Organic light emitting device comprising an organic compound

Abstract

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.

Description

Technical Field

[0001] This specification relates to compounds and organic light-emitting devices containing them.

[0002] This application claims priority and benefit to 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] Organic light emission (OLED) generally refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices typically have a structure comprising an anode, a cathode, and an organic material layer between them. In this paper, the organic material layer is usually formed as a multilayer structure of different materials to improve the efficiency and stability of the OLED. For example, the organic material layer can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an OLED structure, holes and electrons are injected into the organic material layer from the anode and cathode, respectively. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons return to the ground state.

[0004] There remains a need to develop new materials for such organic light-emitting devices (OLEDs). Blue OLEDs, in particular, require both high color purity and long lifetime; however, techniques to achieve both simultaneously are insufficient due to instabilities caused by the high energy of blue materials. Recently, thermally active delayed-fluorescence materials with boron-containing core structures have been developed and have attracted attention due to their high efficiency and color purity; however, these materials suffer from a short lifetime due to high triplet energy and a slow reverse intersystem crossing rate. Therefore, there is a need to develop blue OLED materials that simultaneously achieve both high color purity and long lifetime. Summary of the Invention

[0005] Technical issues

[0006] This specification relates to providing organic light-emitting devices that contain organic compounds.

[0007] Technical solution

[0008] One embodiment of this specification provides an organic light-emitting device, the organic light-emitting device comprising an anode; a cathode; and an organic material layer disposed between the anode and the cathode.

[0009] The organic material layer includes a light-emitting layer, and

[0010] The luminescent layer comprises a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula H.

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] A1 is any one of the following: substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted heterocycles, and fused rings.

[0015] R5 through R8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0016] Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or a group bonded to A1 to form a substituted or unsubstituted ring.

[0017] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form a substituted or unsubstituted ring.

[0018] When Ar2 and R5 form benzo[ When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring,

[0019] Z1 to Z3 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or a group bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0020] Ar1 is a phenyl group, A1 is a substituted or unsubstituted benzene group, R6 to R8 are hydrogen atoms, adjacent groups in Z1 to Z3 do not bond to each other to form a substituted or unsubstituted ring, and when Ar2 and R5 simultaneously form an indole group, the indole group is a substituted indole group.

[0021] [Chemical formula H]

[0022]

[0023] In the chemical formula H,

[0024] L20 and L21 may be the same as or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group.

[0025] Ar20 and Ar21 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0026] At least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group.

[0027] R200 and R201 may be the same as or different from each other, and each is independently 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, and

[0028] r201 is an integer from 1 to 7, and when r201 is 2 or greater, two or more R201 are the same or different from each other.

[0029] Beneficial effects

[0030] An organic light-emitting device according to one embodiment of this specification comprises 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 lifetime characteristics. Attached Figure Description

[0031] Figure 1 An organic light-emitting device according to one embodiment of this specification is shown.

[0032] [Figure Labels]

[0033] 1: Base

[0034] 2: Anode

[0035] 3: Emissive layer

[0036] 4: Cathode Detailed Implementation

[0037] This instruction manual will be described in more detail below.

[0038] This specification provides an organic light-emitting device including a light-emitting layer comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula H. Specifically, the compound represented by Chemical Formula 1 is used as a dopant, and the compound represented by Chemical Formula H is used as the host.

[0039] Compared to organic light-emitting devices (OLEDs) using pyrene-based compounds, existing OLEDs using boron-based compounds offer high efficiency but suffer from short lifetimes. However, compounds represented by Formula 1 possess narrow full width at half maximum (FWHM), and OLEDs incorporating these compounds offer advantages in both efficiency and lifetime. Maintaining the narrow FWHM through the hexagonal rings of boron and amine, and filling insufficient boron electrons via direct bonds between boron and amine on opposite sides, increases the stability of the nucleus in the unstable polaron state, thus improving lifetime. Furthermore, by promoting the transition from polaron to exciton states, OLEDs incorporating these compounds exhibit improved efficiency.

[0040] Compounds represented by the chemical formula H exhibit favorable hole and electron migration and injection, which stabilizes the driving voltage and produces a high photoluminescence quantum yield. Therefore, when compounds represented by the chemical formula H are used as the host of the emitting layer in organic light-emitting devices, long lifetime and high efficiency are achieved.

[0041] Throughout this application, the term "combination thereof" as used in the Markush-type representation means a mixture or combination of one or more of the constituent elements described in the Markush-type representation, and means including one or more of the constituent elements.

[0042] Examples of substituents in this specification are described below; however, substituents are not limited thereto.

[0043] In this specification, dashed lines or This refers to the connection site.

[0044] The term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there are no restrictions on the position of substitution, as long as it is the position where the hydrogen atom is replaced (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0045] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium; halogen group; cyano; alkyl; cycloalkyl; alkoxy; aryloxy; alkylthio; arylthio; alkenyl; haloalkyl; haloalkoxy; arylalkyl; alkylaryl; silyl; boron; amino; aryl; heterocyclic and fused hydrocarbon cycloalcoside, or substituted with two or more substituents linked together from the substituents exemplified above, or without substituents.

[0046] In this specification, the connection of two or more substituents means that the hydrogen of any substituent is connected to another substituent. For example, the connection of two or more substituents may include the connection of a phenyl group and a naphthyl group to form a... The substituents. Furthermore, the connection of three substituents includes not only a continuous (substituent 1)-(substituent 2)-(substituent 3) connection, but also the connection of (substituent 2) and (substituent 3) with (substituent 1). For example, phenyl, naphthyl, and isopropyl can be connected to form... Substituents. When four or more substituents are connected together, the same limitations described above also apply.

[0047] In this specification, "substituted with A1 or A2" includes cases of substitution with A1, cases of substitution with A2, and cases of substitution with both A1 and A2.

[0048] In one embodiment of this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium; halogen group; cyano; alkyl; cycloalkyl; alkoxy; aryloxy; alkylthio; arylthio; alkenyl; haloalkyl; haloalkoxy; arylalkyl; alkylaryl; silyl; boron; amino; aryl; heterocyclic and fused hydrocarbon cycloalcoside, or substituted with two or more substituents linked together from the substituents exemplified above, or without substituents, and

[0049] 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 includes one or more of O, S, N and Si as heteroelements, and the fused hydrocarbon cycloalkyl group has 9 to 90 carbon atoms.

[0050] In this specification, examples of halogen groups may include fluorine, chlorine, bromine, or iodine.

[0051] In this specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30, more preferably 1 to 15; 1 to 10; or 1 to 6. Specific examples may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0052] In this specification, t-Bu means tert-butyl.

[0053] In this specification, cycloalkyl groups are 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 monocyclic or polycyclic with two or more rings. Specific examples of cycloalkyl groups may 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, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, norbornyl, etc.

[0054] In this specification, the alkoxy group can be linear, branched, or cyclic. 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. Specific examples may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0055] In this specification, the alkenyl group can be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples may 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, It includes, but is not limited to, styrene, etc.

[0056] In this specification, alkyl haloide means that, in the definition of alkyl, the hydrogen of the alkyl group is substituted with at least one halogen group.

[0057] In this specification, haloalkoxy means, in the definition of alkoxy, that the hydrogen of the alkoxy group is substituted with at least one halogen group.

[0058] In this specification, the aryl group is not particularly limited, but it may have 6 to 50 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic.

[0059] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30, more preferably 6 to 20. Specific examples of monocyclic aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, etc.

[0060] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30, more preferably 10 to 20. Specific examples of polycyclic aryl groups may include naphthyl, anthraceneyl, phenanthrene, phenylenetriene, pyrene, finadeninyl, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0061] In this specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0062] When the fluorene group is substituted, it may include However, the structure is not limited to this.

[0063] In this specification, "adjacent" groups may mean a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, a substituent spatially closest to the corresponding substituent, or another substituent that substitutes for the atom substituted by the corresponding substituent. For example, two substituents in the ortho position of a benzene ring and two substituents in an aliphatic ring that substitute for the same carbon atom can be interpreted as groups that are "adjacent" to each other.

[0064] In this specification, arylalkyl means alkyl with aryl substitution, and the examples of aryl and alkyl described above can be applied to aryl and alkyl in arylalkyl.

[0065] In this specification, aryloxy means that, in the definition of alkoxy, the alkyl group of the alkoxy group is replaced by an aryl group, and the above description of the aryl group can be applied. Examples of aryloxy groups may include, but are not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthroline, 3-phenanthroline, 9-phenanthroline, etc.

[0066] In this specification, the alkyl group in alkyl thio group is the same as the examples of alkyl groups described above. Specific examples of alkyl thio groups may include, but are not limited to, methyl thio, ethyl thio, tert-butyl thio, hexyl thio, octyl thio, etc.

[0067] In this specification, the aryl group in arylthio group is the same as the examples of aryl groups described above. Specific examples of arylthio groups may include, but are not limited to, phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc.

[0068] In this specification, a heterocyclic group is a group comprising one or more non-carbon atoms (i.e., heteroatoms), and includes aromatic heterocyclic groups or aliphatic heterocyclic groups. Specifically, the heteroatoms may include one or more atoms selected from N, O, S, Si, Se, etc. Aromatic heterocyclic groups may be represented as heteroaryl. The number of carbon atoms in the heterocyclic group is not particularly limited, but may be 2 to 60, preferably 2 to 30, more preferably 2 to 20, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups may include thiophene, furanyl, pyrrole, imidazole, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, naphthobenzofuranyl, naphthobenzothiophene, dibenzothiophenolyl, naphthobenzothiophene, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Zincyl, phenothiazinyl, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzoazasiline group, dihydroindocarbazolyl, spirofluorenzanthryl, spirofluorenthiophenyl, tetrahydronaphthothiophenyl, tetrahydronaphthofuranyl, tetrahydrobenzothiophenyl, tetrahydrobenzofuranyl, etc., but not limited to these.

[0069] In this specification, silane can be alkylsilane, arylsilane, alkylarylsilane, heteroarylsilane, etc. Examples of alkyl groups described above can be used as alkyl silanes; examples of aryl groups described above can be used as aryl silanes; examples of alkyl and aryl groups can be used as alkyl and aryl silanes; and examples of heterocyclic groups can be used as heteroaryl silanes.

[0070] In this specification, the boron group can be -BR 100 R 101 R 100 and R 101 They may be the same as or different from each other, and may be independently selected from hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms. Specific examples of boron groups may include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc.

[0071] In this specification, the amino group may be selected from -NH2; alkylamino; alkylarylamino; arylamino; arylheteroarylamino; alkylheteroarylamino and heteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 60. The arylamino group has 6 to 60 carbon atoms. According to another embodiment, the arylamino group has 6 to 40 carbon atoms. Specific examples of amine groups may include, but are not limited to, methylamine; dimethylamine; ethylamine; diethylamine; phenylamine; naphthylamine; biphenylamine; anthraceneamine; 9-methylanthraylamine; diphenylamine; N-phenylnaphthylamine; xylylamine; N-phenyltolylamine; triphenylamine; N-phenylbiphenylamine; N-phenylnaphthylamine; N-biphenylnaphthylamine; N-naphthylfluorenylamine; N-phenylphenanthreneamine; N-biphenylphenanthreneamine; N-phenylfluorenylamine; N-phenyltriphenylamine; N-phenanthrenefluorenylamine; N-biphenylfluorenylamine; N-(4-(tert-butyl)phenyl)-N-phenylamine; N,N-bis(4-(tert-butyl)phenyl)amine; N,N-bis(3-(tert-butyl)phenyl)amine, etc.

[0072] In this specification, N-alkylarylamine means an amino group in which the N of the amino group is substituted by an alkyl or aryl group. The alkyl and aryl groups in N-alkylarylamine are the same as those in the examples of alkyl and aryl groups described above.

[0073] In this specification, N-arylheteroarylamine means an amino group in which the N of the amino group is substituted with an aryl or heteroaryl group. The aryl and heteroaryl groups in N-arylheteroarylamine are the same as the examples of aryl and heterocyclic groups described above.

[0074] In this specification, N-alkylheteroarylamine means an amino group in which the N of the amino group is substituted by an alkyl or heteroaryl group. The alkyl and heteroaryl groups in N-alkylheteroarylamine are the same as the examples of alkyl and heterocyclic groups described above.

[0075] In this specification, alkylamino means an amino group in which the N of the amino group is alkyl-substituted, and includes dialkylamino, alkylarylamino, and alkylheteroarylamino.

[0076] In this specification, arylamine means an amino group in which the N of the amino group is aryl-substituted, and includes diarylamine, arylheteroarylamine and alkylarylamine.

[0077] In this specification, heteroarylamine means an amino group in which the N of the amino group is substituted with a heteroaryl group, and includes diheteroarylamine, arylheteroarylamine and alkylheteroarylamine.

[0078] In this specification, the cycloalkyl group can be an aromatic cycloalkyl group, an aliphatic cycloalkyl group, or a fused cycloalkyl group of an aromatic cycloalkyl group and an aliphatic cycloalkyl group, and can be selected from examples of cycloalkyl, aryl, and combinations thereof. Examples of cycloalkyl groups may include, but are not limited to, phenyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, tetrahydronaphthyl, tetrahydroanthrayl, 1,2,3,4-tetrahydro-1,4-bridged methylenenaphthyl, 1,2,3,4-tetrahydro-1,4-bridged ethylnaphthyl, etc.

[0079] In this specification, the meaning of "adjacent" in "bonded with an adjacent group to form a ring" is the same as described above, and "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0080] In this specification, the hydrocarbon ring can be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from examples of cycloalkyl, aryl, and combinations thereof, the difference being that the hydrocarbon ring is not monovalent. Examples of hydrocarbon rings may 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-bridged methylenenaphthalene, 1,2,3,4-tetrahydro-1,4-bridged ethylnaphthalene, etc.

[0081] Furthermore, aliphatic hydrocarbon rings include all hydrocarbon rings containing single bonds, non-aromatic hydrocarbon rings containing multiple bonds, or rings having a form of ring fusion containing both single and multiple bonds. Therefore, the single-bonded rings in aliphatic hydrocarbon rings can be selected from examples of cycloalkyl groups, differing in that they are not monovalent groups, and hydrocarbon rings containing single and double bonds but not aromatic rings (e.g., cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, or cyclonorbornene) also belong to aliphatic hydrocarbon rings.

[0082] In this specification, fused hydrocarbon rings (groups) refer to fused rings (groups) of aromatic hydrocarbon rings and aliphatic hydrocarbon rings. For aromatic hydrocarbon rings, the descriptions of aryl groups provided above can be applied; for aliphatic hydrocarbon rings, the descriptions of cycloalkyl groups provided above can be applied. Fused hydrocarbon rings (groups) may have 9 to 90 carbon atoms, preferably 9 to 60 carbon atoms, and more preferably 9 to 30 carbon atoms.

[0083] In this specification, a heterocycle means a ring containing one or more non-carbon atoms (i.e., heteroatoms). Specifically, heteroatoms may include one or more atoms selected from N, O, S, Si, Se, etc. Heterocycles can be monocyclic or polycyclic and can be aromatic heterocycles; aliphatic heterocycles; fused rings of aromatic heterocycles and aliphatic heterocycles; aliphatic hydrocarbon rings, aromatic hydrocarbon rings and fused rings of aromatic heterocycles; or aliphatic hydrocarbon rings, aromatic hydrocarbon rings and fused rings of aliphatic heterocycles, wherein the aromatic heterocycle may be selected from examples of heteroaryl groups, the difference being that it is not monovalent.

[0084] In this specification, aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Aliphatic heterocycles include all aliphatic rings containing single bonds, aliphatic rings containing multiple bonds, or aliphatic rings having a ring-fused form containing both single and multiple bonds. Examples of aliphatic heterocycles may include ethylene oxide, tetrahydrofuran, and 1,4-dioxane. Alkane, pyrrolidine, piperidine, morpholine, oxepane, azokane, thiokane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, tetrahydrobenzofuran, etc., but not limited to these.

[0085] In this specification, “deuteration,” “deuterated,” or “deuterated” means that the hydrogen at the substituted position of the compound is deuterated.

[0086] In this specification, "deuterated by X%", "deuterated by X%", "degree of deuteration by X%", or "rate of deuteration by X%" means that X% of the hydrogens at the substituted positions in the corresponding structure are deuterated. For example, when the corresponding structure is dibenzofuran, "deuterated by 25%", "deuterated by 25%", "degree of deuteration by 25%", or "rate of deuteration by 25%" means that two of the eight hydrogens at the substituted positions in dibenzofuran are deuterated.

[0087] In this specification, the degree of deuteration can be described using known methods such as nuclear magnetic resonance (NMR). 1 It can be determined by H NMR, TLC / MS (thin-layer chromatography / mass spectrometry) or MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[0088] In this specification, the description of a component being placed "on" another component includes not only cases where a component is in contact with another component, but also cases where there is another component between the two components.

[0089] In this specification, unless otherwise stated, a description in which a part "includes" a component means that it may also include other components, and does not exclude other components.

[0090] In this specification, the term "layer" has the same meaning as "film" primarily used in the art, and refers to a coating covering a target area. There is no limitation on the size of a "layer," and individual "layers" may have the same or different dimensions. According to one embodiment, the size of a "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single subpixel.

[0091] In this specification, the meaning of a specific material A being contained in a layer B includes both of the following: i) one or more types of material A being contained in a layer B, and ii) the layer B being formed as one or more layers, and material A being contained in one or more of the multiple layers B.

[0092] In this specification, the meaning of a particular material A being contained in layers C or D includes all of the following: i) being contained in one or more layers of one or more layers C, ii) being contained in one or more layers of one or more layers D, or iii) being contained in each of one or more layers C and one or more layers D.

[0093] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While similar or equivalent methods and materials may be used to implement or test embodiments of this disclosure, suitable methods and materials are described later. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, the definition in this specification shall prevail. Furthermore, materials, methods, and examples are for illustrative purposes only and are not intended to limit this specification.

[0094] The following section will describe the chemical formula 1 in detail.

[0095] [Chemical Formula 1]

[0096]

[0097] In chemical formula 1,

[0098] A1 is any one of the following: substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted heterocycles, and fused rings.

[0099] R5 through R8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0100] Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or a group bonded to A1 to form a substituted or unsubstituted ring.

[0101] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form a substituted or unsubstituted ring.

[0102] When Ar2 and R5 form benzo[ When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring,

[0103] Z1 to Z3 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or a group bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0104] Ar1 is a phenyl group, A1 is a substituted or unsubstituted benzene group, R6 to R8 are hydrogen groups, adjacent groups in Z1 to Z3 do not bond to each other to form a substituted or unsubstituted ring, and when Ar2 and R5 simultaneously form an indole group, the indole group is a substituted indole group.

[0105] According to one embodiment of this 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 amino 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 bonded to an adjacent group to form a substituted or unsubstituted ring, and the remainder is hydrogen.

[0106] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to Ar1 to form any of the following: a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, or a fused ring thereof containing any or more of N, S, O, and Si.

[0107] According to one embodiment of this specification, Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form any of the following: a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, or a fused ring thereof containing any or more of N, S, O, and Si.

[0108] According to one embodiment of this specification, chemical formula 1 is represented by the following chemical formula 1-1.

[0109] [Chemical Formula 1-1]

[0110]

[0111] In chemical formula 1-1,

[0112] R5 to R8, Ar2, and Z1 to Z3 have the same limitations as in Formula 1.

[0113] R1 to R4 may be the same as or different from each other, and each is independently 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 amino 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 a group bonded to an adjacent group to form any one of a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted heterocyclic ring, or a fused ring thereof.

[0114] Ar1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R4 to form a substituted or unsubstituted ring, and

[0115] Ar1 is phenyl, R1 to R4 and R6 to R8 are hydrogen, adjacent groups in Z1 to Z3 do not bond to each other to form substituted or unsubstituted rings, and when Ar2 and R5 simultaneously form an indole group, the indole group is a substituted indole group.

[0116] According to one embodiment of this specification, chemical formula 1 is represented by the following chemical formulas 1-2.

[0117] [Chemical Formula 1-2]

[0118]

[0119] In chemical formulas 1-2,

[0120] R5 to R8, Ar2, and Z1 to Z3 have the same limitations as in Formula 1.

[0121] X1 is CRR', O, or S.

[0122] 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.

[0123] Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused cyclic group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, and

[0124] R and R' may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring.

[0125] According to one embodiment of this specification, chemical formula 1-1 is represented by any one of the following chemical formulas 1-1-1 to 1-1-36.

[0126] [Chemical Formula 1-1-1]

[0127]

[0128] [Chemical Formula 1-1-2]

[0129]

[0130] [Chemical Formula 1-1-3]

[0131]

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

[0133]

[0134] [Chemical Formula 1-1-5]

[0135]

[0136] [Chemical Formula 1-1-6]

[0137]

[0138] [Chemical Formula 1-1-7]

[0139]

[0140] [Chemical Formula 1-1-8]

[0141]

[0142] [Chemical Formula 1-1-9]

[0143]

[0144] [Chemical Formula 1-1-10]

[0145]

[0146] [Chemical Formula 1-1-11]

[0147]

[0148] [Chemical Formula 1-1-12]

[0149]

[0150] [Chemical Formula 1-1-13]

[0151]

[0152] [Chemical Formula 1-1-14]

[0153]

[0154] [Chemical Formula 1-1-15]

[0155]

[0156] [Chemical Formula 1-1-16]

[0157]

[0158] [Chemical Formula 1-1-17]

[0159]

[0160] [Chemical Formula 1-1-18]

[0161]

[0162] [Chemical Formula 1-1-19]

[0163]

[0164] [Chemical Formula 1-1-20]

[0165]

[0166] [Chemical Formula 1-1-21]

[0167]

[0168] [Chemical Formula 1-1-22]

[0169]

[0170] [Chemical Formula 1-1-23]

[0171]

[0172] [Chemical Formula 1-1-24]

[0173]

[0174] [Chemical Formula 1-1-25]

[0175]

[0176] [Chemical Formula 1-1-26]

[0177]

[0178] [Chemical Formula 1-1-27]

[0179]

[0180] [Chemical Formula 1-1-28]

[0181]

[0182] [Chemical Formula 1-1-29]

[0183]

[0184] [Chemical Formula 1-1-30]

[0185]

[0186] [Chemical Formula 1-1-31]

[0187]

[0188] [Chemical Formula 1-1-32]

[0189]

[0190] [Chemical Formula 1-1-33]

[0191]

[0192] [Chemical Formula 1-1-34]

[0193]

[0194] [Chemical Formula 1-1-35]

[0195]

[0196] [Chemical Formula 1-1-36]

[0197]

[0198] In chemical formulas 1-1-1 to 1-1-36,

[0199] X2 to X9 may be the same as or different from each other, and each is independently CRR', NR”, O or S.

[0200] Y1 and Y2 may be the same as or different from each other, and each is independently CG1G2, SiG8G9, NG101, O, or S.

[0201] y1 is either 0 or 1, and when y1 is 0, Y1 is a direct bond.

[0202] y2 is either 0 or 1, and when y2 is 0, Y2 is a direct bond.

[0203] R, R', and R" may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring.

[0204] R'1 to R'8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0205] G1 to G19, G'13, and G101 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form substituted or unsubstituted aromatic hydrocarbon rings; substituted or unsubstituted aliphatic hydrocarbon rings; or fused ring of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings.

[0206] g3, g7, and g15 through g18 are each integers from 1 to 4.

[0207] g4 and g10 are each integers from 1 to 8.

[0208] g13 and g14 are each 1 or 2.

[0209] g'13 is an integer from 0 to 2.

[0210] g19 is an integer from 1 to 3.

[0211] a21 is either 0 or 1.

[0212] When g3, g4, g7, g10 and g15 through g19 are each 2 or larger, the substituents in two or more brackets may be the same or different from each other.

[0213] 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 from each other, and each is independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0214] A2 and A21 may be the same as or different from each other, and each is independently 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.

[0215] Z1 to Z3 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or a group bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0216] In chemical formulas 1-1-4, 1-1-6, 1-1-8, 1-1-12, 1-1-28, and 1-1-32,

[0217] When y2 is 1 and Y2 is 0, G7 and R'6 to R'8 are hydrogen.

[0218] In one embodiment of this 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring, and the remainder is hydrogen.

[0219] According to one embodiment of this specification, chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-6.

[0220] [Chemical Formula 1-2-1]

[0221]

[0222] [Chemical Formula 1-2-2]

[0223]

[0224] [Chemical Formula 1-2-3]

[0225]

[0226] [Chemical Formula 1-2-4]

[0227]

[0228] [Chemical Formula 1-2-5]

[0229]

[0230] [Chemical Formula 1-2-6]

[0231]

[0232] In chemical formulas 1-2-1 to 1-2-6,

[0233] X1, A11, and Z1 to Z3 have the same limitations as in chemical formulas 1-2.

[0234] X3 to X6 may be the same as or different from each other, and each is independently CRR', NR”, O or S.

[0235] Y2 is CG1G2, SiG8G9, NG101, O, or S.

[0236] y2 is either 0 or 1, and when y2 is 0, Y2 is a direct bond.

[0237] 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.

[0238] Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused cyclic group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group.

[0239] R, R', and R" may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring.

[0240] R'5 to R'8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0241] G1, G2, G7 through G12, G14, G15, G16, and G101 are identical or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form a substituted or unsubstituted aromatic ring; a substituted or unsubstituted aliphatic ring; or a fused ring of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings.

[0242] g7, g15, and g16 are each integers from 1 to 4.

[0243] g10 is an integer from 1 to 8.

[0244] g14 is 1 or 2.

[0245] When g7, g10, g15, and g16 are each 2 or larger, the substituents in two or more parentheses may be the same or different from each other.

[0246] When g14 is 2, the substituents in the two brackets are either the same or different from each other, and

[0247] Ar'1 and Ar'2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused cyclic group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0248] According to one embodiment of this specification, in chemical formula 1-1-4,

[0249] Y2 can be CG1G2, SiG8G9, NG101, O, or S, or y2 can be 0 or 1.

[0250] When y2 is 0, Y2 is a direct bond.

[0251] R'1 to R'4 and R'6 to R'8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0252] G7 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring groups of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic groups, and g7 is an integer from 1 to 4.

[0253] Ar'1 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused cyclic group of an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group.

[0254] Z1 to Z3 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, and

[0255] In chemical formula 1-2-2,

[0256] When y2 is 1 and Y2 is 0, G7 and R'6 to R'8 are hydrogen.

[0257] According to one embodiment of this 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused cyclic group of aromatic hydrocarbon rings and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0258] According to one embodiment of this specification, in chemical formula 1-1-4, there is no case where substituents are bonded to each other to form substituted or unsubstituted rings.

[0259] According to one embodiment of this specification, chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-5.

[0260] [Chemical Formulas 1-3]

[0261]

[0262] [Chemical Formulas 1-4]

[0263]

[0264] [Chemical Formulas 1-5]

[0265]

[0266] In chemical formulas 1-3 to 1-5,

[0267] Ar1, Ar2, A1, R5 to R8, and Z1 to Z3 have the same limitations as in Formula 1.

[0268] T1 to T10 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0269] 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, and

[0270] 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 amino group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused cyclic group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group.

[0271] In one embodiment of this specification, at least one of T1 and T2 is a substituent that is not hydrogen.

[0272] In one embodiment of this specification, at least one of T6 and T7 is a substituent that is not hydrogen.

[0273] According to one embodiment of this specification, chemical formula 1 is represented by the following chemical formula 2.

[0274] [Chemical Formula 2]

[0275]

[0276] In chemical formula 2,

[0277] A1, Ar1, and Z1 to Z3 have the same limitations as in Formula 1.

[0278] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R”51 to form any of the following: a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, or a fused ring thereof containing any or more of N, S, O, and Si.

[0279] R”51 and R”5 through R”8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0280] r”51 is 1 or 2, and

[0281] When r”51 is 2, the two R”51 are either the same or different from each other.

[0282] According to one embodiment of this specification, chemical formula 1-1 is represented by the following chemical formula 2-1.

[0283] [Chemical Formula 2-1]

[0284]

[0285] In chemical formula 2-1,

[0286] Ar1, R1 to R4, and Z1 to Z3 have the same limitations as in chemical formula 1-1.

[0287] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R”51 to form any of the following: a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, or a fused ring thereof containing any or more of N, S, O, and Si.

[0288] R”51 and R”5 through R”8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0289] r”51 is 1 or 2, and

[0290] When r”51 is 2, the two R”51 are either the same or different from each other.

[0291] According to one embodiment of this specification, chemical formula 1-2 is represented by the following chemical formula 2-2.

[0292] [Chemical Formula 2-2]

[0293]

[0294] X1, A11, Ar'1, and Z1 to Z3 have the same limitations as in chemical formulas 1-2.

[0295] Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group, or bonded to R”51 to form any of the following: a substituted or unsubstituted aromatic heterocycle, aliphatic heterocycle, or a fused ring thereof containing any or more of N, S, O, and Si.

[0296] R”51 and R”5 through R”8 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring.

[0297] r”51 is 1 or 2, and

[0298] When r”51 is 2, the two R”51 are either the same or different from each other.

[0299] According to one embodiment of this specification, adjacent groups in Z1 to Z3 are bonded to each other to form a ring represented by the following chemical formula C-1 or C-2.

[0300] [Chemical formula C-1]

[0301]

[0302] [Chemical formula C-2]

[0303]

[0304] In chemical formulas C-1 and C-2,

[0305] J1 is O, S, NQ7, CQ8Q9, or SiQ10Q11.

[0306] W1 to W8 and Q7 to Q11 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or a group bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0307] * indicates the site that is bonded to chemical formula 1.

[0308] The adjacent groups in Z1 to Z3 refer to Z1 and Z2; or Z2 and Z3.

[0309] According to one embodiment of this specification, adjacent groups in W1 to W8 are bonded to each other to form a ring represented by the chemical formula C-1.

[0310] According to one embodiment of this specification, chemical formula C-2 is selected from any of the following structures.

[0311]

[0312] In the structure,

[0313] *, W5 to W8 and Q7 to Q11 have the same limitations as described above.

[0314] According to one embodiment of this specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a fused ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

[0315] According to one embodiment of this specification, A1 is an unsubstituted or substituted benzene: a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or NQ1Q2; naphthalene; an unsubstituted or substituted indene, or a linear or branched alkyl group having 1 to 30 carbon atoms; an unsubstituted or substituted indene, or a benzene substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a benzene substituted with a linear or branched alkyl group having 1 to 30 carbon atoms. Fluorene having 1 to 30 carbon atoms in a linear or branched alkyl substituted form; tetrahydronaphthalene having 1 to 30 carbon atoms in an unsubstituted or linearly or branched alkyl substituted form; dibenzofuran having 1 to 30 carbon atoms in an unsubstituted or linearly or branched alkyl substituted form; dibenzothiophene having 1 to 30 carbon atoms in an unsubstituted or linearly or branched alkyl substituted form; monocyclic or polycyclic heterocycles having 2 to 30 carbon atoms in an unsubstituted or linearly or branched alkyl substituted form, or monocyclic or polycyclic aryl substituted form, having 6 to 30 carbon atoms.

[0316] According to one embodiment of this specification, A1 is an unsubstituted or substituted benzene: a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted 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 NQ1Q2; naphthalene; an unsubstituted or substituted linear or branched alkyl group having 1 to 30 carbon atoms. Indene with alkyl substituted form; fluorene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthalene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or monocyclic or polycyclic compounds having 6 to 30 carbon atoms. Aryl-substituted benzofurans; benzothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzonaphthofuran; naphthofuran; benzonaphthothiophene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzonaphthofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrobenzonaphthofuran unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms. Benzonaphthothiophene; unsubstituted or linearly or branched alkyl groups having 1 to 30 carbon atoms of tetrahydrobenzofluorene; unsubstituted or linearly or branched alkyl groups having 1 to 30 carbon atoms of tetrahydronaphthofuran; unsubstituted or linearly or branched alkyl groups having 1 to 30 carbon atoms of tetrahydronaphthothiophene; unsubstituted or linearly or branched alkyl groups having 1 to 30 carbon atoms of naphthothiophene; or unsubstituted or linearly or branched alkyl groups having 1 to 30 carbon atoms of tetrahydrobenzoindene.

[0317] According to one embodiment of this specification, A1 is benzene that is unsubstituted or substituted with methyl, tert-butyl, tetramethyltetrahydronaphthyl, phenyl, or NQ1Q2; naphthalene; indene that is unsubstituted or substituted with methyl; fluorene that is unsubstituted or substituted with methyl; tetrahydronaphthalene that is unsubstituted or substituted with methyl; dibenzofuran that is unsubstituted or substituted with methyl or tert-butyl; dibenzothiophene that is unsubstituted or substituted with methyl, phenyl, or tert-butyl; benzofuran that is unsubstituted or substituted with methyl, phenyl, or tert-butyl. Or tert-butyl substituted benzothiophene; benzonaphthofuran; naphthofuran; unsubstituted or tert-butyl substituted benzonaphthofuran; unsubstituted or methyl substituted tetrahydrobenzonaphthofuran; unsubstituted or methyl substituted tetrahydrobenzonaphthofuran; unsubstituted or methyl substituted tetrahydrobenzofluorene; unsubstituted or methyl substituted tetrahydronaphthofuran; unsubstituted or methyl substituted tetrahydronaphthofuran; unsubstituted or methyl substituted tetrahydronaphthofuran; unsubstituted or methyl substituted naphthofuran; or unsubstituted or methyl substituted tetrahydrobenzoindene.

[0318] According to one embodiment of this specification, Q1 and Q2 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group having 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 that is unsubstituted or substituted 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.

[0319] According to one embodiment of this specification, Q1 and Q2 may be the same as or different from each other, and each independently is methyl; tert-butyl; unsubstituted or methyl- or tert-butyl-substituted phenyl; unsubstituted or methyl- or tert-butyl-substituted biphenyl; unsubstituted or methyl-substituted fluorenyl; unsubstituted or methyl-substituted tetrahydronaphthyl; dibenzofuranyl; or dibenzothiopheneyl.

[0320] According to one embodiment of this specification, R5 to R8 may be the same as or different from each other, and each is independently 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 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 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 heterocyclic ring having 2 to 30 carbon atoms.

[0321] According to one embodiment of this specification, R5 to R8 may be the same as or different from each other, and each is independently 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 bonded to an adjacent group to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; an unsubstituted or linearly or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms. A monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a fused ring having a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, substituted 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.

[0322] According to one embodiment of this specification, R5 to R8 may be the same as or different from each other, and each independently is hydrogen; deuterium; methyl; tert-butyl; phenyl; or NQ3Q4, or bonded to adjacent groups to form unsubstituted or linearly or branched alkyl substituted cyclohexane having 1 to 30 carbon atoms; benzene; unsubstituted or substituted benzofuran having 1 to 30 carbon atoms as linear or branched alkyl, or unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms as monocyclic or polycyclic diarylamine having 6 to 30 carbon atoms; unsubstituted or substituted benzothiophene having 1 to 30 carbon atoms as linear or branched alkyl, or unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms as monocyclic or polycyclic diarylamine having 6 to 30 carbon atoms. Arylamine; naphthofuran; naphthothiophene; indene unsubstituted or substituted with: linear or branched alkyl groups having 1 to 30 carbon atoms, or unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms, of monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms; unsubstituted or substituted with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; indole-indole; unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; tetrahydronaphthofuran unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; tetrahydronaphthothiophene unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; benzodi... Benzene Thioxin; benzodithiain; thiochromene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; chromene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or dihydronaphthalene unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0323] According to one embodiment of this specification, R5 to R8 may be the same as or different from each other, and each independently is hydrogen; deuterium; methyl; tert-butyl; phenyl; or NQ3Q4, or bonded to adjacent groups to form unsubstituted or methyl-substituted cyclohexane; benzene; unsubstituted or methyl, tert-butyl, or unsubstituted or tert-butyl-substituted diphenylamino-substituted benzofuran; unsubstituted or methyl, tert-butyl, or unsubstituted or tert-butyl-substituted diphenylamino-substituted benzothiophene; naphthofuran; naphthothiophene; unsubstituted or methyl, or unsubstituted or tert-butyl-substituted diphenylamino-substituted indene; unsubstituted or phenyl-substituted indole; unsubstituted or methyl-substituted indo-indole; indo-indole; unsubstituted or methyl-substituted tetrahydronaphthofuran; unsubstituted or methyl-substituted tetrahydronaphthothiophene; unsubstituted or methyl-substituted tetrahydrobenzo-indene; benzodi Benzene Thioxin; benzodithiain; unsubstituted or methyl-substituted thiochromene; unsubstituted or methyl-substituted chromene; or unsubstituted or methyl-substituted dihydronaphthalene.

[0324] According to one embodiment of this specification, Q3 and Q4 may be the same as or different from each other, and each independently is an unsubstituted 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, or 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 Q3 and Q4 may be the same as or different from each other, and each independently is an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or bonded to each other to form a ring.

[0325] According to one embodiment of this specification, Q3 and Q4 may be the same as or different from each other, and each is independently methyl; tert-butyl; unsubstituted or methyl- or tert-butyl-substituted phenyl; unsubstituted or methyl- or tert-butyl-substituted biphenyl; unsubstituted or methyl-substituted fluorenyl; unsubstituted or methyl-substituted tetrahydronaphthyl; dibenzofuranyl; or dibenzothiopheneyl, or Q3 and Q4 may be the same as or different from each other, and each is independently unsubstituted or methyl- or tert-butyl-substituted phenyl, or they may be bonded to each other to form a carbazole ring.

[0326] According to one embodiment of this specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a fused ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to Ar1 to form any of the following: a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms and containing any 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.

[0327] According to one embodiment of this specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, either unsubstituted or substituted with any one or more of the following: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; fused-ring groups consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, either unsubstituted or substituted 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 bonded to Al to form any of the following: a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms that is unsubstituted or substituted with any of N, S, O and Si or more thereof; a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms; and fused rings thereof: 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.

[0328] According to one embodiment of this specification, Ar1 is an unsubstituted or substituted phenyl group selected from any one or more of the following: 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 combinations thereof; an unsubstituted or substituted biphenyl group having 1 to 30 carbon atoms; a terphenyl group; an unsubstituted or substituted fluorenyl group having 1 to 30 carbon atoms; an unsubstituted or substituted tetrahydronaphthyl group having 1 to 30 carbon atoms; a dibenzofuranyl group; or a dibenzothiophene group, or a dihydroacridine group bonded to A1 to form an unsubstituted or substituted dihydroacridine group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spiroacridine fluorene; an unsubstituted or substituted dihydroacridine group having 1 to 30 carbon atoms; or a ... Hexahydrocarbazole substituted with branched alkyl groups; dihydrobenzo[a]acrylidine substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, either unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzo[a]acrylidine; spirotetrahydrobenzo[a]acrylidine fluorene; benzofuran[a]indole; benzothiophen[a]indole; dihydrodibenzoazasilane substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirodibenzosiloledibenzoazasilane; phenanthrene Azine; phenothiazine; dihydroindoline substituted 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; or carbazole 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.

[0329] According to one embodiment of this specification, Ar1 is an unsubstituted or substituted phenyl group selected from any or more of methyl, isopropyl, tert-butyl, phenyl, and combinations thereof; an unsubstituted or substituted biphenyl group; a terphenyl group; an unsubstituted or substituted fluorenyl group; an unsubstituted or substituted tetrahydronaphthyl group; a dibenzofuranyl group; or a dibenzothiophene group, or a group bonded to A1 to form an unsubstituted or substituted methyl or phenyl group. Dihydroacrylidine; spiroacrylamide; hexahydrocarbazole, unsubstituted or substituted with any or more of methyl and tert-butyl groups; dihydrobenzoacrylidine, unsubstituted or substituted with methyl or phenyl groups; hexahydrobenzoacrylidine, unsubstituted or substituted with methyl or phenyl groups; spirobenzoacrylidine; spirotetrahydrobenzoacrylamide; benzofuranoindole; benzothienoindole; dihydrodibenzozasilane, unsubstituted or substituted with methyl or phenyl groups; spirodibenzothienodibenzozasilane; phenanthrene Azine; phenothiazine; unsubstituted or methyl- or phenyl-substituted dihydroindoline; benzo[a]carbazole; or unsubstituted or tert-butyl, adamantyl, or phenyl-substituted carbazole.

[0330] According to one embodiment of this specification, Ar2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a fused ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or bonded to R5 to form any of the following: a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms and containing any 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.

[0331] According to one embodiment of this specification, Ar2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, either unsubstituted or substituted with any one or more of the following: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; fused-ring groups consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, either unsubstituted or substituted 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 bonded to R5 to form any of the following: a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms that is unsubstituted or substituted with any of N, S, O and Si or more thereof; a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms; and fused rings thereof: 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.

[0332] According to one embodiment of this specification, Ar2 is an unsubstituted or substituted phenyl group selected from any one or more of the following: 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 combinations thereof; an unsubstituted or substituted biphenyl group having 1 to 30 carbon atoms; a terphenyl group; an unsubstituted or substituted fluorenyl group having 1 to 30 carbon atoms; an unsubstituted or substituted tetrahydronaphthyl group having 1 to 30 carbon atoms; a dibenzofuranyl group; or a dibenzothiophenyl group, or bonded to R5 to form an unsubstituted or substituted linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. The following are listed: dihydroquinoline; spiroquinoline fluorene; unsubstituted or substituted hexahydroindene with a linear or branched alkyl group having 1 to 30 carbon atoms; unsubstituted dihydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; unsubstituted hexahydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophenopyrrole; unsubstituted dihydrobenzozasilane with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirodibenzothiophenobenzozasilane; benzo[…]. Azides; benzothiazides; dihydroindopyrroles that are unsubstituted or substituted 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; benzoindole; or indoles that are 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.

[0333] According to one embodiment of this specification, Ar2 is an unsubstituted or substituted phenyl group selected from any or more of methyl, isopropyl, tert-butyl, phenyl, and combinations thereof; an unsubstituted or substituted biphenyl group; a terphenyl group; an unsubstituted or substituted fluorenyl group; an unsubstituted or substituted tetrahydronaphthyl group; a dibenzofuranyl group; or a dibenzothiophene group, or bonded to R5 to form an unsubstituted or substituted dihydroquinoline group; a spirobenzoquinoline group; an unsubstituted or substituted hexahydroindene group; an unsubstituted or substituted dihydrobenzoquinoline group; an unsubstituted or substituted hexahydrobenzoquinoline group; a spirobenzoquinoline group; a spirotetrahydrobenzoquinoline fluorene group; a benzofuranopyrrole group; a benzothiophene group; an unsubstituted or substituted dihydrobenzoazasilane group; a spirobenzothiophene dibenzoazasilane group; a benzo[…] Azides; benzothiazides; unsubstituted or methyl- or phenyl-substituted dihydroindopyrrole; benzoindole; or unsubstituted or tert-butyl, adamantyl, or phenyl-substituted indoles.

[0334] According to one embodiment of this specification, Z1 to Z3 may be the same as or different from each other, and each independently is hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted; a monocyclic or polycyclic alkyl group having 3 to 30 carbon atoms, substituted or unsubstituted; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted; or NQ5Q6, or forming a monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms, substituted or unsubstituted; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, substituted or unsubstituted.

[0335] According to one embodiment of this specification, Z1 to Z3 may be the same as or different from each other, and each independently is 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; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6, or bonded to an adjacent group to form a monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents 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 cyclic group of an aromatic ring and an aliphatic ring, and combinations thereof.

[0336] According to one embodiment of this specification, Z1 to Z3 may be the same as or different from each other, and each independently is hydrogen; deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; phenyl unsubstituted or substituted with deuterium, or linear or branched alkyl having 1 to 30 carbon atoms; or NQ5Q6, or bonded to an adjacent group to form benzene; indene unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; benzofuran unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; naphthofuran; tetrahydronaphthofuran unsubstituted or substituted with linear or branched alkyl having 1 to 30 carbon atoms; benzothiophene; or indole unsubstituted or substituted with one or more substituents selected from: linear or branched alkyl having 1 to 30 carbon atoms, monocyclic or polycyclic aryl having 6 to 30 carbon atoms, fused cyclic groups of aromatic and aliphatic hydrocarbon rings, and combinations thereof.

[0337] According to one embodiment of this specification, Z1 to Z3 may be the same as or different from each other, and each independently is hydrogen; deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; unsubstituted or deuterated or methylated phenyl; or NQ5Q6, or bonded to an adjacent group to form benzene; unsubstituted or methylated indole; unsubstituted or tert-butylated benzofuran; naphthofuran; unsubstituted or methylated tetrahydronaphthofuran; benzothiophene; or unsubstituted or phenyl- or methyl-substituted tetrahydronaphthyl-substituted indole.

[0338] According to one embodiment of this specification, at least one of Z1 to Z3 is a non-hydrogen substituent, or is bonded to an adjacent group to form a substituted or unsubstituted ring.

[0339] According to one embodiment of this specification, at least one of Z1 to Z3 is a substituent that is not hydrogen.

[0340] According to one embodiment of this 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 alkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or NQ5Q6.

[0341] According to one embodiment of this 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 that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms; or NQ5Q6.

[0342] According to one embodiment of this specification, Z2 is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; an unsubstituted or deuterated, or linearly or branched alkyl-substituted phenyl having 1 to 30 carbon atoms; or NQ5Q6.

[0343] According to one embodiment of this specification, Z2 is deuterium; methyl; isopropyl; tert-butyl; cyclohexyl; unsubstituted or deuterium- or methyl-substituted phenyl; or NQ5Q6.

[0344] According to one embodiment of this specification, Z1 and Z3 are hydrogen.

[0345] According to one embodiment of this specification, Z1 and Z3 are deuterium.

[0346] According to one embodiment of this specification, Q5 and Q6 may be the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group having 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 that is unsubstituted or substituted 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.

[0347] According to one embodiment of this specification, Q5 and Q6 may be the same as or different from each other, and each independently comprises an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms; a fluorenyl group having 1 to 30 carbon atoms; a tetrahydronaphthyl group having 1 to 30 carbon atoms; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0348] According to one embodiment of this specification, Q5 and Q6 may be the same as or different from each other, and each independently is an unsubstituted or methyl-substituted phenyl; an unsubstituted or methyl- or biphenyl-substituted biphenyl; an unsubstituted or methyl-substituted fluorenyl; an unsubstituted or methyl-substituted tetrahydronaphthyl; dibenzofuranyl; or dibenzothiopheneyl.

[0349] According to one embodiment of this 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.

[0350] According to one embodiment of this specification, Z1 and G3 are bonded to each other to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, either unsubstituted or substituted with one or more of the following substituents: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, fused cyclic groups of aromatic and aliphatic hydrocarbon rings, and combinations thereof.

[0351] According to one embodiment of this specification, Z1 and G3 are bonded to each other to form an indole that is unsubstituted or substituted with one or more of the following: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, fused cyclic groups of aromatic and aliphatic hydrocarbon rings, and combinations thereof.

[0352] According to one embodiment of this specification, Z1 and G3 are bonded to each other to form an unsubstituted or phenyl- or methyl-substituted tetrahydronaphthyl-substituted indole.

[0353] According to one embodiment of this specification, A1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, either unsubstituted or substituted with the following: a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group having 6 to 30 carbon atoms, either unsubstituted or substituted 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; or NQ1Q2; a fused ring group having 6 to 30 carbon atoms, either unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or The following are unsubstituted or branched alkyl groups having 1 to 30 carbon atoms, or monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, wherein Q1 and Q2 are the same or different from each other, and each is independently an unsubstituted or branched alkyl group having 6 to 30 carbon atoms substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an unsubstituted or branched alkyl group having 1 to 30 carbon atoms substituted with a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a fused ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, wherein R5 to R8 are the same or different from each other. The same, and each independently being 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 bonded to an adjacent group to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, or an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms; Fused rings of monocyclic or polycyclic aromatic hydrocarbons having 6 to 30 carbon atoms or monocyclic or polycyclic aliphatic hydrocarbons having 3 to 30 carbon atoms, or unsubstituted or substituted monocyclic or polycyclic heterocycles having 2 to 30 carbon atoms: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, or unsubstituted or substituted monocyclic or polycyclic diarylamine groups having 6 to 30 carbon atoms, wherein Q3 and Q4 are the same as or different from each other, and each is independently an unsubstituted or substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms;A fused ring group consisting of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or Q3 and Q4 being the same or different from each other, and each independently being a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or bonded to each other to form a ring, wherein Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted 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 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 with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 2 ... Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; fused-ring groups having 6 to 30 carbon atoms of monocyclic or polycyclic aromatic hydrocarbon rings and monocyclic or polycyclic aliphatic hydrocarbon rings having 3 to 30 carbon atoms, either unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; or monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms, or bonded to Al to form any of the following: unsubstituted or substituted monocyclic or polycyclic aromatic heterocycles having 2 to 30 carbon atoms, monocyclic or polycyclic aliphatic heterocycles having 2 to 30 carbon atoms, and fused-ring groups thereof; linear or branched alkyl groups having 1 to 30 carbon atoms, and monocyclic or polycyclic aliphatic heterocycles having 3 to 30 carbon atoms; A monocyclic or polycyclic cycloalkyl group having 0 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, wherein Ar2 is an unsubstituted or substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms selected from any one or more of the following: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; fused ring groups having 6 to 30 carbon atoms of monocyclic or polycyclic aromatic hydrocarbon rings and monocyclic or polycyclic aliphatic hydrocarbon rings having 3 to 30 carbon atoms, either unsubstituted or substituted with linear or branched alkyl groups having 1 to 30 carbon atoms; or monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms, or bonded to R5 to form any of the following: unsubstituted monocyclic or polycyclic heterocyclic groups. The following are substituted or modified and contain one or more of N, S, O and Si: monocyclic or polycyclic aromatic heterocycles having 2 to 30 carbon atoms, monocyclic or polycyclic aliphatic heterocycles having 2 to 30 carbon atoms, and fused rings thereof: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms, or monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, wherein at least one of Z1 to Z3 is deuterium; linear or branched alkyl groups having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; and monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms that are unsubstituted or substituted with deuterium or linear or branched alkyl groups having 1 to 30 carbon atoms.Alternatively, NQ5Q6, or bonded to adjacent groups to form an unsubstituted or linearly or branched alkyl ring having 1 to 30 carbon atoms, comprising a monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms; or an unsubstituted or substituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, comprising one or more of the following substituents: linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, fused ring groups of aromatic and aliphatic hydrocarbon rings, and combinations thereof, and the remainder being... Hydrogen, Q5, and Q6 may be the same as or different from each other, and each independently is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, either unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a fused ring group having a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms or 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, when Ar2 and R5 form a benzo[a] group; When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. The indole group is a substituted indole group when Ar1 is a phenyl group, A1 is a substituted or unsubstituted benzene group, R6 to R8 are hydrogen groups, adjacent groups in Z1 to Z3 do not bond to each other to form a substituted or unsubstituted ring, and Ar2 and R5 simultaneously form an indole group.

[0354] According to one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently 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 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 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 heterocyclic ring having 2 to 30 carbon atoms.

[0355] According to one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently 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 bonded to adjacent groups to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, comprising a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms that is substituted with an alkyl group; a fused ring having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms that is unsubstituted or substituted 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.

[0356] According to one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each independently is hydrogen; methyl; tert-butyl; phenyl; or NQ3Q4, or bonded to adjacent groups to form unsubstituted or linearly or branched alkyl substituted cyclohexane having 1 to 30 carbon atoms; benzene; unsubstituted or linearly or branched alkyl substituted benzofuran having 1 to 30 carbon atoms; unsubstituted or linearly or branched alkyl substituted benzothiophene having 1 to 30 carbon atoms; naphthofuran; naphthothiophene; unsubstituted or linearly or branched alkyl substituted benzothiophene having 1 to 30 carbon atoms. Indene with linear or branched alkyl substitution of carbon atoms; indole unsubstituted or substituted with monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; indo-indole unsubstituted or substituted with linear or branched alkyl substitution of 1 to 30 carbon atoms; indo-indole; tetrahydronaphthofuran unsubstituted or substituted with linear or branched alkyl substitution of 1 to 30 carbon atoms; tetrahydronaphthothiophene unsubstituted or substituted with linear or branched alkyl substitution of 1 to 30 carbon atoms; tetrahydrobenzo-indole unsubstituted or substituted with linear or branched alkyl substitution of 1 to 30 carbon atoms; benzodi Benzene Thioxin; benzodithiain; unsubstituted or linearly or branched alkyl substituted thiochromene having 1 to 30 carbon atoms; unsubstituted or linearly or branched alkyl substituted chromene having 1 to 30 carbon atoms; or unsubstituted or linearly or branched alkyl substituted dihydronaphthalene having 1 to 30 carbon atoms.

[0357] According to one embodiment of this specification, R1 to R4 may be the same as or different from each other, and each is independently hydrogen; methyl; tert-butyl; phenyl; or NQ3Q4, or bonded to adjacent groups to form unsubstituted or methyl-substituted cyclohexane; benzene; unsubstituted or methyl- or tert-butyl-substituted benzofuran; unsubstituted or methyl- or tert-butyl-substituted benzothiophene; naphthofuran; naphthothiophene; unsubstituted or methyl-substituted indole; unsubstituted or phenyl-substituted indole-indole; indole-indole; unsubstituted or methyl-substituted tetrahydronaphthofuran; unsubstituted or methyl-substituted tetrahydronaphthothiophene; unsubstituted or methyl-substituted tetrahydrobenzoindole; benzodioxane Benzene Thioxin; benzodithiain; unsubstituted or methyl-substituted thiochromene; unsubstituted or methyl-substituted chromene; or unsubstituted or methyl-substituted dihydronaphthalene.

[0358] According to one embodiment of this specification, Q3 and Q4 have the same limitations as described above.

[0359] According to one embodiment of this specification, R4 is bonded to Ar1 to form any of the following: a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, substituted or unsubstituted, and containing any 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.

[0360] According to one embodiment of this specification, R4 is bonded to Ar1 to form any of the following: a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms, unsubstituted or substituted with any of the following and containing N, S, O and Si, a monocyclic or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms, and fused rings thereof: 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.

[0361] According to one embodiment of this specification, R4 is bonded to Ar1 to form an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spiroquinoline fluorene; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a hexahydroindene; an unsubstituted or linearly or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Hexahydrobenzoquinoline; unsubstituted or substituted hexahydrobenzoquinoline with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophene pyrrole; dihydrobenzozasilanes unsubstituted or substituted dihydrobenzozasilanes with a linear or branched alkyl group having 1 to 30 carbon atoms, or with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; spirodibenzothiophene benzozasilane; benzo[…] Azides; benzothiazides; dihydroindopyrroles that are unsubstituted or substituted 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; benzoindole; or indoles that are 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.

[0362] According to one embodiment of this specification, R4 is bonded to Ar1 to form an unsubstituted or methyl- or phenyl-substituted dihydroquinoline; spiroacridinylquinoline; an unsubstituted or substituted hexahydroindene selected from methyl and tert-butyl groups or more; an unsubstituted or methyl- or phenyl-substituted dihydrobenzoquinoline; an unsubstituted or methyl- or phenyl-substituted hexahydrobenzoquinoline; spirobenzoquinoline; spirotetrahydrobenzoquinoline fluorene; benzofuranopyrrole; benzothiophene pyrrole; an unsubstituted or methyl- or phenyl-substituted dihydrobenzozasilane; spirobenzothiopyrrole dibenzozasilane; benzo[…]. Azides; benzothiazides; unsubstituted or methyl- or phenyl-substituted dihydroindopyrrole; benzoindole; or unsubstituted or tert-butyl, adamantyl, or phenyl-substituted indoles.

[0363] According to one embodiment of this specification, chemical formula 1 is selected from any of the following compounds.

[0364]

[0365]

[0366]

[0367]

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[0370]

[0371]

[0372]

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[0375]

[0376]

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[0380]

[0381]

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[0384]

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[0952]

[0953]

[0954]

[0955]

[0956]

[0957]

[0958]

[0959]

[0960]

[0961]

[0962]

[0963]

[0964]

[0965]

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[0967]

[0968]

[0969]

[0970]

[0971]

[0972]

[0973]

[0974]

[0975]

[0976]

[0977]

[0978]

[0979]

[0980]

[0981]

[0982]

[0983]

[0984]

[0985]

[0986]

[0987]

[0988]

[0989]

[0990]

[0991]

[0992]

[0993]

[0994] In the compound, t-Bu is tert-butyl.

[0995] The chemical formula H will be described in detail below.

[0996] [Chemical formula H]

[0997]

[0998] In the chemical formula H,

[0999] L20 and L21 may be the same as or different from each other, and each is an independent direct bond; or a substituted or unsubstituted aryl group.

[1000] Ar20 and Ar21 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[1001] At least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group.

[1002] R200 and R201 may be the same as or different from each other, and each is independently 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, and

[1003] r201 is an integer from 1 to 7, and when r201 is 2 or greater, two or more R201 are the same or different from each other.

[1004] In this specification, even when deuterated substitution is not specified, the chemical formula H may be deuterated.

[1005] In one embodiment of this specification, L20 and L21 may be the same as or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted.

[1006] In one embodiment of this specification, L20 and L21 may be the same as or different from each other and are each independently a direct bond; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted.

[1007] In one embodiment of this specification, L20 and L21 are either unsubstituted or deuterated.

[1008] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is independently a direct bond; an unsubstituted or deuterated phenylene; an unsubstituted or deuterated biphenylene; or an unsubstituted or deuterated naphthylene.

[1009] In one embodiment of this specification, L20 is a direct key.

[1010] In one embodiment of this specification, L21 is a direct bond; an unsubstituted or deuterated phenylene; an unsubstituted or deuterated biphenylene; or an unsubstituted or deuterated naphthylene.

[1011] In one embodiment of this specification, at least one of L20 and L21 is a direct bond.

[1012] In one embodiment of this specification, at least one of L20 and L21 is a substituted or unsubstituted aryl group.

[1013] In one embodiment of this specification, L20 and L21 may be the same as or different from each other, and each is a direct key independently; or selected from any of the following structures.

[1014]

[1015] In the structure,

[1016] The dashed line indicates the position where it connects to the chemical formula H, and

[1017] D stands for deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

[1018] In one embodiment of this specification, k1 is 0.

[1019] In another implementation, k1 is 4.

[1020] In one embodiment of this specification, k2 is 0.

[1021] In another implementation, k2 is 6.

[1022] In one embodiment of this specification, L20 and L21 may each be deuterated.

[1023] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently 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.

[1024] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently 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.

[1025] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms containing O; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms containing S; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms containing N.

[1026] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[1027] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, 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 fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted furanyl group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl 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.

[1028] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each independently represents an unsubstituted or aryl-substituted phenyl group having 6 to 20 carbon atoms; an unsubstituted or aryl-substituted biphenyl group having 6 to 20 carbon atoms; an unsubstituted or aryl-substituted naphthyl group having 6 to 20 carbon atoms; an unsubstituted or aryl-substituted fluorenyl group having 1 to 6 carbon atoms or an aryl-substituted fluorenyl group having 6 to 20 carbon atoms; an unsubstituted or aryl-substituted benzo[a]fluorenyl group having 1 to 6 carbon atoms or an aryl-substituted benzo[a]fluorenyl group having 6 to 20 carbon atoms; or an unsubstituted or aryl-substituted benzo[a]fluorenyl group having 2 to 20 carbon atoms. The heterocyclic-substituted dibenzofuranyl; unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms; unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; or unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, or a benzocarbazoyl group, and Ar20 and Ar21 may each be deuterated.

[1029] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated fluorenyl; or an unsubstituted or deuterated phenyl-substituted benzo[a]benzene. Fluorenyl; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or their deuterated substituents; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl Naphthiobenzofuranyl compounds, substituted with phenyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or their deuterated substituents; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiophenyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or their deuterated substituents; unsubstituted or substituted with deuterium, phenyl, biphenyl, Naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or naphthobenzothiophenyl substituted with a deuterated substituent thereof; unsubstituted carbazoyl or substituted with a deuterated, phenyl, biphenyl, naphthyl, or deuterated substituent thereof; or unsubstituted benzocarbazoyl or substituted with a deuterated, phenyl, biphenyl, naphthyl, or deuterated substituent thereof.

[1030] In one embodiment of this specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group.

[1031] In one embodiment of this 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.

[1032] In one embodiment of this specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted tricyclic or tetracyclic heterocyclic group containing an O heterocyclic group; or a substituted or unsubstituted tricyclic or tetracyclic heterocyclic group containing an S heterocyclic group.

[1033] In one embodiment of this specification, at least one of Ar20 and Ar21 is an O-containing heterocyclic group having 2 to 30 carbon atoms, either substituted or unsubstituted; or an S-containing heterocyclic group having 2 to 30 carbon atoms, either substituted or unsubstituted.

[1034] In one embodiment of this specification, at least one of Ar20 and Ar21 is an O-containing heterocyclic group having 2 to 20 carbon atoms, either substituted or unsubstituted; or an S-containing heterocyclic group having 2 to 20 carbon atoms, either substituted or unsubstituted.

[1035] In one embodiment of this specification, at least one of Ar20 and Ar21 is an O-containing heterocyclic group or an S-containing heterocyclic group, and the heterocyclic group is unsubstituted or substituted by one or more groups selected from the following: deuterium, alkyl and aryl; or a group composed of two or more groups selected from the above groups linked together.

[1036] In one embodiment of this specification, at least one of Ar20 and Ar21 is an O-containing heterocyclic group or an S-containing heterocyclic group, and the heterocyclic group is unsubstituted or substituted with the following: deuterium; alkyl; deuterated alkyl; aryl; deuterated aryl; alkylaryl; deuterated alkylaryl; heterocyclic group; deuterated heterocyclic group; aryl heterocyclic group; or deuterated aryl heterocyclic group.

[1037] In one embodiment of this specification, at least one of Ar20 and Ar21 is a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzothiophenyl.

[1038] In one embodiment of this specification, at least one of Ar20 and Ar21 is represented by the following chemical formula Het1.

[1039] [Chemical formula Het1]

[1040]

[1041] In the chemical formula Het1,

[1042] The dashed line connects to the chemical formula H.

[1043] M1 is either O or S.

[1044] 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 bonded to an adjacent group to form a substituted or unsubstituted ring, and

[1045] r11 is an integer from 0 to 7, and when r11 is 2 or greater, R11 is either the same or different from each other.

[1046] In one embodiment of this specification, M1 is O.

[1047] In one embodiment of this specification, M1 is S.

[1048] In one embodiment of this 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 bonded to an adjacent group to form a substituted or unsubstituted ring.

[1049] In one embodiment of this 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 alkyl 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 bonded to an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

[1050] In one embodiment of this 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 alkyl 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 bonded to an adjacent group to form a substituted or unsubstituted ring having 5 to 30 carbon atoms.

[1051] In one embodiment of this specification, R11 is hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; or a ring having 5 to 30 carbon atoms that is bonded to an adjacent group to form an unsubstituted 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.

[1052] In one embodiment of this specification, R11 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted naphthobenzothiophenyl; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted naphthobenzothiophenyl; substituted or unsubstituted carbazoyl; or substituted or unsubstituted benzocarbazoyl, or bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[1053] In one embodiment of this specification, R11 is hydrogen; deuterium; an unsubstituted or deuterated phenyl group; an unsubstituted or deuterated biphenyl group; an unsubstituted or deuterated terphenyl group; an unsubstituted or deuterated naphthyl group; an unsubstituted or deuterated fluorenyl group; an unsubstituted or deuterated phenyl group; a benzo[a]fluorenyl group; an unsubstituted or deuterated phenyl group; a phenyl group; a fluorenyl ... Biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or dibenzofuranyl substituted with a deuterated substituent thereof; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl, N-phenylcarbazoyl Naphthobenzofuranyl groups substituted with azole, N-biphenylcarbazoyl, or their deuterated substituents; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or their deuterated substituents; unsubstituted or substituted with deuterium, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or their deuterated substituents; The following are substituted with methylfluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, N-phenylcarbazoyl, N-biphenylcarbazoyl, or deuterated substituents thereof; unsubstituted carbazoyl or substituted with deuterium, phenyl, biphenyl, naphthyl, or deuterated substituents thereof; or unsubstituted benzocarbazoyl or substituted with deuterium, phenyl, biphenyl, naphthyl, or deuterated substituents thereof.

[1054] In one embodiment of this specification, r11 is an integer from 0 to 7.

[1055] In one embodiment of this specification, R11 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and r11 is 1 or 2.

[1056] In one embodiment of this specification, the chemical formula Het1 is the following chemical formula Het1-1.

[1057] [Chemical formula Het1-1]

[1058]

[1059] In the chemical formula Het1-1,

[1060] M1, R11, and r11 have the same limitations as those in the chemical formula Het1, and

[1061] One of a1* to a8* is connected to the chemical formula H.

[1062] In one embodiment of this specification, the remainder of a1* to a8* that is not connected to the chemical formula H is R11.

[1063] In one embodiment of this specification, the chemical formula Het1 is represented by any one of the following chemical formulas Het2 to Het4.

[1064] [Chemical formula Het2]

[1065]

[1066] [Chemical formula Het3]

[1067]

[1068] [Chemical formula Het4]

[1069]

[1070] In the chemical formulas Het2 to Het4

[1071] The dashed line and M1 have the same definition as in the chemical formula Het1.

[1072] 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, and

[1073] r11' is an integer from 0 to 9, and when r11' is 2 or greater, R11 is either the same or different from each other.

[1074] In one embodiment of this specification, r11' is an integer from 0 to 7.

[1075] In one embodiment of this specification, R11 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and r11' is 1 or 2.

[1076] In one embodiment of this specification, the chemical formula Het2 is represented by the following chemical formula Het2-1.

[1077] [Chemical formula Het2-1]

[1078]

[1079] In the chemical formula Het2-1,

[1080] M1, R11, and r11' have the same limitations as in the chemical formula Het2, and

[1081] One of a1* to a10* is connected to the chemical formula H.

[1082] In one embodiment of this specification, the chemical formula Het3 is represented by the following chemical formula Het3-1.

[1083] [Chemical formula Het3-1]

[1084]

[1085] In the chemical formula Het3-1,

[1086] M1, R11, and r11' have the same limitations as those in the chemical formula Het3, and

[1087] One of a1* to a10* is connected to the chemical formula H.

[1088] In one embodiment of this specification, the chemical formula Het4 is represented by the following chemical formula Het4-1.

[1089] [Chemical formula Het4-1]

[1090]

[1091] In the chemical formula Het4-1,

[1092] M1, R11, and r11' have the same limitations as in the chemical formula Het4, and

[1093] One of a1* to a10* is connected to the chemical formula H.

[1094] In one embodiment of this specification, the remainder of a1* to a10* that is not connected to the chemical formula H is R11.

[1095] In one embodiment of this specification, a1* is connected to the chemical formula H. In another embodiment, a2* is connected to the chemical formula H. In another embodiment, a3* is connected to the chemical formula H. In another embodiment, a4* is connected to the chemical formula H. In another embodiment, a5* is connected to the chemical formula H. In another embodiment, a6* is connected to the chemical formula H. In another embodiment, a7* is connected to the chemical formula H. In another embodiment, a8* is connected to the chemical formula H. In another embodiment, a9* is connected to the chemical formula H. In another embodiment, a10* is connected to the chemical formula H.

[1096] When the chemical formula Het1 is connected to the chemical formula H via a3* or a4*, the voltage in the device decreases and the efficiency increases.

[1097] In one embodiment of this specification, the chemical formula Het1 can be deuterated.

[1098] In one embodiment of this specification, either Ar20 or Ar21 is a substituted or unsubstituted heterocyclic group, and the other is a substituted or unsubstituted aryl group.

[1099] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each may be a substituted or unsubstituted heterocyclic group independently.

[1100] In one embodiment of this specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[1101] In one embodiment of this specification, Ar20 is a substituted or unsubstituted aryl group, and Ar21 is a substituted or unsubstituted heterocyclic group.

[1102] In one embodiment of this specification, either Ar20 or Ar21 is represented by the chemical formula Het1, and the other is a substituted or unsubstituted aryl group.

[1103] In one embodiment of this specification, either Ar20 or Ar21 is represented by the chemical formula Het1, and the other is a substituted or unsubstituted N-containing heterocyclic group.

[1104] In one embodiment of this specification, Ar20 and Ar21 may be the same as or different from each other, and each is independently represented by the chemical formula Het1.

[1105] In one embodiment of this specification, Ar20 is represented by the chemical formula Het1, and Ar21 is a substituted or unsubstituted aryl group.

[1106] In one embodiment of this specification, Ar20 is represented by the chemical formula Het1, and Ar21 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted N-containing heterocyclic group.

[1107] In one embodiment of this specification, Ar20 is a substituted or unsubstituted aryl group, and Ar21 is represented by the chemical formula Het1.

[1108] In one embodiment of this 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.

[1109] In one embodiment of this specification, the chemical formula H is represented by any one of the following chemical formulas H-1 to H-4.

[1110] [Chemical formula H-1]

[1111]

[1112] [Chemical formula H-2]

[1113]

[1114] [Chemical formula H-3]

[1115]

[1116] [Chemical formula H-4]

[1117]

[1118] In chemical formulas H-1 to H-4,

[1119] L20, L21, R200, R201, and r201 have the same limitations as those in chemical formula H.

[1120] M1 is either O or S.

[1121] M2 is O, S, or NR13.

[1122] Ar20 and Ar21 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group.

[1123] R11 to R13 may be the same as or different from each other, and each is independently 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 bonded to an adjacent group to form a substituted or unsubstituted ring, and

[1124] r11 and r12 are integers from 0 to 7, and when r11 and r12 are 2 or greater, the substituents in parentheses are either the same or different from each other.

[1125] In one embodiment of this specification, the above description of R11 applies to R12.

[1126] In one embodiment of this specification, the above description of r11 applies to r12.

[1127] In one embodiment of this specification, R13 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[1128] In one embodiment of this specification, R13 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[1129] In one embodiment of this specification, R13 is an unsubstituted or deuterated monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[1130] In one embodiment of this specification, R13 is an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; or an unsubstituted or deuterated naphthyl.

[1131] In one embodiment of this 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 alkyl 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.

[1132] In one embodiment of this 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 alkyl 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.

[1133] In one embodiment of this 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.

[1134] In one embodiment of this 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.

[1135] In one embodiment of this specification, R200 is hydrogen; deuterium; a monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted; or a monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms, substituted or unsubstituted.

[1136] In one embodiment of this specification, R200 is hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[1137] In one embodiment of this specification, R200 is hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthraceneyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted finadeninyl; or substituted or unsubstituted fluorenyl.

[1138] In one embodiment of this specification, R200 is hydrogen; deuterium; a phenyl group that is unsubstituted or deuterated, or has a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group that is unsubstituted or deuterated, or has a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthyl group that is unsubstituted or deuterated, or has a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[1139] In one embodiment of this specification, R200 is hydrogen; deuterium; an unsubstituted or deuterium-, phenyl-, or naphthyl-substituted phenyl; biphenyl; or an unsubstituted or deuterium-, phenyl-, or naphthyl-substituted naphthyl.

[1140] In one embodiment of this specification, R200 is an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; or a deuterated naphthyl.

[1141] According to one embodiment of this specification, R201 is hydrogen.

[1142] According to one embodiment of this specification, R201 is deuterium.

[1143] According to one embodiment of this specification, R201 is deuterium, and r201 is 4 or greater.

[1144] According to one embodiment of this specification, R200 and R201 are deuterium, and r201 is 7.

[1145] In one embodiment of this specification, the chemical formula H is represented by the following chemical formula H-5.

[1146] [Chemical formula H-5]

[1147]

[1148] In chemical formula H-5,

[1149] Ar20, Ar21, L20, and L21 have the same limitations as those in chemical formula H, and

[1150] D represents deuterium, and r203 ranges from 0 to 8.

[1151] In one embodiment of this specification, r203 is an integer from 4 to 8.

[1152] In one embodiment of this specification, r203 is 8.

[1153] In one embodiment of this specification, when a compound represented by the chemical formula H is deuterated, 30% or more of the hydrogen atoms at the substituted positions may be deuterated. In another embodiment, in the structure of the chemical formula H, 40% or more of the hydrogen atoms at the substituted positions may be deuterated. In another embodiment, in the structure of the chemical formula H, 60% or more of the hydrogen atoms at the substituted positions may be deuterated. In another embodiment, in the structure of the chemical formula H, 80% or more of the hydrogen atoms at the substituted positions may be deuterated. In yet another embodiment, in the structure of the chemical formula H, 100% of the hydrogen atoms at the substituted positions may be deuterated.

[1154] In one embodiment of this specification, chemical formula H is selected from any of the following compounds.

[1155]

[1156]

[1157]

[1158]

[1159]

[1160]

[1161]

[1162]

[1163]

[1164]

[1165]

[1166]

[1167]

[1168]

[1169]

[1170]

[1171]

[1172] One embodiment of this specification provides an organic light-emitting device comprising the above-described compounds.

[1173] The organic light-emitting device described in this specification includes an anode; a cathode; and an organic material layer disposed between the anode and the cathode, wherein the organic material layer includes a light-emitting layer comprising a compound represented by chemical formula 1 and a compound represented by chemical formula H.

[1174] In one embodiment of this specification, the emissive layer has a maximum emission peak in the range of 400 nm to 500 nm. In other words, the emissive layer emits blue light.

[1175] In one embodiment of this specification, the light-emitting layer comprises a compound represented by Chemical Formula 1 as a dopant and a compound represented by Chemical Formula H as the host of the light-emitting layer. Specifically, the compound represented by Chemical Formula 1 is a blue fluorescent dopant.

[1176] In one embodiment of this specification, the light-emitting layer comprises a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula H in a weight ratio of 1:99 to 30:70. More preferably, the weight ratio is 1:99 to 10:90.

[1177] The luminescent layer may also comprise a host material, which may include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, triazine derivatives, etc., and may include mixtures of two or more of these types; however, the fused aromatic ring derivatives and heterocyclic compounds are not limited to these.

[1178] According to one embodiment of this specification, the organic material layer includes a light-emitting layer comprising a host and one or more types of dopants.

[1179] According to one embodiment of this specification, the organic material layer includes a light-emitting layer comprising a host and two or more types of mixed dopants.

[1180] According to one embodiment of this specification, one or more of the two or more types of mixed dopants comprise Chemical Formula 1, and the main body comprises a compound represented by Chemical Formula H. While one or more of the two or more types of mixed dopants comprise Chemical Formula 1, alternatively, dopant materials known in the art can be used; however, the materials are not limited thereto.

[1181] According to one embodiment of this specification, one or more of the two or more types of mixed dopants include chemical formula 1. Alternatively, one or more of boron-based compounds, pyrene-based compounds, and delayed fluorescence-based compounds different from chemical formula 1 may be used; however, the materials are not limited thereto.

[1182] According to one embodiment of this specification, the organic material layer includes a light-emitting layer, which comprises one or more types of substrates.

[1183] According to one embodiment of this specification, the organic material layer includes a light-emitting layer, which comprises two or more types of hybrid bodies.

[1184] According to one embodiment of this specification, one or more of the two or more types of mixed entities are compounds represented by the chemical formula H.

[1185] According to one embodiment of this specification, the organic material layer includes a light-emitting layer comprising two types of hybrid substrates, the two types of hybrid substrates being different from each other, and the two types of substrates being compounds represented by the chemical formula H.

[1186] The organic material layer of the organic light-emitting device described in this specification can be formed as a single-layer structure, or it can be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of this specification can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited to this, and it can include fewer organic layers.

[1187] In one embodiment of this specification, the organic material layer of the organic light-emitting device further includes one, two or more layers selected from the following: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[1188] In one embodiment of this specification, the two or more organic material layers may be selected from a light-emitting layer, a hole transport layer, a hole injection layer, a layer that performs both hole transport and hole injection, and an electron blocking layer.

[1189] In one embodiment of this specification, the organic light-emitting device may include two or more electron transport layers, but is not limited thereto.

[1190] In one embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more layers of organic material and a cathode are sequentially laminated on a substrate.

[1191] In one embodiment of this specification, the organic light-emitting device can be an inverted organic light-emitting device (OLED) having a reverse structure in which a cathode, one or more layers of organic material and an anode are sequentially laminated on a substrate.

[1192] For example, Figure 1 The structure of an organic light-emitting device according to one embodiment of this specification is shown. Figure 1 Only organic light-emitting devices are shown, and organic light-emitting devices are not limited to this.

[1193] Figure 1 The structure of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially laminated is shown. In such a structure, compounds represented by chemical formula 1 and compounds represented by chemical formula H can be included in the light-emitting layer 3.

[1194] The organic light-emitting device described in this specification can be manufactured using materials and methods known in the art, except that the light-emitting layer of the organic material layer contains a compound represented by chemical formula 1 and a compound represented by chemical formula H.

[1195] When an organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed of the same or different materials.

[1196] For example, the organic light-emitting device of this specification can be fabricated by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. In this document, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using physical vapor deposition (PVD) methods such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and then depositing a material suitable for use as a cathode on the organic material layer. Besides this method, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[1197] Furthermore, in the fabrication of organic light-emitting devices, compounds represented by chemical formula 1 or chemical formula H can be formed into organic material layers using solution coating and vacuum deposition methods. In this document, solution coating refers to, but is not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, and roll coating.

[1198] Besides this method, organic light-emitting devices can also be fabricated by sequentially laminating a cathode material, an organic material layer, and an anode material on a substrate. However, the fabrication method is not limited to this.

[1199] As an anode material, materials with a large work function are generally preferred to facilitate hole injection into the organic material layer. Examples include 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-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[1200] As cathode materials, materials with a small work function are generally preferred to facilitate electron injection into the organic material layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[1201] The luminescent layer may comprise a host material and dopant materials. Host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., however, the materials are not limited to these.

[1202] When the dopant material contains compounds other than those represented by Formula 1, it includes aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted aryl amine groups, and include pyrene, anthracene, etc., containing aryl amine groups. Peryflanthene, etc. Furthermore, styrene amine compounds are compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted aryl amine, and one, two, or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specifically, this includes styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc., however, styrene amine compounds are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[1203] In this specification, when a compound represented by Formula 1 is contained in an organic material layer other than the luminescent layer, or when an additional luminescent layer is provided, the luminescent material of the luminescent layer is a material capable of emitting light in the visible region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and preferably a material with advantageous quantum efficiency for fluorescence or phosphorescence. Examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[1204] A hole injection layer is a layer in which holes from the electrode are injected. The hole injection material is preferably characterized by its ability to transport holes, thus exhibiting an effect of injecting holes from the anode and a superior hole injection effect on the light-emitting layer or light-emitting material. Furthermore, the hole injection material is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. Additionally, materials with excellent thin-film forming capabilities are preferred. Furthermore, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins; oligothiophenes; arylamine-based organic materials; carbazole-based organic materials; nitrile-based organic materials; hexanitrile hexaazabenzophenanthrene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; conductive polymers based on polythiophene, such as anthraquinone or polyaniline; or mixtures of two or more of the above examples, but are not limited thereto.

[1205] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. Preferred hole transport materials are those capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer, and possessing high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers possessing both conjugated and non-conjugated portions.

[1206] The electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. Preferred electron transport materials are those that can advantageously receive electrons from the cathode and move them to the light-emitting layer, and possess high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes; triazine derivatives; LiQ; and others, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in the art. In particular, suitable cathode materials are commonly used materials with low work functions and followed by an aluminum or silver layer. Specifically, these include cesium, barium, calcium, ytterbium, samarium, etc., in each case followed by an aluminum or silver layer.

[1207] The electron injection layer is the layer into which electrons from the electrodes are injected. Preferred electron injection materials are those that possess excellent electron transport capabilities, have the effect of injecting electrons from the cathode, and exhibit excellent electron injection effects on the light-emitting layer or light-emitting material. Furthermore, preferred materials are those that prevent excitons generated in the light-emitting layer from migrating to the hole injection layer and possess excellent thin-film formation capabilities. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, mixtures of two or more of the above examples, etc., but not limited thereto.

[1208] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[1209] An electron blocking layer is a layer that improves device lifetime and efficiency by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without restriction, and the electron blocking layer can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[1210] A hole blocking layer is a layer that prevents holes from passing through the light-emitting layer and reaching the cathode, and it can typically be formed under the same conditions as the electron injection layer. Specific examples include... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, pyridine, pyrimidine, triazine derivatives, etc., but not limited to these.

[1211] Depending on the materials used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-emitting type.

[1212] The compounds according to this specification can also be used in organic light-emitting devices, including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors, etc., based on similar principles. For example, an organic solar cell may have a structure including an anode, a cathode, and a photoactive layer disposed between the anode and the cathode, the photoactive layer of which may contain the compound.

[1213] Invention Embodiments

[1214] The organic light-emitting devices described in this specification can be manufactured using common organic light-emitting device manufacturing methods and materials, the difference being that the above-mentioned compounds are used to form one or more layers of organic material.

[1215] In the following description, this specification will be described in detail with reference to embodiments, comparative examples, etc. However, the embodiments and comparative examples according to this specification can be modified into various other forms, and the scope of this specification should not be construed as limited to the embodiments and comparative examples described below. Embodiments and comparative examples are provided to more fully describe this specification to those skilled in the art.

[1216] Preparation Example 1. Preparation of Compound BH1

[1217]

[1218] Preparation Example 1-1) Preparation of BH1

[1219] In a three-necked flask, compound 1-1 (20.0 g, 60.0 mmol) and dibenzofuran-2-boronic acid (14.0 g, 66.0 mmol) were dissolved in 1,4-dibenzofuran-2-boronic acid. In a alkane (300 ml), K₂CO₃ (24.9 g, 180 mmol) dissolved in H₂O (100 ml) was introduced. Pd(P(t-Bu)₃)₂ (0.68 g, 1.32 mmol) was then introduced, and the mixture was stirred under reflux at an argon atmosphere for 5 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain BH₁ (11.5 g). (Yield 46%, MS [M+H]⁺ = 421)

[1220] Preparation Example 2. Preparation of Compound BH2

[1221]

[1222] Preparation Example 2-1) Preparation of Compound 2-2

[1223] In a three-necked flask, compound 2-1 (20.0 g, 71.0 mmol), bis(pinacol)diboron (27.1 g, 106.6 mmol), and KOAc (20.9 g, 213 mmol) were dissolved in 1,4-dioxanone. In a alkane (300 ml), Pd(dppf)Cl2 (1.09 g, 2.13 mmol) was introduced, and the mixture was stirred under reflux at an argon atmosphere for 8 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain compound 2-2 (18.6 g). (Yield 80%, MS [M+H]+ = 329)

[1224] Preparation Example 2-2) Preparation of Compound 2-3

[1225] In a three-necked flask, compound 2-2 (20.0 g, 60.9 mmol) and compound 1-1 (18.3 g, 54.8 mmol) were dissolved in 1,4-dioxane. In a alkane (300 ml), K₂CO₃ (25.2 g, 183 mmol) dissolved in H₂O (100 ml) was introduced. Pd(dppf)Cl₂ (0.80 g, 1.10 mmol) was then introduced, and the mixture was stirred under reflux at an argon atmosphere for 5 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain compound 2-3 (16.3 g). (Yield 65%, MS [M+H]⁺ = 455)

[1226] Preparation of compound BH2 (Examples 2-3)

[1227] In a three-necked flask, compounds 2-3 (20.0 g, 43.9 mmol) and phenylboronic acid (6.4 g, 52.7 mmol) were dissolved in 1,4-diphenyl ether. In a alkane (200 ml), K₂CO₃ (18.2 g, 132 mmol) dissolved in H₂O (70 ml) was introduced. Pd(P(t-Bu)₃)₂ (0.45 g, 0.88 mmol) was then introduced, and the mixture was stirred under reflux at an argon atmosphere for 5 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain compound BH₂ (14.9 g). (Yield 68%, MS [M+H]⁺ = 497)

[1228] Preparation Example 3. Preparation of Compound BH3

[1229]

[1230] Preparation Example 3-1) Preparation of compound BH3

[1231] Compound BH3 (17.9 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 65%, MS[M+H]+=613)

[1232] Preparation Example 4. Preparation of Compound BH4

[1233]

[1234] Preparation Example 4-1) Preparation of Compound 4-2

[1235] Compound 4-2 (17.1 g) was obtained in the same manner as in Preparation Example 2-1. (Yield 74%, MS[M+H]+=329)

[1236] Preparation of compound 4-3 (Example 4-2)

[1237] Compound 4-3 (14.3 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 57%, MS[M+H]+=455)

[1238] Preparation of compound BH4 (Example 4-3)

[1239] Compound BH4 (14.9 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 68%, MS[M+H]+=497)

[1240] Preparation Example 5. Preparation of Compound BH5

[1241]

[1242] Preparation Example 5-1) Preparation of compound BH5

[1243] Compound BH5 (13.1 g) was obtained in the same manner as in Preparation Example 4-3. (Yield 45%, MS[M+H]+=662)

[1244] Preparation Example 6. Preparation of Compound BH6

[1245]

[1246] Preparation Example 6-1) Preparation of Compound 6-2

[1247] Compound 6-2 (16.6 g) was obtained in the same manner as in Preparation Example 2-1. (Yield 72%, MS[M+H]+=329)

[1248] Preparation Example 6-2) Preparation of Compound 6-3

[1249] Compound 6-3 (15.3 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 61%, MS[M+H]+=455)

[1250] Preparation of compound BH6 (Example 6-3)

[1251] Compound BH6 (14.7 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 68%, MS[M+H]+=497)

[1252] Preparation Example 7. Preparation of Compound BH 7

[1253]

[1254] Preparation Example 7-1) Preparation of Compound 7-3

[1255] Compound 7-3 (16.5 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 64%, MS[M+H]+=532)

[1256] Preparation Example 7-2) Preparation of compound BH 7

[1257] Compound BH7 (14.4 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 67%, MS[M+H]+=573)

[1258] Preparation Example 8. Preparation of Compound BH8

[1259]

[1260] Preparation Example 8-1) Preparation of compound BH 8

[1261] Compound BH8 (12.7 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 52%, MS[M+H]+=471)

[1262] Preparation Example 9. Preparation of Compound BH 9

[1263]

[1264] Preparation Example 9-1) Preparation of Compound 9-2

[1265] Compound 9-2 (18.1 g) was obtained in the same manner as in Preparation Example 2-1. (Yield 72%, MS[M+H]+=329)

[1266] Preparation Example 9-2) Preparation of Compound 9-3

[1267] Compound 9-3 (17.0 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 68%, MS [M+H]+ = 455)

[1268] Preparation of compound BH9 (Example 9-3)

[1269] Compound BH9 (14.7 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 68%, MS[M+H]+=497)

[1270] Preparation Example 10. Preparation of Compound BH 10

[1271]

[1272] Preparation Example 10-1) Preparation of compound BH 10

[1273] Compound BH 10 (16.8 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 68%, MS[M+H]+=471)

[1274] Preparation Example 11. Preparation of Compound BH 11

[1275]

[1276] Preparation Example 11-1) Preparation of Compound 11-1

[1277] Compound 11-1 (18.6 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 71%, MS [M+H]+ = 506)

[1278] Preparation of compound BH11 (Example 11-2)

[1279] Compound BH 11 (14.7 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 68%, MS[M+H]+=497)

[1280] Preparation Example 12. Preparation of Compound BH 12

[1281]

[1282] Preparation Example 12-1) Preparation of Compound 12-2

[1283] Compound 12-2 (18.5 g) was obtained in the same manner as in Preparation Example 2-1. (Yield 74%, MS[M+H]+=329)

[1284] Preparation Example 12-2) Preparation of Compound 12-3

[1285] Compound 12-3 (17.1 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 68%, MS[M+H]+=455)

[1286] Preparation of compound BH12 (Example 12-3)

[1287] Compound BH 12 (13.9 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 64%, MS [M+H]+ = 497)

[1288] Preparation Example 13. Preparation of Compound BH 13

[1289]

[1290] Preparation Example 13-1) Preparation of compound BH 13

[1291] Compound BH 13 (17.0 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 73%, MS [M+H]+ = 587)

[1292] Preparation Example 14. Preparation of Compound BH 14

[1293]

[1294] Preparation Example 14-1) Preparation of compound BH 14

[1295] Compound BH 14 (12.8 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 46%, MS[M+H]+=586)

[1296] Preparation Example 15. Preparation of Compound BH 15

[1297]

[1298] Preparation Example 15-1) Preparation of compound BH 15

[1299] Compound BH 15 (11.8 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 42%, MS[M+H]+=471)

[1300] Preparation Example 16. Preparation of Compound BH 16

[1301]

[1302] Preparation Example 16-1) Preparation of compound BH 16

[1303] Compound BH 16 (11.8 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 42%, MS[M+H]+=471)

[1304] Preparation Example 17. Preparation of Compound BH 17

[1305]

[1306] Preparation Example 17-1) Preparation of compound BH 17

[1307] Compound BH 17 (16.6 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 61%, MS[M+H]+=521)

[1308] Preparation Example 18. Preparation of Compound BH 18

[1309]

[1310] Preparation Example 18-1) Preparation of compound BH 18

[1311] Compound BH 18 (13.5 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 48%, MS[M+H]+=471)

[1312] Preparation Example 19. Preparation of Compound BH 19

[1313]

[1314] Preparation Example 19-1) Preparation of compound BH 19

[1315] Compound BH 19 (12.1 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 43%, MS[M+H]+=471)

[1316] Preparation Example 20. Preparation of Compound BH 20

[1317]

[1318] Preparation Example 20-1) Preparation of Compound 20-2

[1319] Compound 20-2 (19.3 g) was obtained in the same manner as in Preparation Example 2-1. (Yield 85%, MS [M+H]+ = 379)

[1320] Preparation Example 20-2) Preparation of Compound 20-3

[1321] Compound 20-3 (20.8 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 69%, MS [M+H]+ = 506)

[1322] Preparation Example 20-3) Preparation of compound BH 20

[1323] Compound BH 20 (12.4 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 57%, MS[M+H]+=547)

[1324] Preparation Example 21. Preparation of Compound BH 21

[1325]

[1326] Preparation Example 21-1) Preparation of compound BH 21

[1327] Compound BH 21 (13.4 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 47%, MS[M+H]+=471)

[1328] Preparation Example 22. Preparation of Compound BH 22

[1329]

[1330] Preparation Example 22-1) Preparation of compound BH 22

[1331] Compound BH 22 (15.2 g) was obtained in the same manner as in Preparation Example 1-1. (Yield 56%, MS[M+H]+=521)

[1332] Preparation Example 23. Preparation of Compound BH 23

[1333]

[1334] Preparation Example 23-1) Preparation of compound BH 23

[1335] Compound BH₂ (20 g) and TfOH (4 mL) were introduced into C₆D₆ (300 mL) and stirred for 2 hours. After the reaction was complete, D₂O (50 mL) was added, and after stirring the result for 30 minutes, 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 then recrystallized from ethyl acetate to obtain compound BH₂₃ (14.2 g). (Yield 68%, MS[M+H]⁺=521)

[1336] Preparation Example 24. Preparation of Compound BH 24

[1337]

[1338] Preparation Example 24-1) Preparation of Compound 24-1

[1339] d10-anthracene (50.0 g, 265 mmol), N-bromosuccinimide (NBS) (47.3 g, 265 mmol), and dimethylformamide (DMF) (500 mL) were introduced into a two-necked flask and stirred at room temperature under an argon atmosphere for 6 hours. After the reaction was complete, 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. The sample was purified by silica gel column chromatography to obtain compound 24-1 (55.1 g). (Yield 78%, MS [M+H]+ = 267)

[1340] Preparation Example 24-2) Preparation of Compound 24-2

[1341] In a three-necked flask, compound 24-1 (50.0 g, 188 mmol) and naphth-1-ylboronic acid (35.6 g, 207 mmol) were dissolved in 1,4-dioxane. In a alkane (500 ml), K₂CO₃ (77.9 g, 563 mmol) dissolved in H₂O (200 ml) was introduced. Pd(P(t-Bu)₃)₂ (1.92 g, 3.8 mmol) was then introduced, and the mixture was stirred under reflux at an argon atmosphere for 5 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain compound 24-2 (40.5 g). (Yield 82%, MS [M+H]⁺ = 264)

[1342] Preparation Example 24-3) Preparation of Compound 24-3

[1343] Compound 24-2 (20.0 g, 75.9 mmol), N-bromosuccinimide (NBS) (14.9 g, 83.5 mmol), and dimethylformamide (DMF) (300 mL) were introduced into a two-necked flask and stirred at room temperature under an argon atmosphere for 10 hours. After the reaction was complete, 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. The sample was purified by silica gel column chromatography to obtain compound 24-3 (20.1 g). (Yield 77%, MS [M+H]+ = 342)

[1344] Preparation of compound BH 24 (Example 24-4)

[1345] In a three-necked flask, compound 24-3 (20.0 g, 58.6 mmol) and dibenzofuran-2-boronic acid (13.7 g, 64.5 mmol) were dissolved in 1,4-dibenzofuran-2-boronic acid. In a alkane (300 ml), K₂CO₃ (24.3 g, 176 mmol) dissolved in H₂O (100 ml) was introduced. Pd(P(t-Bu)₃)₂ (0.60 g, 1.2 mmol) was then introduced, and the mixture was stirred under reflux at an argon atmosphere for 5 hours. At the end of the reaction, the product was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO₄, filtered, and concentrated. The sample was purified by silica gel column chromatography to obtain compound BH₂₄ (15.9 g). (Yield 63%, MS [M+H]⁺ = 429)

[1346] Preparation Example 25. Preparation of Compound BH 25

[1347]

[1348] Preparation Example 25-1) Preparation of Compound 25-1

[1349] Compound 25-1 (18.2 g) was obtained in the same manner as in Preparation Example 23-1. (Yield 86%, MS[M+H]+=321)

[1350] Preparation Example 25-2) Preparation of Compound 25-2

[1351] Compound 25-2 (17.8 g) was obtained in the same manner as in Preparation Example 24-3. (Yield 72%, MS[M+H]+=399)

[1352] Preparation Example 25-3) Preparation of compound BH 25

[1353] Compound BH 25 (14.3 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 53%, MS[M+H]+=536)

[1354] Preparation Example 26. Preparation of Compound BH 26

[1355]

[1356] Preparation Example 26-1) Preparation of compound BH 26

[1357] Compound BH 26 (12.5 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 50%, MS [M+H]+ = 529)

[1358] Preparation Example 27. Preparation of Compound BH 27

[1359]

[1360] Preparation Example 27-1) Preparation of Compound 27-1

[1361] Compound 27-1 (18.8 g) was obtained in the same manner as in Preparation Example 24-2. (Yield 93%, MS[M+H]+=260)

[1362] Preparation Example 27-2) Preparation of Compound 27-2

[1363] Compound 27-2 (17 g) was obtained in the same manner as in Preparation Example 24-3. (Yield 65%, MS[M+H]+=339)

[1364] Preparation Example 27-3) Preparation of Compound 27-3

[1365] Compound 27-3 (14.4 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 48%, MS[M+H]+=511)

[1366] Preparation Example 27-4) Preparation of compound BH 27

[1367] Compound BH 27 (12.4 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 57%, MS[M+H]+=547)

[1368] Preparation Example 28. Preparation of Compound BH 28

[1369]

[1370] Preparation Example 28-1) Preparation of Compound 28-1

[1371] Compound 28-1 (18.5 g) was obtained in the same manner as in Preparation Example 24-2. (Yield 93%, MS[M+H]+=260)

[1372] Preparation Example 28-2) Preparation of Compound 28-2

[1373] Compound 28-2 (17.9 g) was obtained in the same manner as in Preparation Example 24-3. (Yield 69%, MS[M+H]+=342)

[1374] Preparation of compound BH 28 (Example 28-3)

[1375] Compound BH 28 (11.9 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 42%, MS[M+H]+=479)

[1376] Preparation Example 29. Preparation of Compound BH 29

[1377]

[1378] Preparation Example 29-1) Preparation of compound BH 29

[1379] Compound BH 29 (11.9 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 42%, MS[M+H]+=479)

[1380] Preparation Example 30. Preparation of Compound BH 30

[1381]

[1382] Preparation Example 30-1) Preparation of Compound 30-1

[1383] Compound 30-1 (15.3 g) was obtained in the same manner as in Preparation Example 2-2. (Yield 59%, MS[M+H]+=521)

[1384] Preparation Example 30-2) Preparation of compound BH 30

[1385] Compound BH 30 (14.0 g) was obtained in the same manner as in Preparation Examples 2-3. (Yield 65%, MS [M+H]+ = 562)

[1386] Synthesis Example 31. Synthesis of Compound BD 1

[1387]

[1388] 1) Synthesis of compound 31-1

[1389] Under a nitrogen atmosphere, 1-bromo-3-chloro-5-methylbenzene (30 g), bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine (43.7 g), sodium tert-butoxide (32.3 g), and bis(tri-tert-butylphosphine)palladium (0) (1.2 g) were introduced into toluene (600 ml) and refluxed for 2 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 31-1 (56 g, 75% yield).

[1390] MS[M+H]+=515

[1391] 2) Synthesis of compound 31-2

[1392] Compound 31-1 (30 g), N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine (23.8 g), tripotassium phosphate (33.2 g), and bis(tri-tert-butylphosphine)palladium (0) (0.5 g) were introduced into 1,4-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine (23.8 g), tripotassium phosphate (33.2 g), and bis(tri-tert-butylphosphine)palladium (0) (0.5 g). The mixture was refluxed in alkane (300 ml) and water (100 ml) for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 31-2 (33 g, 72% yield).

[1393] MS[M+H]+=810

[1394] 3) Synthesis of compound BD1

[1395] Compound 31-2 (25 g) and boron triiodide (20.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 1 (7.2 g, yield 29%). MS[M+H]+=818

[1396] Synthesis Example 32. Synthesis of Compound BD 2

[1397]

[1398] 1) Synthesis of compound 32-1

[1399] Using the same equivalences and methods as in the synthesis of compound 31-1, 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 instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 32-1 (49.2 g, 76% yield).

[1400] MS[M+H]+=579

[1401] 2) Synthesis of compound 32-2

[1402] Using the same equivalences and methods as in the synthesis of compound 31-2, compound 32-1 and 4-((4-(tert-butyl)phenyl)amino)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenol were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 32-2 (30.1 g, 74% yield). MS[M+H]+=784

[1403] 3) Synthesis of compound 32-3

[1404] Compound 32-2 (25 g) and boron triiodide (21.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 32-3 (7.5 g, yield 30%). MS[M+H]+=792

[1405] 4) Synthesis of compound 32-4

[1406] Compound 32-3 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.4 mL), and potassium carbonate (3.7 g) were introduced into tetrahydrofuran (70 mL) and water (30 mL), and stirred under reflux for 2 hours. After the reaction was complete, the product was extracted and then purified by column chromatography to obtain compound 32-4 (9.1 g, 96% yield). MS [M+H]+=1074

[1407] 5) Synthesis of BD 2

[1408] Compound 32-4 (7 g), bis(4-(tert-butyl)phenyl)amine (1.84 g), pd(dba)2 (0.11 g), Xphos (0.19 g), and cesium carbonate (6.4 g) were introduced into xylene (100 ml) under a nitrogen atmosphere and stirred under reflux for 12 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD2 (5.2 g, 76% yield). MS[M+H]+=1055

[1409] Synthesis Example 33. Synthesis of Compound BD 3

[1410]

[1411] 1) Synthesis of compound 33-1

[1412] Using the same equivalences and methods as in the synthesis of compound 31-2, 3,6-di-tert-butyl-9-(5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)-9H-carbazole and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)dibenzo[b,d]furan-2-amine were used instead of the compounds. 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were reacted. After the reaction was completed, the product was extracted and then recrystallized to obtain compound 33-1 (38.2 g, yield 78%).

[1413] MS[M+H]+=771

[1414] 2) Synthesis of BD 3

[1415] Compound 33-1 (25 g) and boron triiodide (21.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and recrystallized to obtain BD 3 (7.4 g, yield 29%). MS[M+H]+=779

[1416] Synthesis Example 34. Synthesis of Compound BD 4

[1417] 1) Synthesis of compound 34-1

[1418] Under a nitrogen atmosphere, 3-bromo-5-chloro-1,1'-biphenyl (30 g), N1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-yl)-N3,N3-diphenylphenyl-1,3-diamine (43.7 g), sodium tert-butoxide (32.3 g), and bis(tri-tert-butylphosphine)palladium (0) (1.2 g) were introduced into toluene (600 ml) and refluxed for 2 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 34-1 (54.3 g, yield 75%). MS[M+H]+=648

[1419] 2) Synthesis of compound 34-2

[1420] Using the same equivalences and methods as in the synthesis of compound 31-2, compound 34-1 and N-([1,1'-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9,10-dihydroanthracene-2-amine were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 34-2 (35.2 g, 75% yield). MS[M+H]+=1015

[1421] 3) Synthesis of BD 4

[1422] Under a nitrogen atmosphere, compound 34-2 (25 g) and boron triiodide (16.4 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 4 (7.5 g, yield 30%). MS[M+H]+=1023 Synthesis Example 35. Synthesis of compound BD 5

[1423]

[1424] 1) Synthesis of compound 35-1

[1425] Under a nitrogen atmosphere, 30 g of 1-bromo-3-chloro-5-methylbenzene and N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-yl)dibenzo[b,e][1,4] ... 2-Imine (58.4 g), sodium tert-butoxide (32.3 g), and bis(tri-tert-butylphosphine)palladium (0) (1.2 g) were introduced into toluene (600 ml) and refluxed for 2 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 35-1 (55 g, yield 72%). MS [M+H]+=525

[1426] 2) Synthesis of compound 35-2

[1427] Using the same equivalence and method as in the synthesis of compound 31-2, compound 35-1 and N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-fluorene-2-amine were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 35-2 (37.7 g, 73% yield). MS[M+H]+=906

[1428] 3) Synthesis of BD 5

[1429] Under a nitrogen atmosphere, compound 35-2 (25 g) and boron triiodide (18.4 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 5 (7.7 g, yield 31%). MS[M+H]+=914 Synthesis Example 36. Synthesis of compound BD 6

[1430]

[1431] 1) Synthesis of compound 36-1

[1432] Under a nitrogen atmosphere, 2-bromo-4-chlorodibenzo[b,d]furan (30 g), N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)phenyl-1,3-diamine (43.2 g), sodium tert-butoxide (31 g), and bis(tri-tert-butylphosphine)palladium (0) (1.1 g) were introduced into toluene (600 ml) and refluxed for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 36-1 (61.1 g, yield 73%). MS[M+H]+=782

[1433] 2) Synthesis of compound 36-2

[1434] Compound 36-1 (30 g), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)naphth-2-amine (23.3 g), tripotassium phosphate (36.6 g), and bis(tri-tert-butylphosphine)palladium (0) (0.6 g) were introduced into 1,4-di The mixture was refluxed in alkane (300 ml) and water (100 ml) for 6 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 36-2 (27.1 g, 79% yield).

[1435] MS[M+H]+=889

[1436] 3) Synthesis of compound 36-3

[1437] Compound 36-2 (30 g), 2-bromo-9,9-dimethyl-9H-fluorene (43.2 g), sodium tert-butoxide (31 g), and bis(tri-tert-butylphosphine)palladium (0) (1.1 g) were introduced into toluene (600 ml) under a nitrogen atmosphere and refluxed for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 36-3 (25.6 g, yield 78%). MS [M+H]+=1080

[1438] 4) Synthesis of BD 6

[1439] Under a nitrogen atmosphere, compound 36-3 (25 g) and boron triiodide (15.4 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 6 (7.3 g, yield 29%). MS[M+H]+=1088 Synthesis Example 37. Synthesis of compound BD 7

[1440]

[1441] 1) Synthesis of compound 37-1

[1442] Using the same equivalences and methods as in the synthesis of compound 31-1, 3-bromo-5-chloro-1,1'-biphenyl and 9-(tert-butyl)-N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)naphtho[2,3-b]benzofuran-2-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho-2-yl)amine, after the reaction was completed, the result was extracted and then recrystallized to obtain compound 37-1 (55.3 g, yield 72%). MS[M+H]+=629

[1443] 2) Synthesis of compound 37-2

[1444] Using the same equivalence and method as in the synthesis of compound 31-2, compounds 37-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine were used instead of compounds 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 37-2 (27.2 g, 78% yield).

[1445] MS[M+H]+=792

[1446] 3) Synthesis of compound 37-3

[1447] Using the same equivalences and methods as in the synthesis of compound 31-1, compound 37-2 (27 g) and 4-bromo-1,1'-biphenyl (10.4 g) were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 37-3 (25.1 g, 78% yield). MS[M+H]+=944

[1448] 4) Synthesis of BD 7

[1449] Compound 37-3 (25 g) and boron triiodide (17.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 7 (7.1 g, yield 28%). MS[M+H]+=952

[1450] Synthesis Example 38. Synthesis of Compound BD 8

[1451]

[1452] 1) Synthesis of compound 38-1

[1453] Using the same equivalences and methods as in the synthesis of compound 31-1, 3-bromo-5-chloro-1,1'-biphenyl and bis(9,9-dimethyl-9H-fluoren-3-yl)amine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 38-1 (49.5 g, 75% yield). MS[M+H]+=589

[1454] 2) Synthesis of compound 38-2

[1455] Using the same equivalence and method as in the synthesis of compound 31-2, compound 38-1 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 38-2 (31.2 g, 74% yield).

[1456] MS[M+H]+=832

[1457] 3) Synthesis of BD 8

[1458] Compound 38-2 (25 g) and boron triiodide (20.0 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 8 (7.3 g, yield 29%). MS[M+H]+=840

[1459] Synthesis Example 39. Synthesis of Compound BD 9

[1460] 1) Synthesis of compound 39-1

[1461] Using the same equivalences and methods as in the synthesis of compound 36-1, 4-bromo-2-chlorodibenzo[b,d]furan and N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N4,N4-diphenylphenyl-1,4-diamine were used 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)phenyl-1,3-diamine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 39-1 (55 g, 77% yield). MS[M+H]+=670

[1462] 2) Synthesis of compound 39-2

[1463] Using the same equivalence and method as in the synthesis of compound 36-2, compounds 39-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthalene-2-amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 39-2 (31.2 g, yield 76%). MS[M+H]+=913

[1464] 3) Synthesis of BD 9

[1465] Compound 39-2 (25 g) and boron triiodide (18.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 9 (7.3 g, yield 29%). MS[M+H]+=921

[1466] Synthesis Example 40. Synthesis of Compound BD 10

[1467]

[1468] 1) Synthesis of compound 40-1

[1469] Using the same equivalence and method as in the synthesis of compound 36-2, 2-chloro-N,N-bis(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)phenyl)dibenzo[b,d]furan-4-amine and 1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-10H-benzo[4,5]thieno[3,2-b]indole were used instead of compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 40-1 (28 g, 75% yield). MS[M+H]+=930

[1470] 2) Synthesis of BD 10

[1471] Compound 40-1 (25 g) and boron triiodide (17.9 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 10 (7.1 g, yield 28%). MS[M+H]+=938

[1472] Synthesis Example 41. Synthesis of Compound BD 11

[1473]

[1474] 1) Synthesis of compound 41-1

[1475] Using the same equivalences and methods as in the synthesis of compound 36-1, 3-bromo-1-chlorodibenzo[b,d]thiophene and di([1,1'-biphenyl]-4-yl)amine were used 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)phenyl-1,3-diamine. After the reaction was completed, the product was extracted and then recrystallized to obtain compound 41-1 (41.4 g, yield 72%). MS[M+H]+=539

[1476] 2) Synthesis of compound 41-2

[1477] Using the same equivalence and method as in the synthesis of compound 36-2, compounds 41-1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-5H-benzo[b]carbazole were used instead of compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 41-2 (28.8 g, 72% yield).

[1478] MS[M+H]+=720

[1479] 3) Synthesis of BD 11

[1480] Under a nitrogen atmosphere, compound 41-2 (25 g) and boron triiodide (23.1 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 11 (7.6 g, yield 30%). MS[M+H]+=728 Synthesis Example 42. Synthesis of compound BD 12

[1481]

[1482] 1) Synthesis of compound 42-1

[1483] 3-Bromo-5-chlorophenol (30 g), 9,9-diphenyl-9,10-dihydroacridine (37.2 g), sodium tert-butoxide (42 g), and bis(tri-tert-butylphosphine)palladium (0) (1.5 g) were introduced into toluene (600 ml) and refluxed for 1 hour. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 42-1 (51 g, yield 77%). MS[M+H]+=461

[1484] 2) Synthesis of compound 42-2

[1485] Compound 42-1 (30 g), 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole (31.7 g), tripotassium phosphate (49.8 g), and bis(tri-tert-butylphosphine)palladium (0) (0.8 g) were introduced into 1,4-di The mixture was refluxed in alkane (300 ml) and water (100 ml) for 2 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 42-2 (32.3 g, 73% yield). MS[M+H]+=682

[1486] 3) Synthesis of compound 42-3

[1487] Compound 42-2 (25 g) and boron triiodide (24.4 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 42-3 (7.3 g, yield 29%). MS[M+H]+=690

[1488] 4) Synthesis of compound 42-4

[1489] Compound 42-3 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.8 mL), and potassium carbonate (4.3 g) were introduced into tetrahydrofuran (70 mL) and water (30 mL), and stirred under reflux for 2 hours. After the reaction was complete, the product was extracted and then purified by column chromatography to obtain compound 42-4 (9.1 g, 92% yield). MS [M+H]+=972

[1490] 5) Synthesis of BD 12

[1491] Compound 42-4 (7 g), bis(4-(tert-butyl)phenyl)amine (2.1 g), pd(dba)2 (0.13 g), Xphos (0.21 g), and cesium carbonate (7.1 g) were introduced into xylene (100 ml) under a nitrogen atmosphere and stirred under reflux for 12 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 12 (5.1 g, 74% yield). MS[M+H]+=953

[1492] Synthesis Example 43. Synthesis of Compound BD 13

[1493]

[1494] 1) Synthesis of compound 43-1

[1495] Using the same equivalences and methods as in the synthesis of compound 31-1, 3-bromo-5-chloro-1,1'-biphenyl and 3,6-di(adamantane-1-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine, after the reaction was completed, the result was extracted and then recrystallized to obtain compound 43-1 (51 g, 73% yield). MS[M+H]+=623

[1496] 2) Synthesis of compound 43-2

[1497] Using the same equivalence and method as in the synthesis of compound 36-2, compound 43-1 was used instead of compound 36-1. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 43-2 (27.3 g, 78% yield). MS[M+H]+=730

[1498] 3) Synthesis of compound 43-3

[1499] Compound 43-2 (27 g), 4-bromo-1,1'-biphenyl (10.4 g), sodium tert-butoxide (32.3 g), and bis(tri-tert-butylphosphine)palladium (0) (1.2 g) were introduced into toluene (600 ml) under a nitrogen atmosphere and refluxed for 2 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 43-3 (25.4 g, yield 78%). MS[M+H]+=882

[1500] 4) Synthesis of BD 13

[1501] Under a nitrogen atmosphere, compound 43-3 (25 g) and boron triiodide (18.9 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 13 (7.3 g, yield 29%). MS[M+H]+=890 Synthesis Example 44. Synthesis of compound BD 14

[1502]

[1503] 1) Synthesis of compound 44-1

[1504] Using the same equivalences and methods as in the synthesis of compound 31-2, 3,6-di-tert-butyl-9-(5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)-9H-carbazole and N-([1,1'-biphenyl]-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)dibenzo[b,d]furan-2-amine were used instead of the compounds. 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine, after the reaction was completed, the product was extracted and then recrystallized to obtain compound 44-1 (38.2 g, yield 78%).

[1505] MS[M+H]+=771

[1506] 2) Synthesis of BD 14

[1507] Under a nitrogen atmosphere, compound 44-1 (25 g) and boron triiodide (21.6 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 14 (7.4 g, yield 29%). MS[M+H]+=779 Synthesis Example 45. Synthesis of compound BD 15

[1508]

[1509] 1) Synthesis of compound 45-1

[1510] Using the same equivalences and methods as in the synthesis of compound 31-1, 3-bromo-5-chloro-1,1'-biphenyl and 9,9-dimethyl-9,10-dihydroacridine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 45-1 (34 g, 77% yield). MS[M+H]+=396

[1511] 2) Synthesis of compound 45-2

[1512] Using the same equivalences and methods as in the synthesis of compound 31-2, compound 45-1 and N-([1,1'-biphenyl]-4-yl)-9,9,10,10-tetramethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9,10-dihydroanthracene-2-amine were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 45-2 (43.1 g, 75% yield). MS[M+H]+=764

[1513] 3) Synthesis of BD 15

[1514] Under a nitrogen atmosphere, compound 45-2 (25 g) and boron triiodide (21.8 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 15 (7.3 g, yield 29%). MS[M+H]+=772 Synthesis Example 46. Synthesis of compound BD 16

[1515]

[1516] 1) Synthesis of compound 46-1

[1517] Using the same equivalences and methods as in the synthesis of compound 36-1, 3-bromo-1-chloronaphthalene and 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole were used 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)phenyl-1,3-diamine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 46-1 (38.7 g, 75% yield). MS[M+H]+=419

[1518] 2) Synthesis of compound 46-2

[1519] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 46-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-fluorene-2-amine were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthalene-2-amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 46-2 (43.2 g, yield 77%). MS[M+H]+=784

[1520] 3) Synthesis of BD 16

[1521] Compound 46-2 (25 g) and boron triiodide (21.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 16 (7.3 g, yield 29%). MS[M+H]+=792

[1522] Synthesis Example 47. Synthesis of Compound BD 17

[1523]

[1524] 1) Synthesis of compound 47-1

[1525] Using the same equivalences and methods as in the synthesis of compound 31-1, 1-bromo-3-(tert-butyl)-5-chlorobenzene (30 g) and 12,12-dimethyl-5,12-dihydrobenzo[b]acridine (31.4 g) were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 47-1 (38.9 g, 75% yield).

[1526] MS[M+H]+=427

[1527] 2) Synthesis of compound 47-2

[1528] Using the same equivalence and method as in the synthesis of compound 31-2, compound 47-1 and N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 47-2 (37.7 g, 74% yield). MS[M+H]+=726

[1529] 3) Synthesis of BD 17

[1530] Compound 47-2 (25 g) and boron triiodide (22.9 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 17 (7.2 g, yield 28%). MS[M+H]+=734

[1531] Synthesis Example 48. Synthesis of Compound BD 18

[1532]

[1533] 1) Synthesis of compound 48-1

[1534] Using the same equivalences and methods as in the synthesis of compound 31-1, 3-bromo-5-chloro-1,1'-biphenyl and N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)benzo[b]thiophene-3-amine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amine. After the reaction was completed, the product was extracted and then recrystallized to obtain compound 48-1 (44 g, 72% yield).

[1535] MS[M+H]+=545

[1536] 2) Synthesis of compound 48-2

[1537] Using the same equivalences and methods as in the synthesis of compound 31-2, compound 48-1 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-fluorene-2-amine were substituted for compounds 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 48-2 (34.2 g, 71% yield). MS[M+H]+=870

[1538] 3) Synthesis of BD 18

[1539] Compound 48-2 (25 g) and boron triiodide (19.1 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 18 (7.2 g, yield 29%). MS[M+H]+=878

[1540] Synthesis Example 49. Synthesis of Compound BD 19

[1541]

[1542] 1) Synthesis of compound 49-1

[1543] Using the same equivalences and methods as in the synthesis of compound 31-2, N-(4-(tert-butyl)phenyl)-N-(5-chloro-[1,1'-biphenyl]-3-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine and 8-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-7H-benzo[c]carbazole were used instead of compound 3. 1-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were reacted. After the reaction was completed, the product was extracted and then recrystallized to obtain compound 49-1 (28.9 g, yield 73%).

[1544] MS[M+H]+=760

[1545] 2) Synthesis of BD 19

[1546] Compound 49-1 (25 g) and boron triiodide (21.9 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 19 (7.3 g, yield 29%). MS[M+H]+=768

[1547] Synthesis Example 50. Synthesis of Compound BD 20

[1548]

[1549] 1) Synthesis of compound 50-1

[1550] Using the same equivalence and method as in the synthesis of compound 36-1, N1-(5-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine was used instead of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)phenyl-1,3-diamine. After the reaction was completed, the product was extracted and then recrystallized to obtain compound 50-1 (46.1 g, 73% yield).

[1551] MS[M+H]+=593

[1552] 2) Synthesis of compound 50-2

[1553] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 50-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-3,6-di-o-tolyl-9H-carbazole were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 50-2 (33.2 g, yield 73%). MS[M+H]+=904

[1554] 3) Synthesis of BD 20

[1555] Compound 50-2 (25 g) and boron triiodide (18.4 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 20 (7.1 g, yield 28%). MS[M+H]+=912

[1556] Synthesis Example 51. Synthesis of Compound BD 21

[1557]

[1558] 1) Synthesis of compound 51-1

[1559] Using the same equivalences and methods as in the synthesis of compound 36-1, 3-bromo-1-chloronaphthalene and 5,5,8,8-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine were used 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)phenyl-1,3-diamine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 51-1 (55.5 g, 72% yield).

[1560] MS[M+H]+=621

[1561] 2) Synthesis of compound 51-2

[1562] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 51-1 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-fluorene-2-amine were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthalene-2-amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 51-2 (32.4 g, yield 71%). MS[M+H]+=946

[1563] 3) Synthesis of BD 21

[1564] Compound 51-2 (25 g) and boron triiodide (17.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 21 (7.3 g, yield 29%). MS[M+H]+=954

[1565] Synthesis Example 52. Synthesis of Compound BD 22

[1566]

[1567] 1) Synthesis of compound 52-1

[1568] Using the same equivalence and method as in the synthesis of compound 31-2, N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N-(5-chloro-[1,1'-biphenyl]-3-yl)-5-isopropylbenzo[b]thiophene-3-amine and 6-(tert-butyl)-4a,9a-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-2,3,4,4a,9,9a-hexahydro- 1H-carbazole was used to replace compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 52-1 (31.1 g, 75% yield). MS[M+H]+=808

[1569] 2) Synthesis of BD 22

[1570] Compound 52-1 (25 g) and boron triiodide (20.6 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 22 (7.3 g, yield 29%). MS[M+H]+=816

[1571] Synthesis Example 53. Synthesis of Compound BD 23

[1572]

[1573] 1) Synthesis of compound 53-1

[1574] Using the same equivalences and methods as in the synthesis of compound 36-1, 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 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)phenyl-1,3-diamine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 53-1 (54.5 g, 72% yield). MS[M+H]+=613

[1575] 2) Synthesis of compound 53-2

[1576] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 53-1 and 3,6-di-tert-butyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-carbazole were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 53-2 (31.1 g, yield 74%). MS[M+H]+=856

[1577] 3) Synthesis of BD 23

[1578] Under a nitrogen atmosphere, compound 53-2 (25 g) and boron triiodide (19.5 g) were introduced into 1,2-dichlorobenzene (250 ml), and the mixture was stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 23 (7.1 g, yield 28%). MS[M+H]+=864 Synthesis Example 54. Synthesis of compound BD 24

[1579]

[1580] 1) Synthesis of compound 54-1

[1581] Using the same equivalence and method as in the synthesis of compound 36-1, N1-(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 substituted for N3,N3-bis(4-(tert-butyl)phenyl)phenyl-1,3-diamine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 54-1 (54 g, 78% yield). MS[M+H]+=653

[1582] 2) Synthesis of compound 54-2

[1583] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 54-1 and 4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-3-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl-2-yl)amino)phenol were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 54-2 (32.2 g, 77% yield). MS[M+H]+=912

[1584] 3) Synthesis of compound 54-3

[1585] Compound 54-2 (25 g) and boron triiodide (18.3 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 54-3 (7.3 g, yield 29%). MS[M+H]+=920

[1586] 4) Synthesis of compound 54-4

[1587] Compound 54-3 (7 g), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (2.1 ml), and potassium carbonate (3.2 g) were introduced into tetrahydrofuran (70 ml) and water (30 ml), and stirred under reflux for 2 hours. After the reaction was complete, the product was extracted and then purified by column chromatography to obtain compound 54-4 (8.8 g, 96% yield). MS [M+H]+=1201

[1588] 5) Synthesis of BD 24

[1589] Compound 54-4 (7 g), bis(4-(tert-butyl)phenyl)amine (1.7 g), pd(dba)2 (0.11 g), Xphos (0.18 g), and cesium carbonate (5.7 g) were introduced into xylene (100 ml) under a nitrogen atmosphere and stirred under reflux for 12 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 24 (5.1 g, 74% yield). MS[M+H]+=1183

[1590] Synthesis Example 55. Synthesis of Compound BD 25

[1591]

[1592] 1) Synthesis of compound 55-1

[1593] Using the same equivalence and method as in the synthesis of compound 36-1, 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]naphthyl-3-amine were used 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)phenyl-1,3-diamine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 55-1 (52 g, 76% yield). MS[M+H]+=705

[1594] 2) Synthesis of compound 55-2

[1595] Using the same equivalence and method as in the synthesis of compound 36-2, compounds 55-1 and 6-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-7H-benzo[c]carbazole were used instead of compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthyl-2-amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 55-2 (27.7 g, 73% yield).

[1596] MS[M+H]+=886

[1597] 3) Synthesis of BD 25

[1598] Compound 55-2 (25 g) and boron triiodide (18.8 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 25 (7.5 g, 30% yield). MS[M+H]+=894

[1599] Synthesis Example 56. Synthesis of Compound BD 26

[1600]

[1601] 1) Synthesis of compound 56-1

[1602] Using the same equivalence and method as in the synthesis of compound 34-1, 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophene-3-amine was used instead of N1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthyl-2-yl)-N3,N3-diphenylphenyl-1,3-diamine. After the reaction was complete, the result was extracted and then recrystallized to obtain compound 56-1 (44 g, 75% yield). MS[M+H]+=525

[1603] 2) Synthesis of compound 56-2

[1604] Using the same equivalence and method as in the synthesis of compound 31-2, compound 56-1 and 2-(tert-butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-5H-benzo[b]carbazole were used instead of compound 31-1 and N-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-4-amine were extracted after the reaction was complete and then recrystallized to obtain compound 56-2 (31.1 g, 71% yield). MS[M+H]+=762

[1605] 3) Synthesis of BD 26

[1606] Compound 56-2 (25 g) and boron triiodide (21.9 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 26 (7.2 g, yield 29%). MS[M+H]+=770

[1607] Synthesis Example 57. Synthesis of Compound BD 27

[1608]

[1609] 1) Synthesis of compound 57-1

[1610] Using the same equivalence and method as in the synthesis of compound 36-1, bis(4-(tert-butyl)phenyl)amine was used instead of N1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-N3,N3-bis(4-(tert-butyl)phenyl)phenyl-1,3-diamine. After the reaction was complete, the product was extracted and then recrystallized to obtain compound 57-1 (37 g, yield 72%). MS[M+H]+=483

[1611] 2) Synthesis of compound 57-2

[1612] Using the same equivalences and methods as in the synthesis of compound 36-2, compounds 57-1 and N-(4-(tert-butyl)phenyl)-9,9-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-9H-fluorene-2-amine were substituted for compounds 36-1 and 3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)naphthalene-2-amine. After the reaction was completed, the result was extracted and then recrystallized to obtain compound 57-2 (35.2 g, 72% yield). MS[M+H]+=788

[1613] 3) Synthesis of BD 27

[1614] Compound 57-2 (25 g) and boron triiodide (21.1 g) were introduced into 1,2-dichlorobenzene (250 ml) under a nitrogen atmosphere and stirred at 160 °C for 4 hours. After the reaction was complete, the product was extracted and then recrystallized to obtain BD 27 (7.6 g, 30% yield). MS[M+H]+=796

[1615] [Example]

[1616] Example 1

[1617] A glass substrate coated with a 150 nm thick ITO (indium tin oxide) film was immersed in distilled water containing a cleaning agent and ultrasonically cleaned. In this study, Fischer Co.'s product was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes each time with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropanol, acetone, and methanol solvents, then dried and transferred to a plasma cleaner. Additionally, the substrate was cleaned with nitrogen plasma for 5 minutes and then transferred to a vacuum deposition apparatus.

[1618] On the transparent ITO electrode prepared above, the following HAT-CN compound was thermally vacuum-deposited to a thickness of 5 nm to form a hole injection layer. Subsequently, 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. Then, a light-emitting layer with a thickness of 20 nm was formed by simultaneously vacuum-depositing the following compound BD1 as a dopant and compound BH1 as the host (weight ratio 5:95). 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. Finally, aluminum was deposited to a thickness of 100 nm to form a cathode, resulting in the fabrication of an organic light-emitting device.

[1619] In the above process, the deposition rate of the organic material was maintained between 0.04 nm / s and 0.09 nm / s, the deposition rate of the lithium fluoride electron transport layer was maintained at 0.03 nm / s, the deposition rate of the aluminum cathode was maintained at 0.2 nm / s, and the vacuum level during deposition was maintained at 1 × 10⁻⁶. -7 Up to 5×10 -5 To manufacture organic light-emitting devices.

[1620]

[1621] Examples 2 to 97

[1622] Organic light-emitting devices were fabricated in the same manner as in Example 1, except that compounds BH2 to BH30 were used instead of BH1 as the host compound of the light-emitting layer, or compounds BD2 to BD27 were used instead of BD1 as the dopant compound.

[1623]

[1624]

[1625]

[1626]

[1627] Comparative Examples 1 to 15

[1628] Organic light-emitting devices were fabricated in the same manner as in Example 1, except that compounds BHA to BHC were used instead of BH1 as the host compound of the light-emitting layer, or compounds BDA to BDD were used instead of BD1 as the dopant compound.

[1629]

[1630] For each organic light-emitting device manufactured in the examples and comparative examples, at 10 mA / cm 2 The drive voltage and efficiency were measured at a current density of 20 mA / cm². 2 The time (T95) taken for the brightness to become 95% of the initial brightness at a given current density was measured. The results are shown in Table 1 below.

[1631] [Table 1]

[1632]

[1633]

[1634]

[1635]

[1636] As shown in Table 1, it can be seen that the devices of Examples 1 to 97, which include both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H of this disclosure, have the characteristics of low voltage, high efficiency, and long lifespan. In particular, compared with devices that do not contain Chemical Formula 1 and Chemical Formula H (Comparative Examples 1 to 3), devices that contain only one of Chemical Formula 1 and Chemical Formula H of this disclosure (Comparative Examples 4 to 15) exhibit comparable or inferior characteristics; however, devices that contain both Chemical Formula 1 and Chemical Formula H of this disclosure (Examples 1 to 97) exhibit superior characteristics.

Claims

1. An organic light-emitting device, comprising: anode; cathode; as well as An organic material layer disposed between the anode and the cathode. The organic material layer includes a light-emitting layer; and The luminescent layer comprises compounds represented by the following chemical formulas 1-2 and compounds represented by the following chemical formula H: [Chemical Formula 1-2] In chemical formulas 1-2, R5 to R8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring group of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; Ar2 is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused cycloalkanes of substituted or unsubstituted aromatic and aliphatic rings; or a substituted or unsubstituted heterocyclic group, or bonded to R5 to form a substituted or unsubstituted ring; When Ar2 and R5 form benzo[ When the azinon ring is present, the benzo[a] The azine ring is an unsubstituted benzo[a] group. Azine ring; Z1 to Z3 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; and 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 fused cyclic group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group; and R and R' may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring. [Chemical formula H] In the chemical formula H, L20 and L21 may be the same as or different from each other, and each is a direct bond independently; or a substituted or unsubstituted aryl group; Ar20 and Ar21 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group; At least one of Ar20 and Ar21 is a substituted or unsubstituted heterocyclic group; R200 and R201 may be the same as or different from each other, 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; and r201 is an integer from 1 to 7, and when r201 is 2 or greater, two or more R201s are the same or different from each other.

2. The organic light-emitting device according to claim 1, wherein chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-6: [Chemical Formula 1-2-1] [Chemical Formula 1-2-2] [Chemical Formula 1-2-3] [Chemical Formula 1-2-4] [Chemical Formula 1-2-5] [Chemical Formula 1-2-6] In chemical formulas 1-2-1 to 1-2-6, X1, A11 and Z1 to Z3 have the same limitations as in chemical formulas 1-2; X3 to X6 may be the same as or different from each other, and each is independently CRR', NR'', O or S; Y2 is CG1G2, SiG8G9, NG101, O, or S; y2 is either 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 fused cyclic group of aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group; R, R' and R'' are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or they are bonded to each other to form a substituted or unsubstituted ring; R'5 to R'8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused cyclic group of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group; G1, G2, G7 to G12, G14, G15, G16 and G101 are the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted arylalkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or unsubstituted aryl; substituted or unsubstituted fused ring of aromatic and aliphatic hydrocarbon rings; or substituted or unsubstituted heterocyclic group, or adjacent groups bonded to each other to form substituted or unsubstituted aromatic hydrocarbon rings; substituted or unsubstituted aliphatic hydrocarbon rings; or substituted or unsubstituted fused ring of aromatic and aliphatic hydrocarbon rings; g7, g15, and g16 are each integers from 1 to 4; g10 is an integer from 1 to 8; g14 is 1 or 2; When g7, g10, g15 and g16 are each 2 or greater, the substituents in two or more brackets are the same or different from each other; When g14 is 2, the substituents in the two brackets are either the same or different from each other; Ar'1 and Ar'2 may be identical or different from each other, and each is independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a fused cyclic group of an aromatic or aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group; and In chemical formula 1-2-2, When y2 is 1 and Y2 is 0, G7 and R'6 to R'8 are hydrogen.

3. The organic light-emitting device according to claim 1, wherein adjacent groups in 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] [Chemical formula C-2] In chemical formulas C-1 and C-2, J1 is O, S, NQ7, CQ8Q9 or SiQ10Q11; W1 to W8 and Q7 to Q11 may be the same as or different from each other, and each is independently 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 amino group; a substituted or unsubstituted aryl group; a fused ring group of substituted or unsubstituted aromatic and aliphatic hydrocarbon rings; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring; and * indicates the site that is bonded to chemical formula 1-2.

4. The organic light-emitting device according to claim 1, wherein at least one of Ar2O and Ar21 is represented by the following chemical formula Het1: [Chemical formula Het1] In the chemical formula Het1, The dashed line connects to the chemical formula H; M1 is either 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 bonded to an adjacent group to form a substituted or unsubstituted ring; and r11 is an integer from 0 to 7, and when r11 is 2 or greater, R11 is either the same or different from each other.

5. The organic light-emitting device according to claim 4, wherein the chemical formula Het1 is represented by any one of the following chemical formulas Het2 to Het4: [Chemical formula Het2] [Chemical formula Het3] [Chemical formula Het4] In the chemical formulas Het2 to Het4 The dashed line and M1 have the same definition as in the chemical 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; and r11' is an integer from 0 to 9, and when r11' is 2 or greater, R11 is either the same or different from each other.

6. The organic light-emitting device according to claim 1, wherein the chemical formula H is represented by any one of the following chemical formulas H-1 to H-4: [Chemical formula H-1] [Chemical formula H-2] [Chemical formula H-3] [Chemical formula H-4] In chemical formulas H-1 to H-4, L20, L21, R200, R201, and r201 have the same limitations as in chemical formula H; M1 is either O or S; M2 is O, S, or NR13; Ar20 and Ar21 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently; R11 to R13 may be the same as or different from each other, and each is independently 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 bonded to an adjacent group to form a substituted or unsubstituted ring; and r11 and r12 are integers from 0 to 7, and when r11 and r12 are 2 or greater, the substituents in parentheses are either the same or different from each other.

7. The organic light-emitting device according to claim 1, wherein chemical formulas 1-2 are selected from any of the following compounds:

8. The organic light-emitting device according to claim 1, wherein chemical formula H is selected from any of the following compounds: 。 9. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises compounds represented by chemical formulas 1-2 and 30-70 in a weight ratio of 1:99 to 30:70.

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