Compounds and organic light emitting devices comprising the same

Abstract

The present specification provides a compound of Chemical Formula 1 and an organic light emitting device comprising the same.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2020-0151878, filed with the Korean Patent Office on November 13, 2020, the entire contents of which are contained in this specification.

[0002] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a persistent demand for the development of new materials for organic light-emitting devices (OLEDs) as described above. For blue OLEDs, high color purity and long lifetime are essential, but the high energy levels of blue materials lead to instability, resulting in a lack of technologies capable of simultaneously achieving these properties. In recent years, thermally activated delayed-fluorescence materials with boron-containing core structures have been developed and have attracted attention due to their high efficiency and color purity; however, they suffer from high triplet energy and slow reverse intersystem crossing speeds, resulting in short lifetimes. Therefore, there is a need to develop blue OLEDs that simultaneously achieve high color purity and long lifetime. Summary of the Invention

[0005] Technical issues

[0006] This specification provides compounds and organic light-emitting devices containing them.

[0007] Solution to the problem

[0008] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] A1 and A2 may be the same as or different from each other, and each can be independently a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0013] Ar1 can be a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group.

[0014] At least one of R1 to R3 is a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, a substituted or unsubstituted heterocyclic group, or -NR11R12, and the remainder is hydrogen.

[0015] R11 and R12 may be the same as or different from each other, and each can be independently a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group.

[0016] This excludes cases where A1 and A2 are unsubstituted benzene rings and Ar1 is an unsubstituted benzene ring.

[0017] In addition, this specification provides an organic light-emitting device, including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the aforementioned compound.

[0018] Invention Effects

[0019] The compound according to one embodiment of this specification can be used as a material for the organic layer of an organic light-emitting device, thereby enabling improvements in high color purity, high efficiency, and / or lifetime characteristics in the organic light-emitting device. Attached Figure Description

[0020] Figure 1 and 2 An organic light-emitting device according to one embodiment of this specification is illustrated.

[0021] [Symbol Explanation]

[0022] 1: Substrate

[0023] 2: First electrode

[0024] 3: Emissive layer

[0025] 4: Second electrode

[0026] 5: Hole injection layer

[0027] 6: Hole transport layer

[0028] 7: Electron blocking layer

[0029] 8: First electron transport layer

[0030] 9: Second electron transport layer

[0031] 10: Electron Injection Layer Detailed Implementation

[0032] The following is a more detailed description of this instruction manual.

[0033] Organic light-emitting devices (OLEDs) using existing boron-based compounds are more efficient than those using pyrene-based compounds, but suffer from shorter lifetimes. However, the compound represented by Formula 1 contains a boron core with a five-membered ring, unlike existing boron cores containing a six-membered ring. Therefore, its HOMO and LUMO band gaps are similar or smaller, making it suitable as a fluorescent dopant. Furthermore, the first triplet excitation energy of Formula 1 is lower, increasing the difference between the first singlet and first triplet excitation energies. This suppresses triplet quenching, thereby increasing the device lifetime and efficiency of OLEDs containing this compound in the host-dopant system.

[0034] Throughout the description of this application, the term "combination of them" in the Markush form refers to a mixture or combination of one or more of the constituent elements described in the Markush form, and means including one or more of the aforementioned constituent elements.

[0035] Examples of substituents in this specification are described below, but are not limited thereto.

[0036] In this instruction manual, Indicates the part that is connected.

[0037] The term "substitution" means that the hydrogen atom on the carbon atom of the compound is replaced by another substituent. There is no limitation on the position where the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0038] In this specification, the term "substituted or unsubstituted" refers to a substance selected from deuterium, halogen groups, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, and alkyl thio groups. aryl thiols It is substituted by one or more substituents selected from alkenyl, haloalkyl, haloalkoxy, arylalkyl, silyl, boron, amino, aryl and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents listed above, or it does not have any substituents.

[0039] In this specification, "two or more substituents linked" means that the hydrogen of any one substituent is linked to another substituent. For example, two substituents linked can be a phenyl group linked to a naphthyl group to form... Such substituents. Furthermore, the connection of three substituents not only includes a sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also includes (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl, and isopropyl can be linked to form... Such substituents. The same definition applies to connections of four or more substituents.

[0040] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0041] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0042] In this specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl with 3 to 30 carbon atoms. Specifically, it includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, norbornyl, etc., but is not limited to these.

[0043] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 30. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0044] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0045] In this specification, the above-mentioned haloalkyl refers to a hydrogen atom that has been replaced by at least one halogen group instead of the alkyl group defined above.

[0046] In this specification, the above-mentioned haloalkoxy group refers to a hydrogen atom that has at least one halogen group replacing the alkoxy group defined above.

[0047] In this specification, aryl is not particularly limited, but is preferably an aryl with 6 to 30 carbon atoms, and the aryl can be monocyclic or polycyclic.

[0048] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 6 to 30 carbon atoms. Specifically, the monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited to these.

[0049] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferred to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group can be naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, beryl, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0050] In this specification, the fluorene group can be substituted, and adjacent groups can combine with each other to form a ring.

[0051] When the aforementioned fluorene group is replaced, there is

[0052] etc., but not limited to this.

[0053] In this specification, "adjacent" groups can refer to substituents that are directly bonded to the atom substituted by the substituent, substituents that are stereomorphically closest to the substituent, or other substituents that are substituted to the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0054] In this specification, arylalkyl means that the alkyl group is replaced by an aryl group, and the aryl and alkyl groups of the above-mentioned arylalkyl can be used as examples of the aryl and alkyl groups described above.

[0055] In this specification, aryloxy refers to the alkyl group of an alkoxy group as defined above, in which the alkyl group is replaced by an aryl group. Examples of aryloxy groups include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, and 9-phenanthoxy, but are not limited to these.

[0056] In this specification, the alkyl group of alkyl thio group is the same as the alkyl group exemplified above. Specifically, alkyl thio groups include methyl thio, ethyl thio, tert-butyl thio, hexyl thio, octyl thio, etc., but are not limited to these.

[0057] In this specification, the aryl group in aryl thio group is the same as the aryl group exemplified above. Specifically, aryl thio groups include phenyl thio, 2-methylphenyl thio, 4-tert-butylphenyl thio, etc., but are not limited to these.

[0058] In this specification, a heterocyclic group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S, including aromatic heterocyclic groups or aliphatic heterocyclic groups. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but preferably 2 to 30. The heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl groups. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthroline, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol (phenoxathiine), phen Phenoxazine, phenothiazine, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzodiazepine, dihydroindobenzocarbazolyl, spirofluorenzanthryl, spirofluorenthiophenyl, tetrahydronaphthothiophenyl, tetrahydronaphthofuranyl, tetrahydrobenzothiophenyl, and tetrahydrobenzofuranyl, etc., but not limited to these.

[0059] In this specification, the aforementioned silane group can be alkylsilane, arylsilane, alkylarylsilane, heteroarylsilane, etc. The alkyl group in the aforementioned alkylsilane can be any of the examples of the aforementioned alkyl groups; the aryl group in the aforementioned arylsilane can be any of the examples of the aforementioned aryl groups; the alkyl and aryl groups in the aforementioned alkylarylsilane can be any of the examples of the aforementioned alkyl and aryl groups; and the heteroaryl group in the aforementioned heteroarylsilane can be any of the examples of the aforementioned heterocyclic groups.

[0060] In this specification, the boron group can be -BR 100 R 101 The above R 100 and R 101 Whether identical or different, each group can be independently selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted straight-chain or branched alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups with 2 to 30 carbon atoms. Specific examples of the aforementioned boryl groups include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but are not limited to these.

[0061] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited to these.

[0062] In this specification, N-alkylarylamine refers to an amino group in which an alkyl or aryl group is substituted for the N group. The alkyl and aryl groups in the above-described N-alkylarylamine are the same as those exemplified above.

[0063] In this specification, N-arylheteroarylamine refers to an amino group in which an aryl or heteroaryl group is substituted at the N-position of the amino group. The aryl and heteroaryl groups in the above-described N-arylheteroarylamine are the same as those exemplified above for aryl and heterocyclic groups.

[0064] In this specification, N-alkylheteroarylamine refers to an amino group in which an alkyl or heteroaryl group is substituted for the N group. The alkyl and heteroaryl groups in the above-described N-alkylheteroarylamine are the same as those exemplified above for alkyl and heterocyclic groups.

[0065] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups and substituted or unsubstituted dialkylamine groups. The alkyl group in the above-described alkylamine group can be a straight-chain or branched alkyl group. An alkylamine group containing two or more of the above-described alkyl groups can contain a straight-chain alkyl group, a branched alkyl group, or both a straight-chain alkyl group and a branched alkyl group. For example, the alkyl group in the above-described alkylamine group can be selected from the examples of the alkyl groups described above.

[0066] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines and substituted or unsubstituted di-heteroarylamines. Heteroarylamines containing two or more of the above-mentioned heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or both. For example, the heteroaryl groups in the above-mentioned heteroarylamines may be selected from the examples of heterocyclic groups described above.

[0067] In this specification, the alkyl group in N-alkylarylamine, alkylthio, and N-alkylheteroarylamine is the same as the alkyl group exemplified above. Specifically, alkylthio groups include methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, etc., but are not limited to these.

[0068] In this specification, the aryl groups in aryloxy, arylthio, N-arylalkylamine, and N-arylheteroarylamine are the same as those exemplified above. Specifically, as aryloxy groups, there are phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc., and as arylthio groups, there are phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., but these are not limited to these.

[0069] In this specification, the hydrocarbon cyclogroup can be an aromatic hydrocarbon cyclogroup, an aliphatic hydrocarbon cyclogroup, or a fused cyclogroup of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from the above-mentioned cycloalkyl, aryl, and combinations thereof. The above-mentioned hydrocarbon cyclogroups include phenyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, tetrahydronaphthyl, tetrahydroanthrayl, 1,2,3,4-tetrahydro-1,4-methylenenaphthyl and 1,2,3,4-tetrahydro-1,4-ethylnaphthyl, etc., but are not limited to these.

[0070] In this specification, the meaning of "adjacent" in "to form a ring by combining with adjacent groups" is the same as the definition above, where "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0071] In this specification, the hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. Except for not being monovalent as described above, it can be selected from the examples of the above-mentioned cycloalkyl, aryl, and combinations thereof. The above-mentioned hydrocarbon rings include benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methylenenaphthalene, and 1,2,3,4-tetrahydro-1,4-ethylenenaphthalene, etc., but are not limited to these.

[0072] In this specification, a heterocycle comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. The aromatic heterocycles, except that they are not monovalent, may be selected from examples of heteroaryl groups among the aforementioned heterocyclic groups.

[0073] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxacycloheptane, azirrocyclooctane, thiocyclooctane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, etc., but not limited to these.

[0074] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar to or equivalent to those described herein may be used to implement or test embodiments of the invention, but suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is mentioned, this specification, including its definitions, takes precedence. Furthermore, materials, methods, and embodiments are illustrative only and not intended to be limiting.

[0075] According to one embodiment of this specification, at least one of the hydrogen atoms at the substituted positions in the above-described chemical formula 1 is replaced by deuterium.

[0076] According to one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] [Chemical Formulas 1-3]

[0082]

[0083] [Chemical Formulas 1-4]

[0084]

[0085] In the above chemical formulas 1-1 to 1-4,

[0086] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0087] X1 and X2 may be the same or different from each other, and each can be O or S independently.

[0088] A11 and A21 may be the same as or different from each other, and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0089] Z1 to Z4, Y1 to Y5, and T1 to T4 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0090] In the above chemical formula 1-1, the cases where Z1 to Z4, Y1 to Y5 and T1 to T4 are all hydrogen are not included.

[0091] According to one embodiment of this specification, the above chemical formula 1-2 is represented by the following chemical formula 1-2-1 or 1-2-2.

[0092] [Chemical Formula 1-2-1]

[0093]

[0094] [Chemical Formula 1-2-2]

[0095]

[0096] In the above chemical formulas 1-2-1 and 1-2-2,

[0097] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0098] The definitions of X1, A21, Z1 to Z4, and Y1 to Y5 are the same as those in the above chemical formulas 1-2.

[0099] According to one embodiment of this specification, the above chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-3 to 1-2-6.

[0100] [Chemical Formula 1-2-3]

[0101]

[0102] [Chemical Formula 1-2-4]

[0103]

[0104] [Chemical Formula 1-2-5]

[0105]

[0106] [Chemical Formula 1-2-6]

[0107]

[0108] In the above chemical formulas 1-2-3 to 1-2-6,

[0109] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0110] The definitions of A21, Z1 to Z4, and Y1 to Y5 are the same as those in the above chemical formulas 1-2.

[0111] According to one embodiment of this specification, the above chemical formulas 1-3 are represented by chemical formulas 1-3-1 or 1-3-2.

[0112] [Chemical Formula 1-3-1]

[0113]

[0114] [Chemical Formula 1-3-2]

[0115]

[0116] In the above chemical formulas 1-3-1 and 1-3-2,

[0117] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0118] The definitions of X2, A11, T1 to T4, and Y1 to Y5 are the same as those in the above chemical formulas 1-3.

[0119] According to one embodiment of this specification, the above chemical formulas 1-3 are represented by any one of the following chemical formulas 1-3-3 to 1-3-6.

[0120] [Chemical Formula 1-3-3]

[0121]

[0122] [Chemical Formula 1-3-4]

[0123]

[0124] [Chemical Formula 1-3-5]

[0125]

[0126] [Chemical Formula 1-3-6]

[0127]

[0128] In the above chemical formulas 1-3-3 to 1-3-6,

[0129] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0130] The definitions of A11, T1 to T4, and Y1 to Y5 are the same as those in the above chemical formulas 1-3.

[0131] According to one embodiment of this specification, the above chemical formulas 1-4 are represented by any one of the following chemical formulas 1-4-1 to 1-4-4.

[0132] [Chemical Formula 1-4-1]

[0133]

[0134] [Chemical Formula 1-4-2]

[0135]

[0136] [Chemical Formula 1-4-3]

[0137]

[0138] [Chemical Formula 1-4-4]

[0139]

[0140] In the above chemical formulas 1-4-1 to 1-4-4,

[0141] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0142] The definitions of A11, A21, X1, X2 and Y1 to Y5 are the same as those in the above chemical formulas 1-4.

[0143] According to one embodiment of this specification, the above chemical formulas 1-4 are represented by any one of the following chemical formulas 1-4-5 to 1-4-20.

[0144] [Chemical Formula 1-4-5]

[0145]

[0146] [Chemical Formula 1-4-6]

[0147]

[0148] [Chemical Formula 1-4-7]

[0149]

[0150] [Chemical Formula 1-4-8]

[0151]

[0152] [Chemical Formula 1-4-9]

[0153]

[0154] [Chemical Formula 1-4-10]

[0155]

[0156] [Chemical Formula 1-4-11]

[0157]

[0158] [Chemical Formula 1-4-12]

[0159]

[0160] [Chemical Formula 1-4-13]

[0161]

[0162] [Chemical Formula 1-4-14]

[0163]

[0164] [Chemical Formula 1-4-15]

[0165]

[0166] [Chemical Formula 1-4-16]

[0167]

[0168] [Chemical Formula 1-4-17]

[0169]

[0170] [Chemical Formula 1-4-18]

[0171]

[0172] [Chemical Formula 1-4-19]

[0173]

[0174] [Chemical Formula 1-4-20]

[0175]

[0176] In the above chemical formulas 1-4-5 to 1-4-20,

[0177] The definitions of R1 to R3 are the same as those in Chemical Formula 1 above.

[0178] The definitions of A11, A21, and Y1 to Y5 are the same as those in the above chemical formulas 1-4.

[0179] According to one embodiment of this specification, at least one of R1 to R3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or -NR11R12, and the remainder is hydrogen.

[0180] According to one embodiment of this specification, at least one of R1 to R3 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted by one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof; an aromatic hydrocarbon ring having 6 to 30 carbon atoms that is substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms; and an ester ring having 3 to 30 carbon atoms that is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms. A fused ring group of an aliphatic hydrocarbon ring; composed of one or more substituted or unsubstituted monocyclic or polycyclic groups of 2 to 30 carbon atoms selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 30 carbon atoms (straight or branched), alkenyl groups with 2 to 30 carbon atoms (straight or branched), aryl groups with 6 to 30 carbon atoms (monocyclic or polycyclic), heterocyclic groups with 2 to 30 carbon atoms (monocyclic or polycyclic), and combinations thereof; or -NR11R12, the remainder being hydrogen.

[0181] According to one embodiment of this specification, at least one of R1 to R3 is a phenyl group substituted or unsubstituted with any one or more of a straight-chain or branched alkyl group selected from deuterium, alkyl groups having 1 to 30 carbon atoms, and combinations thereof; biphenyl; terphenyl; naphthyl; anthraceneyl; phenanthryl; tetrahydronaphthyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; carbazole group; or a group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. The triazine group is selected from one or more of the following: a hexahydrocarbazolyl group; a dibenzofuranyl group; a dibenzothiophene group; a triazine group selected from deuterium, a halogen group, a cyano group, an alkyl group with 1 to 30 carbon atoms that is straight or branched, an alkenyl group with 2 to 30 carbon atoms that is straight or branched, an aryl group with 6 to 30 carbon atoms that is monocyclic or polycyclic, a heterocyclic group with 2 to 30 carbon atoms that is monocyclic or polycyclic, and combinations thereof; or -NR11R12, the remainder being hydrogen.

[0182] According to one embodiment of this specification, at least one of R1 to R3 is a phenyl group selected from deuterium, methyl, and combinations thereof, either substituted or unsubstituted; biphenyl; terphenyl; naphthyl; anthracene; phenanthrene; tetrahydronaphthyl substituted or unsubstituted with methyl; carbazolyl; hexahydrocarbazolyl substituted or unsubstituted with methyl; dibenzofuran; dibenzothiophene; triazine group selected from deuterium, F, cyano, methyl, tert-butyl, vinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, spirodifluorenyl, pyrene, pyridyl, dibenzofuranyl, dibenzothiophene, carbazolyl, and combinations thereof, either substituted or unsubstituted with methyl; or -NR11R12, the remainder being hydrogen.

[0183] According to one embodiment of this specification, any one of R1 to R3 is a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms (substituted or unsubstituted), a heterocyclic group of a monocyclic or polycyclic aromatic hydrocarbon ring with 2 to 30 carbon atoms (substituted or unsubstituted), or -NR11R12, and the remainder is hydrogen.

[0184] According to one embodiment of this specification, any one of R1 to R3 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted by one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof; or an aromatic hydrocarbon ring having 6 to 30 carbon atoms that is substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and an ester ring having 3 to 30 carbon atoms. A fused ring group of an aliphatic hydrocarbon ring; composed of one or more substituted or unsubstituted monocyclic or polycyclic groups of 2 to 30 carbon atoms selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 30 carbon atoms (straight or branched), alkenyl groups with 2 to 30 carbon atoms (straight or branched), aryl groups with 6 to 30 carbon atoms (monocyclic or polycyclic), heterocyclic groups with 2 to 30 carbon atoms (monocyclic or polycyclic), and combinations thereof; or -NR11R12, the remainder being hydrogen.

[0185] According to one embodiment of this specification, any one of R1 to R3 is a phenyl group substituted or unsubstituted with one or more of a straight-chain or branched alkyl group selected from deuterium, alkyl groups having 1 to 30 carbon atoms, and combinations thereof; biphenyl; terphenyl; naphthyl; anthraceneyl; phenanthreneyl; tetrahydronaphthyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; carbazole group; or a group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. The triazine group is selected from one or more of the following: a hexahydrocarbazolyl group; a dibenzofuranyl group; a dibenzothiophene group; a triazine group selected from deuterium, a halogen group, a cyano group, an alkyl group with 1 to 30 carbon atoms that is straight or branched, an alkenyl group with 2 to 30 carbon atoms that is straight or branched, an aryl group with 6 to 30 carbon atoms that is monocyclic or polycyclic, a heterocyclic group with 2 to 30 carbon atoms that is monocyclic or polycyclic, and combinations thereof; or -NR11R12, the remainder being hydrogen.

[0186] According to one embodiment of this specification, any one of R1 to R3 is a phenyl group selected from deuterium, methyl, and combinations thereof, either substituted or unsubstituted; biphenyl; terphenyl; naphthyl; anthracene; phenanthrene; tetrahydronaphthyl substituted or unsubstituted with methyl; carbazolyl; hexahydrocarbazolyl substituted or unsubstituted with methyl; dibenzofuran; dibenzothiophene; triazine group selected from deuterium, F, cyano, methyl, tert-butyl, vinyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, spirodifluorenyl, pyrene, pyridyl, dibenzofuranyl, dibenzothiophene, carbazolyl, and combinations thereof, either substituted or unsubstituted with methyl; or -NR11R12, the remainder being hydrogen.

[0187] According to one embodiment of this specification, R11 and R12 may be the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0188] According to one embodiment of this specification, R11 and R12 may be the same as or different from each other, and each independently is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted by any one or more of deuterium, straight-chain or branched alkyl groups with 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, and combinations thereof; a fused ring group consisting of an aromatic hydrocarbon ring with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms; or a heterocyclic group consisting of a monocyclic or polycyclic group with 2 to 30 carbon atoms substituted or unsubstituted by an aryl group with 6 to 30 carbon atoms.

[0189] According to one embodiment of this specification, R11 and R12 may be the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with any one or more of the following: deuterium, straight-chain or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms, and combinations thereof; biphenyl substituted or unsubstituted with deuterium; terphenyl; naphthyl; phenanthrene; fluorenyl substituted or unsubstituted with straight-chain or branched alkyl groups having 1 to 30 carbon atoms; tetrahydronaphthyl substituted or unsubstituted with straight-chain or branched alkyl groups having 1 to 30 carbon atoms; dibenzofuranyl; dibenzothiopheneyl; or carbazoyl substituted or unsubstituted with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0190] According to one embodiment of this specification, R11 and R12 may be the same as or different from each other, and each independently is a phenyl group selected from deuterium, methyl, tert-butyl, cyclohexyl, and combinations thereof, either substituted or unsubstituted; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group; a phenanthryl group; a fluorenyl group substituted or unsubstituted with methyl; a tetrahydronaphthyl group substituted or unsubstituted with methyl; a dibenzofuranyl group; a dibenzothiophenyl group; or a carbazole group substituted or unsubstituted with phenyl.

[0191] According to one embodiment of this specification, A1 and A2 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms, a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms, or a heterocyclic monocyclic or polycyclic ring with 2 to 30 substituted or unsubstituted carbon atoms.

[0192] According to one embodiment of this specification, A1 and A2 may be the same as or different from each other, and each independently represents one or more substituted or unsubstituted carbons selected from a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 atoms; a fused ring consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a heterocyclic ring having 2 to 30 carbon atoms substituted or unsubstituted with one or more of deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof.

[0193] According to one embodiment of this specification, A1 and A2 may be the same as or different from each other, and each is independently a benzene substituted or unsubstituted with any one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof; naphthalene; fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Tetrahydronaphthalene; tetrahydrobenzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophene; benzofuran; or benzothiophene substituted or unsubstituted with any one or more of deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof.

[0194] According to one embodiment of this specification, A1 and A2 may be the same as or different from each other, and each independently represents benzene substituted or unsubstituted with any one or more of methyl, isopropyl, tert-butyl, cyclohexyl, phenyl, diphenylamino, diphenylamino, dinaphthylamino, hexahydrocarbazole, and combinations thereof; naphthalene; fluorene substituted or unsubstituted with methyl; tetrahydronaphthalene substituted or unsubstituted with methyl; tetrahydrobenzofuran substituted or unsubstituted with methyl; tetrahydrobenzothiophene substituted or unsubstituted with methyl; tetrahydronaphthiophene substituted or unsubstituted with methyl; tetrahydronaphthiophene substituted or unsubstituted with methyl; dibenzofuran; dibenzothiophene; benzofuran; or benzothiophene substituted or unsubstituted with any one or more of deuterium, methyl, tert-butyl, and combinations thereof.

[0195] According to one embodiment of this specification, Ar1 is an aryl group of monocyclic or polycyclic compounds with 6 to 30 carbon atoms (substituted or unsubstituted), a fused ring group of an aromatic hydrocarbon ring with 6 to 30 carbon atoms and an aliphatic hydrocarbon ring with 3 to 30 carbon atoms (substituted or unsubstituted), or a heterocyclic group of monocyclic or polycyclic compounds with 2 to 30 carbon atoms (substituted or unsubstituted).

[0196] According to one embodiment of this specification, Ar1 is a fused ring group consisting of one or more substituted or unsubstituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and combinations thereof; a fused ring group consisting of one or more substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon rings with 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon rings with 3 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms; or a heterocyclic group consisting of monocyclic or polycyclic aryl groups with 2 to 30 carbon atoms substituted or unsubstituted by straight-chain or branched alkyl groups with 1 to 30 carbon atoms.

[0197] According to one embodiment of this specification, Ar1 is a phenyl group substituted or unsubstituted with any one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof; a biphenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; a naphthyl group; or a fluorenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Tetrahydronaphthyl group substituted or unsubstituted by any one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and combinations thereof; tetrahydrobenzofuranyl group substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzothiophenyl group substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms; benzofuranyl group; benzothiophenyl group; dibenzofuranyl group; or dibenzothiophenyl group.

[0198] According to one embodiment of this specification, Ar1 is a phenyl group substituted or unsubstituted with any one or more of methyl, isopropyl, tert-butyl, cyclohexyl, phenyl, and combinations thereof; a biphenyl group substituted or unsubstituted with tert-butyl; naphthyl; a fluorenyl group substituted or unsubstituted with methyl; a tetrahydronaphthyl group substituted or unsubstituted with any one or more of methyl, phenyl, and combinations thereof; a tetrahydrobenzofuranyl group substituted or unsubstituted with methyl; a tetrahydrobenzothiophenyl group substituted or unsubstituted with methyl; a benzofuranyl group; a benzothiophenyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0199] According to one embodiment of this specification, any one of R1 to R3 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted by one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof; or an aromatic hydrocarbon ring having 6 to 30 carbon atoms that is substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and an ester ring having 3 to 30 carbon atoms. A fused-ring group of an aliphatic hydrocarbon ring; substituted or unsubstituted with one or more of a monocyclic or polycyclic heterocyclic group of 2 to 30 carbon atoms selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 30 carbon atoms (straight-chain or branched), alkenyl groups with 2 to 30 carbon atoms (straight-chain or branched), aryl groups with 6 to 30 carbon atoms (monocyclic or polycyclic), heterocyclic groups with 2 to 30 carbon atoms (monocyclic or polycyclic), and combinations thereof; or -NR11R12, the remainder being hydrogen.

[0200] R11 and R12 may be the same as or different from each other, and each independently is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted by one or more of a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 carbon atoms, and combinations thereof; a fused ring group consisting of an aromatic hydrocarbon ring with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms; or a heterocyclic group consisting of a monocyclic or polycyclic alkyl group with 2 to 30 carbon atoms substituted or unsubstituted by an aryl group with 6 to 30 carbon atoms.

[0201] The above A1 and A2 may be the same as or different from each other, and each independently consists of one or more substituted or unsubstituted carbons of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof. A monocyclic or polycyclic aromatic hydrocarbon ring of 0; a fused ring consisting of a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group of 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring of 3 to 30 carbon atoms; or a heterocyclic ring consisting of a monocyclic or polycyclic aromatic hydrocarbon ring of 2 to 30 carbon atoms substituted or unsubstituted with one or more of deuterium, a straight-chain or branched alkyl group of 1 to 30 carbon atoms, and combinations thereof.

[0202] The Ar1 mentioned above is a fused ring group consisting of one or more substituted or unsubstituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and combinations thereof; or a heterocyclic group consisting of monocyclic or polycyclic aryl groups with 2 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and combinations thereof; a fused ring group consisting of a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted; or a heterocyclic group consisting of a monocyclic or polycyclic aryl group with 2 to 30 carbon atoms selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms.

[0203] This excludes cases where A1 and A2 are unsubstituted benzenes and Ar1 is an unsubstituted phenyl.

[0204] According to one embodiment of this specification, Z1 to Z4 may be the same as or different from each other, and each is independently a substituted or unsubstituted hydrogen, deuterium, straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, formed by combining with adjacent groups.

[0205] According to one embodiment of this specification, Z1 to Z4 may be the same as or different from each other, and each is independently hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a group substituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms. A heterocyclic group consisting of 2 to 30 straight-chain or branched alkyl-substituted or unsubstituted monocyclic or polycyclic rings with 2 to 30 carbon atoms, or a monocyclic or polycyclic ring consisting of 3 to 30 carbon atoms with substituted or unsubstituted monocyclic or polycyclic rings ... monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted mono

[0206] According to one embodiment of this specification, Z1 to Z4 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, diphenylamino, diphenylamino, dianathylamino, phenyl, or hexahydrocarbazole, or benzene, formed by combination with adjacent groups, indene, cyclohexane, benzofuran, or benzothiophene.

[0207] According to one embodiment of this specification, Z1 to Z4 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, diphenylamino (substituted or unsubstituted with tert-butyl), diphenylamino, dinaphthylamino, phenyl, or hexahydrocarbazole (substituted or unsubstituted with methyl), or is combined with adjacent groups to form benzene, indene (substituted or unsubstituted with methyl), cyclohexane (substituted or unsubstituted with methyl), benzofuran, or benzothiophene.

[0208] According to one embodiment of this specification, T1 to T4 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic diarylamine group with 6 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms, formed by combining with adjacent groups.

[0209] According to one embodiment of this specification, T1 to T4 may be the same as or different from each other, and each is independently hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or a group substituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms. A heterocyclic group consisting of 2 to 30 straight-chain or branched alkyl-substituted or unsubstituted monocyclic or polycyclic rings with 2 to 30 carbon atoms, or a monocyclic or polycyclic ring consisting of 3 to 30 carbon atoms with substituted or unsubstituted monocyclic or polycyclic rings ... monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted monocyclic or polycyclic rings with substituted mono

[0210] According to one embodiment of this specification, T1 to T4 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, diphenylamino, diphenylamino, dianathylamino, phenyl, or hexahydrocarbazole, or benzene, formed by combination with adjacent groups, indene, cyclohexane, benzofuran, or benzothiophene.

[0211] According to one embodiment of this specification, T1 to T4 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, diphenylamino (substituted or unsubstituted with tert-butyl), diphenylamino, dinaphthylamino, phenyl, or hexahydrocarbazole (substituted or unsubstituted with methyl), or is combined with adjacent groups to form benzene, indene (substituted or unsubstituted with methyl), cyclohexane (substituted or unsubstituted with methyl), benzofuran, or benzothiophene.

[0212] According to one embodiment of this specification, Y1 to Y4 may be the same as or different from each other, and each is independently hydrogen, deuterium, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 substituted or unsubstituted carbon atoms, an aromatic hydrocarbon ring with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic monocyclic or polycyclic ring with 2 to 30 substituted or unsubstituted carbon atoms.

[0213] According to one embodiment of this specification, Y1 to Y4 may be the same as or different from each other, and each independently comprises hydrogen, deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is substituted or unsubstituted by any one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an aromatic hydrocarbon ring having 6 to 30 carbon atoms that is substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

[0214] According to one embodiment of this specification, Y1 to Y4 may be the same as or different from each other, and each is independently hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, or a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a phenyl group combined with adjacent groups to form benzene; indene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; cyclohexane substituted or unsubstituted with any one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzofuran; or benzothiophene.

[0215] According to one embodiment of this specification, Y1 to Y4 may be the same as or different from each other, and each independently is hydrogen, deuterium, methyl, isopropyl, tert-butyl, cyclohexyl, or a phenyl group substituted or unsubstituted with tert-butyl, or is combined with adjacent groups to form benzene, indene substituted or unsubstituted with methyl, cyclohexane substituted or unsubstituted with one or more of methyl and phenyl groups, benzofuran, or benzothiophene.

[0216] According to one embodiment of this specification, X1 is 0.

[0217] According to one embodiment of this specification, X1 is S.

[0218] According to one embodiment of this specification, X2 is 0.

[0219] According to one embodiment of this specification, X2 is S.

[0220] According to one embodiment of this specification, A11 and A21 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms that has been substituted or unsubstituted, a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 carbon atoms that has been substituted or unsubstituted, or a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms.

[0221] According to one embodiment of this specification, A11 and A21 may be the same as or different from each other, and each independently consists of a monocyclic or polycyclic aliphatic hydrocarbon ring of 3 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group of 1 to 30 carbon atoms, an aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group of 1 to 30 carbon atoms, or a fused ring consisting of an aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group of 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring of 3 to 30 carbon atoms.

[0222] According to one embodiment of this specification, A11 and A21 may be the same as or different from each other, and each independently consists of cyclohexane substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, benzene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0223] According to one embodiment of this specification, A11 and A21 may be the same as or different from each other, and each independently is cyclohexane substituted with or unsubstituted with methyl; benzene substituted with or unsubstituted with deuterium, or tert-butyl; or tetrahydronaphthalene substituted with or unsubstituted with methyl.

[0224] According to one embodiment of this specification, the above-mentioned chemical formula 1 is selected from any of the following compounds.

[0225]

[0226]

[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] In this specification, the triplet energy can be determined using methods known in the art; specifically, it was determined using a commercially available device, the F-4500 (manufactured by Hitachi), at 77 K. The determination of the triplet energy was performed as follows: First, a sample was prepared by sealing a solution of the compound to be tested dissolved in a suitable solvent into a quartz glass tube. The phosphorescence spectrum of this sample was measured at low temperature (77 K) (vertical axis: phosphorescence intensity, horizontal axis: wavelength). A tangent was drawn at the beginning of the short-wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. 边 Substituting (nm) into the following conversion formula, the triplet energy was calculated.

[0274] Conversion formula: E T1 (eV)=1239.85 / λ 边

[0275] In this specification, the singlet energy can be determined using methods known in the art, specifically, by preparing the compound to be tested at 1 x 10⁻⁶ kilometres per ... -5 A mol / L toluene solution was placed in a quartz dish, and the absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). A tangent line was plotted on the longer wavelength side of the absorption spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis was determined. 边 Substitute (nm) into the following conversion formula to calculate the singlet energy.

[0276] Conversion formula: E S1 (eV)=1239.85 / λ 边

[0277] Specifically, after optimizing the ground state structure using density functional theory (DFT) calculations, the energies of the excited states were then calculated using transient-density functional theory (TD-DFT) to determine the singlet and triplet excitation energies. In this case, PBE0 was used as the functional and 6-31G* was used as the basis functions.

[0278] In this specification, an energy level refers to the magnitude of energy. Therefore, when an energy level is represented from the vacuum level towards the negative (-) direction, the energy level is also interpreted as representing the absolute value of that energy. For example, the HOMO energy level refers to the distance from the vacuum level to the highest occupied molecular orbital. Furthermore, the LUMO energy level refers to the distance from the vacuum level to the lowest unoccupied molecular orbital.

[0279] In this specification, the HOMO level can be determined using UPS (UV photoelectron spectroscopy), which involves irradiating the thin film surface with UV light and detecting the emitted electrons to determine the ionization potential. Alternatively, the HOMO level can be determined using CV (cyclic voltammetry), where the target substance is dissolved in a solvent along with an electrolyte, and the oxidation potential is determined by voltage sweep. Furthermore, the ionization potential can be determined in the atmosphere using the PYSA (Photoemission Yield Spectrometer in Air) method with an AC-3 (RKI) instrument.

[0280] Specifically, the HOMO level in this specification was measured under atmospheric pressure using a photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3) after vacuum evaporation of the target material onto an ITO substrate to a thickness of 50 nm or more. Furthermore, the LUMO level was calculated by measuring the absorption spectrum (abs.) and photoluminescence (PL) spectrum of the aforementioned manufactured sample, and the difference between these spectra was considered as the band gap (E). g The LUMO level was calculated by subtracting the band gap difference from the HOMO level measured in AC-3.

[0281] This specification provides organic light-emitting devices that contain the compounds mentioned above.

[0282] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0283] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0284] In this specification, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering a target area. The size of the "layer" is not limited; the sizes of individual "layers" can be the same or different. According to one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0285] In this specification, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B consists of one or more layers and substances A are contained in one or more layers of multiple layers of layer B.

[0286] In this specification, the meaning of a specific substance A being contained in layer C or layer D includes all cases where it is contained in layer C or more than one layer, or in layer D or more than one layer, or in layers C or D or more than one layer respectively.

[0287] In this specification, "deuterated", "deuterated", or "deuterated" means that hydrogen at a position in the compound that can be substituted is replaced by deuterium.

[0288] In this specification, "deuterated by X%", "X% deuterated", "degree of deuteration X%", or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, the above-mentioned dibenzofuran "deuterated by 25%", "25% deuterated", "degree of deuteration 25%", or "deuteration rate 25%" means that 2 out of the 8 hydrogens at the substituted positions in the dibenzofuran are substituted with deuterium.

[0289] In this specification, the degree of deuteration can be determined by nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 It was confirmed by known methods such as H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometry).

[0290] This specification provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0291] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited to this and can include fewer organic layers.

[0292] In one embodiment of this specification, the organic layer includes a light-emitting layer comprising a compound represented by the above-described chemical formula 1.

[0293] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above chemical formula 1 as a dopant for the light-emitting layer.

[0294] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above chemical formula 1 as a blue fluorescent dopant for the light-emitting layer.

[0295] In one embodiment of this specification, the organic light-emitting device further includes one or more layers selected from the following: hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, hole blocking layer, and electron blocking layer.

[0296] In one embodiment of this specification, the light-emitting layer further comprises a host compound.

[0297] In one embodiment of this specification, the light-emitting layer further comprises a host compound in which at least one hydrogen atom at a substituted position is replaced by deuterium.

[0298] In one embodiment of this specification, when the main compound is substituted with deuterium, the substitution is 30% or more. In another embodiment, the main compound is substituted with deuterium by 40% or more. In another embodiment, the main compound is substituted with deuterium by 60% or more. In another embodiment, the main compound is substituted with deuterium by 80% or more. In yet another embodiment, the main compound is substituted with deuterium by 100%.

[0299] In one embodiment of this specification, the light-emitting layer further comprises a compound represented by the following chemical formula H.

[0300] [Chemical formula H]

[0301]

[0302] In the above chemical formula H,

[0303] L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0304] Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0305] R20 and R21 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group.

[0306] r21 is an integer from 1 to 7. When r21 is 2 or more, two or more r21s are the same or different from each other.

[0307] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded monocyclic or polycyclic arylene with 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 30 carbon atoms.

[0308] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded monocyclic or polycyclic arylene with 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene with 2 to 20 carbon atoms.

[0309] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each independently is a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted naphthylene, divalent dibenzofuranyl, or divalent dibenzothiopheneyl.

[0310] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted, or a monocyclic or polycyclic heterocyclic group with 2 to 30 carbon atoms that has been substituted or unsubstituted.

[0311] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms.

[0312] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each is independently a monocyclic to tetracyclic aryl group with 6 to 20 carbon atoms, substituted or unsubstituted, or a monocyclic to tetracyclic heterocyclic group with 6 to 20 carbon atoms.

[0313] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted ferroyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thiophene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted naphthobenzofuranyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted naphthobenzothiophene.

[0314] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently is a phenyl substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuranyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophenyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0315] In one embodiment of this specification, the Ar20 and Ar21 described above may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a terphenyl, a deuterated or unsubstituted naphthyl, a phenanthryl, a dibenzofuranyl, a naphthobenzofuranyl, a dibenzothiophenyl, or a naphthobenzothiophenyl.

[0316] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0317] In one embodiment of this specification, R200 is hydrogen, deuterium, a halogen group, a straight-chain or branched alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0318] In one embodiment of this specification, R200 is hydrogen, deuterium, fluorine, a straight-chain or branched alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 10 substituted or unsubstituted carbon atoms, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0319] In one embodiment of this specification, R200 is hydrogen, a monocyclic or polycyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0320] In one embodiment of this specification, R200 is hydrogen, a monocyclic or polycyclic aryl group with 6 to 20 substituted or unsubstituted carbon atoms, or a monocyclic or polycyclic heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms.

[0321] In one embodiment of this specification, R200 is hydrogen, an aryl group with 6 to 20 monocyclic to tetracyclic carbon atoms (substituted or unsubstituted), or a heterocyclic group with 6 to 20 monocyclic to tetracyclic carbon atoms (substituted or unsubstituted).

[0322] In one embodiment of this specification, R200 is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted beryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted naphthobenzothiopheneyl.

[0323] In one embodiment of this specification, R200 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium, or with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with deuterium, or with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0324] In one embodiment of this specification, R200 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium, phenyl or naphthyl; biphenyl; a naphthyl group substituted or unsubstituted with deuterium, phenyl or naphthyl; dibenzofuranyl; naphthobenzofuranyl; dibenzothiophenyl; or naphthobenzothiophenyl.

[0325] According to one embodiment of this specification, R201 is hydrogen.

[0326] According to one embodiment of this specification, R201 is deuterium.

[0327] In one embodiment of this specification, when the compound represented by the above chemical formula H is substituted with deuterium, more than 30% of the hydrogen at the substituted positions are substituted with deuterium. In another embodiment, more than 40% of the hydrogen at the substituted positions in the structure of the above chemical formula H is substituted with deuterium. In yet another embodiment, more than 60% of the hydrogen at the substituted positions in the structure of the above chemical formula H is substituted with deuterium.

[0328] In another embodiment, more than 80% of the hydrogen atoms at the substituted positions in the structure of the above-described chemical formula H are replaced by deuterium. In another embodiment, 100% of the hydrogen atoms at the substituted positions in the structure of the above-described chemical formula H are replaced by deuterium.

[0329] In one embodiment of this specification, the compound represented by the above chemical formula H is selected from any of the following compounds.

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349] According to one embodiment of this specification, the compound represented by the above chemical formula H can be manufactured using the following general formula 1, but is not limited thereto.

[0350] [General Formula 1]

[0351]

[0352] In the above general formula 1,

[0353] Ar1 has the same definition as -L20-Ar20 in the above chemical formula H.

[0354] Ar2 is defined the same as -L21-Ar21 of the above chemical formula H, and can be further substituted with R20 and R201 on the anthracene core of the above general formula 1.

[0355] In one embodiment of this specification, in the light-emitting layer, the compound represented by chemical formula 1 is used as a dopant, and the compound represented by chemical formula H is used as a host.

[0356] In one embodiment of this specification, when the light-emitting layer comprises a host and a dopant, the content of the dopant can be selected from 0.01 to 10 parts by weight, based on 100 parts by weight of the light-emitting layer, but is not limited thereto.

[0357] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant, and comprises the host and the dopant in a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30, and more preferably 99:1 to 90:10.

[0358] The aforementioned luminescent layer may also include a host material, which may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives or triazine derivatives, etc., can be a mixture of two or more of them, but are not limited to this.

[0359] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains one or more dopants and a host.

[0360] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains two or more mixed dopants and a host.

[0361] According to one embodiment of this specification, one or more of the two or more mixed dopants comprises the aforementioned chemical formula 1, and the main body comprises a compound represented by the aforementioned chemical formula H. One or more of the two or more mixed dopants comprises the aforementioned chemical formula 1, and the remaining dopants may be existing known dopant materials, but are not limited thereto.

[0362] According to one embodiment of this specification, one or more of the above-mentioned mixed dopants may contain the above-mentioned chemical formula 1, and the remainder may be one or more of boron-based compounds, pyrene-based compounds, and delayed fluorescence compounds that are different from the above-mentioned chemical formula 1, but are not limited thereto.

[0363] According to one embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains one or more substrates.

[0364] According to one embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains two or more mixed substrates.

[0365] According to one embodiment of this specification, one or more of the above-mentioned two or more mixed components are compounds represented by the above-mentioned chemical formula H.

[0366] According to one embodiment of this specification, the two or more mixed components described above are different from each other, and each is independently a compound represented by the above chemical formula H.

[0367] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains two mixed substrates.

[0368] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains two mixed substrates that are different from each other, and the two substrates are compounds represented by the chemical formula H.

[0369] According to one embodiment of this specification, the organic layer includes a light-emitting layer comprising a first body represented by the above chemical formula H and a second body represented by the above chemical formula H, wherein the first body and the second body are different from each other.

[0370] According to one embodiment of this specification, the first body and the second body are contained in a weight ratio of 95:5 to 5:95, preferably in a weight ratio of 70:30 to 30:70.

[0371] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains one or more host materials and dopants.

[0372] According to one embodiment of this specification, the organic layer includes a light-emitting layer, the light-emitting layer comprising one or more host compounds and dopants, the host compound comprising a compound represented by the chemical formula H, and the dopants comprising a compound represented by the chemical formula I.

[0373] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains two or more mixed substrates and dopants.

[0374] According to one embodiment of this specification, one or more of the above-mentioned two or more mixed subjects contain a compound represented by the above-mentioned chemical formula H, and the dopant contains a compound represented by the above-mentioned chemical formula 1.

[0375] In this specification, the two or more hybrid entities mentioned above are different from each other.

[0376] According to one embodiment of this specification, the organic layer includes a light-emitting layer, which contains two mixed substrates and a dopant.

[0377] According to one embodiment of this specification, the two hybrid entities are different from each other, each independently containing a compound represented by the above chemical formula H, and the dopant contains a compound represented by the above chemical formula 1.

[0378] According to one embodiment of this specification, it comprises a first body represented by the above chemical formula H, a second body represented by the above chemical formula H, and a dopant represented by the above chemical formula I, wherein the first body and the second body are different from each other.

[0379] According to one embodiment of this specification, the organic layer uses one or more host materials and one or more dopants, wherein the host material comprises a compound represented by the above chemical formula H, and the dopants comprise a compound represented by the above chemical formula 1.

[0380] According to one embodiment of this specification, the organic layer uses two or more mixed substrates and two or more mixed dopants. The two or more mixed substrates can be made of the same materials as described above, and the two or more mixed dopants can be made of the same materials as described above.

[0381] According to one embodiment of this specification, the organic layer includes a light-emitting layer, the light-emitting layer contains a dopant substance, and the dopant substance contains a compound of the above-mentioned chemical formula 1.

[0382] According to one embodiment of this specification, the light-emitting layer further comprises one or more dopants and a host. The one or more dopants may be any known dopant materials, but are not limited thereto.

[0383] According to one embodiment of this specification, the light-emitting layer further comprises one or more substrates. These one or more substrates comprise compounds represented by the chemical formula H.

[0384] According to one embodiment of this specification, the light-emitting layer further comprises two or more mixed substrates. One or more of the two or more mixed substrates comprises a compound represented by the above chemical formula H.

[0385] According to one embodiment of this specification, the light-emitting layer further comprises two or more hybrid substrates. The two hybrid substrates are different from each other, each independently comprising a compound represented by the chemical formula H.

[0386] In one embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, wherein at least one of the two or more organic layers contains a compound represented by the above chemical formula 1.

[0387] In one embodiment of this specification, the two or more organic layers mentioned above may be selected from two or more of the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a layer that performs both hole transport and hole injection, and an electron blocking layer.

[0388] In one embodiment of this specification, the organic light-emitting device may include two or more electron transport layers, but is not limited thereto.

[0389] In one embodiment of this specification, the aforementioned organic layer comprises two or more electron transport layers, and at least one of the two or more electron transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more electron transport layers, or it may be contained in each of the two or more electron transport layers.

[0390] In addition, in one embodiment of this specification, when the above-mentioned compound is contained in each of the two or more electron transport layers, the other materials besides the compound represented by the above-mentioned chemical formula 1 may be the same as or different from each other.

[0391] When the organic layer comprising the compound represented by the above chemical formula 1 is an electron transport layer, the electron transport layer may further comprise an n-type dopant. The n-type dopant may be a material known in the art, for example, a metal or a metal complex. For example, the electron transport layer comprising the compound represented by the above chemical formula 1 may further comprise LiQ (Lithium Quinolate).

[0392] In one embodiment of this specification, the aforementioned organic layer comprises two or more hole transport layers, and at least one of the two or more hole transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more hole transport layers, or may be contained in each of the two or more hole transport layers.

[0393] Furthermore, in one embodiment of this specification, when the compound represented by the above chemical formula 1 is included in each of the two or more hole transport layers, the other materials besides the compound represented by the above chemical formula 1 may be the same as or different from each other.

[0394] In one embodiment of this specification, the organic layer may include, in addition to an organic layer containing a compound represented by the above-described chemical formula 1, a hole injection layer or a hole transport layer, which contains a compound containing an arylamine group, a carbazole group, or a benzocarbazole group.

[0395] In one embodiment of this specification, the first electrode is an anode or a cathode.

[0396] In one embodiment of this specification, the second electrode is a cathode or an anode.

[0397] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0398] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0399] For example, the structure of an organic light-emitting device according to one embodiment of this specification is illustrated in... Figure 1 and 2 The above. Figure 1 and 2 Organic light-emitting devices are illustrated, but not limited to them.

[0400] Figure 1 An example is shown of an organic light-emitting device in which a substrate 1, a first electrode 2, a light-emitting layer 3, and a second electrode 4 are sequentially stacked. In the structure described above, the aforementioned compound may be included in the light-emitting layer 3.

[0401] Figure 2 An example is shown of an organic light-emitting device comprising, in sequence, a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a first electron transport layer 8, a second electron transport layer 9, an electron injection layer 10, and a second electrode 4. In the structure described above, the aforementioned compound may be included in the light-emitting layer 3.

[0402] The organic light-emitting device described in this specification, except that one or more layers of the organic material contain the aforementioned compound, i.e., the compound represented by the aforementioned chemical formula 1, can be manufactured using materials and methods known in the art.

[0403] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0404] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0405] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0406] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (International Patent Application Publication No. 2003 / 012890). However, the manufacturing method is not limited to these methods.

[0407] As the first electrode material mentioned above, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0408] As the second electrode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., are used, but are not limited to these.

[0409] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include dibenzofuran derivatives and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0410] When the aforementioned dopant material contains compounds other than those represented by the above-mentioned chemical formula 1, these include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., which have aryl amine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. Furthermore, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0411] In this specification, when the compound represented by the above chemical formula 1 is contained in an organic layer other than the light-emitting layer, or when an additional light-emitting layer is provided, the light-emitting material of the light-emitting layer is a material capable of receiving holes and electrons from the hole transport layer and the electron transport layer respectively, and combining them to emit light in the visible light region. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo[…]. Compounds of azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene and fluorene, etc., but not limited to these.

[0412] The aforementioned hole injection layer is a layer in which holes from the electrode are injected. The hole injection material is preferably a material that possesses the ability to transport holes, the effect of injecting holes from the first electrode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. Furthermore, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic layer. Specific examples of hole-injection materials include porphyrin, oligothiophene, arylamine-based organic compounds; carbazole-based organic compounds; nitrile-based organic compounds; hexanitrile hexaazabenzophenanthrene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinone, polyaniline, and polythiophene-based conductive polymers; or mixtures of two or more of the above examples, but are not limited to these.

[0413] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material capable of receiving holes from the first electrode or the hole injection layer and transferring them to the light-emitting layer, and is preferably a material with high hole mobility. Specific examples include arylamine-based organic compounds, carbazole-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0414] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a substance capable of effectively receiving electrons from the second electrode and transferring them to the light-emitting layer, preferably a substance with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, triazine derivatives, LiQ, etc., but are not limited to these. The electron transport layer can be used together with any desired first electrode material as used in the prior art. In particular, a suitable first electrode material is a common material with a low work function and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are examples, each accompanied by an aluminum or silver layer.

[0415] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, the electron injection material is one that possesses excellent electron transport capabilities, effectively injects electrons from the second electrode, and exhibits excellent electron injection performance for the light-emitting layer or light-emitting material. Furthermore, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and also possesses excellent thin-film formation capabilities. Specifically, materials such as fluorenone, anthraquinone dimethyl ether, biphenylquinone, and thiamethoxam dioxide are preferred. azole, Diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones and their derivatives, metal coordination compounds, nitrogen-containing five-membered ring derivatives, and mixtures of two or more of the above examples, but not limited to these.

[0416] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0417] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the device's lifetime and efficiency. Known materials can be used without restriction and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0418] The aforementioned hole-blocking layer prevents holes from passing through the light-emitting layer to the cathode, and it can typically be formed using the same conditions as the electron injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, etc., but not limited to these.

[0419] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0420] In one embodiment of this specification, the compound represented by the above chemical formula 1 may be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0421] The compounds described herein can also function in organic light-emitting devices, such as organic phosphorescent devices, organic solar cells, organic photoreceptors, and organic transistors, using principles similar to those applicable to organic light-emitting devices. For example, the aforementioned organic solar cell may have a structure including a cathode, an anode, and a photoactive layer disposed between the cathode and the anode, and the photoactive layer may contain the aforementioned compounds.

[0422] The organic light-emitting device described in this specification utilizes the aforementioned compound to form one or more organic layers. Alternatively, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0423] Methods of implementing the invention

[0424] Hereinafter, in order to provide a detailed description of this specification, embodiments and comparative examples will be given. However, various modifications can be made based on the embodiments and comparative examples described herein, and this should not be construed as limiting the scope of this specification to the embodiments and comparative examples detailed below. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0425] <Manufacturing Example>

[0426] Manufacturing Example 1: Synthesis of Intermediate 1-1

[0427]

[0428] 3-bromo-4-chloro-5-iodo-1,1'-biphenyl (25 g, 63.5 mmol), bis(4-(tert-butyl)phenyl)amine (17.88 g, 63.5 mmol), Pd(Pt-Bu)₂ (0.32 g, 0.6 mmol), and NaOt-Bu (9.16 g, 95.3 mmol) were dissolved in toluene (210 mL), refluxed, and stirred. At the end of the reaction, after cooling to room temperature, the reactants were transferred to a separatory funnel and extracted. The extract was dried over MgSO₄, filtered, concentrated, and purified by column chromatography to obtain intermediate 1-1 (27.46 g, 79% yield).

[0429] MS:[M+H] + =547

[0430] Manufacturing Example 2: Synthesis of Intermediates 1-2

[0431]

[0432] Intermediate 1-1 (27.46 g, 50.2 mmol), phenylboronic acid (6.12 g, 50.2 mmol), Pd(Pt-Bu)2 (0.25 g, 0.50 mmol), and K2CO3 (13.87 g, 100.40 mmol) were dissolved in toluene (170 ml) and H2O (60 ml), refluxed, and stirred. At the end of the reaction, after cooling to room temperature, the reactants were transferred to a separatory funnel and extracted. The extract was dried over MgSO4, filtered, concentrated, and purified by column chromatography to obtain intermediate 1-2 (23.49 g, 86% yield).

[0433] MS:[M+H] + =545

[0434] Manufacturing Example 3: Synthesis of Compound 1

[0435]

[0436] In a flask containing intermediate 1-2 (23.49 g, 43.2 mmol) and toluene (140 mL), under a nitrogen atmosphere and at 0 °C, a solution of tert-butyllithium pentane (69 mL) was added. After the addition, the temperature was raised to 70 °C and stirred for 3 hours. The mixture was then cooled to -40 °C, and BBr3 (21.63 g, 86.3 mmol) was added. The mixture was stirred at room temperature for 4 hours.

[0437] At the end of the reaction, Na₂S₂O₃ solution (aq. Na₂S₂O₃) and NaHCO₃ solution (aq. NaHCO₃) were added, and the reactants were transferred to a separatory funnel for extraction. The mixture was dried over MgSO₄ and filtered, concentrated, and purified by column chromatography to obtain compound 1 (12.9 g, yield 58%).

[0438] MS:[M+H] + =518

[0439] Manufacturing Example 4: Synthesis of Intermediate 2-1

[0440]

[0441] Intermediate 2-1 was obtained by using bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine instead of bis(4-(tert-butyl)phenyl)amine, except that intermediate 2-1 was obtained by the same method as that used to manufacture intermediate 1-1 in manufacturing example 1 above.

[0442] MS:[M+H] + =656

[0443] Manufacturing Example 5: Synthesis of Intermediate 2-2

[0444]

[0445] Intermediate 2-2 was obtained by using intermediate 2-1 instead of intermediate 1-1, and (4-(4a,9a-dimethyl-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)phenyl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 2-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0446] MS:[M+H] + =852

[0447] Manufacturing Example 6: Synthesis of Compound 2

[0448]

[0449] Compound 2 was obtained by using intermediate 2-2 instead of intermediate 1-2, except that the same method as that used to manufacture compound 1 in manufacturing example 3 was employed.

[0450] MS:[M+H] + =826

[0451] Manufacturing Example 7: Synthesis of Intermediate 3-1

[0452]

[0453] Intermediate 3-1 was obtained by using 3'-bromo-4'-chloro-5'-iodo-2,6-dimethyl-1,1'-biphenyl instead of 3'-bromo-4'-chloro-5'-iodo-2,6-dimethyl-1,1'-biphenyl, and 5,5,8,8-tetramethyl-N,3-diphenyl-5,6,7,8-tetrahydronaphthalen-2-amine instead of bis(4-(tert-butyl)phenyl)amine. Otherwise, intermediate 3-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0454] MS:[M+H] + =650

[0455] Manufacturing Example 8: Synthesis of Intermediate 3-2

[0456]

[0457] Intermediate 3-2 was obtained by using intermediate 3-1 instead of intermediate 1-1, and (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-yl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 3-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0458] MS:[M+H] + =813

[0459] Manufacturing Example 9: Synthesis of Compound 3

[0460]

[0461] Compound 3 was obtained by using intermediate 3-2 instead of intermediate 1-2, except that the method was the same as that used to manufacture compound 1 in manufacturing example 3 described above.

[0462] MS:[M+H] + =786

[0463] Manufacturing Example 10: Synthesis of Intermediate 4-1

[0464]

[0465] Intermediate 4-1 was obtained by using 3-bromo-4-chloro-5-iodo-1,1'-biphenyl-2',3',4',5',6'-d5 (3-bromo-4-chloro-5-iodo-1,1'-biphenyl-2',3',4',5',6'-d5) instead of 3-bromo-4-chloro-5-iodo-1,1'-biphenyl, and 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine (5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine) instead of bis(4-(tert-butyl)phenyl)amine. Otherwise, intermediate 4-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0466] MS:[M+H] + =629

[0467] Manufacturing Example 11: Synthesis of Intermediate 4-2

[0468]

[0469] Intermediate 4-2 was obtained by using intermediate 4-1 instead of intermediate 1-1, and (4-(tert-butyl)phenyl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 4-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 above.

[0470] MS:[M+H] + =682

[0471] Manufacturing Example 12: Synthesis of Compound 4

[0472]

[0473] Compound 4 was obtained by using intermediate 4-2 instead of intermediate 1-2, except that the same method as that used to manufacture compound 1 in manufacturing example 3 was employed.

[0474] MS:[M+H] + =655

[0475] Manufacturing Example 13: Synthesis of Intermediate 5-1

[0476]

[0477] Intermediate 5-1 was obtained by using 9-(3-bromo-4-chloro-5-iodophenyl)-9H-carbazole instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, and bis(9,9-dimethyl-9H-fluoren-3-yl)amine instead of bis(4-(tert-butyl)phenyl)amine. Otherwise, intermediate 5-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0478] MS:[M+H] + =757

[0479] Manufacturing Example 14: Synthesis of Intermediate 5-2

[0480]

[0481] Intermediate 5-2 was obtained by using intermediate 5-1 instead of intermediate 1-1, and (9,9-dimethyl-9H-fluoren-3-yl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 5-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0482] MS:[M+H] + =870

[0483] Manufacturing Example 15: Synthesis of Compound 5

[0484]

[0485] Compound 5 was obtained by using intermediate 5-2 instead of intermediate 1-2, except that the method was the same as that used to manufacture compound 1 in manufacturing example 3.

[0486] MS:[M+H] + =843

[0487] Manufacturing Example 16: Synthesis of Intermediate 6-1

[0488]

[0489] Intermediate 6-1 was obtained by using bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)amine instead of bis(9,9-dimethyl-9H-fluorene-3-yl)amine, except that intermediate 6-1 was obtained by the same method as that used to manufacture intermediate 5-1 in manufacturing example 13 described above.

[0490] MS:[M+H] + =745

[0491] Manufacturing Example 17: Synthesis of Intermediate 6-2

[0492]

[0493] Intermediate 6-2 was obtained by using intermediate 6-1 instead of intermediate 1-1, and (4-(bis(4-(tert-butyl)phenyl)amino)phenyl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 6-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0494] MS:[M+H] + =1021

[0495] Manufacturing Example 18: Synthesis of Compound 6

[0496]

[0497] Compound 6 was obtained by using intermediate 6-2 instead of intermediate 1-2, except that the method was the same as that used to manufacture compound 1 in manufacturing example 3.

[0498] MS:[M+H] + =995

[0499] Manufacturing Example 19: Synthesis of Intermediate 7-1

[0500]

[0501] Intermediate 7-1 was obtained by using 9-(3-bromo-4-chloro-5-iodophenyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, and bis(4-cyclohexylphenyl)amine instead of bis(4-tert-butylphenyl)amine. Otherwise, intermediate 7-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0502] MS:[M+H] + =723

[0503] Manufacturing Example 20: Synthesis of Intermediate 7-2

[0504]

[0505] Intermediate 7-2 was obtained by using intermediate 7-1 instead of intermediate 1-1, except that intermediate 7-2 was obtained by the same method as intermediate 1-2 in manufacturing example 2 described above.

[0506] MS:[M+H] + =720

[0507] Manufacturing Example 21: Synthesis of Compound 7

[0508]

[0509] Compound 7 was obtained by using intermediate 7-2 instead of intermediate 1-2, except that the method was the same as that used to manufacture compound 1 in manufacturing example 3.

[0510] MS:[M+H] + =693

[0511] Manufacturing Example 22: Synthesis of Intermediate 8-1

[0512]

[0513] Intermediate 8-1 was obtained by using N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-3-amine instead of bis(4-cyclohexylphenyl)amine, except that intermediate 8-1 was obtained by the same method as that used to manufacture intermediate 7-1 of manufacturing example 19 described above.

[0514] MS:[M+H] + =781

[0515] Manufacturing Example 23: Synthesis of Intermediate 8-2

[0516]

[0517] Intermediate 8-1 was used instead of intermediate 1-1. Otherwise, intermediate 8-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 above.

[0518] MS:[M+H] + =778

[0519] Manufacturing Example 24: Synthesis of Compound 8

[0520]

[0521] Compound 8 was obtained by using intermediate 8-2 instead of intermediate 1-2, except that the same method as that used to manufacture compound 1 in manufacturing example 3 was employed.

[0522] MS:[M+H] + =751

[0523] Manufacturing Example 25: Synthesis of Intermediate 9-1

[0524]

[0525] Intermediate 9-1 was obtained by using 3-(3-bromo-4-chloro-5-iodophenyl)dibenzo[b,d]furan instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine instead of bis(4-(tert-butyl)phenyl)amine, except that intermediate 9-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0526] MS:[M+H] + =746

[0527] Manufacturing Example 26: Synthesis of Intermediate 9-2

[0528]

[0529] Intermediate 9-2 was obtained by using intermediate 9-1 instead of intermediate 1-1, and (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid instead of phenylboronic acid. Otherwise, intermediate 9-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0530] MS:[M+H] + =853

[0531] Manufacturing Example 27: Synthesis of Compound 9

[0532]

[0533] Compound 9 was obtained by using intermediate 9-2 instead of intermediate 1-2, except that the method was the same as that used to manufacture compound 1 in manufacturing example 3.

[0534] MS:[M+H] + =826

[0535] Manufacturing Example 28: Synthesis of Intermediate 10-1

[0536]

[0537] Intermediate 10-1 was obtained by using 1-(3-bromo-4-chloro-5-iodophenyl)dibenzo[b,d]furan instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, and bis(dibenzo[b,d]thiophen-3-yl)amine instead of bis(4-(tert-butyl)phenyl)amine, except that intermediate 10-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0538] MS:[M+H] + =738

[0539] Manufacturing Example 29: Synthesis of Intermediate 10-2

[0540]

[0541] Intermediate 10-1 was used instead of intermediate 1-1. Otherwise, intermediate 10-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 above.

[0542] MS:[M+H] + =735

[0543] Manufacturing Example 30: Synthesis of Compound 10

[0544]

[0545] Compound 10 was obtained by using intermediate 10-2 instead of intermediate 1-2, otherwise by the same method as that used to manufacture compound 1 in manufacturing example 3.

[0546] MS:[M+H] + =708

[0547] Manufacturing Example 31: Synthesis of Intermediate 11-1

[0548]

[0549] Intermediate 11-1 was obtained by using 1-(3-bromo-4-chloro-5-iodophenyl)dibenzo[b,d]thiophene instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, except that intermediate 11-1 was prepared by the same method as intermediate 1-1 of Manufacturing Example 1 described above.

[0550] MS:[M+H] +=654

[0551] Manufacturing Example 32: Synthesis of Intermediate 11-2

[0552]

[0553] Intermediate 11-2 was obtained by using intermediate 11-1 instead of intermediate 1-1, and (4-(tert-butyl)phenyl)boronic acid instead of phenylboronic acid, except that intermediate 11-2 was obtained by the same method as intermediate 1-2 in manufacturing example 2 described above.

[0554] MS:[M+H] + =707

[0555] Manufacturing Example 33: Synthesis of Compound 11

[0556]

[0557] Compound 11 was obtained by using intermediate 11-2 instead of intermediate 1-2, otherwise by the same method as that used to manufacture compound 1 in manufacturing example 3.

[0558] MS:[M+H] + =680

[0559] Manufacturing Example 34: Synthesis of Intermediate 12-1

[0560]

[0561] Intermediate 12-1 was obtained by using 4-(3-bromo-4-chloro-5-iodophenyl)dibenzo[b,d]thiophene instead of 3-bromo-4-chloro-5-iodophenyl-1,1'-biphenyl, and bis(4,4,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)amine instead of bis(4,4,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)amine. Otherwise, intermediate 12-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0562] MS:[M+H] + =774

[0563] Manufacturing Example 35: Synthesis of Intermediate 12-2

[0564]

[0565] Intermediate 12-1 was used instead of intermediate 1-1, and (4,4,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)boronic acid was used instead of phenylboronic acid. Otherwise, intermediate 12-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 described above.

[0566] MS:[M+H] + =887

[0567] Manufacturing Example 36: Synthesis of Compound 12

[0568]

[0569] Compound 12 was obtained by using intermediate 12-2 instead of intermediate 1-2, otherwise by the same method as that used to manufacture compound 1 in manufacturing example 3.

[0570] MS:[M+H] + =861

[0571] Manufacturing Example 37: Synthesis of Intermediate 13-1

[0572]

[0573] Intermediate 13-1 was obtained by using N-(3-bromo-4-chloro-5-iodophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine instead of 3-bromo-4-chloro-5-iodophenyl, and di-o-tolylamine instead of bis(4-(tert-butyl)phenyl)amine. Otherwise, intermediate 13-1 was obtained by the same method as that used to manufacture intermediate 1-1 of Manufacturing Example 1 described above.

[0574] MS:[M+H] + =631

[0575] Manufacturing Example 38: Synthesis of Intermediate 13-2

[0576]

[0577] Intermediate 13-1 was used instead of intermediate 1-1. Otherwise, intermediate 13-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 above.

[0578] MS:[M+H] + =628

[0579] Manufacturing Example 39: Synthesis of Compound 13

[0580]

[0581] Compound 13 was obtained by using intermediate 13-2 instead of intermediate 1-2, otherwise by the same method as that used to manufacture compound 1 in manufacturing example 3.

[0582] MS:[M+H] + =601

[0583] Manufacturing Example 40: Synthesis of Intermediate 14-1

[0584]

[0585] Intermediate 14-1 was obtained by using 3-bromo-4-chloro-N-(4-cyclohexylphenyl)-5-iodo-N-phenylaniline instead of 3-bromo-4-chloro-5-iodo-1,1'-biphenyl, and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine instead of bis(4-(tert-butyl)phenyl)amine, except that intermediate 14-1 was prepared by the same method as intermediate 1-1 of manufacturing example 1 described above.

[0586] MS:[M+H] + =829

[0587] Manufacturing Example 41: Synthesis of Intermediate 14-2

[0588]

[0589] Intermediate 14-1 was used instead of intermediate 1-1, and phenylboronic acid was used instead of (4-(4a,9a-dimethyl-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)phenyl)boronic acid. Otherwise, intermediate 14-2 was obtained by the same method as that used to manufacture intermediate 1-2 in manufacturing example 2 above.

[0590] MS:[M+H] + =1025

[0591] Manufacturing Example 42: Synthesis of Compound 14

[0592]

[0593] Compound 14 was obtained by using intermediate 14-2 instead of intermediate 1-2, otherwise by the same method as that used to manufacture compound 1 in manufacturing example 3.

[0594] MS:[M+H] + =999

[0595] <Device Example>

[0596] Example 1-1

[0597] ITO (indium tin oxide) is used as A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0598] On the ITO transparent electrode prepared in this way, the following HI-A and LG-101 are respectively applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, the following HT-A [material missing] is applied... A hole transport layer is formed by vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole transport layer, the following HT-B [material missing] is [deposited / applied / deposited / etc.]. An electron blocking layer is formed by vacuum evaporation to a thickness of [amount missing]. Next, compound 1, serving as a blue luminescent dopant, is vacuum evaporated onto the electron blocking layer at 4 wt% of the total weight of the luminescent layer. The following BH-A, serving as the main component, is then [deposited / deposited]. A light-emitting layer is formed by vacuum evaporation to a thickness of [amount missing]. Then, on the aforementioned light-emitting layer, as a first electron transport layer, the following compound ET-A is [deposited / applied / deposited / etc.]. Vacuum evaporation is performed, followed by vacuum evaporation of ET-B and LiQ at a 1:1 weight ratio, thereby achieving... An electron transport layer is formed with a thickness of [amount missing]. LiQ is then vacuum-deposited onto this electron transport layer, and [the process continues with the following steps]. An electron-injected layer is formed by vacuum evaporation to a thickness of [amount missing]. On this electron-injected layer, [details missing]. To achieve the desired thickness, aluminum and silver are vapor-deposited in a 10:1 weight ratio, and then aluminum is deposited on top of that. The cathode is formed by vapor deposition of a certain thickness.

[0599] During the above process, the evaporation rate of organic matter is maintained. / second, aluminum at the cathode is maintained A vapor deposition rate of / second is achieved, while maintaining a vacuum level of 1×10⁻⁶ during vapor deposition. -7 ~5×10 -8 This led to the creation of organic light-emitting devices.

[0600]

[0601] Examples 1-2 to 1-28

[0602] In Examples 1-1 above, the compounds listed in Table 1 below were used to replace the host and dopant compounds of the light-emitting layer, respectively. Otherwise, organic light-emitting devices of Examples 1-2 to 1-28 were fabricated using the same method as in Examples 1-1.

[0603]

[0604] Comparative Examples 1-1 to 1-10

[0605] In Examples 1-1 above, the compounds listed in Table 1 below were used to replace the host and dopant compounds of the light-emitting layer, respectively. Otherwise, the organic light-emitting devices of Comparative Examples 1-1 to 1-10 were fabricated using the same method as in Examples 1-1.

[0606]

[0607] The application of 10 mA / cm² to the organic light-emitting devices of Examples 1-1 to 1-28 and Comparative Examples 1-1 to 1-10 was measured. 2 Voltage, efficiency, color coordinates, and the application of 20 mA / cm at current density. 2 Lifetime (T) at current density 95 The results are shown in Table 1 below. At this point, T... 95 This indicates a current density of 20 mA / cm². 2 The time required for the initial brightness to decrease to 95% when the initial brightness is set to 100%.

[0608] [Table 1]

[0609]

[0610]

[0611] In Table 1 above, Examples 1-1 to 1-28, in which compounds of Chemical Formula 1 according to an embodiment of this specification are used in the light-emitting layer, exhibit lower driving voltage, higher quantum efficiency, and longer lifetime compared to Comparative Examples 1-1 to 1-10, in which compounds of Chemical Formula 1 are used where A1 and A2 are unsubstituted benzenes and Ar1 is an unsubstituted phenyl.

[0612] This is because the excitation energy of the first triplet state of the compound represented by the above chemical formula 1 is lower, which increases the difference between the excitation energy of the first singlet state and the excitation energy of the first triplet state. Therefore, triplet quenching is suppressed, thereby increasing the device lifetime and efficiency of organic light-emitting devices containing this compound in the host-doped system.

Claims

1. A compound represented by the following chemical formula 1: ， In the chemical formula 1, A1 is a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle. A2 is a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle containing one or more of O and S. Ar1 can be a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group. At least one of R1 to R3 is a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, a substituted or unsubstituted heterocyclic group, or -NR11R12, and the remainder is hydrogen. R11 and R12 may be the same as or different from each other, and each can be independently a substituted or unsubstituted aryl group, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group. This excludes cases where A1 and A2 are unsubstituted benzene rings and Ar1 is an unsubstituted phenyl group.

2. The compound according to claim 1, wherein, At least one of the hydrogen atoms at the substituted positions in Formula 1 is replaced by deuterium.

3. The compound according to claim 1, wherein, Chemical Formula 1 is represented by the following Chemical Formulas 1-1 to 1-4: ， In the chemical formulas 1-1 to 1-4, The definitions of R1 to R3 are the same as those in Chemical Formula 1. X1 and X2 may be the same or different from each other, and each can be O or S independently. A11 is a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle. A21 is a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocycle containing one or more of O and S. Z1 to Z4, Y1 to Y5, and T1 to T4 may be the same as or different from each other, and each independently consists of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups. In the aforementioned chemical formula 1-1, the case where Z1 to Z4, Y1 to Y5, and T1 to T4 are all hydrogen is excluded.

4. The compound according to claim 1, wherein, Each of R1 to R3 is an aryl group consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted by one or more of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a combination thereof; or a fused ring consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. The radical; consisting of one or more substituted or unsubstituted monocyclic or polycyclic groups of 2 to 30 carbon atoms selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 30 carbon atoms (straight-chain or branched), alkenyl groups with 2 to 30 carbon atoms (straight-chain or branched), aryl groups with 6 to 30 carbon atoms (monocyclic or polycyclic), heterocyclic groups with 2 to 30 carbon atoms (monocyclic or polycyclic), and combinations thereof; or -NR11R12, the remainder being hydrogen. R11 and R12 may be the same as or different from each other, and each independently is an aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted by one or more of a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group with 3 to 30 carbon atoms, and combinations thereof; a fused ring group consisting of an aromatic hydrocarbon ring with 6 to 30 carbon atoms substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms; or a heterocyclic group consisting of a monocyclic or polycyclic alkyl group with 2 to 30 carbon atoms substituted or unsubstituted by an aryl group with 6 to 30 carbon atoms. The A1 is a fused ring consisting of one or more substituted or unsubstituted aromatic hydrocarbon rings consisting of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and combinations thereof; a fused ring consisting of an aromatic hydrocarbon ring consisting of a monocyclic or polycyclic alkyl group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a fused ring consisting of one or more substituted or unsubstituted monocyclic or polycyclic heterocyclic rings consisting of a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof consisting of deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms. The A2 is any one or more substituted or unsubstituted aromatic hydrocarbon rings of 6 to 30 carbon atoms selected from straight-chain or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms, monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms, and combinations thereof; A fused ring consisting of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aromatic hydrocarbon ring having 3 to 30 carbon atoms, either substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a heterocycle having 2 to 30 carbon atoms and containing one or more monocyclic or polycyclic rings selected from deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, and combinations thereof, substituted or unsubstituted with a monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms and containing one or more of O and S. The Ar1 is a fused ring group consisting of one or more substituted or unsubstituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups with 3 to 30 carbon atoms, monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms, and combinations thereof; or a heterocyclic group consisting of monocyclic or polycyclic aryl groups with 2 to 30 carbon atoms, substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms; a fused ring group consisting of a monocyclic or polycyclic aromatic hydrocarbon ring with 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring with 3 to 30 carbon atoms, selected from straight-chain or branched alkyl groups with 1 to 30 carbon atoms; or a heterocyclic group consisting of a monocyclic or polycyclic aryl group with 2 to 30 carbon atoms, substituted or unsubstituted by a straight-chain or branched alkyl group with 1 to 30 carbon atoms. This excludes cases where A1 and A2 are unsubstituted benzene rings and Ar1 is an unsubstituted phenyl group.

5. The compound according to claim 1, wherein, Chemical Formula 1 is selected from any of the following compounds: 。 6. An organic light-emitting device, comprising: The first electrode, the second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer includes a light-emitting layer, which contains the compound.

8. The organic light-emitting device according to claim 6, wherein, The organic layer includes a light-emitting layer, which contains a dopant material, the dopant material containing the compound.

9. The organic light-emitting device according to claim 6, wherein, The organic layer includes a light-emitting layer, which contains a compound represented by the chemical formula H: ， In the chemical formula H, L20 and L21 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar20 and Ar21 may be the same as or different from each other, and each can be independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic. R200 and R201 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group. r201 is an integer from 1 to 7. When r201 is 2 or more, two or more R201s are the same or different from each other.

10. The organic light-emitting device according to claim 8, wherein, The luminescent layer also comprises a host compound in which at least one hydrogen atom at a substituted position is replaced by deuterium.

11. The organic light-emitting device according to claim 8, wherein, The light-emitting layer also contains one or more dopants and a host.

12. The organic light-emitting device according to claim 8, wherein, The light-emitting layer also includes one or more main components.

13. The organic light-emitting device according to claim 8, wherein, The light-emitting layer also contains two or more hybrid entities.

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