Organic compound and organic electroluminescent device using the same

Abstract

The present invention relates to a novel organic light-emitting compound and an organic EL device using the same, and more particularly to a compound having excellent thermal stability, electrochemical stability, light-emitting ability, and hole / electron transport ability, and an organic EL device having improved properties such as luminous efficiency, driving voltage, and lifespan by incorporating 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 structural stability, thermal stability, electrochemical stability, and hole transport ability, and an organic electroluminescent device having improved properties such as luminous efficiency, driving voltage, and lifespan by incorporating the compound in one or more organic material layers. [Background technology]

[0002] In an organic electroluminescent device (hereinafter referred to as "organic EL device"), when a current or voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode and electrons are injected into the organic layer from the negative electrode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons return to the ground state. Organic materials used in the organic layer are classified according to their function into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] The light-emitting layer materials of organic EL devices can be classified into blue, green, and red light-emitting materials based on the emitted light color. Furthermore, yellow and orange light-emitting materials are also used to achieve more natural colors. Host / dopant systems are also used as light-emitting materials to improve color purity and luminous efficiency through energy transfer. The dopant materials are broadly divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. These phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, so interest is focused not only on phosphorescent dopants but also on phosphorescent host materials.

[0004] Currently, NPB, BCP, and Alq3, which are represented by the following formulas, are widely known as materials used in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant / host materials for light-emitting materials. Among light-emitting materials, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, are particularly useful as phosphorescent materials, offering significant advantages in terms of improved efficiency. These metal complex compounds are used as blue, green, and red dopants. Currently, CBP is demonstrating excellent properties as a phosphorescent host material.

[0005] However, while conventional luminescent materials have advantages in terms of luminescent properties, they have low glass transition temperatures and poor thermal stability, resulting in unsatisfactory life spans in organic EL devices. Therefore, there is a need to develop luminescent materials with superior performance. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel organic compound that can be used in an organic EL device and that has excellent thermal stability, electrochemical stability and hole transporting ability and can be used as a hole transport layer material.

[0007] Another object of the present invention is to provide an organic EL device which contains the novel organic compound, thereby achieving a low driving voltage, high luminous efficiency, and an improved lifespan. [Means for solving the problem]

[0008] In order to achieve the above object, the present invention provides a compound represented by the following [Chemical Formula 1].

[0009] [ka] (In the above formula, n≧1, X1 is O or S; Ring CyA is a C6 to C30 aromatic ring, n1 to n3 are each an integer of 0 to 3, L1 to L3 are the same or different and each independently represents a single bond or a C6 to C 30 and heteroarylene groups having 5 to 30 ring atoms, m1 is an integer from 0 to 8, m2 is an integer from 0 to 23, R1, R2, Ar1, and Ar2 are the same or different and each independently represent a hydrogen atom, a deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group to form a fused ring, The arylene groups and heteroarylene groups of L1 to L3, and the alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, (aryl)(heteroaryl)amine groups, and heteroarylamine groups of R1, R2, Ar1, and Ar2 each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C2 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and are unsubstituted or substituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amine groups having 5 to 60 ring atoms, and in this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0010] The present invention also provides an organic EL device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by [Chemical Formula 1].

[0011] According to one example, the organic layer containing the organic compound may be a hole transport layer. [Effects of the Invention]

[0012] The compound of the present invention has excellent thermal stability, electrochemical stability, and hole transporting ability, and therefore can be useful as an organic layer material for an organic EL device. In particular, when the compound of the present invention is used as a hole transporting layer material, an organic EL device having superior luminescence performance, low driving voltage, high efficiency, and long life characteristics compared to conventional materials can be produced, and a full-color display panel having improved performance and life can also be produced.

[0013] The effects of the present invention are not limited to the above-mentioned contents, and various other effects are included in this specification. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic EL element according to an example of the present invention. [Figure 2] FIG. 2 is a cross-sectional view schematically showing an organic EL element according to another example of the present invention. [Explanation of symbols]

[0015] 100: anode, 200: cathode, 300: organic layer, 310: hole injection layer, 320: hole transport layer, 330: light emitting layer, 340: electron transport layer, 350: electron injection layer. DETAILED DESCRIPTION OF THE INVENTION

[0016] The present invention will be described in detail below.

[0017] <New compounds> The present invention relates to a compound having an amine group substituted with an aryl group and / or a heteroaryl group, and a spiro ring connected to the amine group directly or via a linker group (e.g., a phenylene group), and wherein at least one deuterium (D) is essentially contained in the molecular structure, and is represented by the above [Chemical Formula 1]. The compound of [Chemical Formula 1] has excellent electrochemical stability, thermal stability, and carrier transport ability (especially hole transport ability), and the excellent stability of the chemical structure due to the deuterium (D) substitution is excellent. Therefore, when used in a hole transport layer, it can simultaneously realize the properties of an organic EL device, such as low voltage, high efficiency, and long life of the device.

[0018] Specifically, the compound represented by [Chemical Formula 1] according to the present invention contains at least one deuterium (D) in its molecular structure. Deuterium (D) has a higher molecular mass and a lower zero-point energy than hydrogen (H) in terms of potential energy. Therefore, deuterium is relatively difficult to dissociate in a reaction. However, the low zero-point energy of a compound substituted with deuterium increases the bond dissociation energy, reducing reactivity and increasing molecular stability (Molecules 2014, 19, Chem. Commun., 2014, 50, 14870-14872, J. Org. Chem. 2004, 69, 7212-7219). Therefore, the compound represented by [Chemical Formula 1] has superior chemical structural stability and thermal stability compared to a compound having the same structure but without deuterium, thereby significantly improving the lifespan of devices. In particular, when the compound of [Chemical Formula 1] above is used as a hole transport layer material for an organic EL device, the deuterium (D) substitution in the molecular structure enables the device to be driven at a low voltage, thereby improving the device's lifespan.

[0019] In addition, in the compound represented by [Chemical Formula 1] according to the present invention, the spiro ring has a monocyclic or polycyclic aromatic ring, such as a benzene ring or a naphthalene ring, fused to one benzene moiety on the fluorene side of the spiro[fluorene-xanthene] moiety or spiro[fluorene-thioxanthene] moiety, thereby exhibiting high hole mobility and excellent hole transport capability. Furthermore, the HOMO energy level and LUMO energy level of the compound represented by [Chemical Formula 1] are intermediate between the HOMO and LUMO energy levels of the hole injection layer and the light-emitting layer, thereby facilitating hole injection and transport. Therefore, when an organic EL device contains the compound of the present invention as a hole transport layer material, the luminous efficiency of the organic EL device can be improved, and the driving voltage can be reduced, thereby improving the device's lifetime.

[0020] In addition, the compound of [Chemical Formula 1] has physicochemical properties such as amorphous and high refractive index due to the introduction of an amine group substituted with aryl and / or heteroaryl at the benzene moiety on the other side of the fluorene in the spiro ring, thereby further improving luminous efficiency. Furthermore, the compound of [Chemical Formula 1] has excellent stability due to a high glass transition temperature (Tg), as well as excellent electrochemical stability.

[0021] As described above, the compound represented by [Chemical Formula 1] according to the present invention has excellent chemical structure stability, thermal stability, electrochemical stability, and hole transport property. Therefore, the compound represented by [Chemical Formula 1] according to the present invention can be used as an organic layer material of an organic EL device, preferably as a hole transport layer material or a hole transport auxiliary layer material, and more preferably as a hole transport layer material. Organic EL devices containing the compound according to the present invention exhibit significantly improved performance and lifespan, and full-color organic light-emitting panels using such organic EL devices can also maximize their performance.

[0022] In the compound represented by [Chemical Formula 1] according to the present invention, (D)n means the number of deuterium atoms (D) contained in the compound of [Chemical Formula 1], and n is ≧1. That is, the compound of the present invention has a structure in which a spiro ring and an amine group substituted with aryl and / or heteroaryl are connected on both sides of the molecule, either directly or via a linker group (e.g., a phenylene group), and the molecular structure must contain at least one deuterium atom (D). For example, 1≦n≦87, and more specifically, 1≦n≦47.

[0023] In addition, in the compound represented by [Chemical Formula 1], X1 is O or S. Thus, the spiro ring is a moiety in which an aromatic ring is fused to a benzene moiety on one side of the fluorene in a spiro[fluorene-xanthene], or a moiety in which an aromatic ring is fused to a benzene moiety on one side of the fluorene in a spiro[fluorene-thioxanthene]. The compound represented by [Chemical Formula 1] according to the present invention, which contains such a spiro ring, has excellent carrier transport ability because it has superior properties for both electrons and holes compared to compounds in which X1 is N or C. Therefore, when the compound represented by [Chemical Formula 1] according to the present invention is used as a hole transport layer material, the hole transport ability is improved, resulting in improved efficiency and driving voltage.

[0024] In the compound represented by the above [Chemical Formula 1], the ring CyA is a ring fused to the benzene moiety on one side of the fluorene in the spiro ring, and has C6 to C 30 Specifically, the aromatic ring is C6 to C 30 Monocyclic aromatic ring or C6-C 30The ring CyA may be a polycyclic aromatic ring. For example, the ring CyA may 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, a chrysene ring, a pentaphene ring, a pentacene ring, or a fused ring of two of the above rings, but is not limited thereto. Here, each ring in the polycyclic aromatic ring may be the same or different from each other.

[0025] Depending on the type of the ring CyA, the compound represented by [Chemical Formula 1] [ka] The moiety may be, but is not limited to, any one of the following moieties Mo1-1 to Mo1-3. [ka] In the above Moiati Mo1-1 to Mo1-3, * means the part that binds to [Chemical Formula 1], X1, m1, R1, and R2 are each as defined in [Chemical Formula 1] above. m3 is an integer from 0 to 9.

[0026] The compound represented by the above [Chemical Formula 1] may be a compound represented by any one of the following [Chemical Formula 2] to [Chemical Formula 22] depending on the binding position of deuterium contained in the compound and the type of ring CyA, but is not limited thereto.

[0027] [ka] [ka]

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[0028] In the compound represented by [Chemical Formula 1] according to the present invention, n1 to n3 are each an integer of 0 to 3, and specifically can be 0 or 1.

[0029] Here, 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 of 1 to 3, L1 to L3 are divalent linking groups (linkers), which may be the same or different from each other, and each independently represent a C6 to C 18 and heteroarylene groups having 5 to 18 ring atoms, specifically, C6 to C 18and heteroarylene groups having 5 to 18 ring atoms, wherein one or more L1s, one or more L2s, and one or more L3s may be the same or different.

[0030] In this case, the arylene group and heteroarylene group of L1 to L3 each independently represent a deuterium (D), a halogen (for example, -F, -Cl, -Br, -I, etc.), a cyano group (-CN), a nitro group (-NO2), an amino group (-NH2), a C1 to C2 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium (D), a cyano group (—CN), C1 to C6 20 Alkyl groups of C3 to C 20 Cycloalkyl groups having 3 to 20 ring atoms, heterocycloalkyl groups having 6 to 10 ring atoms, C6 to C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6 to C 30The arylamine group may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following arylamine groups, more specifically, it may be substituted with at least one deuterium (D). In this case, when there are a plurality of the above substituents, they may be the same or different.

[0031] According to one example, L1 to L3 are the same or different and each independently represents a single bond or is selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthalene group, a phenanthrene group, a triphenylene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, and combinations thereof, wherein the hydrogen of the phenylene group, the biphenylene group, the terphenylene group, the naphthalene group, the phenanthrene group, the triphenylene group, the carbazole group, the dibenzofuran group, the dibenzothiophene group, and the fluorene group is selected from the group consisting of deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C2 12 Alkyl groups of C6 to C 10 and heteroaryl groups having 5 to 10 ring atoms, or may be unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups having 5 to 10 ring atoms, and specifically, may be substituted with at least one deuterium (D).

[0032] In another example, the above L1 to L3 may be the same or different from each other and may each independently be the following linker-L1-1, but are not limited to this.

[0033] [ka] In the above linker L1-1, * means the part that binds to [Chemical Formula 1], (D) b is the number of deuterium atoms contained in the linker group L1-1, and is 0≦b≦12, specifically, 0≦b≦4; n4 is an integer from 0 to 3, m4 is an integer from 0 to 4, multiple R3's are the same or different, R3 is hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or fused with adjacent groups (e.g., R3-R3) to form a fused ring, and specifically, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C 20 alkyl groups, heterocycloalkyl groups with 3 to 20 atoms, C6 to C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6 to C 30 The arylamine groups are selected from the group consisting of:

[0034] In particular, when L1 is the above-mentioned linker L1-1, [ka] Moiety and [ka] The moieties can be introduced at the para position to each other. [ka] When a moiety is introduced (replaced), the above [ka] Based on the para position (i.e., the 4th carbon position), [ka] In this case, the compound of [Chemical Formula 1] can maximize the hole transport ability and facilitate intermolecular hole transfer, thereby lowering the driving voltage of the organic EL device.

[0035] In the compound represented by [Chemical Formula 1] according to the present invention, m1 is an integer of 0 to 8, and m2 is an integer of 0 to 23, specifically, m2 is an integer of 0 to 9, and more specifically, m2 can be an integer of 1 to 5.

[0036] Here, when m1 and m2 are each 0, it means that hydrogen is not substituted with the substituents R1 and R2, respectively. On the other hand, when m1 is an integer of 1 to 8, it means that hydrogen is substituted with the substituent R1, and when m2 is an integer of 1 to 23, it means that hydrogen is substituted with the substituent R2. In this case, multiple R1s may be the same or different from each other, and multiple R2s may be the same or different from each other.

[0037] The R1 and R2 are the same or different and each independently represents hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or fused with adjacent groups (e.g., R1-R1, R2-R2, etc.) to form a fused ring, specifically, R1 and R2 are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 20 Alkyl groups of C3 to C 20 Cycloalkyl groups, heterocycloalkyl groups with 3 to 20 atoms, C6 to C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6 to C 30 More specifically, R1 and R2 are deuterium or C6-C arylamines substituted with deuterium. 30 and heteroaryl groups having 5 to 30 ring atoms.

[0038] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group of R1 and R2 each independently represent hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium (D), a cyano group (—CN), C1 to C6 20 Alkyl groups of C3 to C 20 Cycloalkyl groups having 3 to 20 ring atoms, heterocycloalkyl groups having 6 to 10 ring atoms, C6 to C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C6 to C 30and more specifically, it may be substituted with at least one deuterium (D). In this case, when there are a plurality of the above substituents, they may be the same or different.

[0039] In one example, R1 and R2 are the same or different and are each independently selected from the group consisting of deuterium (D), methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, and naphthyl. Specifically, R1 and R2 may each independently be deuterium. In this case, the methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, and naphthyl groups of R1 and R2 may be substituted with at least one deuterium (D).

[0040] In the compound represented by [Chemical Formula 1] according to the present invention, Ar1 and Ar2 are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 Alkyl groups of C2 to C 40 Alkynyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 Arylboron groups, C6-C 60 Arylphosphine groups, C6-C 60 Arylphosphine oxide group, C6-C 60 Arylamine groups, C6-C 60and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group (e.g., Ar1-L2, Ar2-L3) to form a fused ring.

[0041] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group of Ar1 and Ar2 each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, an amino group, a C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkyl groups of C3 to C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60and heteroarylamine groups having 5 to 60 ring atoms, specifically, each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D), a cyano group (—CN), a C1 to C20 alkyl group, a C3 to C20 cycloaryl group, a heterocycloaryl group having 3 to 20 ring atoms, a C6 to C30 aryl group, a heteroaryl group having 5 to 30 ring atoms, and a C6 to C30 arylamine group, more specifically, each independently substituted or unsubstituted with one or more substituents selected from the group consisting of at least one deuterium (D). In this case, when there are multiple such substituents, they may be the same or different.

[0042] According to one example, Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of a C6 to C60 aryl group and a heteroaryl group having 5 to 60 ring atoms, wherein the aryl group and heteroaryl group of Ar1 and Ar2 may be substituted with one or more deuterium atoms.

[0043] In another example, Ar1 and Ar2 may be the same or different and may each independently be selected from the group consisting of the following substituents S1-1 to S1-3, but are not limited thereto.

[0044] [ka] (In the above substituents S1-1 to S1-3, * means the part that binds to [Chemical Formula 1], (D) d1 is the number of deuterium (D) contained in the substituent S1-1, and 0≦d1≦15, specifically 0≦d1≦15, (D) d2 is the number of deuterium (D) contained in the substituent S1-2, and 0≦d2≦7, specifically 0≦d2≦7, (D) d3is the number of deuterium (D) contained in the substituent S1-3, and 0≦d3≦8, specifically 0≦d3≦8, o1 to o3 are each 0 or 1, provided that 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 or different and each independently represent a hydrogen atom, a deuterium atom (D), a halogen atom, a cyano group, a nitro group, an amino group, a C1 to C2 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or fused with adjacent groups (e.g., R3-R3, Ar3-Ar4, etc.) to form a fused ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group of Ar3 to Ar5 each independently represent deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C2 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and wherein when there are a plurality of the above-mentioned substituents, these may be the same or different.

[0045] The hydrogen atoms of the above-mentioned substituents S1-1 to S1-3 can be deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C 12 Alkyl groups of C6 to C 10and heteroaryl groups having 5 to 10 ring atoms, and specifically, may be substituted with deuterium (D).

[0046] In another example, Ar1 and Ar2 may be the same or different and may each independently be selected from the group consisting of the following substituents S2-1 to S2-12, but are not limited thereto.

[0047] [ka] [ka] In the above substituents S2-1 to S2-12, * means the part that binds to [Chemical Formula 1], (D) d1 is the number of deuterium (D) contained in each of the substituents S2-1 to S2-4, and is 0≦d1≦15, specifically 1≦d1≦15, (D) d2 is the number of deuterium (D) contained in each of the substituents S2-5 to S2-11, and is 0≦d2≦7, specifically 1≦d2≦4, (D) d3 is the number of deuterium (D) contained in the substituent S2-12, and 0≦d3≦8, specifically 1≦d3≦4.

[0048] The hydrogen atoms of the above-mentioned substituents S2-1 to S2-12 can be deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano group (-CN), nitro group (-NO2), amino group (-NH2), C1 to C 12 Alkyl groups of C6 to C 10 and heteroaryl groups having 5 to 10 ring atoms, and specifically, may be substituted with deuterium (D).

[0049] Depending on the types of the rings CyA, L1, and Ar1, the compound represented by [Chemical Formula 1] above may be represented by any one of the following [Chemical Formula 23] to [Chemical Formula 31], but is not limited thereto.

[0050] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] During the above process, X1, n1 to n3, L2, L3, m1, R1, R2, and Ar1 are each as defined in [Chemical Formula 1] above. (D)n is the number of deuterium (D) contained in the compound, and is 1≦n≦87, specifically 1≦n≦53; m3 is an integer from 0 to 9, m4 is an integer from 0 to 4, o1 to o3 are each 0 or 1, provided that 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 or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkynyl groups, C3-C 40 Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 atoms, C6 to C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group to form a fused ring, The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group of Ar3 to Ar5 each independently represent deuterium (D), halogen, cyano group, nitro group, amino group, C1 to C6 40 Alkyl groups of C2 to C 40 Alkenyl groups, C2-C 40 Alkyl groups of C3 to C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 6 to 40 ring atoms, 60aryl groups, heteroaryl groups with 5 to 60 ring atoms, C1 to C 40 Alkyloxy 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 group, C6-C 60 Arylamine groups, C6-C 60 and heteroarylamine groups having 5 to 60 ring atoms, and when there are a plurality of the above-mentioned substituents, these may be the same or different.

[0051] The compound represented by [Chemical Formula 1] according to the present invention can be embodied by the following compounds 1 to 120, but is not limited thereto.

[0052] [ka] [ka] [ka] [ka]

[0053] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0054] In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0055] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl and 2-propynyl.

[0056] 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 thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, etc.

[0057] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, S, or Se. Examples include, but are not limited to, morpholine and piperazine. Here, the number of ring atoms refers to the number of atoms forming the ring, i.e., the number of atoms.

[0058] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and consisting of a single ring or a combination of two or more rings. The two or more rings may be in a pendant or condensed form. Examples of such an aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0059] In the present invention, the term "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 ring atoms. In this case, one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms, are substituted with heteroatoms such as N, O, S, or Se. Two or more rings may be in a pendant or fused form, and may even be fused with an aryl group. Examples of such heteroaryl groups include, but are not limited to, six-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl. Here, the number of nuclear atoms means the number of atoms forming a ring, that is, the number of ring atoms.

[0060] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0061] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0062] In the present invention, "alkylsilyl" means a silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyl. Furthermore, "arylsilyl" means a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0063] In the present invention, the term "alkylboron group" refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms, and the term "arylboron group" refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.

[0064] In the present invention, the term "alkylphosphinyl group" refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups. In addition, in the present invention, the term "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0065] In the present invention, the term "arylamine" refers to an amine substituted with an aryl having 6 to 40 carbon atoms, and includes not only mono- but also di-arylamine.

[0066] <Organic electroluminescent device> Furthermore, the present invention relates to an organic electroluminescent device (hereinafter abbreviated as "organic EL device") containing the compound represented by the above-mentioned [Chemical Formula 1].

[0067] Specifically, the organic EL device according to the present invention includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, at least one of which includes a compound represented by Formula 1. The compounds may be used alone or in combination.

[0068] The one or more organic layers are any 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 of these organic layers contains the compound represented by [Chemical Formula 1]. Preferably, the organic layer containing the compound of [Chemical Formula 1] may be a hole transport layer.

[0069] According to one example, the one or more organic layers include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer, and the hole transport layer may be a compound represented by the above [Chemical Formula 1].

[0070] The compound represented by [Chemical Formula 1] is included in an organic electroluminescent device as a hole transport layer material. In this case, the compound represented by [Chemical Formula 1] has a high glass transition temperature, high hole mobility, and high hole transport ability. Due to the appropriate HOMO and LUMO energy levels between the hole injection layer and the light emitting layer, holes can be smoothly injected and transported from the hole injection layer to the light emitting layer. It also has amorphous crystallinity and a high refractive index. Therefore, organic electroluminescent devices containing the compound represented by [Chemical Formula 1] can have improved efficiency (luminous efficiency and power efficiency), lifetime, brightness, driving voltage, thermal stability, etc. The structure of such an organic EL device of the present invention is not particularly limited, but for example, an anode 100, one or more organic layers 300, and a cathode 200 are laminated in this order on a substrate (see FIGS. 1 and 2). Furthermore, the device may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0071] According to one example, the organic EL device has a structure in which an anode 100, a hole injection layer 310, a hole transport layer 320, an emitting layer 330, an electron transport layer 340, and a cathode 200 are sequentially stacked on a substrate, as shown in FIG. Optionally, as shown in FIG. 2, an electron injection layer 350 may be disposed between the electron transport layer 340 and the cathode 200. Also, a hole blocking layer (not shown) may be disposed between the emitting layer 330 and the electron transport layer 340. The organic EL device of the present invention may be fabricated by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers 300 (e.g., the hole transport layer 320) contains the compound represented by Formula 1.

[0072] The organic layer can be formed by vacuum deposition or solution coating, including, but not limited to, spin coating, deep coating, doctor blading, inkjet printing, and thermal transfer.

[0073] The substrate that can be used in the present invention is not particularly limited, and examples thereof include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like.

[0074] Examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black.

[0075] Examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al and LiO / Al.

[0076] The hole injection layer, light emitting layer, electron transport layer and electron injection layer are not particularly limited, and materials well known in the art can be used. [Example]

[0077] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0078] [Preparation Example 1] Synthesis of Compound J-1 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to phen-d5-ol (9.91 g, 100 mmol) and 9-bromo-7H-benzo[c]fluoren-7-one (3.09 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-1 (2.34 g, 50% yield).

[0079] [Preparation Example 2] Synthesis of Compound J-2 Step 1: Synthesis of 2-bromo-11H-benzo[b]fluoren-11-one-5,6,7,8,9,10-d6 [ka] 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 ethyl alcohol and refluxed for 6 hours. The reaction solution was cooled to 0 ° C., and the precipitated solid was filtered, washed with methyl alcohol, and filtered under reduced pressure to obtain compound 2-bromo-11H-benzo[b]fluoren-11-one-5,6,7,8,9,10-d6 (1.54 g, 49% yield).

[0080] <Step 2> Synthesis of compound J-2 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to phen-2,4,6-d3-ol (9.71 g, 100 mmol) and 2-bromo-11H-benzo[b]fluoren-11-one-5,6,7,8,9,10-d6 (3.15 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-2 (2.26 g, 48% yield).

[0081] [Preparation Example 3] Synthesis of Compound J-3 Step 1: Synthesis of 9-bromo-11H-benzo[a]fluoren-11-one-7,8,10-d3 [ka] 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 stirred at 110 °C for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the target compound, 9-bromo-11H-benzo[a]fluoren-11-one-7,8,10-d3 (1.46 g, 47% yield), was obtained using column chromatography.

[0082] <Step 2> Synthesis of compound J-3 [ka] Phenol (9.41 g, 100 mmol), 9-bromo-11H-benzo[a]fluoren-11-one-7,8,10-d3 (3.12 g, 10 mmol), and methanesulfonic acid (MsOH) (3.84 g, 40 mmol) were added, and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-3 (2.13 g, 46% yield).

[0083] [Preparation Example 4] Synthesis of Compound J-4 <Step 1> Synthesis of methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3 [ka] 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, and 25 ml of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added MgSO4, and filtered. After removing the solvent from the filtered organic layer, the target compound, methyl 2-bromo-6-(naphthalen-1-yl)benzoate-3,4,5-d3 (1.54 g, 45% yield), was obtained using column chromatography.

[0084] Step 2: Synthesis of 2-bromo-6-(naphthalen-1-yl)benzoic-3,4,5-d3 acid [ka] 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 hours. The temperature was lowered to room temperature and the mixture was acidified with 2 M hydrochloric acid. The precipitate was filtered and recrystallized from ethanol to obtain the desired compound, 2-bromo-6-(naphthalen-1-yl)benzoic-3,4,5-d3 acid (1.45 g, 44% yield).

[0085] Step 3: Synthesis of 8-bromo-7H-benzo[c]fluoren-7-one-9,10,11-d3 [ka] 2-Bromo-6-(naphthalen-1-yl)benzoic-3,4,5-d3 acid (3.30 g, 10 mmol) was dissolved in 100 mL of methanesulfonic acid and stirred for 24 hours. After stirring, ice water was poured over the solution to precipitate the solid. The precipitated solid was filtered, washed with distilled water, and then stirred in aqueous sodium bicarbonate for 3 hours. After filtration, the solid was neutralized with distilled water and recrystallized with acetic acid to obtain the desired compound, 8-bromo-7H-benzo[c]fluoren-7-one-9,10,11-d3 (1.34 g, 43% yield).

[0086] <Step 4> Synthesis of compound J-4 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to phen-2,6-d2-ol (9.61 g, 100 mmol) and 8-bromo-7H-benzo[c]fluoren-7-one-9,10,11-d3 (3.12 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-4 (1.95 g, 42% yield).

[0087] [Preparation Example 5] Synthesis of Compound J-5 <Step 1> Synthesis of methyl 4-chloro-2-(naphthalen-1-yl-d7)benzoate [ka] 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, and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, and the resulting mixture was filtered after adding MgSO4. The solvent in the filtered organic layer was removed, and the target compound, methyl 4-chloro-2-(naphthalen-1-yl-d7)benzoate (1.24 g, 41% yield), was obtained using column chromatography.

[0088] Step 2: Synthesis of 4-chloro-2-(naphthalen-1-yl-d7)benzoic acid [ka] 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 then lowered to room temperature, and the mixture was acidified with 2 M hydrochloric acid. The precipitate was filtered and recrystallized from ethanol to obtain the desired compound, 4-chloro-2-(naphthalen-1-yl-d7)benzoic acid (1.15 g, 40% yield).

[0089] Step 3: Synthesis of 10-chloro-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 [ka] 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. After stirring, ice water was poured over the solution to precipitate the solid. The precipitated solid was filtered, washed with distilled water, and stirred for 3 hours after adding aqueous sodium bicarbonate. The solid was neutralized with filtered distilled water and recrystallized with acetic acid to obtain compound 10-chloro-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 (1.11 g, 41%).

[0090] <Step 4> Synthesis of compound J-5 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to phen-4-d-ol (9.51 g, 100 mmol) and 10-chloro-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 (2.70 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-5 (1.78 g, 42% yield).

[0091] [Preparation Example 6] Synthesis of Compound J-6 Step 1: Synthesis of methyl 3-bromo-2-(naphthalen-1-yl-d7)benzoate [ka] 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, and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound, methyl 3-bromo-2-(naphthalen-1-yl-d7)benzoate (1.49 g, 43% yield), was obtained using column chromatography.

[0092] Step 2: Synthesis of 3-bromo-2-(naphthalen-1-yl-d7)benzoic acid [ka] 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 then lowered to room temperature, and the mixture was acidified with 2 M hydrochloric acid. The precipitate was filtered and recrystallized from ethanol to obtain the desired compound, 3-bromo-2-(naphthalen-1-yl-d7)benzoic acid (1.47 g, 44% yield).

[0093] Step 3: Synthesis of 11-bromo-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 [ka] 3-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. Afterwards, ice water was poured into the solution to precipitate the solid. The precipitated solid was filtered, washed with distilled water, and stirred in aqueous sodium bicarbonate for 3 hours. After filtration, the solid was neutralized with distilled water and recrystallized from acetic acid to obtain compound 11-bromo-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 (1.41 g, 45% yield).

[0094] <Step 4> Synthesis of compound J-6 [ka] In a sintered 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 stirred for 1 hour. Next, 11-bromo-7H-benzo[c]fluoren-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 gradually warmed to room temperature, quenched with NH4Cl, and then concentrated under reduced pressure. The concentrated solution was carefully mixed with 30 mL of acetic acid, followed by the addition of 15 mL of fuming HCl. 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 washed with methanol to obtain compound J-6 (2.16 g, 46% yield).

[0095] [Preparation Example 7] Synthesis of Compound J-7 <Step 1> Synthesis of methyl 5-bromo-2-(naphthalen-1-yl-d7)benzoate [ka] 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, and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, and the resulting mixture was filtered after adding MgSO4. The solvent in the filtered organic layer was removed, and the target compound, methyl 5-bromo-2-(naphthalen-1-yl-d7)benzoate (1.63 g, 47% yield), was obtained using column chromatography.

[0096] Step 2: Synthesis of 5-bromo-2-(naphthalen-1-yl-d7)benzoic acid [ka] 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 then lowered to room temperature, and the mixture was acidified with 2 M hydrochloric acid. The precipitate was filtered and recrystallized from ethanol to obtain the desired compound, 5-bromo-2-(naphthalen-1-yl-d7)benzoic acid (1.60 g, 48% yield).

[0097] Step 3: Synthesis of 9-bromo-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 [ka] 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. After stirring, ice water was poured into the solution to precipitate the solid. The precipitated solid was filtered, washed with distilled water, and stirred in aqueous sodium bicarbonate for 3 hours. After filtration, the solid was neutralized with distilled water and recrystallized with acetic acid to obtain compound 9-bromo-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 (1.54 g, 49% yield).

[0098] <Step 4> Synthesis of compound J-7 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to benzene-3,5-d2-thiol (11.21 g, 100 mmol) and 9-bromo-7H-benzo[c]fluoren-7-one-1,2,3,4,5,6-d6 (3.15 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-7 (2.43 g, 50% yield).

[0099] [Preparation Example 8] Synthesis of Compound J-8 Step 1: Synthesis of 3-bromo-11H-benzo[b]fluoren-11-one-5,10-d2 [ka] 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 ethyl alcohol and refluxed for 6 hours. The reaction solution was cooled to 0 °C, and the precipitated solid was filtered, washed with methyl alcohol, and filtered under reduced pressure to obtain compound 3-bromo-11H-benzo[b]fluoren-11-one-5,10-d2 (1.52 g, 49% yield).

[0100] <Step 2> Synthesis of compound J-8 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to benzenethiol (11.01 g, 100 mmol) and 3-bromo-11H-benzo[b]fluoren-11-one-5,10-d2 (3.11 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-8 (2.30 g, 48% yield).

[0101] [Preparation Example 9] Synthesis of Compound J-9 Step 1: Synthesis of 7-bromo-11H-benzo[a]fluoren-11-one-1-d [ka] 1-Naphtho-8-d acid (1.73 g, 10 mmol), diaryliodonium salt (11.75 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 stirred at 110 °C for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the target compound, 7-bromo-11H-benzo[a]fluoren-11-one-1-d (1.45 g, 47% yield), was obtained using column chromatography.

[0102] <Step 2> Synthesis of compound J-9 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to benzene-d5-thiol (11.52 g, 100 mmol) and 7-bromo-11H-benzo[a]fluoren-11-one-1-d (3.10 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-9 (2.23 g, 46% yield).

[0103] [Preparation Example 10] Synthesis of Compound J-10 <Step 1> Synthesis of methyl 2-bromo-6-(naphthalen-2-yl)benzoate-3,4,5-d3 [ka] Methyl 2,6-dibromobenzoate-3,4,5-d3 (2.96 g, 10 mmol), naphthalen-2-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, and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, and the resulting mixture was filtered after adding MgSO4. The solvent in the filtered organic layer was removed, and the target compound, methyl 2-bromo-6-(naphthalen-2-yl)benzoate-3,4,5-d3 (1.54 g, 45% yield), was obtained using column chromatography.

[0104] Step 2: Synthesis of 2-bromo-6-(naphthalen-2-yl)benzoic-3,4,5-d3 acid [ka] 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 and the mixture was acidified with 2 M hydrochloric acid. The precipitate was filtered and recrystallized from ethanol to obtain the compound 2-bromo-6-(naphthalen-2-yl)benzoic-3,4,5-d3 acid (1.45 g, 44% yield).

[0105] Step 3: Synthesis of 1-bromo-11H-benzo[b]fluoren-11-one-2,3,4-d3 [ka] 2-Bromo-6-(naphthalen-2-yl)benzoic-3,4,5-d3 acid (3.30 g, 10 mmol) was dissolved in 100 mL of methanesulfonic acid and stirred for 24 hours. After stirring, ice water was poured into the solution to precipitate the solid. The precipitated solid was filtered, washed with distilled water, and stirred in aqueous sodium bicarbonate for 3 hours. After filtration, the solid was neutralized with distilled water and recrystallized with acetic acid to obtain the compound 1-bromo-11H-benzo[b]fluoren-11-one-2,3,4-d3 (1.34 g, 43% yield).

[0106] <Step 4> Synthesis of compound J-10 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to benzene-4-d-thiol (11.11 g, 100 mmol) and 1-bromo-11H-benzo[b]fluoren-11-one-2,3,4-d3 (3.12 g, 10 mmol), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-10 (2.02 g, 42% yield).

[0107] [Preparation Example 11] Synthesis of Compound J-11 [ka] Methanesulfonic acid (MsOH) (3.84 g, 40 mmol) was added to 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), and the mixture was heated to reflux at 120 °C for 12 hours. The reaction mixture was then cooled to room temperature, and purified water was added to the reaction mixture to terminate the reaction. After the reaction was completed, the mixture was extracted with CHCl to separate the organic layer. The separated organic layer was neutralized with saturated calcium carbonate and washed with distilled water. The washed organic layer was then dried over anhydrous MgSO, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the target compound J-11 (1.97 g, 41% yield).

[0108] [Preparation Example 12] Synthesis of Compound J-12 [ka] In a sintered 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 stirred for 1 hour. Next, 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 gradually warmed to room temperature, quenched with NH4Cl, and concentrated under reduced pressure. The concentrated solution was carefully mixed with 30 mL of acetic acid, followed by the addition of 5 mL of fuming HCl and stirring at 75 °C for 6 hours. The mixture was then cooled to room temperature, and the precipitated solid was filtered under reduced pressure and washed with methanol to obtain the desired compound J-12 (1.91 g, 40% yield).

[0109] [Preparation Example 13] Synthesis of Compound J-13 [ka] 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 added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added MgSO4, and filtered. The solvent in the filtered organic layer was removed, and the target compound J-13 (3.19 g, 43% yield) was obtained using column chromatography.

[0110] [Preparation Example 14] Synthesis of Compound J-14 [ka] 9-Bromospiro[benzo[c]fluorene-7,9'-xanthene] (4.61 g, 10 mmol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-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 added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added MgSO4, and filtered. The filtered organic layer was removed of the solvent and purified by column chromatography to obtain the desired compound J-14 (3.22 g, 44% yield).

[0111] [Preparation Example 15] Synthesis of Compound J-15 [ka] 9-Bromospiro[benzo[c]fluorene-7,9'-xanthene] (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, and 25 mL of HO and stirred at 100 °C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added MgSO4, and filtered. The solvent in the filtered organic layer was removed, and the target compound J-15 (3.63 g, 45% yield) was obtained using column chromatography.

[0112] [Synthesis Example 1] Synthesis of Compound 1 [ka] Compound J-1 (4.69 g, 10 mmol) synthesized in Preparative Example 1, di([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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 1 (2.91 g, 41% yield) was obtained using column chromatography. Mass: [(M+H) + ]:709

[0113] [Synthesis Example 2] Synthesis of Compound 2 [ka] Compound J-2 (4.71 g, 10 mmol) synthesized in Preparative 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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 2 (2.69 g, 42% yield) was obtained using column chromatography. Mass: [(M+H) + ]:640

[0114] [Synthesis Example 3] Synthesis of Compound 3 [ka] Compound J-3 (4.64 g, 10 mmol) synthesized in Preparative Example 3, N-([1,1'-biphenyl]-2-yl-4'-d)-9,9-dimethyl-9H-fluoren-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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and compound 3 (3.20 g, 43% yield) was obtained using column chromatography. Mass: [(M+H) + ]:745

[0115] [Synthesis Example 4] Synthesis of Compound 4 [ka] Compound J-4 (4.64 g, 10 mmol) synthesized in Preparative 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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and the mixture was filtered after adding MgSO4. The solvent in the filtered organic layer was removed, and the target compound 4 (3.30 g, 44% yield) was obtained using column chromatography. Mass: [(M+H) + ]:750

[0116] [Synthesis Example 5] Synthesis of Compound 5 [ka] Compound J-5 (4.24 g, 10 mmol), synthesized in Preparative 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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 5 (2.85 g, 45% yield) was obtained using column chromatography. Mass: [(M+H) + ]:634

[0117] [Synthesis Example 6] Synthesis of Compound 6 [ka] Compound J-6 (4.71 g, 10 mmol) synthesized in Preparative 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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 6 (3.51 g, 46% yield) was obtained using column chromatography. Mass: [(M+H) + ]:764

[0118] [Synthesis Example 7] Synthesis of Compound 7 [ka] Compound J-7 (4.87 g, 10 mmol) synthesized in Preparative Example 7, N-(4-(9H-carbazol-9-yl-d)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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 7 (4.30 g, 47% yield) was obtained using column chromatography. Mass: [(M+H) + ]:915

[0119] [Synthesis Example 8] Synthesis of Compound 8 [ka] Compound J-8 (4.79 g, 10 mmol) synthesized in Preparative 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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 8 (3.38 g, 48% yield) was obtained using column chromatography. Mass: [(M+H) + ]:705

[0120] [Synthesis Example 9] Synthesis of Compound 9 [ka] Compound J-9 (4.86 g, 10 mmol) synthesized in Preparative Example 9, N-phenylbenzene-2,4,6-d-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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, and MgSO4 was added and filtered. The solvent in the filtered organic layer was removed, and the target compound 9 (2.83 g, 49% yield) was obtained using column chromatography. Mass: [(M+H) + ]:577

[0121] [Synthesis Example 10] Synthesis of Compound 10 [ka] Compound J-10 (4.86 g, 10 mmol) synthesized in Preparative Example 10, N-(9,9-dimethyl-9H-fluoren-4-yl-1,2,3,5,6,7,8-d7)-9,9-dimethyl-9H-fluoren-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) were added to 100 mL of toluene and stirred at 120 °C for 6 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added MgSO4, and filtered. The solvent in the filtered organic layer was removed, and the target compound 10 (4.08 g, 50% yield) was obtained using column chromatography. Mass: [(M+H) + ]:817

[0122] [Synthesis Example 11] Synthesis of Compound 11 [ka] Compound J-11 (4.81 g, 10 mmol) synthesized in Preparative 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, and 25 ml of H2O and stirred at 100 °C for 8 hours. After the reaction was completed, the mixture was extracted with methylene chloride, added with MgSO4, and filtered. The solvent in the filtered organic layer was removed, and the target compound 11 (4.12 g, 49% yield) was obtained using column chromatography. Mass: [(M+H) + ]:842

[0123] [Synthesis Example 12] Synthesis of Compound 12 [ka] Compound J-12 (4.79 g, 10 mmol) synthesized in Preparative Example 12, N-(dibenzo[b,d]furan-4-yl-6,7,8,9-d)-9-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazol-3-amine-2,6,7-d (6.33 g, 10 mmol), Pd(PPh) (0.34 g, 0.3 mmol), and KCO (2.76 g, 20 mmol) were added to 100 ml of toluene, 25 ml of ethanol, and 25 ml of HO and stirred at 100°C for 8 hours. After the reaction was complete, the mixture was extracted with methylene chloride, added with MgSO, and filtered. After removing the solvent from the filtered organic layer, the target compound 12 (4.34 g, 48% yield) was obtained using column chromatography. Mass: [(M+H) + ]:906

[0124] [Synthesis Example 13] Synthesis of Compound 13 [ka] Compound J-13 (7.41 g, 10 mmol) synthesized in Preparative Example 13 was dissolved in perdeuterated benzene (CD) (84.15 g, 1 mol), and CFSOD (7.55 g, 50 mmol) was added. The mixture was stirred at 80°C. A sample was taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, the mixture was cooled to room temperature. LC-MS analysis confirmed that deuterium substitution was possible at various rates depending on the conditions. The reaction was terminated by adding NaCO in D0, and the organic solvent was concentrated. Recrystallization using toluene and acetone solvents yielded the deuterated target compound 13 (3.64 g, 47% yield). Mass: [(M+H) + ]:775

[0125] [Synthesis Example 14] Synthesis of Compound 14 [ka] Compound J-14 (7.31 g, 10 mmol) synthesized in Preparative Example 14 was dissolved in perdeuterated benzene (CD) (84.15 g, 1 mol), and CFSOD (7.55 g, 50 mmol) was added. The mixture was stirred at 80°C. A sample was taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, the mixture was cooled to room temperature. LC-MS analysis confirmed that deuterium substitution was possible at various rates depending on the conditions. The reaction was terminated by adding NaCO in D0, and the organic solvent was concentrated. Recrystallization using toluene and acetone solvents yielded the deuterated target compound 14 (3.51 g, 46% yield). Mass: [(M+H) + ]:765

[0126] [Synthesis Example 15] Synthesis of Compound 15 [ka] Compound J-15 (8.08 g, 10 mmol) synthesized in Preparative Example 15 was dissolved in perdeuterated benzene (CD) (84.15 g, 1 mol), and CFSOD (7.55 g, 50 mmol) was added. The mixture was stirred at 80°C. A sample was taken and the degree of deuteration was measured by LC-MS. After the exchange reaction was completed, the mixture was cooled to room temperature. LC-MS analysis confirmed that deuterium substitution was possible at various rates depending on the conditions. The reaction was terminated by adding NaCO in D0, and the organic solvent was concentrated. Recrystallization using toluene and acetone solvents yielded the deuterated target compound 15 (3.80 g, 45% yield). Mass: [(M+H) + ]:845

[0127] [Example 15] Fabrication of blue organic EL element Compound 1 synthesized in Synthesis Example 1 above was purified by sublimation to high purity by a conventional method, and then a blue organic EL device was fabricated according to the following process.

[0128] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, manufactured by Fashin Tech Co., Ltd.) where it was cleaned using UV for 5 minutes before being transferred to a vacuum deposition machine.

[0129] An organic EL device was fabricated by stacking 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 described above. The structures of HI, HAT-CN6, EB, BH, BD, HB, ET, and Liq used in this study are as follows:

[0130] [ka]

[0131] [Examples 2 to 15] Fabrication of blue organic EL devices Blue organic EL devices were produced in the same manner as in Example 1, except that the hole transport layer materials in Table 1 were used instead of Compound 1 used in Example 1 as the hole transport layer material.

[0132] [Comparative Examples 1 to 3] Production of blue organic EL elements A blue organic EL device was fabricated in the same manner as in Example 1, except that compounds HI, HT1, and HT2 were used instead of compound 1 used as the hole transport layer material in Example 1. The structures of HI, HT1, and HT2 used here are as follows:

[0133] [ka]

[0134] [Evaluation example 1] For the organic EL devices manufactured in Examples 1 to 15 and Comparative Examples 1 to 3, a current density of 10 mA / cm 2 The driving voltage, emission wavelength, and current efficiency were measured, and the results are shown in Table 1 below.

[0135] [Table 1]

[0136] As shown in Table 1, it was confirmed that the organic EL devices obtained in Examples 1 to 15, in which the compounds of the present invention were used in the hole transport layer, were superior in terms of driving voltage, emission peak, and current efficiency to the organic EL devices obtained in Comparative Examples 1 to 3, in which conventional hole transport layer materials (e.g., HI) or compounds not containing deuterium (D) (e.g., HT1 and HT2) were used in the hole transport layer.

Claims

1. A compound represented by the following [Chemical Formula 1]: 【Chemistry 1】 (In the formula, n≧1, Ring CyA is C ６ ~C ３０ is an aromatic ring of X １ is O or S, n1 to n3 are each an integer of 0 to 3, L １ ~L ３ are the same or different and each independently represent a single bond or C ６ ~C ３０ and heteroarylene groups having 5 to 30 ring atoms, m1 is an integer from 0 to 8, m2 is an integer from 0 to 23, R １ , R ２ , Ar １ and Ar ２ are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group to form a fused ring, The above L １ ~L ３ Arylene groups and heteroarylene groups of the above R １ , R ２ , Ar １ and Ar ２ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, and wherein when there are a plurality of the above-mentioned substituents, they may be the same or different.

2. In the compound represented by the above [Chemical Formula 1], 【Chemistry 2】 The compound of claim 1, wherein the moiety is any one of the following moieties Mo1-1 to Mo1-3: 【Transformation 3】 (In the above moieties Mo1-1 to Mo1-3, X １ , m1, R １ , R ２ are each as defined in claim 1, m3 is an integer from 0 to 9.

3. The compound represented by the above [Chemical Formula 1] is represented by any one of the following [Chemical Formula 2] to [Chemical Formula 22]. 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 (In the formula, X １ , m1, R １ , R ２ , n1 to n3, L １ ~L ３ , Ar １ , Ar ２ are each 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 above L １ ~L ３ are the same or different from each other and each independently represent the following linker L1-1: 【Chemistry 25】 (In the above linker L1-1, (D) ｂ is the number of deuterium atoms contained in the linker L1-1, and 0≦b≦12; n4 is an integer from 0 to 3, m4 is an integer from 0 to 4, R ３ represents hydrogen, deuterium (D), halogen, cyano, nitro, amino, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, or are fused with adjacent groups to form a fused ring.)

5. The above Ar １ and Ar ２ are the same or different and are each independently selected from the group consisting of the following substituents S1-1 to S1-3: 【Chemistry 26】 (In the above substituents S1-1 to S1-3, (D) ｄ１ is the number of deuterium (D) contained in the substituent S1-1, and 0≦d1≦15; (D) ｄ２ is the number of deuterium (D) contained in the substituent S1-2, and 0≦d2≦7; (D) ｄ３ is the number of deuterium (D) contained in the substituent S1-3, and 0≦d3≦8; o1 to o3 are each 0 or 1, provided that 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, Y １ is O, S, C(Ar ３ ) (Ar ４ ), and N(Ar ５ ) selected from the group consisting of R ３ , and Ar ３ ~Ar ５ are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group to form a fused ring, The above Ar ３ ~Ar ５ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, and are unsubstituted or substituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amine groups of the formula (I) and heteroarylamine groups having 5 to 60 ring atoms, and when there are a plurality of the above substituents, they may be the same or different.

6. The compound represented by the above [Chemical Formula 1] is represented by any one of the following [Chemical Formula 23] to [Chemical Formula 31]. 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 (In the formula, X １ , n1 to n3, L ２ , L ３ , m1, R １ , R ２ , Ar １ are each as defined in claim 1, (D)n is the number of deuterium (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, provided that 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, Y １ is O, S, C(Ar ３ ) (Ar ４ ), and N(Ar ５ ) selected from the group consisting of R ３ , and Ar ３ ~Ar ５ are the same or different and each independently represent hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, or fused with an adjacent group to form a fused ring, The above Ar ３ ~Ar ５ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, (aryl)(heteroaryl)amine group, and heteroarylamine group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, an amino group, C １ ~C ４０ alkyl group of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms, a heterocycloalkyl group having 3 to 40 ring atoms, ６ ~C ６０ an aryl group having 5 to 60 ring atoms; a heteroaryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ alkylboron groups of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ an arylamine group of C ６ ~C ６０ and heteroarylamine groups having 5 to 60 ring atoms, and are unsubstituted or substituted with one or more substituents selected from the group consisting of (aryl)(heteroaryl)amine groups of the formula (I) and heteroarylamine groups having 5 to 60 ring atoms, and when there are a plurality of the above substituents, they may be the same or different.

7. The compound represented by the above [Chemical Formula 1] is any one of the following compounds 1 to 120: 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】

8. An organic EL device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, 8. An organic EL device, wherein at least one of the one or more organic layers comprises the organic compound according to claim 1.

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

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