Organic compound and organic electroluminescent element using same

Abstract

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent element using the same. The present invention relates to a compound having excellent thermal stability, electrochemical stability, light-emitting ability, and hole / electron transport ability, and an organic electroluminescent element having improved characteristics such as light-emitting efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers.

Description

Technical Field

[0001] The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent chemical structure stability, thermal stability, electrochemical stability, and hole-transporting ability, and an organic electroluminescent device in which characteristics such as luminous efficiency, driving voltage, and lifespan are improved by including the compound in one or more organic layers. Background Art

[0002] When an electric current or voltage is applied to two electrodes of an organic electroluminescent device (hereinafter referred to as "organic EL device"), holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons transition to the ground state, light is emitted. At this time, the materials used for the organic layer can be classified into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc. according to their functions.

[0003] The light-emitting materials of the organic EL device can be classified into blue, green, and red light-emitting materials according to the emission color. In addition, yellow and orange light-emitting materials required for presenting more natural colors can be classified. In addition, in order to increase the luminous efficiency through increased color purity and energy transfer, as the light-emitting material, a host / dopant system can be used. The dopant materials can be classified into fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically increase the luminous efficiency by up to four times compared to fluorescence, not only phosphorescent dopants but also phosphorescent host materials have attracted attention.

[0004] So far, NPB, BCP, Alq3, etc. represented by the following chemical formulas have been widely known as the hole-injecting layer, hole-transporting layer, hole-blocking layer, and electron-transporting layer. Regarding the light-emitting materials, anthracene derivatives have been reported as fluorescent dopant / host materials. In particular, as phosphorescent materials having great advantages in terms of efficiency improvement among the light-emitting materials, metal coordination compounds containing Ir such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2 have been used as blue, green, and red dopant materials. Currently, CBP exhibits excellent characteristics as a phosphorescent host material.

[0005] However, although the conventional materials have advantages in terms of luminous characteristics, they have a low glass transition temperature and very poor thermal stability, so the lifespan of the organic EL device cannot reach a satisfactory level. Therefore, it is necessary to develop organic layer materials with excellent performance. Summary of the Invention

[0006] Technical Problem

[0007] An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent element and has excellent thermal stability, electrochemical stability, and hole transport ability and can be used as a hole transport layer material.

[0008] Another object of the present invention is to provide an organic electroluminescent element that contains the above novel organic compound, exhibits a low driving voltage and high luminous efficiency, and has an improved lifespan.

[0009] Means for Solving the Problem

[0010] To achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0011] [Chemical Formula 1]

[0012]

[0013] (In the above Chemical Formula 1,

[0014] n ≥ 1,

[0015] X1 is O or S,

[0016] Ring CyA is an aromatic ring having 6 to C 30 and

[0017] n1 to n3 are each an integer from 0 to 3,

[0018] L1 to L3 are the same as or different from each other and are each independently a single bond or selected from the group consisting of an arylene having 6 to C 30 and a heteroarylene having 5 to 30 ring nuclei,

[0019] m1 is an integer from 0 to 8,

[0020] m2 is an integer from 0 to 23,

[0021] R1, R2, Ar1, and Ar2 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, an alkyl group having 1 to C 40 an alkenyl group having 2 to C 40 an alkynyl group having 2 to C 40 a cycloalkyl group having 3 to C 40 a heterocycloalkyl group having 3 to 40 ring nuclei, an aryl group having 6 to C 60 a heteroaryl group having 5 to 60 ring nuclei, an alkoxy group having 1 to C 40 an aryloxy group having 6 to C 60 an alkylsilyl group having 1 to C 40 an arylsilyl group having 6 to C 60aryl silyl groups having from C1 to C 40 alkyl boronic groups having from C6 to C 60 aryl boronic groups having from C6 to C 60 aryl phosphino groups having from C6 to C 60 aryl phosphine oxide groups having from C6 to C 60 aryl amino groups having from C6 to C 60 a group consisting of (aryl)(heteroaryl)amino groups and heteroaryl amino groups having from 5 to 60 ring atoms, or condensed with an adjacent group to form a condensed ring,

[0022] The arylene and heteroarylene groups of L1 to L3 above, and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkyl silyl, aryl silyl, alkyl boronic, aryl boronic, aryl phosphino, aryl phosphine oxide, aryl amino, (aryl)(heteroaryl)amino, and heteroaryl amino groups of R1, R2, Ar1, and Ar2 above are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1 to C 40 alkyl groups having from C1 to C 40 alkenyl groups having from C2 to C 40 alkynyl groups having from C2 to C 40 cycloalkyl groups having from C3 to C 60 heterocycloalkyl groups having from 3 to 40 ring atoms, aryl groups having from C6 to C 40 heteroaryl groups having from 5 to 60 ring atoms, alkoxy groups having from C1 to C 60 aryloxy groups having from C6 to C 40 alkyl silyl groups having from C1 to C 60 aryl silyl groups having from C6 to C 40 alkyl boronic groups having from C1 to C 60 aryl boronic groups having from C6 to C 60 aryl phosphino groups having from C6 to C 60 aryl phosphine oxide groups having from C6 to C 60 aryl amino groups having from C6 to C 60 (aryl)(heteroaryl)amino groups having from C6 to C and one or more substituents selected from the group consisting of heteroaryl amino groups having from 5 to 60 ring atoms are substituted or unsubstituted, and when there are a plurality of the above substituents, they may be the same or different).

[0023] Furthermore, the present invention provides an organic electroluminescent device including an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, and at least one of the one or more organic layers contains the compound represented by Chemical Formula 1 above.

[0024] According to one example, the organic layer containing the above organic compound may be a hole transport layer.

[0025] Advantages of the Invention

[0026] Due to excellent thermal stability, electrochemical stability, and hole transport ability, the compounds of the present invention can be effectively used as materials for the organic layer of organic electroluminescent devices. In particular, when the compounds of the present invention are used as materials for the hole transport layer, organic electroluminescent devices with excellent luminescence performance, low driving voltage, high efficiency, and long lifespan characteristics compared to conventional materials can be manufactured. Furthermore, full-color display panels with improved performance and lifespan can also be manufactured.

[0027] The effects of the present invention are not limited to the above-exemplified content, and more diverse effects are included in this specification. Brief Description of the Drawings

[0028] Figure 1 FIG. is a cross-sectional view schematically showing an example of an organic electroluminescent device of the present invention.

[0029] Figure 2 FIG. is a cross-sectional view schematically showing another example of an organic electroluminescent device of the present invention.

[0030] <Reference Signs>

[0031] 100: Anode, 200: Cathode,

[0032] 300: Organic layer, 310: Hole injection layer,

[0033] 320: Hole transport layer, 330: Light-emitting layer,

[0034] 340: Electron transport layer, 350: Electron injection layer. Detailed Description of the Invention

[0035] <Novel Compounds>

[0036] The compounds of the present invention contain an amino group substituted with an aryl and / or heteroaryl group, and a spiro ring directly connected to or connected to the above amino group through a linking group (e.g., phenylene, etc.). Moreover, at least one deuterium (D) must be included in the above molecular structure, and is represented by the following Chemical Formula 1. Such compounds of Chemical Formula 1 not only have excellent electrochemical stability, thermal stability, and carrier transport ability (in particular, hole transport ability), but also have excellent chemical structure stability due to deuterium (D) substitution. Therefore, they can be applied to the hole transport layer to simultaneously achieve the characteristics of organic electroluminescent devices, such as low voltage, high efficiency, and long lifespan characteristics of the devices.

[0037] Specifically, the compound represented by Chemical Formula 1 of the present invention contains at least one deuterium (D) in its molecular structure. From the perspective of potential energy, the mass of a deuterium (D) molecule is larger than that of hydrogen (H), and its zero-point energy is lower than that of hydrogen (H). Therefore, in terms of reaction, the dissociation of deuterium is relatively more difficult. However, due to the low zero-point energy, the bond dissociation energy of the compound substituted with deuterium increases, and the reactivity decreases, thus improving the stability of the molecule (Molecules 2014, 19 Chem. Commun., 2014, 50, 14870 - 14872 J. Org. Chem. 2004, 69, 7212 - 7219). Therefore, compared with the compound having the same structure without deuterium in the molecule, the chemical structure stability and thermal stability of the compound of Chemical Formula 1 are more excellent, thereby significantly improving the lifetime characteristics of the device. In particular, when the compound of Chemical Formula 1 is used as a hole transport layer material for an organic electroluminescent device, due to the substitution of deuterium (D) in the molecular structure, the device can be driven at a low voltage, thus improving the lifetime of the device.

[0038] In addition, in the compound of Chemical Formula 1 of the present invention, the spiro ring is formed by the condensation of the benzene part on one side of fluorene in the spiro[fluorene - xanthene] part or spiro[fluorene - thioxanthene] part with a monocyclic or polycyclic aromatic ring such as a benzene ring or a naphthalene ring. Therefore, the hole mobility is high and the hole transport ability is excellent. In addition, the HOMO energy level and LUMO energy level of the compound of Chemical Formula 1 are between the HOMO and LUMO energy levels of the hole injection layer and the light - emitting layer. Therefore, hole injection and transfer will proceed smoothly. Therefore, when an organic electroluminescent device contains the compound of the present invention as a hole transport layer material, not only can the luminous efficiency of the organic electroluminescent device be improved, but also the driving voltage can be reduced and the lifetime can be extended.

[0039] In addition, by introducing an amino group substituted with an aryl and / or heteroaryl group at the other benzene part of fluorene in the spiro ring in the compound of Chemical Formula 1, the luminous efficiency can be further improved due to the physicochemical properties of amorphous characteristics and high refractive index characteristics. In addition, due to the high glass transition temperature (Tg) of the compound of Chemical Formula 1, its stability is excellent, and its electrochemical stability is also excellent.

[0040] As described above, the compound represented by Chemical Formula 1 of the present invention has excellent chemical structure stability, thermal stability, electrochemical stability, and hole transport properties. Therefore, the compound represented by Chemical Formula 1 of the present invention can be used as a material for an organic layer of an organic electroluminescent element, preferably as a material for a hole transport layer or a hole transport auxiliary layer, and more preferably as a material for a hole transport layer. The performance and lifetime characteristics of an organic electroluminescent element containing such a compound of the present invention can be significantly improved, and the performance of a full-color organic light-emitting panel using such an organic electroluminescent element can also be maximized.

[0041] In the compound represented by Chemical Formula 1 of the present invention, (D)n refers to the number of deuterium (D) contained in the compound of Chemical Formula 1 above, and n≥1. That is, the compound of the present invention has a structure in which each spiro ring on both sides of the molecule is directly connected to an amine group substituted with an aryl group and / or a heteroaryl group or is connected through a linking group (for example, a phenylene group, etc.), and has a structure in which at least one deuterium (D) must be contained within the above molecular structure. As an example, 1≤n≤87, and more specifically, 1≤n≤47.

[0042] In addition, in the compound represented by Chemical Formula 1 above, X1 is O or S. For this reason, the above spiro ring is a part formed by condensing a benzene part on one side of fluorene in spiro[fluorene-xanthene] with an aromatic ring, or a part formed by condensing a benzene part on one side of fluorene in spiro[fluorene-thioxanthene] with an aromatic ring. The compound of Chemical Formula 1 of the present invention containing such a spiro ring has excellent amphoteric properties of electrons and holes compared with the case where X1 is N or C, and thus has excellent carrier transport ability. Therefore, when the compound of Chemical Formula 1 of the present invention is used as a material for a hole transport layer, the efficiency and the effect of improving the driving voltage can be improved by improving the hole transport ability.

[0043] In the compound represented by Chemical Formula 1 above, the ring CyA, as a ring condensed with a benzene part on one side of fluorene in the spiro ring, can be an aromatic ring of C6~C 30 Specifically, it can be a monocyclic aromatic ring of C6~C 30 or a polycyclic aromatic ring of C6~C 30 According to an example, the ring CyA can be a benzene ring, a naphthalene ring, an anthracene ring, a tetracene ring, a pyrene ring, a phenanthrene ring, a phenalene ring, a benzoanthracene ring, a benzopyrene ring, a triphenylene ring, (chrysene) ring, pentaphene ring, pentacene ring, and condensed rings between any two of the above rings, etc., but not limited thereto. Here, each ring in the polycyclic aromatic ring may be the same as or different from each other.

[0044] Depending on the type of the above-mentioned ring CyA, in the compound represented by the above chemical formula 1 the part may be any one of the following parts Mo1-1 to Mo1-3.

[0045] But not limited thereto.

[0046]

[0047] Among the above parts Mo1-1 to Mo1-3,

[0048] * refers to the part that forms a bond with the chemical formula 1,

[0049] X1, m1, R1, and R2 are each the same as defined in the above chemical formula 1,

[0050] m3 is an integer from 0 to 9.

[0051] The compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2 to 22 depending on the binding position of deuterium contained in the compound and the type of the ring CyA. But not limited thereto.

[0052] [Chemical formula 2]

[0053]

[0054] [Chemical formula 3]

[0055]

[0056] [Chemical formula 4]

[0057]

[0058] [Chemical formula 5]

[0059]

[0060] [Chemical formula 6]

[0061]

[0062] [Chemical formula 7]

[0063]

[0064] [Chemical formula 8]

[0065]

[0066] [Chemical Formula 9]

[0067]

[0068] [Chemical Formula 10]

[0069]

[0070] [Chemical Formula 11]

[0071]

[0072] [Chemical Formula 12]

[0073]

[0074] [Chemical Formula 13]

[0075]

[0076] [Chemical Formula 14]

[0077]

[0078] [Chemical Formula 15]

[0079]

[0080] [Chemical Formula 16]

[0081]

[0082] [Chemical Formula 17]

[0083]

[0084] [Chemical Formula 18]

[0085]

[0086] [Chemical Formula 19]

[0087]

[0088] [Chemical Formula 20]

[0089]

[0090] [Chemical Formula 21]

[0091]

[0092] [Chemical Formula 22]

[0093]

[0094] In the above Chemical Formulas 2 to 22,

[0095] X1, m1, R1, R2, n1 to n3, L1 to L3, Ar1, and Ar2 are each the same as defined in the above Chemical Formula 1,

[0096] m3 is an integer from 0 to 9,

[0097] (D) a represents the number of deuterium (D) atoms contained in the part, and a can be an integer from 0 to 58. Specifically, a can be from 0 to 26,

[0098] (D) b represents the number of deuterium atoms contained in the part, and b can be an integer from 0 to 12. Specifically, b can be from 0 to 4,

[0099] (D) c represents the number of deuterium atoms contained in the part, and c can be an integer from 0 to 17. Specifically, c can be from 0 to 17,

[0100] Among them, a + b + c ≥ 1 is possible. Specifically, 1 ≤ a + b + c ≤ 39 is possible.

[0101] In the compound represented by Chemical Formula 1 of the present invention, n1 to n3 can each be an integer from 0 to 3. Specifically, they can be 0 or 1.

[0102] Among them, when n1 to n3 are each 0, it means that L1 to L3 are each a single bond (direct bond). On the other hand, when n1 to n3 are each an integer from 1 to 3, L1 to L3 are divalent linking groups (linkers), which can be the same or different from each other and can each independently be selected from the group consisting of C6-C 18 arylene groups and heteroarylene groups having 5 to 18 ring atoms. Specifically, they can be selected from the group consisting of C6-C 18 arylene groups and heteroarylene groups having 5 to 18 ring atoms. Among them, one or more of L1, one or more of L2, and one or more of L3 can be the same or different from each other.

[0103] At this time, the arylene groups and heteroarylene groups of the above L1 to L3 can each independently be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 40 alkyl groups, C2-C 40alkenyl of, C2-C 40 alkynyl of, C3-C 40 cycloalkyl of, 3 to 40-membered heteroalkyl, C6-C 60 aryl of, 5 to 60-membered heteroaryl, C1-C 40 alkoxy of, C6-C 60 aryloxy of, C1-C 40 alkylsilyl of, C6-C 60 arylsilyl of, C1-C 40 alkylboron of, C6-C 60 arylboron of, C6-C 60 arylphosphino of, C6-C 60 arylphosphine oxide of, C6-C 60 arylamino of, C6-C 60 substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amino and 5 to 60-membered heteroarylamino, specifically, can be selected from deuterium (D), cyano (-CN), C1-C 20 alkyl of, C3-C 20 cycloalkyl of, 3 to 20-membered heteroalkyl, C6-C 30 aryl of, 5 to 30-membered heteroaryl and C6-C 30 arylamino of, substituted or unsubstituted with one or more substituents selected from the group consisting of, more specifically, can be substituted with at least one deuterium (D). At this time, when there are a plurality of the above substituents, they may be the same or different from each other.

[0104] According to one example, L1 to L3 are the same or different from each other, and each independently can be a single bond or selected from the group consisting of phenylene, biphenylene, terphenyl, naphthylene, phenanthrylene, triphenylene, carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, and combinations thereof. Among them, the hydrogen of phenylene, biphenylene, terphenyl, naphthylene, phenanthrylene, triphenylene, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and fluorenyl can be selected from deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 12 alkyl of, C6-C 10 aryl of, and 5 to 10-membered heteroaryl, substituted or unsubstituted with one or more substituents selected from the group consisting of, specifically, can be substituted with at least one deuterium (D).

[0105] According to another example, L1 to L3 are the same or different from each other, and each independently can be the following linking group L1-1. However, it is not limited thereto.

[0106]

[0107] In the above linking group L1-1,

[0108] * refers to the part that forms a bond with Chemical Formula 1,

[0109] (D) b As the number of deuteriums contained in the linking group L1-1, it can be 0 ≤ b ≤ 12, specifically, it can be 0 ≤ b ≤ 4,

[0110] n4 is an integer from 0 to 3,

[0111] m4 is an integer from 0 to 4,

[0112] Multiple R3s are the same as or different from each other,

[0113] R3 can be selected from the group consisting of hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl with 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl with 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphinyl oxide, C6-C 60 arylamino, C6-C 60 (aryl)(heteroaryl)amino and the group consisting of heteroarylamino with 5 to 60 ring atoms, or can condense with adjacent groups (e.g., R3-R3) to form a condensed ring, specifically, it can be selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 20 alkyl, heteroalkyl with 3 to 20 ring atoms, C6-C 30 aryl, heteroaryl with 5 to 30 ring atoms, and C6-C 30 arylamino.

[0114] In particular, when L1 is the above-mentioned linking group L1-1, part and part can be introduced into L1 as para-positions to each other. That is, when part is introduced (substituted) at the 1st carbon position of L1, based on the above part, part is introduced into its para-position (i.e., the 4th carbon position). In this case, not only can the hole transport ability of the compound of Chemical Formula 1 be maximized, but also the hole transfer between molecules can be made easier to reduce the driving voltage of the organic electroluminescent element. part and part as para-positions to each other and introduced into L1. That is, when part is introduced (substituted) at the 1st carbon position of L1, based on the above part, part is introduced into its para-position (i.e., the 4th carbon position). In this case, not only can the hole transport ability of the compound of Chemical Formula 1 be maximized, but also the hole transfer between molecules can be made easier to reduce the driving voltage of the organic electroluminescent element. part, in the case of introducing (substituting) part, based on the above part, part is introduced into its para-position (i.e., the 4th carbon position). In this case, not only can the hole transport ability of the compound of Chemical Formula 1 be maximized, but also the hole transfer between molecules can be made easier to reduce the driving voltage of the organic electroluminescent element.

[0115] In the compound represented by Chemical Formula 1 of the present invention, m1 can be an integer from 0 to 8, and m2 can be an integer from 0 to 23. Specifically, m2 can be from 0 to 9, and more specifically, it can be an integer from 1 to 5.

[0116] Among them, when m1 and m2 are each 0, it means that hydrogen is not substituted by substituents R1 and R2 respectively. On the other hand, when m1 is an integer from 1 to 8, it means that hydrogen is substituted by substituent R1, and when m2 is an integer from 1 to 23, it means that hydrogen is substituted by substituent R2. At this time, multiple R1s are the same or different from each other, and multiple R2s are the same or different from each other.

[0117] The above R1 and R2 are the same or different from each other and can each independently be selected from hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl with 3 to 40 nuclei, C6-C 60 aryl, heteroaryl with 5 to 60 nuclei, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphinoyl, C6-C 60 arylamino, C6-C 60Selected from the group consisting of (aryl)(heteroaryl)amino groups and heteroaryl amino groups having 5 to 60 ring atoms, or may condense with adjacent groups (e.g., R1-R1, R2-R2, etc.) to form a condensed ring. Specifically, R1 and R2 are the same or different from each other and each independently may be selected from the group consisting of hydrogen, deuterium (D), halogen groups, cyano groups, nitro groups, amino groups, C1-C 20 alkyl groups, C3-C 20 cycloalkyl groups, heterocycloalkyl groups having 3 to 20 ring atoms, C6-C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6-C 30 aryl amino groups. More specifically, R1 and R2 may be deuterium or aryl groups having 6 to C 30 substituted with deuterium and heteroaryl groups having 5 to 30 ring atoms.

[0118] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphine, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroaryl amino groups of R1 and R2 as described above may each independently be substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl groups, C2-C 40 alkenyl groups, C2-C 40 alkynyl groups, C3-C 40 cycloalkyl groups, heterocycloalkyl groups having 3 to 40 ring atoms, C6-C 60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, C1-C 40 alkoxy groups, C6-C 60 aryloxy groups, C1-C 40 alkylsilyl groups, C6-C 60 arylsilyl groups, C1-C 40 alkylboron groups, C6-C 60 arylboron groups, C6-C 60 arylphosphine groups, C6-C 60 arylphosphine oxide groups, C6-C 60 aryl amino groups, C6-C 60 (aryl)(heteroaryl)amino groups, and heteroaryl amino groups having 5 to 60 ring atoms, and specifically may each independently be substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), cyano (-CN), C1-C 20 alkyl groups, C3-C 20 cycloalkyl groups, heterocycloalkyl groups having 3 to 20 ring atoms, C6-C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6-C 30One or more substituents in the group consisting of arylamino groups are substituted or unsubstituted, and more specifically, may be substituted with at least one deuterium (D). At this time, when there are a plurality of the above substituents, they may be the same or different from each other.

[0119] According to one example, R1 and R2 are the same or different from each other, and each independently may be selected from the group consisting of deuterium (D), methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, and naphthyl. Specifically, R1 and R2 may be deuterium. At this time, the methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, and naphthyl of R1 and R2 may be substituted with at least one deuterium (D).

[0120] In the compound represented by Chemical Formula 1 of the present invention, Ar1 and Ar2 are the same or different from each other, and each independently is selected from the group consisting of hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl having 3 to 40 nuclear atoms, C6-C 60 aryl, heteroaryl having 5 to 60 nuclear atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphine oxide, C6-C 60 arylamino, C6-C 60 (aryl)(heteroaryl)amino and heteroarylamino groups having 5 to 60 nuclear atoms, or condensed with adjacent groups (e.g., Ar1-L2, Ar2-L3) to form a condensed ring.

[0121] The alkyl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroarylamino of Ar1 and Ar2 may each independently be selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heteroalkyl having 3 to 40 nuclei, C6-C60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 alkoxy group, C6-C 60 aryloxy group, C1-C 40 alkylsilyl group, C6-C 60 arylsilyl group, C1-C 40 alkylboron group, C6-C 60 arylboron group, C6-C 60 arylphosphino group, C6-C 60 arylphosphine oxide group, C6-C 60 arylamino group, C6-C 60 substituted or unsubstituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amino groups and heteroarylamino groups having 5 to 60 ring atoms. Specifically, each may independently be selected from deuterium (D), cyano (-CN), C1-C 20 alkyl group, C3-C 20 cycloalkyl group, heterocycloalkyl group having 3 to 20 ring atoms, C6-C 30 aryl group, heteroaryl group having 5 to 30 ring atoms, and C6-C 30 arylamino group. More specifically, it may be substituted with at least one deuterium (D). In this case, when there are multiple substituents, they may be the same or different from each other.

[0122] According to one example, Ar1 and Ar2 may be the same or different from each other and may each independently be selected from the group consisting of C6-C 60 aryl groups and heteroaryl groups having 5 to 60 ring atoms. In this case, the aryl groups and heteroaryl groups of Ar1 and Ar2 may be substituted with one or more deuteriums.

[0123] According to another example, Ar1 and Ar2 may be the same or different from each other and may each independently be selected from the group consisting of the following substituents S1-1 to S1-3. However, it is not limited thereto.

[0124]

[0125] (Among the above substituents S1-1 to S1-3,

[0126] * indicates the part that forms a bond with Chemical Formula 1,

[0127] (D) d1 As the number of deuteriums (D) included in substituent S1-1, it may be 0≤d1≤15. Specifically, it may be 0≤d1≤15,

[0128] (D) d2The number of deuteriums (D) contained as substituent S1-2 can be 0 ≤ d2 ≤ 7, specifically, it can be 0 ≤ d2 ≤ 7.

[0129] (D) d3 The number of deuteriums (D) contained as substituent S1-3 can be 0 ≤ d3 ≤ 8, specifically, it can be 0 ≤ d3 ≤ 8.

[0130] Each of o1 to o3 is 0 or 1, however, o1 + o2 + o3 ≥ 1.

[0131] m5 is an integer from 0 to 4.

[0132] m6 is an integer from 0 to 6.

[0133] m7 is an integer from 0 to 5.

[0134] m8 is an integer from 0 to 7.

[0135] m9 is an integer from 0 to 8.

[0136] Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4), and N(Ar5).

[0137] R3 and Ar3 to Ar5 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 arylphosphine oxide group, a C6-C 60 arylamino group, a C6-C 60 (aryl)(heteroaryl)amino group and a heteroarylamino group having 5 to 60 ring atoms, or condenses with an adjacent group (e.g., R3-R3, Ar3-Ar4, etc.) to form a condensed ring.

[0138] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroarylamino of Ar3 to Ar5 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl of, C2-C 40 alkenyl of, C2-C 40 alkynyl of, C2-C 40 cycloalkyl of, C3-C 60 aryl of, heterocycloalkyl having 3 to 40 ring atoms, C6-C 40 alkoxy of, C1-C 60 aryloxy of, C6-C 40 alkylsilyl of, C1-C 60 arylsilyl of, C6-C 40 alkylboron of, C1-C 60 arylboron of, C6-C 60 arylphosphino of, C6-C 60 arylphosphine oxide of, C6-C 60 arylamino of, C6-C 60 (aryl)(heteroaryl)amino of, and one or more substituents selected from the group consisting of heteroarylamino having 5 to 60 ring atoms are substituted or unsubstituted. At this time, when there are a plurality of the above substituents, they may be the same or different from each other.

[0139] The hydrogen of the above substituents S1-1 to S1-3 may be substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), halogen (for example, -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 12 alkyl of, C6-C 10 aryl of, and heteroaryl having 5 to 10 ring atoms. Specifically, it may be substituted with deuterium (D).

[0140] According to another example, Ar1 and Ar2 are the same or different from each other and may each independently be selected from the group consisting of the following substituents S2-1 to S2-12. However, it is not limited thereto.

[0141]

[0142] Among the above substituents S2-1 to S2-12,

[0143] * means the part that forms a bond with Chemical Formula 1,

[0144] (D) d1The number of deuterium (D) atoms contained in each of substituents S2-1 to S2-4 can be 0 ≤ d1 ≤ 15, specifically, it can be 1 ≤ d1 ≤ 15.

[0145] (D) d2 The number of deuterium (D) atoms contained in each of substituents S2-5 to S2-11 can be 0 ≤ d2 ≤ 7, specifically, it can be 1 ≤ d2 ≤ 4.

[0146] (D) d3 The number of deuterium (D) atoms contained in substituent S2-12 can be 0 ≤ d3 ≤ 8, specifically, it can be 1 ≤ d3 ≤ 4.

[0147] The hydrogen atoms of the above substituents S2-1 to S2-12 can be substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), C1-C 12 alkyl, C6-C 10 aryl, and heteroaryl having 5 to 10 nuclear atoms, specifically, it can be substituted by deuterium (D).

[0148] Depending on the types of the above ring CyA, L1, and Ar1, the compound represented by the above Chemical Formula 1 can be a compound represented by any one of the following Chemical Formulas 23 to 31. However, it is not limited thereto.

[0149] [Chemical Formula 23]

[0150]

[0151] [Chemical Formula 24]

[0152]

[0153] [Chemical Formula 25]

[0154]

[0155] [Chemical Formula 26]

[0156]

[0157] [Chemical Formula 27]

[0158]

[0159] [Chemical Formula 28]

[0160]

[0161] [Chemical Formula 29]

[0162]

[0163] [Chemical formula 30]

[0164]

[0165] [Chemical formula 31]

[0166]

[0167] In the above Chemical formulas 23 to 31,

[0168] X1, n1 to n3, L2, L3, m1, R1, R2, and Ar1 are each the same as defined in Chemical formula 1 above,

[0169] (D)n, as the number of deuteriums (D) contained in the compound, can be 1 ≤ n ≤ 87, and specifically, can be 1 ≤ n ≤ 53,

[0170] m3 is an integer from 0 to 9,

[0171] m4 is an integer from 0 to 4,

[0172] o1 to o3 are each 0 or 1, provided that o1 + o2 + o3 ≥ 1,

[0173] m5 is an integer from 0 to 4,

[0174] m6 is an integer from 0 to 6,

[0175] m7 is an integer from 0 to 5,

[0176] m8 is an integer from 0 to 7,

[0177] m9 is an integer from 0 to 8,

[0178] Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4), and N(Ar5),

[0179] R3 and Ar3 to Ar5 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 nuclear atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60aryl silyl groups having C1 to C 40 alkyl boronic groups having C6 to C 60 aryl boronic groups having C6 to C 60 aryl phosphino groups having C6 to C 60 aryl phosphine oxide groups having C6 to C 60 aryl amino groups having C6 to C 60 a group consisting of (aryl)(heteroaryl)amino groups and heteroaryl amino groups having 5 to 60 ring atoms, or condensed with an adjacent group to form a condensed ring,

[0180] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkyl silyl, aryl silyl, alkyl boronic, aryl boronic, aryl phosphino, aryl phosphine oxide, aryl amino, (aryl)(heteroaryl)amino and heteroaryl amino groups of Ar3 to Ar5 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1 to C 40 alkyl groups having C2 to C 40 alkenyl groups having C2 to C 40 alkynyl groups having C2 to C 40 cycloalkyl groups having C3 to C 60 heterocycloalkyl groups having 3 to 40 ring atoms, C6 to C 40 aryl groups having C5 to C 60 heteroaryl groups having 5 to 60 ring atoms, C1 to C 40 alkoxy groups having C6 to C 60 aryloxy groups having C6 to C 40 alkyl silyl groups having C1 to C 60 aryl silyl groups having C6 to C 60 alkyl boronic groups having C1 to C 60 aryl boronic groups having C6 to C 60 aryl phosphino groups having C6 to C 60 aryl phosphine oxide groups having C6 to C

[0181] The compound represented by Chemical Formula 1 of the present invention can be further specifically exemplified by the following Compounds 1 to 120, but is not limited thereto.

[0182]

[0183]

[0184]

[0185]

[0186] In the present invention, "alkyl" means a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc.

[0187] In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0188] In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, etc.

[0189] 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, adamantine, etc.

[0190] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons, preferably 1 to 3 carbons in the ring are replaced by heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholinyl, piperazinyl, etc.

[0191] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms which is composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed with each other. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0192] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed with each other, and further may include a form condensed with an aryl group. Examples of such heteroaryl include six-membered monocycles such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycycles such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0193] In the present invention, "alkoxy" is a monovalent substituent represented by R'O-, and the above R' means an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkoxy include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentyloxy, etc., but are not limited thereto.

[0194] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and the above R means an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy include phenoxy, naphthyloxy, diphenoxy, etc., but are not limited thereto.

[0195] In the present invention, "alkylsilyl" means a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and includes not only monosilylalkyl but also disilylalkyl and trisilylalkyl. In addition, "arylsilyl" means a silyl group substituted by an aryl group having 5 to 60 carbon atoms, and includes not only monosilylaryl but also polysilylaryls such as disilylaryl and trisilylaryl.

[0196] In the present invention, "alkylboron" means a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and "arylboron" means a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0197] In the present invention, "alkylphosphino" means a phosphino group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only monoalkylphosphino but also dialkylphosphino. In addition, in the present invention, "arylphosphino" means a phosphino group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, and includes not only monoarylphosphino but also diarylphosphino.

[0198] In the present invention, "arylamino" means an amino group substituted with an aryl group having 6 to 40 carbon atoms, and includes not only monoarylamino but also diarylamino.

[0199] <Organic electroluminescent element>

[0200] On the other hand, another aspect of the present invention relates to an organic electroluminescent element (hereinafter referred to as "organic EL element") containing the compound represented by the above chemical formula 1.

[0201] Specifically, the organic electroluminescent element of the present invention includes an anode, a cathode, and one or more organic layers interposed between the above anode and cathode, and at least one of the above one or more organic layers contains the compound represented by the above chemical formula 1. At this time, the above compounds can be used alone or in combination of two or more.

[0202] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one organic layer contains the compound represented by the above chemical formula 1. Preferably, the organic layer containing the compound of the above chemical formula 1 may be a hole transport layer.

[0203] According to an example, the above one or more organic 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 the hole transport layer may be the compound represented by the above chemical formula 1.

[0204] In the organic electroluminescent element, the compound represented by the above chemical formula 1 can be included as a hole transport layer material. In this case, the compound of the above chemical formula 1 has a high glass transition temperature, a high hole mobility and strong hole transport ability, and the HOMO and LUMO energy levels between the hole injection layer and the light emitting layer are appropriate, so that the injection and transfer of holes from the hole injection layer to the light emitting layer side are smooth, and it has an amorphous crystallinity and a high refractive index characteristic. Therefore, the efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, thermal stability, etc. of the organic electroluminescent element containing the compound of the above chemical formula 1 can be improved.

[0205] The structure of the organic electroluminescent element of the present invention is not particularly limited. For example, an anode 100, one or more organic layers 300, and a cathode 200 can be sequentially stacked on a substrate (see Figure 1 and Figure 2 ). Moreover, it can also be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0206] According to one example, as shown in Figure 1 , the above-mentioned organic electroluminescent element can 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 stacked on a substrate. Optionally, as shown in Figure 2 , an electron injection layer 350 can be located between the above-mentioned electron transport layer 340 and the cathode 200. In addition, a hole blocking layer (not shown) can be located between the above-mentioned light-emitting layer 330 and the electron transport layer 340. In the organic electroluminescent element of the present invention, at least one of the above-mentioned organic layers 300 [for example, the hole transport layer 320] contains the compound represented by the above Chemical Formula 1. In addition, the organic layer and the electrode can be formed and manufactured by materials and methods known in the art.

[0207] The above-mentioned organic layer can be formed by a vacuum evaporation method or a solution coating method. As examples of the above solution coating method, there are spin coating, dip coating, blade coating, inkjet printing, or thermal transfer printing methods, etc., but not limited thereto.

[0208] The substrate that can be used in the present invention is not particularly limited. As non-limiting examples, there are silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets, etc.

[0209] In addition, as examples of anode materials, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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-(ethylenedioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, etc., but not limited thereto.

[0210] In addition, as examples of cathode materials, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or their alloys; and multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0211] In addition, the hole injection layer, the light-emitting layer, the electron transport layer, and the electron injection layer are not particularly limited, and usually known substances in the art can be used.

[0212] Hereinafter, the present invention will be described in detail by way of examples, as follows. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0213] [Preparation Example 1] Synthesis of Compound J-1

[0214]

[0215] To deuterated phenol-d5 (phen-d5-ol, 9.91 g, 100 mmol) and 9-bromo-7H-benzo[c]fluoren-7-one (3.09 g, 10 mmol), methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added, and then the above mixture was heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction of the reaction solution. The mixture obtained after the completion of the reaction was extracted with CH2Cl2 to separate the organic layer, and then the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried with anhydrous MgSO4, and after distillation under reduced pressure, it was purified by silica gel column chromatography to obtain the target compound J-1 (2.34 g, yield 50%).

[0216] [Preparation Example 2] Synthesis of Compound J-2

[0217] <Step 1> Synthesis of 2-bromo-11H-benzo[b]fluorene-11-one-5,6,7,8,9,10-d6

[0218]

[0219] Under nitrogen, 6-bromo-2,3-dihydro-1H-inden-1-one (2.11 g, 10 mmol), compound J-2-1 (1.40 g, 10 mmol), and NaOEt (1.36 g, 20 mmol) were added to 25 mL of ethanol and refluxed for 6 hours. After the reaction solution was cooled to 0 °C and the precipitated solid was filtered, it was washed with methanol and then filtered under reduced pressure to obtain compound 2-bromo-11H-benzo[b]fluorene-11-one-5,6,7,8,9,10-d6 (1.54 g, yield 49%).

[0220] <Step 2> Synthesis of Compound J-2

[0221]

[0222] After adding methanesulfonic acid (MsOH) (3.84 g, 40 mmol) to deuterated phenol-2,4,6-d3 (9.71 g, 100 mmol) and 2-bromo-11H-benzo[b]fluorene-11-one-5,6,7,8,9,10-d6 (3.15 g, 10 mmol), the above mixture was heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction of the reaction solution. The mixture obtained after the completion of the reaction was extracted with CH2Cl2 to separate the organic layer, and then the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried with anhydrous MgSO4, and after distillation under reduced pressure, it was purified by silica gel column chromatography to obtain the target compound J-2 (2.26 g, yield 48%).

[0223] [Preparation Example 3] Synthesis of Compound J-3

[0224] <Step 1> Synthesis of 9-bromo-11H-benzo[a]fluorene-11-one-7,8,10-d3

[0225]

[0226] 1-Naphthoic acid (1.72 g, 10 mmol), diaryliodonium salt (11.92 g, 20 mmol), Pd(OAc)2 (0.02 g, 1 mmol), and t-BuONa (0.96 g, 10 mmol) were added to 50 ml of xylene, and the mixture was stirred at 110 °C for 24 hours. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and then the target compound 9-bromo-11H-benzo[a]fluorene-11-one-7,8,10-d3 (1.46 g, yield 47%) was obtained by column chromatography.

[0227] <Step 2> Synthesis of Compound J-3

[0228]

[0229] To a mixture of phenol (9.41 g, 100 mmol) and 9-bromo-11H-benzo[a]fluorene-11-one-7,8,10-d3 (3.12 g, 10 mmol), methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added. The above mixture was then heated under reflux at 120 °C for 12 h. Subsequently, the temperature of the reaction solution obtained by the above reflux heating was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction. The mixture obtained after the completion of the reaction was extracted with CH2Cl2 to separate the organic layer, which was then neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, and after distillation under reduced pressure, purification was carried out by silica gel column chromatography to obtain the target compound J-3 (2.13 g, yield 46%).

[0230] [Preparation Example 4] Synthesis of Compound J-4

[0231] <Step 1> Synthesis of methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3 (methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3)

[0232]

[0233] Methyl 2,6-dibromobenzoate-3,4,5-d3 (2.96 g, 10 mmol), naphthalen-1-ylboronic acid (1.71 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and the mixture was stirred at 100 °C for 8 h. After the completion of the reaction, extraction was carried out with dichloromethane and filtration was performed after adding MgSO4. After removing the solvent of the filtered organic layer, the target compound methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3 (1.54 g, yield 45%) was obtained by column chromatography.

[0234] <Step 2> Synthesis of 2-bromo-6-(naphthalen-1-yl)benzoic acid-3,4,5-d3

[0235]

[0236] Methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3 (3.44 g, 10 mmol) and sodium hydroxide (0.40 g, 10 mmol) were added to 50 mL of ethanol and refluxed for 6 h. The temperature was lowered to room temperature, acidified with 2 M hydrochloric acid, and the precipitate was filtered and recrystallized from ethanol to obtain the target compound 2-bromo-6-(naphthalen-1-yl)benzoic acid-3,4,5-d3 (1.45 g, 44%).

[0237] <Step 3> Synthesis of 8-bromo-7H-benzo[c]fluorene-7-one-9,10,11-d3

[0238]

[0239] Dissolve 2-bromo-6-(naphthalen-1-yl)benzoic acid-3,4,5-d3 (3.30 g, 10 mmol) in 100 mL of methanesulfonic acid, stir for 24 hours, and then pour it into ice water for precipitation. Filter the solid component after precipitation, wash it with distilled water, and then place it in an aqueous sodium bicarbonate solution and stir for 3 hours. After filtration, neutralize it with distilled water and recrystallize it with acetic acid to obtain the target compound 8-bromo-7H-benzo[c]fluorene-7-one-9,10,11-d3 (1.34 g, 43%).

[0240] <Step 4> Synthesis of Compound J-4

[0241]

[0242] Add methanesulfonic acid (MsOH) (3.84 g, 40 mmol) to deuterated phenol-2,6-d2 (9.61 g, 100 mmol) and 8-bromo-7H-benzo[c]fluorene-7-one-9,10,11-d3 (3.12 g, 10 mmol), and then heat the above mixture under reflux at 120 °C for 12 hours. Then, cool the temperature of the reaction solution obtained by the above reflux heating to room temperature, and add purified water to the above reaction solution to terminate the reaction of the reaction solution. Extract the mixture obtained after the reaction is completed with CH2Cl2 to separate the organic layer, then neutralize the separated organic layer with saturated calcium carbonate and wash it with distilled water. After that, dry the washed organic layer with anhydrous MgSO4, distill it under reduced pressure, and then purify it by silica gel column chromatography to obtain the target compound J-4 (1.95 g, yield 42%).

[0243] [Preparation Example 5] Synthesis of Compound J-5

[0244] <Step 1> Synthesis of methyl 4-chloro-2-(naphthalen-1-yl-d7)benzoate

[0245]

[0246] Methyl 2-bromo-4-chlorobenzoate (2.49 g, 10 mmol), (naphthalen-1-yl-d7)boronic acid (1.79 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and the mixture was stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound methyl 4-chloro-2-(naphthalen-1-yl-d7)benzoate (1.24 g, yield 41%) was obtained by column chromatography.

[0247] <Step 2> Synthesis of 4-chloro-2-(naphthalen-1-yl-d7)benzoic acid

[0248]

[0249] Methyl 4-chloro-2-(naphthalen-1-yl-d7)benzoate (3.03 g, 10 mmol) and sodium hydroxide (0.40 g, 10 mmol) were added to 50 mL of ethanol and refluxed for 6 hours. The temperature was lowered to room temperature, acidified with 2 M hydrochloric acid, the precipitate was filtered, and recrystallized from ethanol to obtain the compound 4-chloro-2-(naphthalen-1-yl-d7)benzoic acid (1.15 g, 40%).

[0250] <Step 3> Synthesis of 10-chloro-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6

[0251]

[0252] 4-Chloro-2-(naphthalen-1-yl-d7)benzoic acid (2.89 g, 10 mmol) was dissolved in 100 mL of methanesulfonic acid and stirred for 24 hours, then poured into ice water for precipitation. The solid component after precipitation was filtered, washed with distilled water, and stirred in an aqueous sodium bicarbonate solution for 3 hours. After filtration, it was neutralized with distilled water and recrystallized from acetic acid to obtain the compound 10-chloro-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (1.11 g, 41%).

[0253] <Step 4> Synthesis of Compound J-5

[0254]

[0255] To a mixture of deuterated phenol-4-d (9.51 g, 100 mmol) and 10-chloro-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (2.70 g, 10 mmol), methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added. The above mixture was then heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction. The mixture obtained after the reaction was extracted with CH2Cl2 to separate the organic layer, and the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-5 (1.78 g, yield 42%).

[0256] [Preparation Example 6] Synthesis of Compound J-6

[0257] <Step 1> Synthesis of methyl 3-bromo-2-(naphthalen-1-yl-d7)benzoate

[0258]

[0259] Methyl 3-bromo-2-iodobenzoate (3.40 g, 10 mmol), (naphthalen-1-yl-d7)boronic acid (1.79 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and the mixture was stirred at 100 °C for 8 hours. After the reaction was completed, it was extracted with dichloromethane and filtered through MgSO4. After removing the solvent of the filtered organic layer, the target compound methyl 3-bromo-2-(naphthalen-1-yl-d7)benzoate (1.49 g, yield 43%) was obtained by column chromatography.

[0260] <Step 2> Synthesis of 3-bromo-2-(naphthalen-1-yl-d7)benzoic acid

[0261]

[0262] Methyl 3-bromo-2-(naphthalen-1-yl-d7)benzoate (3.48 g, 10 mmol) and sodium hydroxide (0.40 g, 10 mmol) were added to 50 mL of ethanol and refluxed for 6 hours. The temperature was lowered to room temperature, acidified with 2M hydrochloric acid, the precipitate was filtered, and recrystallized from ethanol to obtain the compound 3-bromo-2-(naphthalen-1-yl-d7)benzoic acid (1.47 g, 44%).

[0263] <Step 3> Synthesis of 11-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6

[0264]

[0265] After dissolving 3-bromo-2-(naphthalen-1-yl-d7)benzoic acid (3.34 g, 10 mmol) in 100 mL of methanesulfonic acid, the mixture was stirred for 24 hours and then poured into ice water for precipitation. The solid component after precipitation was filtered, washed with distilled water, and then placed in an aqueous sodium bicarbonate solution and stirred for 3 hours. After filtration, it was neutralized with distilled water and recrystallized with acetic acid to obtain compound 11-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (1.41 g, 45%).

[0266] <Step 4> Synthesis of Compound J-6

[0267]

[0268] In a baked-out flask, 1-(2-bromophenoxy)benzene-2,3,4,5,6-d5 (2.54 g, 10 mmol) was dissolved in 40 mL of anhydrous THF, and the reaction mixture was cooled to -78 °C. A solution of n-BuLi (10 mmol) was slowly added dropwise and then stirred for 1 hour. Subsequently, 1-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (3.15 g, 10 mmol) was dissolved in 20 mL of THF and added dropwise at -78 °C. The reaction mixture was slowly warmed to room temperature, the reaction was terminated with NH4Cl, and then concentrated under reduced pressure. The concentrated solution was carefully mixed with 30 mL of acetic acid, and then 5 mL of fuming HCl was added. After stirring at 75 °C for 6 hours, the mixture was cooled to room temperature, and the precipitated solid was filtered under reduced pressure and then washed with methanol to obtain compound J-6 (2.16 g, yield 46%).

[0269] [Preparation Example 7] Synthesis of Compound J-7

[0270] <Step 1> Synthesis of methyl 5-bromo-2-(naphthalen-1-yl-d7)benzoate

[0271]

[0272] Methyl 5-bromo-2-iodobenzoate (3.40 g, 10 mmol), (naphthalen-1-yl-d7)boronic acid (1.79 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and the mixture was stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound methyl 5-bromo-2-(naphthalen-1-yl-d7)benzoate (1.63 g, yield 47%) was obtained by column chromatography.

[0273] <Step 2> Synthesis of 5-bromo-2-(naphthalen-1-yl-d7)benzoic acid

[0274]

[0275] Methyl 5-bromo-2-(naphthalen-1-yl-d7)benzoate (3.48 g, 10 mmol) and sodium hydroxide (0.40 g, 10 mmol) were added to 50 mL of ethanol and refluxed for 6 hours. The temperature was lowered to room temperature, acidified with 2M hydrochloric acid, the precipitate was filtered, and recrystallized from ethanol to obtain the target compound 5-bromo-2-(naphthalen-1-yl-d7)benzoic acid (1.60 g, 48%).

[0276] <Step 3> Synthesis of 9-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6

[0277]

[0278] 5-Bromo-2-(naphthalen-1-yl-d7)benzoic acid (3.34 g, 10 mmol) was dissolved in 100 mL of methanesulfonic acid and stirred for 24 hours, then poured into ice water for precipitation. The solid component after precipitation was filtered, washed with distilled water, and stirred in an aqueous sodium bicarbonate solution for 3 hours. After filtration, it was neutralized with distilled water and recrystallized from acetic acid to obtain the compound 9-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (1.54 g, 49%).

[0279] <Step 4> Synthesis of Compound J-7

[0280]

[0281] After adding methanesulfonic acid (MsOH) (3.84 g, 40 mmol) to benzene-3,5-d2-thiol (11.21 g, 100 mmol) and 9-bromo-7H-benzo[c]fluorene-7-one-1,2,3,4,5,6-d6 (3.15 g, 10 mmol), the above mixture was heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction of the reaction solution. The mixture obtained after the completion of the reaction was extracted with CH2Cl2 to separate the organic layer, and then the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, and after distillation under reduced pressure, it was purified by silica gel column chromatography to obtain the target compound J-7 (2.43 g, yield 50%).

[0282] [Preparation Example 8] Synthesis of Compound J-8

[0283] <Step 1> Synthesis of 3-bromo-11H-benzo[b]fluorene-11-one-5,10-d2

[0284]

[0285] Under nitrogen, 5-bromo-2,3-dihydro-1H-inden-1-one (2.11 g, 10 mmol), J-8-1 (1.36 g, 10 mmol), and NaOEt (1.36 g, 20 mmol) were added to 25 mL of ethanol and refluxed for 6 hours. After the reaction solution was cooled to 0 °C and the precipitated solid was filtered, it was washed with methanol and then filtered under reduced pressure to obtain 3-bromo-11H-benzo[b]fluorene-11-one-5,10-d2 (1.52 g, yield 49%).

[0286] <Step 2> Synthesis of Compound J-8

[0287]

[0288] To 11.01 g (100 mmol) of benzenethiol and 3.11 g (10 mmol) of 3-bromo-11H-benzo[b]fluorene-11-one-5,10-d2, 3.84 g (40 mmol) of methanesulfonic acid (MsOH) was added, and the above mixture was heated under reflux at 120 °C for 12 h. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction. The mixture obtained after completion of the reaction was extracted with CH2Cl2 to separate the organic layer, and the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, and after distillation under reduced pressure, purification was carried out by silica gel column chromatography to obtain the target compound J-8 (2.30 g, yield 48%).

[0289] [Preparation Example 9] Synthesis of Compound J-9

[0290] <Step 1> Synthesis of 7-bromo-11H-benzo[a]fluorene-11-one-1-d

[0291]

[0292] 1.73 g (10 mmol) of 1-naphthoic acid-8-d, 11.75 g (20 mmol) of diaryliodonium salt, 0.02 g (1 mmol) of Pd(OAc)2, and 0.96 g (10 mmol) of t-BuONa were added to 50 ml of xylene, and the mixture was stirred at 110 °C for 24 h. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the target compound 7-bromo-11H-benzo[a]fluorene-11-one-1-d (1.45 g, yield 47%) was obtained by column chromatography.

[0293] <Step 2> Synthesis of Compound J-9

[0294]

[0295] After adding methanesulfonic acid (MsOH) (3.84 g, 40 mmol) to benzene-d5-thiol (11.52 g, 100 mmol) and 7-bromo-11H-benzo[a]fluorene-11-one-1-d (3.10 g, 10 mmol), the above mixture was heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction of the reaction solution. The mixture obtained after the completion of the reaction was extracted with CH2Cl2 to separate the organic layer, and then the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, and after distillation under reduced pressure, it was purified by silica gel column chromatography to obtain the target compound J-9 (2.23 g, yield 46%).

[0296] [Preparation Example 10] Synthesis of Compound J-10

[0297] <Step 1> Synthesis of methyl 2-bromo-6-(naphthalen-2-yl)benzoate-3,4,5-d3

[0298]

[0299] Methyl 2,6-dibromobenzoate-3,4,5-d3 (2.96 g, 10 mmol), 2-naphthylboronic acid (1.71 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and the mixture was stirred at 100 °C for 8 hours. After the completion of the reaction, it was extracted with dichloromethane and filtered through MgSO4. After removing the solvent of the filtered organic layer, the target compound methyl 2-bromo-6-(naphthalen-2-yl)benzoate-3,4,5-d3 (1.54 g, yield 45%) was obtained by column chromatography.

[0300] <Step 2> Synthesis of 2-bromo-6-(naphthalen-2-yl)benzoic acid-3,4,5-d3

[0301]

[0302] Methyl 2-bromo-6-(naphthalen-2-yl)benzoate-3,4,5-d3 (3.44 g, 10 mmol) and sodium hydroxide (0.40 g, 10 mmol) were added to 50 mL of ethanol and refluxed for 6 hours. The temperature was lowered to room temperature, acidified with 2 M hydrochloric acid, the precipitate was filtered, and recrystallized with ethanol to obtain the compound 2-bromo-6-(naphthalen-2-yl)benzoic acid-3,4,5-d3 (1.45 g, 44%).

[0303] <Step 3> Synthesis of 1-bromo-11H-benzo[b]fluorene-11-one-2,3,4-d3

[0304]

[0305] 2-Bromo-6-(naphthalen-2-yl)benzoic acid-3,4,5-d3 (3.30 g, 10 mmol) was dissolved in 100 mL of methanesulfonic acid and stirred for 24 hours, and then poured into ice water for precipitation. The solid component after precipitation was filtered, washed with distilled water, and then placed in an aqueous sodium bicarbonate solution and stirred for 3 hours. After filtration, it was neutralized with distilled water and recrystallized with acetic acid to obtain compound 1-bromo-11H-benzo[b]fluorene-11-one-2,3,4-d3 (1.34 g, 43%).

[0306] <Step 4> Synthesis of Compound J-10

[0307]

[0308] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to benzenethiol-4-d (11.11 g, 100 mmol) and 1-bromo-11H-benzo[b]fluorene-11-one-2,3,4-d3 (3.12 g, 10 mmol), and the above mixture was heated under reflux at 120 °C for 12 hours. Then, the temperature of the reaction solution obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction solution to terminate the reaction of the reaction solution. The mixture obtained after the reaction was extracted with CH2Cl2 to separate the organic layer, and the separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. Then, the washed organic layer was dried with anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-10 (2.02 g, yield 42%).

[0309] [Preparation Example 11] Synthesis of Compound J-11

[0310]

[0311] To a solution of benzene-2,4,6-d3-thiol (11.31 g, 100 mmol) and 10-bromo-7H-benzo[c]fluoren-7-one (3.09 g, 10 mmol) was added methanesulfonic acid (MsOH) (3.84 g, 40 mmol), and the resulting mixture was heated under reflux at 120 °C for 12 h. Then, the temperature of the reaction mixture obtained by the above heating under reflux was cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. The mixture obtained after completion of the reaction was extracted with CH2Cl2 to separate the organic layer, which was then neutralized with saturated calcium carbonate and washed with distilled water. Thereafter, the washed organic layer was dried over anhydrous MgSO4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-11 (1.97 g, yield 41%).

[0312] [Preparation Example 12] Synthesis of Compound J-12

[0313]

[0314] In a baked flask, (2-bromophenyl)(phenyl-2,4,6-d3) sulfane (2.68 g, 10 mmol) was dissolved in 40 mL of anhydrous THF, and the reaction mixture was cooled to -78 °C. A solution of n-BuLi (10 mmol) was slowly added dropwise, and the mixture was stirred for 1 h. Then, 9-bromo-7H-benzo[c]fluoren-7-one (3.09 g, 10 mmol) was dissolved in 20 mL of THF and added dropwise at -78 °C. The reaction mixture was slowly warmed to room temperature, the reaction was terminated with NH4Cl, and the mixture was concentrated under reduced pressure. The concentrated solution was carefully mixed with 30 mL of acetic acid, 5 mL of fuming HCl was added, and the mixture was stirred at 75 °C for 6 h. Thereafter, the mixture was cooled to room temperature, the precipitated solid was filtered under reduced pressure, and washed with methanol to obtain the target compound J-12 (1.91 g, yield 40%).

[0315] [Preparation Example 13] Synthesis of Compound J-13

[0316]

[0317] 9-Bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.61 g, 10 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (3.61 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) were dissolved in 100 ml of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound J-13 (3.19 g, yield 43%) was obtained by column chromatography.

[0318] [Preparation Example 14] Synthesis of Compound J-14

[0319]

[0320] 9-Bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.61 g, 10 mmol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophen-2-amine (3.51 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) were dissolved in 100 ml of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound J-14 (3.22 g, yield 44%) was obtained by column chromatography.

[0321] [Preparation Example 15] Synthesis of Compound J-15

[0322]

[0323] 9-Bromospiro[benzo[c]fluorene-7,9'-thioxanthene] (4.77 g, 10 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]furan-4-amine (5.37 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound J-15 (3.63 g, yield 45%) was obtained by column chromatography.

[0324] [Synthesis Example 1] Synthesis of Compound 1

[0325]

[0326] Dissolve the compound J-1 (4.69 g, 10 mmol) synthesized in Preparation Example 1, bis([1,1'-biphenyl]-4-yl)amine (3.21 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After completion of the reaction, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 1 (2.91 g, yield 41%) by column chromatography.

[0327] Mass: [(M+H) + : 709

[0328] [Synthesis Example 2] Synthesis of Compound 2

[0329]

[0330] Dissolve the compound J-2 (4.71 g, 10 mmol) synthesized in Preparation Example 2, N-(phenyl-d5)-[1,1'-biphenyl]-4-amine (2.50 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After completion of the reaction, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 2 (2.69 g, yield 42%) by column chromatography.

[0331] Mass: [(M+H) + : 640

[0332] [Synthesis Example 3] Synthesis of Compound 3

[0333]

[0334] Dissolve the compound J-3 (4.64 g, 10 mmol) synthesized in Preparation Example 3, N-([1,1'-biphenyl]-2-yl-4'-d)-9,9-dimethyl-9H-fluorene-2-amine (3.62 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain compound 3 (3.20 g, yield 43%) by column chromatography.

[0335] Mass: [(M+H) + : 745

[0336] [Synthesis Example 4] Synthesis of Compound 4

[0337]

[0338] Dissolve the compound J-4 (4.64 g, 10 mmol) synthesized in Preparation Example 4, N-(dibenzo[b,d]thiophen-1-yl)dibenzo[b,d]furan-3-amine (3.65 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 4 (3.30 g, yield 44%) by column chromatography.

[0339] Mass: [(M+H) + : 750

[0340] [Synthesis Example 5] Synthesis of Compound 5

[0341]

[0342] Dissolve the compound J-5 (4.24 g, 10 mmol) synthesized in Preparation Example 5, N-phenyl-[1,1'-biphenyl]-2'-d-4-amine (2.46 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene, and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent of the filtered organic layer, obtain the target compound 5 (2.85 g, yield 45%) by column chromatography.

[0343] Mass: [(M+H) + : 634

[0344] [Synthesis Example 6] Synthesis of Compound 6

[0345]

[0346] Dissolve the compound J-6 (4.71 g, 10 mmol) synthesized in Preparation Example 6, N-(4-(naphthalen-1-yl-5,8-d2)phenyl)-[1,1'-biphenyl]-3-amine (3.73 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene, and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent of the filtered organic layer, obtain the target compound 6 (3.51 g, yield 46%) by column chromatography.

[0347] Mass: [(M+H) + : 764

[0348] [Synthesis Example 7] Synthesis of Compound 7

[0349]

[0350] Dissolve the compound J-7 (4.87 g, 10 mmol) synthesized in Preparation Example 7, N-(4-(9H-carbazol-9-yl-d8)phenyl)-4-(dibenzo[b,d]furan-1-yl)aniline (5.08 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 7 (4.30 g, yield 47%) by column chromatography.

[0351] Mass: [(M+H) + : 915

[0352] [Synthesis Example 8] Synthesis of Compound 8

[0353]

[0354] Dissolve the compound J-8 (4.79 g, 10 mmol) synthesized in Preparation Example 8, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)naphthalene-d7-2-amine (3.07 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 8 (3.38 g, yield 48%) by column chromatography.

[0355] Mass: [(M+H) + : 705

[0356] [Synthesis Example 9] Synthesis of Compound 9

[0357]

[0358] Dissolve the compound J-9 (4.86 g, 10 mmol) synthesized in Preparation Example 9, N-phenylbenzene-2,4,6-d3-amine (1.72 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene, and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 9 (2.83 g, yield 49%) by column chromatography.

[0359] Mass: [(M+H) + : 577

[0360] [Synthesis Example 10] Synthesis of Compound 10

[0361]

[0362] Dissolve the compound J-10 (4.86 g, 10 mmol) synthesized in Preparation Example 10, N-(9,9-dimethyl-9H-fluoren-4-yl-1,2,3,5,6,7,8-d7)-9,9-dimethyl-9H-fluorene-1,2,4,5,6,7,8-d7-3-amine (4.15 g, 10 mmol), Pd2(dba)3 (0.91 g, 1 mmol), X-Phos (0.95 g, 2 mmol), and NaOt-Bu (1.92 g, 20 mmol) in 100 ml of toluene, and stir at 120 °C for 6 hours. After the reaction is completed, extract with dichloromethane and filter through MgSO4. After removing the solvent from the filtered organic layer, obtain the target compound 10 (4.08 g, yield 50%) by column chromatography.

[0363] Mass: [(M+H) + : 817

[0364] [Synthesis Example 11] Synthesis of Compound 11

[0365]

[0366] The synthesized compound J-11 (4.81 g, 10 mmol) in Preparation Example 11, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-2,3,5,6-d4)-9H-fluoren-2-amine (5.67 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was completed, extraction was carried out with dichloromethane and filtered through MgSO4. After removing the solvent of the filtered organic layer, the target compound 11 (4.12 g, yield 49%) was obtained by column chromatography.

[0367] Mass: [(M+H) + : 842

[0368] [Synthesis Example 12] Synthesis of Compound 12

[0369]

[0370] The synthesized compound J-12 (4.79 g, 10 mmol) in Preparation Example 12, N-(dibenzo[b,d]furan-4-yl-6,7,8,9-d4)-9-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazol-3-amine-2,6,7-d3 (6.33 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of ethanol / 25 ml of H2O, and stirred at 100 °C for 8 hours. After the reaction was completed, extraction was carried out with dichloromethane and filtered through MgSO4. After removing the solvent of the filtered organic layer, the target compound 12 (4.34 g, yield 48%) was obtained by column chromatography.

[0371] Mass: [(M+H) + : 906

[0372] [Synthesis Example 13] Synthesis of Compound 13

[0373]

[0374] The compound J-13 (7.41 g, 10 mmol) synthesized in Preparation Example 13 was dissolved in perdeuterated benzene (C6D6) (84.15 g, 1 mol). After adding CF3SO3D (7.55 g, 50 mmol), the mixture was stirred at 80 °C. Samples were taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, it was cooled to room temperature. It was confirmed by LC-MS measurement that deuterium substitution could be carried out at different ratios according to the conditions. Na2CO3 in D2O was added to terminate the reaction, and the organic solvent was concentrated. Recrystallization was carried out using toluene and acetone solvents to obtain the deuterated target compound 13 (3.64 g, yield 47%).

[0375] Mass: [(M+H) + : 775

[0376] [Synthesis Example 14] Synthesis of Compound 14

[0377]

[0378] The compound J-14 (7.31 g, 10 mmol) synthesized in Preparation Example 14 was dissolved in perdeuterated benzene (C6D6) (84.15 g, 1 mol). After adding CF3SO3D (7.55 g, 50 mmol), the mixture was stirred at 80 °C. Samples were taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, it was cooled to room temperature. It was confirmed by LC-MS measurement that deuterium substitution could be carried out at different ratios according to the conditions. Na2CO3 in D2O was added to terminate the reaction, and the organic solvent was concentrated. Recrystallization was carried out using toluene and acetone solvents to obtain the deuterated target compound 14 (3.51 g, yield 46%).

[0379] Mass: [(M+H) + : 765

[0380] [Synthesis Example 15] Synthesis of Compound 15

[0381]

[0382] The compound J-15 (8.08 g, 10 mmol) synthesized in Preparation Example 15 was dissolved in perdeuterated benzene (C6D6) (84.15 g, 1 mol). After adding CF3SO3D (7.55 g, 50 mmol), the mixture was stirred at 80 °C. Samples were taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, it was cooled to room temperature. It was confirmed by LC-MS measurement that deuterium substitution could be carried out at different ratios according to the conditions. Na2CO3 in D2O was added to terminate the reaction, and the organic solvent was concentrated. Recrystallization was carried out using toluene and acetone solvents, and thus the deuterated target compound 15 (3.80 g, yield 45%) was obtained.

[0383] Mass: [(M + H) + : 845

[0384] [Example 15] Fabrication of a blue organic electroluminescent device

[0385] The compound 1 synthesized in Synthesis Example 1 above was subjected to high-purity sublimation purification by a generally known method, and a blue organic electroluminescent device was fabricated according to the following process.

[0386] First, a glass substrate coated with indium tin oxide (ITO) with a thickness film was washed ultrasonically with distilled water. After the distilled water washing was completed, it was ultrasonically washed and dried with solvents such as isopropyl alcohol, acetone, and methanol, and then transferred to an ultraviolet ozone (UV OZONE) cleaner (Power sonic 405, Hwashintech). After that, the above substrate was cleaned with UV for 5 minutes, and then the substrate was transferred to a vacuum evaporation apparatus.

[0387] An organic electroluminescent device was fabricated by laminating in the order of HI + 2% HAT-CN6 (10 nm) / Compound 1 (140 nm) / EB (5 nm) / BH + 2% BD (20 nm) / HB (5 nm) / ET + Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) on the ITO transparent electrode prepared as above. At this time, the structures of HI, HAT-CN6, EB, BH, BD, HB, ET, and Liq used are as follows.

[0388]

[0389] [Examples 2 to 15] Fabrication of a blue organic electroluminescent device

[0390] The compound 1 used as the hole transport layer material in Example 1 was replaced with the hole transport layer materials in Table 1, respectively, and a blue organic electroluminescent device was fabricated in the same manner as in Example 1 except for this.

[0391] [Comparative Examples 1 to 3] Fabrication of Blue Organic Electroluminescent Devices

[0392] Compound HI, HT1, and HT2 were respectively used to replace Compound 1 used as the hole transport layer material in Example 1, and blue organic electroluminescent devices were fabricated in the same manner as in Example 1 described above. At this time, the structures of HI, HT1, and HT2 used are as follows.

[0393]

[0394] [Evaluation Example 1]

[0395] For the organic electroluminescent devices fabricated in Examples 1 to 15 and Comparative Examples 1 to 3, the driving voltage, emission wavelength, and current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

[0396] [Table 1]

[0397]

[0398]

[0399] It can be confirmed from Table 1 that, compared with the organic electroluminescent devices of Comparative Examples 1 to 3 using conventional hole transport layer materials (e.g., HI) or compounds without deuterium (D) (e.g., HT1, HT2) in the hole transport layer, the organic electroluminescent devices of Examples 1 to 15 using the compounds of the present invention in the hole transport layer are more excellent in terms of driving voltage, emission peak, and current efficiency.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the Chemical Formula 1, n≥1， The cyclic CyA is an aromatic ring of C6 to C 30 and X1 is O or S, n1 to n3 are each an integer from 0 to 3, L1 to L3 are the same as or different from each other, and each independently is a single bond or is selected from the group consisting of arylene having 6 to C 30 and heteroarylene having 5 to 30 ring nuclei, m1 is an integer from 0 to 8, m2 is an integer from 0 to 23, R1, R2, Ar1 and Ar2 are the same as or different from one another, and are each independently selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 arylphosphine oxide group, a C6-C 60 arylamino group, a C6-C 60 (aryl)(heteroaryl)amino group and a heteroarylamino group having 5 to 60 ring atoms, or condensed with an adjacent group to form a condensed ring, The arylene and heteroarylene of L1 to L3 and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroarylamino of R1, R2, Ar1, and Ar2 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl, C3-C 40 cycloalkyl, heterocycloalkyl having 3 to 40 ring atoms, C6-C 60 aryl, heteroaryl having 5 to 60 ring atoms, C1-C 40 alkoxy, C6-C 60 aryloxy, C1-C 40 alkylsilyl, C6-C 60 arylsilyl, C1-C 40 alkylboron, C6-C 60 arylboron, C6-C 60 arylphosphino, C6-C 60 arylphosphine oxide, C6-C 60 arylamino, C6-C 60 one or more substituents selected from the group consisting of (aryl)(heteroaryl)amino and heteroarylamino having 5 to 60 ring atoms, and when there are a plurality of the substituents, they may be the same or different from each other.

2. The compound according to claim 1, in the compound represented by Chemical Formula 1, is any one of the following parts Mo1-1 to Mo1-3: In the partial Mo1-1 to Mo1-3, X1, m1, R1, and R2 are each the same as defined in Claim 1, m3 is an integer from 0 to 9.

3. The compound according to Claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 22: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] In the Chemical Formulas 2 to 22, X1, m1, R1, R2, n1 to n3, L1 to L3, Ar1, and Ar2 are each the same as defined in Claim 1, m3 is an integer from 0 to 9, a is an integer from 0 to 58, b is an integer from 0 to 12, c is an integer from 0 to 17, However, a + b + c ≥ 1.

4. The compound according to Claim 1, wherein L1 to L3 are the same as or different from each other and are each independently the following linking group L1-1: In the linking group L1-1, (D) b is the number of deuteriums contained in the linking group L1-1, and 0 ≤ b ≤ 12 n4 is an integer from 0 to 3, m4 is an integer from 0 to 4, R3 is selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 arylphosphine oxide group, a C6-C 60 arylamino group, a C6-C 60 (aryl)(heteroaryl)amino group and a heteroarylamino group having 5 to 60 ring atoms, or condensed with an adjacent group to form a condensed ring.

5. The compound according to Claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently selected from the group consisting of the following substituents S1-1 to S1-3: In the substituents S1-1 to S1-3, (D) d1 is the number of deuterium (D) atoms contained in the substituent S1-1, and 0 ≤ d1 ≤ 15 (D) d2 is the number of deuteriums (D) included in the substituent S1-2 and 0 ≤ d2 ≤ 7, (D) d3 is the number of deuterium (D) atoms contained in the substituent S1-3, and 0 ≤ d3 ≤ 8 o1 to o3 are each 0 or 1, however, o1 + o2 + o3 ≥ 1, m5 is an integer from 0 to 4, m6 is an integer from 0 to 6, m7 is an integer from 0 to 5, m8 is an integer from 0 to 7, m9 is an integer from 0 to 8, Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4), and N(Ar5), R3 and Ar3 to Ar5 are the same as or different from each other, and each independently is selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 arylphosphine oxide group, a C6-C 60 arylamino group, a C6-C 60 (aryl)(heteroaryl)amino group and a heteroarylamino group having 5 to 60 ring atoms, or condensed with an adjacent group to form a condensed ring, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroarylamino of Ar3 to Ar5 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl of, C2-C 40 alkenyl of, C2-C 40 alkynyl of, C2-C 40 cycloalkyl of, C3-C 60 aryl of, heterocycloalkyl having 3 to 40 ring atoms, C6-C 40 alkoxy of, C1-C 60 aryloxy of, C6-C 40 alkylsilyl of, C1-C 60 arylsilyl of, C6-C 40 alkylboron of, C1-C 60 arylboron of, C6-C 60 arylphosphino of, C6-C 60 arylphosphine oxide of, C6-C 60 arylamino of, C6-C 60 one or more substituents selected from the group consisting of (aryl)(heteroaryl)amino and heteroarylamino having 5 to 60 ring atoms, and when there are a plurality of the substituents, they may be the same as or different from each other.

6. The compound according to Claim 1, wherein the compound represented by the Chemical Formula 1 is represented by any one of the following Chemical Formulas 23 to 31: [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] In the Chemical Formulas 23 to 31, X1, n1 to n3, L2, L3, m1, R1, R2, and Ar1 are each the same as defined in Claim 1, (D)n is the number of deuteriums (D) contained in the compound and 1 ≤ n ≤ 87, m3 is an integer from 0 to 9, m4 is an integer from 0 to 4, o1 to o3 are each 0 or 1, however, o1 + o2 + o3 ≥ 1, m5 is an integer from 0 to 4, m6 is an integer from 0 to 6, m7 is an integer from 0 to 5, m8 is an integer from 0 to 7, m9 is an integer from 0 to 8, Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4), and N(Ar5), R3 and Ar3 to Ar5 are the same as or different from one another, and each independently is selected from the group consisting of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40 alkynyl group, a C3-C 40 cycloalkyl group, a heteroalkyl group having 3 to 40 ring atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, a C1-C 40 alkoxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a C6-C 60 arylphosphino group, a C6-C 60 arylphosphine oxide group, a C6-C 60 arylamino group, a C6-C 60 (aryl)(heteroaryl)amino group and a heteroarylamino group having 5 to 60 ring atoms, or condenses with an adjacent group to form a condensed ring, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, arylphosphino, arylphosphine oxide, arylamino, (aryl)(heteroaryl)amino, and heteroarylamino of Ar3 to Ar5 are each independently selected from the group consisting of deuterium (D), halogen, cyano, nitro, amino, C1-C 40 alkyl of, C2-C 40 alkenyl of, C2-C 40 alkynyl of, C2-C 40 cycloalkyl of, C3-C 60 aryl of, heterocycloalkyl having 3 to 40 ring atoms, C6-C 40 alkoxy of, C1-C 60 aryloxy of, C6-C 40 alkylsilyl of, C1-C 60 arylsilyl of, C6-C 40 alkylboron of, C1-C 60 arylboron of, C6-C 60 arylphosphino of, C6-C 60 arylphosphine oxide of, C6-C 60 arylamino of, C6-C 60 (aryl)(heteroaryl)amino of, and one or more substituents selected from the group consisting of heteroarylamino having 5 to 60 ring atoms are substituted or unsubstituted. In this case, when there are a plurality of the substituents, they may be the same or different from each other.

7. The compound represented by Chemical Formula 1 according to claim 1 is any one of Compounds 1 to 120 below:

8. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, At least one of the one or more organic layers contains the organic compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer containing the organic compound is a hole transport layer.

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