Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same

Abstract

The present invention relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By including a specific combination of compounds according to the present invention as a plurality of host materials, or by including a compound according to the present invention, an organic electroluminescent device with improved driving voltage, luminous efficiency, and / or lifespan characteristics compared to a conventional organic electroluminescent device can be provided.

Description

Technology Field

[0001] The present invention relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Background Technology

[0002] Since Tang et al. of Eastman Kodak first developed a TPD / Alq3 double-layer small molecule green organic light-emitting diode (OLED) consisting of a light-emitting layer and a charge-transfer layer in 1987, research on organic light-emitting diodes has progressed rapidly and has now reached commercialization. To realize full-color OLED displays, three types of light-emitting materials (RGB) are used. To improve the overall characteristics of the organic light-emitting diode, including resolution, the development of RGB light-emitting materials with high luminous efficiency, driving voltage, and / or long lifespan, as well as the development of OLEDs with these characteristics, are recognized as important tasks.

[0003] Various materials or concepts have been proposed for the organic layers of organic electroluminescent devices to improve luminous efficiency, driving voltage, and / or lifespan, but they have not been satisfactory for practical use. Accordingly, there is a continuous demand to develop organic electroluminescent devices with improved performance compared to previously disclosed organic electroluminescent devices, such as improved driving voltage, luminous efficiency, power efficiency, and / or lifespan characteristics. Prior art literature

[0004] Korean Patent Publication No. 10-2009-0111915 (Published Oct. 28, 2009) International Publication No. 2023 / 022233 (Published Feb. 23, 2023) International Publication No. 2018 / 146962 (Published Aug. 16, 2018) The problem to be solved

[0005] The purpose of this invention is to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and / or lifespan characteristics. means of solving the problem

[0006] As a result of diligent research to solve the above technical problem, the inventors have discovered that an organic electroluminescent device has an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode, wherein the first light-emitting layer contains a first compound represented by the following chemical formula 1 or the following chemical formula 3 as a first host material, and the second light-emitting layer contains a second compound represented by the following chemical formula 2 as a second host material, and the first light-emitting layer and the second light-emitting layer are in direct contact, thereby achieving the above-described objective, and thus completed the present invention.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] R1 to R 16 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0011] However, R1 to R 16 At least one of them is -(L)a-(Ar)b and;

[0012] L is each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0013] Ar is each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0014] a is an integer from 1 to 4, and b is an integer from 1 to 4; each L and Ar may be the same or different from each other;

[0015] [Chemical Formula 3]

[0016]

[0017] In the above chemical formula 3,

[0018] R 50 to R 61 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0019] However, R 50 to R 61 At least one of them is -L 30 -Ar 30 And;

[0020] L 30is a single-bonded, substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0021] Ar 30 is the following chemical formula B-1 or chemical formula B-2, and

[0022] [Chemical Formula B-1]

[0023]

[0024] [Chemical Formula B-2]

[0025]

[0026] R 62 to R 71 One of them is L 30 Connected to;

[0027] R 62 to R 71 are independently, L 30 Connected to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0028] R 67 and R 68 They are connected to each other -O-, -S-, -NR 80 - or -CR 81 R 82 - can form;

[0029] R 80 , R 81 and R 82 is each independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; R 81 and R 82 They can be connected to each other to form a ring,

[0030] Ar1 and Ar2 are each independently hydrogen, deuterium, or substituted or unsubstituted (C6-C30)aryl, provided that Ar1 and Ar2 are not both hydrogen;

[0031] R 100 to R 104 Each is independently hydrogen or deuterium;

[0032] [Chemical Formula 2]

[0033]

[0034] In the above chemical formula 2,

[0035] Ar A is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or the following chemical formula A-1;

[0036] [Chemical Formula A-1]

[0037]

[0038] T1 is O, S, CR a R b or NR c And;

[0039] Ring A and Ring B are each independently a substituted or unsubstituted (C6-C30)arene ring, or a substituted or unsubstituted (3-30)heteroarene ring;

[0040] Ar 11is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0041] R 17 to R 24 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) and;

[0042] R 25 and R 26 are independently, L 12or at the linkage position with, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) and;

[0043] R a and R b Each can be independently a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, or can be connected to form a ring;

[0044] R c is a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;

[0045] L 11 to L 13 Each is independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0046] Ar 13 and Ar 14Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted fused ring of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30), substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted It is a (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted tri(C6-C30)arylsilyl.

[0047] In addition, to achieve the above-mentioned purpose, the inventors provide an organic electroluminescent compound represented by the following chemical formula 11 and comprising at least one deuterium, an organic electroluminescent compound represented by the following chemical formula 12, an organic electroluminescent compound represented by the following chemical formula 13, an organic electroluminescent compound represented by the following chemical formula 31, and an organic electroluminescent compound represented by the following chemical formulas 1-5.

[0048] [Chemical Formula 11]

[0049]

[0050] In the above chemical formula 11,

[0051] R1 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0052] However, R1 to R 16 At least one of them is -(L)a-(Ar)b and;

[0053] L is each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0054] Ar is each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;

[0055] a is an integer from 1 to 4, and b is an integer from 1 to 4; each L and Ar may be the same or different from each other.

[0056] [Chemical Formula 12]

[0057]

[0058] In the above chemical formula 12,

[0059] R1 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0060] However, R1 to R 16 At least one of them is represented by the following chemical formula 12-1;

[0061] [Chemical Formula 12-1]

[0062]

[0063] X is O, S, CR 44 R 45 or NR 46 And;

[0064] L1 is a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene, and L1 is R 36 to R 46 Connected to one of them;

[0065] R 36 to R 46 is a linkage position with L1, or independently, hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl.

[0066] [Chemical Formula 13]

[0067]

[0068] In the above chemical formula 13,

[0069] R 50 to R 61 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0070] However, R 50 to R 61 At least one of them is -L 30 -Ar 30 And;

[0071] L 30 is a single-bonded, substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0072] Ar 30 is the following chemical formula B-1, and

[0073] [Chemical Formula B-1]

[0074]

[0075] R 62 to R 71 One of them is L 30 Connected to;

[0076] R 62 to R 71 are independently, L 30 Connected to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0077] R 67 and R 68 They are connected to each other -O-, -S-, -NR 80 - or -CR 81 R 82 - can form;

[0078] R 80 , R 81 and R 82 is each independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; R 81 and R 82 They can be connected to each other to form a ring.

[0079] [Chemical Formula 31]

[0080]

[0081] In the above chemical formula 31,

[0082] R51 to R 61 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0083] Ar1 and Ar2 are each independently hydrogen, deuterium, or substituted or unsubstituted (C6-C30)aryl, provided that Ar1 and Ar2 are not both hydrogen;

[0084] R 100 to R 104 Each is independently hydrogen or deuterium.

[0085] [Chemical Formula 1-5]

[0086]

[0087] In the above chemical formula 1-5,

[0088] R1 to R5, and R7 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

[0089] L is a single bond;

[0090] Ar is a substituted or unsubstituted phenanthrenyl group;

[0091] The hydrogen in the above chemical formula can be replaced with deuterium. Effects of the invention

[0092] By using a plurality of host materials comprising an organic electroluminescent compound according to the present invention or an organic electroluminescent compound according to the present invention, it is possible to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and / or lifetime characteristics. Specific details for implementing the invention

[0093] The present invention is described in more detail below, but this is for illustrative purposes only and should not be interpreted as limiting the scope of the present invention.

[0094] In the present invention, "organic electroluminescent compound" refers to a compound that can be used in an organic electroluminescent device and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. The hole transport band material may be one or more selected from the group consisting of a hole transport material, a hole injection material, an electron blocking material, a hole assist material, and a light-emitting assist material.

[0095] In the present invention, "multiple types of host materials" refers to a host material comprising a combination of two or more compounds that may be included in any light-emitting layer constituting an organic electroluminescent device, and may refer to both the material before (e.g., before deposition) and after (e.g., after deposition) inclusion in the organic electroluminescent device. For example, the multiple types of host materials of the present invention are a combination of two or more host materials, and may optionally additionally include a conventional material included in the organic electroluminescent material. The two or more compounds included in the multiple types of host materials of the present invention may be included together in a single light-emitting layer or each may be included in different light-emitting layers. For example, the two or more host materials may be mixed-deposited or co-deposited, or deposited individually.

[0096] In this invention, "(C1-C30)alkyl" refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain. According to one embodiment of the present invention, the number of carbon atoms constituting the chain may be 1 to 20, and according to another embodiment, may be 1 to 10. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec Examples include butyl.

[0097] In this invention, "(C6-C30)aryl," "(C6-C30)arylene," or "(C6-C30)arene" refers to a single-ring or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, which may be partially saturated. According to one embodiment of the present invention, the number of carbon atoms in the ring skeleton may be 6 to 20, and according to another embodiment of the present invention, it may be 6 to 15. The aryl includes those having a spiro structure. Specific examples of the above aryls include phenyl, biphenyl, terphenyl, quaternphenyl, naphthyl, non-naphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzoflurenyl, diphenylbenzoflurenyl, dibenzoflurenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthrenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzoflurenthenyl, tolyl, xylyl, mesityl, coumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluren]yl, azulenyl, Examples include tetramethyl-dihydrophenanthrenyl. More specifically, examples of the above aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesithyl, o-coumenyl, m-coumenyl, p-coumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaternphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-Diphenyl-3-fluorenyl, 9,9-Diphenyl-4-fluorenyl, 1-Anthryl, 2-Anthryl, 9-Anthryl, 1-Phenanthryl, 2-Phenanthryl, 3-Phenanthryl, 4-Phenanthryl, 9-Phenanthryl, 1-Crysenyl, 2-Crysenyl, 3-Crysenyl, 4-Crysenyl, 5-Crysenyl, 6-Crysenyl, Benzo[c]Phenanthryl, Benzo[g]Crysenyl, 1-Triphenyllenyl, 2-Triphenyllenyl, 3-Triphenyllenyl, 4-Triphenyllenyl, 3-Fluoranthenyl, 4-Fluoranthenyl, 8-Fluoranthenyl, 9-Fluoranthenyl, Benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl,11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, Examples include 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc.

[0098] In this invention, “(3-30-membered)heteroaryl,” “(3-30-membered)heteroarylene,” or “(3-30-membered)heteroarylene” refers to an aryl group or arylene group having 3 to 30 ring skeleton atoms and containing one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. Additionally, in this invention, the heteroaryl or heteroarylene includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl(len) group by a single bond, and also includes having a spiro structure. Examples of the above heteroaryls include single-cyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzonaphthofuranyl, benzophenanthrofuranyl, dibenzothiophenyl, benzonaphthiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzophenanthrothiophenyl, benzisoxazolyl, benzoxazolyl, phenanthrooxazolyl, phenanthrothiazolyl, There are fused cyclic heteroaryls such as isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naftiridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, examples of the above heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl,1-Indolidedinyl, 2-Indolidedinyl, 3-Indolidedinyl, 5-Indolidedinyl, 6-Indolidedinyl, 7-Indolidedinyl, 8-Indolidedinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 3-Pyridinyl, 4-Pyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furyl, 3-Furyl, 2-Benzofuranil, 3-Benzofuranil, 4-Benzofuranil, 5-Benzofuranil, 6-Benzofuranil, 7-Benzofuranil, 1-Isobenzofuranil, 3-Isobenzofuranil, 4-Isobenzofuranil, 5-Isobenzofuranil, 6-Isobenzofuranil, 7-Isobenzofuranil, 2-Quinolyl, 3-Quinolyl, 4-Quinolyl, 5-Quinolyl, 6-Quinolyl, 7-Quinolyl, 8-Quinolyl, 1-Isoquinolyl, 3-Isoquinolyl, 4-Isoquinolyl, 5-Isoquinolyl, 6-Isoquinolyl, 7-Isoquinolyl, 8-Isoquinolyl, 2-Quinoxalinyl, 5-Quinoxalinyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl, Azacarbazolyl-9-yl, 1-Phenantridinyl, 2-Phenantridinyl, 3-Phenantridinyl, 4-Phenantridinyl, 6-Phenantridinyl, 7-Phenantridinyl, 8-Phenanthridinyl, 9-Phenanthridinyl, 10-Phenanthridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrole-1-yl, 2-Methylpyrrole-3-yl, 2-Methylpyrrole-4-yl, 2-Methylpyrrole-5-yl, 3-Methylpyrrole-1-yl, 3-Methylpyrrole-2-yl, 3-Methylpyrrole-4-yl, 3-Methylpyrrole-5-yl, 2-, tert-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-Naphtho-[1,2-b]-Benzofuranyl, 9-Naphtho-[1,2-b]-Benzofuranyl, 10-Naphtho-[1,2-b]-Benzofuranyl, 1-Naphtho-[2,3-b]-Benzofuranyl, 2-Naphtho-[2,3-b]-Benzofuranyl, 3-Naphtho-[2,3-b]-Benzofuranyl, 4-Naphtho-[2,3-b]-Benzofuranyl, 5-Naphtho-[2,3-b]-Benzofuranyl, 6-Naphtho-[2,3-b]-Benzofuranyl, 7-Naphtho-[2,3-b]-Benzofuranyl, 8-Naphtho-[2,3-b]-Benzofuranyl, 9-Naphtho-[2,3-b]-Benzofuranyl, 10-Naphtho-[2,3-b]-Benzofuranyl, 1-Naphtho-[2,1-b]-Benzofuranyl, 2-Naphtho-[2,1-b]-Benzofuranyl, 3-Naphtho-[2,1-b]-Benzofuranyl, 4-Naphtho-[2,1-b]-Benzofuranyl, 5-Naphtho-[2,1-b]-Benzofuranyl, 6-Naphtho-[2,1-b]-Benzofuranyl, 7-Naphtho-[2,1-b]-Benzofuranyl, 8-Naphtho-[2,1-b]-Benzofuranyl, 9-Naphtho-[2,1-b]-Benzofuranyl, 10-Naphtho-[2,1-b]-Benzofuranyl, 1-Naphtho-[1,2-b]-Benzothiophenyl, 2-Naphtho-[1,2-b]-Benzothiophenyl, 3-Naphtho-[1,2-b]-Benzothiophenyl, 4-Naphtho-[1,2-b]-Benzothiophenyl, 5-Naphtho-[1,2-b]-Benzothiophenyl, 6-Naphtho-[1,2-b]-Benzothiophenyl, 7-Naphtho-[1,2-b]-Benzothiophenyl, 8-Naphtho-[1,2-b]-Benzothiophenyl, 9-Naphtho-[1,2-b]-Benzothiophenyl, 10-Naphtho-[1,2-b]-Benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl,3-Naphtho-[2,3-b]-benzothiophenyl, 4-Naphtho-[2,3-b]-benzothiophenyl, 5-Naphtho-[2,3-b]-benzothiophenyl, 1-Naphtho-[2,1-b]-benzothiophenyl, 2-Naphtho-[2,1-b]-benzothiophenyl, 3-Naphtho-[2,1-b]-benzothiophenyl, 4-Naphtho-[2,1-b]-benzothiophenyl, 5-Naphtho-[2,1-b]-benzothiophenyl, 6-Naphtho-[2,1-b]-benzothiophenyl, 7-Naphtho-[2,1-b]-benzothiophenyl, 8-Naphtho-[2,1-b]-benzothiophenyl, 9-Naphtho-[2,1-b]-Benzothiophenyl, 10-Naphtho-[2,1-b]-Benzothiophenyl, 2-Benzofuro[3,2-d]Pyrimidinyl, 6-Benzofuro[3,2-d]Pyrimidinyl, 7-Benzofuro[3,2-d]Pyrimidinyl, 8-Benzofuro[3,2-d]Pyrimidinyl, 9-Benzofuro[3,2-d]Pyrimidinyl, 2-Benzothio[3,2-d]Pyrimidinyl, 6-Benzothio[3,2-d]Pyrimidinyl, 7-Benzothio[3,2-d]Pyrimidinyl, 8-Benzothio[3,2-d]Pyrimidinyl, 9-Benzothio[3,2-d]Pyrimidinyl, 2-Benzofuro[3,2-d]pyrazinyl, 6-Benzofuro[3,2-d]pyrazinyl, 7-Benzofuro[3,2-d]pyrazinyl, 8-Benzofuro[3,2-d]pyrazinyl, 9-Benzofuro[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzothio[3,2-d]pyrazinyl, 8-Benzothio[3,2-d]pyrazinyl, 9-Benzothio[3,2-d]pyrazinyl, 1-Silafluorenyl, 2-Silafluorenyl, 3-Silafluorenyl, 4-Silafluorenyl, 1-Germafluorenyl, Examples include 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenphenyl, 2-dibenzoselenphenyl, 3-dibenzoselenphenyl, 4-dibenzoselenphenyl, etc.

[0099] In the present invention, "(C3-C30)cycloalkyl" refers to a single-ring or polycyclic hydrocarbon having 3 to 30 carbon atoms in its ring skeleton. According to one embodiment of the present invention, the number of carbon atoms in the ring skeleton may be 3 to 20, and according to another embodiment, it may be 3 to 7. Specific examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc.

[0100] In the present invention, "(3-7)heterocycloalkyl" refers to a cycloalkyl having 3 to 7 ring skeleton atoms and containing one or more heteroatoms. The number of ring skeleton atoms may be, for example, 5 to 7. According to one embodiment of the present invention, the heteroatoms may be one or more selected from the group consisting of B, N, O, S, Si, and P, and according to another embodiment, one or more selected from the group consisting of O, S, and N. Specific examples of the heterocycloalkyl include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.

[0101] In this invention, "a fused ring of (C3-C30) aliphatic rings and (C6-C30) aromatic rings" refers to a functional group of a ring in which one or more aliphatic rings having 3 to 30 carbon atoms in the ring skeleton are fused with one or more aromatic rings having 6 to 30 carbon atoms in the ring skeleton. According to one embodiment of the present invention, the (C3-C30) aliphatic rings may have 3 to 25 carbon atoms in the ring skeleton, and according to another embodiment, may have 3 to 18 carbon atoms in the ring skeleton. According to one embodiment of the present invention, the (C6-C30) aromatic rings may have 6 to 25 carbon atoms in the ring skeleton, and according to another embodiment of the present invention, may have 6 to 18 carbon atoms in the ring skeleton. Specific examples of the above-mentioned fused ring include a fused ring of one or more benzenes and one or more cyclohexanes, or a fused ring of one or more naphthalenes and one or more cyclopentanes. In the present invention, the carbon atoms of the fused ring of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring may be replaced with one or more heteroatoms selected from B, N, O, S, Si, and P, for example, with one or more heteroatoms selected from N, O, and S.

[0102] In this document, "halogen" includes F, Cl, Br, and I atoms.

[0103] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other; for example, in a benzene substituent, when the substituents are at the 1,2 position, it is called the ortho position. Meta indicates that two substituents are at the 1,3 position; for example, in a benzene substituent, when the substituents are at the 1,3 position, it is called the meta position. Para indicates that two substituents are at the 1,4 position; for example, in a benzene substituent, when the substituents are at the 1,4 position, it is called the para position.

[0104] In this invention, "a ring formed by connecting adjacent substituents" means a substituted or unsubstituted (3-30) single-ring or polycyclic ring of alicyclic, aromatic, or a combination thereof formed by connecting or fusing two or more adjacent substituents. The ring may be, for example, a substituted or unsubstituted (5-25) single-ring or polycyclic ring of alicyclic, aromatic, or a combination thereof. According to one embodiment of the invention, the number of ring skeleton atoms of the ring may be (5-20) and according to another embodiment, may be (5-15). Additionally, the ring may include one or more heteroatoms selected from B, N, O, S, Si, and P, for example, one or more heteroatoms selected from N, O, and S. Specific examples of the above ring may be in the form of a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofuren ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring or a substituted or unsubstituted carbazole ring, etc.

[0105] In the description of "substituted or non-substituted" in the present invention, "substituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent), and includes substitution by a group in which two or more substituents are connected. For example, "a substituent in which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as a single heteroaryl substituent or as two heteroaryl substituents connected.

[0106] In the present invention, the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the fused ring group of the substituted aliphatic ring and aromatic ring are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide group; (C1-C30)alkyl substituted or unsubstituted with deuterium; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)aryltio; (3-30)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl; (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, (C1-C30)alkyl, (C6-C30)aryl and (3-30)heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; Mono- or di- (C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino; mono- or di- (3-30)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3-30)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3-30)heteroarylamino; (C6-C30)aryl(3-30)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; Di(C6-C30)arylboronyl; (C6-C30)arylphosphine group; Di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl;It may be one or more selected from the group consisting of (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

[0107] In this document, “combinations thereof” refers to a combination of one or more components from the applicable list to form a known or chemically stable arrangement that a person skilled in the art can conceive from the applicable list. For example, alkyl and deuterium may be combined to form a partially or wholly deuteriumated alkyl group; halogen and alkyl may be combined to form a halogenated alkyl substituent; and halogen, alkyl, and aryl may be combined to form a halogenated arylalkyl. For example, a preferred combination of substituents may comprise up to 50 atoms that are not hydrogen or deuterium, or up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium, or in many cases, a preferred combination of substituents may comprise up to 20 atoms that are not hydrogen or deuterium.

[0108] In the present invention, if substituents are not indicated in the chemical formula or compound structure, it may mean that all positions where substituents can be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope of deuterium, and in this case, the deuterium content may be 0% to 100%. In the present invention, where substituents are not indicated in the chemical formula or compound structure, if the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen or deuterium, and deuterium is not explicitly excluded, hydrogen and deuterium may be used in a mixture in the compound. The above deuterium is one of the isotopes of hydrogen, an element having a deuteron as its nucleus, consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol may be written as D or 2H. The above isotopes, which refer to atoms that have the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0109] Hereinafter, an organic electroluminescent device comprising a plurality of host materials according to the present invention will be described in detail.

[0110] An organic electroluminescent device according to the present invention has an anode, a cathode, a first emitting layer disposed between the anode and the cathode, and a second emitting layer disposed between the first emitting layer and the cathode. The first emitting layer contains a first compound represented by the following chemical formula 1 or the following chemical formula 3 as a first host material.

[0111] [Chemical Formula 1]

[0112]

[0113] In the above Chemical Formula 1, R1 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted A tri(C6-C30)arylsilyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, provided that in the above chemical formula 1, R1 to R 16 At least one of them is -(L)a-(Ar)b, and preferably, R1 to R 16 Two of them may be -(L)a-(Ar)b.

[0114] According to one aspect of the present invention, R1 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3-7)heterocycloalkyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R1 to R 16 Each may independently be hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C20)aryl, or substituted or unsubstituted (3-20)heteroaryl. For example, R1 to R 16Each may independently be hydrogen, deuterium, naphthyl-substituted or unsubstituted phenyl, biphenyl, phenyl or naphthyl-substituted or unsubstituted naphthyl, phenyl-substituted or unsubstituted phenanthrenyl, unsubstituted (15-membered) heteroaryl, triphenylenyl, phenyl-substituted or unsubstituted anthracenyl, o-terphenyl, m-terphenyl, p-terphenyl, phenyl-substituted or unsubstituted 2,3-benzophenanthrenyl, dimethylfluorenyl, dimethyl 2,3-benzophenyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[1,2-d]furanyl, phenanthro[4,5-bcd]furanyl, dibenzofuranyl, dibenzothiophenyl, or phenyl-substituted or unsubstituted carbazolyl, and these may be further substituted with deuterium. provided that R1 to R 16 At least one of them is -(L)a-(Ar)b, and preferably, R1 to R 16 Two of them may be substituted with -(L)a-(Ar)b.

[0115] According to one embodiment of the present invention, the above chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0116] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0117]

[0118] [Chemical Formula 1-3] [Chemical Formula 1-4]

[0119]

[0120] In the above formula 1, L is each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene. According to one embodiment of the present invention, L may be a single-bonded, substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3-25)heteroarylene. According to another embodiment of the present invention, L may be a single-bonded, substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (3-20)heteroarylene. For example, L may be a single-bonded, phenylene, biphenylene, naphthylene, phenanthrenylene, anthracenylene, 2,3-benzophenanthrenylene, or carbazolilene, which may be further substituted with deuterium.

[0121] In the above chemical formula 1, Ar is each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl. According to one embodiment of the present invention, Ar may each independently be a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (3-25)heteroaryl. According to another embodiment of the present invention, Ar may each independently be a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (3-20)heteroaryl. For example, Ar may each independently be hydrogen, deuterium, naphthyl-substituted or unsubstituted phenyl, biphenyl, phenyl or naphthyl-substituted or unsubstituted naphthyl, phenyl-substituted or unsubstituted phenanthrenyl, unsubstituted (15-membered) heteroaryl, triphenylenyl, phenyl-substituted or unsubstituted anthracenyl, o-terphenyl, m-terphenyl, p-terphenyl, phenyl-substituted or unsubstituted 2,3-benzophenanthrenyl, dimethylfluorenyl, dimethyl 2,3-benzophenyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[1,2-d]furanyl, phenanthro[4,5-bcd]furanyl, dibenzofuranyl, dibenzothiophenyl, or phenyl-substituted or unsubstituted carbazolyl, which may be further substituted with deuterium.

[0122] Here, each L and Ar may be the same or different from each other.

[0123] In the above chemical formula 1, a is an integer from 1 to 4 and b may be an integer from 1 to 4, preferably a is an integer from 1 to 2 and b may be an integer from 1 to 2.

[0124] [Chemical Formula 3]

[0125]

[0126] In the above chemical formula 3, R 50 to R 61 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one aspect of the present invention, R 50 to R 61 Each may independently be hydrogen, deuterium, halogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R 50 to R 61Each may independently be hydrogen, deuterium, halogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (3-20)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C20) aromatic ring. According to another aspect of the present invention, R 50 to R 61 It is preferable that each be hydrogen or deuterium independently. For example, R 50 to R 61 Each may independently be hydrogen; deuterium; phenyl substituted or unsubstituted with fluoro, naphthyl, phenanthrenyl, phenantro[4,5-bcd]furanyl, or phenantro[4,5-bcd]thiophenyl; biphenyl; phenyl substituted or unsubstituted with naphthyl, biphenyl, naphthyl substituted or unsubstituted with phenyl, phenanthrenyl, triphenylenyl, naphthyl substituted or unsubstituted with terphenyl; phenanthrenyl substituted or unsubstituted with deuterium or phenyl; dimethyl 4,5-methylenephenanthrenyl; phenantro[4,5-bcd]furanyl substituted or unsubstituted with deuterium or phenyl; phenantro[4,5-bcd]thiophenyl substituted or unsubstituted with phenyl; or phenantro[4,5-bcd]carbazolyl substituted with phenyl, and these may be further substituted with deuterium.

[0127] However, in the above Chemical Formula 3, R 50 to R 61 At least one of them is -L 30 -Ar 30 and, preferably, R 50 This -L 30 -Ar 30 It could be.

[0128] L 30 is a single-bonded, substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-30)heteroarylene. According to one aspect of the present invention, L 30 It may be a single-bonded, substituted, or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-20)heteroarylene. For example, L30 The phenylene, biphenylene, naphthylene, phenantro[4,5-bcd]furanilene, phenantro[4,5-bcd]thiophenylene, or phenantro[4,5-bcd]carbazolilene may be single-bonded, fluoro-substituted, or unsubstituted, and these may be further substituted with deuterium.

[0129] Ar 30 is the following chemical formula B-1 or B-2.

[0130] [Chemical Formula B-1] [Chemical Formula B-2]

[0131]

[0132] In the above chemical formula B-1, R 62 to R 71 One of them is L 30 It is connected to.

[0133] In the above chemical formula B-1, R 62 to R 71 are independently, L 30 Connected to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one aspect of the present invention, R 62 to R71 are independently, L 30 It may be connected to, hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R 62 to R 71 are independently, L 30 It may be connected to, hydrogen, deuterium, substituted or unsubstituted (C6-C20)aryl, or a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C20) aromatic ring. For example, R 62 to R 71 are independently, L 30 It may be connected to, hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium.

[0134] In the above chemical formula B-1, R 67 and R 68 They are connected to each other -O-, -S-, -NR 80 - or -CR 81 R 82 - can form

[0135] In the above chemical formula B-1, R 80 , R 81 and R 82 is each independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; R 81 and R 82 They can be connected to each other to form a ring. According to one embodiment of the present invention, R 80 , R 81 and R 82Each may independently be a substituted or unsubstituted (C1-C20)alkyl, or a substituted or unsubstituted (C6-C20)aryl. For example, R 80 , R 81 and R 82 Each can be independently methyl or phenyl.

[0136] In the above chemical formula B-2, Ar1 and Ar2 are each independently hydrogen, deuterium, or a substituted or unsubstituted (C6-C30)aryl, provided that Ar1 and Ar2 are not both hydrogen.

[0137] In the above chemical formula B-2, R 100 to R 104 Each is independently hydrogen or deuterium.

[0138] The second light-emitting layer above contains a second compound represented by the following chemical formula 2 as a second host material.

[0139] [Chemical Formula 2]

[0140]

[0141] In the above chemical formula 2, Ar 11 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl. According to one aspect of the present invention, Ar 11 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (13-30)heteroaryl. According to another aspect of the present invention, Ar 11 is a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (13-25)heteroaryl. For example, Ar 11phenyl substituted or unsubstituted with naphthyl; naphthyl substituted or unsubstituted with phenyl, naphthyl, or biphenyl; biphenyl substituted or unsubstituted with naphthyl; o-terphenyl substituted or unsubstituted with phenyl; m-terphenyl; p-terphenyl; dimethylfluorenyl; diphenylfluorenyl; phenanthrenyl substituted or unsubstituted with phenyl; carbazolyl substituted or unsubstituted with phenyl; 1,2-benzocarbazolyl; 2,3-benzocarbazolyl; 3,4-benzocarbazolyl; dibenzofuranyl; dibenzothiophenyl; benzo[b]naphtho[2,3-d]furanyl; benzo[b]naphtho[2,3-d]thiophenyl; dimethyl 2,3-benzoflurenyl; dimethyl 3,4-benzoflurenyl; spirobifluorenyl; Or it may be triphenylenyl, and these may be further substituted with deuterium.

[0142] In the above chemical formula 2, R 17 to R 24 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) is. According to one aspect of the present invention, R 17 to R 24Each is independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 It can be. For example, R 17 to R 24 Each can be hydrogen or deuterium independently.

[0143] In the above chemical formula 2, Ar A It may be a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or the following chemical formula A-1.

[0144] [Chemical Formula A-1]

[0145]

[0146] According to one embodiment of the present invention, in the above chemical formula 2, Ar A may be a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (3-25)heteroaryl, or the above formula A-1. According to another aspect of the present invention, the Ar A may be a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (3-20)heteroaryl, or the above formula A-1. For example, Ar A ε₀ may be phenyl substituted or unsubstituted with naphthyl or phenanthrenyl; naphthyl substituted or unsubstituted with phenyl, biphenyl, or naphthyl; biphenyl substituted or unsubstituted with naphthyl; phenanthrenyl substituted or unsubstituted with phenyl; o-terphenyl; m-terphenyl; p-terphenyl; phenantro[4,5-bcd]furanyl; 2,3-diphenyl-1,2-dihydronaphthyl; or formula A-1, which may be further substituted with deuterium.

[0147] In the above chemical formula A-1, T1 is O, S, CRa R b or NR c is. For example, T1 is O, S, or CR a R b It could be.

[0148] In the above formula A-1, the A ring and the B ring are each independently a substituted or unsubstituted (C6-C30) arene ring or a substituted or unsubstituted (3-30) heteroarene ring. According to one embodiment of the present invention, the A ring and the B ring may each independently be a substituted or unsubstituted (C6-C25) arene. According to another embodiment of the present invention, the A ring and the B ring may each independently be a substituted or unsubstituted (C6-C18) arene. For example, the A ring and the B ring may each independently be a substituted or unsubstituted benzene ring or a naphthalene ring, and their substituents may be one or more selected from the group consisting of deuterium, phenyl, naphthyl, biphenyl, and combinations thereof.

[0149] In the above chemical formula A-1, R 25 and R 26 are independently, L 12or at the linkage position with, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) is. According to one aspect of the present invention, R 25 and R 26 are independently, L 12 It may be a linkage position with, or hydrogen, deuterium, or a substituted or unsubstituted (C6-C25)aryl. According to another aspect of the present invention, R 25 and R 26 are independently, L 12 It may be a linkage position with, or a (C6-C18)aryl substituted or unsubstituted with hydrogen, deuterium, or deuterium. For example, R 25 and R 26 are independently, L 12 It may be a linkage position with, or hydrogen, deuterium, phenyl, naphthyl, or biphenyl, etc., and these may be further substituted with deuterium.

[0150] The above R a and R bEach may independently be a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl, or may be connected to form a ring. According to one embodiment of the present invention, R a and R b Each may independently be a substituted or unsubstituted (C1-C20)alkyl. According to another aspect of the present invention, R a and R b Each can independently be a substituted or unsubstituted (C1-C10)alkyl. For example, R a and R b Each may independently be a deuterium-substituted or unsubstituted methyl.

[0151] The above R c is a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl. According to one embodiment of the present invention, R c It may be a substituted or unsubstituted (C1-C20)alkyl, or a substituted or unsubstituted (C6-C20)aryl.

[0152] The above L 11 to L 13 Each is independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene. According to one aspect of the present invention, L 11 to L 13 Each may independently be a single-bonded, substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5-25)heteroarylene. According to another aspect of the present invention, L 11 to L 13 Each may independently be a single-bonded, substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5-20)heteroarylene. For example, L 11 to L 13Each can be independently a single bond, phenylene, naphthylene, biphenylene, or phenanthrenylene, and these can be further substituted with deuterium.

[0153] The above Ar 13 and Ar 14 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted fused ring of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30), substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted It is a (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted tri(C6-C30)arylsilyl.

[0154] Meanwhile, the first light-emitting layer and the second light-emitting layer are in direct contact.

[0155] According to one aspect of the present invention, the above Ar 11 and Ar A Each may be independently selected from the group consisting of deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted phenanthrenyl, or combinations thereof. According to another aspect of the present invention, the Ar 11is selected from the group consisting of deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted phenanthrenyl, or combinations thereof, and Ar A It may be dibenzofuranyl substituted or unsubstituted with deuterium, or dibenzothiophenyl substituted or unsubstituted with deuterium.

[0156] According to one aspect of the present invention, the above Ar A It may be represented by the following chemical formula b-1.

[0157] [Chemical formula b-1]

[0158]

[0159] In the above chemical formula b-1, R 27 to R 32 are independently, L 12 or at the linkage position with, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) or adjacent substituents can be connected to each other to form a ring. According to another aspect of the present invention, R 27to R 32 are independently, L 12 It may be a linkage position with, hydrogen, deuterium, substituted or unsubstituted (C6-C25)aryl, or adjacent substituents connected to each other to form a ring. According to another aspect of the present invention, R 27 to R 32 are independently, L 12 It can be a linkage position with, hydrogen, deuterium, or a substituted or unsubstituted (C6-C18)aryl, or adjacent substituents can be connected to form a substituted or unsubstituted (3-20) single or polycyclic aromatic ring. For example, R 27 to R 32 are independently, L 12 It may be a connecting position with, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted naphthyl, or adjacent substituents connected to each other to form a deuterium-substituted or unsubstituted benzene ring.

[0160] The above T1, R 25 , R 26 , L 13 , Ar 13 and Ar 14 Each is identical to the definition in Chemical Formula 2 above.

[0161] According to one embodiment of the present invention, the above chemical formula 2 may be represented by the following chemical formula 2-1 or 2-2.

[0162] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0163]

[0164] In the above chemical formulas 2-1 and 2-2, R 27 to R 32Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Tri(C6-C30)arylsilyl, a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14 ) or adjacent substituents can be connected to each other to form a ring.

[0165] In the above chemical formulas 2-1 and 2-2, R 33 to R 35 are independently, L 12 It is a linkage position with, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted (C3-C30)alipsilyl, a fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L 13 -N(Ar 13 )(Ar 14) or adjacent substituents can be connected to each other to form a ring. According to one aspect of the present invention, R 33 to R 35 are independently, L 12 It may be a linkage position with, hydrogen, deuterium, substituted or unsubstituted (C6-C25)aryl, or adjacent substituents connected to each other to form a ring. According to another aspect of the present invention, R 33 to R 35 are independently, L 12 It can be a linkage position with, hydrogen, deuterium, or substituted or unsubstituted (C6-C18)aryl, or adjacent substituents connected to each other to form a substituted or unsubstituted (3-20) single or polycyclic aromatic ring. For example, R 33 to R 35 are independently, L 12 It may be a connecting position with, deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted naphthyl, or adjacent substituents connected to each other to form a deuterium-substituted or unsubstituted benzene ring.

[0166] T1, R 17 to R 26 , L 11 to L 13 , Ar 11 , Ar 13 , and Ar 14 is the same as the definition in Chemical Formula 2 above.

[0167] According to one embodiment of the present invention, at least one of the above formulas 1 and 2 may have a compound containing deuterium.

[0168] The compound represented by the above chemical formula 1 may be more specifically one or more selected from the following compounds, but is not limited thereto.

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 1, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 1 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0226] According to one embodiment of the present invention, the compound represented by the above formula 2 may be one or more selected from the following compounds, but is not limited thereto.

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 2, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 2 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0375] According to one embodiment of the present invention, the compound represented by the above chemical formula 3 may be one or more selected from the following compounds, but is not limited thereto.

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 3, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 3 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteriumization, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0423] The compound represented by Formula 1 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 1 of the present invention may be prepared by referring to Reaction Scheme 1 below, but is not limited thereto.

[0424] [Reaction Equation 1]

[0425]

[0426] In the above reaction scheme 1, R1 to R 16 , L, Ar, a and b are the same as their definitions in Chemical Formula 1.

[0427] The compound represented by Formula 2 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 2 of the present invention may be prepared by referring to Reaction Scheme 2 below, but is not limited thereto.

[0428] [Reaction Equation 2]

[0429]

[0430] In the above reaction scheme 2, Ar A , Ar 11 , R17 to R 24 , L 11 and L 12 is the same as the definition in Chemical Formula 2.

[0431] The compound represented by Formula 3 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 3 of the present invention may be prepared by referring to Reaction Scheme 3 below, but is not limited thereto.

[0432] [Reaction Equation 3]

[0433]

[0434] In the above reaction scheme 3, R 50 to R 61 , L 30 and Ar 30 is the same as the definition in Chemical Formula 3.

[0435] Although exemplary synthesis examples of compounds represented by chemical formulas 1, 2, and 3 have been described above, they are all based on Suzuki cross-coupling reaction, Wittig reaction, Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, N-arylation reaction, H-mont-mediated etherification reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphate-mediated reductive cyclization reaction, and it will be easily understood by those skilled in the art that the above reactions proceed even if other substituents defined in chemical formulas 1 to 3 are attached in addition to the substituents specified in the specific synthesis examples.

[0436] An organic electroluminescent compound according to one embodiment of the present invention is represented by the following chemical formula 11 and comprises at least one deuterium.

[0437] [Chemical Formula 11]

[0438]

[0439] In the above chemical formula 11,

[0440] R1 to R 16 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one embodiment of the present invention, R1 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3-7)heterocycloalkyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R1 to R 16Each may independently be hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C20)aryl, or substituted or unsubstituted (3-20)heteroaryl. For example, R1 to R 16 Each may independently be hydrogen, deuterium, naphthyl-substituted or unsubstituted phenyl, biphenyl, phenyl or naphthyl-substituted or unsubstituted naphthyl, phenyl-substituted or unsubstituted phenanthrenyl, unsubstituted (15-membered) heteroaryl, triphenylenyl, phenyl-substituted or unsubstituted anthracenyl, o-terphenyl, m-terphenyl, p-terphenyl, phenyl-substituted or unsubstituted 2,3-benzophenanthrenyl, dimethylfluorenyl, dimethyl 2,3-benzophenyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[1,2-d]furanyl, phenanthro[4,5-bcd]furanyl, dibenzofuranyl, dibenzothiophenyl, or phenyl-substituted or unsubstituted carbazolyl, and these may be further substituted with deuterium.

[0441] However, R1 to R 16 At least one of them is -(L)a-(Ar)b.

[0442] In the above formula 11, L is each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene. According to one embodiment of the present invention, L may be a single-bonded, substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (3-25)heteroarylene. According to another embodiment of the present invention, L may be a single-bonded, substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (3-20)heteroarylene. For example, L may be a single-bonded, phenylene, biphenylene, naphthylene, phenanthrenylene, anthracenylene, 2,3-benzophenanthrenylene, or carbazolilene, which may be further substituted with deuterium.

[0443] In the above chemical formula 11, Ar is each independently a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3-30)heteroaryl. According to one embodiment of the present invention, Ar may each independently be a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (3-25)heteroaryl. According to another embodiment of the present invention, Ar may each independently be a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (3-20)heteroaryl. For example, Ar may each independently be hydrogen, deuterium, naphthyl-substituted or unsubstituted phenyl, biphenyl, phenyl or naphthyl-substituted or unsubstituted naphthyl, phenyl-substituted or unsubstituted phenanthrenyl, unsubstituted (15-membered) heteroaryl, triphenylenyl, phenyl-substituted or unsubstituted anthracenyl, o-terphenyl, m-terphenyl, p-terphenyl, phenyl-substituted or unsubstituted 2,3-benzophenanthrenyl, dimethylfluorenyl, dimethyl 2,3-benzophenyl, benzo[b]naphtho[2,3-d]furanyl, benzo[b]naphtho[1,2-d]furanyl, phenanthro[4,5-bcd]furanyl, dibenzofuranyl, dibenzothiophenyl, or phenyl-substituted or unsubstituted carbazolyl, which may be further substituted with deuterium.

[0444] Here, each L and Ar may be the same or different from each other.

[0445] In the above chemical formula 11, a is an integer from 1 to 4 and b may be an integer from 1 to 4, preferably a is an integer from 1 to 2 and b may be an integer from 1 to 2.

[0446] The residual rate of hydrogen in the above organic electroluminescent compound may be 10 to 20%, preferably 20 to 30%.

[0447] The compound represented by the above chemical formula 11 may be selected from the following compounds, but is not limited to them.

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 11, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 11 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteriumization, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0473] An organic electroluminescent compound according to one embodiment of the present invention is represented by the following chemical formula 12.

[0474] [Chemical Formula 12]

[0475]

[0476] In the above chemical formula 12,

[0477] R1 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one embodiment of the present invention, R1 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3-7)heterocycloalkyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R1 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (3-20)heteroaryl. For example, R1 to R 16 Each can be independently hydrogen, deuterium, phenyl, or an unsubstituted (15-membered) heteroaryl, which can be further substituted with deuterium.

[0478] However, R1 to R 16 At least one of them is represented by the following chemical formula 12-1.

[0479] [Chemical Formula 12-1]

[0480]

[0481] In the above chemical formula 12-1, X is O, S, CR 44 R 45 or NR 46 am.

[0482] In the above formula 12-1, L1 is a single bond, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroaryl. According to one embodiment of the present invention, L1 may be a single bond, substituted or unsubstituted (C6-C20)arylene, or a substituted or unsubstituted (3-20)heteroaryl. For example, L1 may be a single bond.

[0483] In the above chemical formula 12-1, L1 is R 36 to R 46 It can be connected to one of them.

[0484] In the above chemical formula 12-1, R 36 to R 46 is a linking position with L1 or, respectively, is hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl. According to one embodiment of the present invention, R 36 to R 46 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl. According to another aspect of the present invention, R 36 to R 46 Each can independently be hydrogen, deuterium, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (3-20)heteroaryl. For example, R 36 to R 46 Each can be independently hydrogen, deuterium, phenyl, or an unsubstituted (15-membered) heteroaryl.

[0485] The compound represented by the above chemical formula 12 may be selected from the following compounds, but is not limited to them.

[0486]

[0487]

[0488]

[0489] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 12, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 12 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteriumization, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0490] An organic electroluminescent compound according to one embodiment of the present invention is represented by the following chemical formula 13.

[0491] [Chemical Formula 13]

[0492]

[0493] In the above chemical formula 13, R 50 to R 61Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one aspect of the present invention, R 50 to R 61 Each may independently be a hydrogen, a deuterium, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R 50 to R 61 Each may independently be a hydrogen, deuterium, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (3-20)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C20) aromatic ring. For example, R 50 to R 61Each may independently be hydrogen; deuterium; phenyl substituted or unsubstituted with fluoro, naphthyl, phenanthrenyl, phenantro[4,5-bcd]furanyl, or phenantro[4,5-bcd]thiophenyl; biphenyl; naphthyl substituted or unsubstituted with phenanthrenyl; phenanthrenyl substituted or unsubstituted with deuterium or phenyl; dimethyl 4,5-methylenephenanthrenyl; phenantro[4,5-bcd]furanyl substituted or unsubstituted with deuterium or phenyl; phenantro[4,5-bcd]thiophenyl substituted or unsubstituted with phenyl; or phenantro[4,5-bcd]carbazolyl substituted with phenyl, and these may be further substituted with deuterium.

[0494] However, R 50 to R 61 At least one of them is -L 30 -Ar 30 and, preferably, R 50 This -L 30 -Ar 30 It could be.

[0495] L 30 is a single-bonded, substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-30)heteroarylene. According to one aspect of the present invention, L 30 It may be a single-bonded, substituted, or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (3-20)heteroarylene. For example, L 30 The phenylene, biphenylene, naphthylene, phenantro[4,5-bcd]furanilene, phenantro[4,5-bcd]thiophenylene, or phenantro[4,5-bcd]carbazolilene may be single-bonded, fluoro-substituted, or unsubstituted, and these may be further substituted with deuterium.

[0496] Ar 30 is the following chemical formula B-1.

[0497] [Chemical Formula B-1]

[0498]

[0499] In the above chemical formula B-1, R62 to R 71 One of them is L 30 It is connected to.

[0500] In the above chemical formula B-1, R 62 to R 71 are independently, L 30 Connected to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one aspect of the present invention, R 62 to R 71 Each may independently be a hydrogen, a deuterium, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R 62 to R 71 Each can independently be a hydrogen, deuterium, a substituted or unsubstituted (C6-C20)aryl, or a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C20) aromatic ring. For example, R 62 to R 71Each may independently be hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium.

[0501] R 67 and R 68 They are connected to each other -O-, -S-, -NR 80 - or -CR 81 R 82 - can form

[0502] R 80 , R 81 and R 82 is each independently a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; R 81 and R 82 They can be connected to each other to form a ring. According to one embodiment of the present invention, R 80 , R 81 and R 82 Each may independently be a substituted or unsubstituted (C1-C20)alkyl, or a substituted or unsubstituted (C6-C20)aryl. For example, R 80 , R 81 and R 82 Each can be independently methyl or phenyl.

[0503] According to one embodiment of the present invention, the formula B-1 may be represented by the following formula B-1-1 or formula B-1-2.

[0504] [Chemical Formula B-1-1]

[0505]

[0506] [Chemical Formula B-1-2]

[0507]

[0508] In the above chemical formulas B-1-1 and B-1-2, R 62 to R 66 , and R 69 to R71 is the same as the definition in the above chemical formula B-1.

[0509] In the above chemical formulas B-1-1 and B-1-2, R 67 and R 68 are independently, L 30 Connected to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring.

[0510] In the above chemical formulas B-1-1 and B-1-2, T2 is -O-, -S-, -NR 80 - or -CR 81 R 82 -am.

[0511] In the above chemical formulas B-1-1 and B-1-2, R 80 , R 81 and R 82 is the same as the definition in the above chemical formula B-1.

[0512] According to one embodiment of the present invention, the above chemical formula 13 may be represented by any one of the following chemical formulas 13-2 to 13-5.

[0513] [Chemical Formula 13-2] [Chemical Formula 13-3]

[0514]

[0515] [Chemical Formula 13-4] [Chemical Formula 13-5]

[0516]

[0517] In the above chemical formulas 13-2 to 13-5, T2 is -O-, -S-, -NR 80 - or -CR 81 R 82 -am.

[0518] In the above chemical formulas 13-2 to 13-5, R 50 to R 71 , L 30 , R 80 , R 81 and R 82 is the same as the definition in Chemical Formula 13 above.

[0519] In the above chemical formulas 13-2 to 13-5, L 30 is R 62 to R 71 It connects to one of them.

[0520] According to one embodiment of the present invention, the above chemical formula 13 may be represented by the following chemical formula 13-6 or 13-7.

[0521] [Chemical Formula 13-6] [Chemical Formula 13-7]

[0522]

[0523] In the above chemical formulas 13-6 and 13-7, R 50 to R 71 and L 30 is the same as the definition in Chemical Formula 13 above.

[0524] In the above chemical formulas 13-6 and 13-7, L 30 is R 64 to R67 It can be connected to one of them.

[0525] According to one embodiment of the present invention, the above chemical formula 13 may include deuterium.

[0526] The compound represented by the above chemical formula 13 may be selected from the following compounds, but is not limited to them.

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound.

[0558] According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 13, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 13 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteriumization, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0559] An organic electroluminescent compound according to one embodiment of the present invention is represented by the following chemical formula 31.

[0560] [Chemical Formula 31]

[0561]

[0562] In the above chemical formula 31, R 51 to R61 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl ring, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one aspect of the present invention, R 51 to R 61 Each may independently be hydrogen, deuterium, halogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to another aspect of the present invention, R 51 to R 61 Each may independently be hydrogen, deuterium, halogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (3-20)heteroaryl, or a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C20) aromatic ring. For example, R 51 to R 61 Each can be hydrogen or deuterium independently.

[0563] In the above formula 31, Ar1 and Ar2 are each independently hydrogen, deuterium, or a substituted or unsubstituted (C6-C30)aryl, provided that Ar1 and Ar2 are not both hydrogen. According to one embodiment of the present invention, Ar1 and Ar2 are each independently hydrogen, deuterium, or a substituted or unsubstituted (C6-C20)aryl, and Ar1 and Ar2 are not both hydrogen. For example, Ar1 and Ar2 may each independently be hydrogen; deuterium; naphthyl substituted or unsubstituted phenyl; biphenyl; terphenyl; phenyl substituted or unsubstituted naphthyl; phenanthrenyl; triphenylenyl, and Ar1 and Ar2 are not both hydrogen, and may be further substituted with deuterium.

[0564] In the above chemical formula 31, R 100 to R 104 Each is independently hydrogen or deuterium.

[0565] The compound represented by the above chemical formula 31 may be selected from the following compounds, but is not limited to them.

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 31, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 31 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0585] An organic electroluminescent compound according to one embodiment of the present invention is represented by the following chemical formula 1-5.

[0586] [Chemical Formula 1-5]

[0587]

[0588] In the above chemical formulas 1-5, R1 to R5, and R7 to R 16Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted It is a tri(C6-C30)arylsilyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to one embodiment of the present invention, R1 to R5, and R7 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl. According to another aspect of the present invention, R1 to R5, and R7 to R 16 Each may independently be hydrogen, deuterium, or a substituted or unsubstituted (C6-C30)aryl. For example, R1 to R5, and R7 to R 16 Each can be independently hydrogen, deuterium, phenyl, etc.

[0589] In the above chemical formulas 1-5, L is a single bond.

[0590] In the above chemical formula 1-5, Ar is a substituted or unsubstituted phenanthrenyl group. For example, Ar is a phenanthrenyl group substituted with phenyl.

[0591] In the above chemical formula 1-5, the hydrogen in the above chemical formula can be substituted with deuterium.

[0592] The compound represented by the above chemical formula 1-5 may be selected from the following compounds, but is not limited to them.

[0593]

[0594]

[0595]

[0596]

[0597]

[0598] In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer from at least 1 to the maximum number of hydrogens in the compound. According to one embodiment of the present invention, when hydrogen is substituted with deuterium in any one of the compounds represented by Formula 1-5, the deuterium substitution rate is preferably about 100% or less of the total number of hydrogens, more preferably about 90% or less, even more preferably about 85% or less, and most preferably about 80% or less. The compound of Formula 1-5 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteriumization, and an organic electroluminescent device containing said compound can exhibit improved lifetime characteristics.

[0599] The compound represented by Formula 11 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 11 of the present invention may be prepared by referring to the synthesis methods disclosed in Reaction Scheme 3 below, Korean Registered Patent Publication No. 10-2283849, No. 10-1427457, etc., but is not limited thereto.

[0600] [Reaction Equation 3]

[0601]

[0602] In the above reaction scheme 3, R1 to R16 , L, Ar, a, and b are the same as defined in Chemical Formula 11. Also, in the above reaction scheme 3, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound.

[0603] The compound represented by Formula 12 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 12 of the present invention may be prepared by referring to the synthesis method disclosed in Reaction Scheme 4 or Reaction Scheme 5 below, but is not limited thereto.

[0604] [Reaction Equation 4]

[0605]

[0606] [Reaction Equation 5]

[0607]

[0608] In the above reaction schemes 4 and 5, R1 to R 16 , X, L1 and R 36 to R 43 is the same as the definition in Chemical Formula 12.

[0609] The compound represented by Formula 13 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 13 of the present invention may be prepared by referring to the synthesis method disclosed in Reaction Scheme 6 below, but is not limited thereto.

[0610] [Reaction Equation 6]

[0611]

[0612] The compound represented by Formula 31 according to the present invention may be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 31 of the present invention may be prepared by referring to the synthesis method disclosed in Reaction Scheme 7 below, but is not limited thereto.

[0613] [Reaction Equation 7]

[0614]

[0615] The compound represented by Formula 1-5 according to the present invention can be prepared by synthesis methods known to those skilled in the art. For example, the compound represented by Formula 1-5 of the present invention can be prepared by referring to the synthesis method disclosed in Reaction Scheme 8 below, but is not limited thereto.

[0616] [Reaction Equation 8]

[0617]

[0618] Although exemplary synthesis examples of compounds represented by chemical formulas 11, 12, 13, 31, and 1-5 have been described above, these are all based on Suzuki cross-coupling reaction, Wittig reaction, Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, N-arylation reaction, H-mont-mediated etherification reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphate-mediated reductive cyclization reaction, and it will be readily understood by those skilled in the art that the above reactions proceed even if other substituents defined in chemical formulas 11, 12, 13, 31, and 1-5 are attached in addition to the substituents specified in the specific synthesis examples. The organic electroluminescent compound represented by the above chemical formula 11 and containing at least one deuterium may have a residual hydrogen content of 10 to 20%, preferably 20 to 30%.

[0619] An organic electroluminescent compound according to one example of the present invention can be used as a light-emitting material for a white organic light-emitting device. Various structures of the white organic light-emitting device are proposed, such as a side-by-side arrangement, a stacking arrangement, or a color conversion material (CCM) arrangement, depending on the arrangement of R (red), G (green), YG (yellow-green), and B (blue) light-emitting parts. Additionally, the organic electroluminescent compound according to one example of the present invention can also be used in an organic light-emitting device containing quantum dots (QDs).

[0620] The organic electroluminescent device according to the present invention may further include an additional host material in the first light-emitting layer, an additional host material in the second light-emitting layer, or both layers may further include an additional host material in addition to the compound described above.

[0621] In the organic electroluminescent device according to the present invention, the light-emitting dopant of the first light-emitting layer may be the same as or different from the light-emitting dopant of the second light-emitting layer.

[0622] The organic electroluminescent device according to the present invention may be such that both the first light-emitting layer and the second light-emitting layer are light-emitting layers that emit blue light.

[0623] An organic electroluminescent device according to the present invention may further include, in addition to a light-emitting layer, one or more layers selected from a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. The organic electroluminescent device may further include an amine-based compound and / or an azine-based compound in addition to the light-emitting material of the present invention. Specifically, the hole injection layer, hole transport layer, hole assist layer, light-emitting layer, light-emitting assist layer, or electron blocking layer may include an amine-based compound, for example, an arylamine-based compound, a styrylarylamine-based compound, etc., as a hole injection material, a hole transport material, a hole assist material, a light-emitting material, a light-emitting assist material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may include an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. In addition, the organic layer may further include one or more metals selected from the group consisting of organometals of Group 1, Group 2, Period 4 transition metals, Period 5 transition metals, lanthanide metals, and d-transition elements, or one or more complex compounds containing such metals.

[0624] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the emissive layer. Multiple layers of the hole injection layer may be used to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two compounds may be used simultaneously in each layer. Additionally, the hole injection layer may be doped with a p-dopant. The electron blocking layer is located between the hole transport layer (or hole injection layer) and the emissive layer and can prevent light leakage by blocking the overflow of electrons from the emissive layer and trapping excitons within the emissive layer. Multiple layers of the hole transport layer or electron blocking layer may be used, and multiple compounds may be used in each layer.

[0625] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the emitting layer and the cathode. Multiple layers of the electron buffer layer may be used to control electron injection and improve the interface characteristics between the emitting layer and the electron injection layer, and two compounds may be used simultaneously in each layer. The hole blocking layer is a layer located between the electron transport layer (or electron injection layer) and the emitting layer that prevents holes from reaching the cathode, thereby improving the recombination probability of electrons and holes within the emitting layer. Multiple layers of the hole blocking layer or electron transport layer may also be used, and multiple compounds may be used in each layer. Additionally, the electron injection layer may be doped with an n-dopant.

[0626] The light-emitting auxiliary layer is a layer located between an anode and a light-emitting layer, or between a cathode and a light-emitting layer. When the light-emitting auxiliary layer is located between the anode and the light-emitting layer, it can be used to facilitate the injection and / or transport of holes or to block electron overflow. When the light-emitting auxiliary layer is located between the cathode and the light-emitting layer, it can be used to facilitate the injection and / or transport of electrons or to block hole overflow. Additionally, the hole auxiliary layer is located between the hole transport layer (or hole injection layer) and the light-emitting layer and can exhibit the effect of facilitating or blocking the transport speed (or injection speed) of holes, thereby allowing for the adjustment of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the additionally included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have the effect of improving the efficiency and / or lifespan of the organic electroluminescent device.

[0627] In the organic electroluminescent device of the present invention, it is preferable to arrange one or more layers selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layers") on the inner surface of at least one of a pair of electrodes. Specifically, it is preferable to arrange a silicon and aluminum chalcogenide (including oxide) layer on the anode surface on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the cathode surface on the side of the light-emitting medium layer. The operation stabilization of the organic electroluminescent device can be obtained through the surface layers. A preferred example of the chalcogenide is SiO₂. X (1≤X≤2), AlO XExamples include (1≤X≤1.5), SiON, SiAlON, etc., and preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0628] In addition, in the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidizing dopant on the surface of at least one of a pair of electrodes. In this manner, the electron transfer compound is reduced to an anion, making it easier to inject and transfer electrons from the mixed region to the light-emitting medium. In addition, the hole transfer compound is oxidized to a cation, making it easier to inject and transfer holes from the mixed region to the light-emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, an organic electroluminescent device that emits white light can be manufactured having two or more light-emitting layers by using the reducing dopant layer as a charge generation layer.

[0629] An organic electroluminescent device according to one embodiment of the present invention may further include one or more dopants in the light-emitting layer.

[0630] One or more phosphorescent or fluorescent dopants may be used as dopants included in the organic electroluminescent device according to the present invention, and fluorescent dopants are preferred. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, preferably, may be an orthometallated complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, more preferably, may be an orthometallated iridium complex compound.

[0631] A compound represented by the following chemical formula D may be used as a dopant included in the organic electroluminescent device according to the present invention, but is not limited thereto.

[0632] [Chemical Formula D]

[0633]

[0634] In the above chemical formula D,

[0635] R 101 to R 111 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or -L'4-N-(Ar'4)(Ar'5), or can be connected to an adjacent substituent to form a ring;

[0636] Y'1 is B and;

[0637] X'1 and X'2 are each independently NR';

[0638] R' is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or -L'4-N-(Ar'4)(Ar'5); or R 101 , R 108 , R 109 and R 111 It can be connected to one or more of them to form a ring;

[0639] L'4 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene;

[0640] Ar'4 and Ar'5 are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted fused ring of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl.

[0641] Preferably R 101 to R 111 Each can be independently hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-20)heteroaryl, or -L'4-N-(Ar'4)(Ar'5), or can be connected to an adjacent substituent to form a ring.

[0642] More preferably R101 to R 111 Each may be independently hydrogen, deuterium, unsubstituted (C1-C10)alkyl; (C6-C18)aryl substituted or unsubstituted with one or more of (C1-C10)alkyl, (13-18-membered) heteroaryl, and di(C6-C18)arylamino; (5-18-membered) heteroaryl substituted or unsubstituted with one or more (C1-C10)alkyls; or -L'4-N-(Ar'4)(Ar'5), or may be connected to adjacent substituents to form a ring. For example, R101 to R111 may each independently be a (17-21-membered) heteroaryl substituted with one or more of hydrogen, methyl, tert-butyl, substituted or unsubstituted phenyl, biphenyl, terphenyl, triphenylenyl, carbazolyl, phenoxazinyl, phenothiazinyl, dimethylacridinyl, dimethylxanthenyl, methyl, and diphenylamino, substituted or unsubstituted with one or more of diphenylamino, diphenylnaphthylamino, dibiphenylamino, phenylcarbazolyl, or dibenzofuranyl, substituted with phenylamino, methyl, and phenyl, or may be connected to adjacent substituents to form a benzene ring, an indole ring substituted with one or more of phenyl and diphenylamino, a benzofuran ring, a benzothiophen ring, or a 19-membered heteroaryl substituted with one or more methyl groups. The substituent of the above-mentioned substituted phenyl may be one or more of methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl, and dimethylacridinyl.

[0643] According to one embodiment of the present invention, specifically, the following compounds may be exemplified, but are not limited thereto.

[0644]

[0645]

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655]

[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665]

[0666]

[0667] In the above compounds, D2 to D5 each mean that 2 to 5 hydrogen atoms are replaced with deuterium.

[0668] The formation of each layer of the organic electroluminescent device of the present invention may be achieved using any one of the following methods: dry deposition methods such as vacuum deposition, sputtering, plasma, or ion plating, or wet deposition methods such as spin coating, dip coating, or flow coating. In the case of wet deposition methods, a thin film is formed by dissolving or dispersing the material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent may be used as long as the material forming each layer can be dissolved or dispersed in it and there is no problem with the filmability.

[0669] When forming a film of the first host material and the second host material according to one embodiment of the present invention, the film can be formed by the method listed above, and commonly, the film can be formed by a co-deposition or mixed deposition process. The co-deposition is a method of placing two or more materials into separate crucible sources and applying current to two cells simultaneously to evaporate the materials and perform mixed deposition, and the mixed deposition is a method of mixing two or more materials in one crucible source before deposition and then applying current to one cell to evaporate the materials and perform mixed deposition.

[0670] According to one embodiment of the present invention, when the first host material and the second host material exist in the same layer or different layers within an organic electroluminescent device, the two host compounds can each be individually deposited. For example, the second host material may be deposited after the first host material has been deposited.

[0671] According to one embodiment of the present invention, the present invention may provide a display device comprising a plurality of host materials including a first host material represented by Formula 1 and a second host material represented by Formula 2; an organic electroluminescent compound represented by Formula 11; or an organic electroluminescent compound represented by Formula 12. In addition, it is possible to manufacture a display device, for example, a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, for example, an outdoor or indoor lighting device, using the organic electroluminescent element of the present invention.

[0672] Hereinafter, the method for manufacturing the compound according to the present invention and its physical properties, as well as the driving voltage, converted efficiency, and lifetime characteristics of the OLED according to the present invention, are examined. However, the following examples are merely intended to explain the characteristics of the compound and OLED according to the present invention for a detailed understanding of the present invention, and the present invention is not limited to the following examples.

[0673] [Example 1] Preparation of Compound C-19

[0674]

[0675] 1) Synthesis of Compound 1-1

[0676] Compound A (50 g, 277 mmol) and THF (250 mL) were placed in a flask and dissolved; then, zinc (81.6 g, 1248 mmol) and ZnCl2 (49.8 g, 360 mmol) were added, and the mixture was reacted at room temperature for 1 hour. After the reaction was complete, the mixture was extracted with ethyl acetate and treated with MgSO4. After filtering and concentrating the organic layer, the resulting mixture was purified by column chromatography to obtain Compound 1-1 (42 g, yield: 85%).

[0677] 2) Synthesis of Compound 1-2

[0678] Compound 1-1 (40 g, 110 mmol) was placed in a 1 L round-bottom flask (RBF), and CHCl3 (600 mL) was added and dissolved. The reaction mixture was then cooled to 0°C, trifluoromethanesulfonic acid (128 mL, 1446 mmol) was added, and the mixture was stirred at 60°C for 18 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, extracted with dichloromethane, and treated with MgSO4. The organic layer was filtered and concentrated, and the resulting mixture was purified by column chromatography to obtain Compound 1-2 (14.3 g, yield: 40%).

[0679] 3) Synthesis of Compounds 1-3

[0680] Compound 1-2 (7.72 g, 23.5 mmol) and dichloromethane (240 mL) were placed in a flask and dissolved; subsequently, bromine (1.21 mL, 23.5 mmol) was added and reacted for 12 hours. After the reaction was complete, the mixture was neutralized with K2CO3 and an aqueous solution of sodium thiosulfate, extracted with dichloromethane, and treated with MgSO4. After filtering and concentrating the organic layer, the resulting mixture was purified by column chromatography to obtain Compound 1-3 (6.9 g, yield: 73%).

[0681] 4) Synthesis of Compound C-19

[0682] Compounds 1-3 (6.9g, 16.9mmol), Compound B (5.5g, 22mmol), Pd(PPh3)4 (580mg, 0.507mmol), K2CO3 (11.7g, 84.7mmol), toluene (45mL), ethanol (10mL), and distilled water (45mL) were added and refluxed for 15 hours. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate and then dried with magnesium sulfate. Subsequently, the organic layer was subjected to vacuum distillation and separated by column chromatography to obtain Compound C-19 (1.3g, yield: 14%).

[0683]

[0684] [Example 2] Preparation of Compound C-4

[0685]

[0686] Compound 1-3 (7 g, 17 mmol), Compound 2-1 (4.4 g, 22.34 mmol), Pd(PPh3)4 (590 mg, 0.515 mmol), K2CO3 (11.8 g, 85.93 mmol), toluene (45 mL), ethanol (11 mL), and distilled water (45 mL) were added to a flask and stirred under reflux for 8 hours. The mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, and then dried with magnesium sulfate. Subsequently, the organic layer was subjected to vacuum distillation and separated by column chromatography to obtain Compound C-4 (1.6 g, yield: 20%).

[0687]

[0688] [Example 3] Synthesis of Compound H2-256

[0689]

[0690] 1) Synthesis of Compound 5-2

[0691] Compound 5-1 (30 g, 156.07 mmol) was dissolved in 900 mL of methylene chloride (MC), and N-bromosuccinimide (NBS, 30.5 g, 171.67 mmol) was added. The mixture was refluxed and stirred for 2 hours, cooled to room temperature, and then stirred for 15 hours. An aqueous sodium thiosulfate solution was added to the mixture and stirred. The organic layer was separated, and the organic layer was neutralized by adding an aqueous Na2CO3 solution. The organic layer was separated, dried with magnesium sulfate, and then subjected to vacuum filtration followed by vacuum distillation. Compound 5-2 (36 g, yield: 85.10%) was obtained by separation using column chromatography.

[0692] 2) Synthesis of Compound H2-256

[0693] Compound 5-2 (20 g, 73.77 mmol), (10-phenylanthracene-9-yl)boronic acid (24.19 g, 81.14 mmol), Pd(OAc)2 (0.66 g, 2.95 mmol), S-phos (3.63 g, 8.85 mmol), 400 mL of toluene, K3PO4 (39.1 g, 184.4 mmol), 90 mL of distilled water, and 90 mL of ethanol were added to a flask and refluxed. The reaction mixture was cooled to room temperature after 4 hours. It was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain compound H2-256 (26 g, yield: 79.38%).

[0694]

[0695] [Example 4] Preparation of Compound H2-691-D14

[0696]

[0697] Compound H2-256 was synthesized by the deuteration method disclosed in Korean Registered Patent Publication No. 10-2283849 or No. 10-1427457, etc., to obtain compound H2-691-D14 (16.4 g, yield: 72.34 %, MS: [M+H]+ = 459.3).

[0698]

[0699] [Example 5] Preparation of Compound H2-259

[0700]

[0701] Compound 7-1 (16 g, 59.01 mmol), Compound 7-2 (24.29 g, 64.91 mmol), Pd(OAc)2 (0.53 g, 2.36 mmol), S-phos (2.42 g, 5.90 mmol), 400 mL of toluene, K3PO4 (25.05 g, 118.03 mmol), 80 mL of distilled water, and 40 mL of ethanol were added to a flask and refluxed. After 2 hours, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain Compound H2-259 (14.4 g, yield: 46.87%).

[0702]

[0703] [Example 6] Synthesis of Compound H2-694-D9

[0704]

[0705] Compound H2-259 was synthesized by the deuteration method disclosed in Korean Registered Patent Publication No. 10-2283849 or No. 10-1427457, etc., to obtain compound H2-694-D9 (7.4 g, yield: 60.70 %, MS: [M+H]+ = 530.1).

[0706]

[0707] [Example 7] Synthesis of Compound C3-1

[0708]

[0709] 1) Synthesis of Compound C3-1P-2

[0710] Compound 1-bromo-7-chlorophenanthrin (30 g, 124.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (47.3 g, 186.3 mmol), PdCl2(PPh3)2 (1.57 g, 6.21 mmol), KOAc (30.47 g, 310.54 mmol), and 600 mL of 1,4-dioxane were mixed in a flask and refluxed. After 2 hours, the mixture was cooled to room temperature. After vacuum distillation of 1,4-dioxane, the compound was separated by column chromatography. C3-1P-2 (32.0 g, yield: 89.28%) was obtained.

[0711] 2) Synthesis of Compound C3-1P-1

[0712] In a flask, compound 7-bromotetraphene (30.0 g, 97.66 mmol), compound C3-1P-2 (31 g, 107.42 mmol), Pd(PPh3)4 (5.64 g, 4.88 mmol), TBAB (3.14 g, 9.76 mmol), K2CO3 (33.74 g, 244.14 mmol), 800 mL of toluene, and 200 mL of distilled water were mixed and refluxed. After 4 hours and 30 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation, and the compounds were separated by column chromatography. C3-1P-1 (33.0 g, yield: 86.89%) was obtained.

[0713] 3) Synthesis of Compound C3-1

[0714] compound C3-1P-1Pd(OAc)2 (15.0 g, 38.57 mmol), phenylboronic acid (7.05 g, 57.85 mmol), Pd(OAc)2 (0.43 g, 1.20 mmol), X-phos (2.2 g, 4.62 mmol), K2CO3 (15.99 g, 115.71 mmol), 400 mL of toluene, 80 mL of distilled water, and 60 mL of ethanol were mixed and refluxed. After 2 hours, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compounds. C3-1 (13.5 g, yield: 81.29%) was obtained.

[0715]

[0716] [Example 8] Synthesis of Compound C3-5

[0717]

[0718] Compound C3-1P-1 (14.0 g, 35.99 mmol), 2-Naphthylboronic Acid (9.28 g, 53.99 mmol), Pd(OAc)2 (0.40 g, 1.79 mmol), X-phos (2.06 g, 4.32 mmol), K2CO3 (14.92 g, 107.9 mmol), 400 mL of toluene, 80 mL of distilled water, and 60 mL of ethanol were mixed in a flask and stirred under reflux. After 2 hours, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C3-5 (12.2 g, yield: 70.52%) was obtained.

[0719]

[0720] [Example 9] Synthesis of Compound C-366

[0721]

[0722] 1) Synthesis of Compound C-366P-1

[0723] 3-chlorophenanthrin (30.0 g, 141.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-b(1,3,2-dioxaborolane) (53.7 g, 211.6 mmol), Pd2(dba)3 (6.5 g, 7.05 mmol), SPhos (5.8 g, 14.1 mmol), KOAc (27.7 g, 282.1 mmol), and 750 mL of 1,4-dioxane were mixed in a flask and refluxed. After 2 hours, the mixture was cooled to room temperature. The 1,4-dioxane was subjected to vacuum distillation, and the compound was separated by column chromatography. C-366P-1 (34.9 g, yield: 81.31%) was obtained.

[0724] 2) Synthesis of Compound C-366

[0725] Compound in the flask C-366P-1 (20.1 g, 66.1 mmol), 2-chlorodibenzo[g, p]chrysine (20.0 g, 55.1 mmol), Pd(OAc)2 (0.62 g, 2.76 mmol), XPhos (2.6 g, 5.5 mmol), K2CO3 (19.0 g, 137.8 mmol), 400 mL of toluene, 80 mL of distilled water, and 80 mL of ethanol were added and refluxed. After 4 hours, the mixture was cooled to room temperature. Subsequently, distilled water was added to the mixture, and the organic layer was extracted with dichloromethane. Dichloromethane was added again to the remaining aqueous layer to further extract the organic layer, and the extracted organic layers were combined and dried using magnesium sulfate. The dried mixture was filtered under reduced pressure, followed by vacuum distillation, and the compounds were separated by column chromatography. C-366 (25.1 g, yield: 90.27%) was obtained.

[0726]

[0727] [Example 10] Synthesis of Compound C-541

[0728]

[0729] Compounds 7-bromotetraphene (12 g, 39.06 mmol), 4,4,5,5-tetramethyl-2-(phenantro[4,5-bcd]furan-8-yl)-1,3,2-dioxaborolane (14.91 g, 46.87 mmol), Pd(OAc)2 (0.33 g, 1.56 mmol), S-phos (1.92 g, 4.68 mmol), K3PO4 (20.73 g, 97.66 mmol), 300 mL of toluene, 80 mL of distilled water, and 80 mL of ethanol were mixed in a flask and refluxed. After 3 hours and 30 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-541 (13.5 g, yield: 82.61%) was obtained.

[0730]

[0731] [Example 11] Synthesis of Compound C-502

[0732]

[0733] Compounds 7-bromotetraphene (5.0 g, 16.27 mmol), 4,4,5,5-tetramethyl-2-(phenanthrene-1-yl)-1,3,2-dioxaborolane (6.0 g, 19.72 mmol), Pd(OAc)2 (0.14 g, 0.65 mmol), S-phos (0.8 g, 1.94 mmol), K3PO4 (8.64 g, 40.70 mmol), 125 mL of toluene, 35 mL of distilled water, and 35 mL of ethanol were mixed in a flask and refluxed. After 1 hour and 10 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-502 (1.8 g, yield: 27.35%) was obtained.

[0734]

[0735] [Example 12] Synthesis of Compound C-503

[0736]

[0737] Compounds 7-bromotetraphene (5.0 g, 16.27 mmol), 4,4,5,5-tetramethyl-2-(phenanthren-2-yl)-1,3,2-dioxaborolane (6.0 g, 19.72 mmol), Pd(OAc)2 (0.14 g, 0.65 mmol), S-phos (0.8 g, 1.94 mmol), K3PO4 (8.64 g, 40.70 mmol), 125 mL of toluene, 35 mL of distilled water, and 35 mL of ethanol were mixed and refluxed. After 1 hour and 40 minutes, the mixture was cooled to room temperature. Distilled water was added, and the organic layer was extracted with EA. Magnesium sulfate was added to the organic layer, dried, and filtered under reduced pressure. The organic layer was subjected to vacuum distillation. The compounds were separated by column. C-503 (4.0 g, yield: 60.77%) was obtained.

[0738]

[0739] [Example 13] Synthesis of Compound C-571

[0740]

[0741] 1) Synthesis of Compound C-571 P-2

[0742] Compound 7-bromotetraphene (12.0 g, 39.06 mmol), 4-chlorophenylboronic acid (7.33 g, 46.87 mmol), PdCl2(AMPHOS)2 (1.10 g, 1.56 mmol), TBAB (1.26 g, 3.90 mmol), Na2CO3 (12.42 g, 117.19 mmol), 300 mL of toluene, and 80 mL of distilled water were mixed in a flask and refluxed. After 1 hour, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation, and the compound was separated by column chromatography. C-571 P-2 (12.0 g, yield: 90.87%) was obtained.

[0743] 2) Synthesis of Compound C-571 P-1

[0744] Compound C-571 P-2 (12 g, 35.49 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-b(1,3,2-dioxaborolane) (13.51 g, 53.24 mmol), Pd2(dba)3 (1.62 g, 1.77 mmol), S-phos (1.45 g, 3.55 mmol), KOAc (10.44 g, 106.48 mmol), and 400 mL of 1,4-dioxane were mixed in a flask and refluxed. After 6 hours, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation, and the compounds were separated by column chromatography. C-571 P-1 (13.0 g, 85.11%) was obtained.

[0745] 3) Synthesis of Compound C-571

[0746] Compound C-571 P-1 (13.0 g, 30.20 mmol), 8-bromophenantro[4,5-bcd]furan (9.0 g, 33.22 mmol), Pd(OAc)2 (0.27 g, 1.20 mmol), S-phos (1.48 g, 3.62 mmol), K3PO4 (16.03 g, 75.52 mmol), 300 mL of toluene, 70 mL of distilled water, and 50 mL of ethanol were mixed in a flask and refluxed. After 4 hours and 10 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-571 (8.8 g, yield: 58.91%) was obtained.

[0747]

[0748] [Example 14] Synthesis of Compound C-576

[0749]

[0750] 1) Synthesis of Compound C-576 P-2

[0751] Compound 7-bromotetraphene (12.0 g, 39.06 mmol), (4-chloro-2-fluorophenyl)boronic acid (8.1 g, 46.87 mmol), PdCl2(AMPHOS)2 (1.10 g, 1.56 mmol), TBAB (1.26 g, 3.90 mmol), Na2CO3 (12.42 g, 117.19 mmol), 300 mL of toluene, and 80 mL of distilled water were mixed in a flask and refluxed. After 1 hour, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-576 P-2 (13.0 g, yield: 93.27%) was obtained.

[0752] 2) Synthesis of Compound C-576 P-1

[0753] Compound C-576 P-2 (13 g, 36.43 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-b(1,3,2-dioxaborolane) (13.87 g, 54.65 mmol), Pd2(dba)3 (1.66 g, 1.82 mmol), S-phos (1.49 g, 3.64 mmol), KOAc (10.72 g, 109.29 mmol), and 400 mL of 1,4-dioxane were mixed in a flask and refluxed. After 6 hours, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation, and the compounds were separated by column chromatography. C-576 P-1 (8.0 g, 48.97%) was obtained.

[0754] 3) Synthesis of Compound C-576

[0755] Compound C-576 P-1 (8.0 g, 17.84 mmol), 8-bromophenantro[4,5-bcd]furan (5.8 g, 21.41 mmol), Pd(OAc)2 (0.16 g, 7.13 mmol), S-phos (0.88 g, 2.14 mmol), K3PO4 (9.47 g, 44.61 mmol), 200 mL of toluene, 40 mL of distilled water, and 20 mL of ethanol were mixed in a flask and refluxed. After 3 hours and 10 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-576 (7.3 g, yield: 79.83%) was obtained.

[0756]

[0757] [Example 15] Synthesis of Compound C-501

[0758]

[0759] Compound 7-bromotetraphene (22.83 g, 74.30 mmol), phenanthrene-9-ylboronic acid (15.0 g, 67.55 mmol), Pd(OAc)2 (0.76 g, 3.37 mmol), S-phos (3.05 g, 7.43 mmol), K3PO4 (35.85 g, 168.88 mmol), 300 mL of toluene, 150 mL of distilled water, and 150 mL of ethanol were mixed in a flask and refluxed. After 1 hour and 10 minutes, the mixture was cooled to room temperature. The organic layer was extracted with EA and washed with distilled water. The organic layer was dried with magnesium sulfate and filtered under reduced pressure. The organic layer was subjected to vacuum distillation and separated by column chromatography to obtain the compound C-501 ( 20.0 g, yield: 66.54%) was obtained.

[0760]

[0761] [Example 16] Synthesis of Compound C-531

[0762]

[0763] Compound C-501 is synthesized by selecting from deuteriumation methods disclosed in Korean Registered Patent Publications No. 10-2283849, No. 10-1427457, etc. C-531 (12.2 g, Yield: 63.8 %, MS: [M+H] + =421.2) obtained.

[0764] [Example 17] Synthesis of Compound C-532

[0765]

[0766] Compound C-502 was synthesized by selecting from among the deuteriumation methods disclosed in Korean Registered Patent Publications No. 10-2283849, No. 10-1427457, etc., to produce Compound C-532 (11.0 g, yield: 46.2 %, MS: [M+H] + =423.3) obtained.

[0767] Hereinafter, for a detailed understanding of the present invention, a method for manufacturing an organic electroluminescent device comprising an organic electroluminescent compound according to the present invention and the characteristics thereof are described.

[0768] [Devices 1 to 3] Preparation of an organic electroluminescent device comprising a compound according to the present invention as a host

[0769] An organic electroluminescent device (OLED) according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then a compound was placed in a cell inside the vacuum deposition apparatus. HI Insert, and in another cell, a compound HT-1 After adding, the two substances are evaporated at different rates to form a compound HI and compounds HT-1 Compounds with respect to the total amount of HI A 10 nm thick hole injection layer was deposited by doping with an amount of 5 wt%. Subsequently, the compound HT-1A first hole transport layer with a thickness of 80 nm was formed by depositing it on the hole injection layer. Subsequently, a compound was placed in another cell within the vacuum deposition equipment. HT-2 [The material] was inserted, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 15 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, an emitting layer was deposited thereon as follows. First, as the first emitting layer, the first emitting layer host of Table 1 was placed as a host in a cell within the vacuum deposition equipment, and in another cell, a compound was placed as a dopant. BD After adding, the two materials were evaporated at different rates to dope the dopant at an amount of 2 wt% relative to the total amount of the host and dopant, thereby depositing a first emitting layer with a thickness of 5 nm on the second hole transport layer. Subsequently, as the second emitting layer, the second emitting layer host of Table 1 was placed as a host in a cell within a vacuum deposition apparatus, and a compound was placed as a dopant in another cell. BD After adding, the two materials were evaporated at different rates to dope the dopant at an amount of 2 wt% relative to the total amount of the host and dopant, thereby depositing a second emissive layer with a thickness of 13 nm on the first emissive layer. A compound as an electronic buffer layer. ET-1 Deposited to a thickness of 5 nm, and then a compound in two other cell locations EI-1 and compounds EI-2 A 25 nm thick electron transport layer was deposited on the electron buffer layer by adding and evaporating at a rate of 2:1. A compound was applied to two other cells. Yb : LiF An OLED was fabricated by adding and evaporating at a rate of 2:1 to deposit the electron injection layer to a thickness of 1 nm, and then depositing an Al cathode to a thickness of 80 nm using another vacuum deposition device. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.

[0770] [Comparative Example 1] Preparation of an organic electroluminescent device comprising a conventional compound as a host

[0771] An OLED was manufactured in the same manner as in Device Manufacturing Example 1, except that a single emitting layer with a thickness of 18 nm was deposited on the second hole transport layer using only the hosts of Table 1 below as the hosts of the emitting layer.

[0772] Table 1 below shows the driving voltage at a luminance of 1,000 nits, the converted efficiency, and the minimum time taken for the light intensity to drop from 100% to 95% at a luminance according to CIE color coordinates for the organic electroluminescent devices according to Device Manufacturing Examples 1 to 3 and Comparative Example 1 manufactured as described above (lifetime: T95). Here, the converted efficiency [Eff / Y] means the current efficiency [cd / A] divided by the CIE Y coordinate value.

[0773] [Table 1]

[0774]

[0775] From Table 1 above, it can be confirmed that an organic electroluminescent device comprising a specific combination of compounds according to the present invention as a host material has significantly improved conversion efficiency compared to an organic electroluminescent device comprising a conventional compound as a host material. Furthermore, it can be more stable in terms of thermal degradation. .

[0776] The compounds used in the above device manufacturing examples 1 to 3 and comparative example 1 are shown in Table 2 below.

[0777] [Table 2]

[0778]

[0779] [Device Manufacturing Example 4] Manufacturing of an organic electroluminescent device comprising a compound according to the present invention as a host

[0780] An organic electroluminescent device (OLED) according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then a compound was placed in a cell inside the vacuum deposition apparatus. HI Insert, and in another cell, a compound HT-1 After adding, the two substances are evaporated at different rates to form a compound HI and compounds HT-1 Compounds with respect to the total amount of HI A 10 nm thick hole injection layer was deposited by doping with an amount of 3 wt%. Subsequently, the compound HT-1 A first hole transport layer with a thickness of 80 nm was formed by depositing it on the hole injection layer. Subsequently, a compound was placed in another cell within the vacuum deposition equipment. HT-2 A second hole transport layer with a thickness of 15 nm was deposited on the first hole transport layer by applying current to the cell to evaporate it. After forming the hole injection layer and the hole transport layers, a first emissive layer was deposited thereon as follows: the compound of Table 3 was placed as a host in a cell within a vacuum deposition apparatus, and the compound was placed as a dopant in another cell. BD After adding, the two materials were evaporated at different rates to dope the dopant at an amount of 2 wt% relative to the total amount of the host and dopant, thereby depositing a first emitting layer with a thickness of 5 nm on the second hole transport layer. Subsequently, a second emitting layer was deposited on the first emitting layer as follows: as a host in a cell within a vacuum deposition apparatus H4-11:H2-231(1:1) Add the compound, and in another cell, the compound as a dopant. BD After adding, a second emissive layer with a thickness of 13 nm was deposited by depositing the host at a 1:1 weight ratio and doping with a dopant in an amount of 2 wt%. After depositing the emissive layer, a compound was used as a hole blocking layer material.ET-1 A thickness of 5 nm was deposited. Subsequently, as an electron transport layer material, a compound was deposited at each of two locations within the cell of the vacuum deposition equipment. EI-1 and EI-2 After adding, the two materials were deposited to a thickness of 25 nm in a weight ratio of 2:1. Subsequently, as an electron injection layer Yb and LiF An OLED was fabricated by depositing the material to a thickness of 1 nm on the electron transport layer at a weight ratio of 2:1, and then depositing an Al cathode to a thickness of 80 nm on the electron injection layer using a different vacuum deposition equipment. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.

[0781] [Comparative Example 2] Preparation of an organic electroluminescent device comprising a conventional compound as a host

[0782] An OLED was manufactured in the same manner as in Device Manufacturing Example 4, except that the compound of Table 3 below was used as the first light-emitting layer host.

[0783] The driving voltage, current efficiency, and the time taken for the light intensity to drop from 100% to 95% (lifetime: T95) when checking the lifespan with 2x acceleration for the organic electroluminescent device according to Device Manufacturing Example 4 and Comparative Example 2 manufactured as described above were measured, respectively, and the results are shown in Table 3 below.

[0784] [Table 3]

[0785]

[0786] From Table 3 above, it can be confirmed that the lifespan characteristics of an organic electroluminescent device containing a compound according to the present invention as a host are significantly improved compared to an organic electroluminescent device containing a conventional compound as a host. Furthermore, it can be more stable in terms of thermal degradation. .

[0787] The compounds used in the above device manufacturing example 4 and comparative example 2 are shown in Table 4 below.

[0788] [Table 4]

[0789]

[0790] [Devices 5 to 22] Preparation of an organic electroluminescent device comprising a compound according to the present invention as a host

[0791] An organic electroluminescent device (OLED) according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then a compound was placed in a cell inside the vacuum deposition apparatus. HI Insert, and in another cell, a compound HT-1 After adding, the two substances are evaporated at different rates to form a compound HI and compounds HT-1 Compounds with respect to the total amount of HI A 10 nm thick hole injection layer was deposited by doping with an amount of 5 wt%. Subsequently, the compound HT-1 A first hole transport layer with a thickness of 80 nm was formed by depositing it on the hole injection layer. Subsequently, a compound was placed in another cell within the vacuum deposition equipment. HT-2 A second hole transport layer with a thickness of 15 nm was deposited on the first hole transport layer by applying current to the cell to evaporate it. After forming the hole injection layer and the hole transport layers, an emitting layer was deposited thereon as follows. First, as the first emitting layer, the first emitting layer host of Table 5 was placed as a host in a cell within the vacuum deposition equipment, and in another cell, a compound was placed as a dopant. BD After adding, the two materials were evaporated at different rates to dope the dopant at an amount of 2 wt% relative to the total amount of the host and dopant, thereby depositing a first emitting layer with a thickness of 5 nm on the second hole transport layer. Subsequently, as the second emitting layer, the second emitting layer host of Table 5 was placed as a host in a cell within a vacuum deposition apparatus, and a compound was placed as a dopant in another cell. BDAfter adding, the two materials were evaporated at different rates to dope the dopant at an amount of 2 wt% relative to the total amount of the host and dopant, thereby depositing a second emissive layer with a thickness of 13 nm on the first emissive layer. A compound as an electronic buffer layer. ET-1 Deposited to a thickness of 5 nm, and then a compound in two other cell locations EI-1 and compounds EI-2 A 25 nm thick electron transport layer was deposited on the second emissive layer by adding and evaporating at a rate of 2:1. A compound was applied to two other cells. Yb:LiF An OLED was fabricated by adding and evaporating at a rate of 2:1 to deposit the electron injection layer to a thickness of 1 nm, and then depositing an Al cathode to a thickness of 80 nm using another vacuum deposition device. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.

[0792] [Comparative Example 3] Preparation of an organic electroluminescent device comprising a conventional compound as a host

[0793] An OLED was manufactured in the same manner as in Device Manufacturing Example 6, except that a single emitting layer with a thickness of 18 nm was deposited on the second hole transport layer using only the hosts of Table 5 below as the hosts of the emitting layer.

[0794] Table 5 below shows the driving voltage at a luminance of 1,000 nits, the converted efficiency, and the minimum time taken for the light intensity to drop from 100% to 95% at a luminance according to CIE color coordinates for the organic electroluminescent devices according to the device manufacturing examples and comparative examples manufactured as described above. Here, the converted efficiency [Eff / Y] means the current efficiency [cd / A] divided by the CIE Y coordinate value.

[0795] [Table 5]

[0796]

[0797]

[0798]

[0799] From Table 5 above, it can be seen that an organic electroluminescent device comprising a specific combination of compounds according to the present invention as a host material has significantly improved conversion efficiency and lifespan compared to an organic electroluminescent device comprising a conventional compound as a host material, while maintaining the driving voltage. Furthermore, it can be more stable in terms of thermal degradation.

[0800] The compounds used in the above device manufacturing examples and comparative examples are shown in Table 6 below.

[0801] [Table 6]

[0802]

[0803]

Claims

Claim 1 Organic electroluminescent compound represented by the following chemical formula 11 and containing at least one deuterium: [Chemical Formula 11] In the above chemical formula 11, R1 to R 16 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted A tri(C6-C30)arylsilyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; provided that R1 to R 16 At least one of them is -(L)a-(Ar)b; L is each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene; Ar is each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl; a is an integer from 1 to 4, and b is an integer from 1 to 4; and each L and Ar may be the same or different from each other. Claim 2 An organic electroluminescent compound according to claim 1, wherein the residual hydrogen content is 10 to 20%. Claim 3 An organic electroluminescent compound according to claim 1, wherein the residual hydrogen content is 20 to 30%. Claim 4 An organic electroluminescent compound according to claim 1, wherein the compound represented by the chemical formula 11 is selected from the following compounds: In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound. Claim 5 Organic electroluminescent compound represented by the following chemical formula 1-5: [Chemical Formula 1-5] In the above chemical formulas 1-5, R1 to R5, and R7 to R 16 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3-7)heterocycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted A tri(C6-C30)arylsilyl, or a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; L is a single bond; Ar is a substituted or unsubstituted phenanthrenyl group; and the hydrogen in the above formula can be substituted with deuterium. Claim 6 In claim 5, the organic electroluminescent compound represented by the above chemical formula 1-5 is selected from the following compounds: In the above compounds, Dn means that n hydrogens are substituted with deuterium, and n is an integer from 1 to the maximum number of hydrogens in the compound.

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