 1214.44586.4 Example 15 Compound 1434.24606.4 Example Compound 16 1494.04606.6 Example 17 Compound 1544.34597.0 Example 18 Compound 1974.44606.5 Example 19 Compound 2163.84606.3 Example 20 Compound 2184.24626.5 Comparative Example 2 ET-24.74605.8 Comparative Example 3 ET-34.84615.9 Comparative Example 4 ET-44.64606.0

[0413] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 6 to 20 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 organic electroluminescent devices of Comparative Examples 2 to 4.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] (In the above chemical formula 1, X1 to X3 are the same or different, and are each independently N or C(Ar2), provided that two of X1 to X3 are N, Ar1 and Ar2 are the same or different from each other, and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxy 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 and C6~C 60 is selected from the group consisting of arylamine groups, Y1 is O or S, n is an integer from 0 to 3, Multiple L1s are identical or different from each other, L1 is a single bond, or C1~C 60 Alkylene group, C6~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, o is an integer from 0 to 5, p is 0 or 1, q is 0 or 1, However, o+p+q≥2, a is an integer from 0 to 7, b is an integer from 0 to 4, c is an integer from 0 to 4, d and e are integers from 0 to 5, respectively. R1 to R5 are the same or different and each independently represents hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group 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 and C6~C 60 selected from the group consisting of arylamine groups, or condensed with an adjacent group to form a condensed ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group of the above Ar1 and Ar2, the alkylene group, arylene group and heteroarylene group of the above L1, 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, arylamine group and condensed ring of the above R1 to R5 are each independently selected from the group consisting of deuterium (D), halogen, cyano group, Nitro group, amino group, hydroxyl group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group 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 and C6~C 60 (Substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they are the same or different from each other).

2. In paragraph 1, Above A compound wherein the moiety is selected from the group consisting of the following moieties Az-1 to Az-3: (In the above moieties Az1-1 to Az1-3, Ar1 and Ar2 are each as defined in Article 1).

3. In paragraph 1, A compound wherein Ar1 is selected from the group consisting of the following substituents S1-1 to S1-16: (In the above substituents S1-1 to S1-16, f is an integer from 0 to 5, g is an integer from 0 to 4, h is an integer from 0 to 7, i is an integer from 0 to 6, j is an integer from 0 to 9, k is an integer from 0 to 11, Multiple R's are identical or different from each other, R is deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 and C6~C 60 (selected from the group consisting of arylamine groups).

4. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by the following chemical formula 2 or 3: [Chemical formula 2] [Chemical Formula 3] (In the above chemical formulas 2 and 3 X1 to X3, Ar1, Y1, n, L1, o, p, q, a, b, c, d, e, and R1 to R5 are each as defined in Article 1.

5. In paragraph 1, Above A compound wherein the moiety is selected from the group consisting of the following moieties Mo1-1 to Mo1-14: (In the above moieties Mo1-1 to Mo1-14, Y1 is as defined in Article 1, a1 is an integer from 1 to 4, a2 is an integer from 1 to 3, a3 is an integer of 1 or 2, Multiple R1s are identical or different from each other, R1 is hydrogen, deuterium (D), halogen, cyano group (-CN), nitro group (-NO2), amino group (-NH2), hydroxyl group (-OH), C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group 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 and C6~C 60 is selected from the group consisting of arylamine groups, Ring Cy1 is selected from the group consisting of 6- to 18-membered condensed aromatic rings and 5- to 18-membered condensed heteroaromatic rings, 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 R1, and the condensed aromatic ring and condensed heteroaromatic ring of the above ring Cy1 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy group, C1~C 20 Alkyl group of C6~C 30 (is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, and when there are multiple substituents, they are the same or different from each other).

6. In paragraph 1, Multiple L1s are identical or different from each other, A compound wherein L1 is a single bond or is selected from the group consisting of the following linker groups L1-1 to L1-3: (In the above linker groups L1-1 to L1-3, Y4 is O, S or C(R6)(R7), R6 and R7 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 and C6~C 60 selected from the group consisting of arylamine groups, or forming a condensed ring with adjacent groups, l is an integer from 0 to 4, m is an integer from 0 to 6, Multiple R's are identical or different from each other, R is hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, hydroxy 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 and C6~C 60 (selected from the group consisting of arylamine groups).

7. In paragraph 1, The compound represented by the above chemical formula 1 is a compound represented by any one of the following chemical formulas 4 to 6: [Chemical Formula 4] [Chemical Formula 5] [Chemical formula 6] (In the above chemical formulas 4 to 6, X1 to X3, Ar1, Y1, n, L1, a, b, c, d, e, and R1 to R5 are each as defined in Article 1, o1 is an integer from 1 to 5).

8. 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 21: [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical formula 20] [Chemical Formula 21] (In the chemical formulas 7 to 21 above, X1 to X3, Ar1, Y1, n, L1, b, c, d, e, and R1 to R5 are each as defined in Article 1, o1 is an integer from 1 to 5, a1 is an integer from 1 to 4, a2 is an integer from 1 to 3, Multiple R1s are identical or different from each other, Ring Cy1 is selected from the group consisting of 6- to 18-membered aromatic rings and 5- to 18-membered heteroaromatic rings, The aromatic ring and heteroaromatic ring of the above ring Cy1 are each independently deuterium (D), halogen, cyano group, nitro group, amino group, hydroxyl group, C1~C 20 Alkyl group of C6~C 30 (is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms, and when there are multiple substituents, they are the same or different from each other).

9. In paragraph 1, The compound represented by the above chemical formula 1 is a compound selected from the group consisting of compounds 1 to 230 below: .

10. Anode; cathode; comprising at least one organic layer interposed between the anode and the cathode, An organic electroluminescent device, wherein at least one of the organic layers of one or more layers comprises an organic compound as described in any one of claims 1 to 9.

11. In paragraph 10, An organic electroluminescent device, wherein the organic layer containing the organic compound is an electron transport layer or an electron transport auxiliary layer.

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