Organic light-emitting device including organic compound

Abstract

The present specification provides an organic light-emitting device including an emitting layer containing a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula H. Specifically, the present invention provides an organic light-emitting device including an anode, a cathode, and an organic material layer provided between the anode and the cathode, the organic material layer including an emitting layer, the emitting layer including a compound represented by Chemical Formula 1 below and a compound represented by Chemical Formula H below. The organic light-emitting device has high color purity, high efficiency, and / or long life.

Description

[Technical field]

[0001] The present specification relates to a compound and an organic light-emitting device containing the same.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0183776 filed with the Korean Intellectual Property Office on December 24, 2020, and Korean Patent Application No. 10-2021-0078534 filed with the Korean Intellectual Property Office on June 17, 2021, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] In general, organic light-emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. Organic light-emitting devices that utilize organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light-emitting device structure, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the bottom state again, light is emitted.

[0004] There is a demand for the development of new materials for such organic light-emitting devices. Among them, in the case of blue organic light-emitting devices, high color purity and long life characteristics are essential, but there is a lack of technology to realize both at the same time due to instability caused by the high energy of blue materials. In recent years, thermally activated delayed fluorescent materials having a core structure containing boron have been newly developed and have attracted attention for their high efficiency and color purity, but they have drawbacks such as high triplet energy, slow reverse intersystem crossing speed, and short life. Therefore, there is a demand for the development of blue organic light-emitting materials that simultaneously realize high color purity and long life characteristics. Summary of the Invention [Problem to be solved by the invention]

[0005] The present specification provides an organic light emitting device that includes an organic compound. [Means for solving the problem]

[0006] One embodiment of the present disclosure includes an organic layer comprising an anode; a cathode; and an organic layer disposed between the anode and the cathode, the organic layer includes a light-emitting layer, The light-emitting layer includes a compound represented by the following Chemical Formula 1; and a compound represented by the following Chemical Formula H.

[0007] [Chemical formula 1] [ka] In the above Chemical Formula 1, A1 is any one of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted heterocycle, and condensed rings thereof; R5 to R8 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is combined with A1 to form a substituted or unsubstituted ring; Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is combined with R5 to form a substituted or unsubstituted ring; when Ar2 and R5 form a benzoxazine ring, the benzoxazine ring is an unsubstituted benzoxazine ring; Z1 to Z3 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or Z1 to Z3 are bonded to each other with adjacent groups to form a substituted or unsubstituted ring, when Ar1 is a phenyl group, A1 is a substituted or unsubstituted benzene, R6 to R8 are hydrogen, adjacent groups among Z1 to Z3 are not bonded to form a substituted or unsubstituted ring, and Ar2 and R5 simultaneously form an indole ring, the indole ring is a substituted indole ring, [Chemical formula H] [ka] In the above formula H, L20 and L21 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; Ar20 and Ar21 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; At least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group; R200 and R201 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r201 is an integer of 1 to 7, and when r201 is 2 or more, the 2 or more R201's are the same or different from each other. Effect of the Invention

[0008] The organic light-emitting device according to an embodiment of the present specification includes a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula H as light-emitting layer materials, and has high color purity, high efficiency and / or long life characteristics. [Brief description of the drawings]

[0009] [Figure 1] 1 illustrates an organic light emitting device according to one embodiment of the present disclosure. [Explanation of symbols]

[0010] 1. Circuit board 2. Anode 3. Emitting layer 4 ··· Cathode DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The present specification will be explained in further detail below.

[0012] The present specification provides an organic light-emitting device including a light-emitting layer containing a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula H. Specifically, the organic light-emitting device contains the compound represented by Chemical Formula 1 as a dopant and the compound represented by Chemical Formula H as a host.

[0013] Organic light-emitting devices using conventional boron-based compounds have higher efficiency than organic light-emitting devices using pyrene-based compounds, but have the disadvantage of a short lifespan. However, the compound represented by Chemical Formula 1 has a narrow half-width, and organic light-emitting devices containing this have the advantage of increased efficiency and lifespan. The narrow half-width is maintained by the hexagonal ring of boron and amine, but the direct bond between boron and amine on the opposite side fills the missing electrons of boron, increasing the stability of the core in the unstable polaron state, increasing the lifespan, and the transition of polarons to exciton states is successfully promoted, increasing the efficiency of organic light-emitting devices containing them.

[0014] The compound represented by the formula H has good hole and electron transfer and injection, stable driving voltage, and high light emission quantum yield, and therefore has long life and high efficiency when used as a host in the light emitting layer of an organic light emitting device.

[0015] Throughout this specification, the term "combinations thereof" contained in a Markush form expression means a mixture or combination of one or more selected from the group of elements set forth in the Markush form expression, including at least one selected from the group of elements.

[0016] Examples of the substituents in this specification are described below, but are not limited to them.

[0017] In this specification, dotted lines or [ka] means the site to be linked.

[0018] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is replaced, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0019] As used herein, the term "substituted or unsubstituted" means substituted with at least one substituent selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; an alkylaryl group; a silyl group; a boron group; an amine group; an aryl group; a heterocyclic group; and a fused hydrocarbon ring group, or substituted with a substituent in which two or more of the substituents exemplified above are linked, or having no substituent at all.

[0020] In the present specification, the term "two or more substituents are linked" refers to the fact that a hydrogen atom of any one of the substituents is linked to another substituent. For example, two substituents are linked when a phenyl group and a naphthyl group are linked. [ka] In addition, the linkage of three substituents includes not only the linkage of (substituent 1)-(substituent 2)-(substituent 3) in succession, but also the linkage of (substituent 1) to (substituent 2) and (substituent 3). For example, the linkage of a phenyl group, a naphthyl group, and an isopropyl group results in [ka] The above definitions also apply to those in which four or more substituents are linked.

[0021] In this specification, the term "substituted with A1 or A2" includes not only the case where it is substituted with A1 or the case where it is substituted with A2, but also the case where it is substituted with A1 and A2.

[0022] In one embodiment of the present specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkylthioxy group; arylthioxy group; alkenyl group; haloalkyl group; haloalkoxy group; arylalkyl group; alkylaryl group, silyl group; boron group; amine group; aryl group; heterocyclic group; and fused hydrocarbon ring group, or is substituted with a substituent in which two or more of the above-mentioned substituents are linked, or has no substituents at all,

[0023] The alkyl group has 1 to 20 carbon atoms, the cycloalkyl group has 3 to 60 carbon atoms, the aryl group has 6 to 60 carbon atoms, the heterocyclic group has 2 to 60 carbon atoms, the heterocyclic group contains at least one of O, S, N and Si as a hetero element, and the fused hydrocarbon ring group has 9 to 90 carbon atoms.

[0024] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0025] In this specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, and more preferably 1 to 15, 1 to 10, or 1 to 6 carbon atoms. Specific examples include, but are not limited to, 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0026] As used herein, t-Bu refers to a tert-butyl group.

[0027] In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. The cycloalkyl group may be a monocyclic ring or a polycyclic ring having two or more rings. Specific examples of the cycloalkyl group include, but are not limited to, 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 group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.1]octyl group, and norbornyl group.

[0028] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30, more preferably 1 to 15, 1 to 10, or 1 to 6. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like.

[0029] In this specification, the alkenyl group may be linear 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, a stilbenyl group, and a styrenyl group, but are not limited thereto.

[0030] In this specification, the term "haloalkyl group" refers to an alkyl group defined above in which at least one halogen group is substituted for hydrogen.

[0031] In this specification, the term "haloalkoxy group" refers to an alkoxy group defined above in which at least one halogen group is substituted for a hydrogen atom of the alkoxy group.

[0032] In this specification, the aryl group is not particularly limited, but may have a carbon number of 6 to 50, preferably a carbon number of 6 to 30, and more preferably a carbon number of 6 to 20. The aryl group may be monocyclic or polycyclic.

[0033] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 6 to 30, and more preferably 6 to 20. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

[0034] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 10 to 30, and more preferably 10 to 20. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, and a fluorene group.

[0035] As used herein, the fluorene group may be substituted and adjacent groups may be linked to each other to form a ring.

[0036] When the fluorene group is substituted, [ka] These include, but are not limited to:

[0037] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon on an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0038] In this specification, the arylalkyl group means that the alkyl group is substituted with an aryl group, and the above-mentioned examples of the aryl group and alkyl group can be applied to the aryl group and the alkyl group of the arylalkyl group.

[0039] In this specification, the aryloxy group means that the alkyl group of the alkoxy group is replaced with an aryl group, and the above description of the aryl group can be applied. The aryloxy group includes, but is not limited to, a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group.

[0040] In this specification, the alkyl group of the alkylthioxy group is the same as the above-mentioned alkyl group. Specifically, the alkylthioxy group includes, but is not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group.

[0041] In this specification, the aryl group in the arylthioxy group is the same as the above-mentioned examples of the aryl group.Specific examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

[0042] In the present specification, the heterocyclic group includes one or more atoms other than carbon, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of N, O, S, Si, and Se, and includes an aromatic heterocyclic group or an aliphatic heterocyclic group. 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 may be 2 to 60, preferably 2 to 30, and more preferably 2 to 20, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a naphthobenzofuran group, a naphthobenzothiophene group, a dibenzosilole group, a naphthobenzosilole group, a phenanthridine group ( phenanthridine, phenanthroline, isoxazole, thiadiazole, dibenzofuran, dibenzosilole, phenoxathiine, phenoxazine, phenothiazine, decahydrobenzocarbazole, hexahydrocarbazole, dihydrobenzoazasiline, dihydroindenocarbazole, spirofluorenexanthene, spirofluorenethioxanthene, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran groups, but are not limited to these.

[0043] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the above-mentioned exemplified alkyl group, the aryl group in the arylsilyl group may be the above-mentioned exemplified aryl group, the alkyl group and the aryl group in the alkylarylsilyl group may be the above-mentioned exemplified alkyl group and the heteroaryl group in the heteroarylsilyl group may be the above-mentioned exemplified heterocyclic group.

[0044] As used herein, the boron group is -BR 100 R 101 wherein R 100 and R 101 are the same or different and may each be independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Specific examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, and a diphenyl boron group.

[0045] In the present specification, the amine group can be selected from the group consisting of -NH2; alkylamine group; alkylarylamine group; arylamine group; arylheteroarylamine group; alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In the case of an arylamine group, the number of carbon atoms is 6 to 60. According to another embodiment, the number of carbon atoms of the arylamine group is 6 to 40. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, and an N-naphthylfluorenylamine group. group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group; N-(4-(tert-butyl)phenyl)-N-phenylamine group; N,N-bis(4-(tert-butyl)phenyl)amine group; and N,N-bis(3-(tert-butyl)phenyl)amine group, but are not limited thereto.

[0046] In the present specification, the term "N-alkylarylamine group" refers to an amine group in which an alkyl group and an aryl group are substituted at the N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the above-mentioned examples of the alkyl group and the aryl group.

[0047] In the present specification, the term "N-arylheteroarylamine group" refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the above-mentioned examples of the aryl group and the heterocyclic group.

[0048] In the present specification, the term "N-alkylheteroarylamine group" refers to an amine group in which an alkyl group and a heteroaryl group are substituted at the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the alkyl group and the heterocyclic group exemplified above.

[0049] In this specification, the alkylamine group refers to an amine group in which an alkyl group is substituted at the N of the amine group, and includes a dialkylamine group, an alkylarylamine group, and an alkylheteroarylamine group.

[0050] In this specification, the term "arylamine group" refers to an amine group in which an aryl group is substituted at the N atom of the amine group, and includes a diarylamine group, an arylheteroarylamine group, and an alkylarylamine group.

[0051] In this specification, the term "heteroarylamine group" refers to an amine group in which a heteroaryl group is substituted at the N of the amine group, and includes a diheteroarylamine group, an arylheteroarylamine group, and an alkylheteroarylamine group.

[0052] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the above-mentioned exemplified cycloalkyl group, aryl group, and combinations thereof. Examples of the hydrocarbon ring group include, but are not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, and a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group.

[0053] In this specification, the meaning of "adjacent" in "bonding with adjacent groups to form a ring" is the same as defined above, and the "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0054] In this specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the exemplified cycloalkyl groups, aryl groups, and combinations thereof, except that it is not monovalent. Examples of the hydrocarbon ring include, but are not limited to, benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methanonaphthalene, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.

[0055] The aliphatic hydrocarbon ring includes all of the rings of a single bond, a non-aromatic multiple bond-containing hydrocarbon ring, and a ring in which a single bond and a multiple bond are condensed. Therefore, the ring of a single bond in the aliphatic hydrocarbon ring may be selected from the examples of the cycloalkyl group, except that it is not a monovalent group, and the hydrocarbon rings of cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclonorbornene, etc. that include a single bond and a double bond but are not aromatic rings also belong to the aliphatic hydrocarbon ring.

[0056] In this specification, the term "condensed hydrocarbon ring (group)" refers to a condensed ring (group) of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and the above explanation of the aryl group can be applied to the aromatic hydrocarbon ring, and the above explanation of the cycloalkyl group can be applied to the aliphatic hydrocarbon ring. The condensed hydrocarbon ring (group) has 9 to 90 carbon atoms, preferably 9 to 60 carbon atoms, and more preferably 9 to 30 carbon atoms.

[0057] In the present specification, a heterocycle includes one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may be one or more atoms selected from the group consisting of N, O, S, Si, Se, etc. The heterocycle may be a monocycle or a polycycle, and may be an aromatic heterocycle; an aliphatic heterocycle; a condensed ring of an aromatic heterocycle and an aliphatic heterocycle; a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic group, or a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aliphatic heterocyclic group, and the aromatic heterocycle may be selected from the examples of the heteroaryl group in the heterocyclic group, except that the aromatic heterocycle is not monovalent.

[0058] In this specification, the term "aliphatic heterocycle" refers to an aliphatic ring containing at least one heteroatom. The term "aliphatic heterocycle" includes any of aliphatic rings with a single bond, aliphatic rings with multiple bonds, and aliphatic rings in which a ring containing a single bond and a ring containing multiple bonds is condensed. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

[0059] As used herein, "deuterated," "substituted with deuterium," or "deuterated" means that a hydrogen atom at a substitutable position of a compound is replaced with a deuterium atom.

[0060] As used herein, "X% substitution with deuterium", "X% deuterated", "degree of deuteration X%" or "deuterium substitution rate X%" means that X% of hydrogen atoms at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, "25% substitution with deuterium" of the dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that two of eight hydrogen atoms at substitutable positions in the dibenzofuran are replaced with deuterium.

[0061] In this specification, the degree of deuteration is measured by nuclear magnetic resonance spectroscopy ( 1 The identity of the compound can be confirmed by known methods such as 1 H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix assisted laser desorption / ionization Time-of-Flight Mass Spectrometry).

[0062] In this specification, when we say that a member is located "on" another member, this includes not only when the member is in contact with the other member, but also when there is another member between the two members.

[0063] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless specifically stated to the contrary.

[0064] In this specification, the term "layer" is interchangeable with the term "film" commonly used in the art, and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may be the same or different in size. According to one embodiment, the size of the "layer" may be the same as the entire element, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0065] In this specification, the term "a specific substance A is contained in layer B" means both i) one or more types of substance A are contained in one layer B, and ii) layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layer B.

[0066] In this specification, when a specific substance A is contained in layer C or layer D, it means that i) it is contained in one or more of one or more C layers, ii) it is contained in one or more of one or more D layers, or iii) it is contained in one or more C layers and one or more D layers.

[0067] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. Methods and materials similar or equivalent to those described herein may be used to carry out or test embodiments of the present invention, and suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will take precedence unless a specific passage is mentioned. In addition, the materials, methods, and examples are merely illustrative and are not intended to be limiting.

[0068] Chemical formula 1 will now be described in detail.

[0069] [Chemical formula 1] [ka] In the above Chemical Formula 1, A1 is any one of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted heterocycle, and condensed rings thereof; R5 to R8 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is combined with A1 to form a substituted or unsubstituted ring; Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is combined with R5 to form a substituted or unsubstituted ring; when Ar2 and R5 form a benzoxazine ring, the benzoxazine ring is an unsubstituted benzoxazine ring; Z1 to Z3 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or Z1 to Z3 are bonded to each other with adjacent groups to form a substituted or unsubstituted ring, When Ar1 is a phenyl group, A1 is a substituted or unsubstituted benzene, R6 to R8 are hydrogen, adjacent groups among Z1 to Z3 are not bonded to form a substituted or unsubstituted ring, and Ar2 and R5 simultaneously form an indole ring, the indole ring is a substituted indole ring.

[0070] According to one embodiment of the present specification, at least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring, and the remainder is hydrogen.

[0071] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or is bonded to A1 to form any one of a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, and fused rings thereof, which contains at least one of N, S, O, and Si.

[0072] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or is bonded to R5 to form any one of an aromatic heterocycle, an aliphatic heterocycle, and a fused ring thereof, which are substituted or unsubstituted and contain one or more of N, S, O, and Si.

[0073] According to one embodiment of the present specification, the formula 1 is represented by the following formula 1-1. [Chemical formula 1-1] [ka] In the above Chemical Formula 1-1, R5 to R8, Ar2, and Z1 to Z3 are defined as those in Chemical Formula 1. R1 to R4 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form any one of a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted heterocycle; and a condensed ring thereof; Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is combined with R4 to form a substituted or unsubstituted ring; When Ar1 is a phenyl group, R1 to R4 and R6 to R8 are hydrogen, adjacent groups among Z1 to Z3 are not bonded to form a substituted or unsubstituted ring, and Ar2 and R5 simultaneously form an indole ring, the indole ring is a substituted indole ring.

[0074] According to one embodiment of the present specification, the formula 1 is represented by the following formula 1-2. [Chemical formula 1-2] [ka] In the above Chemical Formula 1-2, R5 to R8, Ar2, and Z1 to Z3 are defined as those in Chemical Formula 1. X1 is CRR'; O; or S; A11 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; R and R' are the same or different and each independently represent a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are joined to each other to form a substituted or unsubstituted ring.

[0075] According to one embodiment of the present specification, the chemical formula 1-1 is represented by any one of the following chemical formulas 1-1-1 to 1-1-36. [Chemical formula 1-1-1] [ka] [Chemical formula 1-1-2] [ka] [Chemical formula 1-1-3] [ka] [Chemical formula 1-1-4] [ka] [Chemical formula 1-1-5] [ka] [Chemical formula 1-1-6] [ka] [Chemical formula 1-1-7] [ka] [Chemical formula 1-1-8]

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[0076] In the above Chemical Formulas 1-1-1 to 1-1-36, X2 to X9 are the same or different and each independently represents CRR'; NR''; O; or S; Y1 and Y2 are the same or different and each independently represents CG1G2; SiG8G9; NG101; O; or S; y1 is 0 or 1, and when y1 is 0, Y1 is a direct bond; y2 is 0 or 1, and when y2 is 0, Y2 is a direct bond; R, R' and R'' are the same or different and each independently represent a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are joined together to form a substituted or unsubstituted ring; R'1 to R'8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; G1 to G19, G'13 and G101 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, g3, g7, and g15 to g18 are each an integer of 1 to 4; g4 and g10 each represent an integer of 1 to 8; g13 and g14 are each 1 or 2; g'13 is an integer from 0 to 2, g19 is an integer from 1 to 3; a21 is 0 or 1, When g3, g4, g7, g10, and g15 to g19 each are 2 or more, the substituents in the 2 or more brackets are the same or different from each other, When g13, g'13 and g14 are each 2, the substituents in the two brackets are the same or different from each other, Ar'1 and Ar'2 are the same or different and each independently represents a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; A2 and A21 are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Z1 to Z3 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or Z1 to Z3 are bonded to each other with adjacent groups to form a substituted or unsubstituted ring, In the above chemical formulas 1-1-4, 1-1-6, 1-1-8, 1-1-12, 1-1-28 and 1-1-32, When y2 is 1 and Y2 is O, G7 and R'6 to R'8 are hydrogen.

[0077] In one embodiment of the present specification, at least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring, and the remainder is hydrogen.

[0078] According to one embodiment of the present specification, the chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-6.

[0079] [Chemical formula 1-2-1] [ka] [Chemical formula 1-2-2] [ka] [Chemical formula 1-2-3] [ka] [Chemical formula 1-2-4] [ka] [Chemical formula 1-2-5] [ka] [Chemical formula 1-2-6] [ka]

[0080] In the above Chemical Formulas 1-2-1 to 1-2-6, The definitions of X1, A11, and Z1 to Z3 are the same as those defined in Chemical Formula 1-2. X3 to X6 are the same or different and each independently represents CRR'; NR''; O or S; Y2 is CG1G2;SiG8G9;NG101;O; or S; y2 is 0 or 1, and when y2 is 0, Y2 is a direct bond; A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; R, R' and R'' are the same or different and each independently represent a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are joined together to form a substituted or unsubstituted ring; R'5 to R'8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; G1, G2, G7 to G12, G14, G15, G16 and G101 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine 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, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, g7, g15, and g16 are each an integer of 1 to 4; g10 is an integer from 1 to 8; g14 is 1 or 2, When g7, g10, g15 and g16 each are 2 or more, the two or more substituents in the parentheses are the same or different from each other, When g14 is 2, the substituents in the two brackets are the same or different from each other, Ar'1 and Ar'2 are the same or different and each independently represent a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group. According to one embodiment of the present specification, in the above-mentioned Chemical Formula 1-1-4, Y2 is CG1G2;SiG8G9;NG101;O; or S, y2 is 0 or 1; When y2 is 0, Y2 is a direct bond; R'1 to R'4 and R'6 to R'8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; G7 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, and g7 is an integer of 1 to 4, Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; Z1 to Z3 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; In the above Chemical Formula 1-2-2, When y2 is 1 and Y2 is O, G7 and R'6 to R'8 are hydrogen.

[0081] According to one embodiment of the present specification, at least one of Z1 to Z3 is deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine 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.

[0082] According to one embodiment of the present specification, in the case of the above formula 1-1-4, the case where the substituents are bonded to each other to form a substituted or unsubstituted ring is excluded.

[0083] According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-5.

[0084] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka] In the above Chemical Formulas 1-3 to 1-5, The definitions of Ar1, Ar2, A1, R5 to R8, and Z1 to Z3 are the same as those defined in Chemical Formula 1. T1 to T10 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring, At least one of T1 and T2 is a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; At least one of T6 and T7 is a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group.

[0085] In one embodiment of the present specification, at least one of T1 and T2 is a substituent that is not hydrogen.

[0086] In one embodiment of the present specification, at least one of T6 and T7 is a non-hydrogen substituent.

[0087] According to one embodiment of the present specification, Formula 1 is represented by Formula 2 below.

[0088] [Chemical formula 2] [ka] In the above Chemical Formula 2, The definitions of A1, Ar1, and Z1 to Z3 are the same as those defined in Chemical Formula 1. Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and a fused ring group of an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to R''51 to form any one of an aromatic heterocycle, an aliphatic heterocycle, and a fused ring thereof, which is substituted or unsubstituted and contains one or more of N, S, O, and Si; R''51 and R''5 to R''8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring; r''51 is 1 or 2, When r''51 is 2, the two R''51 are the same or different. According to one embodiment of the present specification, the formula 1-1 is represented by the following formula 2-1.

[0089] [Chemical formula 2-1] [ka] In the above Chemical Formula 2-1, The definitions of Ar1, R1 to R4, and Z1 to Z3 are the same as those defined in Chemical Formula 1-1. Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and a fused ring group of an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to R''51 to form any one of an aromatic heterocycle, an aliphatic heterocycle, and a fused ring thereof, which is substituted or unsubstituted and contains one or more of N, S, O, and Si; R''51 and R''5 to R''8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring; r''51 is 1 or 2, When r''51 is 2, the two R''51 are the same or different.

[0090] According to one embodiment of the present specification, the formula 1-2 is represented by the following formula 2-2. [Chemical formula 2-2] [ka] The definitions of X1, A11, Ar′1, and Z1 to Z3 are the same as those defined in Chemical Formula 1-2. Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aromatic hydrocarbon ring and a fused ring group of an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to R''51 to form any one of an aromatic heterocycle, an aliphatic heterocycle, and a fused ring thereof, which is substituted or unsubstituted and contains one or more of N, S, O, and Si; R''51 and R''5 to R''8 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring; r''51 is 1 or 2, When r''51 is 2, the two R''51 are the same or different.

[0091] According to one embodiment of the present specification, adjacent groups among Z1 to Z3 are bonded to each other to form a ring represented by the following chemical formula C-1 or C-2. [Chemical formula C-1] [ka] [Chemical formula C-2] [ka] In the above chemical formulas C-1 and C-2, J1 is O;S;NQ7;CQ8Q9; or SiQ10Q11; W1 to W8 and Q7 to Q11 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring; * denotes a site for binding to Chemical Formula 1.

[0092] Among the above Z1 to Z3, the adjacent groups refer to Z1 and Z2; or Z2 and Z3.

[0093] According to one embodiment of the present specification, adjacent groups among W1 to W8 are bonded to each other to form a ring represented by the chemical formula C-1.

[0094] According to one embodiment of the present specification, the formula C-2 is any one selected from the following structures: [ka] In the above structure, *, W1 to W8, and Q7 to Q11 are defined as above.

[0095] According to one embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a fused ring of a substituted or unsubstituted 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 heterocycle having 2 to 30 carbon atoms.

[0096] According to one embodiment of the present specification, A1 is a linear or branched alkyl group having 1 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with NQ1Q2; a fused ring 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0097] According to one embodiment of the present specification, A1 is a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a fused ring group of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a benzene substituted or unsubstituted with NQ1Q2; naphthalene; indene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Fluorene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthalene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; dibenzothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; benzofuran substituted or unsubstituted with 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; Benzothiophenes substituted or unsubstituted with straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms, or monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms;benzonaphthofuran;naphthofuran;benzonaphthothiophenes substituted or unsubstituted with straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms;tetrahydrobenzonaphthofuran substituted or unsubstituted with straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms;tetrahydrobenzonaphthothiophenes ... tetrahydrobenzofluorene 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; tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; naphthothiophene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or tetrahydrobenzoindene substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0098] According to one embodiment of the present specification, A1 is selected from the group consisting of benzene substituted or unsubstituted with a methyl group, a tert-butyl group, a tetramethyltetrahydronaphthyl group, a phenyl group, and NQ1Q2; naphthalene; indene substituted or unsubstituted with a methyl group; fluorene substituted or unsubstituted with a methyl group; tetrahydronaphthalene substituted or unsubstituted with a methyl group; dibenzofuran substituted or unsubstituted with a methyl group or a tert-butyl group; dibenzothiophene substituted or unsubstituted with a methyl group or a tert-butyl group; benzofuran substituted or unsubstituted with a methyl group, a phenyl group, or a tert-butyl group; a methyl group, a phenyl group, or benzothiophene substituted or unsubstituted with a tert-butyl group; benzonaphthofuran; naphthofuran; benzonaphthothiophene substituted or unsubstituted with a tert-butyl group; tetrahydrobenzonaphthofuran substituted or unsubstituted with a methyl group; tetrahydrobenzonaphthothiophene substituted or unsubstituted with a methyl group; tetrahydrobenzofluorene substituted or unsubstituted with a methyl group; tetrahydronaphthofuran substituted or unsubstituted with a methyl group; tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; naphthothiophene substituted or unsubstituted with a methyl group; or tetrahydrobenzoindene substituted or unsubstituted with a methyl group.

[0099] According to one embodiment of the present specification, Q1 and Q2 are the same or different and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 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, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0100] According to one embodiment of the present specification, Q1 and Q2 are the same or different, and each independently represents a methyl group; a tert-butyl group; a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a biphenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a fluorene group substituted or unsubstituted with a methyl group; a tetrahydronaphthyl group substituted or unsubstituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.

[0101] According to one embodiment of the present specification, R5 to R8 are the same or different from each other and each independently represent hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or are bonded to adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a condensed ring of a substituted or unsubstituted 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 heterocycle having 2 to 30 carbon atoms.

[0102] According to one embodiment of the present specification, R5 to R8 are the same or different and each independently represent hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a linear or branched alkyl group having 1 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms. a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with a linear 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 monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0103] According to one embodiment of the present specification, R5 to R8 are the same or different and each independently represent hydrogen; deuterium; a methyl group; a tert-butyl group; a phenyl group, or NQ3Q4, or are bonded to adjacent groups to represent cyclohexane substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzene; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic diazonium ring having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms. Benzofurans substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthofuran; naphthothiophene; monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms Indenes substituted or unsubstituted with amine groups;Indoles substituted or unsubstituted with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms;Indoloindenes substituted or unsubstituted with linear or branched alkyl groups having 1 to 30 carbon atoms;Indoloindoles;Tetrahydronaphthofurans substituted or unsubstituted with linear or branched alkyl groups having 1 to 30 carbon atoms;Tetrahydronaphthothiophenes substituted or unsubstituted with linear or branched alkyl groups having 1 to 30 carbon atoms;Straight-chain or branched alkyl groups having 1 to 30 carbon atoms. benzodioxine; benzooxathiine; benzodithiine; thiochromene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; chromene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or dihydronaphthalene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0104] According to one embodiment of the present specification, R5 to R8 are the same or different from each other, and each independently represents hydrogen; deuterium; a methyl group; a tert-butyl group; a phenyl group; or NQ3Q4, or are bonded to adjacent groups to form cyclohexane substituted or unsubstituted with a methyl group; benzene; benzofuran substituted or unsubstituted with a methyl group, a tert-butyl group, or a diphenylamine group substituted or unsubstituted with a tert-butyl group; benzothiophene substituted or unsubstituted with a methyl group, a tert-butyl group, or a diphenylamine group substituted or unsubstituted with a tert-butyl group; naphthofuran; naphthothiophene; diphenylamine substituted or unsubstituted with a methyl group or a tert-butyl group. indene substituted or unsubstituted with a phenyl group; indole substituted or unsubstituted with a methyl group; indoloindene substituted or unsubstituted with a methyl group; indoloindole; tetrahydronaphthofuran substituted or unsubstituted with a methyl group; tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; tetrahydrobenzoindene substituted or unsubstituted with a methyl group; benzodioxine; benzooxathiine; benzodithiine; thiochromene substituted or unsubstituted with a methyl group; chromene substituted or unsubstituted with a methyl group; or dihydronaphthalene substituted or unsubstituted with a methyl group.

[0105] According to one embodiment of the present specification, Q3 and Q4 are the same or different and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 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, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or Q3 and Q4 are the same or different and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and are bonded to each other to form a ring.

[0106] According to one embodiment of the present specification, Q3 and Q4 are the same or different from each other, and each independently represents a methyl group; a tert-butyl group; a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a biphenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a fluorene group substituted or unsubstituted with a methyl group; a tetrahydronaphthyl group substituted or unsubstituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group; or Q3 and Q4 are the same or different from each other, and each independently represents a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group, and are bonded to each other to form a carbazole ring.

[0107] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted 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; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or is bonded to A1 to form any one of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms containing one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a fused ring thereof.

[0108] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or it bonds to A1 to form any one of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, which is unsubstituted or substituted with a linear 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 and contains one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a condensed ring thereof.

[0109] According to one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with any one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; a biphenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a terphenyl group; a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or an unsubstituted tetrahydronaphthyl group; a dibenzofuran group; or a dibenzothiophene group, or a dihydroacridine substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, bonded to said A1; a spiroacridine fluorene; a hexahydrocarbazole substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Dihydrobenzoacridine substituted or unsubstituted by an aryl group in the ring;Hexahydrobenzoacridine substituted or unsubstituted by 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;Spirobenzoacridine;Spirotetrahydrobenzoacridinefluorene;Benzofuroindole;Benzothienoindole;Dihydrobenzoacridine substituted or unsubstituted by 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 Dibenzoazasiline; spirodibenzosiloledibenzoazasiline; phenoxazine; phenothiazine; dihydroindenoindole substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzocarbazole; forming a carbazole substituted or unsubstituted with a linear 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.

[0110] According to one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with at least one selected from a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, and a combination thereof; a biphenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a terphenyl group; a fluorene group substituted or unsubstituted with a methyl group; a tetrahydronaphthyl group substituted or unsubstituted with a methyl group; a dibenzofuran group; a dibenzothiophene group; or a dihydroacridine group substituted or unsubstituted with a methyl group or a phenyl group; a spiroacridinefluorene; a hexahydrocinnaphthalene group substituted or unsubstituted with at least one selected from a methyl group and a tert-butyl group. or substituted or unsubstituted with tert-butyl, adamantyl or phenyl groups to form carbazoles.

[0111] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted 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, or is bonded to R5 to form any one of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms containing one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a fused ring thereof.

[0112] According to one embodiment of the present specification, Ar2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or it is bonded to R5 to form any one of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, which is unsubstituted or substituted with a linear 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 and contains one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a condensed ring thereof.

[0113] According to one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted with any one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; a biphenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a terphenyl group; a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted tetrahydronaphthyl group; a dibenzofuran group; or a dibenzothiophene group, or a dihydroquinoline group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is bonded to said R5; a spiroquinolinefluorene group; a hexahydroindene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Dihydrobenzoquinolines substituted or unsubstituted with polycyclic aryl groups;Hexahydrobenzoquinolines substituted or unsubstituted with linear or branched alkyl groups having 1 to 30 carbon atoms, or with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms;Spirobenzoquinolines;Spirotetrahydrobenzoquinolinefluorenes;Benzofuropyrroles;Benzothienopyrroles;Dihydrobenzoquinolines substituted or unsubstituted with linear or branched alkyl groups having 1 to 30 carbon atoms, or with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms Azaciline; spirodibenzosilole benzoazasiline; benzoxazine; benzothiazine; dihydroindenopyrrole substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzindole; or an indole substituted or unsubstituted with a straight-chain or branched-chain 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.

[0114] According to one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted with at least one selected from a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, and a combination thereof; a biphenyl group substituted or unsubstituted with a methyl group or a tert-butyl group; a terphenyl group; a fluorene group substituted or unsubstituted with a methyl group; a tetrahydronaphthyl group substituted or unsubstituted with a methyl group; a dibenzofuran group; a dibenzothiophene group; or a dihydroquinoline group substituted or unsubstituted with a methyl group or a phenyl group; a spiroacridine quinoline group; a hexafluorophenyl group substituted or unsubstituted with at least one selected from a methyl group and a tert-butyl group. benzothienopyrrole; dihydrobenzoazasiline substituted or unsubstituted with methyl or phenyl groups; spirobenzoquinoline; spirotetrahydrobenzoquinolinefluorene; benzofuropyrrole; benzothienopyrrole; dihydrobenzoazasiline substituted or unsubstituted with methyl or phenyl groups; spirobenzosiloledibenzoazasiline; benzoxazine; benzothiazine; dihydroindenopyrrole substituted or unsubstituted with methyl or phenyl groups; benzindole; or indole substituted or unsubstituted with tert-butyl, adamantyl, or phenyl groups.

[0115] According to one embodiment of the present specification, Z1 to Z3 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted linear 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 aryl group having 6 to 30 carbon atoms; or NQ5Q6, or form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

[0116] According to one embodiment of the present specification, Z1 to Z3 are the same or different from each other, and each independently represent hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or are bonded to adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with at least one substituent selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0117] According to one embodiment of the present specification, Z1 to Z3 are the same or different from each other and each independently represents hydrogen; deuterium; a methyl group; an isopropyl group; a tert-butyl group; a cyclohexyl group; deuterium; a phenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or are bonded to adjacent groups to form benzene; indene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthofuran; tetrahydronaphthofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzothiophene; or an indole substituted or unsubstituted with at least one substituent selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0118] According to one embodiment of the present specification, Z1 to Z3 are the same or different from each other and each independently represents hydrogen; deuterium; a methyl group; an isopropyl group; a tert-butyl group; a cyclohexyl group; a phenyl group substituted or unsubstituted with deuterium or a methyl group; or NQ5Q6, or are bonded to adjacent groups to form benzene; indene substituted or unsubstituted with a methyl group; benzofuran substituted or unsubstituted with a tert-butyl group; naphthofuran; tetrahydronaphthofuran substituted or unsubstituted with a methyl group; benzothiophene; or indole substituted or unsubstituted with a phenyl group or a tetrahydronaphthyl group substituted with a methyl group.

[0119] According to one embodiment of the present specification, at least one of Z1 to Z3 is a substituent other than hydrogen, or is bonded to adjacent groups to form a substituted or unsubstituted ring.

[0120] According to one embodiment of the present specification, at least one of Z1 to Z3 is a substituent other than hydrogen.

[0121] According to one embodiment of the present specification, Z2 is deuterium; a substituted or unsubstituted linear 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 aryl group having 6 to 30 carbon atoms; or NQ5Q6.

[0122] According to one embodiment of the present specification, Z2 is deuterium; a linear 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, which is substituted or unsubstituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6.

[0123] According to one embodiment of the present specification, Z2 is deuterium; a methyl group; an iso-propyl group; a tert-butyl group; a cyclohexyl group; a phenyl group substituted or unsubstituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6.

[0124] According to one embodiment of the present specification, Z2 is deuterium; a methyl group; an iso-propyl group; a tert-butyl group; a cyclohexyl group; a phenyl group unsubstituted or substituted with deuterium or a methyl group; or NQ5Q6.

[0125] According to one embodiment of the present specification, Z1 and Z3 are hydrogen.

[0126] According to one embodiment of the present specification, Z1 and Z3 are deuterium.

[0127] According to one embodiment of the present specification, Q5 and Q6 are the same or different and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 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, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0128] According to one embodiment of the present specification, Q5 and Q6 are the same or different and each independently represent a phenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a dibenzofuran group; or a dibenzothiophene group.

[0129] According to one embodiment of the present specification, Q5 and Q6 are the same or different, and each independently represents a phenyl group substituted or unsubstituted with a methyl group; a biphenyl group substituted or unsubstituted with a methyl group or a biphenyl group; a fluorene group substituted or unsubstituted with a methyl group; a tetrahydronaphthyl group substituted or unsubstituted with a methyl group; a dibenzofuran group; or a dibenzothiophene group.

[0130] According to one embodiment of the present specification, Z1 and G3 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

[0131] According to one embodiment of the present specification, Z1 and G3 are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and a combination thereof.

[0132] According to one embodiment of the present specification, Z1 and G3 are bonded to each other to form an indole substituted or unsubstituted with at least one substituent selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a fused ring group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring, and a combination thereof.

[0133] According to one embodiment of the present specification, Z1 and G3 are bonded to each other to form an indole substituted or unsubstituted with a phenyl group, or a tetrahydronaphthyl group substituted with a methyl group.

[0134] According to one embodiment of the present specification, A1 is selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a condensed ring group of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and which is substituted or unsubstituted with NQ1Q2; Q1 and Q2 are the same or different and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a condensed ring of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; R5 to R8 are the same or different and each independently represent hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or are bonded to adjacent groups and substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms. Unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a condensed ring of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms;or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; Q3 and Q4 are the same or different and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; a condensed 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, each of which is substituted or unsubstituted with an alkyl group; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or said Q3 and Q4 are the same or different and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, each of which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and which are bonded to each other to form a ring, and said Ar1 is a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with any one or more selected from the group consisting of a polycyclic aryl group, and a combination thereof; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a condensed ring group of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, bonded to A1. Ar2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with at least one selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof, and forms any one of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms containing one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a condensed ring thereof;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, each substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted group, bonded to said R5, with a linear 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; a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms containing one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, or a condensed ring thereof, and at least one of Z1 to Z3 is selected from the group consisting of deuterium, a linear 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 cycloalkyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or NQ5Q7, which are bonded to adjacent groups to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, which is substituted or unsubstituted with at least one substituent selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and combinations thereof. Q5 and Q6 are the same or different and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, and a fused ring group of a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms;or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and when Ar2 and R5 form a benzoxazine ring, the benzoxazine ring is an unsubstituted benzoxazine ring, and when Ar1 is a phenyl group, A1 is substituted or unsubstituted benzene, R6 to R8 are hydrogen, adjacent groups among Z1 to Z3 are not bonded to form a substituted or unsubstituted ring, and Ar2 and R5 simultaneously form an indole ring, the indole ring is a substituted indole ring;

[0135] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and each independently represents hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or is bonded to adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a condensed ring of a substituted or unsubstituted 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 heterocycle having 2 to 30 carbon atoms.

[0136] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ3Q4, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; forms an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a condensed ring 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0137] According to one embodiment of the present specification, R1 to R4 are the same or different from each other and each independently represents a hydrogen atom; a methyl group; a tert-butyl group; a phenyl group; or NQ3Q4, or are bonded to adjacent groups to each other to form a cyclohexane substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzene; benzofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthofuran; naphthothiophene; indene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; indole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; indolyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms. tetrahydronaphthofuran substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; tetrahydronaphthothiophene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; tetrahydrobenzoindene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; benzodioxine; benzooxathiine; benzodithiine; thiochromene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; chromene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or dihydronaphthalene substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0138] According to one embodiment of the present specification, R1 to R4 are the same or different and each independently represent a hydrogen atom; a methyl group; a tert-butyl group; a phenyl group; or NQ3Q4, or are bonded to adjacent groups to form a cyclohexane substituted or unsubstituted with a methyl group; a benzene; a benzofuran substituted or unsubstituted with a methyl group or a tert-butyl group; a benzothiophene substituted or unsubstituted with a methyl group or a tert-butyl group; a naphthofuran; a naphthothiophene; an indene substituted or unsubstituted with a methyl group; an indole substituted or unsubstituted with a phenyl group; a methyl group. substituted or unsubstituted indoloindene; indoloindole; tetrahydronaphthofuran substituted or unsubstituted with a methyl group; tetrahydronaphthothiophene substituted or unsubstituted with a methyl group; tetrahydrobenzoindene substituted or unsubstituted with a methyl group; benzodioxine; benzooxathiine; benzodithiine; thiochromene substituted or unsubstituted with a methyl group; chromene substituted or unsubstituted with a methyl group; or dihydronaphthalene substituted or unsubstituted with a methyl group.

[0139] According to one embodiment of the present specification, the definitions of Q3 and Q4 are as described above.

[0140] According to one embodiment of the present specification, R4 is bonded to Ar1 to form any one of a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms containing one or more of N, S, O, and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a condensed ring thereof.

[0141] According to one embodiment of the present specification, R4 is bonded to Ar1 to form any one of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and a condensed ring thereof, which is substituted or unsubstituted with a linear 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, and which contains one or more of N, S, O, and Si.

[0142] According to one embodiment of the present specification, R4 is bonded to Ar1 and is selected from the group consisting of dihydroquinoline substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spiroquinolinefluorene; hexahydroindene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dihydrobenzoquinoline substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; hexahydrobenzoquinoline substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzoquinoline; spirotetrahydroben benzoquinolinefluorene; benzofuropyrrole; benzothienopyrrole; dihydrobenzoazasiline substituted or unsubstituted with 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; spirodibenzosilolebenzoazasiline; benzoxazine; benzothiazine; dihydroindenopyrrole substituted or unsubstituted with 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; benzindole; or indole substituted or unsubstituted with 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.

[0143] According to one embodiment of the present specification, R4 is combined with Ar1 to form a dihydroquinoline substituted or unsubstituted with a methyl group or a phenyl group; a spiroacridine quinoline; a hexahydroindene substituted or unsubstituted with at least one selected from a methyl group and a tert-butyl group; a dihydrobenzoquinoline substituted or unsubstituted with a methyl group or a phenyl group; a hexahydrobenzoquinoline substituted or unsubstituted with a methyl group or a phenyl group; a spirobenzoquinoline; a spirotetrahydrobenzoquinolinefluorene; a benzofuropyrrole; a benzothienopyrrole; a dihydrobenzoazasiline substituted or unsubstituted with a methyl group or a phenyl group; a spirobenzosiloledibenzoazasiline; a benzoxazine; a benzothiazine; a dihydroindenopyrrole substituted or unsubstituted with a methyl group or a phenyl group; a benzindole; or an indole substituted or unsubstituted with a tert-butyl group, an adamantyl group, or a phenyl group.

[0144] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds:

[0145] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0146]

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[0147]

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[0148]

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[0149]

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[0150]

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[0151]

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[0152]

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[0153]

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[0154]

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[0155]

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[0156]

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[0157]

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[0158]

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[0159]

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[0160]

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[0161]

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[0162]

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[0163]

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[0164]

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[0165]

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[0166] In the above compounds, t-Bu means a tert-butyl group.

[0167] Chemical formula H will be described in detail below. [Chemical formula H] [ka] In the above formula H, L20 and L21 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; Ar20 and Ar21 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; At least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group; R200 and R201 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r201 is an integer of 1 to 7, and when r201 is 2 or more, the 2 or more R201's are the same or different from each other.

[0168] In this specification, even if it is not explicitly stated that H in the chemical formula is substituted with deuterium, it may include those substituted with deuterium.

[0169] In one embodiment of the present specification, L20 and L21 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0170] In one embodiment of the present specification, L20 and L21 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0171] In one embodiment of the present specification, L20 and L21 are substituted or unsubstituted with deuterium.

[0172] In one embodiment of the present specification, L20 and L21 are the same or different, and each independently represents a direct bond; a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

[0173] In one embodiment of the present specification, L20 is a direct bond.

[0174] In one embodiment of the present specification, L21 is a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthylene group substituted or unsubstituted with deuterium.

[0175] In one embodiment herein, at least one of L20 and L21 is a direct bond.

[0176] In one embodiment of the present specification, at least one of L20 and L21 is a substituted or unsubstituted arylene group.

[0177] In one embodiment of the present specification, L20 and L21 are the same or different, and each independently represent a direct bond; or any one selected from the following structures:

[0178] [ka] In the above structure, The dotted line indicates the position of connection to H of the formula, D represents deuterium, k1 represents an integer of 0 to 4, and k2 represents an integer of 0 to 6.

[0179] In one embodiment herein, k1 is 0.

[0180] In another embodiment, k1 is 4.

[0181] In one embodiment herein, k2 is 0.

[0182] In yet other embodiments, k2 is 6.

[0183] In one embodiment of the present specification, each of L20 and L21 may be deuterated.

[0184] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent 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.

[0185] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

[0186] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic O-containing heterocyclic group having 2 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic S-containing heterocyclic group having 2 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic N-containing heterocyclic group having 2 to 20 carbon atoms.

[0187] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a substituted or unsubstituted monocyclic to 4-ring aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.

[0188] In one embodiment of the present specification, Ar20 and Ar21 are the same or different, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzothiophene group; a substituted or unsubstituted carbazole group, or a substituted or unsubstituted benzocarbazole group.

[0189] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; a fluorene group substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms; a benzofluorene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; represents an unsubstituted dibenzofuran group; a naphthobenzofuran group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms; a naphthobenzothiophene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms; a carbazole group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; or a benzocarbazole group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, wherein Ar20 and Ar21 may each be deuterated.

[0190] In one embodiment of the present specification, Ar20 and Ar21 are the same or different, and each independently represents a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a fluorene group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a deuterated phenyl group; a benzofluorene group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a deuterated phenyl group; dibenzofuran groups unsubstituted or substituted with deuterated substituents; deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, N-phenylcarbazole, N-biphenylcarbazole or dibenzofuran groups unsubstituted or substituted with deuterated substituents; deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, N-phenylcarbazole, N-biphenylcarbazole or dibenzothiophene substituted or unsubstituted by deuterated substituents thereof; deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene a naphthobenzothiophene group, a dibenzothiophene group, a naphthobenzofuran group, a naphthobenzothiophene group, an N-phenylcarbazole group, an N-biphenylcarbazole group, or a naphthobenzothiophene group substituted or unsubstituted with deuterated substituents thereof; a carbazole group substituted or unsubstituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a deuterated substituents thereof; or a benzocarbazole group substituted or unsubstituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a deuterated substituents thereof.

[0191] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group.

[0192] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted O-containing heterocyclic group; or a substituted or unsubstituted S-containing heterocyclic group.

[0193] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted tricyclic or tetracyclic O-containing heterocyclic group; or a substituted or unsubstituted tricyclic or tetracyclic S-containing heterocyclic group.

[0194] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted O-containing heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted S-containing heterocyclic group having 2 to 30 carbon atoms.

[0195] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted O-containing heterocyclic group having 2 to 20 carbon atoms; or a substituted or unsubstituted S-containing heterocyclic group having 2 to 20 carbon atoms.

[0196] In one embodiment of the present specification, at least one of Ar20 and Ar21 is an O- or S-containing heterocyclic group, and the heterocyclic group is at least one group selected from the group consisting of deuterium, an alkyl group, an aryl group, and an aryl group; or at least two groups selected from the group are substituted or unsubstituted with a linking group.

[0197] In one embodiment of the present specification, at least one of Ar20 and Ar21 is an O- or S-containing heterocyclic group, and the heterocyclic group is substituted or unsubstituted with deuterium; an alkyl group; a deuterated alkyl group; an aryl group; a deuterated aryl group; an alkylaryl group, a deuterated alkylaryl group; a heterocyclic group; a deuterated heterocyclic group; an aryl heterocyclic group; or a deuterated aryl heterocyclic group.

[0198] In one embodiment of the present specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzothiophene group.

[0199] In one embodiment of the present specification, at least one of Ar20 and Ar21 is represented by the following chemical formula Het1.

[0200] [Chemical formula Het1] [ka] In the formula Het1, The dotted line connects to the formula H, M1 is O; or S; R11 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or is joined with adjacent groups to each other to form a substituted or unsubstituted ring; r11 is an integer of 0 to 7, and when r11 is 2 or greater, R11 are the same or different.

[0201] In one embodiment herein, M is O.

[0202] In one embodiment herein, M is S.

[0203] In one embodiment of the present specification, R11 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring.

[0204] In one embodiment of the present specification, R11 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted linear 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 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 is bonded to adjacent groups to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

[0205] In one embodiment of the present specification, R11 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 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 is bonded to adjacent groups to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

[0206] In one embodiment of the present specification, R11 is hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms and substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms and substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or is bonded to adjacent groups to form a ring having 5 to 30 carbon atoms and substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms or a heterocyclic group having 2 to 30 carbon atoms, and R11 or the ring may be deuterated.

[0207] In one embodiment of the present specification, R11 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzothiophene group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzothiophene group; a substituted or unsubstituted carbazole group, or a substituted or unsubstituted benzocarbazole group, or is bonded to adjacent groups to form a substituted or unsubstituted benzene ring.

[0208] In one embodiment of the present specification, R11 is selected from the group consisting of hydrogen, deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium, a fluorene group substituted or unsubstituted with deuterium, a methyl group, a phenyl group or a deuterated phenyl group, a benzofluorene group substituted or unsubstituted with deuterium, a methyl group, a phenyl group or a deuterated phenyl group, a deuterium, a phenyl group, a biphenyl group, a naphthyl group, Dimethylfluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, N-phenylcarbazole, N-biphenylcarbazole or dibenzofuran groups unsubstituted or substituted with deuterated substituents thereof; deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, N-phenylcarbazole, N-biphenylcarbazole or deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthobenzofuran, naphthobenzothiophene, N-phenylcarbazole, N-biphenylcarbazole or dibenzothiophene groups substituted or unsubstituted with deuterated substituents thereof; deuterium, phenyl, biphenyl, naphthyl, dimethylfluorene, dibenzofuran, dibenzothiophene groups a naphthobenzofuran group, a naphthobenzothiophene group, an N-phenylcarbazole group, an N-biphenylcarbazole group, or a naphthobenzothiophene group substituted or unsubstituted with deuterated substituents thereof; a carbazole group substituted or unsubstituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a deuterated substituents thereof; or a benzocarbazole group substituted or unsubstituted with deuterium, a phenyl group, a biphenyl group, a naphthyl group, or a deuterated substituents thereof.

[0209] In one embodiment of the present specification, r11 is an integer of 0-7.

[0210] In one embodiment of the present invention, R11 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and r11 is 1 or 2. In one embodiment of the present specification, the formula Het1 is the following formula Het1-1:

[0211] [Chemical formula Het1-1] [ka] In the above formula Het1-1, The definitions of M1, R11 and r11 are the same as those defined in the above formula Het1; Any one of a1* to a8* is linked to H of the chemical formula.

[0212] In one embodiment of the present specification, the remainder of a1* to a8* that is not linked to H in the chemical formula is R11.

[0213] In one embodiment of the present specification, the chemical formula Het1 is represented by any one of the following chemical formulae Het2 to Het4.

[0214] [Chemical formula Het2] [ka] [Chemical formula Het3] [ka] [Chemical formula Het4] [ka] In the above chemical formulas Het2 to Het4, The dotted line and M1 are defined as above in formula Het1. R11 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r11' is an integer of 0 to 9, and when r11' is 2 or greater, R11 are the same or different.

[0215] In one embodiment of the present specification, r11' is an integer of 0-7.

[0216] In one embodiment herein, R11 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and r11' is 1 or 2.

[0217] In one embodiment of the present specification, the chemical formula Het2 is represented by the following chemical formula Het2-1. [Chemical formula Het2-1] [ka] In the above formula Het2-1, The definitions of M1, R11 and r11' are the same as those defined in the above formula Het2; One of a1* to a10* is linked to H of the chemical formula.

[0218] In one embodiment of the present specification, the chemical formula Het3 is represented by the following chemical formula Het3-1. [Chemical formula Het3-1] [ka] In the above formula Het3-1, The definitions of M1, R11 and r11' are the same as those defined in the above formula Het3; One of a1* to a10* is linked to H of the chemical formula.

[0219] In one embodiment of the present specification, the chemical formula Het4 is represented by the following chemical formula Het4-1.

[0220] [Chemical formula Het4-1] [ka] In the above formula Het4-1, The definitions of M1, R11 and r11' are the same as those defined in the above formula Het3; One of a1* to a10* is linked to H of the chemical formula.

[0221] In one embodiment of the present specification, the remainder of a1* to a10* that is not connected to H in the chemical formula is R11.

[0222] In one embodiment herein, a1* is linked to said formula H. In another embodiment, a2* is linked to said formula H. In yet another embodiment, a3* is linked to said formula H. In yet another embodiment, a4* is linked to said formula H. In another embodiment, a5* is linked to said formula H. In another embodiment, a6* is linked to said formula H. In yet another embodiment, a7* is linked to said formula H. In another embodiment, a8* is linked to said formula H. In another embodiment, a9* is linked to said formula H. In yet another embodiment, a10* is linked to said formula H.

[0223] When the compound Het1 is connected to the compound H via a3* or a4*, the voltage of the device is reduced and the efficiency is increased.

[0224] In one embodiment of the present specification, the formula Het1 may be deuterated.

[0225] In one embodiment of the present specification, one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group, and the other is a substituted or unsubstituted aryl group.

[0226] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently a substituted or unsubstituted heterocyclic group.

[0227] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0228] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted aryl group, and Ar21 is a substituted or unsubstituted heterocyclic group.

[0229] In one embodiment of the present specification, any one of Ar20 and Ar21 is represented by the chemical formula Het1, and the other is a substituted or unsubstituted aryl group.

[0230] In one embodiment of the present specification, either Ar20 or Ar21 is represented by the chemical formula Het1, and the other is a substituted or unsubstituted N-containing heterocyclic group.

[0231] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are each independently represented by the chemical formula Het1.

[0232] In one embodiment of the present specification, Ar20 is represented by the chemical formula Het1, and Ar21 is a substituted or unsubstituted aryl group.

[0233] In one embodiment of the present specification, Ar20 is represented by the formula Het1, and Ar21 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted N-containing heterocyclic group.

[0234] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted aryl group, and Ar21 is represented by the chemical formula Het1.

[0235] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted aryl group or a substituted or unsubstituted N-containing heterocyclic group, and Ar21 is represented by the chemical formula Het1.

[0236] In one embodiment of the present specification, the chemical formula H is represented by any one of the following chemical formulae H-1 to H-4. [Chemical formula H-1] [ka] [Chemical formula H-2] [ka] [Chemical formula H-3] [ka] [Chemical formula H-4] [ka] In the chemical formulas H-1 to H-4, L20, L21, R200, R201 and r201 are as defined above in formula H; M1 is O; or S; M2 is O;S; or NR13; Ar20 and Ar21 are the same or different and each independently represents a substituted or unsubstituted aryl group; R11 to R13 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; Each of r11 and r12 is an integer of 0 to 7, and when each of r11 and r12 is 2 or greater, the substituents in the parentheses are the same or different.

[0237] In one embodiment of the present specification, the above description of R11 applies to R12.

[0238] In one embodiment of the present specification, the above description regarding r11 applies to r12.

[0239] In one embodiment of the present specification, R13 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0240] In one embodiment of the present specification, R13 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0241] In one embodiment of the present specification, R13 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium.

[0242] In one embodiment of the present specification, R13 is a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted or unsubstituted naphthyl group.

[0243] In one embodiment of the present specification, R200 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted linear 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 aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0244] In one embodiment of the present specification, R200 is hydrogen; deuterium; fluorine; a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 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.

[0245] In one embodiment of the present specification, R200 is hydrogen; deuterium; 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.

[0246] In one embodiment of the present specification, R200 is hydrogen; deuterium; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

[0247] In one embodiment of the present specification, R200 is hydrogen; deuterium; a substituted or unsubstituted monocyclic to 4-ring aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.

[0248] In one embodiment of the present specification, R200 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0249] In one embodiment of the present specification, R200 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted phenalene group, or a substituted or unsubstituted fluorene group.

[0250] In one embodiment of the present specification, R200 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0251] In one embodiment of the present specification, R200 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium, a phenyl group, or a naphthyl group; a biphenyl group; or a naphthyl group substituted or unsubstituted with deuterium, a phenyl group, or a naphthyl group.

[0252] In one embodiment of the present specification, R200 is a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted naphthyl group.

[0253] According to one embodiment of the present specification, R201 is hydrogen.

[0254] According to one embodiment of the present specification, R201 is deuterium.

[0255] According to one embodiment of the present specification, R201 is deuterium, and r201 is 4 or more.

[0256] According to one embodiment of the present specification, R200 and R201 are deuterium and n201 is 7.

[0257] In one embodiment of the present specification, the chemical formula H is represented by the following chemical formula H-5. [Chemical formula H-5] [ka] In the above chemical formula H-5, The definitions of Ar20, Ar21, L20 and L21 are the same as those defined in the above formula H; D is deuterium and r203 is 0-8.

[0258] In one embodiment of the present specification, r203 is an integer of 4 to 8.

[0259] In one embodiment of the present specification, r203 is 8.

[0260] In one embodiment of the present specification, when the compound represented by chemical formula H is substituted with deuterium, 30% or more of the hydrogen at substitutable positions are substituted with deuterium. In another embodiment, the structure of chemical formula H has 40% or more of the hydrogen at substitutable positions substituted with deuterium. In another embodiment, the structure of chemical formula H has 60% or more of the hydrogen at substitutable positions substituted with deuterium.

[0261] In yet another embodiment, the structure of formula H has 80% or more of hydrogen at substitutable positions substituted with deuterium.In yet another embodiment, the structure of formula H has 100% of hydrogen at substitutable positions substituted with deuterium.

[0262] In one embodiment of the present specification, the chemical formula H is any one selected from the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0263] The present specification provides an organic light-emitting device comprising the compound.

[0264] The present specification includes an anode; a cathode; and an organic layer provided between the anode and the cathode, the organic layer including a light-emitting layer, the light-emitting layer including a compound represented by Chemical Formula 1; and a compound represented by Chemical Formula H.

[0265] In one embodiment of the present specification, the maximum emission peak of the light emitting layer is within a range of 400 nm to 500 nm, that is, the light emitting layer emits blue light. In one embodiment of the present specification, the light-emitting layer includes the compound represented by Chemical Formula 1 as a light-emitting layer dopant and the compound represented by Chemical Formula H as a light-emitting layer host. Specifically, the compound represented by Chemical Formula 1 is a blue fluorescent dopant.

[0266] In one embodiment of the present specification, the light emitting layer contains the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H in a weight ratio of 1:99 to 30:70, more preferably 1:99 to 10:90.

[0267] The light-emitting layer may further include a host material, and the host may be a fused aromatic ring derivative or a heterocyclic ring-containing compound, etc. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and examples of the heterocyclic ring-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and triazine derivatives, and may be a mixture of two or more of these, but are not limited thereto.

[0268] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes one or more dopants and a host.

[0269] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes two or more mixed dopants and a host.

[0270] According to one embodiment of the present specification, at least one of the two or more mixed dopants includes the formula 1, and the host includes a compound represented by the formula H. At least one of the two or more mixed dopants includes the formula 1, and the remaining may be a conventionally known dopant material, but is not limited thereto.

[0271] According to an embodiment of the present specification, at least one of the two or more mixed dopants includes the above-mentioned Formula 1, and the remaining dopants may be at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from the above-mentioned Formula 1, but are not limited thereto.

[0272] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes one or more hosts.

[0273] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes two or more mixed hosts.

[0274] According to one embodiment of the present specification, at least one of the two or more mixed hosts is a compound represented by the chemical formula H.

[0275] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes two mixed hosts, the two mixed hosts are different from each other, and the two hosts are compounds represented by the chemical formula H.

[0276] The organic layer of the organic light-emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, it may 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, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0277] In one embodiment of the present specification, the organic layer of the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0278] In one embodiment of the present specification, the two or more organic layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that simultaneously transports and injects holes, and an electron-blocking layer.

[0279] In one embodiment of the present specification, the organic light emitting device may include, but is not limited to, two or more electron transport layers.

[0280] In one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

[0281] In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0282] For example, a structure of an organic light emitting device according to an embodiment of the present specification is shown in Figure 1. Figure 1 illustrates an example of an organic light emitting device, and is not limited thereto.

[0283] 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emitting layer 3, and a cathode 4 are sequentially stacked. In this structure, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H may be included in the emitting layer 3.

[0284] The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that the light emitting layer of the organic layers contains the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H.

[0285] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0286] For example, the organic light emitting device of the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material usable as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0287] In addition, the compound represented by Formula 1 or the compound represented by Formula H may be formed as an organic layer by a solution coating method as well as a vacuum deposition method during the manufacture of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0288] In addition to the above method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate, but the manufacturing method is not limited thereto.

[0289] The anode material is preferably a material having a large work function so that holes can be easily injected into the organic layer, and examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0290] The cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer, such as, but not limited to, metals or alloys thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and multilayered materials, such as LiF / Al and LiO2 / Al.

[0291] The light-emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the condensed aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the heterocyclic ring-containing compound may be, but is not limited to, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like.

[0292] The dopant material may include, in addition to the compound represented by Chemical Formula 1, an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, a metal complex, etc. Specifically, the aromatic amine derivative may include, as a fused aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene, etc. having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the dopant material may include, but is not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. In addition, the metal complex may include, but is not limited to, an iridium complex, a platinum complex, etc.

[0293] In the present specification, when the compound represented by Chemical Formula 1 is included in an organic layer other than the light-emitting layer or an additional light-emitting layer is provided, the light-emitting material of the light-emitting layer is a material that can emit light in the visible light region by transporting holes and electrons from the hole transport layer and electron transport layer and combining them, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. For example, 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzothiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene are included, but are not limited thereto.

[0294] The hole injection layer is a layer that injects holes from the electrode. The hole injection material is preferably one that has the ability to transport holes and has an excellent hole injection effect in the anode and an excellent hole injection effect in the light emitting layer or light emitting material. In addition, a material that is excellent in the ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material that is excellent in the ability to form a thin film is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, and arylamine-based organic materials; carbazole-based organic materials; nitrile-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of two or more of the above examples, but are not limited thereto.

[0295] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and move them to the light emitting layer, and is preferably a material with high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0296] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is preferably a material that can successfully receive electrons from the cathode and transfer them to the light-emitting layer, and has a high mobility for electrons. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives; LiQ, etc. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, samarium, etc., each of which is followed by an aluminum or silver layer.

[0297] The electron injection layer is a layer that injects electrons from the electrode. The electron injector is preferably one that has excellent electron transport ability, an electron injection effect from the cathode, and an excellent electron injection effect on the light-emitting layer or light-emitting material. In addition, it is preferable to use a substance that prevents the excitation generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylene tetracarboxylic acid, preolenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, mixtures of two or more of the above examples, etc., but are not limited to these.

[0298] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0299] The electron blocking layer is a layer that can prevent electrons injected from the electron injection layer from passing through the light emitting layer to the hole injection layer, thereby improving the life and efficiency of the device. Known materials can be used without limitation, and the electron blocking layer may be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

[0300] The hole blocking layer is a layer that blocks holes from passing through the light emitting layer to reach the cathode, and may be generally formed under the same conditions as the electron injection layer, specifically, but not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, etc.

[0301] Organic light emitting devices according to the present invention may be front-emitting, back-emitting, or dual-emitting, depending on the materials used.

[0302] The compound according to the present specification can act on the same principle as that applied to the organic light-emitting device in organic light-emitting devices including organic phosphorescent devices, organic solar cells, organic photoreceptors, organic transistors, etc. For example, the organic solar cell may have a structure including an anode, a cathode, and a photoactive layer provided between the anode and the cathode, and the photoactive layer may include the compound.

[0303] The organic light-emitting device of the present specification may be manufactured by a typical manufacturing method and material for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned compounds.

[0304] Hereinafter, the present specification will be described in detail with reference to examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified into various other forms, and the scope of the present specification should not be construed as being limited to the examples and comparative examples detailed below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those having average knowledge in the art.

[0305] Preparation Example 1. Preparation of Compound BH1 [ka]

[0306] Production Example 1-1) Production of BH1 Compound 1-1 (20.0 g, 60.0 mmol), dibenzofuran-2-boronic acid (14.0 g, 66.0 mmol) were dissolved in 300 ml of 1,4-dioxane, and K2CO3 (24.9 g, 180 mmol) was dissolved in 100 ml of H2O and placed in a three-neck flask. Pd(P(t-Bu)3)2 (0.68 g, 1.32 mmol) was added and stirred for 5 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 11.5 g of BH1. (Yield 46%, MS [M+H]+ = 421)

[0307] Preparation Example 2. Preparation of Compound BH2 [ka]

[0308] Preparation Example 2-1) Preparation of Compound 2-2 Compound 2-1 (20.0 g, 71.0 mmol), Bis(pinacolato)diboron (27.1 g, 106.6 mmol), and KOAc (20.9 g, 213 mmol) were dissolved in 300 ml of 1,4-dioxane and placed in a three-neck flask. Pd(dppf)Cl2 (1.09 g, 2.13 mmol) was added and stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 18.6 g of compound 2-2. (Yield 80%, MS [M+H]+ = 329)

[0309] Preparation Example 2-2) Preparation of Compound 2-3 Compound 2-2 (20.0 g, 60.9 mmol) and compound 1-1 (18.3 g, 54.8 mmol) were dissolved in 300 ml of 1,4-dioxane, and K2CO3 (25.2 g, 183 mmol) was dissolved in 100 ml of H2O and added to a three-neck flask. Pd(dppf)Cl2 (0.80 g, 1.10 mmol) was added and stirred for 5 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 16.3 g of compound 2-3. (Yield 65%, MS [M+H]+ = 455)

[0310] Preparation Example 2-3) Preparation of Compound BH2 Compound 2-3 (20.0 g, 43.9 mmol), phenylboronic acid (6.4 g, 52.7 mmol) were dissolved in 200 ml of 1,4-dioxane, and K2CO3 (18.2 g, 132 mmol) was dissolved in 70 ml of H2O and added to a three-neck flask. Pd(P(t-Bu)3)2 (0.45 g, 0.88 mmol) was added and stirred for 5 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 14.9 g of compound BH2. (Yield 68%, MS [M+H]+ = 497)

[0311] Preparation Example 3. Preparation of compound BH3 [ka]

[0312] Production Example 3-1) Production of Compound BH3 Using the same method as in Preparation Example 2-3, 17.9 g of compound BH3 was obtained (yield 65%, MS [M+H]+ = 613).

[0313] Preparation Example 4. Preparation of compound BH4 [ka]

[0314] Preparation Example 4-1) Preparation of Compound 4-2 Using the same method as in Preparation Example 2-1, 17.1 g of compound 4-2 was obtained (yield 74%, MS [M+H]+ = 329).

[0315] Preparation Example 4-2) Preparation of Compound 4-3 Using the same method as in Preparation Example 2-2, 14.3 g of compound 4-3 was obtained (yield 57%, MS [M+H]+ = 455).

[0316] Preparation Example 4-3) Preparation of Compound BH4 Using the same method as in Preparation Example 2-3, 14.9 g of compound BH4 was obtained (yield 68%, MS [M+H]+ = 497).

[0317] Preparation Example 5. Preparation of Compound BH5 [ka]

[0318] Preparation Example 5-1) Preparation of Compound BH5 Using the same method as in Preparation Example 4-3, 13.1 g of compound BH5 was obtained (yield 45%, MS [M+H]+ = 662).

[0319] Preparation Example 6. Preparation of Compound BH6 [ka]

[0320] Preparation Example 6-1) Preparation of Compound 6-2 Using the same method as in Preparation Example 2-1, 16.6 g of compound 6-2 was obtained (yield 72%, MS [M+H]+ = 329).

[0321] Preparation Example 6-2) Preparation of Compound 6-3 Using the same method as in Preparation Example 2-2, 15.3 g of compound 6-3 was obtained (yield 61%, MS [M+H]+ = 455).

[0322] Preparation Example 6-3) Preparation of Compound BH6 Using the same method as in Preparation Example 2-3, 14.7 g of compound BH6 was obtained (yield 68%, MS [M+H]+ = 497).

[0323] Preparation Example 7. Preparation of Compound BH7 [ka]

[0324] Preparation Example 7-1) Preparation of Compound 7-3 Using the same method as in Preparation Example 2-2, 16.5 g of compound 7-3 was obtained (yield 64%, MS [M+H]+ = 532).

[0325] Preparation Example 7-2) Preparation of Compound BH7 Using the same method as in Preparation Example 2-3, 14.4 g of compound BH7 was obtained (yield 67%, MS [M+H]+ = 573).

[0326] Preparation Example 8. Preparation of Compound BH8 [ka]

[0327] Preparation Example 8-1) Preparation of Compound BH8 Using the same method as in Preparation Example 1-1, 12.7 g of compound BH8 was obtained (yield 52%, MS [M+H]+ = 471).

[0328] Preparation Example 9. Preparation of Compound BH9 [ka]

[0329] Preparation Example 9-1) Preparation of Compound 9-2 Using the same method as in Preparation Example 2-1, 18.1 g of compound 9-2 was obtained (yield 72%, MS [M+H]+ = 329).

[0330] Preparation Example 9-2) Preparation of Compound 9-3 Using the same method as in Preparation Example 2-2, 17.0 g of compound 9-3 was obtained (yield 68%, MS [M+H]+ = 455).

[0331] Preparation Example 9-3) Preparation of Compound BH9 Using the same method as in Preparation Example 2-3, 14.7 g of compound BH9 was obtained (yield 68%, MS [M+H]+ = 497).

[0332] Preparation Example 10. Preparation of Compound BH10 [ka]

[0333] Preparation Example 10-1) Preparation of Compound BH10 Using the same method as in Preparation Example 1-1, 16.8 g of compound BH10 was obtained (yield 68%, MS [M+H]+ = 471).

[0334] Preparation Example 11. Preparation of Compound BH11 [ka]

[0335] Preparation Example 11-1) Preparation of Compound 11-1 Using the same method as in Preparation Example 2-2, 18.6 g of compound 11-1 was obtained (yield 71%, MS [M+H]+ = 506).

[0336] Preparation Example 11-2) Preparation of Compound BH11 Using the same method as in Preparation Example 2-3, 14.7 g of compound BH11 was obtained (yield 68%, MS [M+H]+ = 497).

[0337] Preparation Example 12. Preparation of Compound BH12 [ka]

[0338] Preparation Example 12-1) Preparation of Compound 12-2 Using the same method as in Preparation Example 2-1, 18.5 g of compound 12-2 was obtained (yield 74%, MS [M+H]+ = 329).

[0339] Preparation Example 12-2) Preparation of Compound 12-3 Using the same method as in Preparation Example 2-2, 17.1 g of compound 12-3 was obtained (yield 68%, MS [M+H]+ = 455).

[0340] Preparation Example 12-3) Preparation of Compound BH12 Using the same method as in Preparation Example 2-3, 13.9 g of compound BH12 was obtained (yield 64%, MS [M+H]+ = 497).

[0341] Preparation Example 13. Preparation of compound BH13 [ka]

[0342] Preparation Example 13-1) Preparation of Compound BH13 Using the same method as in Preparation Example 2-3, 17.0 g of compound BH13 was obtained (yield 73%, MS [M+H]+ = 587).

[0343] Preparation Example 14. Preparation of compound BH14 [ka]

[0344] Preparation Example 14-1) Preparation of Compound BH14 Using the same method as in Preparation Example 1-1, 12.8 g of compound BH14 was obtained (yield 46%, MS [M+H]+ = 586).

[0345] Preparation Example 15. Preparation of Compound BH15 [ka]

[0346] Preparation Example 15-1) Preparation of Compound BH15 Using the same method as in Preparation Example 1-1, 11.8 g of compound BH15 was obtained (yield 42%, MS [M+H]+ = 471).

[0347] Preparation Example 16. Preparation of Compound BH16 [ka]

[0348] Preparation Example 16-1) Preparation of Compound BH16 Using the same method as in Preparation Example 1-1, 11.8 g of compound BH16 was obtained (yield 42%, MS [M+H]+ = 471).

[0349] Preparation Example 17. Preparation of compound BH17 [ka]

[0350] Preparation Example 17-1) Preparation of Compound BH17 Using the same method as in Preparation Example 1-1, 16.6 g of compound BH17 was obtained (yield 61%, MS [M+H]+ = 521).

[0351] Preparation Example 18. Preparation of compound BH18 [ka]

[0352] Preparation Example 18-1) Preparation of Compound BH18 Using the same method as in Preparation Example 1-1, 13.5 g of compound BH18 was obtained (yield 48%, MS [M+H]+ = 471).

[0353] Preparation Example 19. Preparation of Compound BH19 [ka]

[0354] Preparation Example 19-1) Preparation of Compound BH19 Using the same method as in Preparation Example 1-1, 12.1 g of compound BH19 was obtained (yield 43%, MS [M+H]+ = 471).

[0355] Preparation Example 20. Preparation of compound BH20 [ka]

[0356] Preparation Example 20-1) Preparation of Compound 20-2 Using the same method as in Preparation Example 2-1, 19.3 g of compound 20-2 was obtained (yield 85%, MS [M+H]+ = 379).

[0357] Preparation Example 20-2) Preparation of Compound 20-3 Using the same method as in Preparation Example 2-2, 20.8 g of compound 20-3 was obtained (yield 69%, MS [M+H]+ = 506).

[0358] Preparation Example 20-3) Preparation of Compound BH20 Using the same method as in Preparation Example 2-3, 12.4 g of compound BH20 was obtained (yield 57%, MS [M+H]+ = 547).

[0359] Preparation Example 21. Preparation of Compound BH21 [ka]

[0360] Preparation Example 21-1) Preparation of Compound BH21 Using the same method as in Preparation Example 1-1, 13.4 g of compound BH21 was obtained (yield 47%, MS [M+H]+ = 471).

[0361] Preparation Example 22. Preparation of Compound BH22 [ka]

[0362] Preparation Example 22-1) Preparation of Compound BH22 Using the same method as in Preparation Example 1-1, 15.2 g of compound BH22 was obtained (yield 56%, MS [M+H]+ = 521).

[0363] Preparation Example 23. Preparation of compound BH23 [ka]

[0364] Preparation Example 23-1) Preparation of Compound BH23 Compound BH2 (20 g) and TfOH (4 ml) were added to C6D6 (300 ml) and stirred for 2 hours. After the reaction was completed, D2O (50 ml) was added and stirred for 30 minutes, and then trimethylamine (6 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4 and recrystallized with ethyl acetate to obtain 14.2 g of compound BH23. (Yield 68%, MS [M+H]+ = 521)

[0365] Preparation Example 24. Preparation of compound BH24 [ka]

[0366] Preparation Example 24-1) Preparation of Compound 24-1 d10-anthracene (50.0 g, 265 mmol), N-bromosuccinimide (NBS) (47.3 g, 265 mmol), and 500 ml of dimethylformamide (DMF) were placed in a two-neck flask and stirred at room temperature under an argon atmosphere for 6 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 55.1 g of compound 24-1. (Yield 78%, MS [M+H]+ = 267)

[0367] Preparation Example 24-2) Preparation of Compound 24-2 Compound 24-1 (50.0 g, 188 mmol), naphthalene-1-ylboronic acid (35.6 g, 207 mmol) were dissolved in 500 ml of 1,4-dioxane, and K2CO3 (77.9 g, 563 mmol) was dissolved in 200 ml of H2O and added to a three-neck flask. Pd(P(t-Bu)3)2 (1.92 g, 3.8 mmol) was added and stirred for 5 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 40.5 g of compound 24-2. (Yield 82%, MS [M+H]+ = 264)

[0368] Preparation Example 24-3) Preparation of Compound 24-3 Compound 24-2 (20.0 g, 75.9 mmol), N-bromosuccinimide (NBS) (14.9 g, 83.5 mmol), and 300 ml of dimethylformamide (DMF) were placed in a two-neck flask and stirred at room temperature under an argon atmosphere for 10 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 20.1 g of compound 24-3. (Yield 77%, MS [M+H]+ = 342)

[0369] Preparation Example 24-4) Preparation of Compound BH24 Compound 24-3 (20.0 g, 58.6 mmol), dibenzofuran-2-boronic acid (13.7 g, 64.5 mmol) were dissolved in 300 ml of 1,4-dioxane, and K2CO3 (24.3 g, 176 mmol) was dissolved in 100 ml of H2O and added to a three-neck flask. Pd(P(t-Bu)3)2 (0.60 g, 1.2 mmol) was added and stirred for 5 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain 15.9 g of compound BH24. (Yield 63%, MS [M+H]+ = 429)

[0370] Preparation Example 25. Preparation of Compound BH25 [ka]

[0371] Preparation Example 25-1) Preparation of Compound 25-1 Using the same method as in Preparation Example 23-1, 18.2 g of compound 25-1 was obtained (yield 86%, MS [M+H]+ = 321).

[0372] Preparation Example 25-2) Preparation of Compound 25-2 Using the same method as in Preparation Example 24-3, 17.8 g of compound 25-2 was obtained (yield 72%, MS [M+H]+ = 399).

[0373] Preparation Example 25-3) Preparation of Compound BH25 Using the same method as in Preparation Example 2-3, 14.3 g of compound BH25 was obtained (yield 53%, MS [M+H]+ = 536).

[0374] Preparation Example 26. Preparation of Compound BH26 [ka]

[0375] Preparation Example 26-1) Preparation of Compound BH26 Using the same method as in Preparation Example 2-3, 12.5 g of compound BH26 was obtained (yield 50%, MS [M+H]+ = 529).

[0376] Preparation Example 27. Preparation of compound BH27 [ka]

[0377] Preparation Example 27-1) Preparation of Compound 27-1 Using the same method as in Preparation Example 24-2, 18.8 g of compound 27-1 was obtained (yield 93%, MS [M+H]+ = 260).

[0378] Preparation Example 27-2) Preparation of Compound 27-2 Using the same method as in Preparation Example 24-3, 17 g of compound 27-2 was obtained (yield 65%, MS [M+H]+ = 339).

[0379] Preparation Example 27-3) Preparation of Compound 27-3 Using the same method as in Preparation Example 2-2, 14.4 g of compound 27-3 was obtained (yield 48%, MS [M+H]+ = 511).

[0380] Preparation Example 27-4) Preparation of Compound BH27 Using the same method as in Preparation Example 2-3, 12.4 g of compound BH27 was obtained (yield 57%, MS [M+H]+ = 547).

[0381] Preparation Example 28. Preparation of compound BH28 [ka]

[0382] Preparation Example 28-1) Preparation of Compound 28-1 Using the same method as in Preparation Example 24-2, 18.5 g of compound 28-1 was obtained (yield 93%, MS [M+H]+ = 260).

[0383] Preparation Example 28-2) Preparation of Compound 28-2 Using the same method as in Preparation Example 24-3, 17.9 g of compound 28-2 was obtained. (Yield 69%, MS [M+H]+ = 342)

[0384] Preparation Example 28-3) Preparation of Compound BH28 Using the same method as in Preparation Example 2-3, 11.9 g of compound BH28 was obtained (yield 42%, MS [M+H]+ = 479).

[0385] Preparation Example 29. Preparation of compound BH29 [ka]

[0386] Preparation Example 29-1) Preparation of Compound BH29 Using the same method as in Preparation Example 2-3, 11.9 g of compound BH29 was obtained (yield 42%, MS [M+H]+ = 479).

[0387] Preparation Example 30. Preparation of compound BH30 [ka]

[0388] Preparation Example 30-1) Preparation of Compound 30-1 Using the same method as in Preparation Example 2-2, 15.3 g of compound 30-1 was obtained (yield 59%, MS [M+H]+ = 521).

[0389] Preparation Example 30-2) Preparation of Compound BH30 Using the same method as in Preparation Example 2-3, 14.0 g of compound BH30 was obtained (yield 65%, MS [M+H]+ = 562).

[0390] Synthesis Example 31. Synthesis of Compound BD1 [ka]

[0391] 1) Synthesis of compound 31-1 Under a nitrogen atmosphere, 30g of 1-bromo-3-chloro-5-methylbenzene, 43.7g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 32.3g of sodium tert-butoxide, and 1.2g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 2 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 56g of compound 31-1. (Yield 75%) MS[M+H]+=515

[0392] 2) Synthesis of compound 31-2 30g of compound 31-1, 23.8g of N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, 33.2g of tripotassium phosphate, and 0.5g of bis(tri-tert-butylphosphine)palladium(0) were added to 300ml of 1,4-dioxane and 100ml of water, and then refluxed for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 33g of compound 31-2. (Yield 72%). MS[M+H]+=810

[0393] 3) Synthesis of compound BD1 In a nitrogen atmosphere, 25 g of compound 31-2 and 20.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.2 g of BD1 was obtained by recrystallization (yield 29%). MS [M+H]+ = 818

[0394] Synthesis Example 32. Synthesis of compound BD2 [ka]

[0395] 1) Synthesis of compound 32-1 Instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 3-bromo-5-chloro-1,1'-biphenyl and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-2-amine were used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-1. After extraction, 49.2 g of compound 32-1 was obtained by recrystallization. (Yield 76%). MS[M+H]+=579

[0396] 2) Synthesis of compound 32-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 32-1, 4-((4-(tert-butyl)phenyl)amino)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 30.1 g of compound 32-2 was obtained by recrystallization. (Yield 74%). MS[M+H]+=784

[0397] 3) Synthesis of compound 32-3 In a nitrogen atmosphere, 25 g of compound 32-2 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 7.5 g of compound 32-3 (yield 30%). MS [M+H]+ = 792

[0398] 4) Synthesis of compound 32-4 Compound 32-3 27.7g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonylfluoride 2.4ml, potassium carbonate 3.7g were added to tetrahydrofuran 70ml and water 30ml, and the mixture was refluxed and stirred for 2 hours. After the reaction was completed, the mixture was extracted and purified by column to obtain 9.1g of compound 32-4 (yield 96%). MS [M+H]+ = 1074

[0399] 5) Synthesis of BD2 In a nitrogen atmosphere, 7g of compound 32-4, 1.84g of bis(4-(tert-butyl)phenyl)amine, 20.11g of pd(dba), 0.19g of Xphos, and 6.4g of cesium carbonate were added to 100ml of xylene and stirred under reflux for 12 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 5.2g of BD2 (76% yield). MS[M+H]+=1055

[0400] Synthesis Example 33. Synthesis of compound BD3 [ka]

[0401] 1) Synthesis of compound 33-1 Compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine was replaced with 3,6-di-tert-butyl-9-(5-chloro-[1,1'-biphenyl]-3-yl- Using 2',3',4',5',6'-d5)-9H-carbazole and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-2-amine, the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 38.2 g of compound 33-1 was obtained by recrystallization. (Yield 78%). MS[M+H]+=771

[0402] 2) Synthesis of BD3 In a nitrogen atmosphere, 25 g of compound 33-1 and 21.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.4 g of BD3 was obtained by recrystallization (yield 29%). MS [M+H]+ = 779

[0403] Synthesis Example 34. Synthesis of compound BD4 [ka]

[0404] 1) Synthesis of compound 34-1 Under a nitrogen atmosphere, 30g of 3-bromo-5-chloro-1,1'-biphenyl, 43.7g of N1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-N3,N3-diphenylbenzene-1,3-diamine, 32.3g of sodium tert-butoxide, and 1.2g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 2 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 54.3g of compound 34-1. (Yield 75%). MS[M+H]+=648

[0405] 2) Synthesis of compound 34-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 34-1, N-([1,1'-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroanthracen-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 35.2 g of compound 34-2 was obtained by recrystallization. (Yield 75%) MS[M+H]+=1015

[0406] 3) Synthesis of BD4 In a nitrogen atmosphere, 25 g of compound 34-2 and 16.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.5 g of BD4 was obtained by recrystallization (yield 30%). MS [M+H]+ = 1023

[0407] Synthesis Example 35. Synthesis of compound BD5 [ka]

[0408] 1) Synthesis of compound 35-1 Under a nitrogen atmosphere, 30g of 1-bromo-3-chloro-5-methylbenzene, 58.4g of N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,e][1,4]dioxin-2-amine, 32.3g of sodium tert-butoxide, and 1.2g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 2 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 55g of compound 35-1. (Yield 72%). MS[M+H]+=525

[0409] 2) Synthesis of compound 35-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 35-1, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 37.7 g of compound 35-2 was obtained by recrystallization. (Yield 73%). MS[M+H]+=906

[0410] 3) Synthesis of BD5 In a nitrogen atmosphere, 25 g of compound 35-2 and 18.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.7 g of BD5 was obtained by recrystallization (yield 31%). MS [M+H]+ = 914

[0411] Synthesis Example 36. Synthesis of compound BD6 [ka]

[0412] 1) Synthesis of compound 36-1 Under a nitrogen atmosphere, 30g of 2-bromo-4-chlorodibenzo[b,d]furan, 43.2g of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 31g of sodium tert-butoxide, and 1.1g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 61.1g of compound 36-1. (Yield 73%). MS[M+H]+=782

[0413] 2) Synthesis of compound 36-2 30g of compound 36-1, 23.3g of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, 36.6g of tripotassium phosphate, and 0.6g of bis(tri-tert-butylphosphine)palladium(0) were added to 300ml of 1,4-dioxane and 100ml of water, and then refluxed for 6 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 27.1g of compound 36-2. (Yield 79%). MS[M+H]+=889

[0414] 3) Synthesis of compound 36-3 Under a nitrogen atmosphere, 30g of compound 36-2, 43.2g of 2-bromo-9,9-dimethyl-9H-fluorene, 31g of sodium tert-butoxide, and 1.1g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 25.6g of compound 36-3 (yield 78%). MS[M+H]+=1080

[0415] 4) Synthesis of BD6 In a nitrogen atmosphere, 25 g of compound 36-3 and 15.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD6 was obtained by recrystallization (yield 29%). MS [M+H]+ = 1088

[0416] Synthesis Example 37. Synthesis of compound BD7 [ka]

[0417] 1) Synthesis of compound 37-1 Instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 9-(tert-butyl)-N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)naphtho[2,3-b]benzofuran-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 31-1. After extraction, 55.3 g of compound 37-1 was obtained by recrystallization. (Yield 72%). MS[M+H]+=629

[0418] 2) Synthesis of compound 37-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 37-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 27.2 g of compound 37-2 was obtained by recrystallization. (Yield 78%). MS[M+H]+=792

[0419] 3) Synthesis of compound 37-3 Instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 27g of compound 37-2 and 10.4g of 4-bromo-1,1'-biphenyl were used, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 31-1. After extraction, 25.1g of compound 37-3 was obtained by recrystallization. (Yield 78%). MS[M+H]+=944

[0420] 4) Synthesis of BD7 In a nitrogen atmosphere, 325g of compound 37-3 and 17.6g of boron triiodide were added to 250ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.1g of BD7 was obtained by recrystallization (yield 28%). MS[M+H]+=952

[0421] Synthesis Example 38. Synthesis of compound BD8 [ka]

[0422] 1) Synthesis of compound 38-1 Instead of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, bis(9,9-dimethyl-9H-fluoren-3-yl)amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 31-1. After extraction, 49.5 g of compound 38-1 was obtained by recrystallization. (Yield 75%) MS[M+H]+=589

[0423] 2) Synthesis of compound 38-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 38-1, 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 31.2 g of compound 38-2 was obtained by recrystallization. (Yield 74%). MS[M+H]+=832

[0424] 3) Synthesis of BD8 In a nitrogen atmosphere, 25 g of compound 38-2 and 20.0 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD8 was obtained by recrystallization (yield 29%). MS [M+H] + = 840

[0425] Synthesis Example 39. Synthesis of compound BD9 [ka]

[0426] 1) Synthesis of compound 39-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 4-bromo-2-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N4,N4-diphenylbenzene-1,4-diamine were used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-1. After extraction, 55 g of compound 39-1 was obtained by recrystallization. (Yield 77%). MS[M+H]+=670

[0427] 2) Synthesis of compound 39-2 Instead of compound 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 39-1,3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 31.2 g of compound 39-2 was obtained by recrystallization. (Yield 76%). MS[M+H]+=913

[0428] 3) Synthesis of BD9 In a nitrogen atmosphere, 25 g of compound 39-2 and 18.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD9 was obtained by recrystallization (yield 29%). MS [M+H] + = 921

[0429] Synthesis Example 40. Synthesis of compound BD10 [ka]

[0430] 1) Synthesis of compound 40-1 Compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine was replaced with 2-chloro-N,N-bis(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)dibenzo[b,d]furan-4-amine and 1-(4,4,5,5-tetramethyl)-1,3,2-dioxaborolan-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 28g of compound 40-1 was obtained by recrystallization. (Yield 75%). MS[M+H]+=930

[0431] 2) Synthesis of BD10 In a nitrogen atmosphere, 25 g of compound 40-1 and 17.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.1 g of BD10 was obtained by recrystallization (yield 28%). MS [M+H] + = 938

[0432] Synthesis Example 41. Synthesis of Compound BD11 [ka]

[0433] 1) Synthesis of compound 41-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan,N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 3-bromo-1-chlorodibenzo[b,d]thiophene, di([1,1'-biphenyl]-4-yl)amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-1. After extraction, 41.4g of compound 41-1 was obtained by recrystallization. (Yield 72%). MS[M+H]+=539

[0434] 2) Synthesis of compound 41-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 41-1, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[b]carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 28.8 g of compound 41-2 was obtained by recrystallization. (Yield 72%). MS[M+H]+=720

[0435] 3) Synthesis of BD11 In a nitrogen atmosphere, 25 g of compound 41-2 and 23.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.6 g of BD11 was obtained by recrystallization (yield 30%). MS [M+H] + = 728

[0436] Synthesis Example 42. Synthesis of compound BD12 [ka]

[0437] 1) Synthesis of compound 42-1 30g of 3-bromo-5-chlorophenol, 37.2g of 9,9-diphenyl-9,10-dihydroacridine, 42g of sodium tert-butoxide, and 1.5g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 1 hour. After the reaction was completed, the mixture was extracted and recrystallized to obtain 51g of compound 42-1 (yield 77%). MS[M+H]+=461

[0438] 2) Synthesis of compound 42-2 30g of compound 42-1, 31.7g of 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole, 49.8g of triphosphatase, and 0.8g of bis(tri-tert-butylphosphine)palladium(0) were added to 300ml of 1,4-dioxane and 100ml of water, and then refluxed for 2 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 32.3g of compound 42-2. (Yield 73%). MS[M+H]+=682

[0439] 3) Synthesis of compound 42-3 In a nitrogen atmosphere, 25 g of compound 42-2 and 24.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 7.3 g of compound 42-3 (yield 29%). MS [M+H]+ = 690

[0440] 4) Synthesis of compound 42-4 Compound 42-3 7g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyLfluoride 2.8ml, potassium carbonate 4.3g were added to tetrahydrofuran 70ml and water 30ml, and then refluxed and stirred for 2 hours. After the reaction was completed, extraction was performed and 9.1g of compound 42-4 was obtained by column purification (yield 92%). MS [M+H] + = 972

[0441] 5) Synthesis of BD12 In a nitrogen atmosphere, 7g of compound 42-4, 2.1g of bis(4-(tert-butyl)phenyl)amine, 20.13g of pd(dba), 0.21g of Xphos, and 7.1g of cesium carbonate were added to 100ml of xylene and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed and 5.1g of BD12 was obtained by recrystallization (yield 74%). MS[M+H]+=953

[0442] Synthesis Example 43. Synthesis of compound BD13 [ka]

[0443] 1) Synthesis of compound 43-1 Instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 3-bromo-5-chloro-1,1'-biphenyl and 3,6-di(adamantan-1-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole were used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-1. After extraction, 51 g of compound 43-1 was obtained by recrystallization. (Yield 73%). MS[M+H]+=623

[0444] 2) Synthesis of compound 43-2 Compound 43-1 was used instead of compound 36-1, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 36-2. After extraction, 27.3 g of compound 43-2 was obtained by recrystallization (yield 78%). MS [M+H]+ = 730

[0445] 3) Synthesis of compound 43-3 Under a nitrogen atmosphere, 27g of compound 43-2, 10.4g of 4-bromo-1,1'-biphenyl, 32.3g of sodium tert-butoxide, and 1.2g of bis(tri-tert-butylphosphine)palladium(0) were added to 600ml of toluene and refluxed for 2 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 25.4g of compound 43-3 (yield 78%). MS[M+H]+=882

[0446] 4) Synthesis of BD13 In a nitrogen atmosphere, 25 g of compound 43-3 and 18.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD13 was obtained by recrystallization (yield 29%). MS [M+H] + = 890

[0447] Synthesis Example 44. Synthesis of compound BD14 [ka]

[0448] 1) Synthesis of compound 44-1 Compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine was replaced with 3,6-di-tert-butyl-9-(5-chloro-[1,1'-biphenyl]-3-yl- Using 2',3',4',5',6'-d5)-9H-carbazole and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-2-amine, the reaction was completed using the same equivalent amount and method as in the synthesis of compound 31-2. After extraction, 38.2 g of compound 44-1 was obtained by recrystallization. (Yield 78%). MS[M+H]+=771

[0449] 2) Synthesis of BD14 In a nitrogen atmosphere, 25 g of compound 44-1 and 21.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.4 g of BD14 was obtained by recrystallization (yield 29%). MS [M+H]+ = 779

[0450] Synthesis Example 45. Synthesis of compound BD15 [ka]

[0451] 1) Synthesis of compound 45-1 Instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 3-bromo-5-chloro-1,1'-biphenyl,9,9-dimethyl-9,10-dihydroacridine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 31-1. After extraction, 34 g of compound 45-1 was obtained by recrystallization. (Yield 77%). MS[M+H]+=396

[0452] 2) Synthesis of compound 45-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 45-1, N-([1,1'-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydroanthracen-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 43.1g of compound 45-2 was obtained by recrystallization. (Yield 75%) MS[M+H]+=764

[0453] 3) Synthesis of BD15 In a nitrogen atmosphere, 25 g of compound 45-2 and 21.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD15 was obtained by recrystallization. (Yield 29%). MS [M+H] + = 772

[0454] Synthesis Example 46. Synthesis of compound BD16 [ka]

[0455] 1) Synthesis of compound 46-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 3-bromo-1-chloronaphthalene and 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole were used, and the reaction was completed using the same equivalent amount and method as in the synthesis of compound 36-1. After extraction, 38.7 g of compound 46-1 was obtained by recrystallization. (Yield 75%). MS[M+H]+=419

[0456] 2) Synthesis of compound 46-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 46-1, N-(9,9-dimethyl)-9H-fluoren-2-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine was used in the same amount and method as in the synthesis process of compound 36-2. After the reaction was completed, extraction was performed, and 43.2 g of compound 46-2 was obtained by recrystallization. (Yield 77%). MS[M+H]+=784

[0457] 3) Synthesis of BD16 In a nitrogen atmosphere, 25 g of compound 46-2 and 21.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD16 was obtained by recrystallization (yield 29%). MS [M+H]+ = 792

[0458] Synthesis Example 47. Synthesis of compound BD17 [ka]

[0459] 1) Synthesis of compound 47-1 Instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 1-bromo-3-(tert-butyl)-5-chlorobenzene 30g and 12,12-dimethyl-5,12-dihydrobenzo[b]acridine 31.4g were used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-1. After extraction, 38.9g of compound 47-1 was obtained by recrystallization. (Yield 75%). MS[M+H]+=427

[0460] 2) Synthesis of compound 47-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 47-1, N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 37.7 g of compound 47-2 was obtained by recrystallization. (Yield 74%). MS[M+H]+=726

[0461] 3) Synthesis of BD17 In a nitrogen atmosphere, 25 g of compound 47-2 and 22.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.2 g of BD17 was obtained by recrystallization (yield 28%). MS [M+H]+ = 734

[0462] Synthesis Example 48. Synthesis of compound BD18 [ka]

[0463] 1) Synthesis of compound 48-1 Instead of 1-bromo-3-chloro-5-methylbenzene, bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine, 3-bromo-5-chloro-1,1'-biphenyl, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)benzo[b]thiophen-3-amine was used, and the same equivalent amount and method were used in the synthesis process of compound 31-1. After the reaction was completed, extraction was performed, and 44 g of compound 48-1 was obtained by recrystallization. (Yield 72%). MS[M+H]+=545

[0464] 2) Synthesis of compound 48-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 48-1, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 31-2. After extraction, 34.2 g of compound 48-2 was obtained by recrystallization. (Yield 71%). MS[M+H]+=870

[0465] 3) Synthesis of BD18 In a nitrogen atmosphere, 25 g of compound 48-2 and 19.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.2 g of BD18 was obtained by recrystallization (yield 29%). MS [M+H]+ = 878

[0466] Synthesis Example 49. Synthesis of compound BD19 [ka]

[0467] 1) Synthesis of compound 49-1 Compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine was replaced with N-(4-(tert-butyl)phenyl)-N-(5-chloro-[1,1'-biphenyl]-3-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[ Using 2,3-b]thiophen-3-amine and 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole in the same amount and method as in the synthesis of compound 31-2, the reaction was completed, and then the product was extracted and recrystallized to obtain 28.9 g of compound 49-1 (yield 73%). MS[M+H]+=760

[0468] 2) Synthesis of BD19 In a nitrogen atmosphere, 25 g of compound 49-1 and 21.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD19 was obtained by recrystallization (yield 29%). MS [M+H] + = 768

[0469] Synthesis Example 50. Synthesis of compound BD20 [ka]

[0470] 1) Synthesis of compound 50-1 Instead of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine was used, and the same equivalent amount and method were used as in the synthesis process of compound 36-1. After the reaction was completed, the compound was extracted and recrystallized to obtain 46.1 g of compound 50-1. (Yield 73%). MS[M+H]+=593

[0471] 2) Synthesis of compound 50-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 50-1, 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-di-o-tolyl-9H-carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 33.2 g of compound 50-2 was obtained by recrystallization. (Yield 73%). MS[M+H]+=904

[0472] 3) Synthesis of BD20 In a nitrogen atmosphere, 25 g of compound 50-2 and 18.4 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.1 g of BD20 was obtained by recrystallization (yield 28%). MS [M+H] + = 912

[0473] Synthesis Example 51. Synthesis of Compound BD21 [ka]

[0474] 1) Synthesis of compound 51-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 3-bromo-1-chloronaphthalene and 5,5,8,8-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophen-3-amine were used in the same amount and method as in the synthesis of compound 36-1. After the reaction was completed, the compound was extracted and recrystallized to obtain 55.5g of compound 51-1. (Yield 72%). MS[M+H]+=621

[0475] 2) Synthesis of compound 51-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 51-1, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 32.4 g of compound 51-2 was obtained by recrystallization. (Yield 71%). MS[M+H]+=946

[0476] 3) Synthesis of BD21 In a nitrogen atmosphere, 25 g of compound 51-2 and 17.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD21 was obtained by recrystallization (yield 29%). MS [M+H] + = 954

[0477] Synthesis Example 52. Synthesis of compound BD22 [ka]

[0478] 1) Synthesis of compound 52-1 Compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine instead of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N-(5-chloro-[1,1'-biphenyl]-3-yl) -5-isopropylbenzo[b]thiophen-3-amine, 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole were used in the same amount and method as in the synthesis of compound 31-2. After the reaction was completed, the compound was extracted and recrystallized to obtain 31.1 g of compound 52-1. (Yield 75%). MS[M+H]+=808

[0479] 2) Synthesis of BD22 In a nitrogen atmosphere, 25 g of compound 52-1 and 20.6 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.3 g of BD22 was obtained by recrystallization (yield 29%). MS [M+H]+ = 816

[0480] Synthesis Example 53. Synthesis of compound BD23 [ka]

[0481] 1) Synthesis of compound 53-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 1-bromo-3-chloronaphthalene and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-3-amine were used, and the same amount and method were used as in the synthesis process of compound 36-1. After the reaction was completed, the compound was extracted and recrystallized to obtain 54.5g of compound 53-1. (Yield 72%). MS[M+H]+=613

[0482] 2) Synthesis of compound 53-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 53-1, 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 31.1 g of compound 53-2 was obtained by recrystallization. (Yield 74%). MS[M+H]+=856

[0483] 3) Synthesis of BD23 In a nitrogen atmosphere, 25 g of compound 53-2 and 19.5 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.1 g of BD23 was obtained by recrystallization (yield 28%). MS [M+H] + = 864

[0484] Synthesis Example 54. Synthesis of compound BD24 [ka]

[0485] 1) Synthesis of compound 54-1 Instead of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan-3-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-1. After extraction, 54g of compound 54-1 was obtained by recrystallization. (Yield 78%). MS[M+H]+=653

[0486] 2) Synthesis of compound 54-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 54-1, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)phenol, the same equivalent amount and method were used as in the synthesis process of compound 36-2. After the reaction was completed, the compound 54-2 was extracted and recrystallized to obtain 32.2 g of compound 54-2. (Yield 77%). MS[M+H]+=912

[0487] 3) Synthesis of compound 54-3 In a nitrogen atmosphere, 25 g of compound 54-2 and 18.3 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 7.3 g of compound 54-3 (yield 29%). MS [M+H]+ = 920

[0488] 4) Synthesis of compound 54-4 Compound 54-3 7g, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride 2.1ml, potassium carbonate 3.2g were added to tetrahydrofuran 70ml and water 30ml, and the mixture was refluxed and stirred for 2 hours. After the reaction was completed, the mixture was extracted and purified by column to obtain compound 54-4 8.8g (yield 96%). MS [M+H]+ = 1201

[0489] 5) Synthesis of BD24 In a nitrogen atmosphere, 7g of compound 54-4, 1.7g of bis(4-(tert-butyl)phenyl)amine, 0.11g of pd(dba)2, 0.18g of Xphos, and 5.7g of cesium carbonate were added to 100ml of xylene and stirred under reflux for 12 hours. After the reaction was completed, the mixture was extracted and recrystallized to obtain 5.1g of BD24 (yield 74%). MS[M+H]+=1183

[0490] Synthesis Example 55. Synthesis of compound BD25 [ka]

[0491] 1) Synthesis of compound 55-1 Instead of 2-bromo-4-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, 1-bromo-3-chloro-9,9-dimethyl-9H-fluorene and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1,1,5,5,8,8-hexamethyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-3-amine were used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-1. After extraction, 52 g of compound 55-1 was obtained by recrystallization. (Yield 76%). MS[M+H]+=705

[0492] 2) Synthesis of compound 55-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 55-1, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 27.7 g of compound 55-2 was obtained by recrystallization. (Yield 73%). MS[M+H]+=886

[0493] 3) Synthesis of BD25 In a nitrogen atmosphere, 25 g of compound 55-2 and 18.8 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.5 g of BD25 was obtained by recrystallization (yield 30%). MS [M+H] + = 894

[0494] Synthesis Example 56. Synthesis of Compound BD26 [ka]

[0495] 1) Synthesis of compound 56-1 Instead of N1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-N3,N3-diphenylbenzene-1,3-diamine, 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophen-3-amine was used, and the same equivalent amount and method were used as in the synthesis process of compound 34-1. After the reaction was completed, extraction was performed, and 44 g of compound 56-1 was obtained by recrystallization. (Yield 75%). MS[M+H]+=525

[0496] 2) Synthesis of compound 56-2 Instead of compound 31-1, N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, compound 56-1, 2-(tert-butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-benzo[b]carbazole was used in the same amount and method as in the synthesis process of compound 31-2. After the reaction was completed, the product was extracted and recrystallized to obtain 31.1 g of compound 56-2. (Yield 71%). MS[M+H]+=762

[0497] 3) Synthesis of BD26 In a nitrogen atmosphere, 25 g of compound 56-2 and 21.9 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.2 g of BD26 was obtained by recrystallization (yield 29%). MS [M+H]+ = 770

[0498] Synthesis Example 57. Synthesis of compound BD27 [ka]

[0499] 1) Synthesis of compound 57-1 Instead of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)benzene-1,3-diamine, bis(4-(tert-butyl)phenyl)amine was used, and the same equivalent amount and method as in the synthesis process of compound 36-1 were used. After the reaction was completed, extraction was performed, and 37 g of compound 57-1 was obtained by recrystallization. (Yield 72%). MS[M+H]+=483

[0500] 2) Synthesis of compound 57-2 Instead of compound 36-1, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-amine, compound 57-1, N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-amine was used, and the reaction was completed using the same equivalent amount and method as in the synthesis process of compound 36-2. After extraction, 35.2 g of compound 57-2 was obtained by recrystallization. (Yield 72%). MS[M+H]+=788

[0501] 3) Synthesis of BD27 In a nitrogen atmosphere, 25 g of compound 57-2 and 21.1 g of boron triiodide were added to 250 ml of 1,2-dichlorobenzene and stirred at 160°C for 4 hours. After the reaction was completed, extraction was performed and 7.6 g of BD27 was obtained by recrystallization (yield 30%). MS [M+H]+ = 796

[0502] [Example]

[0503] Example 1 A glass substrate coated with a 150 nm-thick thin film of ITO (Indium Tin Oxide) was placed in distilled water containing detergent and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was washed for 30 minutes, then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was completed, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and the substrate was dried and transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using nitrogen plasma, and then transferred to a vacuum deposition device.

[0504] On the ITO transparent electrode thus prepared, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Then, HTL1 was thermally vacuum deposited to a thickness of 100 nm to form a first hole transport layer, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a second hole transport layer. Next, the following compound BD1 as a dopant and compound BH1 as a host (weight ratio 5:95) were simultaneously vacuum deposited to form a 20 nm thick light emitting layer. Then, ETL1 was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was vapor deposited to a thickness of 100 nm to form a cathode, and an organic light emitting device was produced.

[0505] In the above process, the deposition rate of the organic material was maintained at 0.04 to 0.09 nm / sec, the deposition rate of lithium fluoride for the electron transport layer was maintained at 0.03 nm / sec, and the deposition rate of aluminum for the cathode was maintained at 0.2 nm / sec. The degree of vacuum during deposition was 1×10 -7 ~5×10- 5 The organic light-emitting device was fabricated while maintaining the pressure at torr.

[0506] [ka]

[0507] Examples 2 to 97 An organic light-emitting device was produced in the same manner as in Example 1, except that in Example 1, compounds BH2 to BH30 were used instead of BH1 as the host compound in the light-emitting layer, and compounds BD2 to BD27 were used instead of BD1 as the dopant compound.

[0508] [ka] [ka] [ka] [ka] [ka]

[0509] Comparative Examples 1 to 15 An organic light emitting device was fabricated in the same manner as in Example 1, except that compounds BHA to BHC were used instead of BH1 as the host compound in the light emitting layer, and BDA to BDD were used instead of BD1 as the dopant compound.

[0510] [ka] [ka]

[0511] The organic light-emitting devices manufactured in the above examples and comparative examples were 2 The driving voltage and efficiency were measured at a current density of 20mA / cm 2 The time (T95) required for the luminance to reach 95% of the initial luminance was measured at a current density of 100 Hz. The results are shown in Table 1 below. [Table 1] [Table 1] [Table 2] [Table 3] [Table 4] [Table 5]

[0512] As can be seen from Table 1, the devices of Examples 1 to 97 containing both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H of the present invention have low voltage, high efficiency and long life characteristics. In particular, the devices containing only one of Chemical Formula 1 and Chemical Formula H of the present invention (Comparative Examples 4 to 15) exhibit the same and / or inferior characteristics compared to the devices not containing Chemical Formula 1 and Chemical Formula H (Comparative Examples 1 to 3), while the devices containing both Chemical Formula 1 and Chemical Formula H of the present invention (Examples 1 to 97) exhibit excellent characteristics.

Claims

1. an anode; a cathode; and an organic layer disposed between the anode and the cathode; the organic layer includes a light-emitting layer, The light-emitting layer contains a compound represented by any one of the following chemical formulas 1-2-1 to 1-2-4; and a compound represented by the following chemical formula H. [Chemical formula 1-2-1] 【Chemistry 41】 [Chemical formula 1-2-2] 【Chemistry 42】 [Chemical formula 1-2-3] 【Chemistry 43】 [Chemical formula 1-2-4] 【Chemistry 44】 In the above chemical formulas 1-2-1 to 1-2-4, R'5 to R'8 are the same or different and each independently represents hydrogen; deuterium; an unsubstituted alkyl group; or an amine group substituted or unsubstituted with a phenyl group substituted with an unsubstituted alkyl group; Ar'2 is an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, Z1 to Z3 are the same or different and each independently represents hydrogen; deuterium; an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring or heterocycle which are bonded to adjacent groups and have 6 to 30 carbon atoms; X1 is O or S; X3 is CRR', where R and R' are the same or different and each independently represents an unsubstituted alkyl group; y2 is 0 and Y2 is a direct bond; A2 is an unsubstituted aromatic hydrocarbon ring; A11 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Ar'1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; or 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, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, G7, G10 to G12, and G14 are the same or different and each independently represents hydrogen; deuterium; an unsubstituted alkyl group; or an unsubstituted arylalkyl group; g7 is an integer of 1 to 4, g10 is an integer of 1 to 8, and g14 is 1 or 2; When g7, g10, g15 and g16 each are 2 or more, the two or more substituents in the brackets are the same or different from each other, When g14 is 2, the substituents in the two brackets are the same or different from each other, [Chemical formula H] 【Chemistry 2】 In the above chemical formula H, L20 and L21 are the same or different and each independently represents a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium; Ar20 and Ar21 are the same or different, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with deuterium; or a polycyclic heterocyclic group having 2 to 30 carbon atoms, which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with deuterium, or a heterocyclic group having 2 to 20 carbon atoms, which is substituted or unsubstituted with deuterium; At least one of Ar20 and Ar21 is a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a deuterium-substituted or unsubstituted polycyclic heterocyclic group having 2 to 30 carbon atoms, R200 and R201 are the same or different, and each independently represents hydrogen; or deuterium; r201 is an integer of 1 to 7, and when r201 is 2 or more, the two or more R201's are the same or different.

2. The organic light-emitting device according to claim 1, wherein adjacent groups among Z1 to Z3 are bonded to each other to form a ring represented by the following chemical formula C-1 or C-2: [Chemical formula C-1] 【Chemistry 50】 [Chemical formula C-2] 【Chemistry 51】 In the above chemical formulas C-1 and C-2, J1 is O; W1 to W8 and Q7 to Q11 are the same or different and each independently represents hydrogen or deuterium; * denotes a bond site to any one of the above chemical formulas 1-2-1 to 1-2-4.

3. The organic light-emitting device according to claim 1 or 2, wherein at least one of Ar20 and Ar21 is represented by the following chemical formula Het1: [Chemical formula Het1] 【Chemistry 52】 In the above formula Het1, The dotted line connects to the formula H, M1 is O; R11 is hydrogen; deuterium; an unsubstituted aryl group; or an unsubstituted heterocyclic group; r11 is an integer of 0 to 7, and when r11 is 2 or more, R11 are the same or different.

4. The organic light-emitting device according to claim 3, wherein the chemical formula Het1 is represented by any one of the following chemical formulas Het2 to Het3: [Chemical formula Het2] 【Chemistry 53】 [Chemical formula Het3] 【Chemical 54】 In the above chemical formulas Het2 to Het3, The dotted line and M1 are defined as those in the formula Het1. R11 is hydrogen; deuterium; an unsubstituted aryl group; or an unsubstituted heterocyclic group; r11' is an integer of 0 to 9, and when r11' is 2 or more, R11 are the same or different.

5. The organic light-emitting device according to any one of claims 1 to 4, wherein the chemical formula H is represented by any one of the following chemical formulas H-1 to H-2: [Chemical formula H-1] 【Chemistry 56】 [Chemical formula H-2] 【Chemistry 57】 In the chemical formulas H-1 to H-2, L20, L21, R200, R201 and r201 are as defined in formula H above; M1 is O; Ar20 and Ar21 are the same or different and each independently represents an unsubstituted aryl group; R11 are the same or different, and each independently represents hydrogen; deuterium; an unsubstituted aryl group; or an unsubstituted heterocyclic group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; Each of r11 and r12 is an integer of 0 to 7, and when each of r11 and r12 is 2 or more, the substituents in the parentheses are the same or different.

6. The organic light-emitting device according to claim 1 , wherein the chemical formula H is any one selected from the following compounds: 【Chemical 732】 【Chemical 733】 【Chemical 734】 【Chemical Formula 735】 【Chemical 736】 【Chemical 737】 【Chemical 738】 【Chemical 739】 【Chemistry 740】 【Chemical Formula 741】 【Chemical Formula 742】 【Chemical 743】 【Chemical 744】 【Chemical 745】 【Chemical 746】 【Chemical 747】 【Chemical 748】

7. The organic light-emitting device according to any one of claims 1 to 6, wherein the light-emitting layer contains the compound represented by any one of Chemical Formulas 1-2-1 to 1-2-4; and the compound represented by Chemical Formula H in a weight ratio of 1:99 to 30:70.

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